KR20110113469A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents
Heterocyclic compound and organic light emitting device comprising the same Download PDFInfo
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- KR20110113469A KR20110113469A KR1020100032878A KR20100032878A KR20110113469A KR 20110113469 A KR20110113469 A KR 20110113469A KR 1020100032878 A KR1020100032878 A KR 1020100032878A KR 20100032878 A KR20100032878 A KR 20100032878A KR 20110113469 A KR20110113469 A KR 20110113469A
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- South Korea
- Prior art keywords
- formula
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- carbon atoms
- light emitting
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 238000002347 injection Methods 0.000 claims description 28
- 239000007924 injection Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 230000000903 blocking effect Effects 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000005647 linker group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 238000000151 deposition Methods 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000005286 illumination Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 41
- 230000000694 effects Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 81
- 230000015572 biosynthetic process Effects 0.000 description 43
- 238000003786 synthesis reaction Methods 0.000 description 43
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 20
- -1 sec-butyloxy group Chemical group 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001975 deuterium Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 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 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- VTSDGYDTWADUJQ-UHFFFAOYSA-N 2-bromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 VTSDGYDTWADUJQ-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- CUHHSFGWLKGXDX-UHFFFAOYSA-N 5-chloro-4,6-diphenyltriazine Chemical compound ClC1=C(C=2C=CC=CC=2)N=NN=C1C1=CC=CC=C1 CUHHSFGWLKGXDX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QJFMLQKNUKESAL-UHFFFAOYSA-N C(C1)C=Cc2c1c(cccc1)c1c(N(c1c3cccc1)c1ccccc1C3(c1ccccc1C1)c(cc3c4c5cccc4)c1cc3[n]5-c1nc(-c3ccccc3)nc(-c3ccccc3)n1)c2 Chemical compound C(C1)C=Cc2c1c(cccc1)c1c(N(c1c3cccc1)c1ccccc1C3(c1ccccc1C1)c(cc3c4c5cccc4)c1cc3[n]5-c1nc(-c3ccccc3)nc(-c3ccccc3)n1)c2 QJFMLQKNUKESAL-UHFFFAOYSA-N 0.000 description 1
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- GOOJGVFMVYVLNJ-UHFFFAOYSA-N CC1C=NC(c2cccc(N3c4cc(Cc5ccccc5C56c7ccccc7N(c7ccccc7)c7c5cccc7)c6cc4C4=CC=CCC34)n2)=NC1 Chemical compound CC1C=NC(c2cccc(N3c4cc(Cc5ccccc5C56c7ccccc7N(c7ccccc7)c7c5cccc7)c6cc4C4=CC=CCC34)n2)=NC1 GOOJGVFMVYVLNJ-UHFFFAOYSA-N 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical class COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
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- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
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- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D209/56—Ring systems containing three or more rings
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Abstract
본 발명은 신규한 이형고리 화합물 및 이를 발광물질로 포함하는 유기전계 발광소자에 관한 것으로서, 구체적으로 하기 [화학식 1]로 표시되는 이형고리 화합물 및 이를 포함하는 유기전계발광소자는 구동전압, 전류효율 등의 발광특성에 있어 우수한 효과가 있다.
[화학식 1]
[Formula 1]
Description
본 발명은 신규한 이형고리 화합물 및 이를 발광물질로 포함하는 유기전계발광소자에 관한 것으로서, 보다 상세하게는 구동전압, 전류효율 등의 발광특성이 우수하고 안정적인 이형고리 화합물 및 이를 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same as a light emitting material, and more particularly, a stable heterocyclic compound having excellent luminescent properties such as driving voltage and current efficiency and an organic electroluminescent light containing the same. It relates to an element.
최근 표시장치의 대형화에 따라 공간 점유가 작은 평면표시소자의 요구가 증대되고 있는데, 대표적인 평면표시소자인 액정 디스플레이는 기존의 CRT(cathode ray tube)에 비해 경량화가 가능하다는 장점은 있으나, 시야각(viewing angle)이 제한되고 배면 광(back light)이 반드시 필요하다는 등의 단점을 갖고 있다. 이에 반하여, 새로운 평면표시소자인 유기전계발광소자(organic light emitting diode, OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고, 액정 디스플레이에 비해 경박, 단소해질 수 있으며, 빠른 응답 속도 등의 장점을 가지고 있으며, 최근에는 풀-컬러(full-color) 디스플레이 또는 조명으로의 응용이 기대되고 있다.Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT). The disadvantage is that the angle is limited and the back light is necessary. In contrast, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays using self-luminous phenomena, and have a large viewing angle, are thinner and shorter than liquid crystal displays, and have fast response speeds. In recent years, the application to full-color display or lighting is expected.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다.In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
유기 발광 현상을 이용하는 유기전계발광소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전계발광소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기전계발광소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기전계발광소자는 자발광, 고휘도, 고효율, 낮은 구동전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such organic light emitting diodes are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
유기전계발광소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트-도판트 시스템을 사용할 수 있다.On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.
그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때, 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
유기전계발광소자가 전술한 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전계발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 당 기술분야에서는 새로운 재료의 개발이 계속 요구되고 있는 실정이다.In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials in the art continues to be required.
본 발명이 이루고자 하는 기술적 과제는 구동전압이 낮고 발광효율이 우수한 특성을 갖는 신규한 이형고리 화합물을 제공하는 것이다.The technical problem to be achieved by the present invention is to provide a novel release ring compound having a low driving voltage and excellent luminous efficiency.
본 발명이 이루고자 하는 두 번째 기술적 과제는 상기 이형고리 화합물을 포함하는 유기전계발광소자를 제공하는 것이다.The second technical problem to be achieved by the present invention is to provide an organic electroluminescent device comprising the heterocyclic compound.
상기 첫 번째 기술적 과제를 달성하기 위해서, 본 발명은 하기 [화학식 1]로 표시되는 화합물을 제공한다.In order to achieve the first technical problem, the present invention provides a compound represented by the following [Formula 1].
[화학식 1][Formula 1]
상기 식에서,Where
A1 및 A2 중 적어도 하나는 상기 [화학식 1]의 임의의 두 개의 탄소와 결합하여 축합환을 형성하는 것을 특징으로 하고,At least one of A 1 and A 2 is characterized in that combined with any two carbon of [Formula 1] to form a condensed ring,
R1 내지 R8은 각각 독립적으로 수소원자, 중수소원자, 할로겐원자, 치환 또는 비치환의 탄소수 6 내지 40의 아릴아미노기, 치환 또는 비치환의 탄소수 3 내지 40의 아릴옥시기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로아릴기, 게르마늄기, 인, 보론으로 이루어지는 군에서 선택되며,R 1 R 8 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 40 carbon atoms, a substituted or unsubstituted C 6 to 40 carbon atom An aryl group, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron;
L은 단결합 또는 2가의 연결기로서,L is a single bond or a divalent linking group,
2가의 연결기인 경우 치환 또는 비치환의 탄소수 1 내지 10의 알킬렌기, 치환 또는 비치환의 탄소수 2 내지 10의 알케닐기, 치환 또는 비치환의 탄소수 2 내지 40의 알키닐기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로아릴기로 이루어지는 군에서 선택되고,A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon group having 6 to 40 carbon atoms An aryl group, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,
X는 O, S 및 SiR9R10으로 이루어지는 군에서 선택되며, R9 및 R10은 상기 R1 내지 R8의 정의와 동일하다.X is selected from the group consisting of O, S and SiR 9 R 10 , R 9 And R 10 is the R 1 To R 8 .
n은 0 또는 1의 정수이다.n is an integer of 0 or 1.
본 발명은 상기 두 번째 기술적 과제를 달성하기 위해서, 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되는 발광층에서, 발광층이 상기 [화학식 1]로 표시되는 이형고리 화합물을 포함하는 유기전계발광소자를 제공한다.The present invention, in order to achieve the second technical problem, an anode; Cathode; And in the light emitting layer interposed between the anode and the cathode, the light emitting layer provides an organic electroluminescent device comprising a heterocyclic compound represented by the above [Formula 1].
본 발명에 따르면, [화학식 1]로 표시되는 이형고리 화합물은 기존 물질에 비하여 안정적이고 우수한 발광 특성을 가지므로 이를 포함한 유기전계발광소자는 저전압 구동이 가능하고 발광효율을 개선시킬 수 있다.According to the present invention, since the heterocyclic compound represented by [Formula 1] has a stable and excellent light emission characteristics compared to the conventional material, the organic light emitting device including the same can be driven at low voltage and improve the light emission efficiency.
도 1은 본 발명의 일 구체예에 따른 유기전계발광소자의 개략도이다.
<도면의 주요부분에 대한 부호의 설명>
10 : 기판 20 : 애노드
30 : 정공주입층 40 : 정공수송층
50 : 유기발광층 60 : 전자수송층
70 : 전자주입층 80 : 캐소드1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.
<Description of the symbols for the main parts of the drawings>
10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 이형고리 화합물로서 상기 [화학식 1]로 표시되는 것을 특징으로 한다.The present invention is characterized by being represented by the above [formula 1] as a heterocyclic compound.
본 발명에 따른 상기 [화학식 1]의 이형고리 화합물에 있어서, 그 치환기를 보다 구체적으로 설명하면 하기와 같다.In the heterocyclic compound of [Formula 1] according to the present invention, the substituent is described in more detail as follows.
상기 [화학식 1]에서, 치환기는 각각 독립적으로 중수소 원자, 시아노기, 할로겐 원자, 히드록시기, 니트로기, 탄소수 1 내지 40의 알킬기, 탄소수 1 내지 40의 알콕시기, 탄소수 1 내지 40의 알킬아미노기, 탄소수 6 내지 40의 아릴아미노기, 탄소수 3 내지 40의 헤테로아릴아미노기, 탄소수 1 내지 40의 알킬실릴기, 탄소수 6 내지 40의 아릴실릴기, 탄소수 6 내지 40의 아릴기, 탄소수 3 내지 40의 아릴옥시기, 탄소수 3 내지 40의 헤테로아릴기, 게르마늄기, 인 및 보론으로 이루어진 군으로부터 선택된 하나 이상의 치환기에 의해서 치환될 수 있고, 상기 치환기에 의해 추가로 치환될 수 있다.In [Formula 1], the substituents are each independently a deuterium atom, cyano group, halogen atom, hydroxy group, nitro group, alkyl group of 1 to 40 carbon atoms, alkoxy group of 1 to 40 carbon atoms, alkylamino group of 1 to 40 carbon atoms, carbon number Arylamino group having 6 to 40 carbon atoms, heteroarylamino group having 3 to 40 carbon atoms, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl group having 6 to 40 carbon atoms, aryl group having 6 to 40 carbon atoms, and aryloxy group having 3 to 40 carbon atoms , It may be substituted by one or more substituents selected from the group consisting of a heteroaryl group, a germanium group, phosphorous and boron having 3 to 40 carbon atoms, it may be further substituted by the substituent.
또한, 상기 치환기는 서로 결합하여 포화 혹은 불포화 고리인 지방족, 방향족, 헤테로지방족 또는 헤테로방향족의 축합고리를 형성할 수 있으며, 펜던트 방법으로 함께 부착되거나 또는 융합될 수 있다.In addition, the substituents may be bonded to each other to form a condensed ring of aliphatic, aromatic, heteroaliphatic or heteroaromatic which is a saturated or unsaturated ring, and may be attached or fused together by a pendant method.
본 발명에서 사용되는 치환기인 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소부틸기, sec-부틸기, tert-부틸기, 펜틸기, iso-아밀기, 헥실기, 헵틸기, 옥틸기, 스테아릴기, 트리클로로메틸기, 트리플루오르메틸기 등을 들 수 있으며, 상기 알킬기 중 하나 이상의 수소 원자는 중수소 원자, 할로겐 원자, 히드록시기, 니트로기, 시아노기, 트리플루오로메틸기, 실릴기(이 경우 "알킬실릴기"라 함), 치환 또는 비치환된 아미노기(-NH2,-NH(R),-N(R')(R''),여기서 R, R' 및 R"은 각각 독립적으로 탄소수 1 내지 24의 알킬기임(이 경우 "알킬아미노기"라 함)), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, 탄소수 1 내지 24의 알킬기, 탄소수 1 내지 24의 할로겐화된 알킬기, 탄소수 2 내지 24의 알케닐기, 탄소수 2 내지 24의 알키닐기, 탄소수 1 내지 24의 헤테로알킬기, 탄소수 5 내지 24의 아릴기, 탄소수 6 내지 24의 아릴알킬기, 탄소수 3 내지 24의 헤테로아릴기 또는 탄소수 3 내지 24의 헤테로아릴알킬기로 치환될 수 있다.Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, A stearyl group, a trichloromethyl group, a trifluoromethyl group, and the like, and at least one hydrogen atom of the alkyl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, or a silyl group (in this case, Alkylsilyl groups ", substituted or unsubstituted amino groups (-NH 2 , -NH (R),-N (R ') (R"), wherein R, R' and R "are each independently carbon An alkyl group of 1 to 24 (in this case referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group of 1 to 24 carbon atoms, a halogenated alkyl group of 1 to 24 carbon atoms , Alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, 1 carbon atom By more than 24 heteroaryl group, a heteroarylalkyl group having a carbon number of 5 to 24 aryl group, C 6 -C 24 aryl group, a C 3 -C 24 heteroaryl group, or having from 3 to 24 of which may be substituted.
본 발명의 화합물에서 사용되는 치환기인 알콕시기의 구체적인 예로는 메톡시기, 에톡시기, 프로폭시기, 이소부틸옥시기, sec-부틸옥시기, 펜틸옥시기, iso-아밀옥시기, 헥실옥시기 등을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group and the like. These can be mentioned and can substitute by the same substituent as the case of the said alkyl group.
본 발명의 화합물에서 사용되는 치환기인 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.
본 발명의 화합물에서 사용되는 치환기인 아릴기의 구체적인 예로는 페닐기, 2-메틸페닐기, 3-메틸페닐기, 4-메틸페닐기, 4-에틸페닐기, o-비페닐기, m-비페닐기, p-비페닐기, 4-메틸비페닐기, 4-에틸비페닐기, o-터페닐기, m-터페닐기, p-터페닐기, 1-나프틸기, 2-나프틸기, 1-메틸나프틸기, 2-메틸나프틸기, 안트릴기, 페난트릴기, 피레닐기, 플루오레닐기, 테트라히드로나프틸기 등과 같은 방향족 그룹을 들 수 있으며, 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the aryl group which is a substituent used in the compound of the present invention are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-ratio Phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group And an aromatic group such as an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a tetrahydronaphthyl group, and the like, and may be substituted with the same substituent as in the alkyl group.
본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기의 구체적인 예로는 피리디닐기, 피리미디닐기, 트리아지닐기, 인돌리닐기, 퀴놀린닐기, 피롤리디닐기, 피페리디닐기, 모폴리디닐기, 피페라디닐기, 카바졸릴기, 옥사졸릴기, 옥사디아졸릴기, 벤조옥사졸릴기, 치아졸릴기, 치아디아졸릴기, 벤조치아졸릴기, 트리아졸릴기, 이미다졸릴기, 벤조이미다졸기 등이 있으며, 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.Specific examples of the heteroaryl group which is a substituent used in the compound of the present invention include pyridinyl group, pyrimidinyl group, triazinyl group, indolinyl group, quinolinyl group, pyrrolidinyl group, piperidinyl group, morpholidinyl group, pipepe Radiinyl, carbazolyl, oxazolyl, oxdiazolyl, benzooxazolyl, chiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, imidazolyl and benzoimidazole At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group.
본 발명의 화합물에서 2가의 연결기인 L 중 알킬렌기는 상기 알킬기들에서 유도된 2가의 연결기로서 탄소수 1 내지 10의 알킬렌기이고, 알킬렌기 중 하나 이상의 수소는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.In the compound of the present invention, the alkylene group in L which is a divalent linking group is a divalent linking group derived from the alkyl groups, and is an alkylene group having 1 to 10 carbon atoms, and at least one hydrogen in the alkylene group may be substituted with the same substituent as in the alkyl group. Do.
본 발명의 화합물에서 2가의 연결기인 L 중 헤테로아릴기는 상기 헤테로 아릴기들에서 유도된 2가의 연결기로서 탄소수 3 내지 40의 헤테로아릴기이며, 헤테로아릴기 중 하나 이상의 수소는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.In the compound of the present invention, the heteroaryl group in L, which is a divalent linking group, is a heteroaryl group having 3 to 40 carbon atoms as a divalent linking group derived from the heteroaryl groups, and at least one hydrogen of the heteroaryl group is the same substituent as in the alkyl group. It is possible to substitute by.
본 발명의 화합물에서 2가의 연결기인 L 중 아릴기는 상기 아릴기들에서 유도된 2가의 연결기로서 탄소수 6 내지 40의 아릴기이며, 아릴기 중 하나 이상의 수소는 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.In the compound of the present invention, the aryl group in L which is a divalent linking group is a divalent linking group derived from the aryl groups and is an aryl group having 6 to 40 carbon atoms, and at least one hydrogen of the aryl group may be substituted with the same substituent as in the alkyl group. .
본 발명의 화합물에서 2가의 연결기인 L 중 알케닐기는 선형, 분지형 또는 탄소수 3 내지 10의 시클로알케닐기일 수 있고, 1-메틸-n-헥세닐, 1,2-디메틸 -n-헥세닐, 1-에틸-n-헥세닐, 1-n-헵테닐, 2-n-헵테닐, 3-n-헵테닐, 4-n-헵테닐, 1-n-옥테닐, 2-n-옥테닐, 3-n-옥테닐, 1-메틸-c-헥세닐, 1,2-디메틸-c-헥세닐, 1-에틸-c-헥세닐, 1-c-헵테닐, 2-c-헵테닐, 3-c-헵테닐, 4-c-헵테닐, 1-c-옥테닐, 2-c-옥테닐, 3-c-옥테닐, 4-c-옥테닐 등일 수 있으며, 상기 알킬기의 경우와 동일한 치환기로 치환가능하다.The alkenyl group in L which is a divalent linking group in the compound of the present invention may be a linear, branched or cycloalkenyl group having 3 to 10 carbon atoms, and may be 1-methyl-n-hexenyl, 1,2-dimethyl-n-hexenyl , 1-ethyl-n-hexenyl, 1-n-heptenyl, 2-n-heptenyl, 3-n-heptenyl, 4-n-heptenyl, 1-n-octenyl, 2-n-jade Tenyl, 3-n-octenyl, 1-methyl-c-hexenyl, 1,2-dimethyl-c-hexenyl, 1-ethyl-c-hexenyl, 1-c-heptenyl, 2-c-hep Tenyl, 3-c-heptenyl, 4-c-heptenyl, 1-c-octenyl, 2-c-octenyl, 3-c-octenyl, 4-c-octenyl, and the like. Substituent with the same substituent as the case may be sufficient.
또한, 알키닐기는 탄소수 2 내지 40의 직쇄상, 분지쇄상 또는 환상 중 어느 하나일 수 있고, 에티닐기, 1-프로피닐기, 2-프로피닐기, 2-부티닐기 등을 들 수 있으며 상기 알킬기의 경우와 같이 알키닐기 중 하나 이상의 수소는 동일한 치환기로 치환가능하다.In addition, the alkynyl group may be any one of linear, branched or cyclic having 2 to 40 carbon atoms, and may include an ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, and the like. One or more hydrogen of the alkynyl group as described above may be substituted with the same substituent.
본 발명에 있어서, "치환 또는 비치환된"이라는 용어는 시아노기, 할로겐기, 히드록시기, 니트로기, 알킬렌기, 알케닐기, 알키닐기, 알킬기, 알콕시기, 알킬아미노기, 아릴아미노기, 헤케로아릴아미노기, 알킬실릴기, 아릴실릴기, 아릴옥시기, 아릴기, 헤테로아릴기, 게르마늄, 인, 보론, 수소 및 중수소로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되는 것을 의미한다.In the present invention, the term "substituted or unsubstituted" is cyano group, halogen group, hydroxy group, nitro group, alkylene group, alkenyl group, alkynyl group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group It means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of, alkylsilyl group, arylsilyl group, aryloxy group, aryl group, heteroaryl group, germanium, phosphorus, boron, hydrogen and deuterium.
상술한 바와 같은 구조를 갖는 상기 [화학식 1]의 임의의 두 개의 탄소와 A1및 A2 중 적어도 하나가 결합하여 축합환을 형성한다.Any two carbons of [Formula 1] having the structure as described above and at least one of A 1 and A 2 combine to form a condensed ring.
상술한 바와 같은 구조를 갖는 상기 [화학식 1]에 따른 이형고리 화합물에 대한 구체적인 예에 의해서 본 발명이 제한되는 것은 아니지만, 구체적으로 하기 [화학식 2] 내지 [화학식 88]로 표시되는 화합물 중 어느 하나일 수 있다.Although the present invention is not limited by the specific examples of the heterocyclic compound according to [Formula 1] having the structure as described above, specifically, any one of the compounds represented by the following [Formula 2] to [Formula 88] Can be.
[화학식 2] [화학식 3] [화학식 4][Formula 2] [Formula 3] [Formula 4]
[화학식 5] [화학식 6] [화학식 7][Formula 5] [Formula 6] [Formula 7]
[화학식 8] [화학식 9] [화학식 10][Formula 8] [Formula 9] [Formula 10]
[화학식 11] [화학식 12] [화학식 13][Formula 11] [Formula 12] [Formula 13]
[화학식 14] [화학식 15] [화학식 16][Formula 14] [Formula 15] [Formula 16]
[화학식 17] [화학식 18] [화학식 19][Formula 17] [Formula 18] [Formula 19]
[화학식 20] [화학식 21] [화학식 22][Formula 20] [Formula 21] [Formula 22]
[화학식 23] [화학식 24] [화학식 25][Formula 23] [Formula 24] [Formula 25]
[화학식 26] [화학식 27] [화학식 28][Formula 26] [Formula 27] [Formula 28]
[화학식 29] [화학식 30] [화학식 31][Formula 29] [Formula 30] [Formula 31]
[화학식 32] [화학식 33] [화학식 34][Formula 32] [Formula 33] [Formula 34]
[화학식 35] [화학식 36] [화학식 37][Formula 35] [Formula 36] [Formula 37]
[화학식 38] [화학식 39] [화학식 40][Formula 38] [Formula 39] [Formula 40]
[화학식 41] [화학식 42] [화학식 43][Formula 41] [Formula 42] [Formula 43]
[화학식 44] [화학식 45] [화학식 46][Formula 44] [Formula 45] [Formula 46]
[화학식 47] [화학식 48] [화학식 49][Formula 47] [Formula 48] [Formula 49]
[화학식 50] [화학식 51] [화학식 52][Formula 50] [Formula 51] [Formula 52]
[화학식 53] [화학식 54] [화학식 55][Formula 53] [Formula 54] [Formula 55]
[화학식 56] [화학식 57] [화학식 58][Formula 56] [Formula 57] [Formula 58]
[화학식 59] [화학식 60] [화학식 61][Formula 59] [Formula 60] [Formula 61]
[화학식 62] [화학식 63] [화학식 64][Formula 62] [Formula 63] [Formula 64]
[화학식 65] [화학식 66] [화학식 67][Formula 65] [Formula 66] [Formula 67]
[화학식 68] [화학식 69] [화학식 70][Formula 68] [Formula 69] [Formula 70]
[화학식 71] [화학식 72] [화학식 73][Formula 71] [Formula 72] [Formula 73]
[화학식 74] [화학식 75] [화학식 76][Formula 74] [Formula 75] [Formula 76]
[화학식 77] [화학식 78] [화학식 79][Formula 77] [Formula 78] [Formula 79]
[화학식 80] [화학식 81] [화학식 82][Formula 80] [Formula 81] [Formula 82]
[화학식 83] [화학식 84] [화학식 85][Formula 83] [Formula 84] [Formula 85]
[화학식 86] [화학식 87] [화학식 88][Formula 86] [Formula 87] [Formula 88]
본 발명에 따른 이형고리 화합물의 제조방법은 후술하는 실시예에 구체적으로 나타내었다.The preparation method of the heterocyclic compound according to the present invention is shown in detail in the following Examples.
또한, 본 발명은 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 이형고리 화합물을 포함하는 층을 구비한 유기전계발광소자를 제공한다.In addition, the present invention is an anode; Cathode; And it is interposed between the anode and the cathode, and provides an organic light emitting device having a layer containing a heterocyclic compound represented by the above [Formula 1].
이 때, 상기 이형고리 화합물이 포함된 층은 상기 애노드 및 캐소드 사이의 발광층인 것이 바람직하며, 애노드 및 캐소드 사이에는 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있다.At this time, the layer containing the heterocyclic compound is preferably a light emitting layer between the anode and the cathode, and the hole injection layer, the hole transport layer, the electron blocking layer, the hole blocking layer, the electron transport layer and the electron injection layer between the anode and the cathode It may further include one or more layers selected from the group consisting of.
또한, 본 발명의 다른 일 실시예에 의하면, 상기 발광층의 두께는 50 내지 2,000 Å인 것이 바람직하며, 상기 발광층은 하기 구조식의 물질을 추가로 포함할 수 있다.In addition, according to another embodiment of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa, and the light emitting layer may further include a material of the following structural formula.
[Ir(ppy)3][Ir (ppy) 3 ]
[Ir(chpy)3][Ir (chpy) 3 ]
[Ir(mchpy)3][Ir (mchpy) 3 ]
구체적인 예로서, 정공수송층(HTL, Hole Transport Layer)이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층(ETL, Electron Trans port Layer)이 추가로 적층되어 있는 것일 수 있는데, 상기 정공수송층은 애노드로부터 정공을 주입하기 쉽게 하기 위하여 적층되는 것으로서, 상기 정공수송층의 재료로는 이온화 포텐셜이 작은 전자공여성 분자가 사용되는데, 주로 트리페닐아민을 기본 골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다.As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The transport layer is laminated to facilitate the injection of holes from the anode. As the material of the hole transport layer, electron donating molecules having a small ionization potential are used. A diamine, triamine or tetraamine derivative mainly based on triphenylamine is used. Is used a lot.
본 발명에서도 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는 것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐벤지딘(a-NPD) 등을 사용할 수 있다.The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1 , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD) can be used.
상기 정공수송층의 하부에는 정공주입층(HIL, Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 CuPc(copper phthalocyanine) 또는 스타버스트(Starburst)형 아민류인 TCTA(4,4',4''-tri(N -carbazolyl)triphenyl-amine), m-MTDATA(4,4',4''-tris-(3-methylphenylphenyl amino)triphenylamine) 등을 사용할 수 있다.A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. TCP (4,4 ', 4' '-tri (N -carbazolyl) triphenyl-amine), for example, copper phthalocyanine (CuPc) or starburst amines, m-MTDATA (4,4', 4 ''- tris- (3-methylphenylphenyl amino) triphenylamine) may be used.
또한, 본 발명에 따른 유기전계발광소자에 사용되는 상기 전자수송층은 캐소드로부터 공급된 전자를 유기발광층으로 원활히 수송하고 상기 유기발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다.In addition, the electron transport layer used in the organic electroluminescent device according to the present invention has the opportunity to recombine in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes not bonded in the organic light emitting layer. Serves to increase.
상기 전자수송층 재료로는 당 기술분야에서 통상적으로 사용되는 것이면 특별히 제한되지 않고 사용할 수 있음은 물론이며, 예를 들어 옥사디아졸 유도체인 PBD, BMD, BND 또는 Alq3등을 사용할 수 있다.The electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and for example, oxadiazole derivatives such as PBD, BMD, BND or Alq 3 may be used.
한편, 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선시키는 기능을 수행하는 전자주입층(EIL, Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예를 들어, LiF, NaCl, CsF, Li2O,BaO등의 물질을 이용할 수 있다.Meanwhile, an electron injection layer (EIL) may be further stacked on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, materials such as LiF, NaCl, CsF, Li 2 O, BaO and the like can be used.
본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자 등에 사용될 수 있다.The organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.
도 1은 본 발명의 유기전계발광소자의 구조를 나타내는 단면도이다. 본 발명에 따른 유기전계발광소자는 애노드(20), 정공수송층(40), 유기발광층(50), 전자수송층(60) 및 캐소드(80)을 포함하며, 필요에 따라 정공주입층(30)과 전자주입층(70)을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다.1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting device according to the present invention includes an
도 1을 참조하여 본 발명의 유기전계발광소자 및 그 제조방법에 대하여 살펴보면 다음과 같다. 먼저 기판(10) 상부에 애노드 전극용 물질을 코팅하여 애노드(20)를 형성한다. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2),산화아연(ZnO) 등을 사용한다.Referring to Figure 1 with respect to the organic light emitting device and a method of manufacturing the present invention are as follows. First, the
상기 애노드(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다.The
이어서, 상기 정공수송층(40)의 상부에 유기발광층(50)을 적층하고 상기 유기발광층(50)의 상부에 선택적으로 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO(Highest Occupied Molecular Orbital) 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이 때, 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI 등이 사용될 수 있다.Subsequently, the organic
이러한 정공저지층 위에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층(70)을 형성하고 상기 전자주입층(70)의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드(80) 전극을 형성함으로써 유기 EL 소자가 완성된다. 여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다.After the
또한, 본 발명의 다른 일 실시예에 의하면, 상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성될 수 있으며, 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 사용될 수 있다.According to another embodiment of the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is a single molecule deposition method or a solution process The organic light emitting display device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 더욱 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않는다는 것은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.
<실시예><Examples>
<합성예 1> [화학식 2]로 표시되는 화합물의 합성Synthesis Example 1 Synthesis of Compound Represented by Formula 2
(1) [화학식 1-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 1-a]
하기 [반응식 1]에 의하여 [화학식 1-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-a] was synthesized by the following [Scheme 1].
[반응식 1]Scheme 1
[화학식 1-a] [Formula 1-a]
1000ml 둥근 바닥 플라스크에 2-브로모안트라퀴논 100.0g(0.35mmol)과 틴클로라이드 272.2g(1.04mmol)과 12M 염산용액 25ml와 초산 150ml를 넣고 환류시킨다. 반응물을 차갑게 식힌 후에 물로 묽힌 후, 탄산수소나트륨 용액으로 중화시킨다. 메틸렌 클로라이드로 추출하고, 마그네슘 설페이트로 수분을 제거한다. 헥산과 메틸렌클로라이드를 전개 용매로 사용하여 컬럼크로마토그래피로 분리하고 고체를 건조하여 [화학식 1-a]로 표시되는 화합물 45.12g을 얻었다. (수율 47.2%)100.0 g (0.35 mmol) of 2-bromoanthraquinone, 272.2 g (1.04 mmol) of tin chloride, 25 ml of 12M hydrochloric acid solution and 150 ml of acetic acid were refluxed in a 1000 ml round bottom flask. The reaction is cooled, diluted with water, and then neutralized with sodium bicarbonate solution. Extract with methylene chloride and remove moisture with magnesium sulfate. Hexane and methylene chloride were used as the developing solvent, and the residue was separated by column chromatography, and the solid was dried to obtain 45.12 g of the compound represented by [Formula 1-a]. (Yield 47.2%)
(2) [화학식 1-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by [Formula 1-b]
하기 [반응식 2]에 의하여 [화학식 1-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-b] was synthesized by the following [Scheme 2].
[반응식 2]Scheme 2
[화학식 1-a] [화학식 1-b] [Formula 1-a] [Formula 1-b]
1000ml 둥근 바닥 플라스크에 상기 [반응식 1]로부터 얻은 [화학식 1-a]로 표시되는 화합물을 넣은 후 비스(피나코레이토)디보론 46.1g(0.182mmol), PdCl2 (dppf)2.7g(0.003mmol), 칼륨 아세테이트 32.4g(0.33mmol)와 톨루엔 450ml을 넣고 12시간 환류시킨다. 반응이 종결되면 온도를 상온으로 내리고 톨루엔과 물을 사용해 추출을 실시한다. 유기층을 감압농축후 헥산과 염화메틸렌을 전개용매로 사용하여 컬럼크로마토그래피로 분리하고 고체를 건조하여 [화학식 1-b]로 표시되는 화합물 28.6g을 얻었다. (수율 54.2%)Into a 1000 ml round bottom flask, the compound represented by [Formula 1-a] obtained from [Scheme 1] was added, followed by 46.1 g (0.182 mmol) of bis (pinacoreto) diboron and PdCl 2 (dppf) 2.7 g (0.003 mmol), potassium acetate 32.4 g (0.33 mmol) and 450 ml of toluene were added and refluxed for 12 hours. When the reaction is completed, the temperature is lowered to room temperature and extraction is performed using toluene and water. The organic layer was concentrated under reduced pressure, separated by column chromatography using hexane and methylene chloride as a developing solvent, and dried to obtain 28.6 g of a compound represented by [Formula 1-b]. (Yield 54.2%)
(3) [화학식 1-c]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by [Formula 1-c]
하기 [반응식 3]에 의하여 [화학식 1-c]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-c] was synthesized by the following [Scheme 3].
[반응식 3]Scheme 3
[화학식 1-b] [화학식 1-c] [Formula 1-b] [Formula 1-c]
500ml 둥근 바닥 플라스크에 상기 [반응식 1] 및 [반응식 2]로부터 얻은 [화학식 1-b]로 표시되는 화합물을 넣은 후 2-브로모니트로벤젠 36.1g(0.179mmol), Pd(pph3)4 2.1g(0.002mmol)을 넣고 톨루엔 140ml을 넣는다.Into a 500 ml round bottom flask, the compound represented by [Formula 1-b] obtained from the above [Scheme 1] and [Scheme 2] was added, and then 2-bromonitrobenzene 36.1 g (0.179 mmol) and Pd (pph 3 ) 4 2.1 Add g (0.002 mmol) and add 140 ml of toluene.
칼륨 카보네이트 24.7g(0.179mmol)을 넣고 다이옥산 140ml와 물 60ml를 넣고 12시간 환류시킨다. 반응이 종결되면 반응물을 감압하여 고체를 얻는다. 뜨거운 아세톤으로 세척하고 건조하여 [화학식 1-c]로 표시되는 화합물23.67g을 얻었다. (수율 84.3%)Add 24.7 g (0.179 mmol) of potassium carbonate, add 140 ml of dioxane and 60 ml of water, and reflux for 12 hours. At the end of the reaction the reaction is depressurized to give a solid. It was washed with hot acetone and dried to obtain 23.67 g of a compound represented by [Formula 1-c]. (Yield 84.3%)
(4) [화학식 1-d]로 표시되는 화합물의 합성(4) Synthesis of Compound Represented by [Formula 1-d]
하기 [반응식 4]에 의하여 [화학식 1-d]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-d] was synthesized by the following [Scheme 4].
[반응식 4]Scheme 4
[화학식 1-c] [화학식 1-d] [Formula 1-c] [Formula 1-d]
1000ml 둥근 바닥 플라스크에 상기 [반응식 1], [반응식 2] 및 [반응식 3]으로부터 얻은 [화학식 1-c]로 표시되는 화합물을 넣은 후 트리페닐포스핀 119 g(0.454mmol)을 넣고 1,2-디클로로벤젠 580ml을 넣고 12시간 환류시킨다.Into a 1000 ml round bottom flask was added the compound represented by [Scheme 1-c] obtained from the above [Scheme 1], [Scheme 2] and [Scheme 3], and then 119 g (0.454 mmol) of triphenylphosphine was added. Add 580 ml of dichlorobenzene and reflux for 12 hours.
반응이 종결되면 뜨거운 상태로 감압필터하고 여액을 1,2-디클로로벤젠과 아세톤을 이용하여 재결정하고 고체를 건조하여 [화학식 1-d]로 표시되는 화합물 14.60g을 얻었다. (수율 56.8%)When the reaction was terminated under reduced pressure filter to hot state, the filtrate was recrystallized using 1,2-dichlorobenzene and acetone, and the solid was dried to obtain 14.60 g of the compound represented by [Formula 1-d]. (Yield 56.8%)
(5) [화학식 1-e]로 표시되는 화합물의 합성(5) Synthesis of Compound Represented by [Formula 1-e]
하기 [반응식 5]에 의하여 [화학식 1-e]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-e] was synthesized by the following [Scheme 5].
[반응식 5]Scheme 5
[화학식 1-d] [화학식 1-e] [Formula 1-d] [Formula 1-e]
1000ml 둥근 바닥 플라스크에 상기 [반응식 1], [반응식 2], [반응식 3] 및 [반응식 4]로부터 얻은 [화학식 1-d]로 표시되는 화합물 14.60g(0.052mol)과 아이오도벤젠 21.22g(0.104mol), 탄산칼륨 42.7g(0.309mol), 구리 9.8g(0.16mol), 18-crowon-6 6.8g(0.026mol)과 자일렌 300ml을 넣고 2일 동안 환류시킨다.In a 1000 ml round bottom flask, 14.60 g (0.052 mol) of compound represented by [Formula 1-d] obtained from [Scheme 1], [Scheme 2], [Scheme 3] and [Scheme 4] and 21.22 g of iodobenzene ( 0.104 mol), 42.7 g (0.309 mol) of potassium carbonate, 9.8 g (0.16 mol) of copper, 6.8 g (0.026 mol) of 18-crowon-6 and 300 ml of xylene were added and refluxed for 2 days.
반응이 종료되면 반응물을 식히고, 반응 종료 후 온도를 실온으로 내리고 물과 에틸아세테이트 이용하여 유기층을 분리하고 감압 농축한 후 헥산과 에틸아세테이트을 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 고체를 건조하여 [화학식 1-e]로 표시되는 화합물 9.5g을 얻었다. (수율35.5%)After the reaction is completed, the reaction mixture is cooled, and after completion of the reaction, the temperature is decreased to room temperature, the organic layer is separated using water and ethyl acetate, concentrated under reduced pressure, and separated by column chromatography using hexane and ethyl acetate as a developing solvent, and the solid is dried [ 9.5 g of a compound represented by Chemical Formula 1-e] was obtained. (Yield 35.5%)
(6) [화학식 1-f]로 표시되는 화합물의 합성(6) Synthesis of Compound Represented by Formula 1-f
하기 [반응식 6]에 의하여 [화학식 1-f]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-f] by the following [Scheme 6] was synthesized.
[반응식 6]Scheme 6
[화학식 1-f] [Formula 1-f]
2000ml 둥근 바닥 플라스크에 다이페닐아민 50.0g(0.295mol)과 브로모메틸메틸에테르 38.10ml(0.443mol)를 테트라하이드로퓨란 1000ml에 녹인 후 트리에틸아민 44.85g(0.443mol)을 천천히 적가시키고, 질소 기류하에서 5시간 교반 후 물과 테트라하이드로퓨란을 이용하여 유기층을 분리하고 감압 농축한 후 헥산과 테트라하이드로퓨란을 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 고체를 건조하여 [화학식 1-f]로 표시되는 화합물 53.3g을 얻었다. (수율 84.6%)In a 2000 ml round bottom flask, 50.0 g (0.295 mol) of diphenylamine and 38.10 ml (0.443 mol) of bromomethylmethyl ether were dissolved in 1000 ml of tetrahydrofuran, and 44.85 g (0.443 mol) of triethylamine was slowly added dropwise, followed by nitrogen stream. After stirring for 5 hours, the organic layer was separated using water and tetrahydrofuran, concentrated under reduced pressure, and separated by column chromatography using hexane and tetrahydrofuran as a developing solvent. The solid was dried and represented by [Formula 1-f]. 53.3 g of the resulting compound was obtained. (Yield 84.6%)
(7) [화학식 1-g]로 표시되는 화합물의 합성(7) Synthesis of Compound Represented by [Formula 1-g]
하기 [반응식 7]에 의하여 [화학식 1-g]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 1-g] was synthesized by the following [Scheme 7].
[반응식 7] Scheme 7
[화학식 1-f] [화학식 1-e] [화학식 1-g][Formula 1-f] [Formula 1-e] [Formula 1-g]
500ml 둥근 바닥 플라스크에 상기 [반응식 6]으로부터 얻은 [화학식 1-f]로 표시되는 3.8g(0.047mol)을 테트라하이드로퓨란 40ml에 녹인 후 질소 상태하에서 30분간 교반을 시키고 반응물의 온도를 -78℃까지 내리고 1.6몰 헥산용액의 노말 부틸리튬 4.32ml을 1시간 동안 적가시킨다. 동일한 온도에서 1시간 동안 교반 후 상기 [반응식 5]로부터 얻은 [화학식 1-e]로 표시되는 화합물 9.5g(0.047mol)를 테트라하이드로퓨란 20ml에 녹이고 천천히 적가시킨다. 동일한 온도에서 1시간 동안 교반 후 실온으로 온도를 올리고 5시간 동안 교반 후 암모늄 클로라이드 수용액과 에틸에테르 이용하여 유기층을 분리하고 감압 농축한 후 생성된 고체를 에탈올을 이용해 씻어주고 건조시킨다.In a 500 ml round bottom flask, 3.8 g (0.047 mol) represented by [Formula 1-f] obtained from [Scheme 6] was dissolved in 40 ml of tetrahydrofuran, stirred for 30 minutes under nitrogen, and the temperature of the reaction was -78 ° C. 4.32 ml of normal butyllithium in 1.6 mol hexane solution was added dropwise for 1 hour. After stirring for 1 hour at the same temperature, 9.5 g (0.047 mol) of the compound represented by [Formula 1-e] obtained from [Scheme 5] is dissolved in 20 ml of tetrahydrofuran and slowly added dropwise. After stirring for 1 hour at the same temperature, the temperature was raised to room temperature, and after stirring for 5 hours, the organic layer was separated using an aqueous ammonium chloride solution and ethyl ether, concentrated under reduced pressure, and the resulting solid was washed with ethanol and dried.
건조된 물질을 아세트산 20ml에 분산시키고 진한 황산 1ml를 천천히 적가한 후 5시간 동안 환류시킨다. 생성된 고체를 감압여과 후 물과 에탄올을 이용해 씻어준 후 에탄올을 이용해 재결정을 실시하고 얻은 고체를 건조하여 [화학식 1-g]로 표시되는 화합물 8.22g을 얻었다. (수율 89.5%)The dried material is dispersed in 20 ml of acetic acid and 1 ml of concentrated sulfuric acid is slowly added dropwise and refluxed for 5 hours. The resulting solid was filtered under reduced pressure, washed with water and ethanol, recrystallized with ethanol, and dried to obtain 8.22 g of the compound represented by [Formula 1-g]. (Yield 89.5%)
(8) [화학식 2]로 표시되는 화합물의 합성(8) Synthesis of Compound Represented by Formula 2
하기 [반응식 8]에 의하여 [화학식 2]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 2] was synthesized by the following [Scheme 8].
[반응식 8]Scheme 8
[화학식 1-g] [화학식 2] [Formula 1-g] [Formula 2]
500ml 둥근 바닥 플라스크에 상기 [반응식 7]로부터 얻은 [화학식 1-g]로 표시되는 화합물 8.22g(0.016mol)과 아이오도벤젠 6.6g(0.032mol), 탄산칼륨 4.4g (0.032mol), 요오드화구리 0.1g(0.002mol), 구리 0.1g(0.0032mol) 및 자일렌 250ml을 넣고 2일 동안 환류시켰다. 반응 종료 후 온도를 실온으로 내리고 물과 에틸아세테이트 이용하여 유기층을 분리하고 감압 농축한 후 헥산과 에틸아세테이트을 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 고체를 건조하여 [화학식 2]로 표시되는 화합물 4.95g을 얻었다. (수율 52.8%)In a 500 ml round bottom flask, 8.22 g (0.016 mol) of compound represented by [Formula 1-g] obtained from [Scheme 7], 6.6 g (0.032 mol) of iodobenzene, 4.4 g (0.032 mol) of potassium carbonate, and copper iodide 0.1g (0.002mol), 0.1g (0.0032mol) copper and 250ml of xylene were added and refluxed for 2 days. After the completion of the reaction, the temperature was lowered to room temperature, the organic layer was separated using water and ethyl acetate, concentrated under reduced pressure, and the solid obtained by column chromatography using hexane and ethyl acetate as a developing solvent was dried and the compound represented by [Formula 2]. 4.95 g was obtained. (Yield 52.8%)
MS(MALDI-TOF):m/z= 586.24 [M]+ MS (MALDI-TOF): m / z = 586.24 [M] +
EA(Elemental analysis) : 이론값 - C. 90.07 % ; H. 5.15 % ; N. 4.77 %Elemental analysis (EA): theoretical value-C. 90.07%; H. 5.15%; N. 4.77%
실제값 - C. 90.02 % ; H. 5.10% ; N. 4.88 % Found-C. 90.02%; H. 5.10%; N. 4.88%
<합성예 2> [화학식 44]로 표시되는 화합물의 합성Synthesis Example 2 Synthesis of Compound Represented by Chemical Formula 44
(1) [화학식 2-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 2-a]
하기 [반응식 9]에 의하여 [화학식 2-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 2-a] was synthesized by the following [Scheme 9].
[반응식 9]Scheme 9
[화학식 1-d] [화학식 2-a] [Formula 1-d] [Formula 2-a]
상기 합성예 1의 (5) [반응식 5]에 사용된 아이오도벤젠 대신 클로로다이페닐트리아진을 사용한 것을 제외하고는 상기 합성예 1의 (5) 합성방법과 동일한 방법으로 합성하여 [화학식 2-a]로 표시되는 화합물 9.5g을 얻었다. (수율 35.5%)Synthesis Example 1 was synthesized in the same manner as in Synthesis Example 1, except that chlorodiphenyltriazine was used instead of iodobenzene in Synthesis Example 1 (5). 9.5 g of the compound represented by a] was obtained. (Yield 35.5%)
(2) [화학식 2-b]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by [Formula 2-b]
하기 [반응식 10]에 의하여 [화학식 2-b]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 2-b] was synthesized by the following [Scheme 10].
[반응식 10]
[화학식 1-f] [화학식 2-a] [화학식 2-b] [Formula 1-f] [Formula 2-a] [Formula 2-b]
상기 합성예 1의 (7) [반응식 7]에 사용된 [화학식 1-e]로 표시되는 화합물 대신 [화학식 2-a]로 표시되는 화합물를 사용한 것을 제외하고는 합성예 1의 (7)과 동일한 합성 방법으로 합성하여 [화학식 2-b]로 표시되는 화합물 10.49g을 얻었다. (수율 87.5%)Synthesis Example 1 (7) The same as in Synthesis Example 1 (7) except that the compound represented by [Formula 2-a] was used instead of the compound represented by [Formula 1-e] used in [Scheme 7] It synthesize | combined by the synthesis method and obtained 10.49g of compound represented by [Formula 2-b]. (Yield 87.5%)
(3) [화학식 44]로 표시되는 화합물의 합성(3) Synthesis of Compound Represented by Formula (44)
하기 [반응식 11]에 의하여 [화학식 44]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 44] was synthesized by the following [Scheme 11].
[반응식 11]Scheme 11
[화학식 2-b] [화학식 44] [Formula 2-b] [Formula 44]
상기 합성예 1의 (8) [반응식 8]에서 사용된 [화학식 1-g]로 표시되는 화합물 대신 [화학식 2-b]로 표시되는 화합물을 사용한 것을 제외하고는 상기 합성예 1의 (8)과 동일한 합성방법으로 합성하여 [화학식 44]로 표시되는 화합물 10.26g을 얻었다. (수율 86.5%)Synthesis Example 1 (8) Except for using the compound represented by [Formula 2-b] instead of the compound represented by [Formula 1-g] used in [Scheme 8] of Synthesis Example 1 (8) Synthesis was carried out in the same manner as in the following to obtain 10.26 g of the compound represented by [Formula 44]. (Yield 86.5%)
MS(MALDI-TOF):m/z= 741.29 [M]+ MS (MALDI-TOF): m / z = 741.29 [M] +
EA(Elemental analysis) : 이론값 - C. 85.80 % ; H. 4.76 % ; N. 9.44 %Elemental analysis (EA): theoretical value-C. 85.80%; H. 4.76%; N. 9.44%
실제값 - C. 85.62 % ; H. 4.82 % ; N. 9.56 % Found-C. 85.62%; H. 4.82%; N. 9.56%
<합성예 3> [화학식 47]로 표시되는 화합물의 합성Synthesis Example 3 Synthesis of Compound Represented by Formula 47
하기 [반응식 12]에 의하여 [화학식 47]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 47] was synthesized by the following [Scheme 12].
[반응식 12][Reaction Scheme 12]
[화학식 2-b] [화학식 47] [Formula 2-b] [Formula 47]
상기 합성예 2의 (3) [반응식 12]에서 사용된 아이오도벤젠 대신 1-브로모 나프탈렌을 사용한 것을 제외하고는 상기 합성예 2의 (3)과 동일한 합성방법으로 합성하여 [화학식 47]로 표시되는 화합물 15.93g을 얻었다. (수율 87.5%)Synthesis Example 2 was synthesized by the same synthesis method as in Synthesis Example 2, except that 1-bromo naphthalene was used instead of iodobenzene in Synthesis Example 2 (3). 15.93 g of the displayed compound were obtained. (Yield 87.5%)
MS(MALDI-TOF):m/z= 777.29 [M]+ MS (MALDI-TOF): m / z = 777.29 [M] +
EA(Elemental analysis) : 이론값 - C. 86.46 % ; H. 4.53 % ; N. 9.00 %Elemental analysis (EA): theoretical value-C. 86.46%; H. 4.53%; N. 9.00%
실제값 - C. 86.28 % ; H. 4.60 % ; N. 9.12 % Found-C. 86.28%; H. 4.60%; N. 9.12%
<합성예 4> [화학식 52]로 표시되는 화합물의 합성Synthesis Example 4 Synthesis of Compound Represented by Formula 52
(1) [화학식 4-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 4-a]
하기 [반응식 13]에 의하여 [화학식 4-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 4-a] was synthesized by the following [Scheme 13].
[반응식 13]Scheme 13
[화학식 4-a] [Formula 4-a]
500ml 둥근 바닥 플라스크에 2-브로모플로레논 20.0g(0.061mol)과 3M 페닐마그네슘브로마이드 용액 19.57ml(0.122mol)을 넣는다. 3시간 동안 교반하고 물을 부어 중화하고 차갑게 식힌 후에 다이에틸 에테르를 이용하여 추출한다. 유기물을 마그네슘 설페이트를 처리하여 수분을 제거하고 감압필터 후 농축하여 건조한다. 건조된 고체를 벤젠에 녹이고, 황산을 넣은 후 3시간 동안 환류시킨다. 반응물을 차갑게 식힌 후, 탄산수소 나트륨을 넣어 중화시킨다. 클로로폼으로 추출하고, 마그네슘 설페이트로 수분을 제거한 후 감압 필터하여 농축 한 후, 헥산과 클로로폼을 이용하여 컬럼 크로마토그래피로 분리하여 고체를 건조하여 [화학식 4-a]로 표시되는 화합물 24.62g을 얻었다. (수율 76.0%)20.0 g (0.061 mol) of 2-bromoflorenone and 19.57 ml (0.122 mol) of 3M phenylmagnesium bromide solution are added to a 500 ml round bottom flask. Stir for 3 hours, pour water to neutralize and cool, then extract with diethyl ether. The organics are treated with magnesium sulfate to remove moisture, concentrated under a reduced pressure filter and dried. The dried solid is dissolved in benzene, sulfuric acid is added and refluxed for 3 hours. After the reaction has cooled down, it is neutralized with sodium bicarbonate. Extract with chloroform, remove moisture with magnesium sulfate, concentrate under reduced pressure filter, separate by column chromatography using hexane and chloroform to dry the solid to give the compound 24.62g represented by [Formula 4-a] Got it. (Yield 76.0%)
(2) [화학식 52]로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by Formula 52
하기 [반응식 14]에 의하여 [화학식 52]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 52] was synthesized by the following [Scheme 14].
[반응식 14][Reaction Scheme 14]
[화학식 2-b] [화학식 4-a] [화학식 52] [Formula 2-b] [Formula 4-a] [Formula 52]
상기 합성예 2의 (3) [반응식 11]에서 사용된 아이오도벤젠 대신 [화학식 4-a]로 표시되는 화합물을 사용한 것을 제외하고는, 합성예 2의 (3)과 동일한 합성방법으로 합성하여 [화학식 52]로 표시되는 화합물 15.93g을 얻었다. (수율 86.5%)Synthesis by the same synthesis method as in (3) of Synthesis Example 2, except that the compound represented by [Formula 4-a] instead of the iodobenzene used in Synthesis Example 2 (3) [Scheme 11] 15.93 g of a compound represented by [Formula 52] was obtained. (Yield 86.5%)
MS(MALDI-TOF):m/z= 967.37 [M]+ MS (MALDI-TOF): m / z = 967.37 [M] +
EA(Elemental analysis) : 이론값 - C. 88.08 % ; H. 4.68 % ; N. 7.23 %Elemental analysis (EA): theoretical value-C. 88.08%; H. 4.68%; N. 7.23%
실제값 - C. 88.10 % ; H. 4.60 % ; N. 7.30 % Found-C. 88.10%; H. 4.60%; N. 7.30%
<합성예 5> [화학식 60]로 표시되는 화합물의 합성Synthesis Example 5 Synthesis of Compound Represented by
(1) [화학식 5-a]로 표시되는 화합물의 합성(1) Synthesis of Compound Represented by [Formula 5-a]
하기 [반응식 15]에 의하여 [화학식 5-a]로 표시되는 화합물을 합성하였다.The compound represented by [Formula 5-a] was synthesized by the following [Scheme 15].
[반응식 15][Reaction Scheme 15]
[화학식 5-a] [Formula 5-a]
500ml 둥근 바닥 플라스크에 N-페닐-1-나프틸아민 10.0g(0.046mol)과 1-브모로-3-아이오도벤젠 14.2g(0.05mol)과 Pd2(dba)3 0.8g(0.001mol)과 BINAP 0.6g(0.001 mol)을 넣고 톨루엔 700ml를 넣는다. 소듐 tert-부톡사이드 8.8g(0.091 mol)을 넣고 톨루엔 250ml를 넣고 12시간 환류한다. 반응물을 뜨거운 상태에서 감압필터하고 농축한 후, 헥산과 메틸렌 클로라이드를 전개 용매로 사용하여 컬럼 크로마토그래피로 분리하고 고체를 건조하여 [화학식 2-a]로 표시되는 화합물 12.60g을 얻었다. (수율 85.5%)10.0 g (0.046 mol) of N-phenyl-1-naphthylamine, 14.2 g (0.05 mol) of 1-bromo-3-iodobenzene and 0.8 g (0.001 mol) of Pd 2 (dba) 3 in a 500 ml round bottom flask Add 0.6 g (0.001 mol) of BINAP and 700 ml of toluene. Add 8.8 g (0.091 mol) of sodium tert-butoxide, add 250 ml of toluene, and reflux for 12 hours. The reaction product was filtered under reduced pressure in a hot state, concentrated, and separated by column chromatography using hexane and methylene chloride as a developing solvent, and dried to obtain 12.60 g of a compound represented by [Formula 2-a]. (Yield 85.5%)
(2) [화학식 60]으로 표시되는 화합물의 합성(2) Synthesis of Compound Represented by
하기 [반응식 16]에 의하여 [화학식 60]으로 표시되는 화합물을 합성하였다.The compound represented by [Formula 60] was synthesized by the following [Scheme 16].
[반응식 16][Reaction Scheme 16]
[화학식 2-b] [화학식 5-a] [화학식 60] [Formula 2-b] [Formula 5-a] [Formula 60]
상기 합성예 2의 (3) [반응식 11]에서 사용된 아이오도벤젠 대신 [화학식 5-a]로 표시되는 화합물을 사용한 것을 제외하고는, 합성예 2의 (3)과 동일한 합성 방법으로 합성하여 [화학식 60]으로 표시되는 화합물 20.03g을 얻었다. (수율 45.4%)Synthesis by the same synthesis method as in (3) of Synthesis Example 2, except that the compound represented by [Formula 5-a] instead of the iodobenzene used in Synthesis Example 2 (3) [Scheme 11] 20.03 g of a compound represented by [Formula 60] was obtained. (Yield 45.4%)
MS(MALDI-TOF):m/z= 944.36 [M]+ MS (MALDI-TOF): m / z = 944.36 [M] +
EA(Elemental analysis) : 이론값 - C. 86.42 % ; H. 4.69 % ; N. 8.89 %Elemental analysis (EA): theoretical value-C. 86.42%; H. 4.69%; N. 8.89%
실제값 - C. 86.26 % ; H. 4.65 % ; N. 9.09 % Found-C. 86.26%; H. 4.65%; N. 9.09%
<실시예 1 내지 5> 상기 합성예 1 내지 5에 의해서 합성된 화합물을 포함한 유기전계발광소자의 제조<Examples 1 to 5> Preparation of an organic electroluminescent device comprising a compound synthesized in Synthesis Examples 1 to 5
ITO 글래스의 발광 면적이 2mm×2mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1×10-6torr가 되도록 한 후 유기물을 상기 ITO위에 DNTPD(700Å), NPD(300Å), 본 발명에 의해 제조된 화합물 + Ir(ppy)3(10%)(300Å), Alq3(350Å), LiF(5Å), Al(1,000Å)의 순서로 성막하였으며, 0.4mA에서 측정을 하였다.The light emitting area of the ITO glass was patterned to have a size of 2 mm x 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 -6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), the compound + Ir (ppy) 3 (prepared by the present invention) 10%) (300 mW), Alq 3 (350 mW), LiF (5 mW), and Al (1,000 mW) were formed in this order and measured at 0.4 mA.
[DNTPD][DNTPD]
[NPD][NPD]
[Ir(ppy)3][Ir (ppy) 3 ]
[Alq3][Alq 3 ]
<비교예 1> Comparative Example 1
비교예를 위한 유기전계발광소자는 상기 실시예의 소자 구조에서 호스트 물질로서 본 발명에 의해 제조된 화합물 대신 CBP를 사용한 점을 제외하고 동일하게 제작하였다.An organic light emitting display device for a comparative example was manufactured in the same manner except for using CBP instead of the compound prepared by the present invention as a host material in the device structure of the above example.
[CBP][CBP]
상기 <실시예 1 내지 5>, <비교예 1> 및 [표 1]의 결과로부터, 본 발명에 따른 이형고리 화합물을 호스트 물질로 포함하는 유기전계발광소자는 호스트 물질이 CBP인 유기전계발광소자에 비하여 구동전압이 낮고, 전류효율이 우수한 특성을 보이므로, 표시소자, 디스플레이 소자 및 조명 등에 유용하게 사용될 수 있음을 알 수 있다.From the results of <Examples 1 to 5>, <Comparative Example 1> and [Table 1], the organic electroluminescent device comprising a heterocyclic compound according to the present invention as a host material is an organic electroluminescent device of which the host material is CBP In comparison with the low driving voltage and excellent current efficiency, it can be seen that it can be usefully used for display devices, display devices, and lighting.
Claims (9)
[화학식 1]
상기 식에서,
A1 및 A2 중 적어도 하나는 상기 [화학식 1]의 임의의 두 개의 탄소와 결합하여 축합환을 형성하는 것을 특징으로 하고,
R1 내지 R8은 각각 독립적으로 수소원자, 중수소원자, 할로겐원자, 치환 또는 비치환의 탄소수 6 내지 40의 아릴아미노기, 치환 또는 비치환의 탄소수 3 내지 40의 아릴옥시기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로아릴기, 게르마늄기, 인, 보론으로 이루어지는 군에서 선택되며,
L은 단결합 또는 2가의 연결기로서,
2가의 연결기인 경우 치환 또는 비치환의 탄소수 1 내지 10의 알킬렌기, 치환 또는 비치환의 탄소수 2 내지 10의 알케닐기, 치환 또는 비치환의 탄소수 2 내지 40의 알키닐기, 치환 또는 비치환의 탄소수 6 내지 40의 아릴기, 치환 또는 비치환의 탄소수 3 내지 40의 헤테로아릴기로 이루어지는 군에서 선택되고,
X는 O, S 및 SiR9R10으로 이루어지는 군에서 선택되며, R9 및 R10은 상기 R1 내지 R8의 정의와 동일하다.
n은 0 또는 1의 정수이다.A heterocyclic compound represented by the following [Formula 1]:
[Formula 1]
Where
At least one of A 1 and A 2 is characterized in that combined with any two carbon of [Formula 1] to form a condensed ring,
R 1 R 8 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted arylamino group having 6 to 40 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 40 carbon atoms, a substituted or unsubstituted C 6 to 40 carbon atom An aryl group, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron;
L is a single bond or a divalent linking group,
A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 40 carbon atoms, a substituted or unsubstituted carbon group having 6 to 40 carbon atoms An aryl group, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms,
X is selected from the group consisting of O, S and SiR 9 R 10 , R 9 And R 10 is the R 1 To R 8 .
n is an integer of 0 or 1.
상기 R1 내지 R10 및 L은 각각 독립적으로 수소원자, 중수소 원자, 시아노기, 할로겐 원자, 히드록시기, 니트로기, 탄소수 1 내지 40의 알킬기, 탄소수 1 내지 40의 알콕시기, 탄소수 1 내지 40의 알킬아미노기, 탄소수 6 내지 40의 아릴아미노기, 탄소수 3 내지 40의 헤테로아릴아미노기, 탄소수 1 내지 40의 알킬실릴기, 탄소수 6 내지 40의 아릴실릴기, 탄소수 6 내지 40의 아릴기, 탄소수 3 내지 40의 아릴옥시기, 탄소수 3 내지 40의 헤테로아릴기, 게르마늄기, 인 및 보론으로 이루어진 군으로부터 1종 이상 선택되어 치환되는 것을 특징으로 하는 이형고리 화합물.The method of claim 1,
The R 1 To R 10 And L are each independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, and a 6 to 40 carbon atoms Arylamino group, C3-40 heteroarylamino group, C1-40 alkylsilyl group, C6-40 arylsilyl group, C6-40 aryl group, C3-40 aryloxy group, C3 Heterocyclic group, characterized in that at least one selected from the group consisting of heteroaryl group, germanium group, phosphorus and boron of 40 to be substituted.
하기 [화학식 2] 내지 [화학식 88]로 표시되는 군으로부터 선택된 어느 하나의 화합물인 것을 특징으로 하는 이형고리 화합물:
[화학식 2] [화학식 3] [화학식 4]
[화학식 5] [화학식 6] [화학식 7]
[화학식 8] [화학식 9] [화학식 10]
[화학식 11] [화학식 12] [화학식 13]
[화학식 14] [화학식 15] [화학식 16]
[화학식 17] [화학식 18] [화학식 19]
[화학식 20] [화학식 21] [화학식 22]
[화학식 23] [화학식 24] [화학식 25]
[화학식 26] [화학식 27] [화학식 28]
[화학식 29] [화학식 30] [화학식 31]
[화학식 32] [화학식 33] [화학식 34]
[화학식 35] [화학식 36] [화학식 37]
[화학식 38] [화학식 39] [화학식 40]
[화학식 41] [화학식 42] [화학식 43]
[화학식 44] [화학식 45] [화학식 46]
[화학식 47] [화학식 48] [화학식 49]
[화학식 50] [화학식 51] [화학식 52]
[화학식 53] [화학식 54] [화학식 55]
[화학식 56] [화학식 57] [화학식 58]
[화학식 59] [화학식 60] [화학식 61]
[화학식 62] [화학식 63] [화학식 64]
[화학식 65] [화학식 66] [화학식 67]
[화학식 68] [화학식 69] [화학식 70]
[화학식 71] [화학식 72] [화학식 73]
[화학식 74] [화학식 75] [화학식 76]
[화학식 77] [화학식 78] [화학식 79]
[화학식 80] [화학식 81] [화학식 82]
[화학식 83] [화학식 84] [화학식 85]
[화학식 86] [화학식 87] [화학식 88]
A heterocyclic compound, characterized in that any one compound selected from the group represented by the following [Formula 2] to [Formula 88]:
[Formula 2] [Formula 3] [Formula 4]
[Formula 5] [Formula 6] [Formula 7]
[Formula 8] [Formula 9] [Formula 10]
[Formula 11] [Formula 12] [Formula 13]
[Formula 14] [Formula 15] [Formula 16]
[Formula 17] [Formula 18] [Formula 19]
[Formula 20] [Formula 21] [Formula 22]
[Formula 23] [Formula 24] [Formula 25]
[Formula 26] [Formula 27] [Formula 28]
[Formula 29] [Formula 30] [Formula 31]
[Formula 32] [Formula 33] [Formula 34]
[Formula 35] [Formula 36] [Formula 37]
[Formula 38] [Formula 39] [Formula 40]
[Formula 41] [Formula 42] [Formula 43]
[Formula 44] [Formula 45] [Formula 46]
[Formula 47] [Formula 48] [Formula 49]
[Formula 50] [Formula 51] [Formula 52]
[Formula 53] [Formula 54] [Formula 55]
[Formula 56] [Formula 57] [Formula 58]
[Formula 59] [Formula 60] [Formula 61]
[Formula 62] [Formula 63] [Formula 64]
[Formula 65] [Formula 66] [Formula 67]
[Formula 68] [Formula 69] [Formula 70]
[Formula 71] [Formula 72] [Formula 73]
[Formula 74] [Formula 75] [Formula 76]
[Formula 77] [Formula 78] [Formula 79]
[Formula 80] [Formula 81] [Formula 82]
[Formula 83] [Formula 84] [Formula 85]
[Formula 86] [Formula 87] [Formula 88]
캐소드;
및 상기 애노드 및 캐소드 사이에 개재되며, 제 1 항 내지 제 3 항의 이형고리 화합물을 포함하는 층을 구비한 유기전계발광소자. Anode;
Cathode;
And an layer interposed between the anode and the cathode, the layer including the heterocyclic compound of claim 1.
상기 이형고리 화합물은 상기 애노드 및 캐소드 사이의 발광층 중에 포함되는 것을 특징으로 하는 유기전계발광소자.The method of claim 4, wherein
The heterocyclic compound is an organic light emitting device, characterized in that contained in the light emitting layer between the anode and the cathode.
상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 5, wherein
An organic electroluminescent device further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the anode and the cathode.
상기 발광층의 두께는 50 내지 2,000 Å인 것을 특징으로 하는 유기전계발광소자. The method of claim 5, wherein
The thickness of the light emitting layer is an organic light emitting device, characterized in that 50 to 2,000 kPa.
상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성되는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
At least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecule deposition method or a solution process.
상기 유기전계발광소자는 표시소자, 디스플레이 소자, 또는 단색 또는 백색 조명용 소자에 사용되는 것을 특징으로 하는 유기전계발광소자.The method of claim 4, wherein
The organic electroluminescent device is an organic electroluminescent device, characterized in that used for a display device, a display device, or a device for monochrome or white illumination.
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