CN114394949A - Biphenylamine derivative and organic electroluminescent device thereof - Google Patents
Biphenylamine derivative and organic electroluminescent device thereof Download PDFInfo
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- CN114394949A CN114394949A CN202210090065.4A CN202210090065A CN114394949A CN 114394949 A CN114394949 A CN 114394949A CN 202210090065 A CN202210090065 A CN 202210090065A CN 114394949 A CN114394949 A CN 114394949A
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- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical class NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 title description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 23
- 239000010410 layer Substances 0.000 claims description 124
- -1 dibenzofuranyl group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 239000000126 substance Substances 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 239000012044 organic layer Substances 0.000 claims description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 8
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 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 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005593 norbornanyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical class C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 claims 6
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 77
- 239000000463 material Substances 0.000 abstract description 56
- 238000002347 injection Methods 0.000 abstract description 41
- 239000007924 injection Substances 0.000 abstract description 41
- 230000005525 hole transport Effects 0.000 abstract description 38
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 5
- 229930192474 thiophene Natural products 0.000 abstract description 4
- 238000005401 electroluminescence Methods 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 81
- 238000003786 synthesis reaction Methods 0.000 description 81
- 238000002360 preparation method Methods 0.000 description 65
- 125000004432 carbon atom Chemical group C* 0.000 description 52
- 238000001819 mass spectrum Methods 0.000 description 42
- 238000004128 high performance liquid chromatography Methods 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000001704 evaporation Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 11
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 3
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-N aluminum;2-methylquinolin-8-ol;4-phenylphenol Chemical compound [Al+3].C1=CC=C(O)C2=NC(C)=CC=C21.C1=CC=C(O)C2=NC(C)=CC=C21.C1=CC(O)=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 2
- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 2
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 2
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WPUSEOSICYGUEW-UHFFFAOYSA-N 4-[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WPUSEOSICYGUEW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GWNJZSGBZMLRBW-UHFFFAOYSA-N 9,10-dinaphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 GWNJZSGBZMLRBW-UHFFFAOYSA-N 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- DBNYWRKRZTXMCU-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 DBNYWRKRZTXMCU-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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Abstract
The invention provides a biphenyl derivative and an organic electroluminescent device thereof, belonging to the technical field of organic electroluminescence. The benzidine derivative provided by the invention introduces five-membered alicyclic ring and furan/thiophene on the basis of benzidine, so that the molecule movement of the benzidine derivative is reduced in space, and the molecular crystallization trend is effectively inhibited, thus the compound has good film forming property and thermal stability, and meanwhile, the benzidine derivative has higher HOMO energy level and good hole mobility, and when the benzidine derivative is used as a hole transport layer/light-emitting auxiliary layer material, the hole injection and transport balance in a device can be improved, the light-emitting efficiency of the device is greatly improved, and the service life of the device is greatly prolonged. The benzidine derivative and the organic electroluminescent device thereof have good application effect and industrialization prospect.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a benzidine derivative and an organic electroluminescent device thereof.
Background
Organic Light-emitting Devices (OLEDs) refer to Devices in which holes injected from an anode and electrons injected from a cathode are transported and recombined in an Organic layer to form excitons, which in turn emit Light. Alq of sandwich structure was published for the first time by Tang et al3Since the electroluminescence of green devices, OLEDs are highly focused and widely researched by their advantages of being light, thin, foldable, flexible to display, surface-emitting, and low in power consumption.
OLEDs generally have a structure of an anode, a cathode, and an organic layer, and the organic layer is generally formed as a multi-layer structure composed of various materials, for example, a hole transport region, an electron transport region, a light emitting layer, a capping layer, and the like, in order to improve efficiency and lifespan of an organic electroluminescent device. The light-emitting mechanism is as follows: under the drive of an external voltage, electrons enter the electron transmission area layer from the cathode, holes enter the hole transmission area layer from the anode, the electrons and the holes are combined in the light emitting layer to generate excitons, and the excitons are radiatively transited back to the ground state and emit light. The lighting process can be summarized as the following four steps: (1) injecting carriers; (2) the transmission of carriers in the organic layer; (3) the positive and negative carriers are combined to form excitons; (4) the exciton radiates transition luminescence.
The hole transport region, which has a main function of injecting and transporting holes, may be classified into a hole injection layer, a hole transport layer, a light emission auxiliary layer, an electron blocking layer, and the like. The hole transport material has the main effects of improving the injection and transmission balance of holes in the device, the hole transport material with excellent performance can reduce the energy barrier in the hole injection process, the hole injection efficiency is improved, meanwhile, the hole transport rate in the device can be improved through good hole mobility, the hole transport rate and the electron transport rate are balanced, and holes and electrons are effectively compounded in the light-emitting layer to form excitons. Therefore, the development of a class of hole transport materials with excellent performance is crucial to the development of OLEDs.
Disclosure of Invention
In order to improve the hole injection efficiency and the transmission efficiency in the device and balance the hole transmission rate and the electron transmission rate in the device, the invention provides a biphenyl derivative and an organic electroluminescent device thereof. The benzidine derivative provided by the invention has good hole mobility and thermal stability, and can be used as a hole transport material to be applied to an organic electroluminescent device, so that the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
The invention provides a benzidine derivative, which has the following structure,
wherein, Ar is1Selected from the group consisting of the structures represented by chemical formula 2,
the ring A is selected from any one of the structures shown below,
ar is2～Ar4At least one of them is selected from the group consisting of the structure shown in chemical formula 3, and the others are the same or different and are selected from the group consisting of chemical formula 2, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C25 alicyclic ring and C2-C30 heteroaromatic groupFused ring group of ring, -any one of N (Ra) (Rb);
the Ra and the Rb are the same or different and are selected from any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C3-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic ring, fused ring group of C6-C30 aromatic ring and substituted or unsubstituted C2-C30 heteroaryl;
x is selected from O or S;
the R is1、R2、R3Any one of the same or different selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C3-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic ring, C6-C30 aromatic ring fused ring group, and substituted or unsubstituted C2-C30 heteroaryl;
n is1Selected from 0,1, 2,3 or 4; when n is1Greater than 1, two or more R1Are the same or different from each other, or adjacent R1May form a substituted or unsubstituted ring;
n is2Selected from 0,1, 2,3, 4,5, 6 or 7; when n is2Greater than 1, two or more R2Are the same or different from each other;
n is4Selected from 0,1, 2,3, 4,5, 6 or 7; when n is4Greater than 1, two or more R3Are the same or different from each other, or adjacent R3May form a substituted or unsubstituted ring;
said L1～L4The same or different are selected from single bond, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C3-C30 alicyclic group and CAny one of a fused cyclic group of an aromatic ring of 6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C30;
n is3Selected from 1,2, 3 or 4; when n3 is greater than 1, two or more
The same or different from each other.
The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer between and outside the anode and the cathode, wherein the organic layer comprises a hole transport region, a light-emitting layer and an electron transport region, and the hole transport region contains one or more of the benzidine derivatives.
The invention has the beneficial effects that:
the benzidine derivative provided by the invention changes the molecular structure by introducing five-membered alicyclic ring and furan/thiophene modification into benzidine, forms a compound with large steric hindrance, increases the number of molecular conformational isomers, reduces the movement of molecules in space, further reduces the aggregation force between molecules, and effectively inhibits the molecular crystallization trend, thereby improving the film forming property and the thermal stability of the compound; meanwhile, benzidine + five-membered alicyclic ring + furan/thiophene enables electrophilic N atoms in the structure to attract electrons on aromatic rings through an induction effect, meanwhile, due to P-pi conjugation effect, unshared electrons on the N atom are supplied to the aromatic ring to enrich the electrons, the conjugation effect is larger than the induction effect, on the other hand, the special conjugation system of the derivative expands the electron delocalization range, so that the mobility of electrons in molecules is enhanced, the HOMO energy level of the benzidine derivative is effectively improved, the electron energy is reduced, the hole mobility of the material is greatly improved, when the benzidine derivative is used as a hole transport material to be evaporated into a device, the injection and the transport of holes in the device can be improved, the hole transmission rate and the electron transmission rate of the device are balanced, and holes and electrons are effectively compounded in the light-emitting layer to form excitons, so that the light-emitting efficiency of the device is greatly improved.
Detailed Description
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
In the context of the present specification,
means a moiety attached to another substituent.
In the present specification, "-" means a moiety linked to another substituent.
In the present specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example,
can represent
And so on.
The alkyl group in the present invention refers to a monovalent group formed by dropping one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group, a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 6 carbon atoms, and examples may include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a hexyl group, and the like, but are not limited thereto.
The alicyclic group in the present invention means a monovalent group formed by removing one hydrogen atom from an alicyclic hydrocarbon molecule, and may be a cycloalkyl group, a cycloalkenyl group, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 7 carbon atoms, and examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc.
The cycloalkyl group in the present invention means a monovalent group formed by subtracting one hydrogen atom from a cycloalkane molecule, and preferably has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and preferably 3 to 7 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like, but are not limited thereto.
The cycloalkenyl group in the present invention means a monovalent group formed by dropping one hydrogen atom from a cycloolefin molecule, and preferably has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and preferably 3 to 7 carbon atoms, and examples may include cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and the like, but are not limited thereto.
The heterocycloalkyl group in the invention is a univalent group formed by subtracting one hydrogen atom from a heterocycloalkyl molecule, and the heteroatom can be one or more of N, O, S, Si and P. Preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 7 carbon atoms, and examples may include azetidinyl, tetrahydropyrrolyl, piperidinyl and the like, but are not limited thereto.
The aryl group in the present invention refers to a monovalent group obtained by removing one hydrogen atom from an aromatic core carbon of an aromatic hydrocarbon molecule, and may be a monocyclic aryl group, a polycyclic aryl group or a condensed ring aryl group, and preferably has 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, and examples may include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a triphenylene group, a perylene group, and the like, but are not limited thereto.
The fused cyclic group of the alicyclic ring and the aromatic ring in the invention refers to a general name of a monovalent group left by removing one hydrogen atom after the alicyclic ring and the aromatic ring are fused together. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, most preferably 7 to 12 carbon atoms, and examples may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.
The heteroaryl group in the present invention is a general term for a monovalent group obtained by removing a hydrogen atom from a nuclear atom of an aromatic heterocyclic ring composed of carbon and a hetero atom. The hetero atom may be one or more of N, O, S, Si, P, may be a monocyclic heteroaryl group or a fused heteroaryl group, preferably having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 3 to 12 carbon atoms, most preferably 3 to 8 carbon atoms, and examples may include pyrrolyl, pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, indolyl, quinolyl, isoquinolyl, oxazolyl, thiazolyl, imidazolyl, benzothienyl, benzofuryl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridooxazolyl, pyridothiazolyl, pyridoimidazolyl, pyrimidoxazolyl, pyrimidozolyl, pyrimido thiazolyl, pyrimido imidazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, phenazinyl, quinoxalinyl, quinazolinyl, quinoxalyl, Quinolinothiazolyl, quinolinoimidazolyl, purinyl, 2-purinyl, N-imidazolyl, and the like, but is not limited thereto.
The fused cyclic group of the alicyclic ring and the heteroaromatic ring in the invention is a general term for removing one hydrogen atom after the alicyclic ring and the heteroaromatic ring are fused together to leave a monovalent group. Preferably having 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, most preferably 5 to 12 carbon atoms, and examples may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidocycloheptyl, dibenzofurocyclopropyl, dibenzofurocyclobutyl, dibenzofurocyclopentyl, dibenzofurocyclohexyl, dibenzofurocycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, dibenzothienocycloheptyl, carbazolocyclopropyl, carbazolocyclobutyl, carbazolocyclopentyl, carbazolocyclohexyl, carbazolocycloheptyl, and the like, but are not limited thereto.
The arylene group in the present invention refers to a general term of divalent groups remaining after two hydrogen atoms are removed from an aromatic nucleus of an aromatic hydrocarbon molecule, and may be monocyclic arylene group, polycyclic arylene group or condensed ring arylene group, preferably having 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms, and examples may include phenylene, biphenylene, terphenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, triphenylene, peryleneene, and the like, but are not limited thereto.
The heteroarylene group according to the present invention means a general term in which two hydrogen atoms are removed from the core carbon of an aromatic heterocyclic ring composed of carbon and hetero atoms, which may be one or more of N, O, S, Si, P, a monocyclic heteroarylene group or a condensed-ring heteroarylene group, preferably having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 3 to 12 carbon atoms, most preferably 3 to 8 carbon atoms, and examples may include a pyrrolylene group, a pyridylene group, a pyrimidylene group, a triazinylene group, a thienylene group, a furylene group, an indolyl group, a quinolylene group, an isoquinolylene group, an oxazolylene group, a thiazolyl group, a furylene group, a benzothiophenylene group, a benzofuranylene group, a benzoxazylene group, a benzothiazylene group, a benzimidazolylene group, a pyridazolylene group, a, Pyridinylimidazolylides, pyrimidinyleneoxazolyls, pyrimidinylenethiazolyls, pyrimidinyleneimidazolyls, dibenzofuranylenes, dibenzothiophenylenes, carbazolylenes, phenazinyls, quinoxalylenes, quinazolinylenes, quinolinyleneoxazolyls, quinolinylenethiazolyls, quinolinyleneimidazolyls, purinylenes, and the like, but are not limited thereto.
The alicyclic group in the present invention means a divalent group in which two hydrogen atoms are omitted from an alicyclic hydrocarbon molecule, and may be a cycloalkylene group, a cycloalkenylene group, or the like, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 7 carbon atoms, and examples may include, but are not limited to, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, an adamantylene group, a norbornylene group, a cyclopropenylene group, a cyclobutenyl group, a cyclopentenylene group, a cyclohexenylene group, a cycloheptenylene group, or the like.
The term "fused ring group" of an alicyclic ring and an aromatic ring as used herein refers to a general term in which an alicyclic ring and an aromatic ring are fused together and then two hydrogen atoms are removed to leave a divalent group. Preferably having 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, most preferably 7 to 12 carbon atoms, and examples may include benzocyclobutene, benzocyclopentylene, benzocyclohexylene, benzocycloheptyl, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.
The "substitution" as referred to herein means that a hydrogen atom in a compound group is replaced with another atom or group, and the position of substitution is not limited.
The "substituted or unsubstituted" as referred to herein means not substituted or substituted with one or more substituents selected from the group consisting of: deuterium, a halogen atom, an amino group, a cyano group, a nitro group, an alkyl group of C1 to C25, a cycloalkyl group of C3 to C25, an aryl group of C6 to C30, a heteroaryl group of C2 to C30, an arylamine group of C6 to C30, an aryloxy group of C6 to C30, preferably deuterium, a halogen atom, a cyano group, an alkyl group of C1 to C12, an aryl group of C6 to C25, a heteroaryl group of C2 to C25, and specific examples thereof may include deuterium, fluorine, chlorine, bromine, iodine, a cyano group, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, benzocyclobutenyl, benzocyclopentyl, benzocyclocyclohexyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclobutenyl, phenyltritolyl, tolyl, mesityl, biphenylyl, naphthyl, anthryl, phenanthrenyl, triphenylenyl, phenanthrenyl, pyrenyl, and the like,
A phenyl group, a perylene group, a fluoranthenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a carbazolyl group, a 9-phenylcarbazolyl group, a spirobifluorenyl group, a carbazoloindolyl group, a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, an oxazolyl group, a thiazolyl group, an imidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzotriazolyl group, a benzimidazolyl group, a pyridooxazolyl group, a pyridothiazolyl group, a pyridoimidazolyl group, a pyrimido oxazolyl group, a pyrimido imidazolyl group, a quinolyl group, an isoquinolyl group, a quinolonooxazolyl group, a quinolothiazolyl group, a phenothiazinyl group, a phenoxazinyl group, Acridinyl, and the like, but are not limited thereto. Or when the substituents are two or more, adjacent substituents may be bonded to form a ring; when the substituents are two or more, the substituents may be the same as or different from each other.
The linking to form a substituted or unsubstituted ring according to the present invention means that the two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:
in the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a fused ring, and examples may include benzene, pyridine, pyrimidine, naphthalene, cyclopentene, cyclopentane, cyclohexane, cyclohexano, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but are not limited thereto.
The invention provides a benzidine derivative, which has the following structure,
wherein, Ar is1Selected from the group consisting of the structures represented by chemical formula 2,
the ring A is selected from any one of the structures shown below,
ar is2～Ar4At least one of them is selected from the group consisting of the structure of chemical formula 3, and the others are the same or different and selected from any one of chemical formula 2, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C25 alicyclic ring and C2-C30 fused ring group, — N Ra and (Rb);
the Ra and the Rb are the same or different and are selected from any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C3-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic ring, fused ring group of C6-C30 aromatic ring and substituted or unsubstituted C2-C30 heteroaryl;
x is selected from O or S;
the R is1、R2、R3The same or different hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C3-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbonAny one of a group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring, and a substituted or unsubstituted C2-C30 heteroaryl;
n is1Selected from 0,1, 2,3 or 4; when n is1Greater than 1, two or more R1Are the same or different from each other, or adjacent R1May form a substituted or unsubstituted ring;
n is2Selected from 0,1, 2,3, 4,5, 6 or 7; when n is2Greater than 1, two or more R2Are the same or different from each other;
n is4Selected from 0,1, 2,3, 4,5, 6 or 7; when n is4Greater than 1, two or more R3Are the same or different from each other, or adjacent R3May form a substituted or unsubstituted ring;
said L1～L4Any one of the same or different single bonds, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C3-C30 alicyclic group, substituted or unsubstituted C6-C30 aromatic ring fused cyclic group and substituted or unsubstituted C2-C30 heteroarylene group;
n is3Selected from 1,2, 3 or 4; when n3 is greater than 1, two or more
The same or different from each other.
Preferably, the benzidine derivative is selected from any one of chemical formula 1-1 to chemical formula 1-8,
the R is1The same or different is selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted t-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted methyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted isopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted isopropyl, and substituted or unsubstituted tert-butyl,Any one of substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
n is1Selected from 0,1, 2,3 or 4; when n is1Greater than 1, two or more R1Are the same or different from each other, or adjacent R1May form a substituted or unsubstituted ring therebetween.
Preferably, Ar is2～Ar4At least one selected from the group consisting of the structures represented by chemical formula 3, means Ar2Selected from the structures shown in chemical formula 3, or Ar3Selected from the structures shown in chemical formula 3, or Ar4Selected from the structures shown in chemical formula 3, or Ar2And Ar3Selected from the structures shown in chemical formula 3, or Ar2And Ar4Selected from the structures shown in chemical formula 3, or Ar3And Ar4Selected from the structures shown in chemical formula 3, or Ar2、Ar3And Ar4Selected from the structures shown in chemical formula 3.
Preferably, the chemical formula 3 is selected from any one of the structures shown below,
X0any one selected from O, S, C (Rc) (Rd) and N (Re);
the R is3Rc, Rd are the same or different and are selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropylAny one of a group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentenyl group, a substituted or unsubstituted cyclohexenyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted piperidinyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted carbazolyl group;
the Re is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, Any one of substituted or unsubstituted carbazolyl groups.
Preferably, the chemical formula 3 is selected from any one of the structures shown below,
preferably, the chemical formula 2 is selected from any one of the structures shown below,
preferably, Ar is2～Ar4At least one of them is selected from the group consisting of the structures represented by chemical formula 3, and the remaining same or different are selected from any one of chemical formula 2, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentenyl group, a substituted or unsubstituted cyclohexenyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted piperidyl group, or the structures represented below,
said Y is1、Y2The same or different is selected from O, S, C (Rf) (Rg) and N (Rh);
the R is4、R5、R6、R7Rf and Rg are the same or different and are selected from the group consisting of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted t-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornanyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, and substituted or unsubstituted methylOr any one of unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl and substituted or unsubstituted carbazolyl;
the Rh is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, Any one of substituted or unsubstituted carbazolyl groups;
m is1Selected from 0,1, 2,3, 4 or 5; m is2Selected from 0,1, 2,3 or 4; m is3Selected from 0,1, 2,3, 4,5, 6 or 7; m is4Selected from 0,1, 2,3, 4,5, 6,7, 8 or 9; m is5Selected from 0,1, 2,3, 4,5, 6,7 or 8; when m is1、m2、m3、m4、m5Greater than 1, two or more R4Are the same or different from each other, two or more R5Are the same or different from each other, or adjacent R4May form a substituted or unsubstituted ring, adjacent R5May form a substituted or unsubstituted ring;
said L0Is selected from any one of single bond, substituted or unsubstituted arylene of C6-C18 and substituted or unsubstituted heteroarylene of C2-C18.
Preferably, Ar is2～Ar4At least one of them is selected from the structures shown in chemical formula 3, and the others are the same or different and are selected from the structures shown in chemical formula 2Substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, or any of the structures shown below,
preferably, said L1～L3The same or different is selected from a single bond or any one of the structures shown below,
wherein, R is8、R9Any one of the same or different hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C2-C12 heteroaryl;
k is1Identical or different from 0,1, 2,3 or 4, k2Identical or different from 0,1, 2,3, 4,5 or 6, k3The same or different is selected from 0 and 12,3, 4,5, 6,7 or 8, k4The same or different is selected from 0,1, 2 or 3; when k is1、k2、k3、k4Greater than 1, two or more R9R being identical or different from each other, or adjacent to each other9May form a substituted or unsubstituted ring therebetween.
Preferably, said L1～L3The same or different is selected from a single bond or any one of the structures shown below,
the R is8The same or different ones are selected from any one of hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, tolyl, pentadeuterated phenyl, naphthyl and deuterated naphthyl.
Preferably, the benzidine derivative has any one of the structures shown below,
the invention also provides a preparation method of the biphenyl derivative,
xa, which may be identical or different, are selected from I, Br, Cl;
Ar1-Ar4、L1-L4、R1、n1、n3the definitions are the same as above;
the reaction type of the benzidine derivative is Buchwald reaction.
The present invention may be bonded to the above-mentioned substituents through a method known in the art, and the kind and position of the substituents or the number of the substituents may be changed according to the technique known in the art.
The invention provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer between and outside the anode and the cathode, wherein the organic layer comprises a hole transport region, a luminescent layer and an electron transport region, and the hole transport region contains one or more than one of the benzidine derivatives.
The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light emission auxiliary layer.
Preferably, the hole transport region includes a hole injection layer containing one or more of the benzidine derivatives of the present invention.
Preferably, the hole transport region comprises a hole transport layer containing one or more of the benzidine derivatives of the present invention.
Preferably, the hole transport region includes a light emission auxiliary layer containing one or more of the benzidine derivatives of the present invention.
The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.
The organic layer of the present invention may further include a capping layer, an encapsulation layer, and the like. However, the structure of the organic electroluminescent device of the present invention is not limited to the above structure, and if necessary, the organic layers may be omitted or simultaneously have a plurality of organic layers, and the organic layers having the same function may be formed in a stacked structure of two or more layers.
The light-emitting layer of the present invention may include a host material, a dopant material, and the like, and may be formed of a single-layer structure or a multilayer structure in which layers above each other are stacked.
The organic electroluminescent device of the present invention preferably has the following structure:
substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode;
substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
substrate/anode/hole injection layer/hole transport layer/electron blocking layer/luminescent layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
substrate/anode/hole injection layer/hole transport layer/electron blocking layer/luminescent layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;
substrate/anode/hole injection layer/hole transport layer/light-emitting auxiliary layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
substrate/anode/hole injection layer/hole transport layer/light-emitting auxiliary layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;
however, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the parameter requirements of the device and the characteristics of materials, part of organic layers can be added or omitted, and the organic layers with the same function can be made into a laminated structure with more than two layers.
The organic electroluminescent device of the present invention is generally formed on a substrate. The substrate may be any substrate as long as it does not change when forming an electrode or an organic layer, for example, a substrate of glass, plastic, a polymer film, silicon, or the like.
In the organic electroluminescent device according to the present invention, it is preferable to use a high work function material capable of promoting hole injection into the organic layer as the anode material. Specific examples of the anode material usable in the present invention may include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO); combinations of metals and oxides, such as ITO-Ag-ITO; and conductive polymers such as poly (3-methylthiophene), polypyrrole, polyaniline, poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDT), and the like, but not limited thereto. Preferably, the anode material is selected from ITO, ITO-Ag-ITO and the like.
In the organic electroluminescent device according to the present invention, the hole injection material is preferably a material having a good hole accepting ability. Specific examples of the hole injection material that can be used in the present invention may include: metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, phthalocyanine compound, benzidine compound, phenazine compound, and the like, for example, copper phthalocyanine (CuPc), titanyl phthalocyanine, N, N ' -diphenyl-N, N ' -di- [4- (N, N-diphenylamine) phenyl ] benzidine (NPNPNPNPB), N, N, N ', N ' -tetrakis (4-methoxyphenyl) benzidine (MeO-TPD), bisquinoxalino [2,3-a:2',3' -c ] phenazine (HATNA), 4' -tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN), 4,4' -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like, but is not limited thereto. Preferably, the hole injection material of the present invention is selected from copper phthalocyanine (CuPc), 4',4 ″ -tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 4',4 ″ -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like.
In the organic electroluminescent device of the present invention, the hole transport material is preferably a material having an excellent hole transport property and a HOMO level matched with a corresponding anode material. Specific examples of the hole transporting material usable in the present invention may include diphenylamines, triphenylamines, fluorenes and carbazoles, such as N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -di (naphthalen-1-yl) -N, N ' -di (phenyl) -2,2' -dimethylbenzidine (. alpha. -NPD), N ' -diphenyl-N, N ' -di (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), 4- [1- [4- [ di (4-methylphenyl) amino ] phenyl ] cyclohexyl ] -N- (3-methylphenyl) -N- (4-methylphenyl) aniline (TAPC), the benzidine derivative according to the present invention, and the like, but is not limited thereto. Preferably, the hole transport material of the present invention is selected from one or more of the benzidine derivatives of the present invention.
In the organic electroluminescent device, the light-emitting auxiliary layer is preferably made of a material with good hole transport performance and electron blocking performance. Specific examples of the light-emitting auxiliary material usable in the present invention may include triarylamine derivatives, spirofluorene derivatives, furan derivatives, and the like, such as TPD, NPB, N4, N4-bis ([1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1,1':4', 1' -terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4' -diamine, N- ([1,1' -diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9' -spirobifluorene-2-amine, N-bis ([1,1' -biphenyl ] -4-yl) -3' - (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, benzidine derivatives described in the present invention, and the like, but are not limited thereto. Preferably, the material of the luminescence auxiliary layer according to the present invention is selected from one or more of the benzidine derivatives according to the present invention.
In the organic electroluminescent device of the present invention, the light-emitting layer material includes a light-emitting layer host material and a light-emitting layer dopant material, and the light-emitting layer host material may be selected from 4,4 '-bis (9-Carbazole) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -ADN), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4',1": 4', 1' -quaterphenyl.]-4,4' -diamino (4PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), and the like, but is not limited thereto. Preferably, the host material of the light emitting layer of the present invention is selected from 9, 10-bis (2-naphthyl) Anthracene (ADN), 9'- (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 ″ -tris (carbazole-9)-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), AND the like. The luminescent layer doping material can be selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyrene-1-amine) (DPAP-DPPA), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 4' -bis [4- (diphenylamino) styryl]Biphenyl (BDAVBi), 4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), bis (2-hydroxyphenylpyridine) beryllium (Bepp2), bis (4, 6-difluorophenylpyridine-C2, N) picolinyliridium (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy)3) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)2(acac)), 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq)3) Bis (1-phenylisoquinoline) (acetylacetonato) iridium (Ir (piq))2(acac)), etc., but is not limited thereto. Preferably, the light emitting layer guest of the present invention is selected from 4,4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 9, 10-di [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like.
The doping ratio of the host material for the light-emitting layer and the dopant material for the light-emitting layer is preferably different depending on the materials used, and is usually 0.01% to 20%, preferably 0.1% to 15%, more preferably 1% to 10%.
In the organic electroluminescent device according to the present invention, the hole blocking material has a strong hole blocking ability and suitable HOMO and LUMO levels, and specific examples of the hole blocking material that can be used in the present invention may include imidazoles, triazoles, phenanthroline derivatives, and the like, such as 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), and the like, but are not limited thereto. Preferably, the hole blocking material according to the present invention is selected from 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), and the like.
In the organic electroluminescent device according to the present invention, the electron transport material is preferably a material having a strong electron withdrawing ability and low HOMO and LUMO levels, and specific examples of the electron transport material that can be used in the present invention may include imidazoles, triazoles, phenanthroline derivatives, quinolines, and the like, such as 2,9- (dimethyl) -4, 7-biphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris [ (3-pyridyl) -phenyl ] phenanthrene]Benzene (TmPyPB), 4' -bis (4, 6-diphenyl-1, 3, 5-triazinyl) biphenyl (BTB), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 2- (naphthalen-2-yl) -4,7- (diphenyl) -1, 10-phenanthroline (HNBphen), 8-hydroxyquinoline-Lithium (LiQ), and the like, but are not limited thereto. Preferably, the electron transport material of the present invention is selected from 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq)3) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BALq) and the like, but are not limited thereto.
In the organic electroluminescent device according to the present invention, the electron injection material is preferably a material having a small difference in potential barrier with an adjacent organic transport material or host material, and has an effect of injecting electrons from the cathode. Examples of the electron injecting material that can be used in the present invention include: alkali metal salts (such as LiF, CsF), alkaline earth metal salts (such as MgF)2) Metal oxides (e.g. Al)2O3、MoO3) But is not limited thereto. Preferably, the electron injection material of the present invention is selected from lithium fluoride (LiF), 8-hydroxyquinoline-lithium (Liq), and the like.
In the organic electroluminescent device according to the present invention, a low work function material capable of promoting electron injection into the organic layer is preferably used as the cathode material. Specific examples of the cathode material that can be used in the present invention may include: metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metallic materials, e.g. LiF/Al, Mg/Ag, Li/Al, LiO2/Al、BaF2Al, etc., but are not limited thereto. Preferably, the cathode according to the invention is selected from semi-transparent cathodes, such as Ag or Mg-Ag alloys or thin Al.
In the organic electroluminescent device according to the present invention, a material for improving optical coupling is preferably used as the material for the cover layer. Specific examples of the cover layer material that may be used in the present invention may include arylamine derivatives, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, and the like, but are not limited thereto. The coating layer may be formed on both the outer side of the anode and the outer side of the cathode, or may be disposed on the outer side of the anode or the outer side of the cathode, and preferably, the coating layer according to the present invention is disposed on the outer side of the cathode.
The present invention is not particularly limited to the thickness of each organic layer of the organic electroluminescent device, and may be any thickness commonly used in the art.
The organic electroluminescent device of the present invention may employ any one of vacuum evaporation, spin coating, vapor deposition, knife coating, laser thermal transfer, electrospray coating, slit coating, and dip coating, and in the present invention, vacuum evaporation is preferably employed.
The organic electroluminescent device can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lamps and the like.
The invention is explained in more detail by the following examples, without wishing to restrict the invention accordingly. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue inventive effort.
Preparation and characterization of the Compounds
Description of raw materials, reagents and characterization equipment:
the present invention is not particularly limited to the starting materials and sources of reagents used in the following examples, and they may be commercially available products or prepared by methods known to those skilled in the art.
The mass spectrum uses British Watts G2-Si quadrupole rod series time-of-flight high resolution mass spectrometer, chloroform is used as solvent;
the element analysis uses a Vario EL cube type organic element analyzer of Germany Elementar company, and the mass of a sample is 5-10 mg;
synthesis example 1: preparation of Compound 2
Preparation of intermediate c-2:
toluene (600mL), a-2(13.32g, 100.00mmol), b-2(24.71g, 100.00mmol), palladium acetate (0.34g, 1.5mmol), sodium tert-butoxide (19.22g, 200.00mmol) and tri-tert-butylphosphine (16mL of a 1.0M solution in toluene) were added to a reaction flask, dissolved by stirring, and the reaction was refluxed for 2 hours under nitrogen. After the temperature of the system is reduced to room temperature, the reaction solution is filtered by diatomite, filtrate is concentrated, recrystallization is carried out by methanol, the reaction solution is filtered, and filter cakes are collected to obtain c-2(23.35g, the yield is 78%), and the mass spectrum m/z is as follows: 299.1321 (theoretical value: 299.1310).
Preparation of intermediate f-2:
toluene (600mL), d-2(16.92g, 100.00mmol), e-2(23.31g, 100.00mmol), palladium acetate (0.34g, 1.5mmol), sodium tert-butoxide (19.22g, 200.00mmol) and tri-tert-butylphosphine (16mL of a 1.0M solution in toluene) were added to a reaction flask, dissolved by stirring, and the reaction was refluxed for 2 hours under nitrogen. After the temperature of the system was decreased to room temperature, the reaction solution was filtered through celite, the filtrate was concentrated, and recrystallized with toluene/methanol 4/1, the reaction solution was suction-filtered, the filter cake was washed with methanol, and the filter cake was collected to obtain f-2(27.32g, yield 85%), ms m/z: 321.1529 (theoretical value: 321.1517).
Preparation of intermediate h-2:
toluene (400mL), g-2(11.49g, 60.00mmol), c-2(17.96g, 60.00mmol), 1' -bis (diphenylphosphino) ferrocene palladium dichloride (0.66g, 0.90mmol) and potassium tert-butoxide (13.47g, 120mmol) were added to a reaction flask, dissolved with stirring and reacted under reflux for 3 hours under nitrogen. After the temperature of the system was reduced to room temperature, the reaction solution was filtered through celite, the filtrate was concentrated, and recrystallized with toluene/methanol 10/1, the reaction solution was suction-filtered, the filter cake was washed with methanol, and the filter cake was collected to obtain h-2(17.95g, yield 73%), mass m/z: 409.1221 (theoretical value: 409.1233).
Preparation of compound 2:
toluene (200mL), h-2(12.30g, 30.00mmol), f-2(10.61g, 33.00mmol), tris (dibenzylideneacetone) dipalladium (0.41g, 0.45mmol), potassium tert-butoxide (6.73g, 60.00mmol) and BINAP (1.87g, 3.00mmol) were added to a reaction flask, dissolved by stirring, and reacted under reflux for 5 hours under nitrogen. And (3) after the temperature of the system is reduced to room temperature, filtering the system by using kieselguhr, concentrating filtrate, recrystallizing the filtrate by using ethyl acetate, performing suction filtration, and leaching the filtrate by using methanol to obtain recrystallized solid, so that the compound 2(15.84g, the yield is 76%) is obtained, and the purity of the solid is not less than 99.89% by HPLC (high performance liquid chromatography). Mass spectrum m/z: 694.2971 (theoretical value: 694.2984). Theoretical element content (%) C51H38N2O: c, 88.15; h, 5.51; and N, 4.03. Measured elemental content (%): c, 88.21; h, 5.47; and N, 3.98.
Synthesis example 2: preparation of Compound 6
Compound 6(14.23g) was obtained by the same preparation method as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-6 and e-2 was replaced with equimolar e-6; the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 658.3002 (theoretical value: 658.2984). Theoretical element content (%) C48H38N2O: c, 87.51; h, 5.81; and N, 4.25. Measured elemental content (%): c, 87.46; h, 5.78; and N, 4.30.
Synthetic example 3: preparation of Compound 25
Compound 25(17.12g) was obtained by the same preparation method as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-25, b-2 was replaced with equimolar b-25, and d-2 was replaced with equimolar a-25; the HPLC purity is more than or equal to 99.81 percent.Mass spectrum m/z: 826.3397 (theoretical value: 826.3382). Theoretical element content (%) C60H46N2S: c, 87.13; h, 5.61; and N, 3.39. Measured elemental content (%): c, 87.08; h, 5.57; n, 3.44.
Synthetic example 4: preparation of Compound 44
Compound 44(17.12g) was obtained by the same preparation method as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-44, e-2 was replaced with equimolar e-44, and g-2 was replaced with equimolar g-44; the HPLC purity is more than or equal to 99.86 percent. Mass spectrum m/z: 781.3082 (theoretical value: 781.3093). Theoretical element content (%) C57H39N3O: c, 87.55; h, 5.03; n, 5.37. Measured elemental content (%): c, 87.61; h, 4.97; n, 5.41.
Synthesis example 5: preparation of Compound 49
Compound 49(17.79g) was obtained in the same manner as in Synthesis example 1 except that g-2 in Synthesis example 1 was replaced with equimolar g-49; the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 846.3626 (theoretical value: 846.3610). Theoretical element content (%) C63H46N2O: c, 89.33; h, 5.47; and N, 3.31. Measured elemental content (%): c, 89.28; h, 5.50; and N, 3.28.
Synthetic example 6: preparation of Compound 56
Synthesis example 1 was repeated except that a-2 was replaced with equimolar a-6, b-2 was replaced with equimolar b-56, d-2 was replaced with equimolar d-56, e-2 was replaced with equimolar b-56, and g-2 was replaced with equimolar g-49According to the same production method as in Synthesis example 1, Compound 56(20.81g) was obtained; the HPLC purity is more than or equal to 99.78 percent. Mass spectrum m/z: 962.5191 (theoretical value: 962.5175). Theoretical element content (%) C71H66N2O: c, 88.53; h, 6.91; and N, 2.91. Measured elemental content (%): c, 88.49; h, 6.88; and N, 2.95.
Synthetic example 7: preparation of Compound 60
Preparation of intermediate c-60:
the same preparation method as that for intermediate c-2 in synthetic example 1 was followed except for replacing b-2 in synthetic example 1 with equimolar b-60 to give intermediate c-60(23.97g), mass m/z: 315.1096 (theoretical value: 315.1082).
Preparation of compound 60:
toluene (400mL), g-60(11.64g, 30.00mmol), c-60(20.82, 66.00mmol), tris (dibenzylideneacetone) dipalladium (0.82g, 0.90mmol), potassium tert-butoxide (13.47, 120.00mmol) and BINAP (3.74g, 6.00mmol) were added to a reaction flask, dissolved by stirring, and reacted under reflux for 5 hours under nitrogen. After the temperature of the system is reduced to room temperature, filtering with diatomite, concentrating the filtrate, recrystallizing with ethyl acetate, filtering, and leaching with methanol to obtain a recrystallized solid, thus obtaining a compound 60(20.06g, yield 78%); the HPLC purity is more than or equal to 99.79 percent. Mass spectrum m/z: 856.2957 (theoretical value: 856.2946). Theoretical element content (%) C60H44N2S2: c, 84.08; h, 5.17; and N, 3.27. Measured elemental content (%): c, 84.12; h, 5.20; and N, 3.23.
Synthesis example 8: preparation of Compound 71
Synthesis example 1 in which a-2 was replaced with equimolar a-44, b-2 was replaced with equimolar b-71, d-2 was replaced with equimolar d-71, and e-2 was replaced withSubstitution of equimolar e-71, g-2 for equimolar g-49 was carried out in the same manner as in Synthesis example 1 to give Compound 71(16.83 g); the HPLC purity is more than or equal to 99.81 percent. Mass spectrum m/z: 824.3211 (theoretical value: 824.3225). Theoretical element content (%) C60H44N2S: c, 87.34; h, 5.38; and N, 3.40. Measured elemental content (%): c, 87.29; h, 5.43; and N, 3.39.
Synthetic example 9: preparation of Compound 100
Compound 100(16.98g) was obtained by the same preparation method as in Synthesis example 1 except that b-2 was replaced with equimolar e-2 and g-2 was replaced with equimolar g-100 in Synthesis example 1; the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 734.3285 (theoretical value: 734.3297). Theoretical element content (%) C54H42N2O: c, 88.25; h, 5.76; and N, 3.81. Measured elemental content (%): c, 88.30; h, 5.75; n, 3.79.
Synthetic example 10: preparation of Compound 102
Compound 102(14.67g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-44, b-2 was replaced with equimolar b-102, d-2 was replaced with equimolar a-44, e-2 was replaced with equimolar b-60, and g-2 was replaced with equimolar g-102; the HPLC purity is more than or equal to 99.81 percent. Mass spectrum m/z: 708.2612 (theoretical value: 708.2599). Theoretical element content (%) C51H36N2S: c, 86.41; h, 5.12; and N, 3.95. Measured elemental content (%): c, 86.37; h, 5.09; and N, 4.01.
Synthetic example 11: preparation of Compound 108
Compound 108(17.69g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-44, b-2 was replaced with equimolar e-2, e-2 was replaced with equimolar e-108, and g-2 was replaced with equimolar g-108; the HPLC purity is more than or equal to 99.78 percent. Mass spectrum m/z: 920.3776 (theoretical value: 920.3767). Theoretical element content (%) C69H48N2O: c, 89.97; h, 5.25; and N, 3.04. Measured elemental content (%): c, 90.01; h, 5.27; and N, 2.99.
Synthetic example 12: preparation of Compound 126
Preparation of intermediate c-126:
the same preparation method as that for intermediate c-2 in synthetic example 1 was followed except that a-2 in synthetic example 1 was replaced with equimolar a-44, b-2 was replaced with equimolar b-60, and g-2 was replaced with equimolar g-126, to give intermediate c-126(24.13g), mass m/z: 313.0938 (theoretical value: 313.0925).
Preparation of compound 126:
compound 126(18.68g) was obtained by the same preparation method as in Synthesis example 7 except that g-60 in Synthesis example 7 was replaced with equimolar g-126; the HPLC purity is more than or equal to 99.75 percent. Mass spectrum m/z: 928.2933 (theoretical value: 928.2946). Theoretical element content (%) C66H44N2S2: c, 85.31; h, 4.77; and N, 3.01. Measured elemental content (%): c, 85.26; h, 4.81; and N, 2.98.
Synthetic example 13: preparation of Compound 136
Compound 136(17.81g) was obtained by the same preparation method as in Synthesis example 1 except that e-2 in Synthesis example 1 was replaced with equimolar b-2; HPLCThe purity is more than or equal to 99.87 percent. Mass spectrum m/z: 770.3309 (theoretical value: 770.3297). Theoretical element content (%) C57H42N2O: c, 88.80; h, 5.49; and N, 3.63. Measured elemental content (%): c, 88.75; h, 5.53; and N, 3.66.
Synthesis example 14: preparation of Compound 137
Compound 137(17.81g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-6, b-2 was replaced with equimolar b-137, d-2 was replaced with equimolar d-137, e-2 was replaced with equimolar b-137, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 780.3941 (theoretical value: 780.3925). Theoretical element content (%) C57H32D10N2O: c, 87.66; h, 6.71; and N, 3.59. Measured elemental content (%): c, 87.71; h, 67; and N, 3.62.
Synthetic example 15: preparation of Compound 140
Compound 140(20.39g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-6, b-2 was replaced with equimolar b-140, d-2 was replaced with equimolar d-56, e-2 was replaced with equimolar b-140, and g-2 was replaced with equimolar g-140; the HPLC purity is more than or equal to 99.77 percent. Mass spectrum m/z: 930.4412 (theoretical value: 930.4425). Theoretical element content (%) C69H42D8N2O: c, 89.00; h, 6.28; and N, 3.01. Measured elemental content (%): c, 88.97; h, 6.31; and N, 2.98.
Synthetic example 16: preparation of Compound 142
Compound 142(17.65g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-142, b-2 was replaced with equimolar b-142, d-2 was replaced with equimolar d-142, e-2 was replaced with equimolar b-142, and g-2 was replaced with equimolar g-100; HPLC purity is more than or equal to 99.84%. Mass spectrum m/z: 794.3314 (theoretical value: 794.3297). Theoretical element content (%) C59H42N2O: c, 89.14; h, 5.33; and N, 3.52. Measured elemental content (%): c, 89.09; h, 5.37; n, 3.54.
Synthetic example 17: preparation of Compound 146
Compound 146(16.76g) was obtained in the same manner as in Synthesis example 1 except that b-2 in Synthesis example 1 was replaced with equimolar b-146 and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.87 percent. Mass spectrum m/z: 734.3282 (theoretical value: 734.3297). Theoretical element content (%) C54H42N2O: c, 88.25; h, 5.76; and N, 3.81. Measured elemental content (%): c, 88.31; h, 5.74; n, 3.79.
Synthetic example 18: preparation of Compound 156
Compound 156(19.41g) was obtained in the same manner as in Synthesis example 1 except that b-2 in Synthesis example 1 was replaced with equimolar b-71, d-2 was replaced with equimolar d-56, e-2 was replaced with equimolar b-71, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.83 percent. Mass spectrum m/z: 850.3941 (theoretical value: 850.3923). Theoretical element content (%) C63H50N2O: c, 88.91; h, 5.92; and N, 3.29. Measured elemental content (%): c, 88.86; h, 5.90; n, 3.34.
Synthetic example 19: preparation of Compound 180
Compound 180(20.31g) was obtained in the same manner as in Synthesis example 1 except that b-2 in Synthesis example 1 was replaced with equimolar b-180, d-2 was replaced with equimolar d-56, e-2 was replaced with equimolar b-180, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.79 percent. Mass spectrum m/z: 952.4127 (theoretical value: 952.4141). Theoretical element content (%) C69H52N4O: c, 86.94; h, 5.50; and N, 5.88. Measured elemental content (%): c, 86.98; h, 5.46; and N, 5.91.
Synthesis example 20: preparation of compound 186
Compound 186(17.35g) was obtained by the same preparation method as in Synthesis example 1 except that g-2 in Synthesis example 1 was replaced with equimolar g-102; the HPLC purity is more than or equal to 99.86 percent. Mass spectrum m/z: 770.3281 (theoretical value: 770.3297). Theoretical element content (%) C57H42N2O: c, 88.80; h, 5.49; and N, 3.63. Measured elemental content (%): c, 88.76; h, 5.51; n, 3.67.
Synthetic example 21: preparation of Compound 187
Compound 187(19.42g) was obtained by the same preparation method as in Synthesis example 1 except that d-2 in Synthesis example 1 was replaced with equimolar d-187 and e-2 was replaced with equimolar b-2; the HPLC purity is more than or equal to 99.76 percent. Mass spectrum m/z: 898.3932 (theoretical value: 898.3923). Theoretical element content (%) C67H50N2O: c, 89.50; h, 5.61; and N, 3.12. Measured elemental content (%): c, 89.47; h, 5.65; and N, 3.09.
Synthetic example 22: preparation of Compound 192
Compound 192(15.52g) was obtained according to the same preparation method as in synthesis example 1 except that intermediate h-2 in synthesis example 1 was replaced with an equimolar amount of intermediate h-146 and intermediate f-2 was replaced with an equimolar amount of intermediate c-2; the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 698.3285 (theoretical value: 698.3297). Theoretical element content (%) C51H42N2O: c, 87.65; h, 6.06; and N, 4.01. Measured elemental content (%): c, 87.63; h, 6.11; and N, 3.96.
Synthetic example 23: preparation of Compound 202
Compound 202(21.14g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-142, b-2 was replaced with equimolar b-202, d-2 was replaced with equimolar a-142, e-2 was replaced with equimolar b-2, and g-2 was replaced with equimolar g-100; HPLC purity is more than or equal to 99.74 percent. Mass spectrum m/z: 926.4249 (theoretical value: 926.4236). Theoretical element content (%) C69H54N2O: c, 89.38; h, 5.87; and N, 3.02. Measured elemental content (%): c, 89.42; h, 5.91; and N, 2.97.
Synthetic example 24: preparation of Compound 230
Compound 230 (19) was obtained in the same manner as in Synthesis example 1, except that a-2 in Synthesis example 1 was replaced with equimolar a-230, b-2 was replaced with equimolar b-230, d-2 was replaced with equimolar d-230, e-2 was replaced with equimolar b-2, and g-2 was replaced with equimolar g-10091 g); the HPLC purity is more than or equal to 99.76 percent. Mass spectrum m/z: 908.3412 (theoretical value: 908.3403). Theoretical element content (%) C67H44N2O2: c, 88.52; h, 4.88; and N, 3.08. Measured elemental content (%): c, 88.49; h, 4.92; n, 3.11.
Synthetic example 25: preparation of Compound 231
Compound 231(18.43g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-230, b-2 was replaced with equimolar e-2, e-2 was replaced with equimolar e-231, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 818.3288 (theoretical value: 818.3297). Theoretical element content (%) C61H42N2O: c, 89.46; h, 5.17; and N, 3.42. Measured elemental content (%): c, 89.43; h, 5.22; and N, 3.39.
Synthetic example 26: preparation of Compound 257
Compound 257(16.79g) was obtained according to the same preparation method as that of Synthesis example 1, except that a-2 in Synthesis example 1 was replaced with equimolar a-6, b-2 was replaced with equimolar b-257, d-2 was replaced with equimolar d-257, e-2 was replaced with equimolar b-257, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.83 percent. Mass spectrum m/z: 822.4019 (theoretical value: 822.4008). Theoretical element content (%) C59H54N2S: c, 86.09; h, 6.61; and N, 3.40. Measured elemental content (%): c, 86.11; h, 6.59; n, 3.43.
Synthetic example 27: preparation of compound 279
Compound 279(20.74g) was obtained by the same preparation method as in Synthesis example 1 except that b-2 in Synthesis example 1 was replaced with equimolar b-279, d-2 was replaced with equimolar d-279, e-2 was replaced with equimolar b-279, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.75 percent. Mass spectrum m/z: 986.5585 (theoretical value: 986.5573). Theoretical element content (%) C71H74N2S: c, 86.36; h, 7.55; n, 2.84. Measured elemental content (%): c, 86.41; h, 7.56; n, 2.81.
Synthetic example 28: preparation of Compound 285
Compound 285(22.67g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-6, b-2 was replaced with equimolar b-285, d-2 was replaced with equimolar d-285, e-2 was replaced with equimolar b-285, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.71 percent. Mass spectrum m/z: 1110.3996 (theoretical value: 1110.4008). Theoretical element content (%) C83H54N2S: c, 89.70; h, 4.90; and N, 2.52. Measured elemental content (%): c, 89.67; h, 4.86; and N, 2.55.
Synthetic example 29: preparation of Compound 336
Compound 336(19.4g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-230, b-2 was replaced with equimolar b-336, d-2 was replaced with equimolar d-279, e-2 was replaced with equimolar b-336, and g-2 was replaced with equimolar g-336; the HPLC purity is more than or equal to 99.76 percent. Mass spectrum m/z: 964.3842 (theoretical value: 964.3851). Theoretical element content (%) C71H52N2S: c, 88.35; h, 5.43; and N, 2.90. Measured elemental content (%): c, 88.38; h, 5.39; and N,2.88。
Synthetic example 30: preparation of compound 376
Compound 376(16.49g) was obtained by the same preparation method as in Synthesis example 1 except that d-2 was replaced with equimolar d-279 and g-2 was replaced with equimolar g-102; the HPLC purity is more than or equal to 99.85 percent. Mass spectrum m/z: 784.2924 (theoretical value: 784.2912). Theoretical element content (%) C57H40N2S: c, 87.21; h, 5.14; and N, 3.57. Measured elemental content (%): c, 87.17; h, 5.16; and N, 3.61.
Synthetic example 31: preparation of Compound 391
Compound 391(16.65g) was obtained in the same manner as in Synthesis example 1 except that g-2 in Synthesis example 1 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.86 percent. Mass spectrum m/z: 770.3284 (theoretical value: 770.3297). Theoretical element content (%) C57H42N2O: c, 88.80; h, 5.49; and N, 3.63. Measured elemental content (%): c, 88.75; h, 5.52; and N, 3.61.
Synthetic example 32: preparation of Compound 435
Compound 435(17.36g) was obtained in the same manner as in Synthesis example 1 except that d-2 in Synthesis example 1 was replaced with equimolar d-56, e-2 was replaced with equimolar b-2, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.82 percent. Mass spectrum m/z: 814.2665 (theoretical value: 814.2654). Theoretical element content (%) C57H38N2O2S: c, 84.00; h, 4.70; n, 3.44. Measured elemental content(％)：C,83.98；H,4.67；N,3.47。
Synthetic example 33: preparation of compound 441
Compound 441(19.16g) was obtained in the same manner as in Synthesis example 1 except that b-2 was replaced with equimolar b-441 and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.81 percent. Mass spectrum m/z: 862.3398 (theoretical value: 862.3382). Theoretical element content (%) C63H46N2S: c, 87.67; h, 5.37; and N, 3.25. Measured elemental content (%): c, 87.71; h, 5.40; and N, 3.22.
Synthesis example 34: preparation of Compound 505
Compound 505(15.96g) was obtained in the same manner as in Synthesis example 1 except that b-2 in Synthesis example 1 was replaced with equimolar e-108, d-2 was replaced with equimolar d-71, e-2 was replaced with equimolar b-137, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z: 699.3288 (theoretical value: 699.3298). Theoretical element content (%) C51H33D5N2O: c, 87.52; h, 6.19; and N, 4.00. Measured elemental content (%): c, 87.49; h, 6.24; and N, 3.96.
Synthetic example 35: preparation of Compound 510
Compound 510(18.23g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-6, b-2 was replaced with equimolar b-510, d-2 was replaced with equimolar d-510, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.85 percent.Mass spectrum m/z: 820.3443 (theoretical value: 820.3454). Theoretical element content (%) C61H44N2O: c, 89.24; h, 5.40; n, 3.41. Measured elemental content (%): c, 89.27; h, 5.36; and N, 3.38.
Synthetic example 36: preparation of Compound 513
Compound 513(17.41g) was obtained in the same manner as in Synthesis example 1 except that d-2 in Synthesis example 1 was replaced with equimolar amount of d-513; the HPLC purity is more than or equal to 99.83 percent. Mass spectrum m/z: 794.3306 (theoretical value: 794.3297). Theoretical element content (%) C59H42N2O: c, 89.14; h, 5.33; and N, 3.52. Measured elemental content (%): c, 89.19; h, 5.28; and N, 3.49.
Synthetic example 37: preparation of Compound 517
Compound 517(21.32g) was obtained by the same preparation method as in Synthesis example 1 except that d-2 in Synthesis example 1 was replaced with equimolar d-187 and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.78 percent. Mass spectrum m/z: 934.3935 (theoretical value: 934.3923). Theoretical element content (%) C70H50N2O: c, 89.90; h, 5.39; and N, 3.00. Measured elemental content (%): c, 89.88; h, 5.44; and N, 2.96.
Synthetic example 38: preparation of Compound 560
Compound 560(18.13g) was obtained in the same manner as in Synthesis example 1 except that d-2 in Synthesis example 1 was replaced with equimolar d-560 and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.83 percent. Mass spectrum m/z:850.3371 (theoretical value: 850.3382). Theoretical element content (%) C62H46N2S: c, 87.49; h, 5.45; and N, 3.29. Measured elemental content (%): c, 87.52; h, 5.41; n, 3.43.
Synthetic example 39: preparation of Compound 570
Compound 570(19.71g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-6, b-2 was replaced with equimolar b-60, and g-2 was replaced with equimolar g-100; the HPLC purity is more than or equal to 99.81 percent. Mass spectrum m/z: 875.3342 (theoretical value: 875.3334). Theoretical element content (%) C63H45N3S: c, 86.37; h, 5.18; and N, 4.80. Measured elemental content (%): c, 86.35; h, 5.21; n, 4.77.
Synthetic example 40: preparation of Compound 660
Compound 660(16.16g) was obtained in the same manner as in Synthesis example 1 except that a-2 in Synthesis example 1 was replaced with equimolar a-230, b-2 was replaced with equimolar b-60, d-2 was replaced with equimolar d-71, and g-2 was replaced with equimolar g-102; the HPLC purity is more than or equal to 99.87 percent. Mass spectrum m/z: 708.2585 (theoretical value: 708.2599). Theoretical element content (%) C51H36N2S: c, 86.41; h, 5.12; and N, 3.95. Measured elemental content (%): c, 86.36; h, 5.09; and N, 4.01.
Device examples 1 to 40
The ITO glass substrate is ultrasonically cleaned for 2 times and 20 minutes each time by 5% glass cleaning solution, and then ultrasonically cleaned for 2 times and 10 minutes each time by deionized water. Ultrasonic cleaning with acetone and isopropanol for 20 min, and oven drying at 120 deg.C. HI-1 is evaporated on the ITO substrate in vacuum to be used as a hole injection layer, and the evaporation thickness is 15 nm; vacuum evaporating the compound 2 of the invention on the hole injection layer to form a hole transport layer, wherein the evaporation thickness is 80 nm; vacuum evaporating RH: RD 98:2 (mass ratio) on the hole transport layer to form a light emitting layer, wherein the evaporation thickness is 20 nm; vacuum evaporating ET-1 on the light-emitting layer to form an electron transport layer, wherein the evaporation thickness is 30 nm; evaporating LiF on the electron transport layer in vacuum to form an electron injection layer, wherein the evaporation thickness is 1 nm; al was vacuum-deposited on the electron injection layer as a cathode, and the deposition thickness was 70 nm.
Device embodiments 2 to 40: an organic electroluminescent device was produced by using the same procedure as in device example 1 except that the compound 2 of the present invention in device example 1 was replaced with the compounds 6, 25, 44, 49, 56, 60, 71, 100, 102, 108, 126, 136, 137, 140, 142, 146, 156, 180, 186, 187, 192, 202, 230, 231, 257, 279, 285, 336, 376, 391, 435, 441, 505, 510, 513, 517, 560, 570, 660, respectively, as a hole transporting material.
Comparative examples 1 to 2: an organic electroluminescent device was produced by using the same procedure as in device example 1 except that the compound 2 of the present invention in device example 1 was replaced with the compound 1 and the compound 2 as a hole transport layer, respectively.
The test software, computer, K2400 digital source meter manufactured by Keithley corporation, usa, and PR788 spectral scanning luminance meter manufactured by Photo Research corporation, usa were combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature.
The results of the light emission characteristic test of the obtained organic electroluminescent device are shown in table 1. Table 1 shows the results of the test of the light emitting characteristics of the organic electroluminescent devices prepared from the compounds prepared in the inventive examples and the comparative materials.
Device examples 41 to 40
The ITO glass substrate is ultrasonically cleaned for 2 times and 20 minutes each time by 5% glass cleaning solution, and then ultrasonically cleaned for 2 times and 10 minutes each time by deionized water. Ultrasonic cleaning with acetone and isopropanol for 20 min, and oven drying at 120 deg.C. HI-1 is evaporated on the ITO substrate in vacuum to be used as a hole injection layer, and the evaporation thickness is 15 nm; evaporating HT-1 on the hole injection layer in vacuum to form a hole transmission layer, wherein the evaporation thickness is 50 nm; vacuum evaporating the compound 44 of the invention on the hole transport layer to form a light-emitting auxiliary layer with the thickness of 40nm, and vacuum evaporating RH: RD (98: 2) on the light-emitting auxiliary layer to form a light-emitting layer with the thickness of 20 nm; vacuum evaporating ET-1 on the light-emitting layer to form an electron transport layer, wherein the evaporation thickness is 30 nm; evaporating LiF on the electron transport layer in vacuum to form an electron injection layer, wherein the evaporation thickness is 1 nm; al was vacuum-deposited on the electron injection layer as a cathode, and the deposition thickness was 70 nm.
Device embodiments 2 to 40: an organic electroluminescent device was produced by using the same procedure as in device example 41 except that the compound 44 of the present invention in device example 1 was replaced with the compound 136, 156, 230, 231, 279, 336, 435, 513, 517, 570 of the present invention as a light-emitting auxiliary layer material, respectively.
Comparative examples 1 to 2: an organic electroluminescent device was produced by using the same procedure as in device example 41 except that the compound 44 of the present invention in device example 41 was replaced with the compound 1 and the compound 2, respectively, as a light-emitting auxiliary layer material.
The test software, computer, K2400 digital source meter manufactured by Keithley corporation, usa, and PR788 spectral scanning luminance meter manufactured by Photo Research corporation, usa were combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature.
The results of the light emission characteristic test of the obtained organic electroluminescent device are shown in table 2. Table 2 shows the results of the test of the light emitting characteristics of the organic electroluminescent devices prepared by the compounds prepared in the inventive examples and the comparative materials.
It can be seen from tables 1 and 2 that when the benzidine derivative of the present invention is applied to an organic electroluminescent device as a hole transport layer material and a light-emitting auxiliary layer material, the light-emitting efficiency and the service life of the device are significantly improved. The benzidine derivative provided by the invention has good hole mobility, can balance the carrier transmission in the device, and improves the luminous efficiency of the device, and meanwhile, the benzidine derivative has good thermal stability and film-forming property, and can effectively prolong the service life of the device.
It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.
Claims (10)
1. A benzidine derivative is characterized in that the benzidine derivative has the structure shown as the following,
wherein, Ar is1Selected from the group consisting of the structures represented by chemical formula 2,
the ring A is selected from any one of the structures shown below,
ar is2～Ar4At least one of them is selected from the group consisting of the structure of chemical formula 3, and the others are the same or different and selected from any one of chemical formula 2, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C1-C25 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C3-C25 alicyclic ring and C2-C30 fused ring group, — N Ra and (Rb);
the Ra and the Rb are the same or different and are selected from any one of substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C3-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic ring, fused ring group of C6-C30 aromatic ring and substituted or unsubstituted C2-C30 heteroaryl;
x is selected from O or S;
the R is1、R2、R3The same or different groups are selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C3-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroarylAny one of the above;
n is1Selected from 0,1, 2,3 or 4; when n is1Greater than 1, two or more R1Are the same or different from each other, or adjacent R1May form a substituted or unsubstituted ring;
n is2Selected from 0,1, 2,3, 4,5, 6 or 7; when n is2Greater than 1, two or more R2Are the same or different from each other;
n is4Selected from 0,1, 2,3, 4,5, 6 or 7; when n is4Greater than 1, two or more R3Are the same or different from each other, or adjacent R3May form a substituted or unsubstituted ring;
said L1～L4Any one of the same or different single bonds, substituted or unsubstituted C3-C25 alicyclic group, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C3-C30 alicyclic group, substituted or unsubstituted C6-C30 aromatic ring fused cyclic group and substituted or unsubstituted C2-C30 heteroarylene group;
n is3Selected from 1,2, 3 or 4; when n3 is greater than 1, two or more
The same or different from each other.
2. The benzidine derivative according to claim 1, wherein the benzidine derivative is selected from any one of chemical formulas 1-1 to 1-8,
the R is1The same or different is selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylAny one of a phenyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentenyl group, a substituted or unsubstituted cyclohexenyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornane group, a substituted or unsubstituted piperidyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted carbazolyl group;
n is1Selected from 0,1, 2,3 or 4; when n is1Greater than 1, two or more R1Are the same or different from each other, or adjacent R1May form a substituted or unsubstituted ring therebetween.
3. The dianiline derivative of claim 1, wherein the chemical formula 3 is selected from any one of the following structures,
X0any one selected from O, S, C (Rc) (Rd) and N (Re);
the R is3Rc, Rd are the same or different and are selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted t-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornanyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenylAny one of substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the Re is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, Any one of substituted or unsubstituted carbazolyl groups.
4. The dianiline derivative of claim 1 or 3, wherein the chemical formula 3 is selected from any one of the following structures,
5. the dianiline derivative of claim 1, wherein the chemical formula 2 is selected from any one of the following structures,
6. the dianiline derivative of claim 1, wherein Ar is selected from the group consisting of2～Ar4At least one of them is selected from the group consisting of the structures represented by chemical formula 3, and the remaining same or different are selected from any one of chemical formula 2, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentenyl group, a substituted or unsubstituted cyclohexenyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted piperidyl group, or the structures represented below,
said Y is1、Y2The same or different is selected from O, S, C (Rf) (Rg) and N (Rh);
the R is4、R5、R6、R7Rf, Rg are the same or different and are selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted t-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryl, or substituted heteroaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryl, or substituted heteroaryl, or substituted or unsubstituted heteroaryl, or substituted or substituted or substituted or substituted or substituted or substituted or substituted or,Any one of substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornanyl, substituted or unsubstituted piperidyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the Rh is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, Any one of substituted or unsubstituted carbazolyl groups;
m is1Selected from 0,1, 2,3, 4 or 5; m is2Selected from 0,1, 2,3 or 4; m is3Selected from 0,1, 2,3, 4,5, 6 or 7; m is4Selected from 0,1, 2,3, 4,5, 6,7, 8 or 9; m is5Selected from 0,1, 2,3, 4,5, 6,7 or 8; when m is1、m2、m3、m4、m5Greater than 1, two or more R4Are the same or different from each other, two or more R5Are the same or different from each other, or adjacent R4May form a substituted or unsubstituted ring, adjacent R5May form a substitution or non-substitution betweenA substituted ring;
said L0Is selected from any one of single bond, substituted or unsubstituted arylene of C6-C18 and substituted or unsubstituted heteroarylene of C2-C18.
7. The dianiline derivative of claim 1, wherein Ar is selected from the group consisting of2～Ar4At least one of them is selected from the group consisting of the structures represented by chemical formula 3, and the remaining same or different are selected from the group consisting of chemical formula 2, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cyclopentenyl group, a substituted or unsubstituted cyclohexenyl group, or any one of the structures represented below,
8. the dianiline derivative of claim 1, wherein L is1～L4The same or different is selected from a single bond or any one of the structures shown below,
wherein, R is8、R9Any one of the same or different hydrogen, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl and substituted or unsubstituted C2-C12 heteroaryl;
k is1Identical or different from 0,1, 2,3 or 4, k2Identical or different from 0,1, 2,3, 4,5 or 6, k3Identical or different from 0,1, 2,3, 4,5, 6,7 or 8, k4The same or different is selected from 0,1, 2 or 3; when k is1、k2、k3、k4Greater than 1, two or more R9R being identical or different from each other, or adjacent to each other9May form a substituted or unsubstituted ring therebetween.
9. A benzidine derivative according to claim 1, wherein the benzidine derivative has any one of the structures shown below,
10. an organic electroluminescent device comprising an anode, a cathode, and an organic layer between and outside the anode and the cathode, wherein the organic layer comprises a hole transporting region, a light emitting layer, and an electron transporting region, and wherein the hole transporting region contains one or more of the benzidine derivatives according to any one of claims 1 to 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202210090065.4A CN114394949B (en) | 2022-01-25 | 2022-01-25 | Benzidine derivative and organic electroluminescent device thereof |
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| CN202210090065.4A CN114394949B (en) | 2022-01-25 | 2022-01-25 | Benzidine derivative and organic electroluminescent device thereof |
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| CN114394949A true CN114394949A (en) | 2022-04-26 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115417806A (en) * | 2022-09-30 | 2022-12-02 | 长春海谱润斯科技股份有限公司 | Carbazole compound and organic electroluminescent device thereof |
| WO2023160121A1 (en) * | 2022-02-25 | 2023-08-31 | 陕西莱特光电材料股份有限公司 | Organic compound, electronic element comprising same, and electronic device |
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| WO2014021569A1 (en) * | 2012-08-01 | 2014-02-06 | Sk Chemicals Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device including the same |
| CN110003090A (en) * | 2019-04-02 | 2019-07-12 | 北京诚志永华显示科技有限公司 | Indene derivative, the organic electroluminescence device containing indene derivative |
| CN113717057A (en) * | 2020-05-26 | 2021-11-30 | 三星显示有限公司 | Amine compound and organic light emitting device including the same |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014021569A1 (en) * | 2012-08-01 | 2014-02-06 | Sk Chemicals Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device including the same |
| CN110003090A (en) * | 2019-04-02 | 2019-07-12 | 北京诚志永华显示科技有限公司 | Indene derivative, the organic electroluminescence device containing indene derivative |
| CN113717057A (en) * | 2020-05-26 | 2021-11-30 | 三星显示有限公司 | Amine compound and organic light emitting device including the same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023160121A1 (en) * | 2022-02-25 | 2023-08-31 | 陕西莱特光电材料股份有限公司 | Organic compound, electronic element comprising same, and electronic device |
| CN115417806A (en) * | 2022-09-30 | 2022-12-02 | 长春海谱润斯科技股份有限公司 | Carbazole compound and organic electroluminescent device thereof |
| CN115417806B (en) * | 2022-09-30 | 2024-02-20 | 长春海谱润斯科技股份有限公司 | Carbazole compound and organic electroluminescent device thereof |
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