CN113493690B - Compound, liquid crystal composition and liquid crystal display element - Google Patents
Compound, liquid crystal composition and liquid crystal display element Download PDFInfo
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- CN113493690B CN113493690B CN202110274111.1A CN202110274111A CN113493690B CN 113493690 B CN113493690 B CN 113493690B CN 202110274111 A CN202110274111 A CN 202110274111A CN 113493690 B CN113493690 B CN 113493690B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 677
- 239000000203 mixture Substances 0.000 title claims abstract description 277
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 189
- 125000004432 carbon atom Chemical group C* 0.000 claims description 268
- 125000000217 alkyl group Chemical group 0.000 claims description 169
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 92
- 239000000126 substance Substances 0.000 claims description 83
- 125000002947 alkylene group Chemical group 0.000 claims description 78
- 125000003342 alkenyl group Chemical group 0.000 claims description 77
- 125000001153 fluoro group Chemical group F* 0.000 claims description 51
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- -1 naphthalene-1, 4-diyl Chemical group 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 30
- 238000006467 substitution reaction Methods 0.000 claims description 30
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 18
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 8
- 125000006850 spacer group Chemical group 0.000 claims description 6
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 41
- 230000015572 biosynthetic process Effects 0.000 abstract description 35
- 238000006116 polymerization reaction Methods 0.000 abstract description 19
- 230000004043 responsiveness Effects 0.000 abstract 1
- 239000000758 substrate Substances 0.000 description 41
- 230000007704 transition Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 28
- 230000006872 improvement Effects 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 230000004044 response Effects 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 230000000694 effects Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000012535 impurity Substances 0.000 description 11
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003302 alkenyloxy group Chemical group 0.000 description 6
- 210000002858 crystal cell Anatomy 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 125000005755 decalin-2,6-ylene group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C([H])([*:2])C([H])([H])C([H])([H])C2([H])C([H])([H])C1([H])[*:1] 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000005725 cyclohexenylene group Chemical group 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002391 heterocyclic compounds Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- UZFBWSFTHSYXCN-UHFFFAOYSA-N (4-hydroxy-3-methoxyphenyl)boronic acid Chemical compound COC1=CC(B(O)O)=CC=C1O UZFBWSFTHSYXCN-UHFFFAOYSA-N 0.000 description 1
- COIQUVGFTILYGA-UHFFFAOYSA-N (4-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=C(O)C=C1 COIQUVGFTILYGA-UHFFFAOYSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- JHRIPENGTGSNPJ-UHFFFAOYSA-N 2-amino-4-bromophenol Chemical compound NC1=CC(Br)=CC=C1O JHRIPENGTGSNPJ-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- MZZDYNDEBXBRLG-UHFFFAOYSA-N 4-(1,1-dioxothian-4-yl)phenol Chemical compound C1=CC(O)=CC=C1C1CCS(=O)(=O)CC1 MZZDYNDEBXBRLG-UHFFFAOYSA-N 0.000 description 1
- URRMZFVHLMEXFA-UHFFFAOYSA-N 4-(3-fluoro-4-hydroxyphenyl)-2-nitrophenol Chemical group C1=C(F)C(O)=CC=C1C1=CC=C(O)C([N+]([O-])=O)=C1 URRMZFVHLMEXFA-UHFFFAOYSA-N 0.000 description 1
- OAEHQYNHWARVBB-UHFFFAOYSA-N 4-[4-(oxan-2-yloxy)phenyl]phenol Chemical group C1=CC(O)=CC=C1C(C=C1)=CC=C1OC1OCCCC1 OAEHQYNHWARVBB-UHFFFAOYSA-N 0.000 description 1
- IEMJHIWFWIZOMG-UHFFFAOYSA-N 4-bromo-2-(3-hydroxypropyl)phenol Chemical compound OCCCC1=CC(Br)=CC=C1O IEMJHIWFWIZOMG-UHFFFAOYSA-N 0.000 description 1
- BMUQUGIUTGEGNH-UHFFFAOYSA-N 6-amino-4-phenylcyclohexa-2,4-diene-1,1-diol Chemical group NC(C(C=C1)(O)O)C=C1C1=CC=CC=C1 BMUQUGIUTGEGNH-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- FHHSEFRSDKWJKJ-UHFFFAOYSA-N nepetin Chemical compound C=1C(=O)C2=C(O)C(OC)=C(O)C=C2OC=1C1=CC=C(O)C(O)=C1 FHHSEFRSDKWJKJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
Abstract
本发明提供一种化合物、液晶组合物和液晶显示元件。本发明所要解決的课题在于，提供能够实现高速响应性和高电压保持率(VHR)的液晶显示元件，并且提供能够同时实现快聚合速度、适当的倾斜形成、高倾斜稳定性、高电压保持率(VHR)的含有聚合性化合物的液晶组合物和使用其的烧屏(IS)被充分抑制或不发生的PSA型或PSVA型的液晶显示元件以及适合调制上述含有聚合性化合物的液晶组合物的化合物。解决课题的方法在于，本发明提供分子中具有通式(Y)所表示的结构的化合物、含有该化合物的液晶组合物以及使用该液晶组合物的元件。[化1] The present invention provides a compound, a liquid crystal composition and a liquid crystal display element. The problem to be solved by the present invention is to provide a liquid crystal display element capable of achieving high-speed responsiveness and high voltage holding ratio (VHR), and to provide a liquid crystal composition containing a polymerizable compound that can simultaneously achieve fast polymerization speed, appropriate tilt formation, high tilt stability, and high voltage holding ratio (VHR), and a PSA-type or PSVA-type liquid crystal display element in which screen burn-in (IS) is fully suppressed or does not occur, and a compound suitable for modulating the above-mentioned liquid crystal composition containing a polymerizable compound. The method for solving the problem is that the present invention provides a compound having a structure represented by the general formula (Y) in the molecule, a liquid crystal composition containing the compound, and an element using the liquid crystal composition. [Chemistry 1]
Description
Technical Field
The present invention relates to a liquid crystal composition, a liquid crystal display element using the same, and a polymerizable compound.
Background
In liquid crystal display devices using liquid crystal compositions having negative dielectric anisotropy Δ∈ and in which PSA, PSVA-type liquid crystal TV, liquid crystal monitor, and the like are widely used, various polymerizable compounds and liquid crystal compositions containing the same are disclosed in patent document 1, patent document 2, patent document 3, patent document 4, patent document 5, and the like as liquid crystal compositions suitable for these applications.
However, the characteristics of the liquid crystal compositions containing a polymerizable compound which have been conventionally used are not sufficient for high-definition liquid crystal TVs such as 4K and 8K. Specifically, the liquid crystal display elements of 4K and 8K require high definition pixels, and considerable UV light is cut off due to the increase in the area of the wiring and the light shielding portion. Therefore, in the UV irradiation step in the production of PSA-type and PSVA-type liquid crystal display elements, the polymerizable compound cannot be sufficiently polymerized and a large amount of polymerizable compound remains. This confirms that the tilt formation IS insufficient, the response speed IS deteriorated, the orientation IS deteriorated, and the residual polymerizable compound IS slowly polymerized during driving, and the tilt IS changed, which results in a defective display called burn-In (IS).
Based on the above, a PSA-type or PSVA-type liquid crystal display element such as a high-definition liquid crystal television or a liquid crystal monitor is required to have extremely high characteristics different from those of the prior art, and a liquid crystal composition which can be stably produced with less UV light than the prior art is required.
Prior art literature
Patent literature
Patent document 1 Japanese patent laid-open publication 2016-216747
Patent document 2 Japanese patent No. 4803320
Patent document 3 Japanese patent No. 6008065
Patent document 4 Japanese patent No. 6233550
Patent document 5 Japanese patent No. 5743132
Disclosure of Invention
Problems to be solved by the invention
The liquid crystal composition has a problem that it is easily degraded by light emitted from a backlight and active energy rays such as ultraviolet rays irradiated during the manufacturing process of a liquid crystal display element, and that impurities generated by the photodegradation of the liquid crystal composition cause a decrease in the Voltage Holding Ratio (VHR) of the liquid crystal panel. Therefore, a liquid crystal display element capable of realizing both high-speed response and high VHR is demanded.
The invention provides a liquid crystal display element capable of realizing high-speed response and high Voltage Holding Ratio (VHR). The purpose of the present invention IS to provide a liquid crystal composition containing a polymerizable compound, which can simultaneously achieve a high polymerization rate, an appropriate tilt formation, a high tilt stability, and a high Voltage Holding Ratio (VHR), a PSA-type or PSVA-type liquid crystal display element using the same, in which burn-In (IS) IS sufficiently suppressed or does not occur, and a compound suitable for preparing the liquid crystal composition containing the polymerizable compound.
Means for solving the problems
As a result of intensive studies, the present inventors have found that the above problems can be solved by a liquid crystal composition containing one or more compounds having a specific chemical structure, and have completed the present application.
Effects of the invention
The liquid crystal composition of the present invention can simultaneously realize a high polymerization rate, a suitable tilt formation, a high tilt stability, and a high VHR by containing one or two or more compounds having the above-mentioned specific chemical structures, which are excellent in solubility in the liquid crystal composition and low-temperature storage property. Further, by using the liquid crystal composition of the present invention, a PSA-type or PSVA-type liquid crystal display element which exhibits excellent display quality with or without occurrence of burn-In (IS) and which forms high-definition pixels can be provided.
Detailed Description
First, the liquid crystal composition of the present invention will be described. In the following description, "total amount" means "total mass", and unit "%" of the content of each compound means "% by mass".
(Polar Compound)
The liquid crystal composition of the present invention contains a polar compound that has a function of adsorbing and trapping polar impurities such as ionic compounds and radical compounds present in the liquid crystal composition. Further, the polar compound has a polar group in its structure, and therefore the polar group is adsorbed on the substrate surface sandwiching the liquid crystal composition (liquid crystal layer) and is biased in the vicinity of the substrate surface. In particular, since the polar compound is a polymerizable polar compound having a polymerizable group in its structure, the resistivity and VHR of the liquid crystal composition and the liquid crystal layer can be improved by the effect of the polymer obtained by polymerization of the polymerizable polar compound.
Regarding factors of resistivity and VHR decrease, it is considered that impurities are dispersed (diffused) in the liquid crystal layer. In the present invention, it is presumed that the polar group of the polymer obtained by polymerization of the polymerizable polar compound is bonded to the impurity or a polar attractive force corresponding to the bonding is formed, and the impurity is fixed to the polymer obtained by polymerization of the polymerizable polar compound. In this way, the impurities are adsorbed and trapped by the polymer obtained from the polymerizable polar compound, and thus the impurities do not diffuse in the entire liquid crystal layer, and can be immobilized in the vicinity of the substrate surface, so that the reduction in resistivity and VHR due to the impurities can be suppressed. The polar group may be a structure capable of functioning as a donor or an acceptor of protons having hydrogen bonds, for example, and may function as either a donor or an acceptor, or both.
The polymerizable polar compound also interacts with the substrate surface of the liquid crystal display element, and is likely to move from the liquid crystal composition to the substrate surface and locally exist. Therefore, it is considered that the polymerization is efficiently performed in a state where the monomer is accumulated on the substrate surface during UV irradiation, and the polymerizable compound remaining in the liquid crystal layer can be effectively reduced, and thus the effect of improving the resistivity and VHR of the liquid crystal composition and the liquid crystal layer is also exhibited.
According to the present invention, the polar compound having the structure represented by the general formula (Y) is excellent in solubility in the liquid crystal composition and less in precipitation, and when the polar compound is added to the liquid crystal composition containing a polymerizable compound, the polymerization rate is sufficiently high and the polymerization reaction sufficiently proceeds, so that the liquid crystal composition containing a polymerizable compound can be produced with a small residual amount of unreacted polymerizable compound after the polymerization.
The polar compound of the present invention is preferably a compound comprising a structure represented by the general formula (Y).
[ Chemical 1]
(Wherein, the black dots represent bond bonds,
X y1 represents CR y3 or a nitrogen atom, R y3 represents a group selected from the group consisting of a hydrogen atom, P y1-Sy1 -or a straight or branched alkyl group having 1 to 30 carbon atoms, the hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, -CH 2 -in the alkyl group may be substituted with-CH=CH-, -C≡C-, -CO-, -O-, -S-, -NH-, -COO OCO-or-OCOO but-O-is discontinuous, P y1 represents a polymerizable group, S y1 is a single bond or a straight or branched alkylene group having 1 to 12 carbon atoms, the hydrogen atom in the alkylene group may be substituted with a halogen atom, -CH 2 -in the alkylene group may be substituted with-CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -NH-or-S-but more than 2-O-is discontinuous to cause adjacency,
X y2 and X y3 are each independently a single bond or an alkylene group having 1 to 6 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, the-CH 2 -group in the alkylene group may be represented by-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-substitution but more than 2-O-are not consecutive resulting in abutment. ).
In the case where X y1 is a nitrogen atom, the polarity of the structure represented by the general formula (Y) can be further improved, and thus it is particularly preferable from the viewpoint of improving the reliability of the liquid crystal composition.
In addition, X y1 is also preferably a structure represented by CR y3. R y3 preferably represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, P y1-Sy1 -and a straight-chain or branched alkyl group having 1 to 30 carbon atoms, the hydrogen atom in the alkyl group may be substituted with a halogen atom, the-CH 2 -groups in the alkyl groups may be substituted by-CH=CH-, -C.ident.C-, -O-, -COO-, -OCO-or-OCOO-groups (-O-discontinuities), more preferably represents a group selected from the group consisting of a hydrogen atom, a P y1-Sy1 -or a straight or branched alkyl group having 1 to 12 carbon atoms, the hydrogen atom in the alkyl group may be substituted with a halogen atom, of the alkyl groups, -CH 2 -may be substituted with-CH=CH-, -C≡C-, -O-, -COO-, -OCO-, or-OCOO (-O-discontinuous), more preferably represents a group selected from the group consisting of a hydrogen atom, P y1-Sy1 -, and a linear or branched alkyl group having 1 to 6 carbon atoms, the hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom, the-CH 2 -group in the alkyl group may be substituted with-CH=CH-, -C.ident.C-, -O-, -COO-, -OCO-or-OCOO-and represents a-O-discontinuous group.
P y1 represents a polymerizable group.
S y1 is preferably a single bond or a straight-chain or branched alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, the-CH 2 -group in the alkylene group may be replaced by-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, OCOO-, -O-, or-S-substitution (more than 2-O-are not contiguous and result in adjacency), more preferably a single bond or a straight or branched alkylene group having 1 to 6 carbon atoms, the hydrogen atom in the alkylene group may be substituted with a fluorine atom or a chlorine atom, the alkylene group may be represented by-CH 2 -CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, or-S-substitution and means that more than 2-O-are not consecutive resulting in contiguous groups.
X y2 and X y3 are each independently a single bond or an alkylene group having 1 to 6 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, the alkylene group may be substituted with-CH 2 -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-or-S-in which 2 or more-O-groups are not continuous and thus adjacent, more preferably a single bond or an alkylene group having 1 to 3 carbon atoms, the hydrogen atom in the alkylene group may be substituted with a halogen atom, in the alkylene group, -CH 2 -, may be substituted with-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, or-S-but more than 2-O-are not continuous to cause adjacent, more preferably a single bond or an alkylene group having 1 to 2 carbon atoms, the hydrogen atom in the alkylene group may be substituted with a fluorine atom or a chlorine atom, and-CH 2 -in the alkylene group may be substituted with-CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -O-, or-S-, and represents that 2 or more-O-groups are not continuous to cause adjacent groups.
The polar compound having a structure represented by the general formula (Y) is preferably a polymerizable polar compound. The polymerizable polar compound is preferably a compound represented by the following general formula (Y-1).
[ Chemical 2]
(Wherein X y1、Xy2 and X y3 represent the same meanings as those of X y1、Xy2 and X y3 in the general formula (Y),
R y1 and R y2 each independently represent a group selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, P y2-Sy2 -, a linear or branched alkyl group having 1 to 30 carbon atoms, and a structure represented by the general formula (Y), the hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group, a nitro group, P y2-Sy2 -or a structure represented by the general formula (Y), the-CH 2 -group in the alkyl group may be replaced by-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-substitution but more than 2-O-are not consecutive resulting in adjacency,
S y3 is a single bond or a straight chain or branched chain alkylene group having 1 to 30 carbon atoms, a hydrogen atom in the alkylene group may be substituted with P y2-Sy2 -, a halogen atom, a cyano group or a nitro group, the-CH 2 -group in the alkylene group may be represented by-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-substitution but more than 2-O-are not consecutive resulting in adjacency,
P y2 represents a polymerizable group and,
S y2 is a single bond or a straight chain or branched chain alkylene group having 1 to 12 carbon atoms, wherein a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, the-CH 2 -group in the alkylene group may be replaced by-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-substitution but more than 2-O-are not consecutive resulting in adjacency,
Z y1 and Z y2 each independently represent a single bond 、-C2H4-、-C4H8-、-C3H6-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-OCOOCH2-、-CH2OCOO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH2OCO-、-COOCH2-、-OCOCH2-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2- or-C.ident.C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),
M y2 each independently represents a 3-valent aromatic group, a 3-valent cycloaliphatic group, a 3-valent heterocyclic compound group, a 3-valent condensed ring or a 3-valent condensed polycyclic ring, the hydrogen atoms in these ring structures may be substituted by L y1,
M y1 and M y3 each independently represents a 2-valent aromatic group, a 2-valent cycloaliphatic group, a 2-valent heterocyclic compound group, a 2-valent condensed ring or a 2-valent condensed polycyclic ring, hydrogen atoms in the ring structures of which may be substituted by L y1, L y1 represents P y2-Sy2 -, a halogen atom, a cyano group, a nitro group, a straight-chain or branched alkyl group having 1 to 30 carbon atoms or a structure represented by the general formula (Y), the hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group, a nitro group, P y2-Sy2 -or a structure represented by the general formula (Y), the alkyl group may be substituted with-CH 2 -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but more than 2-O-may not be continuous to cause adjacency, where there are plural L y1, they may be the same or different,
M and n each independently represent an integer of 0 to 4, wherein the sum of m+n is 0 to 6,
Wherein the total number of P y1 and P y2 contained in the structure represented by the general formula (Y-1) is at least 1. ).
R y1 and R y2 are each preferably independently a group selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, P y2-Sy2 -, a linear or branched alkyl group having 1 to 30 carbon atoms, or a structure represented by the general formula (Y), wherein the hydrogen atom in the alkyl group may be replaced by a halogen atom, cyano, nitro, P y2-Sy2 -or structural substitution represented by the general formula (Y), the-CH 2 -group in the alkyl group may be replaced by-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-substitution (more than 2-O-not being consecutive and leading to adjacency), more preferably each independently is selected from the group consisting of a hydrogen atom, fluorine atom, chlorine atom, cyano group, P y2-Sy2 -or straight-chain or branched alkyl group having 1 to 12 carbon atoms, wherein hydrogen atom in the alkyl group may be substituted with halogen atom, P y2-Sy2 -or cyano group, and-CH 2 -in the alkyl group may be substituted with-CH=CH-, -c≡c-, -CO-, -COO-, -OCO-, -O-, or-S-substitution (more than 2-O-S are not contiguous and are not contiguous), more preferably each independently a group selected from the group consisting of a hydrogen atom, a fluorine atom, a chlorine atom, P y2-Sy2 -or a linear or branched alkyl group having 1 to 12 carbon atoms, the hydrogen atom in the alkyl group being optionally substituted with a fluorine atom, a chlorine atom or P y2-Sy2 -, the-CH 2 -in the alkyl group being optionally substituted with-ch=ch- -CO-, -COO-, -OCO-, -O-, or-S-substitution (more than 2-O-are not consecutive and result in abutment). In particular, from the viewpoint of pretilt angle stability, both R y1 and R y2 are each independently particularly preferably the structure represented by P y2-Sy2 -.
S y3 is preferably a single bond or a straight or branched alkylene group having 1 to 30 carbon atoms, the hydrogen atom in the alkylene group may be substituted with P y2-Sy2 -, a halogen atom, a cyano group or a nitro group, the alkylene group may be substituted with-CH 2 -CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-, wherein more than 2-O-are not continuous and result in adjacency, more preferably a single bond or a straight or branched alkylene group having 1 to 12 carbon atoms, the hydrogen atom in the alkylene group may be substituted with P y2-Sy2 -, a halogen atom, a cyano group or a nitro group, the alkylene group may be substituted with-CH 2 -CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -O-or-S-, wherein more than 2-O-are not continuous and thus adjacent, more preferably a single bond or a straight-chain or branched alkylene group having 1 to 6 carbon atoms, more preferably a single bond or the number of carbon atoms 1 to 6 linear or branched alkylene groups.
S y2 is preferably a single bond or a straight-chain or branched alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, -CH 2 -in the alkylene group may be substituted with-CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO O-, -NH-or-S-, wherein 2 or more-O-are not continuous to cause adjacency, more preferably a straight-chain or branched alkylene group having 1 to 6 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, -CH 2 -in the alkylene group may be substituted with-CH=CH-, -C≡C-, -CO-, -COO OCO-, -O-, -NH-or-S-, wherein 2 or more-O-in the alkylene group may not be continuous to cause adjacency, and further preferably a straight-chain or branched alkylene group having 1 to 6 carbon atoms, wherein a hydrogen atom in the alkylene group may be substituted with a fluorine atom, a cyano group or a chlorine atom or a cyano group, and wherein-CH=C-, -COO-, -O-, -C..
Z y1 and Z y2 are each independently preferably a single bond 、-C2H4-、-C4H8-、-C3H6-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-OCOOCH2-、-CH2OCOO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH2OCO-、-COOCH2-、-OCOCH2-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2- or-C.ident.C- (wherein Ra is each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), more preferably a single bond 、-C2H4-、-C4H8-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCOOCH2-、-CH2OCOO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2- or-C.ident.C- (wherein, ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), and more preferably a single bond 、-C2H4-、-C4H8-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-、-CF＝CF-、-CF2O-、-OCF2-、-CF2CF2- or-C.ident.C- (wherein Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
M y1、My2 and M y3 each independently preferably represent a group selected from the group consisting of the following formulas (T-1) to (T-21).
[ Chemical 3]
(Wherein, any of-CH=may be substituted with-N=independently of each other, and a bond may be present at any position, -CH 2 -each independently of the others may be represented by-O-, -S-, -NR 0 - (wherein, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), -CS-or-CO-substitution, but does not include an-O-O-bond. In addition, these groups are also preferably substituted by L y1.
In the case of importance of solubility in the liquid crystal composition, (T-1), (T-2), (T-3), (T-4) and (T-7) are preferable, in the case of importance of high reactivity, (T-4), (T-11), (T-16) and (T-20) are preferable, in the case of importance of good pretilt angle formation, (T-2), (T-4), (T-7), (T-8), (T-10) and (T-11) are preferable, in the case of importance of improvement effect of VHR (T-2), (T-4) and (T-11) are preferable, and in the case of importance of balance thereof, (T-2), (T-4), (T-10) and (T-11) are more preferable.
M y2 is particularly preferably a group represented by the following formula (T-4-1) or formula (T-4-2) from the viewpoints of easiness in obtaining raw materials and easiness in synthesizing.
[ Chemical 4]
(Wherein the bond is bonded to any one of S y3、Zy1 and Z y2, respectively).
In addition, from the viewpoints of easiness of acquisition of raw materials and easiness of synthesis, M y1 and M y3 each independently preferably represent 1, 4-phenylene, 1, 4-cyclohexylene or naphthalene-2, 6-diyl which is unsubstituted or may be substituted with 1 or more L y1, each independently more preferably represent a group selected from the following formulae (A-1) to (A-11),
[ Chemical 5]
Further preferably each independently represents a group selected from the group consisting of the formulae (A-1) to (A-8), and particularly preferably each independently represents a group selected from the group consisting of the formulae (A-1) to (A-4).
L y1 preferably represents P y2-Sy2 -, a halogen atom, a cyano group, a nitro group, a straight chain or branched alkyl group having 1 to 30 carbon atoms or a structure represented by the general formula (Y), wherein a hydrogen atom in the alkyl group may be substituted by a halogen atom, a cyano group, a nitro group, P y2-Sy2 -or a structure represented by the general formula (Y), the-CH 2 -in the alkyl group may be substituted by-CH=CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-in which more than 2-O-are not consecutive to cause adjacency), more preferably P y2-Sy2 -, a fluorine atom, a chlorine atom, a cyano group, a straight-chain or branched alkyl group having 1 to 12 carbon atoms or a structure represented by the general formula (Y), the hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom, a cyano group, P y2-Sy2 -or a structure represented by the general formula (Y), the-CH 2 -groups in the alkyl groups may be substituted by-CH=CH-, -COO-, -OCO-, -O-or-S-groups (more than 2-O-groups are not consecutive and result in adjacent groups), further preferably represents P y2-Sy2 -, a fluorine atom, a chlorine atom, a straight or branched alkyl group having 1 to 6 carbon atoms or a structure represented by the general formula (Y), wherein a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom, P y2-Sy2 -or a structure represented by the general formula (Y), -CH 2 -in the alkyl group may be substituted by-ch=ch-; -COO- -OCO-or-O-substitution (more than 2-O-will not be contiguous resulting in adjacency).
M and n each independently preferably represent an integer of 0 to 4, more preferably an integer of 0 to 3, and still more preferably an integer of 0 to 2. Among them, from the viewpoints of solubility in the composition and volatility in the production of a liquid crystal display element, the total number of m+n is preferably 0 to 6, more preferably 0 to 4, and still more preferably 1 to 3.
P y1 and P y2 each preferably independently represent a substituent selected from the group represented by the formula (P-1) to the formula (P-14),
[ Chemical 6]
(Wherein the black dots represent bond with S y1 or S y2), more preferably (P-1), (P-2), (P-4), (P-5), (P-7), (P-9), (P-11), (P-12) and (P-13), still more preferably (P-1), (P-2), (P-7), (P-12) and (P-13).
Wherein the total number of P y1 and P y2 contained in the structure represented by the general formula (Y-1) is preferably at least 1, more preferably at least 2. The total number of P y1 and P y2 contained in the structure represented by the general formula (Y-1) is preferably 1 to 4, more preferably 2 to 4, and still more preferably 2 to 3. In particular, when the total number of P y1 and P y2 is 2 to 3, the polymer obtained by polymerization is a crosslinked polymer, and thus the polymer is preferable because the steric structure is stable and the tilt stability is improved.
As the structure represented by the general formula (Y-1), the following formula (Y-1-A1) is preferable.
[ Chemical 7]
(Wherein X y1a represents CR y3a or a nitrogen atom, R y3a represents a group selected from the group consisting of a hydrogen atom, P y1a-Sy1a -or a linear or branched alkyl group having 1 to 12 carbon atoms, the hydrogen atom in the alkyl group being substituted with a halogen atom, the-CH 2 -in the alkyl group being substituted with-CH=CH-, -O-, -COO-, -OCO-or-OCOO-but not,
X y2a and X y3a are each independently a single bond or an alkylene group having 1 to 6 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a fluorine atom, a chlorine atom or a cyano group, the-CH 2 -group in the alkylene group may be represented by-CH=CH-, -CO-, -COO-, -OCO-, -OCOO-, -O-or-S-substitution but more than 2-O-are not consecutive resulting in adjacency,
R y1a and R y2a each independently represent a group selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, P y2a-Sy2a -, a linear or branched alkyl group having 1 to 12 carbon atoms, and a structure represented by the general formula (Y), the hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom, a cyano group, P y2-Sy2 -or a structure represented by the general formula (Y), the-CH 2 -group in the alkyl group may be replaced by-CH=CH-, -CO-, -COO-, -OCO-, O-or-S-substitution but more than 2-O-are not consecutive resulting in abutment,
S y3a is a single bond or a straight-chain or branched alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with P y2a-Sy2a -, a fluorine atom, a chlorine atom or a cyano group, the-CH 2 -group in the alkylene group may be represented by-CH=CH-, -CO-, -COO-, -OCO-, O-or-S-substitution but more than 2-O-are not consecutive resulting in abutment,
P y1a and P y2a each independently represent a substituent selected from the group represented by the formula (P-1) to the formula (P-14),
[ Chemical 8]
(Wherein, the black dot represents a bond with S y1a or S y2a),
S y1a and S y2a are a single bond or a straight-chain or branched alkylene group having 1 to 8 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a fluorine atom, a chlorine atom or a cyano group, the-CH 2 -group in the alkylene group may be represented by-CH=CH-, -CO-, -COO-, -OCO-, O-or-S-substitution but more than 2-O-are not consecutive resulting in abutment,
Z y1a and Z y2a each independently represent a single bond 、-C2H4-、-C4H8-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCOOCH2-、-CH2OCOO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2- or-C.ident.C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),
M y1a、My2a and M y3a each independently represent a group selected from the group consisting of the following formulas (T-1) to (T-21),
[ Chemical 9]
(Wherein, any of-CH=may be substituted with-N=independently of each other, and a bond may be present at any position, -CH 2 -each independently of the others may be represented by-O-, -S-, -NR 0 - (wherein, R 0 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), -CS-or-CO-substitution, but does not include an-O-O-bond), hydrogen atoms in these ring structures may be substituted with L y1a, L y1a represents P y2a-Sy2a -, a fluorine atom, a chlorine atom, a cyano group, a straight-chain or branched alkyl group having 1 to 30 carbon atoms or a structure represented by the general formula (Y), wherein a hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom, P y2-Sy2 -or a cyano group, the-CH 2 -groups in the alkyl groups may be substituted by-CH=CH-, -CO-, -COO-, -OCO-, -O-or-S-but more than 2-O-groups may not be consecutive to cause adjacency, in the case where there are a plurality of L y1a, they may be the same or different,
M a and n a each independently represent an integer of 0 to 3, wherein the total number of m+n is 0 to 4,
Wherein the total number of P y1a and P y2a contained in the structure represented by the general formula (Y-1) is at least 1. )
As the structure represented by the general formula (Y-1), the following formulas (Y-1-A2) and (Y-1-A3) are more preferable.
[ Chemical 10]
[ Chemical 11]
(Wherein ,Xy1a、Xy2a、Xy3a、Ry2a、Sy2a、Sy3a、Py2a、Zy1a、Zy2a、My1a、My2a、My3a、ma and n a represent the same meanings as those of Xy1a、Xy2a、Xy3a、Ry2a、Sy2a、Sy3a、Py2a、Zy1a、Zy2a、My1a、My2a、My3a、ma and n a in the formula (Y-1-A1))
In particular, in the structure represented by the formula (Y-1-A3), since the polymer groups are located at both ends of the ring structure, the rigidity of the crosslinked polymer obtained by polymerization is increased and the tilt stability is improved, which is preferable.
As the structure represented by the general formula (Y-1), the following formulas (Y-1-B1) and (Y-1-B2) are more preferable.
[ Chemical 12]
[ Chemical 13]
(Wherein X y1b represents CR y3b or a nitrogen atom, R y3b represents a group selected from the group consisting of a hydrogen atom, P y1b-Sy1b -and a linear or branched alkyl group having 1 to 6 carbon atoms, the-CH 2 -group in the alkyl group may be replaced by-O-; -COO-or-OCO-substitution but-O-discontinuity,
X y2b is a straight-chain alkylene group having 1 to 3 carbon atoms,
R y2b each independently represents a hydrogen atom, a halogen atom, a cyano group, or a straight-chain or branched alkyl group having 1 to 6 carbon atoms, the-CH 2 -group in the alkyl group may be replaced by-COO-, OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
S y3b is a single bond or a straight-chain or branched alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with P y2b-Sy2b -or a fluorine atom, the alkylene group may be represented by-CH 2 -COO-; OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
P y1b and P y2b each independently represent formula (P-1) or formula (P-2),
[ Chemical 14]
(Wherein, the black dot represents a bond with S y1b or S y2b),
S y1b and S y2b are a single bond or a straight chain alkylene group having 1 to 6 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a fluorine atom, the alkylene group may be represented by-CH 2 -COO-; OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
Z y1b and Z y2b each independently represent a single bond 、-C2H4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-、-CF2O-、-OCF2-、 or-C≡C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms), M y2b is a group represented by the formula (T-4-1) or the formula (T-4-2),
[ 15]
(Wherein the bond is bonded to either one of S y3b、Zy1b and Z y2b,
M y1b and M y3b each independently represent a group selected from the following formulae (A-1) to (A-8),
[ 16]
L y1b represents P y2b-Sy2b -, a fluorine atom, a chlorine atom, a cyano group, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, the-CH 2 -group in the alkyl group may be replaced by-COO-, OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
M b and n b each independently represent an integer of 0 to 2, wherein the sum of m+n is 0 to 2,
Wherein the total number of P y1b and P y2b contained in the structure represented by the formula (Y-1-B1) or the formula (Y-1-B2) is 1 to 3. )
The structure represented by the general formula (Y-1) is more preferably represented by the following formulas (Y-1-B3) to (Y-1-B6).
[ Chemical 17]
(Wherein S y3b、Sy2b、Zy1b、Zy2b、My1b、My3b、mb and n b each represent the same meaning as S y3b、Sy2b、Zy1b、Zy2b、My1b、My3b、mb and n b in the formula (Y-1-B1) or the formula (Y-1-B2))
The polymerizable compound represented by the general formula (Y-1) preferably has a polymerizable group in S y3b. This is because the structure represented by the general formula (Y) is located close to the polymer group, so that a crosslinked polymer can be formed at a position close to the substrate surface, and the VHR-elevating effect can be further improved.
The polymerizable compounds represented by the general formula (Y-1) according to the present invention are particularly preferably compounds represented by the general formulae (Y-1-1) to (Y-12-10). Among the compounds represented by the general formulae (Y-1-1) to (Y-12-10), the general formulae (Y-1-1) to (Y-9-10) are preferable.
[ Chemical 18]
[ Chemical 19]
[ Chemical 20]
[ Chemical 21]
[ Chemical 22]
[ Chemical 23]
[ Chemical 24]
[ Chemical 25]
[ Chemical 26]
[ Chemical 27]
[ Chemical 1]
[ Chemical 29]
[ Chemical 30]
[ 31]
In the following, when the content in the liquid crystal composition of the present invention is denoted by "%", the content is expressed by weight% unless otherwise noted.
In the liquid crystal composition of the present invention, the lower limit of the content of the compound having the structure represented by the general formula (Y) in the molecule is preferably 0.01 mass%, preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.04 mass%, preferably 0.05 mass%, preferably 0.06 mass%, preferably 0.07 mass%, preferably 0.08 mass%, preferably 0.09 mass%, preferably 0.1 mass%, preferably 0.12 mass%, preferably 0.15 mass%, preferably 0.17 mass%, preferably 0.2 mass%, preferably 0.22 mass%, preferably 0.25 mass%, preferably 0.27 mass%, preferably 0.3 mass%, preferably 0.32 mass%, preferably 0.35 mass%, preferably 0.37 mass%, preferably 0.4 mass%, preferably 0.42 mass%, preferably 0.45 mass%, preferably 0.5 mass%, preferably 0.55 mass%.
In the liquid crystal composition of the present invention, the upper limit of the content of the compound having the structure represented by the general formula (Y) in the molecule is preferably 5% by mass, preferably 4.5% by mass, preferably 4% by mass, preferably 3.5% by mass, preferably 3% by mass, preferably 2.5% by mass, preferably 2% by mass, preferably 1% by mass, preferably 0.95% by mass, preferably 0.9% by mass, preferably 0.85% by mass, preferably 0.8% by mass, preferably 0.75% by mass, preferably 0.7% by mass, preferably 0.65% by mass, preferably 0.6% by mass, preferably 0.55% by mass, preferably 0.5% by mass, preferably 0.45% by mass, preferably 0.4% by mass.
To describe in further detail, in order to obtain a sufficient pretilt angle or a small residual amount of the polymerizable compound or a high Voltage Holding Ratio (VHR), the content thereof is preferably 0.2 to 1.5 mass%, and in the case where suppression of precipitation at low temperature is important, the content thereof is preferably 0.01 to 1.0 mass%. In the case of containing a plurality of compounds each having a structure represented by the general formula (Y) in the molecule, the content of each is preferably 0.01 to 0.6 mass%. Therefore, in order to solve all the problems, it is particularly desirable to adjust the compound having a structure represented by the general formula (Y) in the molecule within a range of 0.1 to 1.0 mass%, and it is particularly preferable to adjust the compound within a range of 0.1 to 0.5 mass% from the viewpoint of low-temperature storage property.
The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (L). The compound represented by the general formula (L) corresponds to a compound having substantially neutral dielectric properties (the value of Deltaε is-2 to 2). Therefore, the number of polar groups such as halogen contained in the molecule is preferably 2 or less, more preferably 1 or less, and preferably none.
[ Chemical 32]
(Wherein R L1 and R L2 each independently represent an alkyl group having 1 to 8 carbon atoms, 1 or non-adjacent 2 or more-CH 2 -groups in the alkyl group may each independently be substituted by-CH=CH-, -C≡C-, -O-, -CO-, -COO-, or-OCO-,
N L1 represents 0, 1, 2 or 3,
A L1、AL2 and a L3 each independently represent a group selected from the group consisting of:
(a) 1, 4-Cyclohexylene (1-CH 2 -or present in this group) non-adjacent 2 or more-CH 2 -which may be substituted with-O-)) and
(B) 1, 4-phenylene (1-ch=or non-adjacent 2 or more-ch=present in the group may be substituted with-n=)
(C) Naphthalene-1, 4-diyl, naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-ch=or non-adjacent 2 or more-ch=present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-n=)
The above-mentioned group (a), group (b) and group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
Z L1 and Z L2 each independently represent a single bond 、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCF2-、-CF2O-、-CH＝N-N＝CH-、-CH＝CH-、-CF＝CF- or-C.ident.C-,
Where N L1 is 2 or 3 and a plurality of A L2 are present, they may be the same or different, and where N L1 is 2 or 3 and a plurality of Z L2 are present, they may be the same or different, but do not include the compounds represented by the general formulae (N-1), (N-2) and (N-3). )
The compounds represented by the general formula (L) may be used alone or in combination. The types of the combinable compounds are not particularly limited, and are suitably used in combination in accordance with desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound used is, for example, 1 in one embodiment of the present invention. Or 2,3, 4, 5, 6, 7, 8, 9, 10 or more in other embodiments of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, etc.
The lower limit of the preferable content of the compound represented by the formula (L) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.
In the case of a composition in which the viscosity of the composition of the present invention is kept low and a high response speed is required, it is preferable that the lower limit value and the upper limit value are high. Further, in the case of a composition in which Tni of the composition of the present invention is kept high and a good temperature stability is required, it is preferable that the lower limit value and the upper limit value are high. In order to keep the drive voltage low and to increase the dielectric anisotropy, the lower limit value and the upper limit value are preferably low.
In the case where reliability is important, R L1 and R L2 are preferably both alkyl groups. In the case where importance is attached to reducing the volatility of the compound, an alkoxy group is preferable, and in the case where importance is attached to reducing the tackiness, at least one of the alkenyl groups is preferable.
The number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3, preferably 0 or 1, and in the case of paying attention to compatibility with other liquid crystal molecules, preferably 1.
R L1 and R L2 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 4 to 5 carbon atoms when the ring structure to which they are bonded is phenyl (aromatic), and cyclohexane, pyran or two groups when the ring structure to which they are bonded isIn the case of a saturated ring structure such as an alkane, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.
The alkenyl group is preferably a group represented by any one selected from the formulae (R1) to (R5). (the black dots in the formulae represent carbon atoms in the ring structure.)
[ 33]
N L1 is preferably 0 when importance is attached to the response speed, and is preferably 2 or 3 in order to improve the upper limit temperature of the nematic phase, and is preferably 1 in order to achieve the balance. In addition, in order to satisfy the characteristics required as a composition, it is preferable to combine compounds of different values.
A L1、AL2 and A L3 are preferably aromatic in the case where an increase in Δn is required, and are preferably aliphatic for improving the response speed, and each independently preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2] octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decalin-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represents the structure,
[ Chemical 34]
More preferably trans-1, 4-cyclohexylene or 1, 4-phenylene.
Z L1 and Z L2 are preferably single bonds in the case where the response speed is important.
The compound represented by the general formula (L) preferably has 0 or 1 halogen atoms in the molecule.
The compound represented by the general formula (L) is preferably a compound selected from the group of compounds represented by the general formulae (L-1) to (L-8).
The compound represented by the general formula (L-1) is the following compound.
[ 35]
(Wherein R L11 and R L12 each independently represent the same meaning as R L1 and R L2 in the general formula (L))
R L11 and R L12 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or a linear alkenyl group having 2 to 5 carbon atoms.
The compound represented by the general formula (L-1) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
The lower limit of the content is preferably 1%, 2%, 3%, 5%, 7%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25% with respect to the total amount of the composition of the present invention.
In the case of a composition in which the viscosity of the composition of the present invention is kept low and a high response speed is required, it is preferable that the lower limit value and the upper limit value are high. Further, in the case of a composition in which Tni of the composition of the present invention is kept high and a good temperature stability is required, the lower limit value and the upper limit value are preferably equal. In order to keep the drive voltage low and to increase the dielectric anisotropy, the lower limit value and the upper limit value are preferably low.
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-1).
[ 36]
(Wherein R L12 represents the same meaning as in the general formula (L-1))
The compound represented by the general formula (L-1-1) is preferably a compound selected from the group of compounds represented by the formulas (L-1-1.1) to (L-1-1.3), preferably a compound represented by the formula (L-1-1.2) or (L-1-1.3), and particularly preferably a compound represented by the formula (L-1-1.3).
[ 37]
The lower limit of the preferable content of the compound represented by the formula (L-1-1.3) is 1%, 2%, 3%, 5%, 7%, 10% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-2).
[ 38]
(Wherein R L12 represents the same meaning as in the general formula (L-1))
The lower limit of the preferable content of the compound represented by the formula (L-1-2) is 1%, 5%, 10%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 35% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (L-1-2) is preferably a compound selected from the group of compounds represented by the formulas (L-1-2.1) to (L-1-2.4), and preferably a compound represented by the formulas (L-1-2.2) to (L-1-2.4). In particular, the compound represented by the formula (L-1-2.2) is preferable because it improves the response speed of the composition of the present invention. In the case where Tni is required to be higher than the response speed, the compound represented by the formula (L-1-2.3) or the formula (L-1-2.4) is preferably used. In order to improve the solubility at low temperatures, the content of the compounds represented by the formulae (L-1-2.3) and (L-1-2.4) is not preferably 30% or more.
[ 39]
The lower limit of the preferable content of the compound represented by the formula (L-1-2.2) is 10%, 15%, 18%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 38%, 40% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 43%, 40%, 38%, 35%, 32%, 30%, 27%, 25%, 22% with respect to the total amount of the composition of the present invention.
The lower limit value of the total preferable content of the compound represented by the formula (L-1-1.3) and the compound represented by the formula (L-1-2.2) is 10%, 15%, 20%, 25%, 27%, 30%, 35%, 40% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 43%, 40%, 38%, 35%, 32%, 30%, 27%, 25%, 22% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-3).
[ 40]
(Wherein R L13 and R L14 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
R L13 and R L14 are preferably linear alkyl groups having 1 to 5 carbon atoms or linear alkoxy groups having 1 to 4 carbon atoms.
The lower limit of the preferable content of the compound represented by the formula (L-1-3) is 1%, 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 30% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, 10% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (L-1-3) is preferably a compound selected from the group of compounds represented by the formulas (L-1-3.1) to (L-1-3.13), preferably a compound represented by the formula (L-1-3.1), the formula (L-1-3.3) or the formula (L-1-3.4). In particular, the compound represented by the formula (L-1-3.1) is preferable because it improves the response speed of the composition of the present invention. In the case where Tni is required to be higher than the response speed, the compounds represented by the formulae (L-1-3.3), (L-1-3.4), (L-1-3.11) and (L-1-3.13) are preferably used. In order to improve the solubility at low temperatures, the total content of the compounds represented by the formulas (L-1-3.3), (L-1-3.4), (L-1-3.11) and (L-1-3.13) is not preferably 20% or more.
[ Chemical 41]
The lower limit of the preferable content of the compound represented by the formula (L-1-3.1) is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 17%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formulae (L-1-4) and/or (L-1-5).
[ Chemical 42]
(Wherein R L15 and R L16 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
R L15 and R L16 are preferably linear alkyl groups having 1 to 5 carbon atoms or linear alkoxy groups having 1 to 4 carbon atoms.
The lower limit of the preferable content of the compound represented by the formula (L-1-4) is 1%, 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total amount of the composition of the present invention.
The lower limit of the preferable content of the compound represented by the formula (L-1-5) is 1%, 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total amount of the composition of the present invention.
Further, the compounds represented by the general formulae (L-1-4) and (L-1-5) are preferably compounds selected from the group of compounds represented by the formulae (L-1-4.1) to (L-1-5.3), and preferably compounds represented by the formulae (L-1-4.2) or (L-1-5.2).
[ Chemical 43]
The lower limit of the preferable content of the compound represented by the formula (L-1-4.2) is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 17%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the composition of the present invention.
Preferably, the combination of 2 or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3), (L-1-2.2), (L-1-3.1), (L-1-3.3), (L-1-3.4), (L-1-3.11) and (L-1-3.12), and the combination of 2 or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3), (L-1-2.2), the compounds represented by the formulae (L-1-3.1), the formulae (L-1-3.4) and (L-1-4.2) is preferably such that the lower limit of the total content of these compounds is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, and the upper limit of the total content of these compounds is preferably 80%, 70%, 60%, 45%, 25%, 30%, 35%, 25%, 30% and 30% of the total content of these compounds represented by the total amount of the compositions of the invention. In the case where the reliability of the composition is important, it is preferable to combine 2 or more compounds selected from the compounds represented by the formulas (L-1-3.1), (L-1-3.3) and (L-1-3.4), and in the case where the response speed of the composition is important, it is preferable to combine 2 or more compounds selected from the compounds represented by the formulas (L-1-1.3) and (L-1-2.2).
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-6).
[ 44]
(Wherein R L17 and R L18 each independently represent a methyl group or a hydrogen atom.)
The lower limit of the preferable content of the compound represented by the formula (L-1-6) is 1%, 5%, 10%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 35% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (L-1-6) is preferably a compound selected from the group of compounds represented by the formulas (L-1-6.1) to (L-1-6.3).
[ 45]
The compound represented by the general formula (L-2) is the following compound.
[ Chemical 46]
(Wherein R L21 and R L22 each independently represent the same meaning as R L1 and R L2 in the general formula (L))
R L21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R L22 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The compound represented by the general formula (L-2) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
When the solubility at low temperature is emphasized, the effect is good when the content is set to be high, whereas when the response speed is emphasized, the effect is good when the content is set to be low. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (L-2) is 1%, 2%, 3%, 5%, 7% and 10% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (L-2) is preferably a compound selected from the group of compounds represented by the formulas (L-2.1) to (L-2.6), and preferably a compound represented by the formulas (L-2.1), (L-2.3), (L-2.4) and (L-2.6).
[ 47]
The compound represented by the general formula (L-3) is the following compound.
[ 48]
(Wherein R L31 and R L32 each independently represent the same meaning as R L1 and R L2 in the general formula (L))
R L31 and R L32 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The compound represented by the general formula (L-3) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
The lower limit of the preferable content of the compound represented by the formula (L-3) is 1%, 2%, 3%, 5%, 7% and 10% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
When a high birefringence is obtained, the effect is good when the content is set to be high, whereas when a high Tni is emphasized, the effect is good when the content is set to be low. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
Further, the compound represented by the general formula (L-3) is preferably a compound selected from the group of compounds represented by the formulas (L-3.1) to (L-3.7), and preferably a compound represented by the formulas (L-3.2) to (L-3.5).
[ 49]
The compound represented by the general formula (L-4) is the following compound.
[ 50]
(Wherein R L41 and R L42 each independently represent the same meaning as R L1 and R L2 in the general formula (L))
R L41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R L42 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. )
The compound represented by the general formula (L-4) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L-4) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, etc.
The lower limit of the preferable content of the compound represented by the formula (L-4) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% relative to the total amount of the composition of the present invention. The preferable upper limit value of the content of the compound represented by the formula (L-4) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% relative to the total amount of the composition of the present invention.
The compounds represented by the general formula (L-4) are preferably, for example, compounds represented by the formulae (L-4.1) to (L-4.3).
[ 51]
The compound represented by the formula (L-4.1) may be contained, the compound represented by the formula (L-4.2) may be contained, both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) may be contained, and the compounds represented by the formulae (L-4.1) to (L-4.3) may be contained, depending on the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The preferable lower limit value of the content of the compound represented by the formula (L-4.1) or the formula (L-4.2) is 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, 21%, and the preferable upper limit value is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8% relative to the total amount of the composition of the present invention.
When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, the preferable lower limit values of the two compounds are 15%, 19%, 24%, 30%, and the preferable upper limit values are 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-4) is preferably, for example, a compound represented by the formulae (L-4.4) to (L-4.6), and more preferably a compound represented by the formula (L-4.4).
[ 52]
The compound represented by the formula (L-4.4) may be contained, or the compound represented by the formula (L-4.5) may be contained, or both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) may be contained, depending on the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence.
The preferable lower limit of the content of the compound represented by the formula (L-4.4) or the formula (L-4.5) is 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, 21% relative to the total amount of the composition of the present invention. The upper limit is preferably 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%.
When both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, the preferable lower limit values of the two compounds are 15%, 19%, 24%, 30%, and the preferable upper limit values are 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-4) is preferably a compound represented by the formulae (L-4.7) to (L-4.10), and particularly preferably a compound represented by the formula (L-4.9).
[ 53]
The compound represented by the general formula (L-5) is the following compound.
[ 54]
(Wherein R L51 and R L52 each independently represent the same meaning as R L1 and R L2 in the general formula (L))
R L51 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R L52 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The compound represented by the general formula (L-5) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L-5) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, etc.
The lower limit of the preferable content of the compound represented by the formula (L-5) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% relative to the total amount of the composition of the present invention. The preferable upper limit of the content of the compound represented by the formula (L-5) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% relative to the total amount of the composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and particularly preferably a compound represented by the formula (L-5.1).
The preferred lower limits of the content of these compounds relative to the total amount of the composition of the invention are 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
[ 55]
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).
The preferred lower limits of the content of these compounds relative to the total amount of the composition of the invention are 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
[ 56]
The compound represented by the general formula (L-5) is preferably a compound selected from the group of compounds represented by the formulas (L-5.5) to (L-5.7), and particularly preferably a compound represented by the formula (L-5.7).
The preferred lower limits of the content of these compounds relative to the total amount of the composition of the invention are 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
[ 57]
The compound represented by the general formula (L-6) is the following compound.
[ 58]
(Wherein R L61 and R L62 each independently represent the same meaning as R L1 and R L2 in the general formula (L), and X L61 and X L62 each independently represent a hydrogen atom or a fluorine atom.)
R L61 and R L62 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and one of X L61 and X L62 is preferably a fluorine atom and the other is preferably a hydrogen atom.
The compound represented by the general formula (L-6) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
The lower limit of the preferable content of the compound represented by the formula (L-6) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% relative to the total amount of the composition of the present invention. The preferable upper limit of the content of the compound represented by the formula (L-6) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% relative to the total amount of the composition of the present invention. When the concentration is increased by Δn, the content is preferably increased, and when the concentration is precipitated at a low temperature, the content is preferably decreased.
The compounds represented by the general formula (L-6) are preferably compounds represented by the formulae (L-6.1) to (L-6.9).
[ 59]
The types of the combinable compounds are not particularly limited, but 1 to 3 of these compounds are preferably contained, and 1 to 4 are more preferably contained. Further, since the molecular weight distribution of the selected compound is also effective for solubility, for example, 1 compound is preferably selected from the compounds represented by the formula (L-6.1) or (L-6.2), 1 compound is preferably selected from the compounds represented by the formula (L-6.4) or (L-6.5), 1 compound is preferably selected from the compounds represented by the formula (L-6.6) or (L-6.7), and 1 compound is preferably selected from the compounds represented by the formula (L-6.8) or (L-6.9), and these are suitably combined. Among them, the compounds represented by the formula (L-6.1), the formula (L-6.3), the formula (L-6.4), the formula (L-6.6) and the formula (L-6.9) are preferably contained.
Further, the compound represented by the general formula (L-6) is preferably, for example, a compound represented by the formulae (L-6.10) to (L-6.17), and among them, a compound represented by the formula (L-6.11) is preferable.
[ Chemical 60]
The preferred lower limits of the content of these compounds relative to the total amount of the composition of the invention are 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
The compound represented by the general formula (L-7) is the following compound.
[ Chemical 61]
(Wherein R L71 and R L72 each independently represent the same meaning as R L1 and R L2 in the general formula (L), A L71 and A L72 each independently represent the same meaning as A L2 and A L3 in the general formula (L), but a hydrogen atom on A L71 and A L72 each independently may be substituted with a fluorine atom, Z L71 represents the same meaning as Z L2 in the general formula (L), and X L71 and X L72 each independently represent a fluorine atom or a hydrogen atom.)
Wherein R L71 and R L72 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, A L71 and A L72 are each independently preferably a1, 4-cyclohexylene group or a1, 4-phenylene group, the hydrogen atoms on A L71 and A L72 may each independently be substituted with a fluorine atom, Z L71 is preferably a single bond or-COO-, preferably a single bond, and X L71 and X L72 are preferably hydrogen atoms.
The types of the compounds to be combined are not particularly limited, and they are combined according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of the compounds used are, for example, 1,2,3,4 in one embodiment of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L-7) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, etc.
The lower limit of the preferable content of the compound represented by the formula (L-7) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20% relative to the total amount of the composition of the present invention. The preferable upper limit of the content of the compound represented by the formula (L-7) is 30%, 25%, 23%, 20%, 18%, 15%, 10%, 5% relative to the total amount of the composition of the present invention.
In the case where the composition of the present invention is desired to be an embodiment with a high Tni, the content of the compound represented by the formula (L-7) is preferably made large, and in the case where the composition is desired to be an embodiment with a low viscosity, the content is preferably made small.
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.1) to (L-7.4), and more preferably a compound represented by the formula (L-7.2).
[ 62]
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.11) to (L-7.13), and more preferably a compound represented by the formula (L-7.11).
[ 63]
Further, the compounds represented by the general formula (L-7) are compounds represented by the formulae (L-7.21) to (L-7.23). The compound represented by the formula (L-7.21) is preferable.
[ 64]
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.31) to (L-7.34), and more preferably a compound represented by the formulae (L-7.31) or/and (L-7.32).
[ 65]
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.41) to (L-7.44), and more preferably a compound represented by the formulae (L-7.41) or/and (L-7.42).
[ Chemical 66]
Further, the compounds represented by the general formula (L-7) are preferably compounds represented by the formulae (L-7.51) to (L-7.53).
[ 67]
The compound represented by the general formula (L-8) is the following compound.
[ Chemical 68]
(Wherein R L71 and R L72 each independently represent the same meaning as R L1 and R L2 in the general formula (L), A L71 and A L72 each independently represent the same meaning as A L2 and A L3 in the general formula (L), but a hydrogen atom on A L71 and A L72 each independently may be substituted with a fluorine atom, Z L71 represents the same meaning as Z L2 in the general formula (L), and X L71 and X L72 each independently represent a fluorine atom or a hydrogen atom.)
Wherein R L71 and R L72 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, A L71 and A L72 are each independently preferably a1, 4-cyclohexylene group or a1, 4-phenylene group, the hydrogen atoms on A L71 and A L72 may each independently be substituted with a fluorine atom, Z L71 is preferably a single bond or-COO-, preferably a single bond, and X L71 and X L72 are preferably hydrogen atoms.
The types of the compounds to be combined are not particularly limited, and they are combined according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of the compounds used are, for example, 1,2,3,4 in one embodiment of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L-7) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, etc.
The lower limit of the preferable content of the compound represented by the formula (L-7) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20% relative to the total amount of the composition of the present invention. The preferable upper limit of the content of the compound represented by the formula (L-7) is 30%, 25%, 23%, 20%, 18%, 15%, 10%, 5% relative to the total amount of the composition of the present invention.
In the case where the composition of the present invention is desired to be an embodiment with a high Tni, the content of the compound represented by the formula (L-7) is preferably made large, and in the case where the composition is desired to be an embodiment with a low viscosity, the content is preferably made small.
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.1) to (L-7.4), and more preferably a compound represented by the formula (L-7.2).
[ 69]
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.11) to (L-7.13), and more preferably a compound represented by the formula (L-7.11).
[ 70]
Further, the compounds represented by the general formula (L-7) are compounds represented by the formulae (L-7.21) to (L-7.23). The compound represented by the formula (L-7.21) is preferable.
[ Chemical 71]
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.31) to (L-7.34), and more preferably a compound represented by the formulae (L-7.31) or/and (L-7.32).
[ Chemical 72]
Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.41) to (L-7.44), and more preferably a compound represented by the formulae (L-7.41) or/and (L-7.42).
[ 73]
Further, the compounds represented by the general formula (L-7) are preferably compounds represented by the formulae (L-7.51) to (L-7.53).
[ Chemical 74]
The composition of the present invention preferably contains 1 or 2 or more compounds selected from the compounds represented by the general formulae (N-1), (N-2) and (N-3). These compounds correspond to compounds having negative dielectric properties (the sign of Δε is negative and the absolute value is greater than 2.).
[ 75]
(Wherein R N11、RN12、RN21、RN22、RN31 and R N32 each independently represent an alkyl group having 1 to 8 carbon atoms, 1 or non-adjacent 2 or more-CH 2 -groups in the alkyl group may each independently be substituted by-CH=CH-, -C≡C-, -O-, -CO-, -COO-, or-OCO-,
A N11、AN12、AN21、AN22、AN31 and a N32 each independently represent a group selected from the group consisting of:
(a) 1, 4-Cyclohexylene (1-CH 2 -or present in this group) non-adjacent 2 or more-CH 2 -which may be substituted with-O-)
(B) 1, 4-phenylene (1-ch=or non-adjacent 2 or more-ch=present in the group may be substituted with-n=)
(C) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-ch=or non-adjacent 2 or more-ch=groups present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted with-n=) and
(D) 1, 4-cyclohexenylene
The above-mentioned group (a), group (b), group (c) and group (d) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
Z N11、ZN12、ZN21、ZN22、ZN31 and Z N32 each independently represent a single bond 、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCF2-、-CF2O-、-CH＝N-N＝CH-、-CH＝CH-、-CF＝CF- or-C.ident.C-,
X N21 represents a hydrogen atom or a fluorine atom,
T N31 represents-CH 2 -or an oxygen atom,
N N11、nN12、nN21、nN22、nN31 and n N32 each independently represent an integer of 0 to 3, but n N11+nN12、nN21+nN22 and n N31+nN32 each independently represent 1,2 or 3, and in the case where a N11～AN32、ZN11～ZN32 is present in plural, they may be the same or different. )
The compounds represented by the general formulae (N-1), (N-2) and (N-3) are preferably those having a negative Δε and an absolute value of more than 3.
In the general formulae (N-1), (N-2) and (N-3), R N11、RN12、RN21、RN22、RN31 and R N32 are each independently preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, particularly preferably an alkenyl group (propenyl group) having 3 carbon atoms.
Further, when the ring structure to which the compound is bonded is phenyl (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 4 to 5 carbon atoms, and the ring structure to which the compound is bonded is cyclohexane, pyran or dioxaneIn the case of a saturated ring structure such as an alkane, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.
The alkenyl group is preferably a group represented by any one selected from the formulae (R1) to (R5). (the black dots in the formulae represent carbon atoms in the ring structure.)
[ Chemical 76]
A N11、AN12、AN21、AN22、AN31 and A N32 are each independently preferably aromatic in the case where an increase in Δn is required, and are preferably aliphatic for improving the response speed, and preferably represent trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2] octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represent the following structure,
[ Chemical 77]
More preferably trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene.
Z N11、ZN12、ZN21、ZN22、ZN31 and Z N32 each independently preferably represent-CH 2O-、-CF2O-、-CH2CH2-、-CF2CF2 -or a single bond, further preferred is-CH 2O-、-CH2CH2 -or a single bond, and particularly preferred is-CH 2 O-or a single bond.
X N21 is preferably a fluorine atom.
T N31 is preferably an oxygen atom.
Preferably, n N11+nN12、nN21+nN22 and n N31+nN32 are 1 or 2, preferably, a combination of n N11 of 1 and n N12 of 0, a combination of n N11 of 2 and n N12 of 0, a combination of n N11 of 1 and n N12 of 1, a combination of n N11 of 2 and n N12 of 1, a combination of n N21 of 1 and n N22 of 0, a combination of n N21 of 2 and n N22 of 0, a combination of n N31 of 1 and n N32 of 0, and a combination of n N31 of 2 and n N32 of 0.
The lower limit of the preferable content of the compound represented by the formula (N-1) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.
The lower limit of the preferable content of the compound represented by the formula (N-2) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.
The lower limit of the preferable content of the compound represented by the formula (N-3) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.
In the case of a composition in which the viscosity of the composition of the present invention is kept low and a high response speed is required, the lower limit value and the upper limit value are preferably low. Further, in the case of a composition in which Tni of the composition of the present invention is kept high and a good temperature stability is required, the lower limit value and the upper limit value are preferably low. In order to keep the drive voltage low and to increase the dielectric anisotropy, it is preferable that the lower limit value is high and the upper limit value is high.
The compounds represented by the general formula (N-1) include compounds represented by the following general formulae (N-1 a) to (N-1 g).
[ 78]
(Wherein R N11 and R N12 have the same meaning as R N11 and R N12 in the general formula (N-1), N Na11 represents 0 or 1, N Nb11 represents 1 or 2, N Nc11 represents 0 or 1, N Nd11 represents 1 or 2, N Ne11 represents 1 or 2, N Nf12 represents 1 or 2, N Ng11 represents 1 or 2, A Ne11 represents trans-1, 4-cyclohexylene or 1, 4-phenylene, A Ng11 represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene and at least 1 represents 1, 4-cyclohexenylene, Z Ne11 represents a single bond or ethylene and at least 1 present in the molecule represents ethylene, and a plurality of A Ne11、ZNe11 and/or A Ng11 present in the molecule may be the same or different.)
More specifically, the compound represented by the general formula (N-1) is preferably a compound selected from the group of compounds represented by the general formulae (N-1-1) to (N-1-22).
The compound represented by the general formula (N-1-1) is the following compound.
[ Chemical 79]
(Wherein R N111 and R N112 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably a propyl group, a pentyl group or a vinyl group. R N112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group or a butoxy group.
The compounds represented by the general formula (N-1-1) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be low. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-1) is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-1) is preferably a compound selected from the group of compounds represented by the formulas (N-1-1.1) to (N-1-1.25), preferably a compound represented by the formulas (N-1-1.1) to (N-1-1.4), preferably a compound represented by the formulas (N-1-1.1) and (N-1-1.3).
[ 80]
The compounds represented by the formulae (N-1-1.1) to (N-1-1.25) may be used singly or in combination, and the lower limit of the preferable content of each of these compounds is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% based on the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-2) is the following compound.
[ 81]
(Wherein R N121 and R N122 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl, butyl or pentyl. R N122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group.
The compounds represented by the general formula (N-1-2) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, when attention is paid to the solubility at low temperature, the effect is good when the content is set to be low, and when attention is paid to T NI, the effect is good when the content is set to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-2) is 5%, 7%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37%, 40%, 42% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 48%, 45%, 43%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-2) is preferably a compound selected from the group of compounds represented by the formulas (N-1-2.1) to (N-1-2.25), preferably a compound represented by the formulas (N-1-2.3) to (N-1-2.7), the formulas (N-1-2.10), the formulas (N-1-2.11), the formulas (N-1-2.13) and the formulas (N-1-2.20), and in the case of paying attention to improvement of Δε, preferably a compound represented by the formulas (N-1-2.3) to (N-1-2.7), in the case of improvement of T NI, preferably a compound represented by the formulas (N-1-2.10), the formulas (N-1-2.11) and the formulas (N-1-2.13), and in the case of paying attention to improvement of response speed, preferably a compound represented by the formulas (N-1-2.20).
[ Chemical 82]
The compounds represented by the formulae (N-1-2.1) to (N-1-2.25) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-3) is the following compound.
[ 83]
(Wherein R N131 and R N132 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl or butyl. R N132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably 1-propenyl, ethoxy, propoxy or butoxy.
The compounds represented by the general formula (N-1-3) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-3) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-3) is preferably a compound selected from the group of compounds represented by the formulas (N-1-3.1) to (N-1-3.21), preferably a compound represented by the formulas (N-1-3.1) to (N-1-3.7) and (N-1-3.21), preferably a compound represented by the formulas (N-1-3.1), (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) and formula (N-1-3.6).
[ Chemical 84]
The compounds represented by the formulae (N-1-3.1) to (N-1-3.4), (N-1-3.6) and (N-1-3.21) may be used alone or in combination, and preferably, the combination of the formulae (N-1-3.1) and (N-1-3.2) is selected from the group consisting of 2 or 3 of the formulae (N-1-3.3), the formulae (N-1-3.4) and (N-1-3.6). The lower limit of the preferred content of these compounds alone or in combination with the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-4) is the following compound.
[ Chemical 85]
(Wherein R N141 and R N142 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N141 and R N142 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and are preferably methyl, propyl, ethoxy or butoxy groups.
The compounds represented by the general formula (N-1-4) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be low. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-4) is 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, 10%, 8% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-4) is preferably a compound selected from the group of compounds represented by the formulas (N-1-4.1) to (N-1-4.24), preferably a compound represented by the formulas (N-1-4.1) to (N-1-4.4), preferably a compound represented by the formulas (N-1-4.1), formula (N-1-4.2) and formula (N-1-4.4).
[ 86]
The compounds represented by the formulae (N-1-4.1) to (N-1-4.24) may be used alone or in combination, and the lower limit of the preferable content of each of these compounds is 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20% based on the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, 10%, 8% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-5) is the following compound.
[ 87]
(Wherein R N151 and R N152 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N151 and R N152 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and are preferably ethyl, propyl or butyl.
The compounds represented by the general formula (N-1-5) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3,4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, when attention is paid to the solubility at low temperature, the effect is good when the content is set to be low, and when attention is paid to T NI, the effect is good when the content is set to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-5) is 5%, 8%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-5) is preferably a compound selected from the group of compounds represented by the formulas (N-1-5.1) to (N-1-5.12), and preferably a compound represented by the formulas (N-1-5.1), (N-1-5.2) and (N-1-5.4).
[ 88]
The compounds represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4) may be used singly or in combination, and the lower limit values of the preferable contents of these compounds are 5%, 8%, 10%, 13%, 15%, 17% and 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-10) is the following compound.
[ Chemical 89]
(Wherein R N1101 and R N1102 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl, butyl, vinyl or 1-propenyl. R N1102 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-10) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be low. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-10) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-10) is preferably a compound selected from the group of compounds represented by the formulas (N-1-10.1) to (N-1-10.14), preferably a compound represented by the formulas (N-1-10.1) to (N-1-10.5), preferably a compound represented by the formulas (N-1-10.1) and (N-1-10.2).
[ Chemical 90]
The compounds represented by the formulae (N-1-10.1) and (N-1-10.2) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-11) is the following compound.
[ 91]
(Wherein R N1111 and R N1112 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl, butyl, vinyl or 1-propenyl. R N1112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-11) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, when attention is paid to the solubility at low temperature, the effect is good when the content is set to be low, and when attention is paid to T NI, the effect is good when the content is set to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-11) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-11) is preferably a compound selected from the group of compounds represented by the formulas (N-1-11.1) to (N-1-11.14), preferably a compound represented by the formulas (N-1-11.2) and (N-1-11.4).
[ Chemical 92]
The compounds represented by the formulae (N-1-11.2) and (N-1-11.4) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-12) is the following compound.
[ 93]
(Wherein R N1121 and R N1122 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl or butyl. R N1122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-12) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be low. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-12) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-13) is the following compound.
[ 94]
(Wherein R N1131 and R N1132 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl or butyl. R N1132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-13) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-13) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-14) is the following compound.
[ 95]
(Wherein R N1141 and R N1142 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl or butyl. R N1142 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-14) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be low. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-14) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-15) is the following compound.
[ Chemical 96]
(Wherein R N1151 and R N1152 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1151 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl or butyl. R N1152 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-15) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-15) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-16) is the following compound.
[ 97]
(Wherein R N1161 and R N1162 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1161 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl or butyl. R N1162 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-16) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-16) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-17) is the following compound.
[ 98]
(Wherein R N1171 and R N1172 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1171 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably ethyl, propyl or butyl. R N1172 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-17) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-17) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-18) is the following compound.
[ Chemical 99]
(Wherein R N1181 and R N1182 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1181 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably methyl, ethyl, propyl or butyl. R N1182 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-18) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-18) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-18) is preferably a compound selected from the group of compounds represented by the formulas (N-1-18.1) to (N-1-18.5), preferably a compound represented by the formulas (N-1-18.1) to (N-1-18.3), preferably a compound represented by the formulas (N-1-18.2) and (N-1-18.3).
[ 100]
The compound represented by the general formula (N-1-20) is the following compound.
[ 101]
(Wherein R N1201 and R N1202 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1201 and R N1202 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and are preferably ethyl, propyl or butyl groups.
The compounds represented by the general formula (N-1-20) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-20) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-21) is the following compound.
[ Chemical 102]
(Wherein R N1211 and R N1212 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1211 and R N1212 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and are preferably ethyl, propyl or butyl groups.
The compounds represented by the general formula (N-1-21) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1, 2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-21) is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-22) is the following compound.
[ 103]
(Wherein R N1221 and R N1222 each independently represent the same meaning as R N11 and R N12 in the general formula (N-1))
R N1221 and R N1222 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and are preferably ethyl, propyl or butyl groups.
The compounds represented by the general formula (N-1-22) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, 3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-1-21) is 1%, 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 5% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-1-22) is preferably a compound selected from the group of compounds represented by the formulas (N-1-22.1) to (N-1-22.12), preferably a compound represented by the formulas (N-1-22.1) to (N-1-22.5), preferably a compound represented by the formulas (N-1-22.1) to (N-1-22.4).
[ Chemical 104]
The compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formula (N-3-2).
[ 105]
(Wherein R N321 and R N322 each independently represent the same meaning as R N11 and R N12 in the general formula (N-3))
R N321 and R N322 are preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and are preferably propyl or pentyl groups.
The compound represented by the general formula (N-3-2) may be used alone or in combination of 2 or more compounds. The types of the compounds to be combined are not particularly limited, and are suitably used in combination in accordance with the properties required for solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2,3, 4, 5 or more in one embodiment of the present invention.
When attention is paid to the improvement of Δε, it is preferable to set the content to be high, and when attention is paid to the solubility at low temperature, it is preferable to set the content to be high, and when attention is paid to T NI, it is preferable to set the content to be high. Further, in the case of improving the drop mark and burn-in characteristics, the content range is preferably set to be centered.
The lower limit of the preferable content of the compound represented by the formula (N-3-2) is 3%, 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5% with respect to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (N-3-2) is preferably a compound selected from the group of compounds represented by the formulas (N-3-2.1) to (N-3-2.3).
[ 106]
The composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (J). These compounds correspond to compounds having positive dielectric properties (Δε is greater than 2.).
[ Chemical 107]
(Wherein R J1 represents an alkyl group having 1 to 8 carbon atoms, 1 or non-adjacent 2 or more-CH 2 -in the alkyl group may each independently be substituted with-CH=CH-, -C≡C-, -O-, -CO-, -COO-, or-OCO-,
N J1 represents 0, 1,2, 3 or 4,
A J1、AJ2 and a J3 each independently represent a group selected from the group consisting of:
(a) 1, 4-cyclohexylene (1-CH 2 -or 2 or more-CH 2 -which are not adjacent to one another in this group may be substituted by-O.)
(B) 1, 4-phenylene (1-ch=or non-adjacent more than 2-ch=present in the group may be substituted with-n=) and
(C) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-ch=or non-adjacent 2 or more-ch=groups present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted with-n=)
The above-mentioned group (a), group (b) and group (c) may each independently be substituted with cyano group, fluorine atom, chlorine atom, methyl group, trifluoromethyl group or trifluoromethoxy group,
Z J1 and Z J2 each independently represent a single bond 、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-、-COO-、-OCO- or-C.ident.C-,
Where n J1 is 2, 3 or 4 and a J2 is present in plural, they may be the same or different, where n J1 is 2, 3 or 4 and Z J1 is present in plural, they may be the same or different,
X J1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a 2, 2-trifluoroethyl group. )
In the general formula (J), R J1 is preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, particularly preferably an alkenyl group (propenyl group) having 3 carbon atoms.
In the case where reliability is important, R J1 is preferably an alkyl group, and in the case where viscosity reduction is important, an alkenyl group is preferably used.
Further, when the ring structure to which the compound is bonded is phenyl (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 4 to 5 carbon atoms, and the ring structure to which the compound is bonded is cyclohexane, pyran or dioxaneIn the case of a saturated ring structure such as an alkane, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.
The alkenyl group is preferably a group represented by any one selected from the formulae (R1) to (R5). (the black dots in the formulae represent carbon atoms in the ring structure to which the alkenyl groups are bonded.)
[ Chemical 108]
A J1、AJ2 and A J3 are each independently of the other preferably aromatic in the case where an increase in Δn is required, and are preferably aliphatic for improving the response speed, preferably represent trans-1, 4-cyclohexylene, 1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2] octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decalin-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, which may be substituted by fluorine atoms, more preferably represent the structure,
[ 109]
More preferably, the following structure is shown.
[ 110]
Z J1 and Z J2 each independently preferably represent-CH 2O-、-OCH2-、-CF2O-、-CH2CH2-、-CF2CF2 -or a single bond, further preferred is-OCH 2-、-CF2O-、-CH2CH2 -or a single bond, and particularly preferred is-OCH 2-、-CF2 O-or a single bond.
X J1 is preferably a fluorine atom or a trifluoromethoxy group, preferably a fluorine atom.
N J1 is preferably 0,1,2 or 3, preferably 0,1 or 2, and in the case of focusing on improvement of Δε, preferably 0 or 1, and in the case of focusing on T NI, preferably 1 or 2.
The types of the combinable compounds are not particularly limited, and may be used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of the compounds used are, for example, 1,2, 3 in one embodiment of the present invention. In other embodiments of the present invention, the number of the components is 4, 5, 6, or 7 or more.
In the composition of the present invention, the content of the compound represented by the general formula (J) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, etc.
The lower limit of the preferable content of the compound represented by the general formula (J) is 1%, 10%, 20%, 30%, 40%, 50%,55%,60%,65%,70%,75%,80% relative to the total amount of the composition of the present invention. The upper limit of the preferable content with respect to the total amount of the composition of the present invention is, for example, 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25% in one embodiment of the present invention.
In the case of a composition in which the viscosity of the composition of the present invention is kept low and a high response speed is required, it is preferable to keep the lower limit value and the upper limit value low. Further, in the case of a composition in which T NI of the composition of the present invention is kept high and a good temperature stability is required, it is preferable to make the above-mentioned lower limit value and the upper limit value low. In order to keep the drive voltage low and to increase the dielectric anisotropy, it is preferable to make the lower limit value high and the upper limit value high.
In the case where reliability is important, R J1 is preferably an alkyl group, and in the case where viscosity reduction is important, an alkenyl group is preferably used.
The compound represented by the general formula (J) is preferably a compound represented by the general formula (M).
The composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (M). These compounds correspond to compounds having positive dielectric properties (Δε is greater than 2.).
[ Chemical 111]
(Wherein R M1 represents an alkyl group having 1 to 8 carbon atoms, 1 or non-adjacent 2 or more-CH 2 -in the alkyl group may each independently be substituted with-CH=CH-, -C≡C-, -O-, -CO-, -COO-, or-OCO-,
N M1 represents 0, 1,2, 3 or 4,
A M1 and a M2 each independently represent a group selected from the group consisting of:
(a) 1, 4-Cyclohexylene (1-CH 2 -or not present in this group) adjacent more than 2-CH 2 -can to be substituted by-O-or-S-) and
(B) 1, 4-phenylene (1-ch=or non-adjacent 2 or more-ch=present in the group may be substituted with-n=)
The hydrogen atoms on the above-mentioned group (a) and group (b) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
Z M1 and Z M2 each independently represent a single bond 、-CH2CH2-、-(CH2)4-、-OCH2-、-CH2O-、-OCF2-、-CF2O-、-COO-、-OCO- or-C.ident.C-,
Where n M1 is 2, 3 or 4 and a M2 is present in plural, they may be the same or different, where n M1 is 2, 3 or 4 and Z M1 is present in plural, they may be the same or different,
X M1 and X M3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom,
X M2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a2, 2-trifluoroethyl group.
In the general formula (M), R M1 is preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, particularly preferably an alkenyl group (propenyl group) having 3 carbon atoms.
In the case where reliability is important, R M1 is preferably an alkyl group, and in the case where viscosity reduction is important, an alkenyl group is preferably used.
Further, when the ring structure to which the compound is bonded is phenyl (aromatic), it is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms or an alkenyl group having 4 to 5 carbon atoms, and the ring structure to which the compound is bonded is cyclohexane, pyran or dioxaneIn the case of a saturated ring structure such as an alkane, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.
The alkenyl group is preferably a group represented by any one selected from the formulae (R1) to (R5). (the black dots in the formulae represent carbon atoms in the ring structure to which the alkenyl groups are bonded.)
[ Chemical 112]
A M1 and A M2 are each independently preferably aromatic in the case where an increase in Δn is required, and are preferably aliphatic for improving the response speed, and preferably represent trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2] octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represent the following structure,
[ 113]
More preferably, the following structure is shown.
[ 114]
Z M1 and Z M2 each independently preferably represent-CH 2O-、-CF2O-、-CH2CH2-、-CF2CF2 -or a single bond, further preferred is-CF 2O-、-CH2CH2 -or a single bond, and particularly preferred is-CF 2 O-or a single bond.
N M1 is preferably 0,1,2 or 3, preferably 0,1 or 2, and in the case of focusing on improvement of Δε, preferably 0 or 1, and in the case of focusing on T NI, preferably 1 or 2.
The types of the combinable compounds are not particularly limited, and may be used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of the compounds used are, for example, 1,2, 3 in one embodiment of the present invention. In other embodiments of the present invention, the number of the components is 4, 5, 6, or 7 or more.
In the composition of the present invention, the content of the compound represented by the general formula (M) is required to be appropriately adjusted in accordance with the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, and the like.
The lower limit of the preferable content of the compound represented by the formula (M) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the preferable content with respect to the total amount of the composition of the present invention is, for example, 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25% in one embodiment of the present invention.
In the case of a composition in which the viscosity of the composition of the present invention is kept low and a high response speed is required, it is preferable to keep the lower limit value and the upper limit value low. Further, in the case of a composition in which T NI of the composition of the present invention is kept high and a good temperature stability is required, it is preferable to make the above-mentioned lower limit value and the upper limit value low. In order to keep the drive voltage low and to increase the dielectric anisotropy, it is preferable to make the lower limit value high and the upper limit value high.
The liquid crystal composition of the present invention contains a compound having a structure represented by the formula (Y) in the molecule, but other polymerizable compounds may be used in combination. By using other polymerizable compounds in combination, the polymerization rate and formation of pretilt angle of the polymerizable compound can be further increased. In addition, a pretilt angle can be sufficiently obtained, the residual amount of the polymerizable compound is small, a high Voltage Holding Ratio (VHR) can be obtained, and further, burn-in of the liquid crystal display element can be suppressed. The other polymerizable compound is preferably a compound represented by the following general formula (P),
[ 115]
(In the general formula (P), R p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or-Sp p2-Pp2, 1 or non-adjacent 2 or more-CH 2 -groups in the alkyl group may each independently be substituted by-CH=CH-, -C≡C-, -O-, -CO-, -COO-, or-OCO-, 1 or more hydrogen atoms in the alkyl group may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
P p1 and P p2 each independently represent any one of the general formulae (P p1 -1) to (P p1 -9),
[ 116]
(Wherein R p11 and R p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, W p11 represents a single bond, -O-, -COO-or methylene, t p11 represents 0, 1 or 2, and when a plurality of R p11、Rp12、Wp11 and/or t p11 exist in the molecule, they may be the same or different.)
Sp p1 and Sp p2 each independently represent a single bond or a spacer,
Z p1 and Z p2 each independently represent a single bond 、-O-、-S-、-CH2-、-OCH2-、-CH2O-、-CO-、-C2H4-、-COO-、-OCO-、-OCOOCH2-、-CH2OCOO-、-OCH2CH2O-、-CO-NRZP1-、-NRZP1-CO-、-SCH2-、-CH2S-、-CH＝CRZP1-COO-、-CH＝CRZP1-OCO-、-COO-CRZP1＝CH-、-OCO-CRZP1＝CH-、-COO-CRZP1＝CH-COO-、-COO-CRZP1＝CH-OCO-、-OCO-CRZP1＝CH-COO-、-OCO-CRZP1＝CH-OCO-、-(CH2)z-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-(C＝O)-O-(CH2)2-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF2-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2- or-C≡C- (wherein, Z each independently represents an integer of 1 to 4, R ZP1 each independently represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, and when there are a plurality of R ZP1 in the molecule, they may be the same or different.)
A p1、Ap2 and a p3 each independently represent a group selected from the group consisting of:
(a p) 1, 4-cyclohexylene (1-CH 2 present in the radical) -or more than 2 non-adjacent-CH 2 -may be substituted by-O-)
(B p) 1, 4-phenylene (1-ch=or non-adjacent more than 2-ch=that are present in the group may be substituted with-n=) and
(C p) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, decalin-2, 6-diyl, phenanthrene-2, 7-diyl or anthracene-2, 6-diyl (1-ch=or non-adjacent 2 or more-ch=present in these groups may be substituted with-n=and the hydrogen atom present in this group may be substituted with a halogen atom, an alkyl group having 1 to 8 carbon atoms or an alkenyl group having 1 to 8 carbon atoms.)
In the above-mentioned group (a p), group (b p) and group (c p), each hydrogen atom present in the group may be independently substituted with a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, a cyano group or-Sp p2-Pp2,
M p1 represents 0, 1,2 or 3, and in the case where a plurality of Z p1、Ap2、Spp2 and/or P p2 exist in the molecule, they may be the same or different. ).
The polymerizable compound preferably contains 1 or 2 or more.
In the general formula (P) according to the present invention, R p1 is preferably-Sp p2-Pp2.
Each of P p1 and P p2 is preferably any one of the formulae (P p1 -1) to (P p1 -3), and preferably (P p1 -1).
R p11 and R p12 are each independently preferably a hydrogen atom or a methyl group.
T p11 is preferably 0 or 1.
W p11 is preferably a single bond, methylene or ethylene.
M p1 is preferably 0, 1 or 2, preferably 0 or 1.
Z p1 and Z p2 are each independently preferably a single bond 、-OCH2-、-CH2O-、-CO-、-C2H4-、-COO-、-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-C2H4COO-、-CH＝CH-、-CF2-、-CF2O-、-(CH2)2-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH2)2-、-OCF2- or-C.ident.C-, preferably a single bond 、-OCH2-、-CH2O-、-C2H4-、-COO-、-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-C2H4COO-、-CH＝CH-、-(CH2)2-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH2)2- or-C.ident.C-, preferably only 1 present in the molecule is -OCH2-、-CH2O-、-C2H4-、-COO-、-OCO-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-C2H4COO-、-CH＝CH-、-(CH2)2-COO-、-(CH2)2-OCO-、-OCO-(CH2)2-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH2)2- or-C.ident.C-, all the others are single bonds, preferably, only 1 present in the molecule is-OCH 2-、-CH2O-、-C2H4 -, -COO-or-OCO-, all other are single bonds, preferably all single bonds.
In addition, only 1 of Z p1 and Z p2 existing in the molecule is a linking group selected from the group consisting of -CH＝CH-COO-、-COO-CH＝CH-、-(CH2)2-COO-、-(CH2)2-OCO-、-O-CO-(CH2)2-、-COO-(CH2)2-, and the other is preferably a single bond.
Sp p1 and Sp p2 each independently represent a single bond or a spacer, the spacer preferably being an alkylene group having 1 to 30 carbon atoms, the-CH 2 -groups in the alkylene groups may be represented by-O-as long as the oxygen atoms are not directly bonded to each other-CO-, -COO-, -OCO-, -CH=CH-, or-C≡C-substitution, the hydrogen atom in the alkylene group may be substituted with a halogen atom, and is preferably a straight-chain alkylene group having 1 to 10 carbon atoms or a single bond.
A p1、Ap2 and A p3 are each independently preferably 1, 4-phenylene or 1, 4-cyclohexylene, preferably 1, 4-phenylene. In order to improve the compatibility with the liquid crystal compound, the 1, 4-phenylene group is preferably substituted with 1 fluorine atom, 1 methyl group or 1 methoxy group.
The total content of the compounds represented by the general formula (P) is preferably 0.05 to 10%, preferably 0.1 to 8%, preferably 0.1 to 5%, preferably 0.1 to 3%, preferably 0.2 to 2%, preferably 0.2 to 1.3%, preferably 0.2 to 1%, preferably 0.2 to 0.56% based on the composition of the present application containing the compounds represented by the general formula (P).
The preferable lower limit value of the total content of the compounds represented by the general formula (P) is 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3% with respect to the composition of the present application containing the compounds represented by the general formula (P).
The preferable upper limit value of the total content of the compounds represented by the general formula (P) is 10%, 8%, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5% with respect to the composition of the present application containing the compounds represented by the general formula (P).
If the content is small, there are problems that the effect of adding the compound represented by the general formula (P) is hardly exhibited, the alignment restricting force of the liquid crystal composition is weak or the time period becomes weak, and if it is too large, there are problems that the amount of remaining after curing becomes large, the time taken for curing takes place, the reliability of the liquid crystal is lowered, and the like. Therefore, the content is set in consideration of their balance.
The total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is preferably 0.05 to 10%, preferably 0.1 to 8%, preferably 0.1 to 5%, preferably 0.1 to 3%, preferably 0.2 to 2%, preferably 0.2 to 1.3%, preferably 0.2 to 1%, preferably 0.2 to 0.56% relative to the composition containing these compounds.
The preferable lower limit value of the total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3% with respect to the composition containing these compounds.
The preferable upper limit value of the total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is 10%, 8%, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5% relative to the composition containing these compounds.
If the content is small, there are problems that it is difficult to exhibit the effect of adding the compound represented by the formula (Y) and the compound represented by the general formula (P) to the molecule, the alignment regulating force of the liquid crystal composition becomes weak or the alignment regulating force becomes weak with time, and if it is too large, there are problems that the amount of remaining after curing becomes large, the curing takes time, the reliability of the liquid crystal is lowered, and the like. Therefore, the content is set in consideration of their balance.
As a preferable example of the compound represented by the general formula (P) according to the present invention, there may be mentioned polymerizable compounds represented by the following formulas (P-1-1) to (P-1-46).
[ Chemical 117]
[ Chemical 118]
[ 119]
[ 120]
[ Chemical 121]
(Wherein P p11、Pp12、Spp11 and Sp p12 each represent the same meaning as P p1、Pp2、Spp1 and Sp p2 in the general formula (P))
As a preferable example of the compound represented by the general formula (P) according to the present invention, there may be mentioned polymerizable compounds represented by the following formulas (P-2-1) to (P-2-14).
[ Chemical 122]
(Wherein P p21、Pp22、Spp21 and Sp p22 each represent the same meaning as P p1、Pp2、Spp1 and Sp p2 in the general formula (P))
As a preferable example of the compound represented by the general formula (P) according to the present invention, there may be mentioned polymerizable compounds represented by the following formulas (P-3-1) to (P-3-15).
[ 123]
[ Chemical 124]
(Wherein P p31、Pp32、Spp31 and Sp p32 represent the same meanings as those of P p1、Pp2、Spp1 and Sp p2 in the general formula (P))
As a preferable example of the compound represented by the general formula (P) according to the present invention, there may be mentioned polymerizable compounds represented by the following formulas (P-4-1) to (P-4-21).
[ 125]
[ 126]
[ 127]
[ 128]
( Wherein P p41、Pp42、Spp41 and Sp p42 represent the same meanings as those of P p1、Pp2、Spp1 and Sp p2 in the general formula (P). Wherein the plurality of P p41、Pp42、Spp41 and Sp p42 may be the same or different. )
In the case where a polymerizable compound is added to the composition of the present invention, polymerization proceeds even in the absence of a polymerization initiator, but a polymerization initiator may be contained to promote polymerization. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, and acylphosphine oxides.
The composition of the present invention may further contain a compound represented by the general formula (Q).
[ 129]
(Wherein R Q represents a straight-chain alkyl group or a branched alkyl group having 1 to 22 carbon atoms, 1 or more CH 2 groups in the alkyl group may be represented by-O-, which is not directly adjacent to the oxygen atom-CH=CH-, -CO-, -OCO-, -COO-, -C.ident.C-, -CF 2O-、-OCF2 -, M Q represents trans-1, 4-cyclohexylene, 1, 4-phenylene or a single bond.)
R Q represents a linear or branched alkyl group having 1 to 22 carbon atoms, 1 or more CH 2 groups in the alkyl group may be represented by-O-, in such a manner that oxygen atoms are not directly adjacent-CH=CH-, -CO-, -OCO-, -COO-, -C.ident.C-, -CF 2O-、-OCF2 -substitution, preferably a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group, a linear alkyl group in which 1 CH 2 group is replaced with-OCO-or-COO-, branched alkyl, branched alkoxy, branched alkyl in which 1 CH 2 group is replaced by-OCO-or-COO-, branched alkyl, branched alkoxy branched alkyl with 1 CH 2 group replaced by-OCO-or-COO-. M Q represents trans-1, 4-cyclohexylene, 1, 4-phenylene or a single bond, preferably trans-1, 4-cyclohexylene or 1, 4-phenylene.
The compounds represented by the general formula (Q) are more specifically preferably compounds represented by the following general formulae (Q-a) to (Q-d).
[ 130]
Wherein R Q1 is preferably a linear or branched alkyl group having 1 to 10 carbon atoms, R Q2 is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, R Q3 is preferably a linear, branched alkyl, linear or branched alkoxy group having 1 to 8 carbon atoms, and L Q is preferably a linear or branched alkylene group having 1 to 8 carbon atoms. Of the compounds represented by the general formulae (Q-a) to (Q-d), the compounds represented by the general formulae (Q-c) and (Q-d) are further preferable.
The composition of the present application preferably contains 1 or 2 compounds represented by the general formula (Q), more preferably 1 to 5 compounds, and the content thereof is preferably 0.001% to 1%, still more preferably 0.001% to 0.1%, particularly preferably 0.001% to 0.05%.
The liquid crystal composition of the present invention may contain, in addition to the above-mentioned compounds, a usual nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, light stabilizer, infrared absorber, or the like.
The antioxidants and light stabilizers which can be used in the present invention are more specifically preferably compounds represented by the following (III-1) to (III-40).
[ 131]
[ Chemical 132]
[ Chemical 133]
[ 134]
[ Chemical 135]
[ Chemical 136]
[ 137]
[ 138]
[ Chemical 139]
(Wherein n represents an integer of 0 to 20.)
The composition of the present application preferably contains 1 or 2 or more compounds selected from the compounds represented by the general formula (Q) or the compounds represented by the general formulae (III-1) to (III-40), more preferably 1 to 5, and further preferably 0.001% to 1%, still more preferably 0.001% to 0.1%, particularly preferably 0.001% to 0.05%.
The liquid crystal composition of the present invention preferably has a dielectric anisotropy (. DELTA.. Di-elect cons.) of from-2.0 to-8.0, more preferably from-2.0 to-5.0, particularly preferably from-2.5 to-5.0, at 20 ℃.
The refractive index anisotropy (Δn) of the liquid crystal composition of the present invention at 20 ℃ is preferably 0.08 to 0.14, more preferably 0.09 to 0.13, particularly preferably 0.09 to 0.12. As will be described in further detail, it is preferably 0.10 to 0.13 for a thin cell gap and 0.08 to 0.10 for a thick cell gap.
The viscosity (. Eta.) of the liquid crystal composition of the present invention at 20℃is preferably 10 to 50 mPas, preferably 10 to 40 mPas, preferably 10 to 35 mPas, preferably 10 to 30 mPas, more preferably 10 to 25 mPas, particularly preferably 10 to 22 mPas.
The liquid crystal composition of the present invention preferably has a rotational viscosity (γ 1) at 20 ℃ of 50 to 160 mPa-s, preferably 60 to 150 mPa-s, preferably 60 to 140 mPa-s, preferably 60 to 130 mPa-s, preferably 60 to 125 mPa-s, more preferably 60 to 120 mPa-s, more preferably 60 to 115 mPa-s, more preferably 60 to 110 mPa-s, and particularly preferably 60 to 100 mPa-s.
The nematic phase-isotropic liquid phase transition temperature (T ni) of the liquid crystal composition of the present invention is preferably 60 ℃ to 120 ℃, more preferably 70 ℃ to 100 ℃, particularly preferably 70 ℃ to 85 ℃.
The preferred embodiment of the liquid crystal composition according to the present invention is preferably classified into a case where the liquid crystal composition as a whole exhibits positive dielectric anisotropy and a case where the liquid crystal composition as a whole exhibits negative dielectric anisotropy.
For example, when the liquid crystal composition according to the present invention exhibits positive dielectric anisotropy as a whole, it is preferable that the liquid crystal composition contains a compound having a structure represented by the general formula (Y), 1 or 2 or more compounds selected from the compounds represented by the general formula (J), and the compounds represented by the general formula (L) in the molecule.
In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the component composed of only the compound having the structure represented by the general formula (Y), the compound having the general formula (J) and the compound having the general formula (L) in the molecule is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%.
In the liquid crystal composition according to the present invention, the lower limit value of the proportion of the component composed of only the compound having the structure represented by the general formula (Y), the compound having the general formula (J) and the compound having the general formula (L) in the molecule is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.
In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the component composed of only the compound having the structure represented by the general formula (Y), the compound having the general formula (P), and the compound having the general formula (L) in the molecule is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%.
In the liquid crystal composition according to the present invention, the lower limit of the proportion of the components consisting of only the compounds represented by the general formulae (I), (P) and (L) is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.
For example, in the case where the liquid crystal composition according to the present invention exhibits negative dielectric anisotropy as a whole, it is preferable that the liquid crystal composition contains a compound having a structure represented by the general formula (Y), 1 or 2 or more compounds selected from compounds represented by the general formulae (N-1), (N-2) and (N-3), and a compound represented by the general formula (L) in the molecule.
In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the components constituted by the compound having the structure represented by the general formula (Y), the general formula (N-1), the general formula (N-2), the general formula (N-3) and the general formula (L) in the molecule is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%.
In the liquid crystal composition according to the present invention, the lower limit value of the proportion of the components consisting of only the compound having the structure represented by the general formula (Y), the general formula (N-1), the general formula (N-2), the general formula (N-3) and the compound having the general formula (L) in the whole molecule is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.
In the entire liquid crystal composition according to the present invention, the upper limit of the proportion of the components constituted by the compounds represented by the general formula (Y), the general formula (N-1 a), the general formula (N-1 b), the general formula (N-1 c), the general formula (N-1 d), the general formula (N-1 e) and the general formula (L) is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass% only in the molecules.
In the liquid crystal composition according to the present invention, the lower limit value of the proportion of the components consisting of only the compounds having the structure represented by the general formula (Y), the general formula (N-1 a), the general formula (N-1 b), the general formula (N-1 c), the general formula (N-1 d), the general formula (N-1 e) and the general formula (L) in the whole molecule is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.
In the entire liquid crystal composition according to the present invention, the upper limit of the proportion of the components constituted by the compounds having the structure represented by the general formula (Y), the general formula (N-1-4), the general formula (N-1 b), the general formula (N-1 c), the general formula (N-1 d), the general formula (N-1 e) and the general formula (L) is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass% only in the molecules.
In the liquid crystal composition according to the present invention, the lower limit value of the proportion of the components consisting of only the compounds having the structure represented by the general formula (Y), the general formula (N-1-4), the general formula (N-1 b), the general formula (N-1 c), the general formula (N-1 d), the general formula (N-1 e) and the general formula (L) in the whole molecule is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.
In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the components including only the compounds having the structure represented by the general formula (Y), the general formula (N-1 a), the general formula (N-1 b), the general formula (N-1 c), the general formula (N-1 d), the general formula (N-1 e), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6) is preferably 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93% by mass, 92% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass, 83% by mass, 82% by mass, 81% by mass, 80% by mass.
In the liquid crystal composition according to the present invention, the lower limit value of the proportion of the components including only the compounds having the structure represented by the general formula (Y), the general formula (N-1 a), the general formula (N-1 b), the general formula (N-1 c), the general formula (N-1 d), the general formula (N-1 e), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5), and the general formula (L-6) in the whole molecule is preferably 68 mass%, 70 mass%, 71 mass%, 73 mass%, 75 mass%, 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.
In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the components constituted by the compounds having the structure represented by the general formula (Y), the general formula (N-1 a), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6) is preferably 100%, 99%, 98%, 97%, 96%, 95%, 94%, 93%, 92%, 91%, 90%, 89%, 88%, 87%, 86%, 85%, 84%, 83%, 82%, 81%, 80%, 79%, 78%, 77%, 76%, 75%, 74%, 73%, 72%, 71%, 70%, 69%, 68%, 67%, 66%, 65%, 64%, 63%, 62% by mass.
In the liquid crystal composition according to the present invention, the lower limit value of the proportion of the components including only the compound having the structure represented by the general formula (Y), the general formula (N-1 a), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6) in the molecule is preferably 38 mass%, 40 mass%, 41 mass%, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass%, 74 mass%, 76 mass%, 78 mass%, 80 mass%, 82 mass%, 84 mass%, 86 mass%, 88 mass%, 90 mass%, 92 mass%.
In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the components constituted by the compounds having the structure represented by the general formula (Y), the general formula (N-1 d), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6) in the molecule is preferably 100%, 99%, 98%, 97%, 96%, 95%, 94%, 93%, 92%, 91%, 90%, 89%, 88%, 87%, 86%, 85%, 84%, 83%, 82%, 81%, 80%, 79%, 78%, 77%, 76%, 75%, 74%, 73%, 72%, 71%, 70%, 69%, 68%, 67%, 66%, 65%, 64%, 63%, 62%.
In the liquid crystal composition according to the present invention, the lower limit value of the proportion of the components including only the compound having the structure represented by the general formula (Y), the general formula (N-1 d), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6) in the whole molecule is preferably 38 mass%, 40 mass%, 41 mass%, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass%, 74 mass%, 76 mass%, 78 mass%, 80 mass%, 82 mass%, 84 mass%, 86 mass%, 88 mass%, 90 mass%, 92 mass%.
The composition of the present application preferably does not contain a compound having a structure in which oxygen atoms such as a peroxy (-CO-OO-) structure are bonded to each other in the molecule.
In the case where importance is attached to the reliability and long-term stability of the composition, the content of the compound having a carbonyl group is preferably 5% or less, more preferably 3% or less, still more preferably 1% or less, and most preferably substantially none of the compound having a carbonyl group relative to the total mass of the composition.
In the case where importance is attached to stability after UV irradiation, the content of the compound substituted with a chlorine atom is preferably 15% or less, preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and even more preferably substantially no content of the compound is provided with respect to the total mass of the composition.
The content of the compound having all 6-membered rings in the molecule is preferably increased, the content of the compound having all 6-membered rings in the molecule is preferably 80% or more, more preferably 90% or more, still more preferably 95% or more, and most preferably the composition is substantially composed only of the compound having all 6-membered rings in the molecule, based on the total mass of the composition.
In order to suppress deterioration due to oxidation of the composition, the content of the compound having a cyclohexenylene group as a ring structure is preferably reduced, and the content of the compound having a cyclohexenylene group is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and even more preferably substantially none of the compound is contained relative to the total mass of the composition.
In the case where improvement of viscosity and improvement of T NI are important, the content of the compound having a 2-methylbenzene-1, 4-diyl group in the molecule, which may be substituted with halogen, is preferably reduced, and the content of the compound having a 2-methylbenzene-1, 4-diyl group in the molecule is preferably 10% or less, preferably 8% or less, more preferably 5% or less, still more preferably 3% or less, and further preferably substantially none, relative to the total mass of the composition.
Substantially free of the present application means that the present application does not contain any substance other than the substance that is not intentionally contained.
(Liquid Crystal display element)
In addition to the remarkable characteristic of high-speed response, the liquid crystal display element using the liquid crystal composition of the present invention can sufficiently develop tilt without unreacted polymerizable compound or with little to no problem, and has a high Voltage Holding Ratio (VHR), and thus is free from or sufficiently suppressed from defects such as alignment failure and display failure. Further, the inclination angle and the residual amount of the polymerizable compound can be easily controlled, and therefore the energy cost for manufacturing can be easily optimized and reduced, and thus it is most suitable for improvement of production efficiency and stable mass production.
The liquid crystal display element using the liquid crystal composition of the present invention is particularly useful for an active matrix driving liquid crystal display element, and can be used for a PSA mode, a PSVA mode, a VA mode, a PS-IPS mode, a PS-FFS mode, an IPS mode, and an FFS mode liquid crystal display element.
As an example of the liquid crystal display element according to the present invention, it is preferable that the liquid crystal display element includes a first substrate and a second substrate which are arranged to face each other, a common electrode provided on the first substrate or the second substrate, a pixel electrode provided on the first substrate or the second substrate and having a thin film transistor, and a liquid crystal layer containing a liquid crystal composition provided between the first substrate and the second substrate. An alignment film for controlling the alignment direction of the liquid crystal molecules may be provided on the facing surface side of at least one of the first substrate and/or the second substrate so as to be in contact with the liquid crystal layer, as needed. As the alignment film, a vertical alignment film, a horizontal alignment film, or the like can be appropriately selected according to the driving mode of the liquid crystal display element, and a known alignment film such as a rubbing alignment film (for example, polyimide) or a photo alignment film (for example, decomposed polyimide) can be used. Further, a color filter may be provided on the first substrate or the second substrate as appropriate, and a color filter may be provided on the pixel electrode or the common electrode.
The 2-plate substrate of the liquid crystal cell used in the liquid crystal display element according to the present invention may be made of glass, a transparent material such as plastic having flexibility, or an opaque material such as silicon. The transparent substrate having the transparent electrode layer can be obtained by sputtering Indium Tin Oxide (ITO) on a transparent substrate such as a glass plate.
The color filter can be manufactured by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like. In the following description, a method of manufacturing a color filter by a pigment dispersion method will be described as an example, in which a curable coloring composition for a color filter is applied to a transparent substrate, patterned, and then cured by heating or light irradiation. This step is performed for each of the 3 colors of red, green, and blue, so that a pixel portion for a color filter can be manufactured. Further, a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal-insulator-metal (soi) resistivity element may be provided on the substrate.
The first substrate and the second substrate are preferably opposed to each other with the common electrode and the pixel electrode layer inside.
The spacing between the first substrate and the second substrate may be adjusted by a spacer. In this case, the thickness of the light control layer is preferably adjusted so that the thickness of the light control layer becomes 1 to 100. Mu.m. Further preferably 1.5 to 10 μm, and in the case of using a polarizing plate, the product of the refractive index anisotropy Δn of the liquid crystal and the cell thickness d is preferably adjusted so as to maximize the contrast. In the case of two polarizing plates, the viewing angle and contrast can be adjusted to be good by adjusting the polarizing axis of each polarizing plate. Further, a retardation film for enlarging the viewing angle may be used. Examples of the spacers include glass particles, plastic particles, alumina particles, and photoresist materials. Thereafter, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates in such a manner that a liquid crystal injection port is provided, the substrates are bonded to each other, and the sealant is thermally cured by heating.
As a method for sandwiching the liquid crystal composition between 2 substrates, a general vacuum injection method, an ODF method, or the like can be used.
As a method for polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention, a method of polymerizing by irradiation of active energy rays such as ultraviolet rays or electron rays alone or in combination or sequentially is preferable because a proper polymerization rate is desired in order to obtain good alignment performance of liquid crystals. In the case of using ultraviolet rays, a polarized light source may be used, or an unpolarized light source may be used. In addition, in the case of polymerizing the liquid crystal composition in a state of being sandwiched between 2 substrates, at least the substrate on the irradiation surface side must have appropriate transparency to active energy rays. Further, a method may be used in which only a specific portion is polymerized by using a mask at the time of irradiation with light, the alignment state of an unpolymerized portion is changed by changing conditions such as an electric field, a magnetic field, or a temperature, and active energy rays are further irradiated to polymerize the unpolymerized portion. In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the liquid crystal composition. The applied alternating electric field is preferably alternating with a frequency of 10Hz to 10kHz, more preferably with a frequency of 60Hz to 10kHz, the voltage being selected in accordance with the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In a liquid crystal display element such as a PSVA mode liquid crystal display element in which the alignment of liquid crystal molecules at the time of no voltage application, that is, the initial alignment of liquid crystal is substantially perpendicular to a substrate, the pretilt angle is preferably controlled to 80 to 89.9 degrees from the viewpoints of alignment stability and contrast. The term "substantially perpendicular" includes an angle having a pretilt angle as described above, and an angle between the long axis direction of the liquid crystal molecules and the substrate is preferably 70 degrees or more, more preferably 75 degrees or more, and still more preferably 80 degrees or more.
The temperature at which the active energy rays such as ultraviolet rays or electron rays are irradiated for polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention is not particularly limited. For example, when the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate with an alignment film, the liquid crystal composition is preferably in a temperature range in which the liquid crystal state of the liquid crystal composition can be maintained. The polymerization is preferably carried out at a temperature close to room temperature, i.e., typically 15 to 35 ℃.
On the other hand, for example, in the case where the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate without an alignment film, the temperature range may be wider than the above-described temperature range when applied to the irradiation of a liquid crystal display element having a substrate with an alignment film.
As the lamp for generating ultraviolet rays, a metal halide lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, or the like can be used. The wavelength of the ultraviolet light to be irradiated is preferably ultraviolet light whose irradiation wavelength range is not in the absorption wavelength range of the liquid crystal composition, and it is preferable to use the liquid crystal composition after cutting off the ultraviolet light if necessary. The intensity of the irradiated ultraviolet light is preferably 0.1mW/cm 2～100W/cm2, more preferably 2mW/cm 2～50W/cm2. The energy of the irradiated ultraviolet rays can be suitably adjusted, and is preferably 10mJ/cm 2 to 500J/cm 2, and more preferably 100mJ/cm 2 to 200J/cm 2. The intensity may be changed when ultraviolet rays are irradiated. The time for irradiating ultraviolet rays is appropriately selected depending on the intensity of the irradiated ultraviolet rays, and is preferably 10 seconds to 3600 seconds, and more preferably 10 seconds to 600 seconds.
Although an example of the liquid crystal display element and the method for manufacturing the liquid crystal display element according to the present invention has been described above, the present invention is not limited to the foregoing embodiments.
For example, the liquid crystal display element of the present invention may have a part of its structure replaced with another structure that performs the same function, or may have any structure added thereto. The method for manufacturing a liquid crystal display element of the present invention may have an additional step for any purpose, or may be replaced with any step that can obtain the same operation and effect.
Examples
The present invention will be described in further detail with reference to the following examples, but the present invention is not limited to these examples. In the compositions of the following examples and comparative examples, "%" means "% by mass". The following abbreviations are used for the compounds in the examples.
The physical property values are measured based on the method described in the electronic information technology industry association release of the modified society of the electronic information technology industry, standard JEITA ED-2521b, 3 months 2009, unless otherwise specified.
(Side chain)
(Linking base)
(Ring structure)
[ 140]
In the examples, the measured characteristics are as follows.
Tni nematic phase-isotropic liquid phase transition temperature (°C)
Refractive index anisotropy at 20 ℃ delta n
Dielectric constant anisotropy at 20 DEG delta epsilon
Gamma 1 rotational viscosity at 20 ℃ (mPa. S)
(Synthesis of a Compound having a Structure represented by the general formula (Y) in the molecule)
(Synthesis of RM-1)
To a reaction vessel equipped with a stirring device, a condenser and a thermometer, 2.2g (9.7 mmol) of 4- (4-hydroxyphenyl) thiomorpholine 1, 1-dioxide, 2g (15.5 mmol) of diisopropylethylamine and 11ml of methylene chloride were added, and the reaction vessel was kept at 5℃or less by means of an ice-cold bath, and 1.6g (15.3 mmol) of methacryloyl chloride was slowly added dropwise under a nitrogen atmosphere. After the completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 5 hours. To the reaction solution was added 60ml of methylene chloride, which was then washed with aqueous hydrochloric acid, followed by washing with water, and further washing with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, it was purified by a 2-fold amount (weight ratio) of a silica gel column to obtain 1.3g of the compound represented by (RM-1).
[ 141]
1 H-NMR (solvent: deuterated chloroform): delta: 2.07 (s, 3H), 3.63 (dd, 4H), 3.93 (dd, 4H), 6.25-6.17 (m, 1H), 6.41-6.45 (m, 1H), 6.65-6.92 (m, 4H)
(Synthesis of RM-2)
To a reaction vessel equipped with a stirring device, a heating device and a thermometer, 6.9g (50.0 mmol) of 4-hydroxyphenylboronic acid, 11.5g (49.7 mmol) of 4-bromo-2- (3-hydroxypropyl) phenol, 176mg (0.24 mmol) of bis [ di-t-butyl (4-dimethylaminophenyl) phosphine ] palladium (II) dichloride and 46ml of tetrahydrofuran were added, and after heating at 65℃and dropwise adding a 2M aqueous potassium carbonate solution (37.5 ml, 75 mmol), the mixture was reacted for 5 hours. To the reaction mixture was added 100ml of ethyl acetate, which was washed with aqueous hydrochloric acid, and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the mixture was purified by a 2-fold amount (weight ratio) of a silica gel column, and recrystallized by hexane/ethyl acetate to obtain 13.5g of the compound represented by (1).
[ 142]
In a reaction vessel equipped with a stirring device, a condenser and a thermometer, 8.3g (46.6 mmol) of N-bromosuccinimide was dissolved in methylene chloride, and a methylene chloride solution (25 ml) of 12.5g (47.7 mmol) of triphenylphosphine was added dropwise while stirring at-78 ℃. In the course of cooling and stirring the obtained solution at-78 ℃, 10.0g (40.9 mmol) of the compound represented by (1) in methylene chloride (25 ml) was added dropwise, and then the reaction temperature was raised to room temperature to react for 5 hours. To the reaction mixture was added 100ml of toluene, which was washed with water and then with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the mixture was purified by a 2-fold amount (weight ratio) of a silica gel column, and recrystallized by hexane/ethyl acetate to obtain 8.2g of the compound represented by (2).
[ 143]
5.0G (16.3 mmol) of the compound shown in (2), 11g (81.4 mmol) of thiomorpholine 1, 1-dioxide, 8.0g (24.6 mmol) of cesium carbonate and 100ml of tetrahydrofuran were charged into a reaction vessel equipped with a stirring device, a heating device and a thermometer, and heated at 65℃to react for 5 hours. To the reaction mixture was added 100ml of ethyl acetate, which was washed with aqueous hydrochloric acid, and further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the mixture was purified by a 2-fold amount (weight ratio) of a silica gel column, and recrystallized by hexane/ethyl acetate to obtain 4.1g of the compound represented by (3).
[ 144]
The same procedure as in the synthesis of (RM-1) was used for the compound shown in (3), whereby 0.5g of the compound shown in (RM-2) was obtained.
[ Chemical 145]
1 H-NMR (solvent: deuterated chloroform )：δ：1.89(t,2H),2.02(s,6H),2.42(t,2H),2.62(t,2H),2.89(dd,4H),3.50(dd,4H),6.25-6.17(m,2H),6.41-6.45(m,2H),7.15-7.82(m,7H))
(Synthesis of RM-3)
To a reaction vessel equipped with a stirring device, a heating device and a thermometer, 1.37g (10.0 mmol) of 2- (4-aminophenyl) ethanol, 2.0g (16.9 mmol) of divinyl sulfone, 62mg (1.0 mmol) of boric acid, 15ml of water and a few drops of glycerin were added, and the mixture was heated and refluxed under a nitrogen atmosphere to react for 5 hours. To the reaction mixture was added 50ml of ethyl acetate, which was then washed with water and then with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, it was purified by a 2-fold amount (weight ratio) of a silica gel column to obtain 1.7g of the compound represented by (4).
[ 146]
The same procedure as in the synthesis of (RM-1) was used for the compound shown in (4), whereby 1.8g of the compound shown in (RM-3) was obtained.
[ Chemical 147]
1 H-NMR (solvent: deuterated chloroform )：δ：2.03(s,3H),2.82(dd,2H),3.64(dd,4H),3.92(dd,4H),4.49(dd,2H),6.25-6.17(m,1H),6.41-6.45(m,1H),6.67-6.91(m,4H))
(Synthesis of RM-4)
The same procedure as in the case of synthesis (1) was used for 3-amino-4, 4-dihydroxybiphenyl, whereby 2.1g of the compound represented by formula (5) was obtained.
[ 148]
The same procedure as in the synthesis of (RM-1) was used for the compound shown in (5), whereby 0.9g of the compound shown in (RM-4) was obtained.
[ 149]
1 H-NMR (solvent: deuterated chloroform )：δ：2.03(s,6H),3.62(dd,4H),3.89(dd,4H),6.25-6.17(m,2H),6.41-6.45(m,2H),6.67-7.15(m,5H),7.67-7.71(m,2H))
(Synthesis of RM-5)
The same procedure as in the case of synthesis (4) was used for 2-amino-1, 3-propanediol to obtain 5.2g of the compound represented by (6).
[ 150]
5.0G (23.9 mmol) of the compound shown in (6), 6.6g (25.2 mmol) of triphenylphosphine, 6.8g (25.1 mmol) of 4-hydroxy-4' - (tetrahydro-2H-pyran-2-yloxy) biphenyl, 50ml of toluene and 7.3g (36.1 mmol) of diisopropyl azodicarboxylate were added dropwise to a reaction vessel equipped with a stirrer, a heater and a thermometer, and the mixture was reacted at 90℃for 5 hours. To the reaction mixture was added 50ml of ethyl acetate, which was then washed with water and then with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, it was purified by a 2-fold amount (weight ratio) of a silica gel column to obtain 8.3g of the compound represented by (7).
[ 151]
8.0G (mmol) of the compound shown in (7), 40ml of tetrahydrofuran and 10ml of 10% hydrochloric acid were charged into a reaction vessel equipped with a stirring device, a heating device and a thermometer, and reacted at 40℃for 5 hours under a nitrogen atmosphere. To the reaction mixture was added 50ml of ethyl acetate, which was then washed with water and then with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, it was purified by a 2-fold amount (weight ratio) of a silica gel column to obtain 6.5g of the compound represented by (8).
[ 152]
The same procedure as in the synthesis of (RM-1) was used for the compound shown in (8), whereby 0.9g of the compound shown in (RM-5) was obtained.
[ Chemical 153]
(Synthesis of RM-6)
The same procedure as in the synthesis of (RM-5) was used for 2-amino-2-methyl-1, 3-propanediol to give 1.2g of the compound represented by (RM-6).
[ 154]
(Synthesis of RM-7)
The same procedure as in the synthesis of (RM-1) was used for the compound shown in (7), whereby 2.1g of the compound shown in (9) was obtained.
[ Chemical 155]
The same method as in the case of synthesis (8) was used for the compound shown in (9), whereby 1.1g of the compound shown in (10) was obtained.
[ Chemical 156]
1.0G (2.2 mmol) of the compound shown in (10), 0.85g (6.6 mmol) of diisopropylethylamine and 5ml of methylene chloride were charged into a reaction vessel equipped with a stirring device, a condenser and a thermometer, the reaction vessel was kept at 5℃or less by means of an ice-cold bath, and 0.3g (3.3 mmol) of acryloyl chloride was slowly added dropwise under a nitrogen atmosphere. After the completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 5 hours. To the reaction solution was added 5ml of methylene chloride, which was then washed with aqueous hydrochloric acid, followed by washing with water, further washing with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the mixture was purified by a 2-fold amount (weight ratio) of a silica gel column to obtain 0.9g of the compound represented by (RM-7).
[ 157]
(Synthesis of RM-8)
The same procedure as in the synthesis of (RM-1) was used for the compound represented by 4- (4-hydroxyphenyl) tetrahydro-2H-thiopyran 1, 1-dioxide to give 1.1g of the compound represented by (RM-8).
[ Chemical 158]
(Synthesis of RM-9)
To a reaction vessel equipped with a stirring device and a heating device, 1.1g of 4,4 '-dihydroxy-3-fluoro-3' -nitrobiphenyl, 110mg of 20% Pd carbon powder (hydrous) NX type (catalyst) manufactured by N.E. CHEMCAT, inc.), 20ml of tetrahydrofuran, and a pressurized atmosphere of hydrogen (0.5 MPa) was added and the mixture was reacted at 50℃for 5 hours. After removing the catalyst by filtration, the solvent was distilled off, and then purified by a 2-fold amount (weight ratio) of a silica gel column to obtain 1.1g of the compound represented by (11).
The same method as in the case of synthesis (4) was used for the compound shown in (11), whereby 1.2g of the compound shown in (12) was obtained.
[ 159]
The same procedure as in the synthesis of (RM-1) was used for the compound represented by (12), whereby 0.7g of the compound represented by (RM-9) was obtained.
[ 160]
1 H-NMR (solvent: deuterated chloroform )：δ：2.02(s,6H),3.60(dd,4H),3.89(dd,4H),6.17-6.24(m,2H),6.41-6.44(m,2H),6.67-7.14(m,4H),7.67-7.70(m,2H))
(Synthesis of RM-10)
The same procedure as in the case of synthesis of (1) was used for 4-hydroxy-3-methoxyphenylboronic acid and 2-amino-4-bromophenol, whereby 5.1g of the compound represented by (13) was obtained.
[ 161]
The same method as in the case of synthesis (4) was used for the compound shown in (13), whereby 1.0g of the compound shown in (14) was obtained.
[ 162]
The same procedure as in the synthesis of (RM-1) was used for the compound shown in (14), whereby 0.7g of the compound shown in (RM-10) was obtained.
[ 163]
1 H-NMR (solvent: deuterated chloroform )：δ：2.01(s,6H),3.83(s,3H),3.60(dd,4H),3.89(dd,4H),6.16-6.24(m,2H),6.41-6.43(m,2H),6.68-7.14(m,3H),7.68-7.70(m,2H))
The same procedure as in the synthesis of (RM-1) was used for the compound represented by (3), whereby 0.6g of the compound represented by (RM-11) was obtained.
[ Chemical 164]
GC-MS:m/z=658.24
(Results of preparation and evaluation of liquid Crystal composition)
(Method for manufacturing liquid Crystal display element)
First, a liquid crystal composition containing a polymerizable compound described later was injected by a vacuum injection method into a liquid crystal cell having a cell gap of 3.5 μm containing an ITO-coated substrate which was coated with a polyimide alignment film for inducing vertical alignment and subjected to rubbing treatment. Then, a liquid crystal cell into which a liquid crystal composition containing a polymerizable compound was injected was irradiated with ultraviolet rays for 90 minutes using a fluorescent UV lamp, to obtain a liquid crystal display element. At this time, the fluorescent UV lamp was adjusted so that the illuminance measured at the center wavelength of 313nm became 3.0mW/cm 2.
(Evaluation method of Voltage holding Rate)
The liquid crystal cell injected with the liquid crystal composition containing the polymerizable compound was irradiated with UV for 90 minutes under the irradiation conditions, and the Voltage Holding Ratio (VHR) was measured under the conditions of 1V, 0.6Hz and 60 ℃. The value of A is 95% or more, B is less than 95% and 90% or more, C is less than 90% and 80% or more, and D is less than 80%.
(Evaluation method of Tilt formation (Pre-Tilt Change amount))
The amount of change in pretilt angle of the liquid crystal display element before and after irradiation of ultraviolet rays for 200 seconds under the irradiation conditions was measured by the following method. First, the pretilt angle of the liquid crystal display element is measured and set to be the pretilt angle (initial stage). The liquid crystal display element was irradiated with ultraviolet light for 200 seconds while applying a voltage of 10V at a frequency of 100 Hz. Then, the pretilt angle was measured and set to be the pretilt angle (after UV). The value obtained by subtracting the pretilt angle (after UV) from the measured pretilt angle (initial stage) was set as the pretilt angle change amount [ ° ]. Pretilt angle was measured using Shintec: OPTIPRO. The value of the pretilt angle change amount [ ° ] is set to be A when 2.0 DEG or more, B when less than 2.0 DEG and 1.5 DEG or more, C when less than 1.5 DEG and 1.0 DEG or more, and D when less than 1.0 deg.
(Evaluation method of Low-temperature storage Property)
A sample having low-temperature storage property was obtained by taking 0.5g of a liquid crystal composition containing a polymerizable compound into a test tube, deaerating for 15 minutes, and purging with nitrogen. The product was stored in a freezer at-20 ℃ and was found to be good when no precipitation was performed for 10 days, delta was found to be performed when precipitation was performed within 5 to 9 days, and X was found to be performed when precipitation was performed within 5 days.
(Results of preparation and evaluation of liquid Crystal composition)
The base compositions (LC-001) to (LC-008) were prepared, and the physical properties were measured. The component ratios and physical properties of these base compositions are shown in Table 1.
TABLE 1
| LC-001 | LC-002 | LC-003 | LC-004 | LC-005 | LC-006 | LC-007 | LC-008 | |
| 3-Cy-Cy-2 | 18 | 20 | 20 | 18.5 | 20 | |||
| 3-Cy-Cy-4 | 8 | 4 | 4 | |||||
| 3-Cy-Cy-5 | 6.75 | 7 | ||||||
| 3-Cy-Cy-V | 29 | 23 | 29 | |||||
| 3-Cy-Cy-V1 | 10 | 10.25 | ||||||
| 3-Cy-Ph-O1 | 6 | 4 | 3 | |||||
| 3-Ph-Ph-1 | 13 | 17 | 12 | 10 | 9 | |||
| 3-Cy-Cy-Ph-1 | 6 | 7 | 7 | |||||
| 3-Cy-Cy-Ph-3 | 4 | 4 | ||||||
| 3-Cy-Ph-Ph-1 | 7 | 5 | 5 | |||||
| 3-Cy-Ph-Ph-2 | 6 | 4 | 5 | |||||
| 5-Cy-Ph-Ph-2 | 4 | |||||||
| 1V2-Ph-Ph-1 | 3.75 | |||||||
| 3-Cy-Ph5-O2 | 11.5 | |||||||
| 3-Ph-Ph5-O2 | 12 | 5 | 12 | 10 | 10 | |||
| 3-Cy-Cy-Ph5-1 | 2.5 | |||||||
| 3-Cy-Cy-Ph5-O1 | 12 | |||||||
| 3-Cy-Cy-Ph5-O2 | 15 | 15 | ||||||
| 3-Cy-Cy-Ph5-O4 | 15 | 15 | ||||||
| 4-Cy-Cy-Ph5-O2 | 10 | 13 | ||||||
| 3-Cy-1O-Ph5-O1 | 6 | |||||||
| 3-Cy-1O-Ph5-O2 | 7 | 6 | 9 | 5 | ||||
| 1V-Cy-1O-Ph5-O2 | 6 | |||||||
| 2-Cy-Cy-1O-Ph5-O2 | 14 | 12 | ||||||
| 3-Cy-Cy-1O-Ph5-O2 | 3 | 15 | 10 | 12 | 12 | |||
| V-Cy-Cy-1O-Ph5-O2 | 4 | |||||||
| 1V-Cy-Cy-1O-Ph5-O2 | 5 | 5 | 5 | 6 | ||||
| 2-Cy-Ph-Ph5-O2 | 7 | 10 | 6 | 5 | 5 | |||
| 3-Cy-Ph-Ph5-O2 | 8 | 10 | 5 | 10.75 | 4 | 2 | ||
| 3-Cy-Ph-Ph5-O3 | 6 | |||||||
| 3-Cy-Ph-Ph5-O4 | 7 | 9 | ||||||
| 4-Cy-Ph-Ph5-O3 | 8 | |||||||
| 3-Ph-Ph5-Ph-2 | 5 | |||||||
| 2-Ph-2-Ph-Ph5-O2 | 5 | |||||||
| 3-Ph-2-Ph-Ph5-O2 | 5 | 5 | 8 | |||||
| Total (wt%) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| Tni[°C] | 73.8 | 74.4 | 76.7 | 76.2 | 72.8 | 74.7 | 111.2 | 110.2 |
| Δn | 0.111 | 0.112 | 0.118 | 0.128 | 0.114 | 0.103 | 0.098 | 0.098 |
| Δε | -3.2 | -2.8 | -3.3 | -3.4 | -3.3 | -3.1 | -3.1 | -3.1 |
| γ1[mPa·s] | 125 | 105 | 132 | 134 | 104 | 99 | 154 | 135 |
These base compositions (LC-001) to (LC-008) were mixed with compounds represented by the following formulas (RM-1) to (RM-11) and (RM-12) to (RM-13) to prepare liquid crystal compositions.
[ 165]
[ 166]
(Example 1. About.27)
To 100 parts by mass of the base composition LC-001, 0.4 part by mass of the formula (RM-1) and 0.3 part by mass of the formula (RM-12) were added as polymerizable compounds to prepare a liquid crystal composition containing the polymerizable compounds, and the voltage holding ratio, the pretilt angle change amount, and the low-temperature storage property were evaluated to prepare example 1. Examples 2 to 27 were carried out in the same manner. The results are shown in Table 2 below.
(Comparative example 1 to 9)
A liquid crystal composition containing a polymerizable compound was prepared by adding 0.3 part by mass of formula (RM-13) as a polymerizable compound to 100 parts by mass of the base composition LC-001, and the voltage holding ratio, the amount of change in pretilt angle, and the low-temperature storage property were evaluated to obtain comparative example 1. Comparative examples 2 to 9 were prepared in the same manner. The results are shown in Table 2 below.
TABLE 2
Examples 1 to 27 confirmed that the voltage holding ratio was sufficiently high, the amount of change in pretilt angle was large, and the low-temperature storage property was also sufficient. From the above results, it was confirmed that these examples solve the problems of the present invention.
In contrast, comparative example 1 has a lower voltage holding ratio and a smaller amount of change in pretilt angle than example 1 using the same base liquid crystal (LC-001). This is considered to be because comparative example 1 does not contain the polar compound of the present application, and therefore suffers from the influence of the polar impurities present in the liquid crystal cell, which results in a decrease in voltage holding ratio, and the polymerizable compound of the second component is less likely to locally concentrate on the substrate surface than the polar compound of the present application, resulting in insufficient polymerization and a decrease in tilt forming ability.
In comparative example 2, the voltage holding ratio and the amount of change in pretilt angle were both significantly deteriorated as compared with example 2 using the same basic liquid crystal (LC-002). This is considered to be because comparative example 2 is a base liquid crystal (LC-002) that tends to easily generate polar impurities, and therefore suffers from the influence of the polar impurities present in the liquid crystal cell, and the voltage holding ratio is lowered, and the polymerizable compound of the second component is less likely to locally concentrate on the substrate surface than the polar compound of the present application, and as a result, polymerization becomes insufficient, and the tilt forming ability is lowered.
From the above results, it was confirmed that these comparative examples failed to solve the problems of the present invention.
Further, the liquid crystal compositions of comparative examples 3 to 8 were also insufficient in voltage holding ratio and insufficient in amount of change in pretilt angle. Further, as in comparative example 9, when the amount of addition was increased, the unreacted monomer was also increased, and as a result, the voltage holding ratio was low, and further, the low-temperature storage property was lowered. From the above results, it was confirmed that comparative examples 1 to 9 could not solve the problems of the present invention.
Claims (7)
1. A liquid crystal composition comprising one or more compounds represented by the following formulae (Y-1-B3) to (Y-1-B6),
In the formula,
S y3b is a single bond or a straight-chain or branched alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with P y2b-Sy2b -or a fluorine atom, the alkylene group may be represented by-CH 2 -COO-; OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
P y2b represents formula (P-1) or formula (P-2),
[ Chemical 14]
Wherein, the black dots represent the bond with S y2b,
S y2b is a single bond or a straight chain alkylene group having 1 to 6 carbon atoms, hydrogen atoms in the alkylene group may be substituted with fluorine atoms, the-CH 2 -group in the alkylene group may be replaced by-COO-, OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
Z y1b and Z y2b each independently represent a single bond 、-C2H4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-、-CF2O-、-OCF2-、 or-C.ident.C-, wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms,
M y1b and M y3b each independently represent a group selected from the following formulae (A-1) to (A-8),
[ 16]
L y1b represents P y2b-Sy2b -, a fluorine atom, a chlorine atom, a cyano group, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, the-CH 2 -group in the alkyl group may be replaced by-COO-, OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
M b and n b each independently represent an integer of 0 to 2, wherein the total number of m+n is 0 to 2.
2. The liquid crystal composition according to claim 1, which contains 1 or 2 or more polymerizable compounds A having a structure different from that of the compound having the structure represented by the general formula (Y-1-B3) to (Y-1-B6) in the molecule.
3. The liquid crystal composition according to claim 2, wherein the polymerizable compound A is a compound represented by the general formula (P),
[ Chemical 5]
Wherein R p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or-Sp p2-Pp2, 1 or non-adjacent 2 or more-CH 2 -in the alkyl group may each independently be substituted with-CH=CH-, -C≡C-, -O-, -CO-, -COO-, or-OCO-, 1 or more hydrogen atoms in the alkyl group may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
P p1 and P p2 each independently represent any one of the general formulae (P p1 -1) to (P p1 -9),
[ Chemical 6]
Wherein R p11 and R p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, W p11 represents a single bond, -O-, -COO-, an alkylene group having 1 to 5 carbon atoms, t p11 represents 0, 1 or 2, and when a plurality of R p11、Rp12、Wp11 and/or t p11 are present in the molecule, they may be the same or different,
Sp p1 and Sp p2 each independently represent a single bond or a spacer,
Z p1 and Z p2 each independently represent a single bond 、-O-、-S-、-CH2-、-OCH2-、-CH2O-、-CO-、-C2H4-、-COO-、-OCO-、-OCOOCH2-、-CH2OCOO-、-OCH2CH2O-、-CO-NRZP1-、-NRZP1-CO-、-SCH2-、-CH2S-、-CH＝CRZP1-COO-、-CH＝CRZP1-OCO-、-COO-CRZP1＝CH-、-OCO-CRZP1＝CH-、-COO-CRZP1＝CH-COO-、-COO-CRZP1＝CH-OCO-、-OCO-CRZP1＝CH-COO-、-OCO-CRZP1＝CH-OCO-、-(CH2)z-COO-、-(CH2)z-OCO-、-OCO-(CH2)z-、-(C＝O)-O-(CH2)z-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF2-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2- or-C≡C-, wherein Z each independently represents an integer of 1 to 4, R ZP1 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and when a plurality of R ZP1 are present in the molecule, they may be the same or different, and in addition, wherein each represents a bonding point with Sp p1 or Sp p2,
A p1 and a p2 each independently represent a group selected from the group consisting of:
(a p) 1, 4-cyclohexylene, 1-CH 2 -or non-adjacent 2 or more-CH 2 -present in the group may be substituted by-O-;
(b p) 1, 4-phenylene, 1-CH=or more than 2-CH=which are not adjacent in the group can be substituted by-N=and
(C p) naphthalene-1, 4-diyl, naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl, phenanthrene-2, 7-diyl or anthracene-2, 6-diyl, 1-ch=or non-adjacent 2 or more-ch=groups present in these groups may be substituted by-n=and,
A p3 represents a group selected from the group consisting of the group (a p), the group (b p) and the group (c p) and a single bond,
In the group (a p), the group (b p) and the group (c p), the hydrogen atoms present in the groups may each independently be substituted with cyano groups, halogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 8 carbon atoms, alkenyl groups having 1 to 8 carbon atoms or-Sp p2-Pp2,
M p1 represents 0, 1,2 or 3, and in the case where a plurality of Z p1、Ap2、Spp2 and/or P p2 exist in the molecule, they may be the same or different.
4. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 3.
5. A liquid crystal display element for active matrix driving, which uses the liquid crystal composition according to any one of claims 1 to 3.
6. A liquid crystal display element for a PSA mode, a PSVA mode, a PS-IPS mode or a PS-FFS mode, using the liquid crystal composition of any one of claims 1 to 3.
7. A compound represented by the general formula (Y-1-B3) to the general formula (Y-1-B6),
In the formula,
S y3b is a single bond or a straight-chain or branched alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with P y2b-Sy2b -or a fluorine atom, the alkylene group may be represented by-CH 2 -COO-; OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
P y2b represents formula (P-1) or formula (P-2),
[ Chemical 14]
Wherein, the black dots represent the bond with S y2b,
S y2b is a single bond or a straight chain alkylene group having 1 to 6 carbon atoms, hydrogen atoms in the alkylene group may be substituted with fluorine atoms, the-CH 2 -group in the alkylene group may be replaced by-COO-, OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
Z y1b and Z y2b each independently represent a single bond 、-C2H4-、-OCH2-、-CH2O-、-COO-、-OCO-、-OCH2CH2O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COOC2H4-、-OCOC2H4-、-C2H4OCO-、-CH＝CH-、-CF2O-、-OCF2-、 or-C.ident.C-, wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms,
M y1b and M y3b each independently represent a group selected from the following formulae (A-1) to (A-8),
[ 16]
L y1b represents P y2b-Sy2b -, a fluorine atom, a chlorine atom, a cyano group, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, the-CH 2 -group in the alkyl group may be replaced by-COO-, OCO-or-O-substitution but more than 2-O-are not consecutive resulting in abutment,
M b and n b each independently represent an integer of 0 to 2, wherein the total number of m+n is 0 to 2.
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| CN112812012A (en) * | 2019-11-15 | 2021-05-18 | 石家庄诚志永华显示材料有限公司 | Compound, liquid crystal composition, liquid crystal display element, and liquid crystal display |
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| EP2574976B1 (en) * | 2004-04-30 | 2021-08-11 | Johnson & Johnson Surgical Vision, Inc. | Ophthalmic devices having a highly selective violet light transmissive filter |
| WO2010119779A1 (en) | 2009-04-14 | 2010-10-21 | Dic株式会社 | Liquid crystal composition containing polymerizable compound and liquid crystal display element using same |
| JP5743132B2 (en) | 2010-10-01 | 2015-07-01 | Dic株式会社 | Liquid crystal composition containing polymerizable compound and liquid crystal display device using the same |
| CN104893743A (en) | 2011-03-29 | 2015-09-09 | 默克专利股份有限公司 | Liquid-crystalline medium |
| CN111849508A (en) | 2014-12-25 | 2020-10-30 | Dic株式会社 | Nematic liquid crystal composition and liquid crystal display element using the same |
| EP3450523B1 (en) | 2016-04-27 | 2021-01-06 | DIC Corporation | Liquid crystal composition and liquid crystal display device |
| JP6493775B1 (en) * | 2017-06-29 | 2019-04-03 | Dic株式会社 | Liquid crystal composition and liquid crystal display device |
| CN110803983A (en) * | 2018-08-04 | 2020-02-18 | 石家庄诚志永华显示材料有限公司 | Compound, liquid crystal composition, liquid crystal display element and liquid crystal display |
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| CN1802409A (en) * | 2003-04-08 | 2006-07-12 | 西巴特殊化学品控股有限公司 | Light stabilising polymer dispersants in pigment dispersions |
| JP2007241148A (en) * | 2006-03-10 | 2007-09-20 | Fujifilm Corp | Colored curable composition, color filter and method for producing same |
| CN110804005A (en) * | 2018-08-04 | 2020-02-18 | 石家庄诚志永华显示材料有限公司 | Compound, liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN112812012A (en) * | 2019-11-15 | 2021-05-18 | 石家庄诚志永华显示材料有限公司 | Compound, liquid crystal composition, liquid crystal display element, and liquid crystal display |
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| JP2021161318A (en) | 2021-10-11 |
| CN113493690A (en) | 2021-10-12 |
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