CN108299389A - A kind of compound based on phenanthrene and carbazole and application thereof and organic electroluminescence device - Google Patents
A kind of compound based on phenanthrene and carbazole and application thereof and organic electroluminescence device Download PDFInfo
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- CN108299389A CN108299389A CN201711435598.7A CN201711435598A CN108299389A CN 108299389 A CN108299389 A CN 108299389A CN 201711435598 A CN201711435598 A CN 201711435598A CN 108299389 A CN108299389 A CN 108299389A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 32
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 26
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 title description 14
- 239000010410 layer Substances 0.000 claims abstract description 102
- -1 carbazole compound Chemical class 0.000 claims abstract description 41
- 239000012044 organic layer Substances 0.000 claims abstract description 25
- 230000005540 biological transmission Effects 0.000 claims abstract description 19
- 239000003205 fragrance Substances 0.000 claims abstract description 17
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 15
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-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
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 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
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003851 azoles Chemical class 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- GXGTZUUUEQORAH-UHFFFAOYSA-N C1=CC=CC=2SC3=C(C21)C=CC=C3.N3C=CC=CC=C3 Chemical compound C1=CC=CC=2SC3=C(C21)C=CC=C3.N3C=CC=CC=C3 GXGTZUUUEQORAH-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- OGNZZTLIIQCYCG-UHFFFAOYSA-N N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 Chemical group N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 OGNZZTLIIQCYCG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 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 description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical class ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 claims 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 13
- 239000007924 injection Substances 0.000 abstract description 13
- 230000000903 blocking effect Effects 0.000 abstract description 4
- 230000005284 excitation Effects 0.000 abstract description 2
- 239000010409 thin film Substances 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 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
- 239000004327 boric acid Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000151 deposition 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
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C1*2*)C=CC=C1C1NC2C=CC=C1 Chemical compound CC(C1*2*)C=CC=C1C1NC2C=CC=C1 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 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
- 238000010586 diagram Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 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
- 238000004528 spin coating Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
- DJMOXMNDXFFONV-UHFFFAOYSA-N 1,3-dimethyl-7-[2-(n-methylanilino)ethyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCN(C)C1=CC=CC=C1 DJMOXMNDXFFONV-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-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
- PKHGHKCIMCLEAN-UHFFFAOYSA-N Brc1c(-c(cc2)ccc2Nc(cccc2)c2-c2ccccc2)c(cccc2)c2c2c1C=CCC2 Chemical compound Brc1c(-c(cc2)ccc2Nc(cccc2)c2-c2ccccc2)c(cccc2)c2c2c1C=CCC2 PKHGHKCIMCLEAN-UHFFFAOYSA-N 0.000 description 1
- PZTXBZDMZJYHNO-VOLUUUQBSA-N C(C1)C=Cc(nc2-c3ccc(/C=C(\C=CC=C4)/C4=C(/C=CC=C4)\C4=C\C(C=C4)=CCC4[n]4c5ccccc5c5c4cccc5)cc3)c1[n]2-c1ccccc1 Chemical compound C(C1)C=Cc(nc2-c3ccc(/C=C(\C=CC=C4)/C4=C(/C=CC=C4)\C4=C\C(C=C4)=CCC4[n]4c5ccccc5c5c4cccc5)cc3)c1[n]2-c1ccccc1 PZTXBZDMZJYHNO-VOLUUUQBSA-N 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- DMGTYLBQPQPOFD-ZQHSETAFSA-N C=C/C(/c(cc1)ccc1-c1c(-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)c(cccc2)c2c2c1cccc2)=C\N=C Chemical compound C=C/C(/c(cc1)ccc1-c1c(-c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)c(cccc2)c2c2c1cccc2)=C\N=C DMGTYLBQPQPOFD-ZQHSETAFSA-N 0.000 description 1
- BBBOQLUVMQBVML-UHFFFAOYSA-N CB(c(cc1)ccc1-c1nc(cccc2)c2[n]1-c1ccccc1)O Chemical compound CB(c(cc1)ccc1-c1nc(cccc2)c2[n]1-c1ccccc1)O BBBOQLUVMQBVML-UHFFFAOYSA-N 0.000 description 1
- HSRMNKSBXWRTJO-UHFFFAOYSA-N COB(c1c(-c(cc2)ccc2-[n]2c(cccc3)c3c3ccccc23)c(cccc2)c2c2ccccc12)O Chemical compound COB(c1c(-c(cc2)ccc2-[n]2c(cccc3)c3c3ccccc23)c(cccc2)c2c2ccccc12)O HSRMNKSBXWRTJO-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 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
- 229940049706 benzodiazepine Drugs 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- WPQPMUCUCNOIKJ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ylbenzene Chemical compound C1C=CC=CC1C1=CC=CC=C1 WPQPMUCUCNOIKJ-UHFFFAOYSA-N 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
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 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
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical class OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 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
- 238000011160 research Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Abstract
The present invention provides a kind of based on luxuriant and rich with fragrance and carbazole compound, has the following structure formula：The compound has preferable thermal stability, high-luminous-efficiency and high luminance purity, can be applied to organic electroluminescence device, organic solar batteries, 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, electron transfer layer, the at least one layer compound containing such as structural formula I in organic layer, the organic electroluminescence device made of the compound have the advantages that electroluminescent efficiency is good and excitation purity is excellent and long lifespan.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of based on luxuriant and rich with fragrance and carbazole compound and its use
On the way, a kind of organic electroluminescence device is further related to.
Background technology
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 be adjusted as desired by the material for changing luminescent layer
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 with it is 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, since efficiency is low, it is wider that the factors such as service life is short restrict it
General application, especially large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED device
When, it will produce Joule heat 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 electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and promotion is arrived
100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), application also greatly carry
The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, is commonly used as phosphorus
The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work
Based on material when, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by
In the characteristic of the hole of CBP easily transmission and the flowing of electronics difficulty so that as a result the charge unbalance of luminescent layer reduces the effect of device
Rate.
Invention content
The present invention provides a kind of based on luxuriant and rich with fragrance and carbazole compound, to have the following structure the compound of Formulas I：
Wherein, Ar1Aryl selected from substitution or unsubstituted C6-C30；
Ar2Selected from the fragrant phosphino- for replacing the either heteroaryl of unsubstituted C3-C30, substitution or unsubstituted C3-C30；
R1-R8Independently selected from hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6-C30
Aryl.
Optionally, Ar1Selected from phenyl, cyano-phenyl, fluorine substituted-phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three
And phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (substitutions of 9,9- bis- or unsubstituted virtue
Base) fluorenyl, 9,9- be Spirofluorene-based, substitution either unsubstituted dibenzothiophene, substitution or unsubstituted dibenzofuran group.
Optionally, Ar2Selected from pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazoles
Base, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzofuran group, azepine dibenzothiophene, imidazoles
Base, the above aryl and heteroaryl can also be further that the alkyl of C1-C12 replaces.
Optionally, R1-R8Independently selected from hydrogen, phenyl, methyl.
Compound that is further alternative, being following structural 1-68 based on luxuriant and rich with fragrance and carbazole compound：
The a kind of of the present invention can be applied based on luxuriant and rich with fragrance and carbazole compound in organic electroluminescence device, organic solar
Battery, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Including at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
Layer；
Optionally, 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, at least one layer compound based on phenanthrene and carbazole contained as described in structural formula I in the organic layer；
Optionally, the layer where the compound based on phenanthrene and carbazole as described in structural formula I is luminescent layer, hole transport
Layer, hole injection layer.
It optionally, can be independent when the compound based on phenanthrene and carbazole as described in structural formula I is prepared for luminescent device
It uses, can also be used in mixed way with other compounds；Can individually it be made based on luxuriant and rich with fragrance and carbazole compound as described in structural formula I
With one such compound, the two or more compounds in structural formula I can also be used simultaneously.
The overall thickness of the organic electroluminescence device organic layer of the present 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 the organic electroluminescence device of the present 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 that can use with the compound of the present invention
Outside, it 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, six cyano, six miscellaneous triphen
(hexanitrilehexaazatriphenylene), tetra- cyanogen dimethyl-parabenzoquinone (F4- of tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'-
TCNQ), polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention has the good characteristics of luminescence, can be adjusted according to the needs
The range of visible light.In addition to the present invention is with Compounds of structural formula I, 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
In reaching effectively electronics from cathode transport to luminescent layer, there is prodigious electron mobility.Following compound can be selected, 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 by the electron injecting layer of organic electroluminescence device of the present invention from cathode
In, it is mainly selected from the alkali metal either compound of alkali metal or the compound selected from alkaline-earth metal or alkaline-earth metal or alkali
Metal complex can select following compound, and but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide either 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 can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present 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 shows compound based on phenanthrene and carbazole of the present invention as described in structural formula I, has preferable thermostabilization
Property, high-luminous-efficiency, high luminance purity.Have electroluminescent efficiency good using the organic electroluminescence device that the compound makes
The advantages of good and excitation purity is excellent and long lifespan.
Description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the present invention,
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be resistance
Barrier, 160 be luminescent layer, and 170 be electron transfer layer, and 180 be electron injecting layer, and 190 be cathode.
Specific implementation mode
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 flask, 9,10- of addition dibromos are luxuriant and rich with fragrance (16g, 48mmol), 9- phenyl -3- carbazoles boric acid (13.8g, 48mmol),
Potassium carbonate (13.6g, 100mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (200mL) and water (100mL) are protected in nitrogen
It is heated to reflux under shield 12 hours, it is cooling, it is extracted with dichloromethane, dry, concentration, crude product purifies to obtain product through column chromatography
12.5g, yield 52%.
The synthetic method of compound 1
In flask, addition intermediate 1 (1.5g, 3mmol), 3- pyridine boronic acids (0.8g, 4mmol), potassium carbonate (0.8g,
6mmol), tetra-triphenylphosphine palladium (50mg), tetrahydrofuran (20mL) and water (10mL), it is small to be heated to reflux 12 under nitrogen protection
When, it is cooling, it is extracted with dichloromethane, dry, concentration, crude product purifies to obtain product 1.1g, yield 74% through column chromatography.
Embodiment 2
The synthetic route of compound 8
The synthetic method of intermediate 8-1
In flask, intermediate 1-1 (8g, 16mmol) is added, anhydrous tetrahydro furan (100mL) is cooling under nitrogen protection
To -78 DEG C, it is slowly added to 2.5M normal-butyls hexane solution (19mmol, 7.8mL), reacts 1 hour, adds three isopropyl of boric acid
Ester (21mmol, 3.9g) is slowly increased to room temperature reaction 12 hours, and then plus dilute hydrochloric acid adjusts pH to less than 7, is extracted with dichloromethane
It takes, dry, concentration, crude product is stirred with n-hexane, is filtered, is dried to obtain product 5.9g, yield 79%.
The synthetic method of compound 8
Synthetic method as the synthesis of compound 1, it is raw materials used be intermediate 8-1 and 3,5- diphenyl -2- chlorotriazines,
Yield 64%.
Embodiment 3
The synthetic route of compound 16
For synthetic method as the synthetic method of compound 1, raw materials used is intermediate 8-1 and 4- (4- bromophenyls) -2,
6- diphenylpyrimidins, yield 72%.
Embodiment 4
The synthetic route of compound 25
For synthetic method as the synthetic method of compound 1, raw materials used is intermediate 8-1 and 2- (3- bromophenyls) -5,
5- diphenyl triazines, yield 75%.
Embodiment 5
The synthetic route of compound 27
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 1-1 and B- [4- (1- phenyl -1H- benzos
Imidazoles -2- bases) phenyl]-boric acid, yield 81%.
Embodiment 6
The synthetic route of compound 35
The synthetic method of intermediate 35-1
For synthetic method as the synthesis of intermediate 1-1, raw materials used is 9,10- dibromos phenanthrene and 4- (9- carbazyls) benzene
Base-boric acid, yield 56%.
The synthetic method of compound 35
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 35-1 and 3- pyridine pinacol ester, yield
77%.
Embodiment 7
The synthetic route of compound 44
The synthetic method of intermediate 44-1
For synthetic method as the synthesis of intermediate 8-1, raw materials used is intermediate 35-1, yield 68%.
The synthetic method of compound 44
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 44-1 and 4- (3- pyridyl groups)-bromobenzene,
Yield 75%.
Embodiment 8
The synthetic route of compound 59
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 44-1 and 2- (3- bromophenyls) -5,5- bis-
Phenyl triazine, yield 82%.
Embodiment 9
The synthetic route of compound 61
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 35-1 and B- [4- (1- phenyl -1H- benzene
And imidazoles -2- bases) phenyl]-boric acid, yield 85%.
Embodiment 10
The synthetic route of compound 64
For synthetic method as the synthesis of compound 1, raw materials used is intermediate 35-1 and 4- (2- phenyl -1H- benzo miaows
Azoles -1- bases) phenyl] boric acid, yield 69%.
Embodiment 11-20
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) it passes through successively：Deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, the MnO of 3nm thickness is deposited on ITO3(molybdenum oxide) is hole injection layer 130.
Then, the TAPC that 50nm thickness is deposited on hole injection layer is hole mobile material 140.
Then, TCTA is deposited, forms the electronic barrier layer 150 of 5nm thickness.
Then, the luminescent layer 160 of 20nm thickness is deposited on electronic barrier layer, wherein shine based on the compounds of this invention
Material, and the Ir (ppy) for being 3% with weight ratio3Guest materials is adulterated as phosphorescence.
Then, the BmPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 170.
Finally, vapor deposition 1nm LiF are electron injecting layer 180 and 80nm Al as device cathodes 190.
Prepared device (structural schematic diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
5000cd/m2Brightness under current efficiency be such as table 1.
Comparative example 1
Comparative example prepares the method for device as embodiment 11-20 device preparation methods, in addition to replacing the present invention with CBP
Compound as material of main part outside.
Table 1
| Embodiment | Compound | Current efficiency (cd/A) | Luminescent color |
| 11 | 1 | 52 | Green light |
| 12 | 8 | 53 | Green light |
| 13 | 16 | 56 | Green light |
| 14 | 25 | 57 | Green light |
| 15 | 27 | 55 | Green light |
| 16 | 35 | 56 | Green light |
| 17 | 44 | 54 | Green light |
| 18 | 59 | 54 | Green light |
| 19 | 61 | 57 | Green light |
| 20 | 64 | 56 | Green light |
| Comparative example 1 | CBP | 45 | Green light |
The structural formula of compound described in device is as follows：
From table 1 it follows that the compound of the present invention is used for organic electroluminescence device, operating voltage can be reduced,
Device efficiency is improved, is the phosphorescent light body material with excellent performance.As described above, the compound of the present invention has high stabilization
Property, the organic electroluminescence device of preparation has high efficiency and optical purity.
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 in the protection domain being defined in the patent claims.
Claims (10)
1. a kind of based on luxuriant and rich with fragrance and carbazole compound, which is characterized in that be the compound for having the following structure Formulas I：
Wherein, Ar1Aryl selected from substitution or unsubstituted C6-C30；
Ar2Selected from the fragrant phosphino- for replacing the either heteroaryl of unsubstituted C3-C30, substitution or unsubstituted C3-C30；
R1-R8Independently selected from the virtue of hydrogen, deuterium, the alkyl of C1-C12, the alkoxy of C1-C8, substitution or unsubstituted C6-C30
Base.
2. as described in claim 1 based on luxuriant and rich with fragrance and carbazole compound, which is characterized in that Ar1Selected from phenyl, cyano-phenyl, fluorine
Substituted-phenyl, xenyl, diphenyl substituted-phenyl, naphthalene, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9-
Dialkyl group) fluorenyl, (9,9- bis- replace or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or unsubstituted hexichol
Bithiophene base, substitution or unsubstituted dibenzofuran group.
3. as described in claim 1 based on luxuriant and rich with fragrance and carbazole compound, which is characterized in that Ar2Selected from pyridyl group, pyrimidine radicals, rattle away
Piperazine base, triazine radical, imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl,
Azepine dibenzofuran group, azepine dibenzothiophene, imidazole radicals, the above aryl and heteroaryl can also be further C1-C12
Alkyl substitution.
4. as described in claim 1 based on luxuriant and rich with fragrance and carbazole compound, which is characterized in that R1-R8Independently selected from hydrogen, phenyl,
Methyl.
5. as described in claim 1 based on luxuriant and rich with fragrance and carbazole compound, which is characterized in that be the chemical combination of following structural 1-68
Object：
6. the application described in claim 1 based on luxuriant and rich with fragrance and carbazole compound in organic electroluminescence device.
7. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole
At least one layer in implanted layer, hole transmission layer, exciton barrier-layer, electron transfer layer, which is characterized in that in the organic layer extremely
Few one layer containing as described in claim 1 based on luxuriant and rich with fragrance and carbazole compound.
8. organic electroluminescence device as claimed in claim 7, which is characterized in that as described in structural formula I based on luxuriant and rich with fragrance and click
Organic layer where the compound of azoles is luminescent layer.
9. organic electroluminescence device as claimed in claim 7, which is characterized in that as described in structural formula I based on luxuriant and rich with fragrance and click
One such compound is used alone in the compound of azoles, or uses two or more the change in structural formula I simultaneously
Close object.
10. organic electroluminescence device as claimed in claim 7, which is characterized in that the overall thickness of the organic layer is 1-
1000nm。
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| CN111205269A (en) * | 2020-01-10 | 2020-05-29 | 上海百豪新材料有限公司 | Preparation method and application preparation of carbazole-based organic electrophosphorescent material composition |
| CN113735833A (en) * | 2021-10-11 | 2021-12-03 | 西安瑞联新材料股份有限公司 | Compound with phenanthrocarbazole as core and application thereof |
| CN113811531A (en) * | 2019-04-25 | 2021-12-17 | 株式会社进雄产业 | Phenanthroline compound and organic light emitting device including same |
| CN114249685A (en) * | 2021-12-31 | 2022-03-29 | 华南理工大学 | Ortho-diaryl substituted phenanthrene or phenanthroline carrier transport material and preparation method and application thereof |
| TWI761014B (en) * | 2020-01-08 | 2022-04-11 | 大陸商上海傳勤新材料有限公司 | A kind of organic electronic material containing nitrogen atom heterocycle and its preparation method and application |
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| CN106033798A (en) * | 2015-03-09 | 2016-10-19 | 广东阿格蕾雅光电材料有限公司 | Organic electroluminescent device |
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| CN102918037A (en) * | 2010-06-02 | 2013-02-06 | 捷恩智株式会社 | Carbazole compound having substituent group including electron-accepting nitrogen-containing heteroaryl, and organic electroluminescent element |
| CN106033798A (en) * | 2015-03-09 | 2016-10-19 | 广东阿格蕾雅光电材料有限公司 | Organic electroluminescent device |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113811531A (en) * | 2019-04-25 | 2021-12-17 | 株式会社进雄产业 | Phenanthroline compound and organic light emitting device including same |
| TWI761014B (en) * | 2020-01-08 | 2022-04-11 | 大陸商上海傳勤新材料有限公司 | A kind of organic electronic material containing nitrogen atom heterocycle and its preparation method and application |
| CN111205269A (en) * | 2020-01-10 | 2020-05-29 | 上海百豪新材料有限公司 | Preparation method and application preparation of carbazole-based organic electrophosphorescent material composition |
| CN111205269B (en) * | 2020-01-10 | 2023-05-12 | 上海百豪新材料有限公司 | Carbazole-based organic electrophosphorescent material composition preparation method and application preparation |
| CN113735833A (en) * | 2021-10-11 | 2021-12-03 | 西安瑞联新材料股份有限公司 | Compound with phenanthrocarbazole as core and application thereof |
| CN114249685A (en) * | 2021-12-31 | 2022-03-29 | 华南理工大学 | Ortho-diaryl substituted phenanthrene or phenanthroline carrier transport material and preparation method and application thereof |
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