CN113429370B - Aromatic amine compound and organic electroluminescent device thereof - Google Patents
Aromatic amine compound and organic electroluminescent device thereof Download PDFInfo
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- CN113429370B CN113429370B CN202110855946.6A CN202110855946A CN113429370B CN 113429370 B CN113429370 B CN 113429370B CN 202110855946 A CN202110855946 A CN 202110855946A CN 113429370 B CN113429370 B CN 113429370B
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- deuterated
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- aromatic amine
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- -1 Aromatic amine compound Chemical class 0.000 title claims abstract description 121
- 239000010410 layer Substances 0.000 claims abstract description 93
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 125000002723 alicyclic group Chemical group 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001975 deuterium Chemical group 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 27
- 230000005540 biological transmission Effects 0.000 abstract description 17
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 9
- 238000004020 luminiscence type Methods 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 3
- 239000002346 layers by function Substances 0.000 abstract description 2
- 238000003878 thermal aging Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 65
- 238000003786 synthesis reaction Methods 0.000 description 64
- 238000002360 preparation method Methods 0.000 description 37
- 238000001819 mass spectrum Methods 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 238000004128 high performance liquid chromatography Methods 0.000 description 27
- 125000001624 naphthyl group Chemical group 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 21
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 20
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 20
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000001514 detection method Methods 0.000 description 19
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- 239000002356 single layer Substances 0.000 description 15
- 125000000732 arylene group Chemical group 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- 125000001725 pyrenyl group Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 11
- 125000004431 deuterium atom Chemical group 0.000 description 10
- 125000005549 heteroarylene group Chemical group 0.000 description 10
- 125000005561 phenanthryl group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 8
- 125000004988 dibenzothienyl group Chemical class C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 125000004957 naphthylene group Chemical group 0.000 description 7
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 7
- 125000005580 triphenylene group Chemical group 0.000 description 7
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 125000005259 triarylamine group Chemical group 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 5
- 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 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000037230 mobility Effects 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 4
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 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
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 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 3
- 150000001716 carbazoles Chemical group 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000005567 fluorenylene group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 3
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000006836 terphenylene group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000004306 triazinyl group Chemical group 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 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
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 2
- VFTQRHWULYJKCI-UHFFFAOYSA-N 3-(1-adamantyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine Chemical compound C1CCCCN2C(C34CC5CC(C4)CC(C3)C5)=NN=C21 VFTQRHWULYJKCI-UHFFFAOYSA-N 0.000 description 2
- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 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
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- 229940125758 compound 15 Drugs 0.000 description 2
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
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- 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
- 239000011777 magnesium Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 125000003136 n-heptyl 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])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
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- 125000003438 dodecyl 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 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
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- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
The invention relates to the technical field of organic photoelectric materials, in particular to an arylamine compound and an organic electroluminescent device thereof. The arylamine compound of the formula (I) provided by the invention has good thermal stability, film forming property and hole transmission capability, has more proper HOMO and T1 values relative to other functional layers, especially luminescent layers, and can effectively avoid interface luminescence between the luminescent layers and a hole transmission region, thereby reducing the thermal aging speed of organic materials due to interface luminescence, and further improving the driving voltage, luminous efficiency and service life of devices.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an arylamine compound and an organic electroluminescent device thereof.
Background
Organic Light-Emitting Diode (OLED) has been used to a certain extent in the field of lighting and display due to its advantages of small thickness, light weight, wide viewing angle, short response time, wide application temperature range, low energy consumption, high luminous efficiency, good color purity, good flexibility, etc.
The OLED device is in a sandwich structure and comprises a cathode, an anode and an organic layer arranged between the cathode and the anode, wherein the organic layer is divided into a hole transmission area, an electron transmission area, a light emitting area and the like according to different functions. Under the action of an external electric field, holes and electrons are respectively injected from an anode and a cathode, enter a light-emitting area through a hole transmission area and an electron transmission area, are recombined to generate excitons, then release energy, the excitons migrate under the action of the electric field, the energy is transferred to a luminescent substance in the light-emitting area, electrons in molecules of the luminescent substance are excited to transit from a ground state to an excited state, and when the electrons return to the ground state from the excited state, the energy is released in a light mode, so that a light-emitting phenomenon is generated.
The hole transport region mainly plays a role in injecting and transporting holes, and comprises a hole injection layer, a hole transport layer, a light emitting auxiliary layer and the like. The hole transport materials should generally have high hole mobility, good thermal stability, good film formation, suitable Highest Occupied Molecular Orbital (HOMO) and triplet energy level (T1). Aromatic amine compounds are one of the most widely used hole transport materials in the OLED field at present, but aromatic amine compounds of different structures are different in performance. For example, the difference in groups directly attached to N can produce different degrees of electron effects (including both inductive and conjugated effects) that result in different hole transport capacities, HOMO and T1 values for the compounds.
Disclosure of Invention
The present invention provides an arylamine compound having high hole mobility, good thermal stability, excellent film forming property, HOMO and T1 values matched with a light-emitting layer, and having a structure represented by formula (I):
wherein X is selected from oxygen atom or sulfur atom;
the L is 1 ～L 6 Independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
ar as described 1 ～Ar 4 At least one of the substituents containing aliphatic rings is selected from one of the substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups：
Wherein e is selected from the integers of 0-2, f is selected from the integers of 0-3, g is selected from the integers of 0-4, h is selected from the integers of 0-6, i is selected from the integers of 0-8, j is selected from the integers of 0-10, and k is selected from the integers of 0-1;
said R is 21 、R 22 Independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a cyclobutane group, a deuterated cyclobutane group, a cyclopentane group, a deuterated cyclopentane group, a cyclohexane group, a deuterated cyclohexane group, a cycloheptane group, a deuterated cycloheptane group, a norbornane group, a deuterated norbornane group, a one of adamantyl, deuterated adamantyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthryl, deuterated anthryl, phenanthryl, deuterated phenanthryl, triphenylyl, deuterated triphenylenyl, pyrenyl, deuterated pyrenyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirobifluorenyl, deuterated spirobifluorenyl, when there are a plurality of R 21 Or R is 22 When a plurality of R 21 The same or different, a plurality of R 22 The same or different;
m is selected from integers of 0-3, and n is selected from integers of 0-4;
said R is a 、R b Independently selected from hydrogen atomsDeuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C1-C4 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, when a plurality of R's are present a Or R is b When a plurality of R a The same or different, a plurality of R b The same or different.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, and the hole transmission region contains one or more than one of the aromatic amine compounds.
The beneficial effects are that:
the arylamine compound of the formula (I) provided by the invention has good hole mobility, has more proper HOMO and T1 values relative to other functional layers, especially a luminescent layer, is a hole transport material with excellent performance, especially when being used as a luminescent auxiliary layer, can well prevent excitons from migrating to the luminescent layer and a hole transport region, thereby avoiding interface luminescence between the luminescent layer and the hole transport region, and effectively improving the driving voltage and the luminous efficiency of the device. The arylamine compound has high glass transition temperature (Tg), good thermal stability and good film forming property, and meanwhile, when the arylamine compound is used as a light-emitting auxiliary layer, the interface between the light-emitting layer and the hole transport region can be effectively prevented from emitting light, so that the heat aging speed of an organic material (especially a hole transport material) due to interface light emission is reduced, and the service life of the device is prolonged.
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 present specification, when substitutedWhere the position of the base on the aromatic ring is not fixed, this means that it can be attached to any of the corresponding selectable positions of the aromatic ring. For example, the number of the cells to be processed,can indicate->And so on.
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, or a tert-butyl group.
Cycloalkyl as used herein refers to a hydrocarbon group having at least one hydrogen atom in the cycloalkyl molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 3 to 6 carbon atoms, and examples may include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, and the like. The alkyl group is preferably a cyclopentylalkyl group, a cyclohexenyl group, a 1-adamantyl group, a 2-adamantyl group, or a norbornyl group.
Aryl in the present invention refers to the generic term for monovalent radicals remaining after removal of one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic aryl, polycyclic aryl or fused ring aryl, preferably having from 6 to 25 carbon atoms, more preferably from 6 to 20 carbon atoms, particularly preferably from 6 to 14 carbon atoms, and most preferably from 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, but not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirobifluorenyl, and the like. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthryl group (preferably a 2-anthryl group), a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylenyl group, or a spirobifluorenyl group.
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 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, polycyclic heteroaryl or fused ring heteroaryl. 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 arylene group according to the present invention refers to the generic term for divalent radicals remaining after removal of two hydrogen atoms from the aromatic nucleus carbon of an aromatic compound molecule, which may be a monocyclic arylene group, a polycyclic arylene group, a fused ring arylene group, or a combination thereof, 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 arylene group includes phenylene and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, phenylene-naphthylene, naphthylene-naphthylene, phenylene-fluorenylene-phenylene, phenylene-helicoylene-phenylene, and the like, but is not limited thereto; the condensed ring arylene includes, but is not limited to, naphthylene, anthrylene, phenanthrylene, fluorenylene, pyreylene, triphenylene, fluoranthrylene, benzofluorenylene, and the like. The arylene group is preferably phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, benzofluorenylene, or phenylene-fluorenylene.
Heteroaryl, as used herein, refers to the generic term for groups in which one or more of the aromatic nucleus carbons in the arylene group is replaced with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, the heteroarylene group may be attached at a ring-forming carbon atom or at a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused ring heteroarylene group. The monocyclic heteroarylene group includes, but is not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thienyl group, and the like; the polycyclic heteroarylene group includes bipyridylene group, bipyrimidiylene group, phenylpyridylene group, etc., but is not limited thereto; the condensed ring heteroarylene group includes quinolinylene, isoquinolylene, indolylene, benzothienyl, benzofuranylene, benzoxazolylene, benzimidazolylene, benzothiazolylene, dibenzofuranylene, benzodibenzofuranylene, dibenzothiophenylene, benzodithiorenylene, carbazolylene, benzocarbazolylene, acridinylene, 9, 10-dihydroacridinylene, phenoxazinylene, phenothiazinylene, phenoxazinylene, and the like, but is not limited thereto. The heteroaryl group is preferably a pyridyl group, a pyrimidylene group, a thienyl group, a furanylene group, a benzothienyl group, a benzofuranylene group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzodibenzothiophenyl group, a benzodibenzofuranyl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.
Alkoxy according to the present invention means-O-alkyl, wherein said alkyl is as defined previously.
The alkenyl group as used herein refers to a hydrocarbon group such as vinyl, styryl, etc. which is formed by removing one hydrogen atom from an olefin molecule, but is not limited thereto.
The alkynyl refers to a hydrocarbon group formed by removing one hydrogen atom from an alkyne molecule, such as ethynyl, phenylethynyl and the like, but is not limited thereto.
The alicyclic ring in the present invention refers to a cyclic hydrocarbon having aliphatic nature, and the molecule contains a closed carbocycle, which may be a monocyclic hydrocarbon formed by 3 to 18 carbon atoms, preferably 3 to 12 carbon atoms, more preferably 3 to 7 carbon atoms, and may be completely unsaturated or partially unsaturated, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but is not limited thereto. The plurality of monocyclic hydrocarbons may also be linked in a variety of ways: two rings in the molecule can share one carbon atom to form a spiro ring; the two carbon atoms on the ring can be connected by a carbon bridge to form a bridge ring; several rings may also be interconnected to form a cage-like structure.
The aromatic ring in the present invention means aromatic hydrocarbon, which may be monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon, and benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, etc., may be mentioned, but is not limited thereto.
"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 C1-C30 alkenyl group, substituted or unsubstituted C1-C30 alkynyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C2-C60 heteroaryl group, preferably deuterium atom, halogen atom, cyano group, nitro group, C1-C12 alkyl group, C1-C12 alkenyl group, C1-C12 alkynyl group, C1-C12 alkoxy group, C3-C12 cycloalkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, in the case of being substituted with a plurality of substituents, the plurality of substituents are the same or different from each other; preferably, it means not substituted or substituted with one or more substituents selected from the group consisting of: deuterium, fluorine, chlorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, vinyl, methoxy, ethoxy, phenyl, pentadeuterophenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, dibenzofuranyl, dibenzothiophenyl, phenylcarbazolyl, where the substituents are substituted with the substituents are the same or different from each other.
The term "integer selected from 0 to M" as used herein means any one of the integers selected from 0 to M, including 0,1,2 … M-2, M-1, M. For example, "e, b, r" as described herein is selected from 0 toThe integer of 2 means that e, b, r are selected from 0,1 or 2, said "f, m, c, d 1 P is an integer of 0 to 3, which means f, m, c, d 1 P is selected from 0,1,2 or 3, said "g, n, a, a 1 Q is an integer from 0 to 4, which means g, n, a, a 1 Q is selected from 0,1,2,3 or 4, said "h, b 1 An integer "selected from 0 to 6 means h, b 1 Selected from 0,1,2,3,4,5 or 6, said "i, c 1 An integer "selected from 0 to 8 means e, c 1 Selected from 0,1,2,3,4,5,6,7 or 8, wherein "j is an integer from 0 to 10" means that f is selected from 0,1,2,3,4,5,6,7,8,9 or 10, wherein "k, d is an integer from 0 to 1" means that k, d is selected from 0 or 1, and wherein "l is an integer from 0 to 5" means that l is selected from 0,1,2,3,4 or 5; and so on.
The term "bonded to form a cyclic structure" as used herein means that two groups are attached to each other by a chemical bond and optionally aromatized. As exemplified below:
in the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a condensed ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclopentane, cyclohexane acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto. Wherein the five-membered ring or six-membered ring may refer to a ring formed by two groups (such as phenyl) and the attached groups/fragments, or may refer to a ring formed by two groups (such as ethyl) themselves and the attached groups/fragments.
The invention provides an arylamine compound, which has a structure shown in a formula (I):
wherein X is selected from oxygen atom or sulfur atom;
the L is 1 ～L 6 Independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
ar as described 1 ～Ar 4 At least one of the substituents containing an aliphatic ring is selected from one of the following, and the rest is independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl:
wherein e is selected from the integers of 0-2, f is selected from the integers of 0-3, g is selected from the integers of 0-4, h is selected from the integers of 0-6, i is selected from the integers of 0-8, j is selected from the integers of 0-10, and k is selected from the integers of 0-1;
said R is 21 、R 22 Independently selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a cyclobutane group, a deuterated cyclobutane group, a cyclopentane group, a deuterated cyclopentane group, a cyclohexane group, a deuterated cyclohexane group, a cycloheptane group, a deuterated cycloheptane group, a norbornane group, a deuterated norbornane group, a one of adamantyl, deuterated adamantyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthryl, deuterated anthryl, phenanthryl, deuterated phenanthryl, triphenylyl, deuterated triphenylenyl, pyrenyl, deuterated pyrenyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirobifluorenyl, deuterated spirobifluorenyl, when there are a plurality of R 21 Or R is 22 When a plurality of R 21 The same or different, a plurality of R 22 The same or different;
m is selected from integers of 0-3, and n is selected from integers of 0-4;
said R is a 、R b Independently 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 C1-C4 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, when a plurality of R's are present a Or R is b When a plurality of R a The same or different, a plurality of R b The same or different.
Preferably, the "heteroaryl" contains at least one heteroatom as described below: oxygen atom, sulfur atom, nitrogen atom, silicon atom.
Preferably, the substituents in the above "substituted or unsubstituted" are independently selected from the group consisting of a deuterium atom, fluorine atom, cyano group, methyl group, deuteromethyl group, ethyl group, deuteroethyl group, n-propyl group, deutero-n-propyl group, isopropyl group, deutero-isopropyl group, n-butyl group, deutero-n-butyl group, sec-butyl group, deutero-sec-butyl group, isobutyl group, deutero-isobutyl group, tert-butyl group, deutero-tert-butyl group, cyclopropanyl group, deutero-cyclopropanyl group, cyclobutylalkyl group, deutero-cyclobutylalkyl group, cyclopentanyl group, cyclohexylalkyl group, deutero-cyclohexylalkyl group, cycloheptyl group, deutero-cycloheptyl group, norbornyl group, deutero-norbornyl group, adamantyl group, deutero-adamantyl group, vinyl group, methoxy group, ethoxy group, phenyl group, deutero-phenyl group, naphthyl group, anthracenyl group, deutero-anthracenyl group, phenanthrenyl group, deutero-phenanthrenyl group, triphenylenyl group, deutero-triphenylenyl group, pyrenyl group, deutero-pyrenyl group, pyridinyl group, triazinyl group, pyrazinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazoline group, quinoxalinyl group, dibenzo-9-dibenzo-phenylfluorenyl group, 9-dibenzo group, 9-dibenzofluorenyl group, and 9-dibenzofluorenyl group, 9-substituted by a plurality of substituents selected from the same group, and 9-substituted groups.
Preferably, said L 1 ～L 6 Independently selected from one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophene group, and a substituted or unsubstituted carbazole group.
Preferably, said L 1 ～L 6 Independently selected from a single bond or one of the substituents shown below:
wherein a is selected from integers of 0-4, b is selected from integers of 0-2, c is selected from integers of 0-3, and d is selected from integers of 0-1;
said R is 11 One selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuteromethyl group, an ethyl group, a deuteroethyl group, an n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, an n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a methoxy group, an ethoxy group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, an anthracenyl group, a deuterated anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a deuterated triphenylenyl group, a pyrenyl group, a deuterated pyrenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a phenylcarbazolyl group, a deuterated phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a deuterated 9-diphenylfluorenyl group, a deuterated 9-diphenylfluorenyl group, a spirodibenzofluorenyl group, and a deuterated spirodibenzofluorenyl group, when a plurality of R's exist 11 When a plurality of R 11 The same or different;
said R is 12 、R 13 、R 18 Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl and deuterated naphthyl; when R is 12 And R is R 13 When independently selected from one of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl species, R 12 And R is R 13 Can be connected to form a substituted or unsubstituted C3-C7 aliphatic ring; when R is 12 And R is R 13 R when independently selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl 12 And R is R 13 Can be linked to form a five membered carbocyclic ring;
said R is 14 One selected from phenyl, deuterated phenyl, naphthyl and deuterated naphthyl;
said R is 15 、R 16 、R 17 Independently selected from one of phenylene, deuterated phenyl, naphthylene, deuterated naphthylene;
when R is 18 R is selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl 17 And R is R 18 Can be linked to form a five membered carbocyclic ring.
Preferably, said L 1 ～L 6 Independently selected from a single bond or one of the substituents shown below:
wherein, a is as follows 1 An integer selected from 0 to 4, b 1 An integer selected from 0 to 6, said c 1 An integer selected from 0 to 8, d 1 An integer selected from 0 to 3.
Preferably, said L 1 ～L 6 Independently selected from single bonds orOne of the substituents shown below:
preferably, said Ar 1 ～Ar 4 At least one of the substituents is selected from one of the following:
preferably Ar, not selected from the alicyclic-containing substituents 1 ～Ar 4 Independently selected from one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted spirofluorenyl group.
Preferably, said Ar is not selected from the group consisting of said alicyclic-containing substituents 1 ～Ar 4 The groups are independently selected from one of the substituents shown below:
wherein l is selected from integers of 0-5, p is selected from integers of 0-3, q is selected from integers of 0-4, and r is selected from integers of 0-2;
Said R is 31 Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-propyl groupButyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, cyclopropane, deuterated cyclopropane, cyclobutane, deuterated cyclobutane, cyclopentane, deuterated cyclopentane, cyclohexenyl, deuterated cyclohexenyl, cycloheptane, deuterated cycloheptane, norbornane, deuterated norbornane, adamantyl, deuterated adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylene, deuterated triphenylene, pyrenyl, deuterated pyrenyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirodibenzofluorenyl, and one or more of the following R groups exist 31 When a plurality of R 31 The same or different, or any two adjacent groups are connected to form a substituted or unsubstituted C6-C10 aromatic ring;
said R is 32 One selected from phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl and deuterated biphenyl;
said R is 33 、R 34 、R 36 Independently selected from a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group and a deuterated naphthyl group; when R is 33 And R is R 34 When independently selected from one of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, R 33 And R is R 34 Can be connected to form a substituted or unsubstituted C3-C7 aliphatic ring; when R is 33 And R is R 34 Independently selected from phenyl groupsR in the case of one of deuterated phenyl, naphthyl and deuterated naphthyl 33 And R is R 34 Can be linked to form a five membered carbocyclic ring;
said R is 35 、R 37 Independently selected from one of phenylene, deuterated phenyl, biphenylene, deuterated biphenylene, naphthylene and deuterated naphthylene.
Preferably, said Ar is not selected from the group consisting of said alicyclic-containing substituents 1 ～Ar 4 The groups are independently selected from one of the substituents shown below:
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preferably, the aromatic amine compound has one of structures represented by formulas (II-A) to (II-F):
wherein, the L 3 ～L 6 、Ar 1 ～Ar 4 X is as described above.
Preferably, the aromatic amine compound has one of structures represented by formulas (III-a) to (III-P):
wherein, the L 3 ～L 6 、Ar 1 ～Ar 4 X is as described above.
Preferably, the aromatic amine compound has one of structures represented by formulas (IV-Sup>A) to (IV-F):
wherein, the L 3 ～L 6 、Ar 1 ～Ar 4 X is as described above.
Preferably, the aromatic amine compound has one of structures represented by formulas (V-Sup>A) to (V-F):
wherein, the L 3 ～L 6 、Ar 1 ～Ar 4 X is as described above.
Preferably, said Ar 1 ～Ar 4 Is selected from the group consisting of the alicyclic-containing substituents.
Preferably, said Ar 1 ～Ar 4 Is selected from the group consisting of the alicyclic-containing substituents.
Preferably, said Ar 1 ～Ar 4 Is selected from the group consisting of the alicyclic-containing substituents.
Preferably, said Ar 1 ～Ar 4 Are selected from the alicyclic-containing substituents.
Preferably, in said Ar which is not selected from said alicyclic-containing substituent 1 ～Ar 4 At least one substituent selected from the following groups:
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most preferably, the aromatic amine compound is selected from one of the following compounds:
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the above only shows some specific structural forms of the compound shown in the formula (I), but the invention is not limited to the chemical structures, and substituents are contained in the compound based on the formula (I).
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, and the hole transmission region contains one or more than one of the aromatic amine compounds.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transmission region, a luminescent layer and an electron transmission region, the hole transmission region comprises at least one layer of a hole injection layer, a hole transmission layer and a luminescent auxiliary layer, and the hole transmission region contains one or more than one of the aromatic amine compounds.
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, axial vinyl 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' -tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT/PSS), and arylamine compounds according to the present invention may be used, but are not limited thereto. Preferably, the hole injection layer is a single-layer structure composed of two substances, namely a matrix material and a doping material, and more preferably the mass ratio of the matrix material to the doping material is 100:1-100:10.
The invention is characterized in thatThe hole transport layer 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 derivatives in which two or more triarylamine structures are linked by a single bond or arylene group can be used, as well as other hole mobilities of 10 -6 cm 2 Examples of the "substance" 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), and arylamine compounds of the present invention.
The light-emitting auxiliary layer according to the present invention may have a single layer structure formed of a single substance, or may have a single layer structure or a multilayer structure formed of different substances, and it is possible to use a triarylamine derivative, a spirofluorene derivative, a dibenzofuran derivative, and other substances having appropriate energy levels of HOMO and T1, in which two or more triarylamine structures are linked by a single bond or arylene group, for example, 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-bis ([ 1,1' -biphenyl ] -4-yl) -3'- (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, the aromatic amine compounds of the present invention, but are not limited thereto.
Preferably, the hole transport region includes a hole injection layer containing one or more of the aromatic amine compounds of the present invention.
Preferably, the hole transport region includes a hole transport layer containing one or more of the aromatic amine compounds of the present invention.
Preferably, the hole transport region includes a light-emitting auxiliary layer containing one or more of the aromatic amine compounds of the present invention.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode, an organic layer between the anode and the cathode, and a covering layer arranged on one side of the cathode away from the anode, wherein the covering layer contains one or more than one of the aromatic amine compounds.
The covering layer comprises a first covering layer and/or a second covering layer, and when the covering layer comprises the first covering layer or the second covering layer, the covering layer can be a single-layer structure formed by a single substance or a single-layer structure formed by different substances; when included, the first cover layer and the second cover layer are a single substance or a multi-layer structure of different substances. The material for the cover layer may be organic or inorganic, and preferably an arylamine compound according to the present invention is used.
The aromatic amine compound shown in the formula (I) can be prepared by the following synthetic route:
Wherein the X is 1 、X 2 Independently selected from chlorine, bromine or iodine atoms, said X, L 1 ～L 6 、R a 、R b 、Ar 1 ～Ar 4 And m and n are as described above.
Compound (Y) 1 ) With a compound (Y) 2 ) Compound (Y) 3 ) The arylamine compound shown in the formula (I) can be obtained through one-step or two-step Buchwald reaction. Compound (Y) 1 ) Can be combined with the compound (Y) 2 ) The reaction may be carried out with the compound (Y) 3 ) In the case where the compound (Y2) is the same as the compound (Y3), the reaction may be carried out in one step, and the reaction conditions such as a reaction solvent, a catalyst, a ligand, a base, etc. may be any conventional method without particular limitation. The preparation method has the advantages of easily available raw materials, simple preparation process and excellent reaction yield.
The light-emitting layer of the present invention may contain only a guest material, or may be dispersed in a host material using a guest material. As the guest material, a fluorescent compound such as pyrene derivative, fluoranthene derivative, aromatic amine derivative, etc. can be used, and specifically, 10- (2-benzothiazolyl) -2,3,6, 7-tetrahydro can be exemplified-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 ]Biphenyl (DPAVBi), etc.; phosphorescent materials such as iridium complex, osmium complex, platinum complex, and the like can also be used, and specifically, bis (4, 6-difluorophenylpyridine-N, C2) iridium picolinate (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 a zinc complex, a heterocyclic compound such as an oxadiazole derivative or a benzimidazole derivative, a condensed aromatic compound such as a carbazole derivative or an anthracene derivative, or an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, and specifically, 8-hydroxyquinoline aluminum (Alq) 3 ) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), TPD, 4' -bis (9-Carbazole) Biphenyl (CBP), 4' -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (2-naphthyl) Anthracene (ADN), and the like.
The electron transport region comprises 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. Specifically, 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.
The electron transport layer of the invention can be a single layerThe single-layer structure of one substance may be a single-layer structure or a multi-layer structure of a different substance, and aluminum complex, beryllium complex, zinc complex, imidazole derivative, benzimidazole derivative, carbazole derivative, phenanthroline derivative, polymer compound, etc. having high electron-transporting property, for example, alq may be used 3 Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq 2 ) BAlq, 2- (4-biphenyl) -5-Phenyloxadiazole (PBD), and the like.
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 or more, which facilitates electron transport, preferably triazine derivatives, azabenzene derivatives, and the like. Most preferred are triazine derivatives.
Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer;
preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer;
preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer and an electron injection layer;
preferably, the organic layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
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, and also can be a transparent or semitransparent layer structure with high work function, such as Indium Tin Oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO) and Aluminum Zinc Oxide (AZO)Indium Gallium Oxide (IGO), indium oxide (In) 2 O 3 ) Or tin oxide (SnO) 2 ) And (3) forming a layer structure.
The cathode of the invention can be a thin film with low work function made of lithium, calcium, lithium fluoride/aluminum, silver, magnesium silver alloy and the like, and can be made into a reflecting electrode, a transparent electrode or a semitransparent electrode by adjusting the thickness of the film.
The organic layers, cathode, anode and cover layer can be prepared by any one 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.
The thickness of each organic layer and the cover 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 OLED illumination field and the OLED display field, and can be specifically exemplified as a smart phone display screen, a tablet computer display screen, an intelligent wearable device display screen, a television and other large-size displays, VR, automobile tail lights 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: preparation of Compounds m-15, m-16, m-17, m-18, m-19
Under the protection of nitrogenInto a three-necked flask, compound a-1 (10.56 g,60 mmol), b-1 (10.32 g,60 mmol) and K were sequentially added 2 CO 3 (16.58g,120mmol)、Pd(PPh 3 ) 4 (1.38 g,1.2 mmol) of a toluene/ethanol/water (3:1:1) mixed solvent was added, and the mixture was stirred, and the above-mentioned reactant system was heated under reflux for 8 hours. After the completion of the reaction, the mixture was cooled to room temperature, extracted with deionized water and toluene to give an organic layer, which was washed 3 times with 400mL of deionized water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to give compound m-15 (10.45 g, yield 78%). Mass spectrum m/z:223.1376 (theory: 223.1361).
The compounds m-16, m-17, m-18 and m-19 can be prepared by replacing the raw materials a and b in equimolar amounts according to the preparation method of the compound m-15, and the yield and mass spectrum are shown in the table 1:
TABLE 1
Synthesis example 2: preparation of Compounds Y2, Y3
To a three-necked flask, toluene (300 mL), compound m-1 (4.42 g,30 mmol), compound n-1 (6.21 g,30 mmol), palladium acetate (0.10 g,0.45 mmol), sodium t-butoxide (5.77 g,60 mmol) and tri-t-butylphosphine (4 mL of toluene solution) were sequentially added under nitrogen. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give compound Y2-1 (6.81 g, yield 83%). Mass spectrum m/z:273.1536 (theory: 273.1517).
The other Y2 and Y3 compounds can be prepared by replacing the compounds m and n in equimolar quantity according to the preparation method of the compound Y2-1, and the yield and mass spectrum are shown in the table 2:
TABLE 2
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Synthesis example 3: preparation of Compound 15
To a three-necked flask, toluene (100 mL), compound Y1-1 (3.73 g,10 mmol), compound Y2-1 (2.73 g,10 mmol), palladium acetate (0.03 g,0.15 mmol), sodium t-butoxide (1.92 g,20 mmol), and tri-t-butylphosphine (1.3 mL of toluene solution) were successively added under nitrogen. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give intermediate Z-1 (4.04 g, 78% yield), mass spectrum m/Z:517.1060 (theory: 517.1041).
To a three-necked flask, toluene (50 mL), intermediate Z-1 (2.59 g,5 mmol), compound Y3-1 (1.48 g,5 mmol), palladium acetate (0.02 g,0.08 mmol), sodium t-butoxide (0.96 g,10 mmol) and tri-t-butylphosphine (0.7 mL of toluene solution) were sequentially added under nitrogen. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give compound 15 (2.71 g, yield 74)% of the solid, HPLC detection of > 99.6%. Mass spectrum m/z:732.3156 (theory: 732.3141). Theoretical element content (%) C 54 H 40 N 2 O: c,88.49; h,5.50; n,3.82. Measured element content (%): c,88.46; h,5.52; n,3.84.
Synthesis example 4: preparation of Compound 32
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-2, Y2-2, Y3-2 and Z-2, and the other steps were the same, to obtain compound 32 (2.75 g), and the purity of the solid was not less than 99.5% by HPLC detection. Mass spectrum m/z:722.2739 (theory: 722.2756). Theoretical element content (%) C 52 H 38 N 2 S: c,86.39; h,5.30; n,3.87. Measured element content (%): c,86.36; h,5.36; n,3.85.
Synthesis example 5: preparation of Compound 52
Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y2-3, Y3-3 and Z-3, and the other steps were the same, to obtain Compound 52 (3.14 g), and the purity of the solid was. Mass spectrum m/z:814.3026 (theory: 814.3018). Theoretical element content (%) C 58 H 42 N 2 OS: c,85.47; h,5.19; n,3.44. Measured element content (%): c,85.49; h,5.13; n,3.45.
Synthesis example 6: preparation of Compound 69
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-2, Y2-4, Y3-4 and Z-4, and the other steps were the same to obtain a compound69 (3.30 g) and the purity of the solid detected by HPLC was ≡ 99.7%. Mass spectrum m/z:814.3039 (theory: 814.3018). Theoretical element content (%) C 58 H 42 N 2 OS: c,85.47; h,5.19; n,3.44. Measured element content (%): c,85.45; h,5.24; n,3.41.
Synthesis example 7: preparation of Compound 76
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-3, Y2-5, Y3-5 and Z-5, and the other steps were the same, to obtain compound 76 (3.19 g), and the purity of the solid was not less than 99.3% by HPLC detection. Mass spectrum m/z:898.4126 (theory: 898.4135). Theoretical element content (%) C 65 H 34 D 12 N 2 S: c,86.82; h,6.50; n,3.12. Measured element content (%): c,86.85; h,6.43; n,3.16.
Synthesis example 8: preparation of Compound 87
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-4, Y2-6, Y3-6 and Z-6, and the other steps were the same, to obtain compound 87 (3.41 g), and the purity of the solid was not less than 99.5% by HPLC detection. Mass spectrum m/z:873.1136 (theory: 873.1120). Theoretical element content (%) C 65 H 48 N 2 O: c,89.42; h,5.54; n,3.21. Measured element content (%): c,89.43; h,5.59; n,3.15.
Synthesis example 9: preparation of Compound 88
Y1-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equal molar amounts of Y1-5, Y3-7 and Z-7, and the other steps were the sameCompound 88 (3.45 g) was obtained, and the purity of the solid was ≡ 99.2% by HPLC. Mass spectrum m/z:920.3754 (theory: 920.3767). Theoretical element content (%) C 69 H 48 N 2 O: c,89.97; h,5.25; n,3.04. Measured element content (%): c,89.96; h,5.29; n,3.02.
Synthesis example 10: preparation of Compound 102
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-6, Y2-4, Y3-4 and Z-24, and the other steps were the same, to obtain compound 102 (3.06 g), and the purity of the solid was not less than 99.5% by HPLC detection. Mass spectrum m/z:814.3027 (theory: 814.3018). Theoretical element content (%) C 58 H 42 N 2 OS: c,85.47; h,5.19; n,3.44. Measured element content (%): c,85.49; h,5.13; n,3.47.
Synthesis example 11: preparation of Compound 154
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-6, Y2-4, Y3-8 and Z-8, and the other steps were the same, to obtain compound 154 (3.46 g), and the purity of the solid was not less than 99.4% by HPLC detection. Mass spectrum m/z:864.3189 (theory: 864.3174). Theoretical element content (%) C 62 H 44 N 2 OS: c,86.08; h,5.13; n,3.24. Measured element content (%): c,86.04; h,5.15; n,3.27.
Synthesis example 12: preparation of Compound 200
Y1-1, Y2-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-7, Y2-7 and Z-9The procedure is the same, and compound 200 (2.96 g) is obtained with a purity of > 99.1% as measured by HPLC. Mass spectrum m/z:822.3259 (theory: 822.3246). Theoretical element content (%) C 60 H 42 N 2 O 2 : c,87.56; h,5.14; n,3.40. Measured element content (%): c,87.51; h,5.17; n,3.42.
Synthesis example 13: preparation of Compound 228
Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with Y2-8, Y3-9 and Z-10 in equimolar amounts, and the other steps were the same, to obtain compound 228 (3.35 g), and the purity of the solid was. Mass spectrum m/z:892.4376 (theory: 892.4393). Theoretical element content (%) C 66 H 56 N 2 O: c,88.75; h,6.32; n,3.14. Measured element content (%): c,88.71; h,6.38; n,3.11.
Synthesis example 14: preparation of Compound 279
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-8, Y2-9, Y3-10 and Z-11, and the other steps were the same, to obtain compound 279 (3.17 g), and the purity of the solid was not less than 99.1% by HPLC detection. Mass spectrum m/z:866.3680 (theory: 866.3695). Theoretical element content (%) C 63 H 50 N 2 S: c,87.26; h,5.81; n,3.23. Measured element content (%): c,87.28; h,5.88; n,3.16.
Synthesis example 15: preparation of Compound 286
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with Y in equimolar amounts1-9, Y2-10, Y3-11, Z-12, the other steps were identical, giving compound 286 (2.72 g), purity of the solid > 99.3% by HPLC. Mass spectrum m/z:810.3627 (theory: 810.3610). Theoretical element content (%) C 60 H 46 N 2 O: c,88.86; h,5.72; n,3.45. Measured element content (%): c,88.83; h,5.78; n,3.41.
Synthesis example 16: preparation of Compound 315
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-5, Y2-9, Y3-12 and Z-13, and the other steps were the same, to obtain compound 315 (3.06 g), and the purity of the solid was not less than 99.7% by HPLC detection. Mass spectrum m/z:860.3419 (theory: 860.3403). Theoretical element content (%) C 63 H 44 N 2 O 2 : c,87.88; h,5.15; n,3.25. Measured element content (%): c,87.87; h,5.20; n,3.23.
Synthesis example 17: synthesis of Compound 381
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-2, Y2-20, Y3-18 and Z-22, and the other steps were the same, to obtain a compound 381 (3.46 g), and the purity of the solid was ≡ 99.2% by HPLC detection. Mass spectrum m/z:946.5275 (theory: 946.5260). Theoretical element content (%) C 68 H 70 N 2 S: c,86.21; h,7.45; n,2.96. Measured element content (%): c,86.24; h,7.40; n,2.97.
Synthesis example 18: synthesis of Compound 398
Y2-1 and Y3 in Synthesis example 31. Z-1 was replaced with Y2-21, Y3-19 and Z-23 in equal molar amounts in the same manner, and compound 398 (2.83 g) was obtained in the same manner, and the purity of the solid was not less than 99.0% by HPLC detection. Mass spectrum m/z:807.3317 (theory: 807.3332). Theoretical element content (%) C 57 H 37 D 5 N 2 OS: c,84.72; h,5.86; n,3.47. Measured element content (%): c,84.70; h,5.91; n,3.45.
Synthesis example 19: preparation of Compound 408
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-4, Y2-11, Y3-3 and Z-14, and the other steps were the same, to obtain compound 408 (3.03 g), and the purity of the solid was not less than 99.8% by HPLC detection. Mass spectrum m/z:840.3183 (theory: 840.3174). Theoretical element content (%) C 60 H 44 N 2 OS: c,85.68; h,5.27; n,3.33. Measured element content (%): c,85.63; h,5.30; n,3.35.
Synthesis example 20: preparation of Compound 427
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-10, Y2-12, Y3-3 and Z-15, and the other steps were the same, to obtain a compound 427 (2.96 g), and the purity of the solid was not less than 99.5% by HPLC detection. Mass spectrum m/z:870.3657 (theory: 870.3644). Theoretical element content (%) C 62 H 50 N 2 OS: c,85.48; h,5.79; n,3.22. Measured element content (%): c,85.49; h,5.73; n,3.26.
Synthesis example 21: preparation of Compound 439
To a three-necked flask, toluene (50 mL), compound Y1-11 (1.63 g,5 mmol), compound Y2-4 (2.99 g,10 mmol), palladium acetate (0.04 g,0.16 mmol), sodium t-butoxide (1.92 g,20 mmol), and tri-t-butylphosphine (1.4 mL of toluene solution) were sequentially added under nitrogen. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, suction filtered and rinsed with methanol to give compound 439 (3.13 g, 82% yield) as a recrystallized solid with purity ≡ 99.8% by HPLC. Mass spectrum m/z:762.3602 (theory: 762.3610). Theoretical element content (%) C 56 H 46 N 2 O: c,88.15; h,6.08; n,3.67. Measured element content (%): c,88.11; h,6.06; n,3.70.
Synthesis example 22: preparation of Compound 464
Y1-11 and Y2-4 in Synthesis example 21 were successively replaced with Y1-12 and Y2-13 in equimolar amounts, and the procedure was the same, except that compound 464 (3.25 g) was obtained, and the purity of the solid was ≡ 99.4% by HPLC detection. Mass spectrum m/z:822.2719 (theory: 822.2739). Theoretical element content (%) C 56 H 42 N 2 OS 2 : c,81.72; h,5.14; n,3.40. Measured element content (%): c,81.70; h,5.18; n,3.39.
Synthesis example 23: preparation of Compound 525
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-8, Y2-14, Y3-13 and Z-16, and the other steps were the same, to obtain compound 525 (3.01 g), and the purity of the solid was not less than 99.3% by HPLC detection. Mass spectrum m/z:792.2825 (theory: 792.2810). Theoretical element content (%) C 55 H 40 N 2 O 2 S: c,83.30; h,5.08; n,3.53. Content of measured element(％)：C,83.36；H,5.03；N,3.51。
Synthesis example 24: preparation of Compound 530
The procedure was otherwise identical except that Y1-11 and Y2-4 in Synthesis example 21 were successively replaced with equimolar amounts of Y1-13 and Y2-15 to give Compound 530 (3.46 g), and the purity of the solid was ≡ 99.5% by HPLC detection. Mass spectrum m/z:886.4337 (theory: 886.4321). Theoretical element content (%) C 64 H 58 N 2 S: c,86.64; h,6.59; n,3.16. Measured element content (%): c,86.62; h,6.64; n,3.13.
Synthesis example 25: preparation of Compound 537
The procedure was otherwise identical except that Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y2-16, Y3-3 and Z-17 to give compound 537 (3.58 g) having a purity of not less than 99.8% as measured by HPLC. Mass spectrum m/z:894.3599 (theory: 894.3582). Theoretical element content (%) C 64 H 42 D 4 N 2 OS: c,85.87; h,5.63; n,3.13. Measured element content (%): c,85.84; h,5.69; n,3.10.
Synthesis example 26: preparation of Compound 544
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-14, Y2-17, Y3-14 and Z-18, and the other steps were the same, to obtain compound 544 (3.26 g), and the purity of the solid was not less than 99.4% by HPLC detection. Mass spectrum m/z:869.3475 (theory: 869.3488). Theoretical element content (%) C 62 H 39 D 5 N 2 OS：C,85.58；H,5.68；N,3.22. Measured element content (%): c,85.59; h,5.72; n,3.20.
Synthesis example 27: preparation of Compound 546
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-6, Y2-18, Y3-15 and Z-19, and the other steps were the same, to obtain compound 546 (3.07 g), and the purity of the solid was not less than 99.1% by HPLC. Mass spectrum m/z:864.3185 (theory: 864.3174). Theoretical element content (%) C 62 H 44 N 2 OS: c,86.08; h,5.13; n,3.24. Measured element content (%): c,86.02; h,5.18; n,3.27.
Synthesis example 28: synthesis of Compound 563
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-6, Y2-19, Y3-16 and Z-20, and the other steps were the same, to obtain compound 563 (3.16 g), and the purity of the solid was ≡ 99.2% by HPLC detection. Mass spectrum m/z:878.3350 (theory: 878.3331). Theoretical element content (%) C 63 H 46 N 2 OS: c,86.07; h,5.27; n,3.19. Measured element content (%): c,86.09; h,5.22; n,3.22.
Synthesis example 29: synthesis of Compound 599
Y1-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-15, Y3-17 and Z-21, and the other steps were the same, to obtain Compound 599 (3.33 g), and the purity of the solid was not less than 99.7% by HPLC. Mass spectrum m/z:864.3156 (theory: 864.3174). Theoretical element content (%) C 62 H 44 N 2 OS: c,86.08; h,5.13; n,3.24. Measured element content (%): c,86.05; h,5.19; n,3.20.
Synthesis example 30: synthesis of Compound 610
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-6, Y2-22, Y3-10 and Z-25, and the other steps were the same, to obtain compound 610 (3.12 g), and the purity of the solid was not less than 99.6% by HPLC detection. Mass spectrum m/z:878.3680 (theory: 878.3695). Theoretical element content (%) C 64 H 50 N 2 S: c,87.43; h,5.73; n,3.19. Measured element content (%): c,87.46; h,5.77; n,3.11.
Synthesis example 31: synthesis of Compound 611
Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were successively replaced with equimolar amounts of Y1-4, Y2-23, Y3-17 and Z-26, and the other steps were the same, to obtain compound 611 (2.92 g), and the purity of the solid was ≡ 99.1% by HPLC detection. Mass spectrum m/z:798.2722 (theory: 798.2705). Theoretical element content (%) C 57 H 38 N 2 OS: c,85.69; h,4.79; n,3.51. Measured element content (%): c,85.65; h,4.85; n,3.49.
The organic materials in the preparation examples are purified by sublimation, and the purity is over 99.99 percent. The ITO/Ag/ITO glass substrate used in the preparation example is purchased from Shenzhen south glass display device technology Co.
The following are other compounds used in the preparation examples than the arylamine compounds of the present invention:
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 Table 3.
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.
Evaporating each organic layer and cathode layer by layer on the ITO glass substrate, specifically: a. 2-TNATA is used as a hole injection layer with the thickness of 60nm; b. NPB is used as a hole transport layer, and the thickness is 60nm; c. the compound D-1 is used as a light-emitting auxiliary layer, and the thickness is 20nm; d. (piq) 2 Ir (acac) and CBP (mass ratio of 5:95) are used as light-emitting layers, and the thickness is 30nm; e. BAlq is used as a hole blocking layer with the thickness of 10nm; f. alq 3 As an electron transport layer, the thickness was 50nm; g. LiF is used as an electron injection layer, and the thickness is 0.2nm; h. al was used as a cathode with a thickness of 150nm.
Comparative device preparation examples 2 to 3: contrast devices 2 to 3
The compound D-1 was replaced with the compounds D-2 and D-3, respectively, and the other steps were the same as those of comparative device preparation example 1, to obtain comparative devices 2 to 3.
Device preparation examples 1 to 29: light emitting devices 1 to 29
The compound D-1 was replaced with the arylamine compound of the present invention in synthetic examples 3 to 31, respectively, and the remaining steps were the same as those of comparative device preparation example 1, to obtain light-emitting devices 1 to 29.
TABLE 3 Table 3
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The device data of table 3 shows that when the arylamine compound of formula (I) is used as a light-emitting auxiliary layer in an OLED device, the driving voltage, light-emitting efficiency and service life of the device are significantly improved.
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 (5)
1. An aromatic amine compound, characterized in that the aromatic amine compound has a structure represented by formula (I):
wherein X is selected from oxygen atom or sulfur atom;
m is selected from integers of 0-3, and n is selected from integers of 0-4;
said R is a 、R b Independently selected from one of a hydrogen atom, a deuterium atom, when a plurality of R's are present a Or R is b When a plurality of R a The same or different, a plurality of R b The same or different;
the L is 1 ～L 2 Independently selected from a single bond or one of the substituents shown below:
the L is 3 -L 6 Independently selected from a single bond or one of the substituents shown below:
wherein, a is as follows 1 An integer selected from 0 to 4;
ar as described 1 ～Ar 4 At least one of which is selected from one of the following alicyclic-containing substituents:
The remainder of Ar not selected from the alicyclic-containing substituents 1 ～Ar 4 The groups are independently selected from one of the substituents shown below:
wherein p is an integer from 0 to 3, and q is an integer from 0 to 4;
said R is 31 Selected from one of hydrogen atom and deuterium atom, when a plurality of R's are present 31 When a plurality of R 31 The same or different;
R 33 and R is R 34 And are linked to form a deuterium substituted or unsubstituted cyclopentane ring, a deuterium substituted or unsubstituted cyclohexane ring.
2. The aromatic amine compound according to claim 1, wherein the aromatic amine compound has one of structures represented by formulas (II-a) to (II-B):
wherein, the L 3 ～L 6 、Ar 1 ～Ar 4 X is the same as that described in claim 1.
3. The aromatic amine compound according to claim 1, wherein the aromatic amine compound has one of structures represented by formulas (III-a) to (III-P):
wherein, the L 3 ～L 6 、Ar 1 ～Ar 4 X is the same as that described in claim 1.
4. An aromatic amine compound, characterized in that the aromatic amine compound is selected from one of the following compounds:
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5. an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a hole transporting region, a light emitting layer, and an electron transporting region, wherein the hole transporting region contains one or more of the aromatic amine compounds according to any one of claims 1 to 4.
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| CN107275362A (en) * | 2016-12-28 | 2017-10-20 | 上海天马有机发光显示技术有限公司 | A kind of OLED display panel and the electronic equipment comprising it |
| CN108821985A (en) * | 2018-06-01 | 2018-11-16 | 长春海谱润斯科技有限公司 | A kind of aromatic amine derivant and its organic electroluminescence device |
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| CN107275362A (en) * | 2016-12-28 | 2017-10-20 | 上海天马有机发光显示技术有限公司 | A kind of OLED display panel and the electronic equipment comprising it |
| CN108821985A (en) * | 2018-06-01 | 2018-11-16 | 长春海谱润斯科技有限公司 | A kind of aromatic amine derivant and its organic electroluminescence device |
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