CN116655639A - Amino compound and application thereof - Google Patents
Amino compound and application thereof Download PDFInfo
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- CN116655639A CN116655639A CN202310538650.0A CN202310538650A CN116655639A CN 116655639 A CN116655639 A CN 116655639A CN 202310538650 A CN202310538650 A CN 202310538650A CN 116655639 A CN116655639 A CN 116655639A
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- substituted
- unsubstituted
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- aryl
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- -1 Amino compound Chemical class 0.000 title claims abstract description 85
- 239000000463 material Substances 0.000 claims abstract description 53
- 239000010410 layer Substances 0.000 claims description 184
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 238000002347 injection Methods 0.000 claims description 31
- 239000007924 injection Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 230000005525 hole transport Effects 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 239000012044 organic layer Substances 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 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 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 4
- 150000002979 perylenes Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 2
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 2
- MWPCBCGAQVXDCZ-UHFFFAOYSA-N 1-amino-1-nitramidoguanidine Chemical compound [N+](=O)([O-])NN(C(N)=N)N MWPCBCGAQVXDCZ-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000005104 aryl silyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 238000000034 method Methods 0.000 description 16
- 230000032258 transport Effects 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000000151 deposition Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 3
- 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000005092 sublimation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 125000004431 deuterium atom Chemical group 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- JPJGNZQDELRZGE-UHFFFAOYSA-N (phenyl-$l^{2}-phosphanyl)benzene Chemical group C=1C=CC=CC=1[P]C1=CC=CC=C1 JPJGNZQDELRZGE-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- BZHGXQBPJUHVFW-UHFFFAOYSA-N toluene;tritert-butylphosphane Chemical compound CC1=CC=CC=C1.CC(C)(C)P(C(C)(C)C)C(C)(C)C BZHGXQBPJUHVFW-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an amino compound and application thereof in an organic electroluminescent material and a luminescent element.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an amino compound and application thereof in organic electroluminescent materials and luminous elements.
Background
Most of the materials used in the organic electroluminescent element are pure organic materials or organometallic complexes of organic materials and metals, and they are classified into hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, and the like, depending on the application. Here, an organic substance having a relatively small ionization energy is mainly used as the hole injection substance or the hole transport substance, and an organic substance having a relatively large electronegativity is mainly used as the electron injection substance or the electron transport substance. Further, the substance used as the light-emitting auxiliary layer preferably satisfies the following characteristics:
First, the materials used in the organic electroluminescent element need to have good thermal stability because joule heat is generated by charge transfer inside the organic electroluminescent element, and at present, the glass transition temperature of the materials commonly used as hole transport layers is low, so that a phenomenon occurs in which light emission efficiency is lowered due to crystallization occurring at the time of driving at low temperature; second, in order to reduce the driving voltage, the organic matters adjacent to the cathode and the anode are required to be designed to have small charge injection potential barrier and high charge mobility; third, there is always an energy barrier at the interface of the electrode and the organic layer, and at the interface of the organic layer and the organic layer, and some charges are inevitably accumulated, so that it is necessary to use a substance excellent in electrochemical stability.
The organic electroluminescent device generally includes an anode, a hole injection layer, a hole transport layer, a light emitting layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the light-emitting layer under the action of the electric field, holes at the anode side also move to the light-emitting layer, the electrons and the holes are combined in the light-emitting layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the light-emitting layer emits light.
In the prior art, KR1020190035567A, CN107459466A, CN106008424A, CN104583176A, CN103108859A, CN110467536a et al disclose materials that can be used to prepare hole transport layers in organic electroluminescent devices. However, there remains a need to continue to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
The invention aims to provide an amino compound, an organic electroluminescent material, a light-emitting element and a consumer product, which are used for improving the performance of the organic electroluminescent element.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
an amino compound has a structural general formula shown in a formula (I):
wherein Z represents a substituted or unsubstituted naphthyl group;
R 1 and R is 2 Are identical to or different from each other and each represent one or more to saturated substituents, each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 50 Aryloxy, substituted or unsubstituted C 1 ～C 30 Alkylthio, substituted or unsubstituted C 6 ～C 50 Arylthio, substituted or unsubstituted C 1 ～C 30 Alkylamino, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 6 ～C 50 Arylsilyl, cyano, halogen atoms, any adjacent two or more R 1 、R 2 Can be arbitrarily setForms a substituted or unsubstituted ring with or without heteroatoms N, O, S, P, B, si or Se in the ring formed;
L 1 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
m is selected from integers of 0 to 5;
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 10 ～C 50 Condensed aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl groups.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 30 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like;
Aryl groups in the sense of the present invention contain 6 to 50 carbon atoms, heteroaryl groups contain 2 to 50 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or s. In this case, two or more rings of the heteroaryl group may be attached to each other simply or in a condensed form, or may further include a condensed form with the aryl group. As non-limiting examples of aryl and heteroaryl groups, in particular groups selected from the following: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,Group, perylene group, fluoranthryl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl groupIndenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo [ g, id ]]Naphtho [2,1,8-cde]Azulene, triindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ] ]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthamidinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracnose oxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4, 5-diazapyrenyl, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenoxazinyl group, phenothiazinyl group, fluorogenic ring group, naphthyridinyl group, azacarbazolyl group, benzocarboline group, carboline group, phenanthroline group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazole group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,3, 4-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazinyl group, 1,2, 3-tetrazinyl group, 1, 3-tetrazinyl group, 3-tetrazolyl group, quinazolinyl group, indolizinyl group, pterine group, etc. A group consisting of benzothiadiazolyl groups or groups derived from a combination of these systems.
"halogen" or "halogen atom" as used herein means a member selected from fluorine, chlorine, bromine or iodine.
Further, the amine-based compound is selected from the group consisting of the structures shown below:
wherein the definition of the symbols used is the same as the definition described above.
Further, the R 1 、R 2 Each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenylA group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
Further, m is selected from 0, 1 or 2.
Further, the Ar 1 、Ar 2 、Ar 3 、Ar 4 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenylRadicals, substitutionsOr an unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
According to an embodiment of the invention, the R 1 、R 2 Each independently selected from the group consisting of hydrogen, deuterium, t-butyl, substituted or unsubstituted phenyl.
According to an embodiment of the invention, the Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenanthryl.
Heteroalkyl in the sense of the present invention means a hydrogen atom or-CH on an alkyl radical 2 Substituted with at least one heteroatom selected from halogen, nitrile, N, O, s or silicon, as non-limiting examples, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like. Haloalkyl refers to a partial or complete replacement of a hydrogen atom on an alkyl group with a halogen, and as non-limiting examples there are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl and the like.
Alkenyl or alkynyl groups useful in the present invention contain at least two carbon atoms, and are preferably considered to mean, by way of non-limiting example, the following groups: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.
Alkoxy, alkylthio, preferably alkoxy or alkylthio having 1 to 30 carbon atoms, as used in the present invention is understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octoxy, cyclooctoxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butyleneoxy, pentyleneoxy, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene oxy, cyclohexene thio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The radical may be replaced by N, O or S to form heterocycloalkyl, heterocycloalkenyl, e.g. one of the cyclopentyl groups-CH 2 -the radical is replaced by O to form one of the groups-CH in the tetrahydrofuranyl, cyclohexyl 2 -the group is replaced by O to form tetrahydropyranyl, etc.; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The aryloxy group used in the present invention means a monovalent functional group represented by R 'O-and R' is an aryl group having 6 to 50 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
As used herein, arylthio means a monovalent functional group represented by R 'S-wherein R' is an aryl group having 6 to 50 carbon atoms. As non-limiting examples of such arylthio groups, phenylthio, naphthylthio, biphenylthio and the like are mentioned.
The alkylsilyl group used in the present invention means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3, and as non-limiting examples of the alkylsilyl group, there are trimethylsilyl group, triethylsilyl group and the like. Aryl silicon group refers to alkyl silicon group substituted with at least one aryl group having 6 to 50 carbon atoms, and examples of the alkyl silicon group include phenyl dimethyl silicon group, naphthyl dimethyl silicon group, phenyl diethyl silicon group, diphenyl methyl silicon group, diphenyl ethyl silicon group, triphenyl silicon group, and the like.
"alkylcarbonyl", "alkoxycarbonyl", "arylcarbonyl", "arylborocarbonyl", "alkylborocarbonyl" in the sense of the present invention means a substituted carbonyl (-COR) wherein R is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboronyl, alkylboronyl.
The arylphosphorus group used in the present invention means a diarylphosphorus group substituted with an aryl group having 6 to 50 carbon atoms, and as non-limiting examples of the arylphosphorus group, there are diphenylphosphorus group, bis (4-trimethylsilylbenzene) phosphorus group and the like. The phosphorus atom of the aryl phosphorus oxide group is the diaryl phosphorus group is oxidized to the highest valence state.
The arylboron group used in the present invention means a diarylboroyl group substituted with an aryl group having 6 to 50 carbon atoms, and as non-limiting examples of the arylboron group, there are diphenyl boron group, bis (2, 4, 6-trimethylbenzene) boron group and the like. The alkylboryl group means a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms, and as non-limiting examples of the alkylboryl group, there are di-t-butylboryl group, diisobutylboryl group and the like.
The arylalkyl group according to the present invention means an alkyl group in which at least one hydrogen atom of a straight or branched saturated hydrocarbon having from 1 to 40 carbon atoms is substituted with an aryl group having from 6 to 50 carbon atoms, and as a non-limiting example, phenylmethyl group, diphenylmethyl group, triphenylmethyl group, 2-phenylethyl group, 3-phenylpropyl group and the like can be mentioned.
Alkylaryl according to the present invention refers to an aryl group in which at least one hydrogen atom of the aryl group having from 6 to 50 carbon atoms is substituted with a straight or branched saturated hydrocarbon having from 1 to 40 carbon atoms, and as a non-limiting example, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl and the like can be mentioned.
The substituents of the substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylamine, substituted condensed aryl, substituted arylene, substituted heteroarylene described herein are each independently selected from at least one of the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C 1 -C 40 Alkyl, C 1 -C 40 Haloalkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 1 -C 40 Alkylthio, C 3 -C 40 Cycloalkyl, C 3 -C 40 Cycloalkenyl, 3-to 7-membered heterocycloalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, unsubstituted or substituted by one or more C 6 -C 60 Aryl-substituted 3-to 30-membered heteroaryl, unsubstituted or deuterated, one or more C 1 -C 40 C substituted with at least one of an alkyl group and one or more 3-to 30-membered heteroaryl groups 6 -C 60 Aryl, tris (C) 1 -C 40 ) Alkylsilyl, tri (C) 6 -C 60 ) Aryl silicon based, di (C) 1 -C 40 ) Alkyl (C) 6 -C 60 ) Aryl silicon base, C 1 -C 40 Alkyldi (C) 6 -C 60 ) Aryl silicon base, C 1 -C 40 Alkylcarbonyl, C 1 -C 40 Alkoxycarbonyl group, C 6 -C 60 Arylcarbonyl, di (C) 6 -C 60 ) Arylborocarbonyl groups of di (C) 1 -C 40 ) Alkyl boron carbonyl, C 1 -C 40 Alkyl (C) 6 -C 60 ) Arylborocarbonyl, C 6 -C 60 Aryl (C) 1 -C 40 ) Alkyl, C 1 -C 40 Of alkyl (C) 6 -C 60 ) Aryl groups.
Arylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon having 6 to 50 carbon atoms. As non-limiting examples thereof, there are phenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene and the like.
The heteroarylene or heteroarylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from a heteroarene having 2 to 50 carbon atoms. As non-limiting examples thereof, there are a pyridyl group, a quinolyl group, an isoquinolyl group, a carbolinyl group, a pyrimidyl group, a triazinyl group and the like.
Arylene and heteroarylene as divalent functional groups with NAr according to the foregoing 3 Ar 4 Connection, preferably, the L 1 Selected from a single bond or a group consisting of groups III-1 to III-24:
wherein X is selected from O, S, se, CR ' R ', siR ' R ' or NAr ';
Z 11 、Z 12 、Z 13 、Z 14 each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Cyclic olefin group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5; y5 represents 1 or 2;
r ', R' are each independently selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstitutedC of (2) 2 -C 60 Heteroaryl, R' and R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, o or S in the ring formed; preferably, R', R "is methyl, phenyl or fluorenyl;
ar' is selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Heteroalkyl of (C) 3 -C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably, ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Wherein the dotted line represents the attachment site of the group.
Preferably, X is selected from O or S.
Preferably, the L 1 Selected from a single bond or a group consisting of groups III-1 to III-15, m-24:
preferably, said Z 11 、Z 12 、Z 13 、Z 14 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile groups.
Further, the amino compound is selected from one or more of the following structures B1007-B1138:
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wherein Ph is phenyl.
As used herein, "combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, the alkyl and deuterium atoms can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
An organic electroluminescent material comprising the amine-based compound; the organic electroluminescent material comprising the amine-based compound of the present invention has a carrier transporting ability.
The organic electroluminescent material may be constituted by using the amine-based compound of the present invention alone, or may contain other compounds at the same time.
Preferably, the organic electroluminescent material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, a capping layer (CPL layer for short) material, or an electron blocking layer material.
The invention also provides application of the amino compound in preparation of the organic electroluminescent element.
The present invention also provides an organic electroluminescent element comprising: a first electrode, a second electrode, a CPL layer and more than one organic layer arranged between the first electrode and the second electrode; at least one of the organic layer and the CPL layer comprises the amino compound.
The organic electroluminescent element comprises a cathode, an anode, CPL and at least one light emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent element described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention according to the invention.
Further, the organic electroluminescent element according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer is directly adjacent to the hole injection layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-transport layer and in the light-emitting layer and in the CPL layer, all materials can be used in the manner customary in accordance with the prior art. A person of ordinary skill in the art will thus be able to use all materials known in relation to organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
In general, an OLED includes at least one organic layer disposed between and electrically connected to an anode and a cathode. Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL layer) 110. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 containing two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED devices have one single color light emitting layer or three light emitting layers of three primary colors, while device 200 has two light emitting layers of the same color. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
The simple layered structure illustrated in fig. 1 and 2 is provided as a non-limiting example, and it should be understood that embodiments of the present invention may be used in conjunction with a wide variety of other structures. The particular materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be implemented by combining the various layers described in different ways based on design, performance, and cost factors, or several layers may be omitted entirely. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it will be understood that combinations of materials may be used, such as mixtures of host and dopant, or more generally, mixtures. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 204 transports holes and injects holes into light emitting layer 205, and may be described as a hole transport layer or an electron blocking layer. In one embodiment, an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or may further comprise multiple layers of different organic materials as described in fig. 1 and 2.
Structures and materials not specifically described, such as PLEDs comprising polymeric materials, may also be used. As another example, an OLED with a single organic layer or multiple stacks may be used. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve optical coupling.
On the other hand, in the organic electroluminescent element of the present invention, in addition to one or more of the above organic layers containing the above amine-based compound, the organic layers and the electrode can be formed by materials and methods well known in the art.
Further, a substance that can be used as an anode included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, metals such as vanadium, chromium, copper, zinc, gold, aluminum, or the like, or alloys thereof can be used; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO: al or SnO 2 : a combination of a metal such as Sb and an oxide; polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDT), polypyrrole, and polyaniline; and carbon black, etc.
The substance that can be used as the cathode included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, or the like can be usedA metal or an alloy thereof; liF/Al or Li 2 And multilayer structures such as O/Al.
The substance that can be used as the substrate included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, a sheet, or the like can be used.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Also preferred are organic electroluminescent elements in which one or more layers can also be applied by means of an organic vapor deposition process or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent elements are preferred, from which one or more layers are produced, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method of manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and/or applying at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or applying at least one layer from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferable cases as indicated above with respect to the organic electroluminescent element apply to the compound of the present invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds of the invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of preparations of the compounds of the invention, which preparations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl ketone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or mixtures of these solvents.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a CPL layer, or an electron blocking layer.
Further, the hole transport layer, light emitting layer, or CPL layer comprises the amine-based compound of the present invention.
A consumer product made from the organic electroluminescent device, the consumer product comprising the organic electroluminescent device provided by the invention.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
In addition, unless otherwise specified, all raw materials used in the present invention are commercially available, and any ranges recited in the present invention include any numerical value between the end values and any sub-range constituted by any numerical value between the end values or any numerical value between the end values.
The invention also relates to mixtures comprising at least one compound of formula (I) or a preferred embodiment described above and at least one further compound. If the compounds according to the invention are used as matrix materials, the other compounds may be fluorescent or phosphorescent emitters. The mixture may then additionally comprise other materials as additional matrix materials. The invention also relates to the use of the compounds according to the invention in electronic components. Preferably, as mentioned above and below, the compounds according to the invention are used in a hole transport layer or as host material in a light-emitting layer. The compounds according to the invention and the electronic components obtainable therefrom, in particular organic electroluminescent components, differ from the prior art in one or more of the following surprising advantages:
the amino compound has a large plane conjugated indenocarbazole rigid structure, and the compound represented by the general formula (I) has large mobility of (1) carriers; (2) high internal quantum efficiency; (3) stable film state; (4) The organic electroluminescent element of the present invention is suitable for use as a constituent material of a light-emitting layer of the organic electroluminescent element because of its excellent heat resistance.
In the organic electroluminescent element of the present invention using the amine compound represented by the general formula (I) as a host material for the light-emitting layer, since a compound having higher carrier mobility than conventional materials, high internal quantum efficiency, excellent amorphousness, and stable thin film state is used, it is possible to realize an organic electroluminescent element having high efficiency, low driving voltage, and long lifetime.
Further, in the present invention, the light-emitting layer is formed by the amine-based compound of the general formula (I), so that the high quantum efficiency performance and heat resistance of the compound can be utilized to the maximum extent, and the long-life organic electroluminescent element can be realized with higher efficiency.
In the present invention, the organic electroluminescent element of the present invention, in which the amine compound represented by the general formula (I) is used as a constituent material for at least one of the light-emitting layers or the laminated film in which two or more light-emitting layers are arranged, uses a compound having high carrier mobility, high internal quantum efficiency, excellent amorphism, and stable thin film state, and thus can realize a high-efficiency, low-driving voltage, and long-life organic electroluminescent element.
These advantages mentioned above are not accompanied by a weakening of other electronic properties.
It should be noted that variations of the embodiments described in the present invention fall within the scope of the present invention. Each feature disclosed in this disclosure may be replaced by alternative features serving the same, equivalent or similar purpose, unless expressly excluded. Thus, unless indicated otherwise, each feature disclosed in this document is to be understood as an example of a generic series or equivalent or similar feature.
All features of the invention may be combined with each other in any way, unless the specific features and/or steps are mutually exclusive. This applies in particular to the preferred features of the invention. Also, features that are not necessarily combined may be used alone (and not in combination). Furthermore, it should be noted that many features, particularly those of the preferred embodiments of the present invention, are inventive in their own right and should not be taken as part of an embodiment of the present invention. For these features, independent protection may be sought in addition to, or in lieu of, each of the presently claimed inventions.
The teachings of the technical actions disclosed in the present invention can be extracted and combined with other embodiments. The present invention is explained in more detail by the following examples, but is not intended to be limited thereby. Based on the description, one skilled in the art will be able to practice the invention throughout the scope of the disclosure and, without inventive effort, be able to prepare and use other compounds of the invention in electronic components or use the methods of the invention.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL layer) 111. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of organic compounds provided by the present invention, all of which are carried out under well known suitable conditions, involve some simple organic preparation, for example the preparation of phenylboronic acid derivatives, can be synthesised by skilled operating skills and are not described in detail in the present invention.
Any range recited in the invention includes any numerical value between the endpoints and any sub-range of any numerical value between the endpoints or any numerical value between the endpoints.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: using the NEWPORT 1931-C test;
life test: LTS-1004AC life test apparatus was used.
Example 1
A process for the preparation of compound B1007 comprising the steps of:
the first step: preparation of Compound Int-1
Under the protection of nitrogen, 20.0mmol of 1, 8-diphenyl-1, 8-dihydro-carbazolo [4,3-c ] carbazole is dissolved in 80mL of dichloromethane, the temperature is reduced to 0 ℃,20.0mmol of NBS is added in portions, stirring reaction is carried out for 2 hours, 50mL of water is added, the organic phase is separated out, water washing is carried out, the organic phase is dried and filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound Int-1 is separated and purified by a silica gel column, thus obtaining a yellow solid with the yield of 89%.
And a second step of: preparation of Compound B1007
22.0mmol of Int-1 prepared in the previous step and 20.0mmol of N-phenyl- [1,1' -biphenyl are reacted under the protection of nitrogen]-4-amine, 30.0mmol of sodium tert-butoxide, 0.2mmol of Pd 2 (dba) 3 Mixing with 0.5mmol of 10% tri-tert-butylphosphine toluene solution, adding 80mL of dimethylbenzene, heating to 110 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water, separating out an organic phase, extracting the aqueous phase with toluene, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound B1007, a yellow solid with a yield of 83%, and MS (TOF): m/z702.2923[ M+H ] ] + ， 1 HNMR(δ、CDCl 3 )：8.33～8.28(3H，m)；8.07～8.02(2H，m)；7.61～7.44(13H，m)；7.41～7.27(10H，m)；7.25～7.20(3H，m)；7.09～7.03(3H，m)；6.98～6.95(1H，d)。
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
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wherein Ph is phenyl.
Example 2
The preparation of compound B1036, comprising the steps of:
the first step: preparation of Compound Int-2
Under the protection of nitrogen, 10.0mmol of Int-1, 12.0mmol of phenylboronic acid, 30.0mmol of anhydrous sodium carbonate, 0.1mmol of Pd (PPh) 3 ) 4 Mixing, adding 40mL of toluene, 20mL of ethanol and 20mL of water, heating to reflux, stirring, reacting for 10 hours, cooling to room temperature, adding 50mL of water, separating out an organic phase, extracting the aqueous phase with toluene, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound Int-2 as a yellow solid with a yield of 78%.
And a second step of: preparation of Compound Int-3
Under the protection of nitrogen, 20.0mmol of Int-2 is dissolved in 50mL of dichloromethane and 10mL of DMF, the temperature is reduced to 0 ℃,21.0mmol of NBS is added in portions, the temperature is raised to room temperature, stirring is carried out for 2 hours, 50mL of water is added, the organic phase is separated out by water washing, the organic phase is dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound Int-3 is obtained by separating and purifying with a silica gel column, and is a yellow solid, and the yield is 92%.
And a third step of: preparation of Compound B1036
21.0mmol of Int-3 prepared in the previous step, 20.0mmol of diphenylamine, 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd under the protection of nitrogen 2 (dba) 3 Mixing with 0.4mmol Xantphos, adding 80mL of toluene, heating to 100 ℃ and stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water, separating out an organic phase, extracting the organic phase with toluene, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound B1036, yellow solid with a yield of 87%, MS (TOF): m/z 702.2927[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.33～8.28(3H，m)；8.07～8.02(2H，m)；7.77～7.71(4H，m)；7.68～7.62(2H，m)；7.56～7.47(9H，m)；7.36～7.27(4H，m)；7.08～7.02(4H，m)；7.00～6.96(2H，m)；6.94～,6.89(3H，m)；6.64～6.59(2H，m)。
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
example 3
Preparation of compound B1113:
10.0mmol of Int-4, 12.0mmol of (4- ([ 1,1' -biphenyl) under the protection of nitrogen]-4-yl (phenyl) amino) phenyl) boronic acid pinacol ester, 30.0mmol of anhydrous sodium carbonate, 0.1mmol of Pd (PPh) 3 ) 4 Mixing, adding 40mL of toluene, 20mL of ethanol and 20mL of water, heating to reflux, stirring, reacting for 10 hours, cooling to room temperature, adding 50mL of water, separating an organic phase, extracting the aqueous phase with toluene, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound B1113, yellow solid with a yield of 76%, MS (TOF): m/z 778.3156[ M+H ]] + ， 1 HNMR(δ、CDCl 3 )：8.78(1H，s)；8.44～8.40(2H，m)；8.35～8.31(1H，m)；8.04～8.01(1H，d)；7.67～7.59(4H，m)；7.56～7.45(8H，m)；7.43～7.30(9H，m)；7.27～7.22(4H，m)；7.04～6.92(6H，m)；6.90～6.85(3H，m)。
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
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example 4
As shown in fig. 1, the preparation method of the OLED element 100 includes the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, evaporating metallic silver as anode on the ITO film, and evaporating film thickness to beContinuously evaporating compound HATCN as hole injection layer to obtain an evaporating film with a thickness of +.>
3) Continuously depositing a layer of the compound shown in the formula (I) as a hole transport layer on the hole injection layer film, wherein the deposition film thickness is
4) Continuously evaporating a layer of compound HT202 as electron blocking layer on the hole transport layer to obtain an evaporating film with a thickness of
5) Continuously evaporating a layer of compounds GH345 and GD035 on the electron blocking layer as light-emitting layers, wherein GD035 is a doping material and the compound GH345 is a main material, the doping concentration of the compound GD035 in the GH345 is 10%, and the evaporating film thickness is
6) Evaporating a layer of compound LiQ and ET212 on the light-emitting layer to obtain an electron transport layer, wherein the mass ratio of LiQ to ET212 is 1:1, and the film thickness is
7) Evaporating a layer of compound LiF on the electron transport layer to obtain an electron injection layer with a thickness of
8) Evaporating metal magnesium and silver on the electron injection layer to obtain cathode layer with mass ratio of magnesium to silver of 1:10, and evaporating film thickness of
Finally, the compound of formula (I) of the present invention is deposited as a capping layer of the device on the cathode layer to a thickness of
The structure of the compound used in example 4 above is as follows:
comparative example 1
Example 4 the same procedure was followed except that compound H01 was used in place of the compound of formula (I) in example 4. The structure of compound H01 is:
the driving voltage and current efficiency of the organic electroluminescent elements prepared in example 4 and comparative example 1 and the lifetime of the elements were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent element was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; LT90% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent element was measured to be 900cd/m while maintaining a constant current at luminance 2 Time in hours. All results are summarized in table 1, and test results were normalized against the data of comparative example 1 (bracketed data) for comparison.
TABLE 1 results of testing the performance of the elements
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As can be seen from table 1, the compound of the present invention provides an organic electroluminescent element having high efficiency and long life as a material for a hole transport layer and a capping layer, and the element has low driving voltage, improved current efficiency, and excellent LT90% lifetime, indicating that the compound of the present invention is an organic electroluminescent material having excellent performance.
The compound H01 of comparative example 1 is different from the compound of the present invention in that the triphenylamine group of H01 is introduced into the 9-position of carbazole, the hole pair is quenched by direct adjacent nitrogen-nitrogen atoms, and holes cannot be effectively isolated, resulting in unbalanced transfer of excitons in the element, increased element driving voltage, and reduced efficiency. The compound of the invention introduces triarylamine groups to the phenyl ring of carbazole instead of nitrogen atoms, thus improving hole transmission capability, so that the compound has excellent performance in molecular film formation and hole transmission, more balanced exciton transmission in the element and improved element performance.
The organic electroluminescent device of the present invention can be applied to flat-panel light emitters such as wall-mounted televisions, flat-panel displays, and lighting, light sources such as copiers, printers, backlights for liquid crystal displays, and measuring instruments, display panels, and marker lamps.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (10)
1. The amino compound is characterized by having a structural general formula shown in a formula (I):
wherein Z represents a substituted or unsubstituted naphthyl group;
R 1 and R is 2 Are identical to or different from each other and each represent one or more to saturated substituents, each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstitutedC of (2) 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 50 Aryloxy, substituted or unsubstituted C 1 ～C 30 Alkylthio, substituted or unsubstituted C 6 ～C 50 Arylthio, substituted or unsubstituted C 1 ～C 30 Alkylamino, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 6 ～C 50 Arylsilyl, cyano, halogen atoms, any adjacent two or more R 1 、R 2 Optionally bonded or fused to form a substituted or unsubstituted ring with or without heteroatoms N, O, S, P, B, si or Se in the ring formed;
L 1 selected from single bonds, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
m is selected from integers of 0 to 5;
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 6 ～C 50 Arylamine group, substituted or unsubstituted C 10 ～C 50 Condensed aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl groups.
2. The amine-based compound of claim 1, wherein the amine-based compound is selected from the group consisting of the structures shown below:
wherein R is 1 、R 2 、Ar 1 、Ar 2 、L 1 、m、Ar 3 And Ar is a group 4 The definition of (a) is the same as that of formula (I).
3. The amine-based compound of claim 1, wherein R 1 、R 2 Each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl A group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group;
m is selected from 0, 1 or 2;
Ar 1 、Ar 2 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenylA group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group,Substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl.
4. The amine-based compound of claim 1, wherein R 1 、R 2 Each independently selected from the group consisting of hydrogen, deuterium, t-butyl, substituted or unsubstituted phenyl;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenanthryl.
5. The amine-based compound according to any one of claims 1 to 4, wherein L 1 Selected from a single bond or a group consisting of groups III-1 to III-24:
wherein X is selected from O, S, se, CR ' R ', siR ' R ' or NAr ';
Z 11 、Z 12 、Z 13 、Z 14 each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Substituted or unsubstituted cycloalkenylC of (2) 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5; y5 represents 1 or 2;
r ', R' are each independently selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl, R' and R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring formed; preferably, R', R "is methyl, phenyl or fluorenyl;
ar' is selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Heteroalkyl of (C) 3 -C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably, ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
wherein the dotted line represents the attachment site of the group.
6. The amine-based compound of any one of claims 1 to 5, wherein the amine-based compound is selected from the group consisting of structures represented by B1007-B1138:
Wherein Ph is phenyl.
7. An organic electroluminescent material, characterized in that it comprises the amine-based compound according to any one of claims 1 to 6.
8. An organic electroluminescent device comprising a first electrode, a second electrode, a capping layer, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer or capping layer comprises the amine-based compound of any one of claims 1-6.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer; wherein each organic layer may be one, two or more layers; the amine-based compound may be in the hole transport layer or in the light emitting layer or in the capping layer.
10. A consumer product comprising the organic electroluminescent device of any one of claims 8-9.
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