CN116284071A - Boron-containing organic compound serving as OLED doping material and organic electroluminescent device comprising same - Google Patents
Boron-containing organic compound serving as OLED doping material and organic electroluminescent device comprising same Download PDFInfo
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- CN116284071A CN116284071A CN202111560112.9A CN202111560112A CN116284071A CN 116284071 A CN116284071 A CN 116284071A CN 202111560112 A CN202111560112 A CN 202111560112A CN 116284071 A CN116284071 A CN 116284071A
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- substituted
- unsubstituted
- ring
- boron
- tritium
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- 239000000463 material Substances 0.000 title claims abstract description 114
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 43
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 30
- 239000010410 layer Substances 0.000 claims description 152
- -1 cyano, adamantyl Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 229910052722 tritium Inorganic materials 0.000 claims description 31
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 239000002346 layers by function Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 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
- 239000004305 biphenyl Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 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
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 150000001975 deuterium Chemical group 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 235000009470 Theobroma cacao Nutrition 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 125000001300 boranyl group Chemical group [H]B([H])[*] 0.000 claims description 2
- 244000240602 cacao Species 0.000 claims description 2
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- GDLYCTKVUHXJBM-UHFFFAOYSA-N diphenylborane Chemical compound C=1C=CC=CC=1BC1=CC=CC=C1 GDLYCTKVUHXJBM-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 10
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 5
- 238000006862 quantum yield reaction Methods 0.000 abstract description 4
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 230000009477 glass transition Effects 0.000 abstract description 3
- 238000002347 injection Methods 0.000 description 31
- 239000007924 injection Substances 0.000 description 31
- 230000000903 blocking effect Effects 0.000 description 26
- 239000010408 film Substances 0.000 description 25
- 238000005259 measurement Methods 0.000 description 24
- 239000000758 substrate Substances 0.000 description 24
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 14
- 239000007858 starting material Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000007740 vapor deposition Methods 0.000 description 9
- 239000003480 eluent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000004986 diarylamino group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 3
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 3
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 3
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229940127113 compound 57 Drugs 0.000 description 3
- 229940126179 compound 72 Drugs 0.000 description 3
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- 238000005538 encapsulation Methods 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
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- 230000005540 biological transmission Effects 0.000 description 2
- 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 2
- CDEASXIPDPAOGW-UHFFFAOYSA-N bis[4-(9,9-dimethylacridin-10-yl)phenyl]methanone Chemical compound C12=CC=CC=C2N(C2=C(C1(C)C)C=CC=C2)C1=CC=C(C(=O)C2=CC=C(N3C4=CC=CC=C4C(C4=C3C=CC=C4)(C)C)C=C2)C=C1 CDEASXIPDPAOGW-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
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- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
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- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
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- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical class CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- OMDTUSYJJFBYMG-UHFFFAOYSA-N 2,4-bis(9,9-dimethylfluoren-2-yl)-6-naphthalen-2-yl-1,3,5-triazine Chemical compound C1=CC=C2C(C)(C)C3=CC(C=4N=C(N=C(N=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 OMDTUSYJJFBYMG-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- TYHJXGDMRRJCRY-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) tin(4+) Chemical compound [O-2].[Zn+2].[Sn+4].[In+3] TYHJXGDMRRJCRY-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a boron-containing organic compound serving as an OLED doping material and an organic electroluminescent device containing the same, and belongs to the technical field of semiconductors. The structure of the compound is shown as a general formula (1), the boron-containing compound has a specific ring system structure, has a narrow half-peak width, high fluorescence quantum yield, high glass transition temperature and molecular thermal stability, and proper HOMO and LUMO energy levels, and when the boron-containing compound is used as a green light doped material in a light-emitting layer material of an OLED light-emitting device, the current efficiency, the light-emitting color purity and the service life of the device are greatly improved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a boron-containing organic compound serving as an OLED doping material and an organic electroluminescent device comprising the same.
Background
The traditional fluorescent doping material is limited by early technology, only 25% of singlet excitons formed by electric excitation can be used for emitting light, the internal quantum efficiency of the device is low (25% at maximum), the external quantum efficiency is generally lower than 5%, and the efficiency of the device is quite different from that of a phosphorescent device. The phosphorescent material enhances intersystem crossing due to strong spin-orbit coupling of heavy atom center, and can effectively utilize singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, most phosphorescent materials are expensive, the stability of the materials is poor, the color purity is poor, and the problems of serious roll-off of the device efficiency and the like limit the application of the phosphorescent materials in OLED.
With the advent of the 5G age, higher requirements are put on the color development standard, and besides high efficiency and stability, the luminescent material also needs narrower half-peak width to improve the luminescent color purity of the device. The fluorescent doping material can realize high fluorescence quanta and narrow half-peak width through molecular engineering, the blue fluorescent doping material has obtained a staged breakthrough, and the half-peak width of the boron material can be reduced to below 30 nm; in the green light region where human eyes are more sensitive, research is mainly focused on phosphorescent doped materials, but the luminescence peak shape is difficult to narrow by a simple method, so that the research on efficient green fluorescent doped materials with narrow half-peak width is of great significance for meeting higher color development standards.
In addition, the TADF sensitized fluorescence Technology (TSF) combines the TADF material with the fluorescence doped material, the TADF material is used as an exciton sensitization medium, the triplet state exciton formed by electric excitation is converted into the singlet state exciton, and the energy is transferred to the fluorescence doped material through the long-range energy transfer of the singlet state exciton, so that the device internal quantum efficiency of 100% can be achieved, the defect of insufficient utilization rate of the exciton of the fluorescence doped material can be overcome, the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of the fluorescence doped material can be effectively exerted, and the technology has wide prospect in the application of OLEDs.
The boron compound with a resonance structure can easily realize narrow half-peak width luminescence, and the material is applied to the TADF sensitized fluorescent technology, so that the device preparation with high efficiency and narrow half-peak width emission can be realized. As in CN 107507921A and CN 110492006A, disclosed is a light emitting layer composition technology in which TADF materials with the lowest singlet and lowest triplet energy level difference of 0.2eV or less are used as the main body and boron-containing materials are used as the doping materials; CN 110492005A and CN 110492009A disclose a luminescent layer composition scheme with exciplex as main body and boron-containing material as doping; can realize efficiency comparable to phosphorescence and relatively narrow half-width. Therefore, the development of the TADF sensitized fluorescence technology based on the narrow half-peak width boron luminescent material has unique advantages and strong potential on the index display facing BT.2020.
Disclosure of Invention
In view of the foregoing problems with the prior art, the applicant provides a boron-containing organic compound as a doping material for OLEDs. The compound has narrow half-peak width and high fluorescence quantum yield, and can be used as green light doping material of a luminescent layer of an organic electroluminescent device, thereby improving the luminescent color purity and the service life of the device.
The technical scheme of the invention is as follows: a boron-containing organic compound used as an OLED doping material, wherein the structure of the boron-containing organic compound is shown as a general formula (1):
in the general formula (1), Z 1 -Z 8 Each occurrence is identically or differently denoted as C-H or C- (R) 1 )；
R 1 Each occurrence of which is identically or differently represented by deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 30 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 6 ～C 30 Arylamine group, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 Heteroaryl or C containing at least one heteroatom of O, N, S, B, P, F 1 -C 18 An electron withdrawing group of (2); adjacent R 1 Can be connected into a ring;
M 1 ring, M 2 The rings being independently represented by C, substituted or unsubstituted 6 -C 30 Aromatic ring, substituted or unsubstituted C 2 -C 30 A heteroaromatic ring;
X 1 、X 2 、X 3 、X 4 each occurrence is identically or differently denoted as O, S or N- (R) 2 )；
R 2 Each occurrence of which is identically or differently denoted as substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 1 ～C 10 Alkylene, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 1 ～C 10 Alkoxy, substituted or unsubstituted C 1 ～C 10 Aryloxy, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 2 ～C 30 Heteroaryl; r is R 2 And R is R 1 、R 2 And M is as follows 1 Ring and/or M 2 The rings may be joined to form a ring;
the substituents of the above groups "substituted or unsubstituted" are optionally selected from deuterium, tritium, halogen, C 1 ～C 10 Alkyl, C 3 ～C 10 Cycloalkyl, C 6 ～C 30 Aryl, C 2 ～C 30 Heteroaryl, C 6 ～C 30 Aryl or C 2 ～C 30 Heteroaryl substituted amino, deuterium or tritium substituted C 1 ～C 10 Alkyl, deuterium or tritium substituted C 3 ～C 10 Any one of cycloalkyl groups;
the hetero atoms in the heteroaryl and heteroaryl rings are selected from one or more of oxygen, sulfur, boron, and nitrogen atoms.
The invention also provides an organic light-emitting device, which comprises a cathode, an anode and a functional layer, wherein the functional layer is positioned between the cathode and the anode.
The beneficial technical effects of the invention are as follows:
(1) The compound disclosed by the invention is applied to an OLED device, can be used as a doping material of a luminescent layer material, can emit fluorescence under the action of an electric field, and can be applied to the field of OLED illumination or OLED display;
(2) The compound provided by the invention has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;
(3) The spectrum FWHM of the compound is narrower, the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved;
Drawings
FIG. 1 is a schematic diagram of the structure of an OLED device using the materials of the present invention;
wherein 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and the embodiments of the present invention and features in the embodiments of the present invention may be combined with each other without conflict. The invention is further described below with reference to the drawings and specific examples, which are not intended to be limiting.
In the present invention, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule unless otherwise specified. Furthermore, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between energy levels is also a comparison of the magnitudes of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level, the lower the energy of the energy level.
In the drawings, the size of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. Further, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, words of "upper", "lower", "top" and "bottom", etc., which are used to indicate orientations, indicate only orientations in a certain specific state, and do not mean that the relevant structure can only exist in the orientations; conversely, if the structure can be repositioned, for example inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of an electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is farther from the substrate is the "top" side.
In the present invention, substituted or unsubstituted C 6 -C 30 Aryl and/or substituted or unsubstituted C 2 -C 30 Heteroaryl means 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 fused tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-biphenylyl group, a substituted or unsubstituted m-biphenylyl group, a substituted or unsubstituted p-biphenylyl group
A substituted or unsubstituted biphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted oxazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, combinations thereof, or a combination thereof Condensed rings of the aforementioned group combinations, but are not limited thereto.
C of the invention 1 -C 10 Alkyl (including straight chain alkyl and branched alkyl) refers to methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl and the like, but is not limited thereto.
The halogen atom in the present invention means a chlorine atom, a fluorine atom, a bromine atom, or the like, but is not limited thereto.
C of the invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as ring-forming atoms. In this context, preference is given to using C 4 -C 9 Cycloalkyl groups, more preferably C 5 -C 8 Cycloalkyl radicals, particularly preferably C 5 -C 7 Cycloalkyl groups. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, adamantyl, cycloheptyl, and the like, but are not limited thereto.
A boron-containing organic compound represented by the general formula (1):
in the general formula (1), Z 1 -Z 8 Each occurrence is identically or differently denoted as C-H or C- (R) 1 )；
R 1 Each occurrence of which is identically or differently represented by deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 30 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 6 ～C 30 Arylamine group, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 Heteroaryl or containing at least one of O, N, S, B, P, FHeteroatom C 1 -C 18 An electron withdrawing group of (2); adjacent R 1 Can be connected into a ring;
M 1 ring, M 2 The rings being independently represented by C, substituted or unsubstituted 6 -C 30 Aromatic ring, substituted or unsubstituted C 2 -C 30 A heteroaromatic ring;
X 1 、X 2 、X 3 、X 4 each occurrence is identically or differently denoted as O, S or N- (R) 2 )；
R 2 Each occurrence of which is identically or differently denoted as substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 1 ～C 10 Alkylene, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 1 ～C 10 Alkoxy, substituted or unsubstituted C 1 ～C 10 Aryloxy, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 2 ～C 30 Heteroaryl; r is R 2 And R is R 1 、R 2 And M is as follows 1 Ring and/or M 2 The rings may be joined to form a ring;
the substituents of the above groups "substituted or unsubstituted" are optionally selected from deuterium, tritium, halogen, C 1 ～C 10 Alkyl, C 3 ～C 10 Cycloalkyl, C 6 ～C 30 Aryl, C 2 ～C 30 Heteroaryl, C 6 ～C 30 Aryl or C 2 ～C 30 Heteroaryl substituted amino, deuterium or tritium substituted C 1 ～C 10 Alkyl, deuterium or tritium substituted C 3 ～C 10 Any one of cycloalkyl groups;
The hetero atoms in the heteroaryl and heteroaryl rings are selected from one or more of oxygen, sulfur, boron, and nitrogen atoms.
Preferably, the structure of the boron-containing organic compound is shown as any one of the general formulas (2) to (3):
in the general formula (2) and the general formula (3), Z 1 -Z 8 、M 1 Ring, M 2 Ring, X 1 、X 2 、X 3 、X 4 The definition of (2) is the same as that in the above general formula (1).
Preferably, the structure of the boron-containing organic compound is shown as any one of the general formulas (1-1) to (1-6):
in the general formulae (1-1) to (1-6), Z 1 -Z 8 、X 1 、X 2 、X 3 、X 4 The definition of (2) is the same as that in the above general formula (1);
X 5 、X 6 each occurrence is identically or differently denoted as O, S or N- (R) 3 )；
R 3 Each occurrence of which is identically or differently denoted as substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 Heteroaryl;
R a 、R b 、R c 、R d each occurrence is identically or differently denoted as deuterium, tritium, halogen, C 1 ～C 10 Alkyl, C 3 ～C 10 Cycloalkyl, C 6 ～C 30 Aryl, C 2 ～C 30 Heteroaryl, C 6 ～C 30 Aryl or C 2 ～C 30 Heteroaryl substituted amino, deuterium or tritium substituted C 1 ～C 10 Alkyl, deuterium or tritium substituted C 3 ～C 10 Cycloalkyl;
m, n, s, k are each independently represented as 0, 1, 2, 3, 4;
the substituents of the above groups "substituted or unsubstituted" are optionally selected from deuterium, tritium, halogen, C 1 ～C 10 Alkyl, C 3 ～C 10 Cycloalkyl, C 6 ～C 30 Aryl, C 2 ～C 30 Heteroaryl, C 6 ～C 30 Aryl or C 2 ～C 30 Heteroaryl substituted amino, deuterium or tritium substituted C 1 ～C 10 Alkyl, deuterium or tritium substituted C 3 ～C 10 Any one of cycloalkyl groups;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur, boron and nitrogen atoms.
Preferably, the structure of the boron-containing organic compound is shown as any one of the general formulas (4-1) to (4-8):
in the general formula (4-1) and the general formula (4-8), Z 1 -Z 8 、M 1 Ring, M 2 Ring, R 2 The definition of (2) is the same as that in the above general formula (1).
Preferably, the M 1 Ring, M 2 The rings are represented by the following ring structures:
asterisks indicate sites of the cocoa loop.
Preferred embodiment, R 1 、R a 、R b 、R c 、R d Represented by H, deuterium, tritium, fluorine atom, cyano, adamantyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted diphenylether, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted picolyl A pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted 9, 9-dimethylfluorenyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted boranyl group, a substituted or unsubstituted methoxy group.
M 1 Ring, M 2 The ring is represented by a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring;
R 2 、R 3 represented by H, deuterium, tritium, fluorine atom, adamantyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted diphenyl ether, substituted or unsubstituted naphthyl substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl.
The substituents for the above mentioned substitutable groups are optionally selected from deuterium, tritium, cyano, fluorine atom, trifluoromethyl, adamantyl, methyl, deuterated methyl, tritiated methyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, isobutyl, deuterated cyclopentyl, tritiated cyclopentyl, methoxy, tert-butoxy, diphenylamino, methyl-substituted diphenylamino, phenyl, deuterated phenyl, tritiated benzeneA group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a fluorine atom-substituted pyridyl group, a xanthonyl group, a cyano-substituted phenyl group, a cyano-substituted pyridyl group, a trifluoromethyl-substituted aryl group, a trifluoromethyl-substituted pyridyl group, a nitrogen atom-substituted terphenyl group, a C 6 ～C 30 Aryl-substituted carbonyl, azadimethylfluorenyl, azadiphenylfluorenyl, dimethylanthronyl, benzophenone, azabenzophenone, 9-fluorenonyl, anthraquinone, diphenylsulfone derivative, diphenylborane, methyl-substituted furyl.
Preferably, the specific structural formula of the boron-containing organic compound is any one of the following structures:
organic electroluminescent device
The invention provides an organic electroluminescent device, which comprises a cathode, an anode and a functional layer, wherein the functional layer is positioned between the cathode and the anode.
In a preferred embodiment of the present invention, the functional layer includes a light emitting layer, and the doping material of the light emitting layer is a boron-containing organic compound represented by general formula (1).
In a preferred embodiment of the present invention, the light emitting layer comprises a first host material, a second host material, and a doping material, at least one of the first host material and the second host material is a TADF material, and at least one of the first host material and the second host material is a boron-containing organic compound represented by the general formula (1).
Fig. 1 is a schematic structural diagram of an OLED device to which the compound of the present invention is applied, wherein 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices may be used. Examples are transparent substrates, such as glass or transparent plastic substrates; an opaque substrate such as a silicon substrate; a flexible PI film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency. The use direction of the substrate is different according to the property of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
A first electrode is formed on the substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), or Indium Tin Zinc Oxide (ITZO), or the like. When the first electrode is a semi-transmissive electrode or a reflective electrode, it may comprise Ag, mg, al, pt, pd, au, ni, nd, ir, cr or a metal mixture. The thickness of the first electrode layer depends on the material used, and is typically 50 to 500nm, preferably 70 to 300nm and more preferably 100 to 200nm.
The organic functional material layer arranged between the first electrode and the second electrode sequentially comprises a hole transmission region, a light emitting layer and an electron transmission region from bottom to top.
Herein, the hole transport region constituting the organic electroluminescent device may be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.
As the material for the hole injection layer, the hole transport layer, and the electron blocking layer, any material may be selected from known materials for use in OLED devices.
Examples of the above-mentioned materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinine derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinine derivatives, styrylanthracene derivatives, styrylamine derivatives and other styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene ethylene and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymer oligomers, aromatic tertiary amine compounds, styrylamine compounds, triamines, tetramines, biphenylamines, propyne derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1' -bis (4-diarylaminophenyl) cyclohexane, 4' -bis (diarylamino) biphenyls, bis [4- (diarylamino) phenyl ] methane, 4' -bis (diarylamino) terphenyl) s, 4' -bis (diarylamino) biphenyl ethers, 4' -bis (diarylamino) 4' -diaryl ] methane, 4' -bis (diarylamino) methane, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes or 2, 2-diphenylvinyl compounds, etc.
Further, according to the device collocation requirement, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer forming the organic electroluminescent device can be a single film layer or a superposition structure of a plurality of hole transport materials. In this context, the film thickness of the hole carrier conductive film layer having the above-described various functions is not particularly limited.
The hole injection layer comprises a host organic material capable of conducting holes and a P-type doped material having a deep HOMO level (and hence a deep LUMO level). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO level of the host organic material used for conducting holes in the anode interface buffer layer must have a certain characteristic with the P-doped material, so that it is expected to achieve occurrence of charge transfer states between the host material and the doped material, ohmic contact between the buffer layer and the anode, and efficient injection of injection conduction from the electrode to the holes.
In view of the above empirical summary, for hole host materials with different HOMO levels, different P-doped materials need to be selected to match the hole host materials, so that ohmic contact at the interface can be realized, and hole injection effect is improved.
Thus, in one embodiment of the present invention, for better injection of holes, the hole injection layer further comprises a P-type dopant material having charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4"- ((1 e,1' e,1" e) -cyclopropane-1, 2, 3-trimethylenetris (cyanoformylidene)) tris (2, 3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1 to 95:5, preferably 99:1 to 97:3, on a mass basis.
The thickness of the hole injection layer of the present invention may be 5 to 100nm, preferably 5 to 50nm and more preferably 5 to 20nm, but the thickness is not limited to this range.
The thickness of the hole transport layer of the present invention may be 5 to 200nm, preferably 10 to 150nm and more preferably 20 to 100nm, but the thickness is not limited to this range.
The thickness of the electron blocking layer of the present invention may be 1 to 20nm, preferably 5 to 10nm, but the thickness is not limited to this range.
After forming the hole injection layer, the hole transport layer, and the electron blocking layer, a corresponding light emitting layer is formed over the electron blocking layer.
The light emitting layer may include a host material, which may use a green host material common in the art, and a doping material, which uses the boron-containing organic compound represented by the general formula (1) of the present invention.
In the light-emitting layer of the present invention, the ratio of host material to dopant material used is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the light emitting layer may be adjusted to optimize light emitting efficiency and driving voltage. The preferred thickness range is 5nm to 50nm, more preferably 10 to 50nm, still more preferably 15 to 30nm, but the thickness is not limited to this range.
In the present invention, the electron transport region may include a hole blocking layer, an electron transport layer, and an electron injection layer disposed over the light emitting layer in this order from bottom to top, but is not limited thereto.
The hole blocking layer is used for blocking holes injected from the anode to pass through the light-emitting layer and enter the cathode, thereby prolonging the service life of the deviceLayers that hit and improve the performance of the device. The hole blocking layer of the present invention may be disposed over the light emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the art to have a hole blocking effect, for example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinoline) -4-phenylphenol (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, 9'- (5- (6- ([ 1,1' -biphenyl) and the like, can be used ]-4-yl) -2-phenylpyrimidin-4-yl) -1, 3-phenylene bis (9H-carbazole) (CAS number:1345338-69-3) Pyrimidine derivatives and the like. The hole blocking layer of the present invention may have a thickness of 2 to 200nm, preferably 5 to 150nm, and more preferably 10 to 100nm, but the thickness is not limited to this range.
The electron transport layer may be disposed over the light emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials for organic electroluminescent devices known in the art, for example, alq 3 Metal complexes of hydroxyquinoline derivatives represented by BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS No.: 1459162-51-6), and 2- (4- (9, 10-bis (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ]]Imidazole derivatives such as imidazole (CAS number: 561064-11-7, commonly known as LG 201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, and the like. The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm and more preferably 25 to 45nm, but the thickness is not limited to this range.
The electron injection layer may be disposed over the electron transport layer. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
The second electrode may be disposed over the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may comprise, for example, li, yb, ca, liF/Ca, liF/Al, al, mg, baF, ba, ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, mg, yb, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode is generally 10-50nm, preferably 15-20nm, depending on the material used.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
A method of preparing an organic electroluminescent device of the present invention comprises sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, the respective layers are preferably formed by a vacuum vapor deposition method. The individual process conditions in the vacuum evaporation process can be routinely selected by those skilled in the art according to the actual needs.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
The starting materials involved in the synthetic examples of the present invention are all commercially available or are prepared by methods conventional in the art;
Example 1 synthesis of compound 1:
(1) Preparation of intermediate M-1:
10mmol of raw material A-1 and 22mmol of raw material B-1 were added to a three-necked flask, dissolved in a mixed solvent (70 mL of toluene, 35mL of ethanol), and then 0.1mmol of Pd (PPh) 3 ) 4 K of 3mol/L 2 CO 3 15mL of aqueous solution was heated under reflux for 12 hours under nitrogen. The spot plate was sampled and the reaction was confirmed to be complete. After cooling to room temperature, the reaction mixture was filtered through a celite pad, rinsed with chloroform, and the resulting filtrate was evaporated in vacuo. The residue obtained was purified by column chromatography on silica gel using hexane/toluene as eluent to give intermediate M-1.LC-MS: measurement value: 595.16 ([ M+H)] + ) Theoretical value: 594.28.
(2) Preparation of intermediate N-1:
10mmol of intermediate M-1, 22mmol of raw material C-1 and 150ml of toluene are added under the protection of nitrogen gas in a three-necked flask, stirred and mixed, and then 0.05mmol of Pd is added 2 (dba) 3 ，0.05mmol P(t-Bu) 3 30mmol of sodium tert-butoxide, heating to 110 ℃, and carrying out reflux reaction for 24 hours; naturally cooling to room temperature, filtering, vacuum rotary evaporating, and subjecting the crude product to silica gel column chromatography (eluent: hexane/CH) 2 Cl 2 =5/1) to give the desired product intermediate N-1.LC-MS: measurement value: 747.26 ([ M+H)] + ) Theoretical value: 746.34.
(3) Preparation of Compound 1:
in a three-mouth bottle, under the protection of nitrogen,2mmol of boron tribromide and 1mmol of intermediate N-1 are dissolved in 30mL of 1,2, 4-trichlorobenzene. After stirring at 180 ℃ for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL) and 100mL of ph=6 sodium phosphate buffer solution was added at 0 ℃, the aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was chromatographed on a silica gel column (eluent: hexane/CH) 2 Cl 2 =5/1) to give the desired product compound 1.
Example 2 synthesis of compound 50:
(1) Preparation of intermediate a-1:
in a three-necked flask, under the protection of nitrogen, 12mmol of raw material D-1, 10mmol of raw material E-1 and 150ml of toluene are added and mixed under stirring, and then 0.05mmol of Pd is added 2 (dba) 3 ，0.05mmol P(t-Bu) 3 30mmol of sodium tert-butoxide, heating to 110 ℃, and carrying out reflux reaction for 24 hours; naturally cooling to room temperature, filtering, vacuum rotary evaporating, and subjecting the crude product to silica gel column chromatography (eluent: hexane/CH) 2 Cl 2 =5/1) to give the desired product intermediate a-1.LC-MS: measurement value: 336.19 ([ M+H)] + ) Theoretical value: 335.05.
(2) Preparation of intermediate b-1:
3mmol of intermediate a-1,6mmol of pinacol biborate, 9mmol of potassium acetate, 0.6mmol of S-phos and 0.12mmol of Pd are introduced into a three-necked flask under the protection of nitrogen 2 (dba) 3 To 150mL of dioxane was added, the reaction was refluxed for 8 hours, the reaction system was cooled to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure, and purified by silica gel column chromatography using n-heptane/ethyl acetate (9:1) as eluent to give intermediate b-1.LC-MS: measurement value: 428.23 ([ M+H)] + )，Accurate quality: 427.18.
(3) Preparation of intermediate M-2:
10mmol of raw material A-1, 22mmol of intermediate b-1 were added to a three-necked flask, dissolved in a mixed solvent (70 mL of toluene, 35mL of ethanol), followed by addition of 0.1mmol of Pd (PPh) 3 ) 4 K of 3mol/L 2 CO 3 15mL of aqueous solution was heated under reflux for 12 hours under nitrogen. The spot plate was sampled and the reaction was confirmed to be complete. After cooling to room temperature, the reaction mixture was filtered through a celite pad, rinsed with chloroform, and the resulting filtrate was evaporated in vacuo. The residue obtained was purified by column chromatography on silica gel using hexane/toluene as eluent to give intermediate M-2.LC-MS: measurement value: 707.35 ([ M+H)] + ) Theoretical value: 706.22.
(4) Preparation of intermediate N-2:
10mmol of intermediate M-2, 22mmol of raw material C-1 and 150ml of toluene are added under the protection of nitrogen gas in a three-necked flask, stirred and mixed, and then 0.05mmol of Pd is added 2 (dba) 3 ，0.05mmol P(t-Bu) 3 30mmol of sodium tert-butoxide, heating to 110 ℃, and carrying out reflux reaction for 24 hours; naturally cooling to room temperature, filtering, vacuum rotary evaporating, and subjecting the crude product to silica gel column chromatography (eluent: hexane/CH) 2 Cl 2 =5/1) to give the desired product intermediate N-2.LC-MS: measurement value: 859.07 ([ M+H)] + ) Theoretical value: 858.29.
(5) Preparation of compound 50:
in a three-necked flask, 2mmol of boron tribromide and 1mmol of intermediate N-2 were dissolved in 30mL of 1,2, 4-trichlorobenzene under nitrogen protection. After stirring at 180 ℃ for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL) and 100mL of ph=6 sodium phosphate buffer solution was added at 0 ℃, the aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was chromatographed on a silica gel column (eluent: hexane/CH) 2 Cl 2 =5/1) to give the desired product compound 50.
Example 3 synthesis of compound 57:
the procedure for the preparation of compound 57 was followed as in example 2, except that starting material B-2 was used instead of intermediate a-1 to give intermediate B-2, LC-MS: measurement value: 482.25 ([ M+H)] + ) Theoretical value: 481.32; replacement of intermediate b-1 with intermediate b-2 gives intermediate M-3, LC-MS: measurement value: 815.36 ([ M+H)] + ) Theoretical value: 814.50; replacement of intermediate M-2 with intermediate M-3 gives intermediate N-3, LC-MS: measurement value: 967.42 ([ M+H) ] + ) Theoretical value: 966.56; intermediate N-2 was replaced with intermediate N-3 to afford the desired product compound 57.
Example 4 synthesis of compound 72:
compound 72 was prepared by the same method as in example 2, except that starting material B-3 was used instead of intermediate a-1 to give intermediate B-3, lc-MS: measurement value: 404.08 ([ M+H)] + ) Theoretical value: 403.27; replacement of intermediate b-1 with intermediate b-3 gives intermediate M-4, LC-MS: measurement value: 659.34 ([ M+H)] + ) Theoretical value: 658.40; replacement of intermediate M-2 with intermediate M-4 gives intermediate N-4, LC-MS: measurement value: 811.29 ([ M+H)] + ) Theoretical value: 810.47; intermediate N-2 was replaced with intermediate N-4 to afford the desired product compound 72.
Example 5 synthesis of compound 77:
the procedure for the preparation of compound 77 was as in example 2, except that starting material B-4 was used instead of intermediate a-1 to give intermediate B-4, LC-MS: measurement value: 386.14 ([ M+H)] + ) Theoretical value: 385.22; substituting raw material A-2 for raw material A-1 and substituting intermediate b-4 for intermediate b-1 to obtain intermediate M-5, LC-MS: measurement value: 623.40 ([ M+H)] + ) Theoretical value: 622.31; replacement of intermediate M-2 with intermediate M-5 gives intermediate N-5, LC-MS: measurement value: 775.18 ([ M+H) ] + ) Theoretical value: 774.37; intermediate N-5 was substituted for intermediate N-2 to afford the desired product compound 77.
Example 6 synthesis of compound 95:
the procedure for the preparation of compound 95 was as in example 2, except that starting material A-2 was used instead of starting material A-1 to give intermediate M-6, LC-MS: measurement value: 707.17 ([ M+H)] + ) Theoretical value: 706.22; replacement of intermediate M-2 with intermediate M-6 gives intermediate N-6, LC-MS: measurement value: 859.21 ([ M+H)] + ) Theoretical value: 858.29; intermediate N-2 was replaced with intermediate N-6 to afford the desired product compound 95.
Example 7 synthesis of compound 98:
the procedure for the preparation of compound 98 was as in example 3, except that starting material A-2 was used instead of starting material A-1 to give intermediate M-7, LC-MS: measurement value: 815.42 ([ M+H)] + ) Theoretical value: 814.50; replacement of intermediate M-3 with intermediate M-7 gives intermediate N-7, LC-MS: measurement value: 967.37 ([ M+H)] + ) Theoretical value: 966.56; intermediate N-3 is replaced with intermediate N-7 to afford the desired product compound 98.
Example 8 synthesis of compound 117:
the procedure for the preparation of compound 117 was as in example 3, except that starting material A-3 was used instead of starting material A-1 to give intermediate M-8, LC-MS: measurement value: 817.35 ([ M+H) ] + ) Theoretical value: 816.47; replacement of intermediate N-3 with intermediate M-8 gives the desired product compound 117.
Example 9 synthesis of compound 154:
the procedure for the preparation of compound 154 was as in example 2, except that starting material B-5 was used instead of intermediate a-1 to give intermediate B-5, LC-MS: measurement value: 297.04 ([ M+H)] + ) Theoretical value: 296.16; intermediate A-1 is replaced with intermediate A-2 and intermediate b-1 is replaced with intermediate b-5 to give intermediate M-9, LC-MS: measurement value: 445.33 ([ M+H)] + ) Theoretical value: 444.18; replacing intermediate M-2 with intermediate M-9 and replacing starting material C-1 with starting material C-2 to give intermediate N-9, LC-MS: measurement value: 709.15 ([ M+H)] + ) Theoretical value: 708.37; intermediate N-9 is substituted for intermediate N-2 to afford the desired product compound 154.
The structural characterization of the compounds obtained in each example is shown in Table 1
TABLE 1
The compound of the invention is used in a light-emitting device and can be used as a doping material of a light-emitting layer. The compounds prepared in the above examples of the present invention were tested for physicochemical properties, and the test results are shown in table 2:
TABLE 2
Note that: the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter) at a heating rate of 10 ℃/min; the thermal weight loss temperature Td is a temperature at which the weight loss is 1% in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, the nitrogen flow rate is 20mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy measurement system (IPS-3), which was tested in a nitrogen atmosphere; eg was tested by a double beam uv-vis spectrophotometer (model: TU-1901), LUMO = HOMO + Eg; PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) were measured in a thin film state by a fluorescent-3 series fluorescence spectrometer of Horiba.
As can be seen from the above table data, the compounds of the present invention have higher glass transition temperatures and decomposition temperatures. The material can be used as a doping material of the light-emitting layer, so that crystallization and film phase separation of the material can be inhibited; meanwhile, the decomposition of the material under high brightness can be restrained, and the service life of the device is prolonged. In addition, the compound has a shallower HOMO energy level, is used as a doping material to be doped in a main material, is favorable for inhibiting generation of carrier traps, and improves energy transfer efficiency of main and guest bodies, so that luminous efficiency of the device is improved.
The compound provided by the invention has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; meanwhile, the spectrum FWHM of the material is narrower, the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved; finally, the vapor deposition decomposition temperature of the material is higher, the vapor deposition decomposition of the material can be restrained, and the service life of the device is effectively prolonged.
The effect of the OLED materials synthesized according to the present invention in the device will be described in detail below with reference to device examples 1 to 9 and device comparative examples 1 to 3. The device examples 2 to 9 and the device comparative examples 1 to 3 of the present invention were identical in the manufacturing process of the device as compared with the device example 1, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept uniform, except that the light-emitting layer material in the device was replaced. The layer structure and test results for each device example are shown in tables 3 and 4, respectively.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness 150 nm) is washed, that is, washed with a cleaning agent (semiconductor M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97:3. Next, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the electron blocking material was evaporated, a light emitting layer 6 of an OLED light emitting device was fabricated, using CBP as a host material, compound 1 as a dopant material, and the mass ratio of CBP to compound 1 was 97:3, with a light emitting layer film thickness of 30nm. After the light-emitting layer 6 was deposited, vacuum deposition of HB-1 was continued to give a film thickness of 5nm, and this layer was a hole blocking layer 7. After the hole blocking layer 7, vacuum evaporation is continued to be carried out on ET-1 and Liq, the mass ratio of ET-1 to Liq is 1:1, the film thickness is 30nm, and the electron transport layer 8 is formed. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 80nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10.
The effect of the OLED materials synthesized according to the present invention in the device will be described in detail below with reference to device examples 10 to 18 and device comparative examples 4 to 6. The device examples 11 to 18 and the device comparative examples 4 to 6 of the present invention were identical in the manufacturing process of the device as compared with the device example 10, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept uniform, except that the material of the light emitting layer in the device was changed. The layer structure and test results for each device example are shown in tables 3 and 4, respectively.
Device example 10
The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness is 150 nm) is washed, namely, washing with a cleaning agent (semiconductor M-L20), washing with pure water, drying, and ultraviolet-ozone washing to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97:3. Next, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a luminescent layer 6 of the OLED luminescent device is manufactured, CBP and DMAC-BP are used as double main materials, a compound 1 is used as a doping material, the mass ratio of the CBP to the DMAC-BP to the compound 1 is 67:30:3, and the thickness of the luminescent layer is 30nm. After the light-emitting layer 6 was deposited, vacuum deposition of HB-1 was continued to give a film thickness of 5nm, and this layer was a hole blocking layer 7. After the hole blocking layer 7, vacuum evaporation is continued to be carried out on ET-1 and Liq, the mass ratio of ET-1 to Liq is 1:1, the film thickness is 30nm, and the electron transport layer 8 is formed. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 80nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10.
The molecular structural formula of the related material is shown as follows:
after completing the OLED light emitting device as described above, the anode and cathode were connected by a well-known driving circuit, and the current efficiency, external quantum efficiency and lifetime of the device were measured. Examples of devices prepared in the same manner and comparative examples are shown in table 3; the test results of the current efficiency, external quantum efficiency and lifetime of the obtained device are shown in table 4.
TABLE 3 Table 3
TABLE 4 Table 4
Note that: voltage, current efficiency, luminescence peak using an IVL (current-voltage-brightness) test system (fresco scientific instruments, su-state); the life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 refers to the time taken for the device brightness to decay to 95%; all data were at 10mA/cm 2 And (5) testing.
As can be seen from the device data results of table 4, the current efficiency, external quantum efficiency, and device lifetime of the organic light emitting device of the present invention are greatly improved as compared with the OLED devices of the known materials, compared with the device comparative examples 1 to 6.
In summary, the above embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention, but any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. The boron-containing organic compound used as an OLED doping material is characterized in that the structure of the boron-containing organic compound is shown as a general formula (1):
in the general formula (1), Z 1 -Z 8 The same or each occurrenceDifferently denoted as C-H or C- (R) 1 )；
R 1 Each occurrence of which is identically or differently represented by deuterium atom, halogen atom, cyano group, substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 30 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 6 ～C 30 Arylamine group, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 Heteroaryl or C containing at least one heteroatom of O, N, S, B, P, F 1 -C 18 An electron withdrawing group of (2); adjacent R 1 Can be connected into a ring;
M 1 ring, M 2 The rings being independently represented by C, substituted or unsubstituted 6 -C 30 Aromatic ring, substituted or unsubstituted C 2 -C 30 A heteroaromatic ring;
X 1 、X 2 、X 3 、X 4 each occurrence is identically or differently denoted as O, S or N- (R) 2 )；
R 2 Each occurrence of which is identically or differently denoted as substituted or unsubstituted C 1 ～C 10 Alkyl, substituted or unsubstituted C 1 ～C 10 Alkylene, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 1 ～C 10 Alkoxy, substituted or unsubstituted C 1 ～C 10 Aryloxy, substituted or unsubstituted C 6 ～C 30 Aryl, substituted or unsubstituted C 2 ～C 30 Heteroaryl; r is R 2 And R is R 1 、R 2 And M is as follows 1 Ring and/or M 2 The rings may be joined to form a ring;
the substituents of the above groups "substituted or unsubstituted" are optionally selected from deuterium, tritium, halogen, C 1 ～C 10 Alkyl, C 3 ～C 10 Cycloalkyl, C 6 ～C 30 Aryl, C 2 ～C 30 Heteroaryl, C 6 ～C 30 Aryl or aryl radicalsC 2 ～C 30 Heteroaryl substituted amino, deuterium or tritium substituted C 1 ～C 10 Alkyl, deuterium or tritium substituted C 3 ～C 10 Any one of cycloalkyl groups;
the hetero atoms in the heteroaryl and heteroaryl rings are selected from one or more of oxygen, sulfur, boron, and nitrogen atoms.
2. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound has a structure represented by any one of the general formulae (2) to (3):
in the general formula (2) and the general formula (3), Z 1 -Z 8 、M 1 Ring, M 2 Ring, X 1 、X 2 、X 3 、X 4 Is defined as in claim 1.
3. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound has a structure represented by any one of the general formulae (1-1) to (1-6):
in the general formulae (1-1) to (1-6), Z 1 -Z 8 、X 1 、X 2 、X 3 、X 4 Is as defined in claim 1;
X 5 、X 6 each occurrence is identically or differently denoted as O, S or N- (R) 3 )；
R 3 Each occurrence of which is identically or differently denoted as substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 ～C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstitutedSubstituted C 2 -C 30 Heteroaryl;
R a 、R b 、R c 、R d each occurrence is identically or differently denoted as deuterium, tritium, halogen, C 1 ～C 10 Alkyl, C 3 ～C 10 Cycloalkyl, C 6 ～C 30 Aryl, C 2 ～C 30 Heteroaryl, C 6 ～C 30 Aryl or C 2 ～C 30 Heteroaryl substituted amino, deuterium or tritium substituted C 1 ～C 10 Alkyl, deuterium or tritium substituted C 3 ～C 10 Cycloalkyl;
m, n, s, k are each independently represented as 0, 1, 2, 3, 4;
the substituents of the above groups "substituted or unsubstituted" are optionally selected from deuterium, tritium, halogen, C 1 ～C 10 Alkyl, C 3 ～C 10 Cycloalkyl, C 6 ～C 30 Aryl, C 2 ～C 30 Heteroaryl, C 6 ～C 30 Aryl or C 2 ～C 30 Heteroaryl substituted amino, deuterium or tritium substituted C 1 ～C 10 Alkyl, deuterium or tritium substituted C 3 ～C 10 Any one of cycloalkyl groups;
the hetero atom in the heteroaryl is selected from one or more of oxygen, sulfur, boron and nitrogen atoms.
4. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound has a structure represented by any one of the general formulae (4-1) to (4-8):
in the general formula (4-1) and the general formula (4-8), Z 1 -Z 8 、M 1 Ring, M 2 Ring, R 2 Is defined as in claim 1.
5. The co-formulation of claim 1An organic compound of the vibration mode, characterized in that 1 Ring, M 2 The rings are represented by the following ring structures:
asterisks indicate sites of the cocoa loop.
6. The boron-containing organic compound according to claim 1, wherein R 1 、R a 、R b 、R c 、R d Represented by H, deuterium, tritium, fluorine atom, cyano, adamantyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted diphenyl ether, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazinyl, substituted or unsubstituted boranyl, unsubstituted methoxyl.
M 1 Ring, M 2 The ring is represented by a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring;
R 2 、R 3 represented by H, deuterium, tritium, fluorine atom, adamantyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted diphenyl ether, substituted or unsubstituted naphthyl substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl.
The substituents for the substituents mentioned above are optionally selected from deuterium, tritium, cyano, fluorine atom, trifluoromethyl, adamantyl, methyl, deuteromethyl, tritium methyl, ethyl, deuteroethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritium isopropyl, tert-butyl, deuterated tert-butyl, tritium tert-butyl, isobutyl, deuterated cyclopentyl, tritium cyclopentyl, methoxy, tert-butoxy, diphenylamino, methyl-substituted diphenylamino, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritium-substituted biphenyl, naphthyl, anthracenyl, phenanthryl, pyridinyl, quinolinyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, fluorine atom-substituted pyridinyl, xanthonyl, cyano-substituted phenyl, cyano-substituted pyridinyl, trifluoromethyl-substituted aryl, trifluoromethyl-substituted pyridinyl, nitrogen atom-substituted terphenyl, C 6 ～C 30 Aryl-substituted carbonyl, azadimethylfluorenyl, azadiphenylfluorenyl, dimethylanthronyl, benzophenone, azabenzophenone, 9-fluorenonyl, anthraquinone, diphenylsulfone derivative, diphenylborane, methyl-substituted furyl.
7. The boron-containing organic compound according to claim 1, wherein the specific structural formula of the boron-containing organic compound is any one of the following structures:
8. an organic light-emitting device comprising a cathode, an anode and a functional layer, the functional layer being located between the cathode and the anode, characterized in that the functional layer of the organic light-emitting device comprises the boron-containing organic compound according to any one of claims 1 to 7.
9. The organic light-emitting device according to claim 8, wherein the functional layer comprises a light-emitting layer, and wherein a doping material of the light-emitting layer is the boron-containing organic compound according to any one of claims 1 to 7.
10. The organic light-emitting device according to claim 8, wherein the light-emitting layer comprises a first host material, a second host material, and a doping material, wherein at least one of the first host material and the second host material is a TADF material, and wherein the doping material is the boron-containing organic compound according to any one of claims 1 to 7.
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