CN117263964A - Condensed heterocyclic compound, application thereof and organic electroluminescent device containing same - Google Patents
Condensed heterocyclic compound, application thereof and organic electroluminescent device containing same Download PDFInfo
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- CN117263964A CN117263964A CN202310099414.3A CN202310099414A CN117263964A CN 117263964 A CN117263964 A CN 117263964A CN 202310099414 A CN202310099414 A CN 202310099414A CN 117263964 A CN117263964 A CN 117263964A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 83
- 230000000903 blocking effect Effects 0.000 claims description 18
- -1 isobutenyl Chemical group 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000005264 aryl amine group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 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 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005104 aryl silyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- JFDZBHWFFUWGJE-KWCOIAHCSA-N benzonitrile Chemical group N#[11C]C1=CC=CC=C1 JFDZBHWFFUWGJE-KWCOIAHCSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002979 perylenes Chemical group 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052711 selenium Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000003518 tetracenes Chemical group 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 abstract description 7
- 239000007787 solid Substances 0.000 abstract description 7
- 230000002776 aggregation Effects 0.000 abstract description 6
- 238000004220 aggregation Methods 0.000 abstract description 6
- 238000010791 quenching Methods 0.000 abstract description 6
- 238000010586 diagram Methods 0.000 abstract description 3
- 238000000295 emission spectrum Methods 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 178
- 230000015572 biosynthetic process Effects 0.000 description 114
- 238000003786 synthesis reaction Methods 0.000 description 114
- 239000010410 layer Substances 0.000 description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 57
- 239000000126 substance Substances 0.000 description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000001819 mass spectrum Methods 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000004949 mass spectrometry Methods 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 238000002390 rotary evaporation Methods 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000010408 film Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000007789 gas Substances 0.000 description 17
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 14
- 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 14
- 238000000605 extraction Methods 0.000 description 12
- 238000000926 separation method Methods 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 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 9
- 238000007385 chemical modification Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229940117389 dichlorobenzene Drugs 0.000 description 5
- 239000002346 layers by function Substances 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QXISTPDUYKNPLU-UHFFFAOYSA-N 2-bromo-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Br)=C1 QXISTPDUYKNPLU-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical class [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
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- 150000002894 organic compounds Chemical class 0.000 description 2
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- 239000002994 raw material Substances 0.000 description 2
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- GMMUCVGZXGOUNM-UHFFFAOYSA-N (2-bromo-4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1Br GMMUCVGZXGOUNM-UHFFFAOYSA-N 0.000 description 1
- BHXVZYJULSWULU-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)boronic acid Chemical group OB(O)C1=CC=C(F)C=C1Br BHXVZYJULSWULU-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- NFWPHICGKMNNGG-UHFFFAOYSA-N 1-N,3-N-bis(4-tert-butylphenyl)benzene-1,3-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=CC(NC=2C=CC(=CC=2)C(C)(C)C)=C1 NFWPHICGKMNNGG-UHFFFAOYSA-N 0.000 description 1
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- JXMZUNPWVXQADG-UHFFFAOYSA-N 1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1I JXMZUNPWVXQADG-UHFFFAOYSA-N 0.000 description 1
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 1
- WVNGSNHHAXMXAM-UHFFFAOYSA-N 2-bromo-1,3-ditert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1Br WVNGSNHHAXMXAM-UHFFFAOYSA-N 0.000 description 1
- USMQLFCVCDEXAK-UHFFFAOYSA-N 2-bromo-4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Br USMQLFCVCDEXAK-UHFFFAOYSA-N 0.000 description 1
- XNKAPUCNAVBLOL-UHFFFAOYSA-N 2-bromo-4-tert-butyl-1-iodobenzene Chemical compound CC(C)(C)C1=CC=C(I)C(Br)=C1 XNKAPUCNAVBLOL-UHFFFAOYSA-N 0.000 description 1
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- GUTJITRKAMCHSD-UHFFFAOYSA-N 9,9-dimethylfluoren-2-amine Chemical group C1=C(N)C=C2C(C)(C)C3=CC=CC=C3C2=C1 GUTJITRKAMCHSD-UHFFFAOYSA-N 0.000 description 1
- DCLQWKLHMHQVTE-UHFFFAOYSA-N BrC=1C=C(C=CC=1)C1=CC(=CC(=C1)C(C)(C)C)C(C)(C)C Chemical group BrC=1C=C(C=CC=1)C1=CC(=CC(=C1)C(C)(C)C)C(C)(C)C DCLQWKLHMHQVTE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention provides a condensed heterocyclic compound, application thereof and an organic electroluminescent device containing the compound. In one aspect of the invention, as shown in the schematic diagram, the structure within the ring constitutes oneA rigid planar core element, thereby facilitating the achievement of high luminous efficiency and a narrow half-width emission spectrum. On the other hand, by R outside the core 13 、R 14 The unit can effectively inhibit aggregation quenching and exciplex generation caused by pi-pi action among molecules. Thus, the luminescent property of the material in the solid film can be remarkably improved, and the efficiency and the service life of the electroluminescent device are improved.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a novel organic compound and application thereof, and an organic electroluminescent device containing the compound.
Background
An organic electroluminescent device (OLED: organic Light Emitting Devices) is a sandwich-like current driven thin film device with a single or multiple layers of organic functional material sandwiched between an anode and a cathode. The OLED has the characteristics of self-luminescence, wide visual angle, wide color gamut, short response time, high luminous efficiency, low working voltage, low cost, simple production process and the like, and is widely applied to display products such as televisions, smart phones, tablet computers, vehicle-mounted display, illumination and the like, and further applied to creative display products such as large-size display and flexible screens.
The organic photoelectric material applied to the OLED device may be classified into a light emitting layer material and an auxiliary functional layer material in use, wherein the light emitting layer material includes a guest material (also referred to as a light emitting material, a doping material) and a host material (also referred to as a host material), the light emitting material is classified into a fluorescent material, a phosphorescent material and a thermally activated delayed fluorescent material according to different energy transfer modes, and the auxiliary functional layer material is classified into an electron injecting material, an electron transporting material, a hole blocking material, an electron blocking material, a hole transporting material and a hole injecting material according to different properties of electron or hole transporting speed.
The luminescent dopant used in the luminescent layer has a decisive influence on the color, efficiency, stability and other properties of the electroluminescent device. However, currently luminescent dopant materials with high efficiency, narrow emission are still very lacking. The existing blue light-emitting doping materials have the problems of low efficiency, short service life, insufficient color purity and the like, such as boron-nitrogen compounds in patents (CN 107417715A, withdrawal, 7 months and 14 days of application date 2017) and documents (adv. Mater.2016,28, 2777-2781), and narrower half-peak width can be realized due to the multiple resonance effects of the boron-nitrogen structure. However, the molecular structure has low luminous efficiency and is easy to aggregate, so that the efficiency and the service life are reduced.
Therefore, there is a need in the art to develop OLED luminescent materials that have high luminous efficiency and narrow emission spectrum, while effectively inhibiting intermolecular aggregation. When the material is applied to an organic electroluminescent device, the material has the advantages of high efficiency, long service life, high color purity and the like.
Prior art literature
Patent document 1: CN107417715a, withdrawn, filing date 2017, 7, 14
Non-patent document 1: adv. Mater.2016,28,2777-2781
Disclosure of Invention
The present invention is directed to solving the above-mentioned problems, and in the present invention, on the one hand, as shown in the schematic diagram, the structure in the ring constructs a rigid planar core unit, thereby facilitating to obtain an emission spectrum with high luminous efficiency and narrow half-peak width. On the other hand, by R outside the core 13 、R 14 The unit can effectively inhibit aggregation quenching and exciplex generation caused by pi-pi action among molecules. Thus, the luminescent property of the material in the solid film can be remarkably improved, and the efficiency and the service life of the electroluminescent device are improved.
Specifically, the present invention provides: 1) A condensed heterocyclic compound represented by the following general formula (1):
wherein Y represents NR 21 An O atom, an S atom, and a Se atom;
R 1 ～R 12 each independently selected from: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, and substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms;
R 1 ～R 12 optionally can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring;
R 13 、R 14 each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted silicon group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 40 ring-forming carbon atoms;
R 13 And R is 14 Optionally bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring;
R 21 selected from: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms.
R 21 Optionally may bond with adjacent groups to form substituted or unsubstituted saturated or unsaturated rings;
provided that the compound is not a molecule of the following:
2) The fused heterocyclic compound according to 1), wherein Y is NR 21 。
3) The fused heterocyclic compound according to 1), wherein R 1 ～R 14 Each independently selected from: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted n-pentyl, substituted or unsubstituted sec-pentyl, substituted or unsubstituted trifluoromethyl, substituted or unsubstituted pentafluoroethyl, substituted or unsubstituted 2, 2-trifluoroethyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, substituted or unsubstituted n-butenyl, substituted or unsubstituted isobutenyl, substituted or unsubstituted n-pentenyl, substituted or unsubstituted isopentenyl, substituted or unsubstituted neopentenyl, substituted or unsubstituted ethynyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted Substituted or unsubstituted phenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted indenofluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstitutedA group, a substituted or unsubstituted naphthacene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzothiazyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzoselenophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted triphenylphosphine oxide group, a substituted or unsubstituted benzonitrile group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group;
R 1 ～R 12 The substituent groups can also be selected from any one or more of the following groups: in hydrogen, deuterium, fluorine, chlorine, bromine atoms
4) The fused heterocyclic compound according to 1), wherein R 13 And R is 14 Are bonded to each other to form a ring represented by the following formulas (2-1) to (2-7):
wherein R is 31 ～R 39 The substituent groups are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted silicon group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to more carbon atoms20, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted 1-valent heterocyclic group having 5 to 50 ring-forming carbon atoms.
5) The fused heterocyclic compound according to 1), wherein R 13 And R is 14 Independently selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
6) The fused heterocyclic compound according to 1), wherein R 13 And R is 14 Are bonded to each other to form a substituted or unsubstituted cyclobutane having 4 to 50 carbon atoms, a substituted or unsubstituted cyclopentane having 5 to 50 carbon atoms, a substituted or unsubstituted cyclohexane having 6 to 50 carbon atoms, or adamantane.
7) The fused heterocyclic compound according to 1), wherein the fused heterocyclic compound is selected from the following structures:
8) An organic electroluminescent device, wherein the organic electroluminescent device comprises an anode, a cathode and at least one layer of organic film between the anode and the cathode, wherein the organic film contains the compound of any one of 1) to 7).
9) The organic electroluminescent device according to 8), wherein the organic thin film comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an exciton blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one of the light emitting layers contains the compound of any one of 1) to 7).
10 The organic electroluminescent device according to 8) or 9), wherein the compound is used as a fluorescent material of a light emitting layer in the organic electroluminescent device
Compared with the prior art, the invention has the beneficial effects that: the OLED device prepared by the compound has the characteristics of narrower half-peak width and heat activation delayed fluorescence, and greatly improves the luminous efficiency and the color purity of the material with multiple resonance-heat activation delayed fluorescence; the fluorescent lamp has low starting voltage, high luminous efficiency and better service life, can meet the requirement of the current display industry on high-performance luminous materials, and has good application prospect.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this application, illustrate embodiments of the application and together with the description serve to explain the application and do not constitute an undue limitation to the application. In the drawings:
FIG. 1 is a schematic diagram of an organic electroluminescent device to which the compound of the present invention is applied, wherein the structure of each layer of the device is represented as follows:
1. transparent substrate layer, 2, ITO anode layer, 3, hole injection layer, 4, hole transport layer A,5, hole transport layer B (or electron blocking layer), 6, luminescent layer, 7, electron transport layer B (or hole blocking layer), 8, electron transport layer A,9, electron injection layer, 10, cathode reflection electrode layer.
Detailed Description
The principles and features of the present invention will be further illustrated by the following examples of various synthetic embodiments, which are provided for purposes of illustration only and are not intended to limit the scope of the invention.
A method for synthesizing the specific compound of formula (1) listed below.
Synthetic examples
Synthesis example 1: synthesis of Compound 1
Synthesis of intermediate 1 a: 14.5g (50 mmol) of 2-bromoiodobenzene, 22.7g (50 mmol) of 2, 3-dichloroaniline, 0.91g (1 mmol) of tris (dibenzylideneacetone) dipalladium, 4.4g (8 mmol) of 1,1' -bis (diphenylphosphine) ferrocene and 5.76g (60 mmol) of tert-butanol are weighed out Sodium was added to 100ml of toluene. The reaction was refluxed overnight at 120℃under nitrogen and with the help of a gas pump. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. About 12.9g of intermediate 1a was isolated by silica gel column chromatography, 82% yield, mass spectrum molecular weight m/z=313.9 [ m-H ] - ]。
Synthesis of intermediate 1 b: 12.5g (40 mmol) of intermediate 1a, 0.066g (0.4 mmol) of palladium acetate, 0.23g (0.8 mmol) of tricyclohexylphosphine and 10.9g (80 mmol) of potassium carbonate are weighed into 60ml of DMF. Pumping gas, protecting with nitrogen, and reacting for 4h at 120 ℃. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. About 7.9g of intermediate 1b was isolated by silica gel column chromatography, 84% yield, mass spectrum molecular weight m/z=233.1 [ m-H ] - ]。
Synthesis of intermediate 1 c: 7.06g (30 mmol) of intermediate 1b, 9.17g (35 mmol) of methyl 2-iodobenzoate, 0.38g (6 mmol) of copper powder, and 10.9g (80 mmol) of potassium carbonate were weighed into 60ml of o-dichlorobenzene. The reaction is carried out for 24 hours at 180 ℃ under the protection of nitrogen and the gas extraction. Cooling to room temperature, distilling under reduced pressure to remove dichlorobenzene, extracting with ethyl acetate/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. About 7.53g of intermediate 1c was isolated by silica gel column chromatography, 68% yield, mass spectrum molecular weight m/z=369.1 [ m ] + ]。
Synthesis of intermediate 1 d: 7.38g (20 mmol) of intermediate 1c are weighed into 60ml of anhydrous tetrahydrofuran, and 25ml (2.0M, 50 mmol) of methyl magnesium bromide in THF are added dropwise under nitrogen and reacted at room temperature for 1h. Quenching with water, extracting with ethyl acetate/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. 50ml of methylene chloride was added thereto to dissolve the mixture, and 2.8g (20 mmol) of boron trifluoride etherate was added dropwise thereto to react at room temperature for 1 hour. Quenching with water, neutralizing with sodium carbonate solution, extracting with dichloromethane/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. The separation on a silica gel column gives intermediate 1d of about 6.18g in 88% yield, mass spectrometry molecular weight m/z=351.2 [ m ] + ]。
Synthesis of intermediate 1 e: 7.02g (20 mmol) of intermediate 1d, 5.35g (20 mmol) of N-p-tert-butylphenyl-2, 4, 6-trimethylaniline, 0.91g (1 mmol) of tris (dibenzylideneacetone) dipalladium, 1.76g (8 mmol) of tri-tert-butylphosphine and 2.88g (30 mmol) of sodium tert-butoxide are weighed into 60ml of tolueneIs a kind of medium. The reaction was refluxed overnight at 120℃under nitrogen and with the help of a gas pump. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The separation on a silica gel column gives intermediate 1e about 8.38g in 72% yield, mass spectrometry molecular weight m/z=582.4 [ m ] + ]。
Synthesis of chemical formula 1: 5.82g (10 mmol) of intermediate 1d are weighed into dry 50ml of anhydrous xylene, nitrogen-protected, 16.7ml of tert-butyllithium solution (20 mmol, 1.2M) are added dropwise at 0℃and the mixture is stirred for 1h at 60 ℃. Returning to room temperature, 7.5g (30 mmol) of boron tribromide was added thereto and stirred at room temperature for 0.5h. 5.16g (40 mmol) of diisopropylethylamine was added thereto, and the mixture was heated to 140℃to react for 6 hours. Stopping the reaction, cooling to room temperature, slowly adding into sodium carbonate solution to neutralize to neutrality, extracting with dichloromethane three times, collecting organic phase, spin-drying solvent, separating with silica gel column, and recrystallizing with dichloromethane and ethanol to obtain 0.72g target product. Yellow solid, 13% yield, mass spectrometry molecular weight m/z=556.4 [ m + ]。
Synthesis example 2: synthesis of chemical modification 17
Synthesis of intermediate 2 a: 7.02g (20 mmol) of N1, N3-bis (4- (tert-butyl) phenyl) benzene-1, 3-diamine, 5.35g (20 mmol) of 2-bromo-paraxylene, 0.91g (1 mmol) of tris (dibenzylideneacetone) dipalladium, 1.76g (8 mmol) of tri-tert-butylphosphine and 2.88g (30 mmol) of sodium tert-butoxide were weighed into 60ml of toluene. The reaction is carried out for 2 hours at 80 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. About 5.9g of intermediate 2a was isolated by silica gel column chromatography, 62% yield, mass spectrum molecular weight m/z=476.7 [ m ] + ]。
Synthesis of intermediate 2 b: n-p-tert-butylphenyl-2, 4, 6-trimethylaniline in the synthesis of intermediate 1e is replaced with intermediate 2a, the same reaction conditions result in 10.3g of intermediate 2b in 65% yield, mass spectrum with molecular weight m/z=791.5 [ m ] + ]。
Synthesis of chemical formula 17: the intermediate 1e in the synthesis of the chemical formula 1 is replaced by the intermediate 2b, and the same is adoptedCan obtain 1.07g of 17 with yield of 14%, and mass spectrum measuring molecular weight m/z=765.5 [ M ] + ]。
Synthesis example 3: synthesis of chemical modification 18
Synthesis of intermediate 3 a: substitution of 2-bromo-para-xylene in the synthesis of intermediate 2a to 2-bromobiphenyl, the same reaction conditions, yielded 5.35g of intermediate 3a in 61% yield, mass spectrometry molecular weight m/z=524.4 [ m ] + ]。
Synthesis of intermediate 3 b: n-p-tert-butylphenyl-2, 4, 6-trimethylaniline in the synthesis of intermediate 1e is replaced with intermediate 3a, the same reaction conditions give 10.4g of intermediate 3b in 62% yield, mass spectrum with molecular weight m/z=839.5 [ M ] + ]。
Synthesis of chemical 18: substituting intermediate 1e in the synthesis of chemical 1 for intermediate 3b, the same reaction conditions gave 0.90g of chemical 18 in 11% yield, mass spectrum measured molecular weight m/z=813.5 [ m ] + ]。
Synthesis example 4: synthesis of chemical modification 46
Synthesis of intermediate 4 a: 7.08g (30 mmol) of intermediate 1b, 9.87g (35 mmol) of 2-bromoiodobenzene, 0.38g (6 mmol) of copper powder, and 10.9g (80 mmol) of potassium carbonate were weighed into 60ml of o-dichlorobenzene. The reaction is carried out for 24 hours at 180 ℃ under the protection of nitrogen and the gas extraction. Cooling to room temperature, distilling under reduced pressure to remove dichlorobenzene, extracting with ethyl acetate/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. About 4.1g of intermediate 4a was isolated by silica gel column chromatography, yield 35%, mass spectrum measuring molecular weight m/z=388.9 [ m ] + ]。
Synthesis of intermediate 4 b: weigh (10 mmol) intermediate 4a in 30ml dry THF, -70 ℃ under nitrogen, add dropwise 4.0ml (2.5 m,10 mmol) of n-butyllithium hexane solution; reacting for 0.5h at low temperature, adding (10 mmol) 9-fluorenone, Low temperature reaction for 1h and natural return to room temperature for 2h. Quenching with water, extracting with ethyl acetate/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. 50ml of methylene chloride was added thereto to dissolve the mixture, and 1.4g (10 mmol) of boron trifluoride etherate was added dropwise thereto to react at room temperature for 1 hour. Quenching with water, neutralizing with sodium carbonate solution, extracting with dichloromethane/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. The intermediate 4b was isolated by silica gel column separation to give about 3.6g of intermediate with a yield of 76%, mass spectrometry molecular weight m/z=473.1 [ m ] + ]。
Synthesis of intermediate 4 c: 4.73g (10 mmol) of intermediate 4b, 5.24g (10 mmol) of intermediate 3a, 0.45g (0.5 mmol) of tris (dibenzylideneacetone) dipalladium, 0.88g (4 mmol) of tri-tert-butylphosphine and 1.44g (15 mmol) of sodium tert-butoxide were weighed into 30ml of toluene. The reaction was refluxed overnight at 120℃under nitrogen and with the help of a gas pump. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The separation on a silica gel column gives intermediate 4c about 6.92g in 72% yield, mass spectrometry molecular weight m/z=961.5 [ m ] + ]。
Synthesis of chemical formula 46: the same reaction conditions can give 1.50g of 46, 16% yield, yellow solid, mass spectrum with molecular weight m/z=935.5 [ m ] by substituting intermediate 1e in the synthesis of chemical 1 with intermediate 4c + ]。
Synthesis example 5: synthesis of chemical modification 73
Synthesis of intermediate 5 a: 5.18g (20 mmol) of 4-1' -dibenzofuran, 5.38g (20 mmol) of m-di-tert-butylbromobenzene, 0.91g (1 mmol) of tris (dibenzylideneacetone) dipalladium, 1.76g (8 mmol) of tri-tert-butylphosphine and 2.88g (30 mmol) of sodium tert-butoxide are weighed into 60ml of toluene. The reaction is carried out for 2 hours at 80 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The intermediate 5a was isolated by silica gel column chromatography in about 7.78g, 87% yield, mass spectrometry molecular weight m/z=447.3 [ m ] + ]。
Synthesis of intermediate 5 b: intermediate 3a in the synthesis of intermediate 4c is replaced by intermediate 5a, phaseThe same reaction conditions gave 7.07g of intermediate 5b in 82% yield, mass spectrum with molecular weight m/z=884.5 [ m ] + ]。
Synthesis of chemical 18: the same reaction conditions can give 1.29g of 18 with 15% yield, mass spectrum with molecular weight m/z=858.4 [ m ] by substituting intermediate 1e in the synthesis of chemical 1 with intermediate 5b + ]。
Synthesis example 6: synthesis of chemical modification 74
Synthesis of intermediate 6 a: 4-1 '-dibenzofuranylaniline in the synthesis of the intermediate 5a is replaced by the intermediate 2-isopropyl [1,1' -biphenyl ]]-4-amine, the same reaction conditions gave 6.94g of intermediate 6a in 87% yield, mass spectrometry molecular weight m/z=399.4 [ m + ]。
Synthesis of intermediate 6 b: replacing intermediate 3a in the synthesis of intermediate 4c with intermediate 6a, the same reaction conditions gave 7.02g of intermediate 6b in 85% yield, mass spectrometry molecular weight m/z=836.4 [ m + ]。
Synthesis of chemical 74: the same reaction conditions can give 1.13g of 74, 14% yield, mass spectrum with molecular weight m/z=810.5 [ m ] by substituting intermediate 1e in the synthesis of chemical 1 with intermediate 6b + ]。
Synthesis example 7: synthesis of chemical modification 77
Synthesis of intermediate 7 a: 4-1' -Dibenzofuranylaniline in the synthesis of intermediate 5a was replaced by intermediate 2' - (9-hydrogen carbazole-9) - [1,1' -biphenyl ]]-4-amine, the same reaction conditions gave 7.33g of intermediate 7a in 81% yield, mass spectrum with molecular weight m/z=452.3 [ m + ]。
Synthesis of intermediate 7 b: the intermediate 3a in the synthesis of intermediate 4c was replaced with intermediate 7a, and the same reaction conditions gave 7.20g of intermediate 7b, yield 81%, mass spectrum molecular weight m/z=889.4 [ m ] + ]。
Synthesis of chemical 77: substituting intermediate 1e in the synthesis of chemical 1 for intermediate 7b, the same reaction conditions gave 0.95g of chemical 77 in 11% yield, mass spectrum measured molecular weight m/z=863.4 [ m ] + ]。
Synthesis example 8: synthesis of chemical formula 102
Synthesis of intermediate 8 a: the synthesis of intermediate 8a was replaced with 2-amino-9, 9-dimethylfluorene by 4-1' -dibenzofuranylaniline, and the same reaction conditions gave 5.92g of intermediate 8a in a yield of 72%, mass spectrometry molecular weight m/z=411.3 [ m ] + ]。
Synthesis of intermediate 8 b: the same reaction conditions can give 5.35g of intermediate 8b in 62% yield, mass spectrometry molecular weight m/z=848.4 [ m ] by substituting intermediate 3a for intermediate 8a in the synthesis of intermediate 4c + ]。
Synthesis of chemical 102: the same reaction conditions can give 1.23g of 102 in 15% yield, mass spectrum with molecular weight m/z=822.5 [ m ] by substituting intermediate 1e in the synthesis of chemical 1 for intermediate 8b + ]。
Synthesis example 9: synthesis of chemical modification 6
Synthesis of intermediate 9 a: 6.88g (20 mmol) of 3' -bromo-3, 5-di-tert-butyl-1, 1' -biphenyl and 4.50g (20 mmol) of 5-tert-butyl- [1,1' -biphenyl were weighed out]2-amine, 0.91g (1 mmol) of tris (dibenzylideneacetone) dipalladium, 1.76g (8 mmol) of tri-tert-butylphosphine and 2.88g (30 mmol) of sodium tert-butoxide are added to 60ml of toluene. The reaction is carried out for 2 hours at 80 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The separation on a silica gel column gives intermediate 9a about 8.71g in 89% yield and mass spectrometry molecular weight m/z=489.4 [ m + ]。
Synthesis of intermediate 9 b: substitution of 2-bromoiodobenzene in the synthesis of intermediate 4a with 4-tert-butyl-2-bromoiodobenzene gives 5.47g of intermediate 9b in 41% yield as a yellow solid with mass spectrometry molecular weight m/z=445.1 [ m ] + ]。
Synthesis of intermediate 9 c: the same reaction conditions can give 3.67g of intermediate 9c with a yield of 69%, a yellow solid, and a mass spectrum of molecular weight m/z=531.2 [ m ] by substituting intermediate 4a for intermediate 9b, 9-fluorenone for benzophenone in the synthesis of intermediate 4b + ]。
Synthesis of intermediate 9 d: 4.89g (10 mmol) of intermediate 9a, 5.31g (10 mmol) of intermediate 9c, 0.45g (0.5 mmol) of tris (dibenzylideneacetone) dipalladium, 0.88g (4 mmol) of tri-tert-butylphosphine and 1.44g (15 mmol) of sodium tert-butoxide were weighed into 30ml of toluene. The reaction was refluxed overnight at 120℃under nitrogen and with the help of a gas pump. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The silica gel column separation gives about 7.18g of intermediate 9d, 73% yield, mass spectrometry molecular weight m/z=984.5 [ m ] + ]。
Synthesis of chemical formula 6: the same reaction conditions can give 1.43g of 6 in 15% yield as a yellow solid with mass spectrometry molecular weight m/z=958.6 [ m ] by substituting intermediate 1e in the synthesis of chemical 1 for intermediate 9d + ]。
Synthesis example 10: synthesis of chemical modification 143
Synthesis of intermediate 10 a: substitution of the intermediate benzophenone in the synthesis of chemical formula 6 with 9-fluorenone, the same reaction conditions gave 3.97g of intermediate 10a in 75% yield, mass spectrum measured molecular weight m/z=529.1 [ m ] + ]。
Synthesis of intermediate 10 b: the same reaction conditions can give 6.33g of intermediate 10b with 82% yield, mass spectrometry molecular weight m/z= 772.4[ by substituting intermediate 3a for 3, 6-di-tert-butylcarbazole and intermediate 4b for intermediate 10a in the synthesis of intermediate 4cM + ]。
Synthesis of chemical formula 143: the same reaction conditions can give 1.12g of the reaction 143, 15% yield, mass spectrum molecular weight m/z=746.4 [ m ] by substituting intermediate 1e in the synthesis of chemical 1 with intermediate 10b + ]。
Synthesis example 11: synthesis of chemical modification 185
Synthesis of intermediate 11 a: substitution of the intermediate benzophenone in the synthesis of chemical 6 with xanthone, the same reaction conditions, gave 4.08g of intermediate 11a in 75% yield, mass spectrum measured molecular weight m/z=545.1 [ m ] + ]。
Synthesis of intermediate 11 b: the same reaction conditions can give 7.9g of intermediate 11b in 79% yield, mass spectrometry molecular weight m/z=998.5 [ m ] by substituting intermediate 4b in the synthesis of intermediate 4c for intermediate 11a + ]。
Synthesis of chemical formula 185: the same reaction conditions can give 1.17g of the compound 185 in 12% yield, with mass spectrometry of molecular weight m/z=972.5 [ m ] by substituting intermediate 1e in the synthesis of the compound 1 with intermediate 11b + ]。
Synthesis example 12: synthesis of chemical 82
Synthesis of intermediate 12 a: 4.98g (20 mmol) of 2-iodonitrobenzene, 5.58g (20 mmol) of 2-bromo-4-chlorobenzeneboronic acid, 0.6g (0.5 mmol) of palladium tetraphenylphosphine and 4.08g (30 mmol) of potassium carbonate are weighed into 60ml of toluene, 15ml of ethanol and 15ml of water. The reaction is carried out for 8 hours at 80 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. About 5.16g of intermediate 12a was isolated by silica gel column chromatography, 83% yield, mass spectrum molecular weight m/z=310.9 [ m ] + ]。
Synthesis of intermediate 12 b: 6.22g (20 mmol) of intermediate 12a and 13.1g (50 mmol) of triphenyl are weighed out50ml of dichlorobenzene was added to the alkylphosphine. The reaction is carried out for 18h at 180 ℃ under the protection of nitrogen and the gas extraction. Cooling to room temperature, distilling under reduced pressure to remove dichlorobenzene, extracting with ethyl acetate/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. The silica gel column separation gave intermediate 12b at about 4.94g, 76% yield, mass spectrometry molecular weight m/z=277.9 [ m-H ] - ]。
Synthesis of intermediate 12 c: 2.79g (10 mmol) of intermediate 12b, 1.98g (10 mmol) of 2-boric acid biphenyl, 0.6g (0.5 mmol) of tetrakis triphenylphosphine palladium and 2.76g (20 mmol) of potassium carbonate are weighed into 60ml of toluene, 15ml of ethanol and 15ml of water. The reaction is carried out for 20h at 90 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The silica gel column separated about 2.58g of intermediate 12c, 73% yield, mass spectrometry molecular weight m/z=353.1 [ m ] + ]。
Synthesis of intermediate 12 d: 3.53g (10 mmol) of intermediate 12c and 2.08g (12 mmol) of 2-bromofluorobenzene are weighed into 30ml of DMF. The reaction is carried out for 12 hours at 150 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The silica gel column separation gives intermediate 12d about 4.81g in 87% yield, mass spectrometry molecular weight m/z=508.8 [ m ] + ]。
Synthesis of intermediate 12 e: the starting intermediate 4a in the synthesis of intermediate 4b was replaced by intermediate 12d, and under the same reaction conditions, intermediate 12e,2.43g, 41% yield, mass spectrum molecular weight m/z=591.2 [ m ] was obtained + ]。
Synthesis of intermediate 12 f: 5.91g (10 mmol) of intermediate 12e, 2.81g (10 mmol) of di- (4-tert-butylphenyl) amine, 0.45g (0.5 mmol) of tris (dibenzylideneacetone) dipalladium, 0.88g (4 mmol) of tri-tert-butylphosphine and 1.44g (15 mmol) of sodium tert-butoxide are weighed into 40ml of toluene. The reaction is carried out for 16h at 120 ℃ under the protection of nitrogen and the pumping gas. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The intermediate 12f was isolated by silica gel column separation at about 6.86g, 82% yield, mass spectrum molecular weight m/z=836.4 [ m ] + ]。
Synthesis of chemical 82: 5.02g (6 mmol) of intermediate 12f, 3.0g (12 mmol) of boron tribromide are weighed into 30ml of dichlorobenzene. Nitrogen protection at 180 DEG CThe reaction was carried out for 20h. Cooling to room temperature, adding into sodium carbonate solution for neutralization, extracting with ethyl acetate/water, drying with anhydrous sodium sulfate, and concentrating by rotary evaporation. Silica gel column separation and recrystallisation from methylene chloride/methanol gives 82.25 g of target molecularly ofabout 82.25 g, 5% yield, mass spectrum molecular weight m/z=844.4 [ m ] + ]。
Synthesis example 13: synthesis of chemical 166
Synthesis of intermediate 13 a: 2-bromo-4-chlorobenzoic acid in the synthesis of intermediate 12a was replaced with 2-bromo-4-fluorobenzeneboronic acid, and intermediate 13a,2.39g, yield 81%, mass spectrum measured molecular weight m/z=295.0 [ m ] was obtained under the same reaction conditions + ]。
Synthesis of intermediate 13 b: the raw material intermediate 12a in the synthesis of intermediate 12b is replaced by intermediate 13a, and under the same reaction conditions, intermediate 13b,1.97g, yield 75% and mass spectrum measurement molecular weight m/z=261.9 [ m-H ] can be obtained - ]。
Synthesis of intermediate 13 c: the raw material intermediates 12b and 2-boric acid biphenyl in the synthesis of the intermediate 12c are replaced by the intermediate 13b and phenylboric acid, and the intermediate 13c can be obtained under the same reaction conditions, 2.0g, the yield is 77%, and the mass spectrometry molecular weight m/z=260.1 [ m-H ] - ]。
Synthesis of intermediate 13 d: the starting intermediate 12c in the synthesis of intermediate 12d was replaced by intermediate 13c, and under the same reaction conditions, intermediate 13d,3.44g, 83% yield, mass spectrum molecular weight m/z=415.1 [ m ] was obtained + ]。
Synthesis of intermediate 13 e: the starting intermediate 4a in the synthesis of intermediate 4b was replaced by intermediate 13d, and under the same reaction conditions, intermediate 13e,2.35g, yield 47%, mass spectrometry molecular weight m/z=499.2 [ m ] was obtained + ]。
Synthesis of intermediate 13 f: 2.2g (10 mmol) of 4-bromo-2-anisole, 2.53g (10 mmol) of N- (4-tert-butylphenyl) -2, 4-dimethylaniline, 0.45g (0.5 mmol) of tris (dibenzylideneacetone) dipalladium, 0.88g (4 mmol) are weighed outTri-tert-butylphosphine and 1.44g (15 mmol) of sodium tert-butoxide are added to 40ml of toluene. The reaction is carried out for 12 hours at 100 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The intermediate 13f was isolated by silica gel column separation in about 3.22g, 82% yield, mass spectrum with molecular weight m/z=393.2 [ m ] + ]。
Synthesis of intermediate 13 g: 3.93g (10 mmol) of intermediate 13f are weighed out and dissolved in 50ml of dichloromethane, under nitrogen. 15ml (15 mmol, 1.0M) of boron tribromide in methylene chloride are added dropwise at-70℃and reacted for 10h. The reaction was quenched, extracted with dichloromethane/water, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation. The intermediate 13f was isolated on a silica gel column at about 3.21g in 85% yield and mass spectrum with molecular weight m/z=378.2 [ m-H ] - ]。
Synthesis of intermediate 13 h: 4.99g (10 mmol) of intermediate 13e, 3.78g (10 mmol) of intermediate 13g and 4.2g (20 mmol) of potassium phosphate were weighed into 40ml of NMP. The reaction is carried out for 12 hours at 180 ℃ under the protection of nitrogen and the gas extraction. Cool to room temperature, extract with ethyl acetate/water, dry with anhydrous sodium sulfate, and concentrate by rotary evaporation. The silica gel column separated about 6.18g of intermediate 13h, 72% yield, mass spectrometry molecular weight m/z=858.4 [ m ] + ]。
Synthesis of chemical 166: substituting intermediate 1e in the synthesis of chemical 1 for intermediate 13h, the same reaction conditions can give 1.08g of chemical 166 in 13% yield, mass spectrometry molecular weight m/z=832.4 [ m ] + ]。
Device example:
the following describes the function of the film layer of the organic electroluminescent device according to the preferred embodiment of the present invention.
The organic electroluminescent device according to the present invention comprises an anode layer, a cathode layer, and at least one organic layer between the anode and the cathode. Alternatively, the organic layer is a film layer formed by laminating a plurality of organic compounds. The organic layer may also contain inorganic compounds.
At least one layer of the organic layers of the organic electroluminescent device is a luminescent layer. The organic layer may contain other functional layers in addition to the light-emitting layer, for example, one or more hole injection layers, hole transport layers, or electron blocking layers may be present between the anode layer and the light-emitting layer, it is also possible that an exciton blocking layer or an intermediate layer having a similar function is present between the two light-emitting layers, and one or more hole blocking layers, electron transport layers, or electron injection layers are present between the light-emitting layer and the cathode layer. It should be noted that these functional layers are not necessarily present.
The organic electroluminescent device can be a fluorescent or phosphorescent device or a fluorescent and phosphorescent hybrid device; the light emitting device may be a device having a single light emission, or may be a serial device having a plurality of light emitting units; the vapor deposition processing can be performed, or the solution processing can be performed; either bottom-emitting or top-emitting devices. The light-emitting device may be a single-color light-emitting device, a mixed-color light-emitting device, or a white light-emitting device.
The light emitting layer may include a plurality of guest materials and a plurality of host materials. The guest material may be a fluorescent material, a phosphorescent material, and/or a thermally activated delayed fluorescent material. The host material is a host material that occupies most of the constituent components in the light-emitting layer, and the host material doped and combined with the fluorescent material is referred to as "fluorescent host", and the host material doped and combined with the phosphorescent material is referred to as "phosphorescent host". The choice of host material is not dependent on its molecular structure, but is distinguished by the host material as guest material.
The luminescent layer is a mixture obtained by co-evaporation of a main material and a luminescent material, wherein the doping concentration of the luminescent material is 0.5-20% by weight.
The compounds of the present invention according to the above embodiments may be used in different organic layers. The following organic electroluminescent devices are preferred, the compounds according to the invention being used as luminescent materials for the luminescent layer. The use of the compounds of the present invention of the above embodiments is equally applicable to organic electronic devices.
Such methods are generally known to those of ordinary skill in the art and can be applied to organic electroluminescent devices comprising the compounds of the present invention without undue inventive effort.
The effect of the use of the compounds of the present invention in organic electroluminescent devices is described in detail below by device examples 1 to 13 and device comparative examples 1 to 2, to verify technical progress and advantageous effects of the compounds of the present invention in the art. The examples and comparative examples merely illustrate the invention in further detail, but the invention is not limited by the technical conditions.
Device examples 1 to 13: manufacture of organic electroluminescent device as luminescent material for luminescent layer
A glass substrate having a thickness of 25mm by 75mm by 1.1mm and having an Indium Tin Oxide (ITO) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then Ultraviolet (UV) -ozone cleaned for 30 minutes. The film thickness of ITO was 130nm. The cleaned glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, and vacuum was applied to the substrate holder to 1X 10-5 to 1X 10-6Pa, and a Hole Injection Layer (HIL) HATCN was deposited on the ITO transparent conductive layer to a film thickness of 15nm. A hole transport layer A (HTL) was deposited on the hole injection layer to a film thickness of 60nm. Then, an Electron Blocking Layer (EBL) was deposited on top of the hole transport layer A, with a film thickness of 5nm. Then, an electron blocking layer (EML) was co-deposited on the electron blocking layer to a film thickness of 20nm. The light-emitting layer (EML) was vapor-deposited with a light-emitting material BD and a host material BH of the light-emitting layer by means of multi-source co-vapor deposition, wherein the doping concentration of the light-emitting material was 2 wt%. In order to ensure the accuracy of the doping concentration of the luminescent material, the shielding partition plate is opened after the evaporation rates of the luminescent material and the main material are stable, and the multisource co-evaporation is performed. Then, a Hole Blocking Layer (HBL) was deposited on the light-emitting layer to a film thickness of 5nm. Then, an electron transport material (ETL) and lithium 8-hydroxyquinoline (Liq) were vapor deposited on the hole blocking layer, with a film thickness of 30nm and a doping ratio of 1:1. Then, an electron injection Electrode (EIL) Liq was deposited on the ETL to have a film thickness of 1nm. Then, metal cathode aluminum (Al) was deposited on the EIL to have a film thickness of 100nm. The structure of the organic electroluminescent device of example 1 is shown in fig. 1, and fig. 1 also shows the stacking sequence and effect of each functional layer. The molecular structure of the materials for the OLED is shown in table 1.
Table 1 materials for OLED
The device structure of device example 1 is specifically: ITO (130)/HATCN (15)/HTL (60)/EBL (5)/BH: 1 (20, wt% 2)/HBL (5)/ETL: liq (30, wt% 50)/Liq (1)/Al (100), wherein the numbers in brackets indicate film thickness (units: nm).
Device examples 2 to 13 differ from device example 1 only in that the inventive compound 1 used in the light-emitting layer was replaced with another inventive compound, as shown in table 2 in detail.
Comparative examples 1 to 2 are different from device example 1 in that the light-emitting materials in the organic electroluminescent devices were changed to comparative compounds-1 to comparative compound-2, and the obtained device performance test data are shown in table 2.
The OLED was characterized by standard methods. For this purpose, the electroluminescence spectrum, the external quantum efficiency (EQE, measured in%) is determined, which is calculated as a function of the luminescence density from the current/voltage/luminescence density characteristic line (IUL characteristic line) exhibiting lambertian emission characteristics. At 10mA/cm 2 The required voltage V10 is determined at the current density of (c). Finally, EQE is shown at 10mA/cm 2 Is the external quantum efficiency at a current density of T95 represents the device at 10mA/cm 2 The operating time for the device brightness to decrease to 95% at a current density of (c) is the device at 10mA/cm in CIE coordinates 2 CIE1931 chromaticity coordinates (x, y) calculated by electroluminescence spectroscopy at the current density of (c). Half width of peak is 10mA/cm for device 2 Is a width of half peak height position of the electroluminescent spectrum at current density.
Table 2 device performance list
As can be seen from table 2, the device EQE efficiencies of comparative compound-1 and comparative compound-2 were 7.5% and 7.9%, respectively, mainly due to the lower luminescence quantum efficiency (PLQY) of the luminescent molecules and intermolecular aggregation; meanwhile, the aggregation effect can also accelerate the aging of the device and reduce the service life of the device (ACS appl. Mater. Interfaces 2018,10,30022-30028), so that the T95 service lives of two comparison compounds are shorter. After the molecules of the invention are used as the doping agent of the light-emitting layer, the performance, especially the efficiency and the service life of the electroluminescent device are obviously improved, for example, the EQE efficiency of the device example 9 manufactured by the application 82 can reach 11.2%, which is improved by 49.3% compared with the comparative example 1, and the EQE efficiency of the device example 2 is improved by 41.7%. In the device example 6 manufactured by the application 73, the service life of the T95 can reach 69h, and compared with the device example 1, the service life of the device example 6 is improved by 47%, and the service life of the device example 2 is improved by 60%. And simultaneously, the color purity is improved due to the reduction of the half width of spectrum (FWHM). And the device with the narrow half-peak width spectrum can improve the light extraction efficiency in the top emission device, and is beneficial to further improving the performance of the corresponding top emission device.
Photophysical data
Using a spectrofluorometer manufactured by Nirishi New technology Co., ltd, to measure molecules of comparative compound-1, comparative compound-2, chemical compound 1, chemical compound 6 and other synthetic examples, and evaporating a luminescent material and BH on a quartz plate to form a film with a thickness of 100nm, wherein the doping concentration of the luminescent material is 2 wt%; the film sample containing the quartz plate was irradiated with excitation light of 360nm at room temperature (300 [ K ]), and the fluorescence spectrum was measured, and half-width was obtained as shown in Table 3. The luminescence quantum efficiency (PLQY) of the sample was then measured using an absolute PL quantum yield measurement device manufactured by Binthong photonics, inc.
TABLE 3 photophysical Properties
| Sample of | Half-width (nm) | PLQY(％) |
| Comparison ofCompound-1 | 27.4 | 79 |
| Comparative Compound-2 | 26.8 | 84 |
| Chemical formula 1 | 22.0 | 97 |
| Chemical conversion 6 | 22.2 | 94 |
| Chemical 17 | 19.4 | 95 |
| Chemical conversion 18 | 19.2 | 96 |
| Chemical treatment 46 | 19.6 | 95 |
| Chemical 73 | 20.1 | 96 |
| Chemical conversion 74 | 21.0 | 97 |
| Chemical treatment 77 | 20.6 | 97 |
| Chemical 82 | 20.8 | 97 |
| Chemical 102 | 20.2 | 96 |
| Chemical conversion 143 | 21.7 | 95 |
| Chemical 166 | 22.9 | 93 |
| Chemical conversion 185 | 22.4 | 97 |
Table 3 shows that the fluorescence emission efficiency (PLQY) of the thin film doped with BH at 2% of comparative compound-1 is 79%; the half-peak width of the fluorescence spectrum is 27.4nm, so that the device has low color purity and low device efficiency.
The fluorescence half-width of the 2% BH-doped film of comparative compound-2 was 26.8nm. The luminous efficiency (PLQY) is 84%, so that the color purity and efficiency of the device are improved to a certain extent, but the device is still lower.
The half-peak width of the thin film doped with BH of 2% of the compound is less than or equal to 23nm, which is obviously smaller than that of a comparative compound, and is favorable for obtaining high color purity of a device spectrum; meanwhile, PLQY of the doped film of the compound is more than or equal to 93%, and the high luminous efficiency can obviously improve the efficiency of the device. The improvement of luminous efficiency and the reduction of half-peak width are mainly beneficial to inhibiting non-radiative decay of molecules by the rigid plane structure constructed by the invention, and meanwhile, the steric hindrance effect of quaternary carbon atom substituent groups can effectively inhibit aggregation quenching effect among molecules.
Claims (10)
1. A condensed heterocyclic compound characterized by being represented by the following general formula (1):
wherein Y represents NR 21 An O atom, an S atom, and a Se atom;
R 1 ～R 12 each independently selected from: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, substituted or unsubstituted cyclic cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, and substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms;
R 1 ～R 12 Optionally can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring;
R 13 、R 14 each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted silicon group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atomsSubstituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 40 ring-forming carbon atoms;
R 13 and R is 14 Optionally bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring;
R 21 selected from: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms;
R 21 Optionally may bond with adjacent groups to form substituted or unsubstituted saturated or unsaturated rings;
provided that the compound is not a molecule of the following:
2. the fused heterocyclic compound according to claim 1, wherein Y is NR 21 。
3. The fused heterocyclic compound according to claim 1, wherein R 1 ～R 14 Each independently selected from: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted 2-methylbutyl, substituted or unsubstituted n-pentyl, substituted or unsubstituted sec-pentyl, substituted or unsubstituted trifluoromethyl, substituted or unsubstituted pentafluoroethyl, substituted or unsubstitutedSubstituted 2, 2-trifluoroethyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, substituted or unsubstituted n-butenyl, substituted or unsubstituted isobutenyl, substituted or unsubstituted n-pentenyl, substituted or unsubstituted isopentenyl, substituted or unsubstituted neopentenyl, substituted or unsubstituted ethynyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or substituted methylsilyl, substituted or unsubstituted phenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted indenofluorenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted perylene A group, a substituted or unsubstituted naphthacene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzothiazyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzoselenophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted triphenylphosphine oxide group, a substituted or unsubstituted benzonitrile group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group;
R 1 ～R 12 the substituent groups can also be selected from any one or more of the following groups: hydrogen atom, deuterium atom, fluorine atom, chlorine atom, bromine atom.
4. The fused heterocyclic compound according to claim 1, wherein theThe R is 13 And R is 14 Are bonded to each other to form a ring represented by the following formulas (2-1) to (2-7):
wherein R is 31 ～R 39 The substituent groups are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted silicon group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted 1-valent heterocyclic group having 5 to 50 ring-forming carbon atoms.
5. The fused heterocyclic compound according to claim 1, wherein R 13 And R is 14 Independently selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.
6. The fused heterocyclic compound according to claim 1, wherein R 13 And R is 14 Are bonded to each other to form a substituted or unsubstituted cyclobutane having 4 to 50 carbon atoms, a substituted or unsubstituted cyclopentane having 5 to 50 carbon atoms, a substituted or unsubstituted cyclohexane having 6 to 50 carbon atoms, or adamantane.
7. The fused heterocyclic compound according to claim 1, wherein the fused heterocyclic compound is selected from the following structures:
8. an organic electroluminescent device comprising an anode, a cathode, and at least one organic thin film between the anode and the cathode, wherein the organic thin film comprises the compound according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic thin film comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an exciton blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at least one of the light emitting layers contains the compound according to any one of claims 1 to 7.
10. The organic electroluminescent device according to claim 8 or 9, characterized in that the compound is used as a fluorescent material of a light emitting layer in the organic electroluminescent device.
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