CN117202690A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN117202690A CN117202690A CN202311108347.3A CN202311108347A CN117202690A CN 117202690 A CN117202690 A CN 117202690A CN 202311108347 A CN202311108347 A CN 202311108347A CN 117202690 A CN117202690 A CN 117202690A
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- 239000010410 layer Substances 0.000 claims abstract description 610
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 230000005540 biological transmission Effects 0.000 claims abstract description 55
- 230000005525 hole transport Effects 0.000 claims description 212
- 239000000126 substance Substances 0.000 claims description 105
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 229910052805 deuterium Inorganic materials 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 239000002356 single layer Substances 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000001931 aliphatic group Chemical group 0.000 claims description 26
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 17
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 16
- 125000004431 deuterium atom Chemical group 0.000 claims description 13
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 abstract description 24
- 239000002346 layers by function Substances 0.000 abstract description 6
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 73
- 238000003786 synthesis reaction Methods 0.000 description 73
- -1 triethylsilyl Chemical group 0.000 description 73
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 238000002347 injection Methods 0.000 description 68
- 239000007924 injection Substances 0.000 description 68
- 238000002360 preparation method Methods 0.000 description 64
- 238000000034 method Methods 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 238000004519 manufacturing process Methods 0.000 description 45
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 36
- 150000001975 deuterium Chemical group 0.000 description 34
- 238000001819 mass spectrum Methods 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 238000004128 high performance liquid chromatography Methods 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- 239000000463 material Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 239000011521 glass Substances 0.000 description 18
- 239000000758 substrate Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 10
- 238000007738 vacuum evaporation Methods 0.000 description 10
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 9
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 125000004193 piperazinyl group Chemical group 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 229910052722 tritium Inorganic materials 0.000 description 6
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane 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-K 0.000 description 5
- 239000011247 coating layer Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 125000001624 naphthyl 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
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 229910052790 beryllium Inorganic materials 0.000 description 3
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 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 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 3
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- 238000007740 vapor deposition Methods 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-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
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 241000809861 Xerocomus bubalinus Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
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- 239000000460 chlorine Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
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- 238000007641 inkjet printing Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 239000011368 organic material Substances 0.000 description 2
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- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
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- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
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- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000007979 thiazole derivatives Chemical class 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 description 1
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Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescent device. The hole transmission area of the organic electroluminescent device provided by the invention comprises more than one hole transmission layer (one layer, two layers or three layers) and a light-emitting auxiliary layer, wherein the hole transmission layer contains a compound shown in a formula (I), the light-emitting auxiliary layer contains a compound shown in a formula (II), when the hole transmission layer contains a plurality of layers (two layers or three layers), the compound of each hole transmission layer is different, the device can have proper hole transmission capability and exciton blocking capability by adopting the hole transmission area with the layer structure, and all organic functional layers can be well matched, so that the performances such as driving voltage, luminous efficiency and service life are well improved.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescent device.
Background
An Organic Light-Emitting Diode (OLED) has the characteristics of Light and thin body, wide viewing angle, fast response speed, wide use temperature range, low energy consumption, high efficiency, good color purity, high definition, good flexibility, and the like, and has been widely used in the fields of illumination and display, and is considered as one of the display and illumination technologies with the most development prospects in the industry.
The classical OLED device is in a sandwich structure, a luminescent layer is sandwiched between two electrodes of a cathode and an anode, wherein the luminescent layer contains luminescent substances (guest materials), a certain working voltage is applied between the two electrodes, so that holes and electrons are respectively injected from the anode and the cathode and then reach the luminescent layer, excitons are generated by recombination, energy is released, the excitons migrate under the action of an electric field, energy is transferred to the luminescent substances, electrons in molecules of the luminescent substances migrate from a ground state to an excited state, and the electrons migrate from the excited state to the ground state again due to unstable excited states, thereby releasing the energy in the form of light and generating a luminescence phenomenon. In order to improve the driving voltage, luminous efficiency, color purity, definition, and service life of the device, a hole transport region is generally disposed between the anode and the light emitting layer, and an electron transport region is disposed between the cathode and the light emitting layer. The hole transport region mainly plays a role in injecting and transporting holes and can comprise more than one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, an electron blocking layer and the like; the electron transport region mainly plays a role in injecting and transporting electrons, and may include one or more of an electron injection layer, an electron transport layer, a hole blocking layer, and the like. Meanwhile, the organic layers in the two charge transmission areas and the organic layers with other functions (such as a luminescent layer) are required to have good energy level matching, so that excitons are prevented from diffusing to the edge of the luminescent layer, and effective luminescence in the luminescent layer with high ratio is maintained, thus not only improving the luminous efficiency of the device, but also avoiding rapid aging of organic materials because of reducing the heat generated by interface luminescence, and further prolonging the service life of the device. In addition to the organic functional layer between the anode and the cathode, a coating layer having a high refractive index and high light transmittance is provided on the outer side of the light-emitting side electrode (for example, the outer side of the cathode of the top-emission device), thereby improving the light-emitting efficiency and color purity of the device.
At present, most of OLED devices used in industry have a defect of mismatch of hole and electron transmission rates, which results in degradation of performance such as driving voltage, luminous efficiency and service life of the device, so OLED workers are required to continuously optimize and innovate materials selected for OLED and OLED device structure.
Disclosure of Invention
In order to solve the technical problems, the invention provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is arranged between the anode and the cathode, the organic layer comprises a hole transmission area, a luminescent layer and an electron transmission area, the hole transmission area comprises a first hole transmission layer and a luminescent auxiliary layer, the first hole transmission layer is arranged between the anode and the luminescent layer, the luminescent auxiliary layer is arranged between the first hole transmission layer and the luminescent layer, the first hole transmission layer contains one of compounds shown in a formula (I), the luminescent auxiliary layer contains one of compounds shown in a formula (II), the organic functional layers formed by the two materials can well match the transmission rates of holes and electrons, meanwhile, the energy level matching degree between the functional layers is also high, the driving voltage of the device can be effectively reduced, the luminescent efficiency of the device can be improved, and the service life of the device can be prolonged.
In formula (I), the Ar 1 、Ar 2 Independently selected from one of the structures shown below:
wherein, a is as follows 1 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 1 Each occurrence is identically or differently selected from 0, 1, 2 or 3; the said c 1 At each occurrenceSelected identically or differently from 0, 1, 2, 3, 4 or 5;
said R is 1 、R 2 Independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or substituted C1 to C12 alkyl group;
said R is 3 Each occurrence is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 alicyclic ring, and two adjacent R 3 Can be linked to form one of a substituted or unsubstituted C3-C7 aliphatic ring and a substituted or unsubstituted C6-C10 aromatic ring;
ar as described 3 One selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
The L is 1 ~L 3 Independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30, and divalent group formed by fusing substituted or unsubstituted aromatic ring of C6-C30 and aliphatic ring of C3-C7;
in formula (II), said a 101 Selected from 0, 1, 2 or 3;
said R is 101 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, and a group in which a substituted or unsubstituted C6-C30 aromatic ring is condensed with a C3-C7 aliphatic ring;
ar as described 101 ~Ar 106 Independently selected from one of the structures shown below:
wherein, a is as follows 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said c 102 Each occurrence is identically or differently selected from 0, 1, 2 or 3; d is as follows 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6;
said R is 102 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
said R is 103 Each occurrence of which is identically or differently selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C12 alkyl group;
the L is 101 ~L 106 Independently selected from a single bond or one of the structures shown below:
wherein, a is as follows 103 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 103 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said c 103 Each occurrence is identically or differently selected from 0, 1 or 2; d is as follows 103 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6;
said R is 104 Each occurrence of which is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted One of silyl group, phenyl group substituted with deuterium atom or unsubstituted;
said R is 105 And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, identically or differently at each occurrence.
The beneficial effects are that:
the hole transmission area of the organic electroluminescent device provided by the invention comprises more than one hole transmission layer (one layer, two layers or three layers) and a light-emitting auxiliary layer, wherein the hole transmission layer contains a compound shown in a formula (I), the light-emitting auxiliary layer contains a compound shown in a formula (II), when the hole transmission layer contains a plurality of layers (two layers or three layers), the compound of each hole transmission layer is different, the device can have proper hole transmission capability and exciton blocking capability by adopting the hole transmission area with the layer structure, and all organic functional layers can be well matched, so that the performances such as driving voltage, luminous efficiency and service life are well improved.
Detailed Description
The following description of the embodiments of the present invention will be made more complete and obvious by the following description of the embodiments of the present invention, wherein the embodiments are described in some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance. Taking hydrogen as an example, each hydrogen atom of all naturally occurring compounds contains about 0.0156 atomic% deuterium.
In the present invention, the use of "H" and "hydrogen atom" means that the hydrogen atom in the chemical structure contains no more than the natural abundance of deuterium or tritium atoms, for example, no more than 0.0156 atomic% deuterium. "D" and "deuterium atom" refer to any value having an abundance of deuterium content above natural abundance, e.g., above 0.1 atom%, above 1 atom%, above 10 atom%, e.g., where about 95 atom% is deuterium. "T" and "tritium atom" refer to any value where the abundance of tritium content is above natural abundance, e.g., greater than 0.1 atomic%, greater than 1 atomic%, greater than 10 atomic%, e.g., where about 95% is tritium. In the present invention, hydrogen not shown is omitted to indicate "H" or "hydrogen atom".
The halogen atom in the present invention means fluorine atom, chlorine atom, bromine atom and iodine atom.
As used herein, "silyl" refers to-SiH 3 A group, the "substituted or unsubstituted silyl" refers to one or more H on the silyl group being substituted or unsubstituted with a substituent. The "substituted or unsubstituted silyl group" may be represented by-Si (R k ) 3 A representation, wherein each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substitutedOr unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferred substituted silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like. The above-mentioned substituted silyl group is preferably a trimethylsilyl group, a triethylsilyl group, a triphenylsilyl group, a diphenylmethylsilyl group, a phenyldimethylsilyl group, a diphenylmethylsilyl group, or a phenyldimethylsilyl group.
The alkyl group according to the present invention is a hydrocarbon group having at least one hydrogen atom in the alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, or an n-hexyl group.
Cycloalkyl according to the invention is a hydrocarbon radical formed by the removal of at least one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms. Examples may include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, and the like. The cycloalkyl group is preferably a cyclopentylalkyl group, a cyclohexenyl group, a 1-adamantyl group, a 2-adamantyl group, or a norbornyl group.
Cycloalkenyl according to the invention means hydrocarbon radicals formed by the removal of at least one hydrogen atom from the cycloolefin molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms. Examples may include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. The cycloalkyl group is preferably a cyclopentenyl group or a cyclohexenyl group.
The heterocycloalkyl group according to the present invention is a group formed by dropping at least one hydrogen atom from a heterocyclic molecule having at least one heteroatom other than carbon atoms, and the heteroatom includes a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a selenium atom, a phosphorus atom, and the like, and is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. Preferably from 1 to 3 heteroatoms, more preferably from 1 to 2 heteroatoms, particularly preferably 1 heteroatom. Preferably from 3 to 15, more preferably from 3 to 12, particularly preferably from 5 to 6, ring atoms. Examples may include, but are not limited to, oxiranyl, ethylidenyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, and the like. The heterocyclic group is preferably a tetrahydropyrrolyl group, a piperidyl group, a morpholinyl group, a thiomorpholinyl group, or a piperazinyl group.
Aryl in the present invention means that after one hydrogen atom is removed from the aromatic nucleus carbon of the aromatic compound molecule, a monovalent group is left, which may be a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group, or a condensed group of an aryl group and an alicyclic ring, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but is not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, for example, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthryl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, and the like, but is not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.
Heteroaryl according to the present invention refers to the generic term for groups in which one or more aromatic nucleus carbon atoms in the aryl group are replaced by heteroatoms, including but not limited to oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, most preferably 3 to 12 carbon atoms, the attachment site of the heteroaryl group may be located on a ring-forming carbon atom, or on a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl, and the like; the polycyclic heteroaryl group includes bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, and the like. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a benzodibenzothienyl group, a benzodibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.
The group formed by fusing the aromatic ring and the aliphatic ring refers to the general name that after the aromatic ring and the aliphatic ring (cycloalkyl, cycloalkenyl and cycloalkynyl) are fused together, one hydrogen atom is removed, and a monovalent group is left. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, which may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto; the alicyclic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, which may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexayne, cycloheptyne. Preferably, examples of the group in which the aromatic ring is condensed with the aliphatic ring may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like.
Arylene in the context of the present invention means an aryl group having two bonding sites, i.e., a divalent group. With respect to the description of aryl groups that may be applied, provided above, the difference is that arylene groups are divalent groups.
Heteroaryl, as used herein, means a heteroaryl group having two bonding sites, i.e., a divalent group. With respect to the description of heteroaryl groups that may be applied, provided above, the difference is that the heteroarylene group is a divalent group.
The divalent group formed by fusing an aromatic ring and an aliphatic ring in the present invention refers to a group formed by fusing an aromatic ring and an aliphatic ring having two bonding sites, that is, a divalent group. Regarding the description thereof, which can be applied to the group formed by fusing an aromatic ring and an aliphatic ring provided above, the difference is that a divalent group formed by fusing an aromatic ring and an aliphatic ring is a divalent group.
"substitution" as used herein means that a hydrogen atom in some of the functional groups is replaced with another atom or functional group (i.e., substituent), and the position of substitution is not limited as long as the position is one where a hydrogen atom is substituted, and when two or more are substituted, two or more substituents may be the same or different from each other.
The term "substituted or unsubstituted" as used herein means that it is not substituted or substituted with one or more substituents selected from the group consisting of: deuterium atom, halogen atom, amino group, cyano group, nitro group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted silyl group, preferably deuterium atom, halogen atom, cyano group, nitro group, C1-C12 alkyl group, C3-C12 cycloalkyl group, C3-C12 cycloalkenyl group, C3-C12 heterocycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, substituted or unsubstituted silyl group, in the case of being substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other; preferably, it means not substituted or substituted with one or more substituents selected from the group consisting of: deuterium atoms, fluorine atoms, cyano groups, methyl groups, trifluoromethyl groups, deuteromethyl groups, ethyl groups, deuteroethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, sec-butyl groups, tert-butyl groups, deuterated tert-butyl groups, n-pentyl groups, n-hexyl groups, cyclopropane groups, methyl-substituted cyclopropane groups, ethyl-substituted cyclopropane groups, deuterated cyclopropane groups, cyclobutane groups, methyl-substituted cyclobutane groups, ethyl-substituted cyclobutane groups, deuterated cyclobutane groups, cyclopentane groups, methyl-substituted cyclopentane groups, ethyl-substituted cyclopentane groups, deuterated cyclopentane groups, cyclohexane groups, methyl-substituted cyclohexane groups, ethyl-substituted cyclohexane groups, n-propyl-substituted cyclohexane groups, n-butyl-substituted cyclohexane groups, deuterated cyclohexane groups, cycloheptane groups, cyclopentene groups, methyl-substituted cyclopentene groups ethyl substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl substituted adamantyl, ethyl substituted adamantyl, deuterated adamantyl, norbornyl, methyl substituted norbornyl, ethyl substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl substituted piperazinyl, ethyl substituted piperazinyl, phenyl substituted piperazinyl, naphthyl substituted piperazinyl, phenyl, deuterophenyl, naphthyl, deuteroalkenyl, anthracenyl, deuteroalkanyl, phenanthryl, deuterophenyl, triphenylenyl, pyrenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, triphenylsilyl, where substituted with multiple substituents, the multiple substituents may be the same or different from each other.
In this specification, when the position of a substituent or attachment site on a ring is not fixed, it means that it can be attached to any of the optional sites of the ring. For example, the number of the cells to be processed,can indicate-> Can indicate-> Can represent And so on.
In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For example, the number of the cells to be processed,can indicate-> Can indicate-> Can indicate->And so on.
The linking to form a ring structure (e.g., to form a saturated or unsaturated C3-C10 carbocycle, to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocycle) as described herein means that the individual groups are linked to each other by chemical bonds and optionally form double/triple bonds, and may constitute aromatic groups, as exemplified below:
in the present invention, the ring formed by the connection may be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of both, and the ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentaacene, cyclohexene, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
In the present specification, "at least one" includes one, two, three, four, five, six, seven, eight, or more.
A layer described herein as being "on" another layer or electrode may be construed as directly on the other layer or electrode, or may have other layer structures in between.
A layer described herein as being "between" two layers, two electrodes, or one layer and an electrode may be interpreted as the only layer structure between the two, or one or more layer structures may exist between the two.
The invention provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises a hole transmission area, a luminescent layer and an electron transmission area, the hole transmission area comprises a first hole transmission layer and a luminescent auxiliary layer, the first hole transmission layer is positioned between the anode and the luminescent layer, the luminescent auxiliary layer is positioned between the first hole transmission layer and the luminescent layer, the first hole transmission layer contains one of compounds shown in a formula (I), and the luminescent auxiliary layer contains one of compounds shown in a formula (II):
In formula (I), the Ar 1 、Ar 2 Independently selected from one of the structures shown below:
wherein, a is as follows 1 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 1 Each occurrence is identically or differently selected from 0, 1, 2 or 3; the said c 1 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5;
said R is 1 、R 2 Independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or substituted C1 to C12 alkyl group;
said R is 3 Each occurrence is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 alicyclic ring, and two adjacent R 3 Can be linked to form one of a substituted or unsubstituted C3-C7 aliphatic ring and a substituted or unsubstituted C6-C10 aromatic ring;
ar as described 3 One selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
The L is 1 ~L 3 Independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30, and divalent group formed by fusing substituted or unsubstituted aromatic ring of C6-C30 and aliphatic ring of C3-C7;
in formula (II), said a 101 Selected from 0, 1, 2 or 3;
said R is 101 And is selected, identically or differently, for each occurrence, from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aromatic ringOne of the groups formed by fusing the aliphatic rings;
ar as described 101 ~Ar 106 Independently selected from one of the structures shown below:
wherein, a is as follows 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said c 102 Each occurrence is identically or differently selected from 0, 1, 2 or 3; d is as follows 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6;
said R is 102 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
said R is 103 Each occurrence of which is identically or differently selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C12 alkyl group;
the L is 101 ~L 106 Independently selected from a single bond or one of the structures shown below:
wherein, a is as follows 103 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 103 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said c 103 Each occurrence is identically or differently selected from 0, 1 or 2; d is as follows 103 Each occurrence ofWhen the two are selected from 0, 1, 2, 3, 4, 5 or 6 identically or differently;
said R is 104 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, and a phenyl group substituted or unsubstituted by a deuterium atom;
Said R is 105 And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, identically or differently at each occurrence.
Preferably, said R 1 、R 2 And is selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, n-pentyl and n-hexyl.
Preferably, said R 3 And is selected from, identically or differently, one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a deuterated tert-butyl group, an n-pentyl group, an n-hexyl group, an adamantyl group, a norbornyl group, a trimethylsilyl group, a triphenylsilyl group, a phenyl group, a deuterated phenyl group.
Preferably, said Ar 1 、Ar 2 Independently selected from one of the structures shown below:
wherein, a is as follows 31 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 31 Each occurrence is identically or differently selected from 0, 1, 2 or 3; the said c 31 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; d is as follows 31 Each occurrence is identically or differently selected from 0, 1 or 2;
said R is 31 At each time of occurrence of this, the process is completed,the two groups are the same or different and are selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, deuterated tert-butyl group, n-pentyl group, n-hexyl group, adamantyl group, norbornyl group, trimethylsilyl group, triphenylsilyl group, phenyl group and deuterated phenyl group.
Preferably, said Ar 1 、Ar 2 Independently selected from one of the structures shown below:
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preferably, said Ar 3 One selected from the following structures:
wherein, a is as follows 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 3 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; the said c 3 Each occurrence is identically or differently selected from 0, 1, 2 or 3; d is as follows 3 Each occurrence is identically or differently selected from 0, 1 or 2; said e 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
said R is 6 Each occurrence of which is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6One of the groups formed by fusing an aromatic ring of C30 and an aliphatic ring of C3-C7;
said R is 7 And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, identically or differently at each occurrence.
Preferably, said R 6 And is selected from, identically or differently, one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a deuterated tert-butyl group, an n-pentyl group, an n-hexyl group, an adamantyl group, a norbornyl group, a trimethylsilyl group, a triphenylsilyl group, a phenyl group, a deuterated phenyl group.
Preferably, said R 7 And is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group and deuterated tert-butyl group.
Preferably, said Ar 3 One selected from the following structures:
preferably, said L 1 ~L 3 Independently selected from a single bond or one of the structures shown below:
wherein, a is as follows 2 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 2 Each occurrence is identically or differently selected from 0, 1, 2 or 3; the said c 2 Each timeWhen present, are identically or differently selected from 0, 1 or 2; d is as follows 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
said R is 4 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
said R is 5 And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, identically or differently at each occurrence.
Preferably, said R 4 And is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, deuterated tert-butyl group, trimethylsilyl group, phenyl group, deuterated phenyl group.
Preferably, said R 5 And is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group and deuterated tert-butyl group.
Preferably, said L 1 ~L 3 Independently selected from a single bond or one of the structures shown below:
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preferablySaid R is 102 And is selected from, identically or differently, one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a deuterated tert-butyl group, an n-pentyl group, an n-hexyl group, an adamantyl group, a norbornyl group, a trimethylsilyl group, a triphenylsilyl group, a phenyl group, a deuterated phenyl group.
Preferably, said R 103 And is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group and deuterated tert-butyl group.
Preferably, said Ar 101 ~Ar 106 Independently selected from one of the structures shown below:
preferably, said R 104 And is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, deuterated tert-butyl group, trimethylsilyl group, phenyl group, deuterated phenyl group.
Preferably, said R 105 And is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group and deuterated tert-butyl group.
Preferably, said L 101 ~L 106 Independently selected from a single bond or one of the structures shown below:
preferably, the compound shown in the formula (I) is selected from one of the compounds shown in the following formulas (I-A) to (I-F):
wherein Ar is as described 3 、L 1 ~L 3 、a 1 、b 1 、c 1 、R 1 、R 2 、R 3 All as described herein.
Preferably, the compound shown in the formula (I) is selected from one of the following compounds:
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preferably, the compound shown in the formula (II) is selected from one of the compounds shown in the following formulas (II-A) to (II-D):
Wherein Ar is as described 101 ~Ar 106 、L 101 ~L 106 All as described herein;
said R is 201 Each occurrence of the compound is identically selected from one of deuterium atom, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl and deuterated tert-butyl.
Preferably, the compound shown in the formula (II) is selected from one of the following compounds:
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the organic electroluminescent device comprises an anode, a hole transport region above the anode, a luminescent layer above the hole transport region, an electron transport region above the luminescent layer, and a cathode above the electron transport region.
The organic electroluminescent device according to the present invention may further comprise a capping layer over the cathode.
The anode of the invention can be a reflective anode, such as a reflective film formed by silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb) or alloys thereof, or a transparent or semitransparent layer structure with high work function, such as Indium Tin Oxide (ITO), indium zinc oxide (ZnO), aluminum Zinc Oxide (AZO), indium Gallium Oxide (IGO), indium oxide (In) 2 O 3 ) Or tin oxide (SnO) 2 ) The layer structure is formed according to the type of the device to be manufactured, if the device to be manufactured is a bottom emission device (anode side emits light), a transparent or semitransparent anode is required to be manufactured, and if the device to be manufactured is a top emission device (cathode side emits light), a reflecting anode is required to be manufactured.
The hole transport region comprises more than one organic functional layer of a hole injection layer, a hole transport layer and a light-emitting auxiliary layer.
The hole injection layer of the present invention may have a single-layer structure formed of a single material, or may have a single-layer structure or a multi-layer structure formed of different materials. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and derivatives thereof, phthalocyanine derivatives, axylene compounds, and other substances having high hole injection properties, for example, 4',4″ -tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazabenzophenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5, 6-tetrafluoro-7, 7', 8' -tetracyanodimethylbenzoquinone (F4-TCNQ), poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT/PSS), compounds HT-1 to HT-11, compounds p-1 to p-3, and compounds represented by the formula (I) of the present invention may be used, but are not limited thereto.
Preferably, the hole injection layer has a single layer structure of a single substance, and the substance may be 2 to TNATA, HATCN, cuPC.
Preferably, the hole injection layer has a single-layer structure composed of different substances. More preferably, the hole injection layer has a single-layer structure composed of two substances, one is a triarylamine compound, for example, compounds HT-1 to HT-11, a compound represented by formula (I) of the present invention, and the other is an axylene compound or other substance having high hole injection properties, for example, HATCN, F4-TCNQ, and compounds p-1 to p-3.
The hole transport layer of the present invention may have a single layer structure of a single material, or may have a single layer structure or a multilayer structure of different materials. Triarylamine compounds can be used, as can other hole mobilities at 10 -6 cm 2 Examples of the substances above/Vs include, but are not limited to, N, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 4' -tris (N, N-diphenylamino) triphenylamine (TDATA), the above-mentioned compounds HT-1 to HT-11, and the compounds represented by the formula (I) of the present invention.
Preferably, the hole transport layer has a single layer structure formed of a single substance, and the substance is a compound represented by formula (I).
Preferably, the hole transport layer has a single layer structure formed of different substances, wherein the different substances are selected from the compounds shown in the formula (I), and each substance is a different compound. More preferably, the hole transport layer has a single layer structure formed of two substances, wherein the two substances are selected from the compounds shown in the formula (I), and the two substances are different compounds.
Preferably, the hole transport layer is a multi-layer structure formed by different substances, wherein the different substances are selected from compounds shown in a formula (I), and each substance is a different compound. More preferably, the hole transport layer is a bilayer structure formed of two substances, wherein the two substances are selected from the compounds shown in formula (I), and the two substances are different compounds. Further preferably, the hole transport layer is a bilayer structure formed of two substances, wherein the two substances are selected from the compounds shown in formula (I), and the two substances are different compounds, and each layer structure contains only one substance.
The light-emitting auxiliary layer of the present invention may have a single-layer structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives and dibenzofuran derivatives may be used, and other materials having appropriate HOMO and T1 energy levels may be used, and TPD, NPB, N, 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-di ([ 1,1' -biphenyl ] -4-yl) -3'- (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, the compounds HT-1 to HT-11 as shown above, the compounds of formula (II) of the present invention, but are not limited thereto.
Preferably, the light-emitting auxiliary layer has a single layer structure formed of a single substance, and the substance is a compound represented by formula (II).
Preferably, the light-emitting auxiliary layer has a single-layer structure formed by different substances, wherein the different substances are selected from compounds shown in a formula (II), and each substance is a different compound. More preferably, the light-emitting auxiliary layer has a single layer structure formed of two substances, wherein the two substances are selected from the compounds shown in the formula (II), and the two substances are different compounds.
Preferably, the light-emitting auxiliary layer is a multi-layer structure formed by different substances, wherein the different substances are selected from compounds shown in a formula (II), and each substance is a different compound. More preferably, the light-emitting auxiliary layer has a double-layer structure formed of two substances, wherein the two substances are selected from the compounds shown in the formula (II), and the two substances are different compounds. Further preferably, the light-emitting auxiliary layer is a double-layer structure composed of two substances, wherein the two substances are selected from the compounds shown in the formula (II), the two substances are different compounds, and each layer structure contains only one substance.
Preferably, the hole transport region includes a hole transport layer (first hole transport layer) and a light emitting auxiliary layer: the first hole transport layer is positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer is positioned between the first hole transport layer and the light-emitting layer, the first hole transport layer is of a single-layer structure formed by a single substance selected from compounds shown in a formula (I), and the light-emitting auxiliary layer is of a single-layer structure formed by a single substance and is a compound shown in a formula (II).
Preferably, the hole transport region includes a hole transport layer (first hole transport layer) and a light emitting auxiliary layer: the first hole transmission layer is positioned between the anode and the light-emitting layer, and the light-emitting auxiliary layer is positioned between the first hole transmission layer and the light-emitting layer. The first hole transport layer is a single layer structure formed by a single substance selected from compounds shown in a formula (I); the light-emitting auxiliary layer is a double-layer structure formed by two substances, wherein the two substances are selected from compounds shown in a formula (II), and the two substances are different compounds.
Preferably, the hole transport region includes two hole transport layers (a first hole transport layer and a second hole transport layer) and a light emitting auxiliary layer: the first hole transport layer is positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer is positioned between the first hole transport layer and the light-emitting layer, and the second hole transport layer is positioned between the first hole transport layer and the light-emitting auxiliary layer. The first hole transport layer is a single layer structure formed by a single substance selected from compounds shown in a formula (I); the second hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer; the light-emitting auxiliary layer has a single layer structure formed by a single substance, and the substance is a compound shown as a formula (II).
Preferably, the hole transport region includes two hole transport layers (a first hole transport layer and a second hole transport layer) and a light emitting auxiliary layer: the first hole transport layer is positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer is positioned between the first hole transport layer and the light-emitting layer, and the second hole transport layer is positioned between the first hole transport layer and the light-emitting auxiliary layer. The first hole transport layer is a single layer structure formed by a single substance selected from compounds shown in a formula (I); the second hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer; the light-emitting auxiliary layer is a double-layer structure formed by two substances, wherein the two substances are selected from compounds shown in a formula (II), and the two substances are different compounds.
Preferably, the hole transport region includes two hole transport layers (a first hole transport layer and a second hole transport layer) and a light emitting auxiliary layer: the first hole transmission layer is positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer is positioned between the first hole transmission layer and the light-emitting layer, and the second hole transmission layer is positioned between the light-emitting auxiliary layer and the light-emitting layer. The first hole transport layer is a single layer structure formed by a single substance selected from compounds shown in a formula (I); the second hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer; the light-emitting auxiliary layer has a single layer structure formed by a single substance, and the substance is a compound shown as a formula (II).
Preferably, the hole transport region includes two hole transport layers (a first hole transport layer and a second hole transport layer) and a light emitting auxiliary layer: the first hole transmission layer is positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer is positioned between the first hole transmission layer and the light-emitting layer, and the second hole transmission layer is positioned between the light-emitting auxiliary layer and the light-emitting layer. The first hole transport layer is a single layer structure formed by a single substance selected from compounds shown in a formula (I); the second hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer; the light-emitting auxiliary layer is a double-layer structure formed by two substances, wherein the two substances are selected from compounds shown in a formula (II), and the two substances are different compounds.
Preferably, the hole transport region includes three layers of hole transport layers (a first hole transport layer, a second hole transport layer, and a third hole transport layer) and a light emitting auxiliary layer: the first hole transmission layer is positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer is positioned between the first hole transmission layer and the light-emitting layer, the second hole transmission layer is positioned between the first hole transmission layer and the light-emitting auxiliary layer, and the third hole transmission layer is positioned between the light-emitting auxiliary layer and the light-emitting layer. The first hole transport layer is a single layer structure formed by a single substance selected from compounds shown in a formula (I); the second hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer; the third hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer and the second hole transport layer; the light-emitting auxiliary layer has a single layer structure formed by a single substance, and the substance is a compound shown as a formula (II).
Preferably, the hole transport region includes three layers of hole transport layers (a first hole transport layer, a second hole transport layer, and a third hole transport layer) and a light emitting auxiliary layer: the first hole transmission layer is positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer is positioned between the first hole transmission layer and the light-emitting layer, the second hole transmission layer is positioned between the first hole transmission layer and the light-emitting auxiliary layer, and the third hole transmission layer is positioned between the light-emitting auxiliary layer and the light-emitting layer. The first hole transport layer is a single layer structure formed by a single substance selected from compounds shown in a formula (I); the second hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer; the third hole transport layer is a single layer structure formed by a single substance, wherein the substance is selected from compounds shown in a formula (I) and is different from the compounds in the first hole transport layer and the second hole transport layer; the light-emitting auxiliary layer is a double-layer structure formed by two substances, wherein the two substances are selected from compounds shown in a formula (II), and the two substances are different compounds.
The light emitting layer according to the present invention includes a guest material and a host material, and a dual host material formed of two host materials may be used. As the guest material, fluorescent compounds such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives and the like can be used, and examples thereof include 10- (2-benzothiazolyl) -2,3,6, 7-tetrahydro-1, 7-tetramethyl-1H, 5H,11H- [1]Benzopyran [6,7,8-ij ]]Quinolizin-11-one (C545T), 4' -bis (9-ethyl-3-carbazolyl vinyl) -1,1' -biphenyl (BCzVBi), 4' -bis [4- (di-p-tolylamino) styryl]Examples of the metal complex such as an iridium complex, an osmium complex, and a platinum complex, which may be used as a phosphorescent light-emitting material, include bis (4, 6-difluorophenylpyridine-N, C2) picolinated iridium (FIrpic) and tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) 2 (acac)) and the like. The host material is preferably a material having higher LUMO and lower HOMO than the guest material, for example, a metal complex such as an aluminum complex or zinc complex, an oxadiazole derivative, a benzoxazole derivative, a heterocyclic compound such as a benzothiazole derivative or a benzimidazole derivative, a condensed aromatic compound such as a carbazole derivative or an anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, and examples thereof include Alq 3 BAlq, TPBI, TPD, 4 '-bis (9-Carbazolyl) Biphenyl (CBP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (2-naphthyl) Anthracene (ADN), but are not limited thereto.
The electron transport region according to the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.
The electron injection layer of the invention can be a single layer structure formed by a single substance, can also be a single layer structure or a multi-layer structure formed by different substances, and can be selected from one or more of the following substances: alkali metal, alkaline earth metal, alkali metal halide, alkaline earth metal halide, alkali metal oxide, alkaline earth metal oxide, alkali metal salt, alkaline earth metal salt, and other substances having high electron injection properties. Examples can be cited as Li, ca, sr, liF, csF, caF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 LiOx, yb, tb, etc., but is not limited thereto.
The electron transporting layer according to the present invention may have a single layer structure, or may have a single layer structure or a multilayer structure of different materials, and aluminum complex, lithium complex, beryllium complex, zinc complex, oxazole derivative, benzoxazole derivative, thiazole derivative, benzothiazole derivative, imidazole derivative, benzimidazole derivative, carbazole derivative, phenanthroline derivative, polymer compound, etc. having high electron transporting property may be used, and examples thereof include 8-hydroxyquinoline aluminum (Alq 3 ) Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq 2 ) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 2- (4-biphenyl) -5-Phenyloxadiazole (PBD), but is not limited thereto.
The hole blocking layer of the present invention may have a single layer structure formed of a single material, or may have a single layer structure or a multilayer structure formed of different materials. The material selected requires a T1 energy level higher than the light emitting layer so that energy loss from the light emitting layer is blocked. In addition, the HOMO energy level of the selected material is lower than that of the main body material of the light-emitting layer, so that the hole blocking effect is realized. Further, the electron mobility of the hole blocking layer material used was 10 -6 cm 2 and/Vs, facilitating electron transport. One or more of the following may be selected: aluminum complex, lithium complex, beryllium complex, oxazole derivative, benzoxazole derivative, thiazole derivative, benzothiazoleDerivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, high molecular compounds, and the like. Examples include, but are not limited to, 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), BAlq, and the like.
The cathode of the invention can be a thin film with low work function, which is made of lithium, calcium, lithium fluoride/aluminum, silver, magnesium silver alloy, etc., and can be made into a reflecting electrode, a transparent electrode or a semitransparent electrode by adjusting the thickness of the film, if a bottom emission device is required to be prepared, a reflecting cathode is required to be prepared, if a top emission device is required to be prepared, and a transparent or semitransparent cathode is required to be prepared.
The cover layer according to the present invention may have a single layer structure of a single substance, or may have a single layer structure or a multilayer structure of different substances. The material for the covering layer may be an organic or inorganic substance having an appropriate refractive index, and may be, for example, a metal halide, oxide, nitride, oxynitride, sulfide, selenide, aromatic hydrocarbon compound, heteroaromatic compound, aromatic amine compound, or the like, and LiF, csF, mgF is exemplified 2 、CaF 2 、CsCl、CuI、V 2 O 5 、WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 、SiN、ZnS、Alq 3 Compound CP-1, compound CP-2, compound CP-3, compound CP-4, but not limited thereto.
Preferably, the structure of the organic electroluminescent device is one of the following device structures:
1) Anode/hole injection layer/first hole transport layer/light emitting auxiliary layer/light emitting layer/electron transport layer/electron injection layer/cathode;
2) Anode/hole injection layer/first hole transport layer/light emitting auxiliary layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode;
3) An anode/a hole injection layer/a first hole transport layer/a second hole transport layer/a light emitting auxiliary layer/a light emitting layer/an electron transport layer/an electron injection layer/a cathode;
4) An anode/a hole injection layer/a first hole transport layer/a second hole transport layer/a light emitting auxiliary layer/a light emitting layer/a hole blocking layer/an electron transport layer/an electron injection layer/a cathode;
5) An anode/a hole injection layer/a first hole transport layer/a light emitting auxiliary layer/a second hole transport layer/a light emitting layer/an electron transport layer/an electron injection layer/a cathode;
6) An anode/a hole injection layer/a first hole transport layer/a light emitting auxiliary layer/a second hole transport layer/a light emitting layer/a hole blocking layer/an electron transport layer/an electron injection layer/a cathode;
7) An anode/a hole injection layer/a first hole transport layer/a second hole transport layer/a light emitting auxiliary layer/a third hole transport layer/a light emitting layer/an electron transport layer/an electron injection layer/a cathode;
8) An anode/a hole injection layer/a first hole transport layer/a second hole transport layer/a light emitting auxiliary layer/a third hole transport layer/a light emitting layer/a hole blocking layer/an electron transport layer/an electron injection layer/a cathode;
9) Anode/hole injection layer/first hole transport layer/light emitting auxiliary layer/light emitting layer/electron transport layer/electron injection layer/cathode/cover layer;
10 Anode/hole injection layer/first hole transport layer/light emitting auxiliary layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
11 Anode/hole injection layer/first hole transport layer/second hole transport layer/light-emitting auxiliary layer/light-emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
12 Anode/hole injection layer/first hole transport layer/second hole transport layer/light-emitting auxiliary layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer;
13 Anode/hole injection layer/first hole transport layer/light emitting auxiliary layer/second hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/capping layer;
14 Anode/hole injection layer/first hole transport layer/light emitting auxiliary layer/second hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/cover layer;
15 Anode/hole injection layer/first hole transport layer/second hole transport layer/light-emitting auxiliary layer/third hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode/cover layer;
16 Anode/hole injection layer/first hole transport layer/second hole transport layer/light-emitting auxiliary layer/third hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer.
The organic layers, the cathode and the anode can be prepared by any one method of vacuum evaporation, ink-jet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing and the like, and the thickness of each layer is not particularly limited, so that good device performance can be obtained. Each of the organic layers described above is preferably prepared using a method of vacuum evaporation, inkjet printing or spin coating. When the vacuum vapor deposition method is used, if the organic layer has a single-layer structure containing a plurality of substances, the organic layer may be formed by vapor deposition of the plurality of substances at a predetermined mass ratio and a predetermined vapor deposition rate ratio.
The thickness of each organic layer is usually 5nm to 100. Mu.m, preferably 10nm to 200nm. The thickness of the anode and cathode is adjusted according to the desired transparency.
The organic electroluminescent device provided by the invention can be applied to the fields of illumination, display and the like, and can be specifically exemplified by a large-size display such as a smart phone display screen, a tablet personal computer display screen, an intelligent wearable device display screen, a television and the like, VR, an automobile tail lamp and the like.
The technical scheme and technical effects of the present invention will be further described below with examples and comparative examples.
The mass spectrum of the compound of the invention uses a G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer of the Wolts company, england, chloroform as a solvent;
the elemental analysis was carried out using a Vario EL cube organic elemental analyzer from Elementar, germany, and the sample mass was 5 to 10mg.
Synthesis example 1: synthesis of Compounds HT1-3
AA-3 (4.66 g,50 mmol), BB-3 (19.87 g,50 mmol), sodium tert-butoxide (9.61 g,100 mmol) and toluene (250 ml) were added to the reaction flask under nitrogen atmosphere, and the mixture was stirred and then Pd (OAc) was added to the reaction system with continued stirring 2 (0.11 g,0.5 mmol) and 0.5M P (t-Bu) 3 Toluene solution (2 ml), the reaction system was heated to reflux, and reacted at reflux for 6 hours. After the completion of the reaction, the mixture was cooled to room temperature, washed with distilled water, extracted with methylene chloride, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure, and the obtained residue was recrystallized from toluene/methanol (volume ratio 6:1) to give compound CC-3 (16.79 g, yield 82%). Mass spectrum m/z:409.1849 (theory: 409.1830).
CC-3 (12.29 g,30 mmol), DD-3 (11.92 g,30 mmol), sodium tert-butoxide (5.77 g,60 mmol) and toluene (150 ml) were added to the flask under nitrogen and Pd was added continuously with stirring 2 (dba) 3 (0.32 g,0.36 mmol) and 0.5M P (t-Bu) 3 Toluene solution (1.5 ml), and was heated under reflux for 7 hours. After the completion of the reaction, the mixture was cooled to room temperature, washed with distilled water, extracted with dichloromethane, the organic phase was dried over anhydrous magnesium sulfate, filtered, the filtrate was distilled under reduced pressure, and the obtained residue was recrystallized from toluene/methanol (volume ratio 9:1) to give compound HT1-3 (17.42 g, yield 80%). The purity of the solid detected by HPLC is not less than 99.98%. Mass spectrum m/z:725.3066 (theory: 725.3083). Theoretical element content (%) C 56 H 39 N: c,92.66; h,5.42; n,1.93. Measured element content (%): c,92.68; h,5.45; n,1.90.
Synthesis example 2: synthesis of Compound HT1-30
AA-3,BB-3 and DD-3 were successively replaced with AA-30, BB-30 and DD-30 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-30 (18.68 g, yield 78%). The purity of the solid detected by HPLC is not less than 99.95%. Mass spectrum m/z:797.3459 (theory: 797.3478). Theoretical element content (%) C 59 H 47 NSi: c,88.79; h,5.94; n,1.76. Measured element content (%): c,88.80; h,5.97; n,1.73.
Synthesis example 3: synthesis of Compound HT1-55
The AA-3, BB-3 and DD-3 were successively replaced with AA-50, DD-30 and DD-30 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-55 (18.05 g, yield 75%). The purity of the solid detected by HPLC is not less than 99.99%. Mass spectrum m/z:801.3375 (theory: 801.3396). Theoretical element content (%) C 62 H 43 N: c,92.85; h,5.40; n,1.75. Measured element content (%): c,92.84; h,5.42; n,1.74.
Synthesis example 4: synthesis of Compound HT1-60
AA-3, BB-3 and DD-3 were successively replaced with AA-55, BB-60 and DD-60 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-60 (17.56 g, yield 73%). The purity of the solid detected by HPLC is not less than 99.95%. Mass spectrum m/z:802.0345 (theory: 802.0330). Theoretical element content (%) C 62 H 43 N: c,92.85; h,5.40; n,1.75. Measured element content (%): c,92.86; h,5.44; n,1.72.
Synthesis example 5: synthesis of Compound HT1-66
The AA-3, BB-3 and DD-3 were successively replaced with AA-66, DD-30 and BB-60 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-66 (17.99 g, yield 74%). The purity of the solid detected by HPLC is not less than 99.95%. Mass spectrum m/z:810.3979 (theory: 810.3960). Theoretical element content (%) C 62 H 34 D 9 N: c,91.81; h,6.46; n,1.73. Measured element content (%): c,91.83; h,6.42; n,1.75.
Synthesis example 6: synthesis of Compound HT1-82
The same procedure as in Synthesis example 3 was followed except for substituting DD-30 with DD-82 in an equimolar amount to give Compound HT1-82 (17.68 g, yield 71%). The purity of the solid detected by HPLC is not less than 99.96%. Mass spectrum m/z:829.3721 (theory: 829.3709). Theoretical element content (%) C 64 H 47 N: c,92.61; h,5.71; n,1.69. Measured element content (%): c,92.66; h,5.68; n,1.68.
Synthesis example 7: synthesis of Compounds HT1-94
The AA-3, BB-3 and DD-3 were successively replaced with AA-94, DD-30 and BB-60 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-94 (16.48 g, yield 69%). The purity of the solid detected by HPLC is not less than 99.92%. Mass spectrum m/z:795.3878 (theory: 795.3865). Theoretical element content (%) C 61 H 49 N: c,92.04; h,6.20; n,1.76. Measured element content (%): c,92.06; h,6.25; n,1.72.
Synthesis example 8: synthesis of Compounds HT1-124
The AA-3, BB-3 and DD-3 were successively replaced with AA-124, DD-30 and DD-124 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-124 (17.75 g, 67% yield). The purity of the solid detected by HPLC is not less than 99.96%. Mass spectrum m/z:882.4039 (theory: 882.4022). Theoretical element content (%) C 68 H 42 D 5 N: c,92.48; h,5.93; n,1.59. Measured element content (%): c,92.47; h,5.96; n,1.58.
Synthesis example 9: synthesis of Compound HT1-142
The AA-3, BB-3 and DD-3 were successively replaced with AA-142, BB-142 and DD-30 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-142 (16.74 g, yield 76%). The purity of the solid detected by HPLC is not less than 99.93 percent. Mass spectrum m/z:733.3720 (theory: 733.3709). Theoretical element content (%) C 56 H 47 N: c,91.64; h,6.45; n,1.91. Measured element content (%): c,91.60; h,6.44; n,1.96.
Synthesis example 10: synthesis of Compounds HT1-162
BB-3 and DD-3 were successively replaced with BB-162 and DD-162 in equimolar amounts, and the same procedure as in Synthesis example 1 was repeated to obtain Compound HT1-162 (15.61 g, yield: 77%). The purity of the solid detected by HPLC is not less than 99.94%. Mass spectrum m/z:675.2912 (theory: 675.2926). Theoretical element content (%) C 52 H 37 N: c,92.41; h,5.52; n,2.07. Measured element content (%): c,92.46; h,5.49; n,2.06.
Synthesis example 11: synthesis of Compound HT1-202
The AA-3, BB-3 and DD-3 were successively replaced with AA-55, BB-202 and DD-202 in equimolar amounts, and the other steps were the same as those of Synthesis example 1, to obtain Compound HT1-202 (16.26 g, yield 74%). The purity of the solid detected by HPLC is not less than 99.95%. Mass spectrum m/z:751.3229 (theory: 751.3239). Theoretical element content (%) C 58 H 41 N: c,92.64; h,5.50; n,1.86. Measured element content (%): c,92.66; h,5.51; n,1.85.
Synthesis example 12: synthesis of Compound HT1-207
The AA-3, BB-3 and DD-3 were successively replaced with AA-55, BB-162 and DD-202 in equimolar amounts, and the other steps were the same as those of Synthesis example 1, to obtain Compound HT1-207 (16.02 g, yield 79%). The purity of the solid detected by HPLC is not less than 99.97%. Mass spectrum m/z:675.2935 (theory: 675.2926). Theoretical element content (%) C 52 H 37 N: c,92.41; h,5.52; n,2.07. Measured element content (%): c,92.40; h,5.57; n,2.05.
Synthesis example 13: synthesis of Compounds HT1-217
The AA-3, BB-3 and DD-3 were successively replaced with AA-55, BB-217 and DD-217 in equimolar amounts, and the other steps were the same as those of Synthesis example 1 to obtain Compound HT1-217 (15.21 g, yield 75%). The purity of the solid detected by HPLC is not less than 99.93 percent. Mass spectrum m/z:675.2908 (theory: 675.2926). Theoretical element content (%) C 52 H 37 N: c,92.41; h,5.52; n,2.07. Measured element content (%): c,92.39; h,5.54; n,2.08.
Synthesis example 14: synthesis of Compounds HT1-241
AA-3, BB-3 and DD-3 were successively replaced with AA-55, BB-241 and DD-241 in equimolar amounts, and the same procedure as in Synthesis example 1 was repeated to obtain Compound HT1-241 (17.38 g, yield: 71%). The purity of the solid detected by HPLC is not less than 99.91 percent. Mass spectrum m/z:815.4499 (theory: 815.4491). Theoretical element content (%) C 62 H 57 N: c,91.24; h,7.04; n,1.72. Measured element content (%): c,91.29; h,7.00; n,1.71.
Synthesis example 15: synthesis of Compounds HT1-259
AA-3, BB-3 and DD-3 were successively replaced with an equimolar amount of AA-259, BB-259 and DD-259, and the same procedure as in Synthesis example 1 was repeated to obtain Compound HT1-259 (15.84 g, 67% yield). The purity of the solid detected by HPLC is not less than 99.95%. Mass spectrum m/z:787.4196 (theory: 787.4178). Theoretical element content (%) C 60 H 53 N: c,91.44; h,6.78; n,1.78. Measured element content (%): c,91.40; h,6.80; n,1.79.
Synthesis example 16: synthesis of Compound HT1-278
The AA-3, BB-3 and DD-3 were successively replaced with AA-278, BB-162 and DD-202 in equimolar amounts, and the other steps were the same as those of Synthesis example 1, to obtain Compound HT1-278 (17.14 g, yield 76%). The purity of the solid detected by HPLC is not less than 99.96%. Mass spectrum m/z:751.3261 (theory: 751.3239). Theoretical element content (%) C 58 H 41 N: c,92.64; h,5.50; n,1.86. Measured element content (%): c,92.63; h,5.52; n,1.86.
Synthesis example 17: synthesis of Compound HT2-2
Aa-2 (9.44 g,30 mmol), bb-2 (22.08 g,90 mmol), sodium tert-butoxide (15.57 g,162 mmol) and 300ml toluene were added to the reaction flask under nitrogen and Pd was added with stirring 2 (dba) 3 (0.83 g,0.9 mmol) and 0.5M P (t-Bu) 3 Toluene solution (3.6 ml), and the above mixed solution was heated under reflux for 5 hours. After the completion of the reaction, the mixture was cooled to room temperature, washed with distilled water, then extracted with methylene chloride, and the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, and the obtained residue was recrystallized from toluene weight/methanol (volume ratio 8:1) to give compound HT2-2 (19.15 g, 79%). The purity of the solid detected by HPLC is not less than 99.97%. Mass spectrum m/z:807.3623 (theory: 807.3613). Theoretical element content (%) C 60 H 45 N 3 : c,89.19; h,5.61; n,5.20. Measured element content (%): c,89.17; h,5.59; n,5.24.
Synthesis example 18: synthesis of Compound HT2-10
Aa-10 (13.52 g,50 mmol), bb-10 (16.92 g,100 mmol), sodium tert-butoxide (17.3 g,180 mmol) and 400ml toluene were added to the flask under nitrogen and Pd (dppf) Cl was added with stirring 2 (0.73 g,1 mmol) and 0.5M P (t-Bu) 3 Toluene solution (4 ml), and the above mixed solution was heated under reflux for 4 hours. After the completion of the reaction, the mixture was cooled to room temperature, washed with distilled water, then extracted with methylene chloride, the organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and the obtained residue was recrystallized from toluene/methanol (volume ratio 6:1) to give compound cc-10 (16.76 g, 75%). Mass spectrum m/z:446.1538 (theory: 446.1550).
To a reaction flask was added cc-10 (13.41 g,30 mmol), dd-10 (9.64 g,30 mmol), sodium tert-butoxide (5.29 g,55 mmol) and 150ml toluene under nitrogen,pd is added under stirring 2 (dba) 3 (0.28 g,0.3 mmol) and 0.5M P (t-Bu) 3 Toluene solution (1.2 ml), the above mixed solution was heated under reflux for 4.5 hours. After the completion of the reaction, the mixture was cooled to room temperature, washed with distilled water, then extracted with methylene chloride, the organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and the obtained residue was recrystallized from toluene/methanol (volume ratio 8:1) to give compound HT2-10 (15.81 g, 72%). The purity of the solid detected by HPLC is not less than 99.96%. Mass spectrum m/z:731.3319 (theory: 731.3300). Theoretical element content (%) C 54 H 41 N 3 : c,88.61; h,5.65; n,5.74. Measured element content (%): c,88.65; h,5.61; n,5.74.
Synthesis example 19: synthesis of Compound HT2-32
The procedure of Synthesis example 18 was followed except for successively substituting bb-10 and dd-10 with bb-32 and dd-32 in equimolar amounts, thereby obtaining Compound HT2-32 (19.36 g, 73%). The purity of the solid detected by HPLC is not less than 99.98%. Mass spectrum m/z:883.3905 (theory: 883.3926). Theoretical element content (%) C 66 H 49 N 3 : c,89.66; h,5.59; n,4.75. Measured element content (%): c,89.68; h,5.62; n,4.72.
Synthesis example 20: synthesis of Compound HT2-37
The procedure of Synthesis example 18 was followed except for successively substituting bb-10 and dd-10 with bb-2 and dd-37 in equimolar amounts, thereby obtaining Compound HT2-37 (18.33 g, 76%). The purity of the solid detected by HPLC is not less than 99.93 percent. Mass spectrum m/z:803.3684 (theory: 803.3696). Theoretical element content (%) C 57 H 49 N 3 Si: c,85.14; h,6.14; n,5.23. Measured element content (%): c,85.17; h,6.15; n,5.19.
Synthesis example 21: synthesis of Compound HT2-95
The procedure of Synthesis example 20 was followed except for substituting dd-37 with an equimolar amount of dd-95 to give Compound HT2-95 (19.31 g, 72%). The purity of the solid detected by HPLC is not less than 99.96%. Mass spectrum m/z:893.4573 (theory: 893.4554). Theoretical element content (%) C 66 H 39 D 10 N 3 : c,88.65; h,6.65; n,4.70. Measured element content (%): c,88.60; h,6.68; n,4.71.
Synthesis example 22: synthesis of Compound HT2-115
The procedure of Synthesis example 17 was followed except for substituting bb-2 with an equimolar amount of bb-115 to give Compound HT2-115 (14.28 g, 80%). The purity of the solid detected by HPLC is not less than 99.95%. Mass spectrum m/z:594.3634 (theory: 594.3616). Theoretical element content (%) C 42 H 18 D 15 N 3 : c,84.81; h,8.13; n,7.06. Measured element content (%): c,84.80; h,8.17; n,7.05.
Synthesis example 23: synthesis of Compound HT2-140
Aa-140 (25.39 g,80 mmol), bb-10 (13.54 g,80 mmol), sodium tert-butoxide (13.93 g,145 mmol) and 450ml toluene were added to the flask under nitrogen, pd (PPh) was added with stirring 3 ) 4 (1.11 g,0.96 mmol) and 0.5M P (t-Bu) 3 Toluene solution (3 ml), and the above mixed solution was heated under reflux for 3 hours. After the reaction, the mixture was cooled to room temperature, washed with distilled water, extracted with dichloromethane, and the organic phase was separatedThe phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and the obtained residue was recrystallized from toluene weight/methanol (volume ratio 5:1) to give compound cc-140 (20.37 g, 71%). Mass spectrum m/z:356.9905 (theory: 356.9920).
Into a reaction flask were charged cc-140 (17.93 g,50 mmol), bb-2 (12.27 g,50 mmol), sodium tert-butoxide (9.13 g,95 mmol) and 300ml toluene under nitrogen, pd (dppf) Cl with stirring 2 (0.44 g,0.6 mmol) and 0.5M P (t-Bu) 3 Toluene solution (2 ml), and the above mixed solution was heated under reflux for 4 hours. After the completion of the reaction, the mixture was cooled to room temperature, washed with distilled water, then extracted with methylene chloride, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure, and the obtained residue was recrystallized from toluene weight/methanol (volume ratio 6:1) to give compound ee-140 (18.05 g, 69%). Mass spectrum m/z:523.0779 (theory: 523.0760).
Into a reaction flask were charged ee-140 (15.69 g,30 mmol), dd-32 (9.64 g,30 mmol), sodium tert-butoxide (5.29 g,55 mmol) and 150ml toluene under nitrogen, pd was added with stirring 2 (dba) 3 (0.28 g,0.3 mmol) and 0.5M P (t-Bu) 3 Toluene solution (1.2 ml), the above mixed solution was heated under reflux for 4.5 hours. After the completion of the reaction, the mixture was cooled to room temperature, washed with distilled water, then extracted with methylene chloride, and the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, and the obtained residue was recrystallized from toluene weight/methanol (volume ratio 8:1) to give compound HT2-140 (16.97 g, 70%). The purity of the solid detected by HPLC is not less than 99.94%. Mass spectrum m/z:807.3601 (theory: 807.3613). Theoretical element content (%) C 60 H 45 N 3 : c,89.19; h,5.61; n,5.20. Measured element content (%): c,89.17; h,5.65; n,5.19.
Synthesis example 24: synthesis of Compound HT2-145
Substitution of bb-2 to equal molar amounts of bb-145, other steps being followed by synthesisThe same as in example 23, compound HT2-145 (17.98 g, 71%) was obtained. The purity of the solid detected by HPLC is not less than 99.93 percent. Mass spectrum m/z:843.4561 (theory: 843.4552). Theoretical element content (%) C 62 H 57 N 3 : c,88.22; h,6.81; n,4.98. Measured element content (%): c,88.26; h,6.83; n,4.93.
Synthesis example 25: synthesis of Compound HT2-153
Aa-2 and bb-2 were successively replaced with aa-153 and bb-153 in equimolar amounts, and the procedure was otherwise identical to that of Synthesis example 17, to give Compound HT2-153 (17.58 g, 78%). The purity of the solid detected by HPLC is not less than 99.93 percent. Mass spectrum m/z:750.4754 (theory: 750.4741). Theoretical element content (%) C 54 H 54 D 3 N 3 : c,86.35; h,8.05; n,5.59. Measured element content (%): c,86.33; h,8.04; n,5.63.
Synthesis example 26: synthesis of Compound HT2-162
Aa-2 and bb-2 were successively replaced with aa-162 and bb-10 in equimolar amounts, and the procedure was otherwise identical to that of Synthesis example 17, to give Compound HT2-162 (13.99 g, 75%). The purity of the solid detected by HPLC is not less than 99.92%. Mass spectrum m/z:621.3160 (theory: 621.3144). Theoretical element content (%) C 45 H 39 N 3 : c,86.92; h,6.32; n,6.76. Measured element content (%): c,86.94; h,6.35; n,6.71.
The following are other compounds used in the device preparation examples in addition to the compounds of formula (I) and formula (II) described in the present invention:
the organic materials in the device preparation examples are purified by sublimation, and the purity is over 99.99 percent. The ITO glass substrate and the ITO/Ag/ITO glass substrate used in the device preparation example are all purchased in the market.
Test software, a computer, a K2400 digital source meter from Keithley company, U.S. and a PR788 spectral scanning luminance meter from Photo Research, U.S. are combined into a combined IVL test system, and the device prepared by the invention is tested at atmospheric pressure and room temperature at a current density of 15mA/cm 2 Light-emitting efficiency and driving voltage at the time. The lifetime of the devices prepared according to the invention (decay of brightness to 95% of the initial brightness) was tested using the Mcscience M6000 OLED lifetime test system at atmospheric pressure and room temperature. The test results are shown in tables 1 to 4.
Comparative device preparation example 1: contrast device 1
Firstly, an ITO glass substrate is ultrasonically cleaned by deionized water for 2 times each for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO glass substrate: a. hat is used as a hole injection layer, and the thickness is 10nm; b. HT1-55 as a first hole transport layer, having a thickness of 50nm; c. BANE and BD (mass ratio 97:3) as light emitting layers with thickness of 30nm; d. TPBi is used as a hole blocking layer, and the thickness is 20nm; e. HNBEN and Liq (mass ratio 3:2) are used as electron transport layers with the thickness of 20nm; f. LiF is used as an electron injection layer, and the thickness is 1nm; g. al was used as a cathode and the thickness was 100nm.
Comparative device preparation examples 2 to 7: contrast devices 2 to 7
The HT1-55 in the first hole transport layer was replaced with HT1-60, HT1-207, HT1-259, HT2-2, HT2-95, HT2-177, respectively, and the other steps were the same as those of comparative device preparation 1, thereby obtaining comparative devices 2-7.
Device preparation example 1: device 1
Firstly, an ITO glass substrate is ultrasonically cleaned by deionized water for 2 times each for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO glass substrate: a. hat is used as a hole injection layer, and the thickness is 10nm; b. HT1-3 as a first hole transport layer, having a thickness of 25nm; c. HT2-10 is used as a light-emitting auxiliary layer, and the thickness is 25nm; d. BANE and BD (mass ratio 97:3) as light emitting layers with thickness of 30nm; e. TPBi is used as a hole blocking layer, and the thickness is 20nm; f. HNBEN and Liq (mass ratio 3:2) are used as electron transport layers with the thickness of 20nm; g. LiF is used as an electron injection layer, and the thickness is 1nm; h. al was used as a cathode and the thickness was 100nm.
Device preparation example 2: device 2
The device 2 was obtained by replacing HT1-3 in the first hole transport layer with HT1-30, replacing HT2-10 in the light emitting auxiliary layer with HT2-32, and performing the same procedure as in device manufacturing example 1.
Device preparation example 3: device 3
The device 3 was obtained by replacing HT1-3 in the first hole transport layer with HT1-55, replacing HT2-10 in the light emitting auxiliary layer with HT2-2, and performing the same procedure as in device manufacturing example 1.
Device preparation example 4: device 4
The device 4 was obtained by replacing HT1-3 in the first hole transport layer with HT1-55, replacing HT2-10 in the light emitting auxiliary layer with HT2-115, and performing the same procedure as in device manufacturing example 1.
Device preparation example 5: device 5
The device 5 was obtained by replacing HT1-3 in the first hole transport layer with HT1-55, replacing HT2-10 in the light emitting auxiliary layer with HT2-145, and performing the same procedure as in device manufacturing example 1.
Device preparation example 6: device 6
The device 6 was obtained by replacing HT1-3 in the first hole transport layer with HT1-60, replacing HT2-10 in the light emitting auxiliary layer with HT2-95, and performing the same procedure as in device manufacturing example 1.
Device preparation example 7: device 7
The device 7 was obtained by replacing HT1-3 in the first hole transport layer with HT1-66, replacing HT2-10 in the light emitting auxiliary layer with HT2-2, and performing the same procedure as in device manufacturing example 1.
Device preparation example 8: device 8
The device 8 was obtained by replacing HT1-3 in the first hole transport layer with HT1-66, replacing HT2-10 in the light emitting auxiliary layer with HT2-162, and performing the same procedure as in device manufacturing example 1.
Device preparation example 9: device 9
The device 9 was obtained by replacing HT1-3 in the first hole transport layer with HT1-82, replacing HT2-10 in the light emitting auxiliary layer with HT2-140, and performing the same procedure as in device manufacturing example 1.
Device preparation example 10: device 10
The device 10 was obtained by replacing HT1-3 in the first hole transport layer with HT1-94, replacing HT2-10 in the light emitting auxiliary layer with HT2-115, and performing the same procedure as in device manufacturing example 1.
Device preparation example 11: device 11
The device 11 was obtained by replacing HT1-3 in the first hole transport layer with HT1-124, replacing HT2-10 in the light emitting auxiliary layer with HT2-37, and performing the same procedure as in device manufacturing example 1.
Device preparation example 12: device 12
The device 12 was obtained by replacing HT1-3 in the first hole transport layer with HT1-142, replacing HT2-10 in the light emitting auxiliary layer with HT2-2, and performing the same procedure as in device manufacturing example 1.
Device preparation example 13: device 13
The device 13 was obtained by replacing HT1-3 in the first hole transport layer with HT1-162, replacing HT2-10 in the light emitting auxiliary layer with HT2-145, and performing the same procedure as in device manufacturing example 1.
Device preparation example 14: device 14
The device 14 was obtained by replacing HT1-3 in the first hole transport layer with HT1-202, replacing HT2-10 in the light emitting auxiliary layer with HT2-153, and performing the same steps as those of device manufacturing example 1.
Device preparation example 15: device 15
The device 15 was obtained by replacing HT1-3 in the first hole transport layer with HT1-207, replacing HT2-10 in the light emitting auxiliary layer with HT2-2, and performing the same procedure as in device manufacturing example 1.
Device preparation example 16: device 16
The device 16 was obtained by replacing HT1-3 in the first hole transport layer with HT1-207, replacing HT2-10 in the light emitting auxiliary layer with HT2-32, and performing the same procedure as in device manufacturing example 1.
Device preparation example 17: device 17
The device 17 was obtained by replacing HT1-3 in the first hole transport layer with HT1-217, replacing HT2-10 in the light emitting auxiliary layer with HT2-115, and performing the same procedure as in device manufacturing example 1.
Device preparation example 18: device 18
The device 18 was obtained by replacing HT1-3 in the first hole transport layer with HT1-241, and performing the same procedure as in device manufacturing example 1.
Device preparation example 19: device 19
The device 19 was obtained by replacing HT1-3 in the first hole transport layer with HT1-259 and replacing HT2-10 in the light emitting auxiliary layer with HT2-140, and the other steps were the same as those of device manufacturing example 1.
Device preparation example 20: device 20
The device 20 was obtained by replacing HT1-3 in the first hole transport layer with HT1-278, replacing HT2-10 in the light emitting auxiliary layer with HT2-162, and performing the same procedure as in device manufacturing example 1.
TABLE 1
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Comparative device preparation example 8: contrast device 8
Firstly, an ITO glass substrate is ultrasonically cleaned by deionized water for 2 times each for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO glass substrate: a. 2-TNATA is used as a hole injection layer with the thickness of 50nm; b. HT1-30 is used as a first hole transport layer, and the thickness is 70nm; c. RH-1, RH-2 and Ir (dpm) PQ 2 (mass ratio of 64:32:4) as a light-emitting layer, the thickness was 35nm; d. TPBi is used as a hole blocking layer, and the thickness is 25nm; e. HNBEN and Liq (mass ratio 6:1) are used as electron transport layers with thickness of 25nm; f. LiF is used as an electron injection layer, and the thickness is 1nm; g. al was used as a cathode and the thickness was 100nm.
Comparative device preparation examples 9 to 12: contrast devices 9-12
The comparative devices 9 to 12 were obtained by replacing HT1-30 in the first hole transport layer with HT1-55, HT1-207, HT2-2, HT2-95, respectively, and performing the same procedure as in comparative device preparation 8.
Device preparation example 21: device 21
Firstly, an ITO glass substrate is ultrasonically cleaned by deionized water for 2 times each for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO glass substrate: a. 2-TNATA is used as a hole injection layer with the thickness of 50nm; b. HT1-30 is used as a first hole transport layer, and the thickness is 20nm; c. HT1-60 is used as a second hole transport layer, and the thickness is 25nm; d. HT2-2 is used as a light-emitting auxiliary layer, and the thickness is 25nm; e. RH-1, RH-2 and Ir (dpm) PQ 2 (mass ratio of 64:32:4) as a light-emitting layer, the thickness was 35nm; f. TPBi is used as a hole blocking layer, and the thickness is 25nm; g. HNBEN and Liq (mass ratio 6:1) are used as electron transport layers with thickness of 25nm; h. LiF is used as an electron injection layer, and the thickness is 1nm; i. al was used as a cathode and the thickness was 100nm.
Device preparation example 22: device 22
The device 22 was obtained by replacing HT1-60 in the second hole transport layer with HT1-94, replacing HT2-2 in the light emitting auxiliary layer with HT2-95, and performing the same procedure as in device manufacturing example 21.
Device preparation example 23: device 23
Device 23 was obtained by replacing HT1-30 in the first hole transport layer with HT1-55, and performing the same procedure as in device manufacturing example 21.
Device preparation example 24: device 24
Device 24 was obtained by replacing HT1-30 in the first hole transport layer with HT1-55, replacing HT2-2 in the light emitting auxiliary layer with HT2-115, and performing the same procedure as in device manufacturing example 21.
Device preparation example 25: device 25
The device 25 was obtained by replacing HT1-30 in the first hole transport layer with HT1-55, replacing HT1-60 in the second hole transport layer with HT1-259, replacing HT2-2 in the light emitting auxiliary layer with HT2-32, and performing the same procedure as in device manufacturing example 21.
Device preparation example 26: device 26
The device 26 was obtained by replacing HT1-30 in the first hole transport layer with HT1-82, replacing HT1-60 in the second hole transport layer with HT1-3, replacing HT2-2 in the light emitting auxiliary layer with HT2-140, and performing the same procedure as in device manufacturing example 21.
Device preparation example 27: device 27
The device 27 was obtained by replacing HT1-30 in the first hole transport layer with HT1-124, replacing HT1-60 in the second hole transport layer with HT1-217, replacing HT2-2 in the light emitting auxiliary layer with HT2-37, and performing the same procedure as in device manufacturing example 21.
Device preparation example 28: device 28
The device 28 was obtained by replacing HT1-30 in the first hole transport layer with HT1-162, replacing HT1-60 in the second hole transport layer with HT1-241, replacing HT2-2 in the light emitting auxiliary layer with HT2-32, and performing the same procedure as in device manufacturing example 21.
Device preparation example 29: device 29
The device 29 was obtained by replacing HT1-30 in the first hole transport layer with HT1-207, replacing HT2-2 in the light emitting auxiliary layer with HT2-32, and performing the same procedure as in device manufacturing example 21.
Device preparation example 30: device 30
The device 30 was obtained by replacing HT1-30 in the first hole transport layer with HT1-207, replacing HT1-60 in the second hole transport layer with HT1-217, replacing HT2-2 in the light emitting auxiliary layer with HT2-115, and performing the same procedure as in device manufacturing example 21.
Device preparation example 31: device 31
The device 31 was obtained by replacing HT1-30 in the first hole transport layer with HT1-207, replacing HT1-60 in the second hole transport layer with HT1-259, replacing HT2-2 in the light emitting auxiliary layer with HT2-95, and performing the same procedure as in device manufacturing example 21.
TABLE 2
Comparative device preparation example 13: contrast device 13
Firstly, the ITO/Ag/ITO glass substrate is ultrasonically cleaned by deionized water for 2 times, each time for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO/Ag/ITO glass substrate: a. HT1-30 and p-1 (mass ratio of 20:1) are used as hole injection layers, and the thickness is 20nm; b. HT1-30 is used as a first hole transport layer, and the thickness is 65nm; c. GH-1, GH-2 and Ir (ppy) 2 (m-bppy) (mass ratio 48:48:4) as a light-emitting layer, thickness was 35nm; d. BAlq is used as a hole blocking layer with the thickness of 35nm; e. HNBEN and Liq (mass ratio 7:1) are used as electron transport layers with the thickness of 20nm; f. LiF is used as an electron injection layer, and the thickness is 0.1nm; g. mg and Ag (mass ratio 7:3) are used as cathodes with the thickness of 10nm; h: CP-4 as coating layer with thickness of 100nm。
Comparative device preparation examples 14 to 18: contrast devices 14-18
The hole injection layer and HT1-30 in the first hole transport layer were replaced with HT1-55, HT1-207, HT2-2, HT2-32, HT2-115, respectively, and the other steps were the same as those of comparative device preparation 13, thereby obtaining comparative devices 14-18.
Device preparation example 32: device 32
Firstly, the ITO/Ag/ITO glass substrate is ultrasonically cleaned by deionized water for 2 times, each time for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO/Ag/ITO glass substrate: a. HT1-30 and p-1 (mass ratio of 20:1) are used as hole injection layers, and the thickness is 20nm; b. HT1-30 is used as a first hole transport layer, and the thickness is 20nm; c. HT2-2 is used as a light-emitting auxiliary layer, and the thickness is 25nm; d. HT1-60 is used as a second hole transport layer, and the thickness is 20nm; e. GH-1, GH-2 and Ir (ppy) 2 (m-bppy) (mass ratio 48:48:4) as a light-emitting layer, thickness was 35nm; f. BAlq is used as a hole blocking layer with the thickness of 35nm; g. HNBEN and Liq (mass ratio 7:1) are used as electron transport layers with the thickness of 20nm; h. LiF is used as an electron injection layer, and the thickness is 0.1nm; i. mg and Ag (mass ratio 7:3) are used as cathodes with the thickness of 10nm; j: CP-4 was used as a coating layer with a thickness of 100nm.
Device preparation example 33: device 33
The device 33 was obtained by replacing HT2-2 in the light-emitting auxiliary layer with HT2-145, replacing HT1-60 in the second hole transport layer with HT1-217, and performing the same procedure as in device manufacturing example 32.
Device preparation example 34: device 34
The device 34 was obtained by replacing HT1-30 in the hole injection layer and the first hole transport layer with HT1-55, replacing HT1-60 in the second hole transport layer with HT1-66, and performing the same procedure as in device manufacturing example 32.
Device preparation example 35: device 35
The device 35 can be obtained by replacing HT1-30 in the hole injection layer and the first hole transport layer with HT1-55, replacing HT2-2 in the light emitting auxiliary layer with HT2-115, replacing HT1-60 in the second hole transport layer with HT1-217, and performing the same steps as those in device manufacturing example 32.
Device preparation example 36: device 36
The device 36 can be obtained by replacing HT1-30 in the hole injection layer and the first hole transport layer with HT1-124, replacing HT2-2 in the light emitting auxiliary layer with HT2-32, replacing HT1-60 in the second hole transport layer with HT1-217, and performing the same steps as those in device manufacturing example 32.
Device preparation example 37: device 37
The device 37 was obtained by replacing HT1-30 in the hole injection layer and the first hole transport layer with HT1-207, replacing HT2-2 in the light emitting auxiliary layer with HT2-95, and performing the same procedure as in device manufacturing example 32.
Device preparation example 38: device 38
The device 38 was obtained by replacing HT1-30 in the hole injection layer and the first hole transport layer with HT1-207, replacing HT2-2 in the light emitting auxiliary layer with HT2-115, replacing HT1-60 in the second hole transport layer with HT1-94, and performing the same procedure as in device manufacturing example 32.
Device preparation example 39: device 39
The device 39 was obtained by replacing HT1-30 in the hole injection layer and the first hole transport layer with HT1-278, replacing HT2-2 in the light emitting auxiliary layer with HT2-95, replacing HT1-60 in the second hole transport layer with HT1-66, and performing the same procedure as in device manufacturing example 32.
TABLE 3 Table 3
Comparative device preparation example 19: contrast device 19
Firstly, the ITO/Ag/ITO glass substrate is ultrasonically cleaned by deionized water for 2 times, each time for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO/Ag/ITO glass substrate: a. HT1-30 and p-1 (mass ratio of 20:1) are used as hole injection layers, and the thickness is 25nm; b. HT1-30 is used as a first hole transport layer, and the thickness is 100nm; c. RH-1, RH-3 and Ir (dpm) (piq) 2 (mass ratio 48:48:4) as a light-emitting layer, thickness was 35nm; d. TPBi is used as a hole blocking layer, and the thickness is 25nm; e. HNBEN and Liq (mass ratio 9:1) are used as electron transport layers with the thickness of 20nm; f. LiF is used as an electron injection layer, and the thickness is 0.1nm; g. mg and Ag (mass ratio 7:3) are used as cathodes with the thickness of 10nm; h: CP-4 was used as a coating layer with a thickness of 100nm.
Comparative device preparation examples 20 to 24: contrast devices 20-24
The hole injection layer and HT1-30 in the first hole transport layer were replaced with HT1-55, HT1-207, HT2-2, respectively, and the other steps were the same as those of comparative device preparation 19, thereby obtaining comparative devices 20-24.
Device preparation example 40: device 40
Firstly, the ITO/Ag/ITO glass substrate is ultrasonically cleaned by deionized water for 2 times, each time for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.
The following layers are evaporated layer by layer on the ITO/Ag/ITO glass substrate: a. HT1-30 and p-1 (mass ratio of 20:1) are used as hole injection layers, and the thickness is 25nm; b. HT1-30 is used as a first hole transport layer, and the thickness is 30nm; c. HT1-66 as a second hole transport layer, having a thickness of 20nm; d. HT2-2 is used as a light-emitting auxiliary layer, and the thickness is 30nm; e. HT1-60 is used as a third hole transport layer, and the thickness is 20nm; f. RH-1, RH-3 and Ir (dpm) (piq) 2 (mass ratio 48:48:4) as a light-emitting layer, thickness was 35nm; g. TPBi is used as a hole blocking layer, and the thickness is 25nm; h. HNBEN and Liq (mass ratio 9:1) are used as electron transport layers with the thickness of 20nm; i. LiF is used as an electron injection layer, and the thickness is 0.1nm; j. mg and Ag (mass ratio 7:3) are used as cathodes with the thickness of 10nm; k: CP-4 as a coating layer, thickness 100nm。
Device preparation example 41: device 41
The device 41 was obtained by replacing HT1-66 in the second hole transport layer with HT1-94, replacing HT2-2 in the light emitting auxiliary layer with HT2-10, replacing HT1-60 in the third hole transport layer with HT1-217, and performing the same procedure as in device manufacturing example 40.
Device preparation example 42: device 42
The device 42 was obtained by replacing HT1-30 in the first hole transport layer with HT1-55, replacing HT1-66 in the second hole transport layer with HT1-3, replacing HT2-2 in the light emitting auxiliary layer with HT2-32, replacing HT1-60 in the third hole transport layer with HT1-217, and performing the same procedure as in device manufacturing example 40.
Device preparation example 43: device 43
The device 43 was obtained by replacing HT1-30 in the first hole transport layer with HT1-55, replacing HT1-66 in the second hole transport layer with HT1-202, replacing HT2-2 in the light emitting auxiliary layer with HT2-115, and performing the same procedure as in device manufacturing example 40.
Device preparation example 44: device 44
The device 44 was obtained by replacing HT1-30 in the first hole transport layer with HT1-55, replacing HT1-66 in the second hole transport layer with HT1-259, replacing HT2-2 in the light emitting auxiliary layer with HT2-95, and performing the same procedure as in device manufacturing example 40.
Device preparation example 45: device 45
The device 45 was obtained by replacing HT1-30 in the first hole transport layer with HT1-124, replacing HT1-66 in the second hole transport layer with HT1-241, replacing HT2-2 in the light emitting auxiliary layer with HT2-37, replacing HT1-60 in the third hole transport layer with HT1-3, and performing the same procedure as in device manufacturing example 40.
Device preparation example 46: device 46
The device 46 was obtained by replacing HT1-30 in the first hole transport layer with HT1-207, replacing HT1-60 in the third hole transport layer with HT1-217, and performing the same procedure as in device manufacturing example 40.
Device preparation example 47: device 47
The device 47 was obtained by replacing HT1-30 in the first hole transport layer with HT1-207, replacing HT1-66 in the second hole transport layer with HT1-259, replacing HT2-2 in the light emitting auxiliary layer with HT2-115, and performing the same procedure as in device manufacturing example 40.
Device preparation example 48: device 48
The device 48 was obtained by replacing HT1-30 in the first hole transport layer with HT1-207, replacing HT1-66 in the second hole transport layer with HT1-60, replacing HT2-2 in the light emitting auxiliary layer with HT2-95, replacing HT1-60 in the third hole transport layer with HT1-217, and performing the same procedure as in device manufacturing example 40.
Device preparation example 49: device 49
The device 49 was obtained by replacing HT1-30 in the first hole transport layer with HT1-241, replacing HT2-2 in the light emitting auxiliary layer with HT2-162, and performing the same procedure as in device manufacturing example 40.
TABLE 4 Table 4
The device data in tables 1 to 4 show that the organic electroluminescent device of the present invention has excellent driving voltage, luminous efficiency and life performance by using the hole transport region of a specific structure.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.
Claims (10)
1. The organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode, the organic layer comprises a hole transmission area, a luminescent layer and an electron transmission area, the hole transmission area comprises a first hole transmission layer and a luminescent auxiliary layer, the first hole transmission layer is positioned between the anode and the luminescent layer, and the luminescent auxiliary layer is positioned between the first hole transmission layer and the luminescent layer.
In formula (I), the Ar 1 、Ar 2 Independently selected from one of the structures shown below:
wherein, a is as follows 1 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 1 Each occurrence is identically or differently selected from 0, 1, 2 or 3; the said c 1 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5;
said R is 1 、R 2 Independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or substituted C1 to C12 alkyl group;
said R is 3 Each occurrence is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 alicyclic ring, and two adjacent R 3 Capable of being linked to form a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C6-C10 aromatic ringOne of the two;
ar as described 3 One selected from the group consisting of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
the L is 1 ~L 3 Independently selected from one of single bond, substituted or unsubstituted arylene of C6-C30, and divalent group formed by fusing substituted or unsubstituted aromatic ring of C6-C30 and aliphatic ring of C3-C7;
in formula (II), said a 101 Selected from 0, 1, 2 or 3;
said R is 101 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, and a group in which a substituted or unsubstituted C6-C30 aromatic ring is condensed with a C3-C7 aliphatic ring;
ar as described 101 ~Ar 106 Independently selected from one of the structures shown below:
wherein, a is as follows 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said c 102 Each occurrence is identically or differently selected from 0, 1, 2 or 3; d is as follows 102 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6;
said R is 102 Each occurrence of which is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phenyl group One of the groups formed by fusing an unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
said R is 103 Each occurrence of which is identically or differently selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C12 alkyl group;
the L is 101 ~L 106 Independently selected from a single bond or one of the structures shown below:
wherein, a is as follows 103 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 103 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said c 103 Each occurrence is identically or differently selected from 0, 1 or 2; d is as follows 103 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6;
said R is 104 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, and a phenyl group substituted or unsubstituted by a deuterium atom;
said R is 105 And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, identically or differently at each occurrence.
2. The organic electroluminescent device of claim 1, wherein Ar 3 One selected from the following structures:
wherein, a is as follows 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 3 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; the said c 3 Each occurrence is identically or differently selected from 0, 1, 2 or 3; d is as follows 3 Each occurrence is identically or differently selected from 0, 1 or 2; said e 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
said R is 6 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
said R is 7 And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, identically or differently at each occurrence.
3. The organic electroluminescent device of claim 1, wherein L is 1 ~L 3 Independently selected from a single bond or one of the structures shown below:
wherein, a is as follows 2 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 2 Each occurrence is identically or differently selected from 0, 1, 2 or 3; the said c 2 Each occurrence is identically or differently selected from 0, 1 or 2; d is as follows 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
said R is 4 Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or substituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;
said R is 5 And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, identically or differently at each occurrence.
4. The organic electroluminescent device according to claim 1, wherein the compound represented by formula (I) is selected from one of the following compounds:
5. the organic electroluminescent device according to claim 1, wherein the compound represented by formula (II) is selected from one of the following compounds:
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6. the organic electroluminescent device according to claim 1, wherein the hole transport region further comprises a second hole transport layer between the first hole transport layer and the light-emitting auxiliary layer, wherein the second hole transport layer contains one of the compounds represented by formula (I) and is different from the compound in the first hole transport layer.
7. The organic electroluminescent device according to claim 1, wherein the hole transport region further comprises a second hole transport layer between the light-emitting auxiliary layer and the light-emitting layer, wherein the second hole transport layer contains one of the compounds represented by formula (I) and is different from the compound in the first hole transport layer.
8. The organic electroluminescent device according to claim 6, wherein the hole transport region further comprises a third hole transport layer between the light-emitting auxiliary layer and the light-emitting layer, wherein the third hole transport layer contains one of the compounds represented by formula (I), is different from the compound in the first hole transport layer, and is different from the compound in the second hole transport layer.
9. The organic electroluminescent device according to any one of claims 1 to 8, wherein the light-emitting auxiliary layer is a single layer structure composed of a single substance which is a compound represented by formula (II).
10. The organic electroluminescent device according to any one of claims 1 to 8, wherein the light-emitting auxiliary layer is a double layer structure composed of two substances, each of which is selected from the group consisting of the compounds represented by formula (II), and the two substances are different compounds.
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