CN108864012A - One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device - Google Patents
One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device Download PDFInfo
- Publication number
- CN108864012A CN108864012A CN201811023317.1A CN201811023317A CN108864012A CN 108864012 A CN108864012 A CN 108864012A CN 201811023317 A CN201811023317 A CN 201811023317A CN 108864012 A CN108864012 A CN 108864012A
- Authority
- CN
- China
- Prior art keywords
- layer
- compound
- organic
- organic electroluminescence
- dibenzofurans
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 dibenzofurans compound Chemical class 0.000 title claims abstract description 51
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 32
- 239000010410 layer Substances 0.000 claims abstract description 103
- 239000012044 organic layer Substances 0.000 claims abstract description 23
- 230000005540 biological transmission Effects 0.000 claims abstract description 19
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 15
- 230000000903 blocking effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 19
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 2
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 238000002347 injection Methods 0.000 abstract description 9
- 239000007924 injection Substances 0.000 abstract description 9
- 230000008901 benefit Effects 0.000 abstract description 3
- 230000005284 excitation Effects 0.000 abstract description 2
- 239000010409 thin film Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 9
- 238000010586 diagram Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000011160 research Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001062009 Indigofera Species 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical class O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WGSKMKKKUXFRMB-UHFFFAOYSA-N CC1[Br-](=C)=C1Cc1ccc(C(c2c-3cccc2)(c2ccccc2)c2ccc4[o]c(ccc(Br)c5)c5c4c2)c-3c1 Chemical compound CC1[Br-](=C)=C1Cc1ccc(C(c2c-3cccc2)(c2ccccc2)c2ccc4[o]c(ccc(Br)c5)c5c4c2)c-3c1 WGSKMKKKUXFRMB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AWRLGNQRLPWTDY-UHFFFAOYSA-N Cc1c(cccc2)c2c(B(O)O)c2c1cccc2 Chemical compound Cc1c(cccc2)c2c(B(O)O)c2c1cccc2 AWRLGNQRLPWTDY-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 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
- IIRVBNFPODABQL-UHFFFAOYSA-N N,N-diphenylaniline ethene Chemical group C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1.C=C IIRVBNFPODABQL-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N O=C(c1ccccc1)Cl Chemical compound O=C(c1ccccc1)Cl PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical compound [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 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 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides one kind to be based on dibenzofurans compound, has the following structure formula：Should have preferable thermal stability, high-luminous-efficiency, high luminance purity based on dibenzofurans compound, and can be applied to organic electroluminescence device, solar battery, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer, in organic layer at least one layer containing if structural formula I is based on dibenzofurans compound, have the advantages that electroluminescent efficiency well using organic electroluminescence device make based on dibenzofurans compound and excitation purity be excellent and the service life is grown.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to one kind is based on dibenzofurans compound and its use
On the way, a kind of organic electroluminescence device is further related to.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one
The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode
Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust
Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology
High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent
Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as
As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it
General application, especially large screen display.And restricting one of key factor is exactly in organic electroluminescence device
The performance of electroluminescent organic material.Additionally, due to OLED device when applying voltage-operated, Joule heat can be generated, so that
Organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to develop the organic electroluminescence of stability and high efficiency
Luminescent material.
In three primary colors (red, indigo plant, green), feux rouges and green light material have been achieved for very big development recently, also comply with
The market demand of panel.For stablizing and efficient blue light material or seldom, due to the high energy gap of blue light, so that for material
Requirement it is higher, and stability due to blue phosphor materials and optical purity there are the problem of, develop the indigo plant of efficient stable
Color fluorescent material is particularly important.
Summary of the invention
The present invention provides one kind to be based on dibenzofurans compound, is the compound for having the following structure Formulas I：
Wherein, R1-R8Virtue independently selected from hydrogen, deuterium, halogen, the alkyl of C1-C12, substitution or unsubstituted C6-C30
Base；
Ar be selected from replace or the aryl of unsubstituted C6-C30, substitution or unsubstituted C3-C30 heteroaryl, take
The carbazyl of the triaromatic amine base of generation or unsubstituted C18-C30, substitution or unsubstituted C18-C30.
Optionally, R1-R8Selected from hydrogen, methyl, phenyl, tert-butyl, ethyl, propyl, isopropyl.
Optionally, Ar is selected from phenyl, deuterated benzene, diphenyl phenyl, naphthalene, naphthylphenyl, xenyl, three simultaneously phenyl, anthracene
Base, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base, (9,9- dialkyl group) fluorenyl, (substitution or unsubstituted of 9,9- bis-
Aryl) fluorenyl, substitution or unsubstituted dibenzothiophene and substitution or unsubstituted dibenzofuran group, triaromatic amine
Base and substitution or unsubstituted carbazyl.
Optionally, the compound for being following structural 1-28 based on dibenzofurans compound：
One kind of the invention is based on dibenzofurans compound can be prepared by Suzuki coupling reaction.
Of the invention can be applied to organic electroluminescence device based on dibenzofurans compound, solar battery, has
Machine thin film transistor (TFT) or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
Layer, in the organic layer it is at least one layer of containing as described in structural formula I based on dibenzofurans compound.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection
Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Optionally, the layer where the compound based on dibenzofurans is luminescent layer.
Being used alone based on dibenzofurans compound as described in structural formula I, or be used in mixed way with other compounds；Such as
One such compound can be used alone based on dibenzofurans compound described in structural formula I, can also use simultaneously
Two or more compound in structural formula I；Be used alone it is a kind of selected from structural formula 1-28 based on dibenzofurans
Compound, or simultaneously using two or more selected from structural formula 1-28 based on dibenzofurans compound.
The compound of structural formula I of the invention can be used as the single luminescent layer of non-impurity-doped or doping luminescent layer, wherein structure
Compound of formula I is as material of main part, and concentration is 20%-99.9%, the preferably 80%-99% of entire luminous layer weight, more
Preferably 90%-99%；When as guest materials, concentration is the 0.1%-50%, preferably 0.5%- of entire luminescent layer
10%.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer
Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance can effectively be transferred to hole on luminescent layer from anode.In addition to can be used with the compound of the present invention
It outside, can also include other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine
Close object, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano six
(hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'-
TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs
The range of visible light.Except it is of the invention there is Compounds of structural formula I in addition to, following compound can also be contained, but not limited to this,
Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, glimmering anthracene compound, anthracene class chemical combination
Object, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds,
Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.It can choose following compound, but
It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Object, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention
In, it is mainly selected from the alkali metal perhaps compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex can choose following compound, and but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With that can also be used with mixture, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental show the present invention as described in structural formula I based on dibenzofurans compound, there is preferable thermostabilization
Property, high-luminous-efficiency, high luminance purity.Had using the organic electroluminescence device based on the production of dibenzofurans compound
The advantage that electroluminescent efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention,
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as sending out
Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthetic method of intermediate 1-1
In there-necked flask, chlorobenzoyl chloride (30.8g, 0.22mol), dry methylene chloride (250mL) is added, in nitrogen protection
Under, alchlor (35g, 0.26mol) is added at 0 DEG C, then the bromo- dibenzofurans of 2- (49g, 0.2mol) is added portionwise, adds
Finish stirring 2 hours, add water quenching reaction, organic phase is crossed silica gel after washing liquid separation, is spin-dried for, crude product ethyl alcohol recrystallization obtains
Off-white powder 48g, yield 69%.
The synthetic method of intermediate 1-2
In flask, it is added intermediate 1-1 (35g, 100mmol), anhydrous tetrahydro furan (400mL), under nitrogen protection
It is cooled to 0 DEG C, is slowly added to 2- xenyl magnesium bromide grignard reagent (120mmol), is heated to reflux stirring 3 hours, it is cooling, then
It is slowly added to the dilute hydrochloric acid solution of 1N, pH value is improved to 7, is extracted with dichloromethane, dries, being concentrated, glacial acetic acid (200ml) is added
It with concentrated hydrochloric acid (10ml), is heated to reflux 5 hours, cooling removes solvent, Jia Shui, is extracted with dichloromethane, dries, being concentrated, thick to produce
Object obtains product 10g, yield 21% through column chromatographic purifying.
The synthetic method of compound 1
In flask, it is added intermediate 1-2 (2g, 4.1mmol), 9- phenyl -10- anthracene boric acid (1.22g, 4.1mmol), carbon
Sour potassium (1.4g, 10mmol), four triphenyl phosphorus (50mg), tetrahydrofuran (30mL), water (10mL) heat back under nitrogen protection
Stream 5 hours, it is cooling, tetrahydrofuran is removed, is extracted with dichloromethane, is dried, filtered with anhydrous sodium sulfate, is concentrated, product first
Benzene is recrystallized to give 2.1g, yield 79%.
The synthetic method of other embodiments such as compound 1, be all use intermediate 1-2 as raw material, then with other
Anthracene acid reaction, table 1 specific as follows：
Table 1
Embodiment 7
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment 1
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share
Department) successively pass through：Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, compound N PB is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the luminescent layer 140 of 40nm thickness is deposited on the hole transport layer, wherein luminescent material based on compound 3,
And using the BUBD-1 that weight ratio is 3% as doping guest materials.
Then, the Alq of 20nm thickness is deposited on the light-emitting layer3As electron transfer layer 150.
Finally, vapor deposition 1nm LiF is electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer
200mA/cm2Current density under current efficiency be 8.3cd/A.
Embodiment 8
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 2.It is made
Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity
Current efficiency under current density is 7.9cd/A.
Embodiment 9
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 3.It is made
Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity
Current efficiency under current density is 8.2cd/A.
Embodiment 10
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 8.
Prepared device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer
200mA/cm2Current density under current efficiency be 7.8cd/A.
Embodiment 11
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 11.It is made
Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity
Current efficiency under current density is 8.0cd/A.
Embodiment 12
The preparation method of device is as embodiment 7, other than replacing the compound 1 of embodiment 7 with compound 25.It is made
Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity
Current efficiency under current density is 7.5cd/A.
Comparative example
The preparation method of device is as embodiment 7, other than the compound 1 for replacing embodiment 7 with compound BH.It is made
Standby device (structural schematic diagram is as shown in Figure 1) is measured with Photo Research PR650 spectrometer in 200mA/cm2Electricity
Current efficiency under current density is 6.2cd/A.
By comparing, under identical brightness conditions, using the present invention is based on dibenzofurans compound prepare it is organic
The current efficiency of electroluminescent device is higher than comparative example, as described above, the compound of the present invention has high stability, preparation
Organic electroluminescence device has high efficiency and optical purity.
The structural formula of compound described in device is as follows：
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without
It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art
Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Technical solution, all should be within the scope of protection determined by the claims.
Claims (10)
1. one kind is based on dibenzofurans compound, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, R1-R8Aryl independently selected from hydrogen, deuterium, halogen, the alkyl of C1-C12, substitution or unsubstituted C6-C30；
Ar be selected from replace or the aryl of unsubstituted C6-C30, substitution or unsubstituted C3-C30 heteroaryl, replace or
The carbazyl of the triaromatic amine base of the unsubstituted C18-C30 of person, substitution or unsubstituted C18-C30.
2. being based on dibenzofurans compound as described in claim 1, which is characterized in that R1-R8Selected from hydrogen, methyl, phenyl,
Tert-butyl, ethyl, propyl, isopropyl.
3. being based on dibenzofurans compound as described in claim 1, which is characterized in that Ar is selected from phenyl, deuterated benzene, hexichol
Base phenyl, naphthalene, naphthylphenyl, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, acenaphthenyl, acenaphthylene base,
(9,9- dialkyl group) fluorenyl, (9,9- bis- replaces or unsubstituted aryl) fluorenyl, substitution or unsubstituted dibenzothiophenes
Base and substitution or unsubstituted dibenzofuran group, triaromatic amine base and substitution or unsubstituted carbazyl.
4. being based on dibenzofurans compound as described in claim 1, which is characterized in that be the chemical combination of following structural 1-28
Object：
5. the application described in claim 1 based on dibenzofurans compound in organic electroluminescence device.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole
Implanted layer, hole transmission layer, hole blocking layer, electron injecting layer, at least one layer in electron transfer layer, which is characterized in that institute
It states at least one layer of containing as described in claim 1 based on dibenzofurans compound in organic layer.
7. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to be based on dibenzo
Layer where furan compound is luminescent layer.
8. organic electroluminescence device as claimed in claim 7, which is characterized in that described to be made based on dibenzofurans compound
Based on material or guest materials, if weight is the 20%-99.9% of entire luminous layer weight when as material of main part；
If when as guest materials, weight is the 0.1%-50% of entire luminous layer weight.
9. organic electroluminescence device as claimed in claim 6, which is characterized in that described in claim 1 to be based on dibenzo
Furan compound is used alone, or is used in mixed way with other compounds.
10. organic electroluminescence device as claimed in claim 6, which is characterized in that be used alone a kind of selected from as right is wanted
Structural formula 1-28's described in asking 4 is selected from using two or more such as claim 4 institute based on dibenzofurans compound, or simultaneously
The structural formula 1-28 stated based on dibenzofurans compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811023317.1A CN108864012A (en) | 2018-09-03 | 2018-09-03 | One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811023317.1A CN108864012A (en) | 2018-09-03 | 2018-09-03 | One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108864012A true CN108864012A (en) | 2018-11-23 |
Family
ID=64322947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811023317.1A Pending CN108864012A (en) | 2018-09-03 | 2018-09-03 | One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108864012A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020127176A1 (en) * | 2018-12-20 | 2020-06-25 | Merck Patent Gmbh | Materials for electronic devices |
| JP2022036925A (en) * | 2020-08-24 | 2022-03-08 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| CN115996915A (en) * | 2020-06-26 | 2023-04-21 | Lt素材株式会社 | Heterocyclic compound and organic light-emitting device using same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101184822A (en) * | 2005-05-30 | 2008-05-21 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
| CN102850334A (en) * | 2012-08-28 | 2013-01-02 | 李崇 | Derivative compound treating dibenzofuran as core framework, and its application in OLED (organic light emission diode) |
| CN103797605A (en) * | 2011-09-09 | 2014-05-14 | 株式会社Lg化学 | Material for organic light emitting device and organic light emitting device using same |
| CN106478566A (en) * | 2016-09-27 | 2017-03-08 | 上海道亦化工科技有限公司 | Organic electroluminescent compounds and its organic electroluminescence device based on dibenzofurans |
-
2018
- 2018-09-03 CN CN201811023317.1A patent/CN108864012A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101184822A (en) * | 2005-05-30 | 2008-05-21 | 西巴特殊化学品控股有限公司 | Electroluminescent device |
| CN103797605A (en) * | 2011-09-09 | 2014-05-14 | 株式会社Lg化学 | Material for organic light emitting device and organic light emitting device using same |
| CN102850334A (en) * | 2012-08-28 | 2013-01-02 | 李崇 | Derivative compound treating dibenzofuran as core framework, and its application in OLED (organic light emission diode) |
| CN106478566A (en) * | 2016-09-27 | 2017-03-08 | 上海道亦化工科技有限公司 | Organic electroluminescent compounds and its organic electroluminescence device based on dibenzofurans |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020127176A1 (en) * | 2018-12-20 | 2020-06-25 | Merck Patent Gmbh | Materials for electronic devices |
| CN113195465A (en) * | 2018-12-20 | 2021-07-30 | 默克专利有限公司 | Material for electronic devices |
| JP2022515752A (en) * | 2018-12-20 | 2022-02-22 | メルク パテント ゲーエムベーハー | Materials for electronic devices |
| JP7543273B2 (en) | 2018-12-20 | 2024-09-02 | メルク パテント ゲーエムベーハー | Materials for Electronic Devices |
| JP2024174892A (en) * | 2018-12-20 | 2024-12-17 | メルク パテント ゲーエムベーハー | Materials for Electronic Devices |
| US12219874B2 (en) | 2018-12-20 | 2025-02-04 | Merck Patent Gmbh | Materials for electronic devices |
| CN115996915A (en) * | 2020-06-26 | 2023-04-21 | Lt素材株式会社 | Heterocyclic compound and organic light-emitting device using same |
| JP2022036925A (en) * | 2020-08-24 | 2022-03-08 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Organic electroluminescent compound and organic electroluminescent device comprising the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105481811B (en) | A kind of compound and its organic electroluminescence device with spiro structure | |
| CN109053698A (en) | A kind of aromatic amine compound and luminescent device containing dibenzofurans | |
| CN108864013A (en) | A kind of aromatic amine compound containing dibenzofurans and application thereof and luminescent device | |
| CN109336772A (en) | A kind of triaromatic amine compound containing spiro structure and application thereof and luminescent device | |
| CN108752221A (en) | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device | |
| CN108658953A (en) | A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device | |
| CN109265450A (en) | A kind of organic electroluminescent compounds and luminescent device of the aphthofurans containing benzo | |
| CN105601612B (en) | Phosphorescence host compound containing indolyl radical and its organic electroluminescence device | |
| CN109535175A (en) | A kind of double triaromatic amine compounds, application and the luminescent device of the spiro structure containing five-membered ring | |
| CN108997239A (en) | A kind of compound of cyano-containing and application thereof and organic electroluminescence device | |
| CN108299388A (en) | A kind of phenanthrene derivatives and application thereof and organic electroluminescence device | |
| CN109535093A (en) | A kind of trisubstituted benzene based compound and organic electroluminescence device | |
| CN108912099A (en) | A kind of compound containing triazine and carbazole and application thereof and organic electroluminescence device | |
| CN108047244A (en) | A kind of snail compound and application thereof and organic electroluminescence device | |
| CN107417677A (en) | A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device | |
| CN108299389A (en) | A kind of compound based on phenanthrene and carbazole and application thereof and organic electroluminescence device | |
| CN109320495A (en) | A kind of double triaromatic amine compounds, application and luminescent device containing spiro structure | |
| CN109705021A (en) | A kind of organic electroluminescent compounds of the alkylnaphthalene containing cycloheptyl and application thereof and luminescent device | |
| CN108752317A (en) | One kind is containing anthracene derivant and application thereof and luminescent device | |
| CN108864012A (en) | One kind is based on dibenzofurans compound and application thereof and organic electroluminescence device | |
| CN106831798B (en) | Compound and its organic electroluminescence device containing five-membered ring structure | |
| CN108358932A (en) | A kind of nitrogen heterocyclic and application thereof and organic electroluminescence device | |
| CN107652223A (en) | A kind of carbazoles organic electroluminescent compounds and its organic electroluminescence device | |
| CN108976196A (en) | A kind of aromatic amine compound of the spiro structure containing five-membered ring and application thereof and luminescent device | |
| CN108658789A (en) | A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20181123 |
|
| RJ01 | Rejection of invention patent application after publication |