CN114605395B - Compound containing triazine and dibenzofuran structures and application thereof - Google Patents
Compound containing triazine and dibenzofuran structures and application thereof Download PDFInfo
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- CN114605395B CN114605395B CN202011429597.3A CN202011429597A CN114605395B CN 114605395 B CN114605395 B CN 114605395B CN 202011429597 A CN202011429597 A CN 202011429597A CN 114605395 B CN114605395 B CN 114605395B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 title claims abstract description 20
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 133
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 29
- 230000000903 blocking effect Effects 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000010409 thin film Substances 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- KZWMXGXPAHUUMY-UHFFFAOYSA-N OC12C(C(C(N(C2=CC=CC1)O)(O)O)(O)O)(O)O.[Li] Chemical compound OC12C(C(C(N(C2=CC=CC1)O)(O)O)(O)O)(O)O.[Li] KZWMXGXPAHUUMY-UHFFFAOYSA-N 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 207
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000002347 injection Methods 0.000 description 35
- 239000007924 injection Substances 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000758 substrate Substances 0.000 description 27
- 239000010408 film Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- 230000008878 coupling Effects 0.000 description 14
- 238000010168 coupling process Methods 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 14
- 238000005070 sampling Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 229910001873 dinitrogen Inorganic materials 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- -1 styrene compound Chemical class 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
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- 238000001035 drying Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000010025 steaming Methods 0.000 description 8
- 125000004986 diarylamino group Chemical group 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
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- 238000002156 mixing Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 238000007738 vacuum evaporation Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 150000004826 dibenzofurans Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
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- 238000007740 vapor deposition Methods 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
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- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
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- 229910052709 silver Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
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- 230000021615 conjugation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
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- 229910052744 lithium Inorganic materials 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 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
- 238000012546 transfer Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
- 235000019798 tripotassium phosphate Nutrition 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical class CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- MAGZFRRCWFGSHK-UHFFFAOYSA-N 1,2,3,4-tetraphenylbenzene Chemical group C1=CC=CC=C1C(C(=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 MAGZFRRCWFGSHK-UHFFFAOYSA-N 0.000 description 1
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- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-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
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
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- NTLMGXXRPUGUEG-UHFFFAOYSA-N 4-(3-dibenzofuran-4-ylphenyl)-3-(4-phenylphenyl)aniline Chemical compound C1=CC=C(C=C1)C2=CC=C(C=C2)C3=C(C=CC(=C3)N)C4=CC=CC(=C4)C5=CC=CC6=C5OC7=CC=CC=C67 NTLMGXXRPUGUEG-UHFFFAOYSA-N 0.000 description 1
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- 238000003475 lamination Methods 0.000 description 1
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- 230000031700 light absorption Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UVEAFTFQMHUWEY-UHFFFAOYSA-N methane;1,2,4,5-tetrafluoro-3,6-dioxocyclohexane-1,2,4,5-tetracarbonitrile Chemical compound C.C.N#CC1(F)C(=O)C(F)(C#N)C(F)(C#N)C(=O)C1(F)C#N UVEAFTFQMHUWEY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical class CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- YRPMGVDYZGWOPA-UHFFFAOYSA-N pyridin-2-yloxyboronic acid Chemical compound OB(O)OC1=CC=CC=N1 YRPMGVDYZGWOPA-UHFFFAOYSA-N 0.000 description 1
- XJYYTJSLGQZIJU-UHFFFAOYSA-N pyridin-3-yloxyboronic acid Chemical compound OB(O)OC1=CC=CN=C1 XJYYTJSLGQZIJU-UHFFFAOYSA-N 0.000 description 1
- VSJSXTHAYDUTBI-UHFFFAOYSA-N pyridin-4-yloxyboronic acid Chemical compound OB(O)OC1=CC=NC=C1 VSJSXTHAYDUTBI-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/14—Carrier transporting layers
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Abstract
The invention discloses an organic compound containing triazine and dibenzofuran and application thereof, belonging to the technical field of semiconductor materials. When the compound is used as a material of an organic electroluminescent device, the driving voltage, the current efficiency and the service life of the device are all obviously improved.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to an organic compound containing triazine and dibenzofuran structures and application thereof in an organic electroluminescent device.
Background
The organic electroluminescent device (OLED: organic Light Emission Diodes) technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The OLED device has a sandwich-like structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various functional materials are mutually overlapped together according to purposes to jointly form the OLED light-emitting device. When voltage is applied to the electrodes at the two ends of the OLED light-emitting device serving as a current device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the light-emitting layer, and thus OLED electroluminescence is generated.
Currently, the OLED display technology has been applied in the fields of smart phones, tablet computers and the like, and further will expand to the large-size application fields of televisions and the like. However, compared with the actual product application requirements, the performance of the OLED device, such as luminous efficiency and service life, needs to be further improved. Current research into improving performance of OLED light emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, prolonging the service life of the device, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only is the innovation of the structure and the manufacturing process of the OLED device needed, but also the continuous research and innovation of the OLED photoelectric functional material are needed, and the OLED functional material with higher performance is created.
The OLED photoelectric functional materials applied to OLED devices can be divided into two main categories in terms of application, namely charge injection transport materials and luminescent materials. Further, the charge injection transport material may be further classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be further classified into a host light emitting material and a doping material. In order to manufacture high-performance OLED light emitting devices, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, and the like, and as a host material of a light emitting layer, good bipolar properties, appropriate HOMO/LUMO energy levels, and the like are required. For an OLED device, electrons are injected from the cathode and then transferred to the host material through the electron transport layer, where they recombine with holes, thereby generating excitons. Therefore, the injection capability and the transmission capability of the electron transmission layer are improved, the device driving voltage is reduced, and meanwhile, the high-efficiency electron-hole recombination efficiency is obtained. Therefore, the electron transport layer is very important, and it is required to have high electron injection capability, transport capability, and high durability of electrons.
The heat resistance and film stability of the material are also important for device lifetime. A material having low heat resistance is likely to be decomposed not only at the time of material vapor deposition but also by heat generated by the device at the time of device operation, and causes material deterioration. Under the condition of poor phase stability of the material film, the material also generates film crystallization in a short time, so that the organic film layer is directly separated, and the device is deteriorated. Therefore, the materials used are required to have high heat resistance and good film stability.
With the remarkable progress of OLED devices, the performance requirements for materials are increasing, not only are they required to have good material stability, but also to achieve good efficiency and lifetime at low driving voltages. However, the existing electron transport materials have insufficient heat resistance stability, and meanwhile, the electron tolerance of the materials has defects, so that the materials are separated or decomposed in a phase state when the device works, and the service life of the device is lower.
Disclosure of Invention
In view of the above problems in the prior art, the applicant provides an organic compound containing triazine and dibenzofuran structures, which has better thermal stability and evaporation stability and higher electron mobility.
An object of the present invention is to provide an organic compound containing triazine and dibenzofuran, wherein the structure of the organic compound is shown as a general formula (1):
In the general formula (1), ar 1 represents phenyl or pyridyl;
Ar 2 is phenyl, biphenyl, naphthyl, pyridyl, carbazolyl, quinolinyl or phenanthryl;
r is spirofluorenyl, represented by formula (1-1), formula (1-2) or formula (1-3);
In the formula (1-1), R 3、R4 represents methyl or phenyl;
in the formula (1-3), X represents an oxygen atom or a dimethyl-substituted methylene group.
Further, R is one of the formulas A-1 to A-8;
Further, the organic compound is represented by one of the structures represented by the general formulae (2) to (9);
In the general formulae (2) to (9), ar 1 represents phenyl or pyridyl;
Ar 2 is phenyl, biphenyl, naphthyl, pyridyl, carbazolyl, quinolinyl or phenanthryl.
Further, the compound is represented by any one of the structures represented by the general formulae (10) to (41);
In the general formulae (10) to (41), ar2 is independently a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a carbazolyl group, a quinolinyl group or a phenanthryl group.
Further, the specific structure of the organic compound is any one of the following structures:
Another object of the present invention is to provide an organic electroluminescent device comprising a first electrode, a second electrode, and a plurality of organic thin film layers between the first electrode and the second electrode, wherein the organic thin film layers comprise a light emitting layer and one or more of a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and at least one organic thin film layer contains one or more of the organic compounds.
It is a further object of the present invention to provide the use of the organic compounds containing triazine and dibenzofuran structures according to the invention as electron transport layer materials in organic electroluminescent devices.
Another object of the present invention is to provide the use of the organic compound containing triazine and dibenzofuran structures according to the present invention as a host material for a light emitting layer in an organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device comprising the organic compound containing triazine and dibenzofuran structures according to the present invention.
Technical effects
The compound takes triazine-linked phenyl or pyridyl-substituted dibenzofuran groups as cores, has higher glass transition temperature, electron tolerance and molecular thermal stability, proper HOMO/LUMO energy level, and lower evaporation temperature and good electron mobility, so that the compound can effectively improve the photoelectric property and the service life of an OLED device when being used as an electron transport material or a main body material of an OLED functional layer.
Compounds formed by attaching a phenyl or pyridyl substituted dibenzofuran to a triazine exhibit excellent properties. The LUMO electron cloud distribution of the compound is further delocalized, so that the electron resistance of the material can be improved, and the electron stability of the material can be effectively improved. In addition, the parent nucleus can increase weak interaction in molecules, effectively reduce the vapor deposition temperature of the molecules and improve the thermal durability of the material. Furthermore, the parent nucleus can inhibit pi-pi accumulation among molecules, so that the electron mobility of the molecules is obviously improved, and the driving voltage of the device is reduced. In addition, due to the existence of the electricity absorption conjugation function of the mother nucleus, the vitrification transfer temperature of the material is raised, and the film stability of the material is effectively improved. Therefore, the compound can be used as an electron transport material to effectively reduce the driving voltage of the device, improve the efficiency of the device and prolong the service life of the device.
The compounds employed in the present invention are linked via a triazine and a phenyl or pyridyl substituted dibenzofuran group. As can be understood from examples (described later), the compounds of the above structures have a high glass transition point Tg (for example, 120 ℃ or higher), a low vapor deposition temperature (for example, less than 350 ℃), a high electron mobility (more than 3.0×e-4cm 2/Vs), stable film stability, excellent heat resistance, and a high electron mobility.
In addition, compared with the LUMO energy level (2.9-3.0 eV) of a common electron transport material, the compound has a deeper LUMO energy level (more than or equal to 3.0 eV). Under the action of an electric field or heat energy, the compound is easy to reduce and free lithium ions in the lithium complex due to the strong electricity absorption conjugation effect, so that the electron injection capacity is improved. Therefore, the compound is used as an electron transport material, has excellent electron transport capacity and good electron injection property, and can effectively reduce the driving voltage of a device, improve the efficiency of the device and prolong the service life of the device.
Drawings
Fig. 1 is a schematic diagram of the structure of the materials listed in the present invention applied to an OLED device. In the figure, 1 is a transparent substrate layer, and 2 is a first electrode layer, i.e., 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 an electron transport layer, 8 is an electron injection layer, 9 is a second electrode layer, i.e. a cathode layer, and 10 is an optical coupling layer.
Detailed Description
The technical aspects of the present invention will be described in detail below with reference to embodiments.
In the present application, 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 application, 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.
Any numerical range recited herein is intended to include all sub-ranges subsumed therein with the same numerical accuracy. For example, "1.0 to 10.0" means all subranges included between the minimum value of 1.0 listed and the maximum value of 10.0 listed (and including 1.0 and 10.0), that is, all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0. Any maximum numerical limitation listed herein is meant to include all smaller numerical limitations, and any minimum numerical limitation listed herein is meant to include all larger numerical limitations, all smaller numerical limitations, and all smaller numerical limitations, all larger numerical limitations, and all smaller numerical limitations, all as recited herein are meant to be included herein. Accordingly, the applicant reserves the right to modify the present specification including the claims to expressly describe any subranges falling within the scope of the explicit description herein.
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 application, in describing the electrodes and the organic electroluminescent device, and other structures, words such as "upper" and "lower" used to indicate orientations are merely indicative of 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 application, the "lower" 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 "upper" side.
Organic electroluminescent device
In another embodiment of the present application, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a plurality of organic thin film layers between the first electrode and the second electrode, wherein at least one of the organic thin film layers contains the organic compound having triazine and dibenzofuran structures.
In a preferred embodiment of the present application, the organic thin film layer comprises an electron transport layer, wherein the electron transport layer comprises the organic compound containing triazine and dibenzofuran structures according to the present application. Preferably, the electron transport layer comprises, in addition to the organic compound according to the application, further electron transport materials, such as Liq (see examples for specific chemical structures).
In a preferred embodiment of the present invention, the organic electroluminescent device according to the present invention comprises a substrate, a first electrode layer, an organic thin film layer, a second electrode layer, and an optical coupling layer, wherein the organic thin film layer includes, but is not limited to, a light emitting layer, and a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron blocking layer, and/or an electron injection layer.
The preferred device structure of the present invention takes the form of top emission (top emission). Preferably, the anode of the organic electroluminescent device of the present invention employs an electrode having high reflectivity, preferably ITO/Ag/ITO; the cathode adopts a transparent electrode, preferably adopts a mixed electrode of Mg and Ag=1:9, thereby forming a microcavity resonance effect, and the light emitted by the device is emitted from the side of the Mg and Ag electrode.
In a preferred embodiment of the present invention, there is provided an organic electroluminescent device comprising a substrate, an anode, a cathode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode layer, wherein the anode is over the substrate, the hole injection layer is over the anode, the hole transport layer is over the hole injection layer, the electron blocking layer is over the hole transport layer, the light emitting layer is over the hole transport layer, the electron transport layer is over the light emitting layer, the electron injection layer is over the electron transport layer, the cathode layer is over the electron injection layer, and the optical coupling layer is over the cathode.
Hereinafter, the structure of the organic electroluminescent device according to an embodiment of the present application will be described in detail with reference to fig. 1.
As shown in fig. 1, according to one embodiment of the present application, the present application provides an organic electroluminescent device comprising 1, a substrate, in order from bottom to top; 2. a first electrode layer; 3. a hole injection layer; 4. a hole transport layer; 5. an electron blocking layer; 6. a light emitting layer; 7. an electron transport layer; 8. an electron injection layer; 9. a second electrode layer; 10. an optical coupling 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 or a cathode. The anode material is preferably a material having a high work function so that holes are easily injected into the organic functional material layer. Non-limiting examples of anode materials include, but are not limited to, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The first electrode may have a single-layer structure or a multi-layer structure including two or more layers. For example, the anode may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. In addition, the thickness of the anode depends on the material used, and is usually 50 to 500nm, preferably 70 to 300nm and more preferably 100 to 200nm.
The hole injection layer 3, the hole transport layer 4, and the electron blocking layer 5 may be disposed between the first electrode 2 and the light emitting layer 6.
The hole injection layer structure is such that a hole injection layer material, which may be, for example, a P dopant, is uniformly or non-uniformly dispersed in the hole transport layer. The P-dopant may be selected from at least one compound selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; or cyano-containing compounds.
According to the invention, P1 is preferably used as P dopant. The ratio of the hole transport layer to the P dopant used in the present invention 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 hole injection layer of the present invention may be 1 to 100nm, preferably 2 to 50nm and more preferably 5 to 20nm.
The material of the hole transport layer is preferably a material having high hole mobility, which enables holes to be transferred from the anode or the hole injection layer to the light emitting layer. The hole transporting material may be a styrene compound such as a phthalocyanine derivative, a triazole derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative, an oxadiazole derivative, a hydrazone derivative, a stilbene derivative, a pyridinine derivative, a polysilane derivative, an imidazole derivative, a phenylenediamine derivative, an amino-substituted quininone derivative, a styrylanthracene derivative, a styrylamine derivative, a fluorene derivative, a spirofluorene derivative, a silazane derivative, an aniline copolymer, a porphyrin compound, a carbazole derivative, a polyarylalkane derivative, a polyphenylene ethylene and a derivative thereof, a polythiophene and a derivative thereof, a poly-N-vinylcarbazole derivative, a conductive polymer oligomer such as a thiophene oligomer, an aromatic tertiary amine compound, a styrylamine compound, a triamine, a tetramine, a biphenylamine, a propyne derivative, a p-phenylenediamine derivative, a m-phenylenediamine derivative, 1 '-bis (4-diarylaminophenyl) cyclohexane, 4' -bis (diarylamino) biphenyls, bis [4- (diarylamino) phenyl ] methane, 4 '-bis (diarylamino) triphenylbiphenyl, 4' -bis (diarylamino) tris-biphenyl, 4 '-bis (diarylamino) diaryl) 4' -diaryl ] methane, 4 '-diaryl (diarylamino) 4' -diaryl ] methane, 4 '-diaryl ] diphenyl ether, bis (diarylamino-4' -diaryl) methane, or bis (diarylmethane, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes or 2, 2-diphenylvinyl compounds, etc.
The thickness of the hole transport layer of the present invention may be 5 to 200nm, preferably 10 to 180nm and more preferably 20 to 150nm.
The electron blocking layer requires that the triplet state (T1) energy level of the material is higher than the T1 energy level of the main body material in the light emitting layer, and can play a role in blocking the energy loss of the light emitting layer material; the HOMO energy level of the electron blocking layer material is between the HOMO energy level of the hole transport layer material and the HOMO energy level of the luminescent layer main body material, so that holes are injected into the luminescent layer from the positive electrode, and meanwhile, the electron blocking layer material is required to have high hole mobility, hole transport is facilitated, and the application power of the device is reduced; the LUMO energy level of the electron blocking layer material is higher than that of the host material of the light emitting layer, and plays a role in blocking electrons, that is, the electron blocking layer material is required to have a wide forbidden bandwidth (Eg). The electron blocking layer material satisfying the above conditions may be a triarylamine derivative, a fluorene derivative, a spirofluorene derivative, a dibenzofuran derivative, a carbazole derivative, or the like. Among them, triarylamine derivatives such as N4, N4-bis ([ 1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1,1':4',1 "-terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4' -diamine; spirofluorene derivatives such as N- ([ 1,1 '-diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9' -spirobifluorene-2-amine; dibenzofuran derivatives such as, but not limited to, N-di ([ 1,1' -biphenyl ] -4-yl) -3' - (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine.
According to the invention, the thickness of the electron blocking layer is 1 to 200nm, preferably 5 to 150nm and more preferably 10 to 100nm.
According to the invention, the light emitting layer is located between the first electrode and the second electrode. The material of the light emitting layer is a material capable of emitting visible light by receiving holes from the hole transporting region and electrons from the electron transporting region, respectively, and combining the received holes and electrons. The light emitting layer may include a host material and a dopant material. The host material and the guest material of the light-emitting layer of the organic electroluminescent device can be one or two of anthracene derivatives, quinoxaline derivatives, triazine and dibenzofuran derivatives, xanthone derivatives, diphenyl ketone derivatives, carbazole derivatives, pyridine derivatives and pyrimidine derivatives. The guest material can be pyrene derivative, boron derivative, flexo derivative, spirofluorene derivative, iridium complex or platinum complex.
The thickness of the light-emitting layer of the present invention may be 5 to 60nm, preferably 10 to 50nm, more preferably 20 to 40nm.
The hole blocking layer may be disposed over the light emitting layer. The triplet state (T1) energy level of the hole blocking layer material is higher than the T1 energy level of the luminescent layer main body material, so that the effect of blocking the energy loss of the luminescent layer material can be achieved; the HOMO energy level of the material is lower than that of the main body material of the luminescent layer, so that the hole blocking effect is achieved, and meanwhile, the hole blocking layer material is required to have high electron mobility, so that electron transmission is facilitated, and the application power of the device is reduced; the hole blocking layer material satisfying the above conditions may be triazine and dibenzofuran derivatives, azabenzene derivatives, and the like. Among them, triazine and dibenzofuran derivatives are preferable; but is not limited thereto.
The thickness of the hole blocking layer may be 5 to 60nm, preferably 5 to 40m, more preferably 5 to 20nm.
An electron transport layer may be disposed over 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. The electron transport layer comprises or consists of one or more organic compounds according to the invention comprising a triazine and a dibenzofuran. Preferably, the electron transport layer is composed of the organic compound of the present invention and other electron transport layer materials. More preferably, the other electron transport layer material is an electron transport material commonly used in the art. Most preferably, the electron transport layer consists of the organic compound of the present invention and Liq.
In the electron transport layer of the organic electroluminescent device according to the invention, the ratio of the organic compound according to the invention and the other electron transport layer material is 1:9 to 9:1, preferably 2:8 to 8:2, more preferably 4:6 to 6:4, most preferably 5:5.
As the electron transporting compound of the present invention, one or more of compound 1, compound 2, compound 10, compound 17, compound 23, compound 27, compound 37, compound 48, compound 54, compound 66, compound 73, compound 82, compound 97, compound 107, compound 121, compound 130, compound 137, compound 145, compound 153, compound 162, compound 170, compound 177, compound 186, compound 201, compound 217, compound 234, compound 249, compound 263, compound 266, and compound 275 are preferably used.
The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, more preferably 20 to 45nm.
In a preferred embodiment of the present invention, the electron injection layer material is preferably a material metal Yb having a low work function so that electrons are easily injected into the organic functional material layer. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, more preferably 0.8 to 1.5nm.
In one embodiment of the invention, the second electrode may be a cathode or an anode, as previously described. In the present invention, the second electrode is preferably used as the cathode. The material used to form the cathode may be a material having a low work function, such as a metal, an alloy, a conductive compound, or a mixture thereof. Non-limiting examples of cathode materials may include lithium (Li), ytterbium (Yb), magnesium (Mg), aluminum (Al), calcium (Ca), and aluminum-lithium (Al-Li), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The thickness of the cathode is generally 5 to 100nm, preferably 7 to 50nm and more preferably 10 to 25nm, depending on the material used.
Optionally, in order to improve the light-emitting efficiency of the organic electroluminescent device, a light coupling layer (i.e. CPL layer) may be further added on top of the second electrode (i.e. cathode) of the device. According to the optical absorption and refraction principles, the higher the refractive index of the CPL layer material is, the better the CPL layer material is, and the smaller the light absorption coefficient is, the better the CPL layer material is. Any material known in the art may be used as the CPL layer material, such as Alq3. The CPL layer typically has a thickness of 5-300nm, preferably 20-100nm and more preferably 40-80nm.
Optionally, the organic electroluminescent device may further comprise 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.
Method for preparing organic electroluminescent device
The present invention also relates to a method of manufacturing the above organic electroluminescent device, comprising sequentially laminating a first electrode, a plurality of organic thin film layers, and a second electrode on a substrate. Wherein the multi-layered organic thin film layer is formed by sequentially laminating a hole transport region, a light emitting layer, and an electron transport region, i.e., sequentially laminating a hole injection layer, a hole transport layer, and an electron blocking layer, on the first electrode from bottom to top, and sequentially laminating a hole blocking layer, an electron transport layer, and an electron injection layer, i.e., sequentially laminating a hole transport layer, an electron transport layer, and an electron injection layer, on the light emitting layer, from bottom to top. In addition, optionally, an optical Coupling (CPL) layer may also be laminated on the second electrode to increase the light extraction efficiency of the organic electroluminescent device.
As for lamination, 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. Wherein vacuum evaporation means heating and plating a material onto a substrate in a vacuum environment.
In the present invention, the layers are preferably formed using a vacuum evaporation process, wherein the layers can be formed at a temperature of about 100-500 ℃ and a vacuum of about 10-8-10-2 torr and aboutVacuum evaporation was performed at a rate of (2). Preferably, the temperature is 200-400 ℃, more preferably 250-300 ℃. The vacuum degree is preferably 10-6 to 10-2Torr, more preferably 10-5 to 10-3Torr. The rate is aboutMore preferably about
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, or may be used as a single layer by forming a film after mixing with another material, or may be a laminated structure between layers formed by forming a film alone, a laminated structure between layers formed by mixing, or a laminated structure between layers formed by forming a film alone and layers formed by mixing.
Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used in a generic and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art as the present disclosure proceeds, features, characteristics, and/or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics, and/or elements described in connection with other embodiments unless specifically indicated. Accordingly, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the application.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
Examples
I. Preparation of Compounds example
The present invention will be described in detail below with reference to the drawings and examples.
All materials and reactants in the examples below were purchased from medium energy saving wanrun stock.
Synthesis of intermediate C1
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of 4-bromodibenzo [ b, d ] furan-3-ol, 0.022mol of phenylboric acid and 0.06mol of K2CO3 were added, 100mL of a mixed solution of toluene, acetic acid and water was then added, and 0.0003mol of tetrakis (triphenylphosphine) palladium was then added, followed by stirring, heating and refluxing for reaction for 12 hours, sampling was performed, and the reaction was completed. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, and purifying with silica gel column to obtain compound Z-1 with HPLC purity of 99.05% and yield of 78.62%.
Into a 250mL three-necked flask, nitrogen gas was introduced, and 0.02mol of Z-1,0.06mol of K2CO3, 100mL of acetonitrile and 60mL of pure water were added, followed by stirring and mixing, followed by slowly dropwise addition of 0.02mol of perfluorobutylsulfonyl fluoride. Sampling point plate, reaction was completed, extracted with 100ml ethyl acetate, layered, the extract was dried over anhydrous magnesium sulfate, filtered, filtrate was distilled off with toluene: the petroleum ether=5:1 mixture was recrystallized to give compound Z-2 with hplc purity 98.65% and yield 82.31%.
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of Z-2,0.022mol of pinacol ester and 0.06mol of potassium acetate were added, 100mL of dioxane was added, and the mixture was heated and stirred, refluxed and reacted for 12 hours, and the reaction was completed at a sampling point. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, and purifying with silica gel column to obtain intermediate C1 with HPLC purity of 98.78% and yield of 76.52%. Elemental analysis (formula C24H23BO 3): theoretical value C,77.86; h,6.26; ; test value: c,77.82; h,6.30; LC-MS: measurement value: 371.24 ([ M+H ] +); accurate quality: 370.17.
Synthesis of intermediate C2
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of 4-bromodibenzo [ b, d ] furan-3-ol, 0.022mol of pyridin-2-yl boric acid and 0.06mol of K2CO3 were added, 100mL of a mixed solution of toluene, acetic acid and water was then added, and 0.0003mol of tetrakis (triphenylphosphine) palladium was then added, followed by stirring, heating and refluxing for reaction for 12 hours, and the reaction was completed at a sampling point plate. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, and purifying with silica gel column to obtain compound Z-3 with HPLC purity of 98.58% and yield of 76.58%.
Into a 250mL three-necked flask, nitrogen gas was introduced, and 0.02mol of Z-3,0.06mol of K2CO3, 100mL of acetonitrile and 60mL of pure water were added, followed by stirring and mixing, followed by slowly dropwise addition of 0.02mol of perfluorobutylsulfonyl fluoride. Sampling point plate, reaction was completed, extracted with 100ml ethyl acetate, layered, the extract was dried over anhydrous magnesium sulfate, filtered, filtrate was distilled off with toluene: the petroleum ether=5:1 mixture was recrystallized to give compound Z-4 with hplc purity 98.51% and yield 80.85%.
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of Z-4,0.022mol of pinacol ester and 0.06mol of potassium acetate were added, 100mL of dioxane was added, and the mixture was heated and stirred, refluxed and reacted for 12 hours, and the reaction was completed at a sampling point. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, and purifying with silica gel column to obtain intermediate C2 with HPLC purity of 98.65% and yield of 75.28%. Elemental analysis (formula C23H22BNO 3): theoretical value C,74.41; h,5.97; n,3.77; test value: c,74.44; h,5.95; n,3.80; LC-MS: measurement value: 372.30 ([ M+H ] +); accurate quality: 371.17.
Synthesis of intermediate C3
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of 4-bromodibenzo [ b, d ] furan-3-ol, 0.022mol of pyridin-3-yl boric acid and 0.06mol of K2CO3 were added, 100mL of a mixed solution of toluene, acetic acid and water was then added, and 0.0003mol of tetrakis (triphenylphosphine) palladium was then added, followed by stirring, heating and refluxing for reaction for 12 hours, and the reaction was completed at a sampling point plate. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, and purifying with silica gel column to obtain compound Z-5 with HPLC purity of 98.42% and yield of 73.85%.
Into a 250mL three-necked flask, nitrogen gas was introduced, and 0.02mol of Z-5,0.06mol of K2CO3, 100mL of acetonitrile and 60mL of pure water were added, followed by stirring and mixing, followed by slowly dropwise addition of 0.02mol of perfluorobutylsulfonyl fluoride. Sampling point plate, reaction was completed, extracted with 100ml ethyl acetate, layered, the extract was dried over anhydrous magnesium sulfate, filtered, filtrate was distilled off with toluene: the petroleum ether=5:1 mixture was recrystallized to give compound Z-6 with hplc purity 98.68% and yield 81.75%.
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of Z-6,0.022mol of pinacol ester and 0.06mol of potassium acetate were added, 100mL of dioxane was added, and the mixture was heated and stirred, refluxed and reacted for 12 hours, and the reaction was completed at a sampling point. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, and purifying with silica gel column to obtain intermediate C3 with HPLC purity of 98.74% and yield of 74.28%. Elemental analysis (formula C23H22BNO 3): theoretical value C,74.41; h,5.97; n,3.77; test value: c,74.40; h,5.93; n,3.81; LC-MS: measurement value: 372.22 ([ M+H ] +); accurate quality: 371.17.
Synthesis of intermediate C4
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of 4-bromodibenzo [ b, d ] furan-3-ol, 0.022mol of pyridin-4-yl boric acid and 0.06mol of K2CO3 were added, 100mL of a mixed solution of toluene, acetic acid and water was then added, and 0.0003mol of tetrakis (triphenylphosphine) palladium was then added, followed by stirring, heating and refluxing for reaction for 12 hours, and the reaction was completed at a sampling point plate. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, and purifying with silica gel column to obtain compound Z-7 with HPLC purity of 98.50% and yield of 74.26%.
Into a 250mL three-necked flask, nitrogen gas was introduced, and 0.02mol of Z-7,0.06mol of K2CO3, 100mL of acetonitrile and 60mL of pure water were added, followed by stirring and mixing, followed by slowly dropwise addition of 0.02mol of perfluorobutylsulfonyl fluoride. Sampling point plate, reaction was completed, extracted with 100ml ethyl acetate, layered, the extract was dried over anhydrous magnesium sulfate, filtered, filtrate was distilled off with toluene: the petroleum ether=5:1 mixture was recrystallized to give compound Z-8 with hplc purity of 98.35% and yield 83.05%.
Into a 250mL three-necked flask, nitrogen gas was introduced, 0.02mol of Z-8,0.022mol of pinacol ester and 0.06mol of potassium acetate were added, 100mL of dioxane was added, and the mixture was heated and stirred, refluxed and reacted for 12 hours, and the reaction was completed at a sampling point. Naturally cooling, extracting with 100ml ethyl acetate, layering, drying the extract with anhydrous magnesium sulfate, filtering, steaming the filtrate, purifying with silica gel column to obtain intermediate C4, with HPLC purity of 98.62% and yield of 73.85%. Elemental analysis (formula C23H22BNO 3): theoretical value C,74.41; h,5.97; n,3.77; test value: c,74.43; h,5.92; n,3.81; LC-MS: measurement value: 372.28 ([ M+H ] +); accurate quality: 371.17.
Example 1 preparation of Compound 1
Into a three-port flask, nitrogen was introduced, 0.022mol of A-1, 100ml DMF,0.02mol mol of intermediate C1 and 0.0002mol of palladium acetate were added, followed by stirring, then 0.03mol of aqueous solution of K3PO4 was added, and the reaction was heated and refluxed for 14 hours, and the reaction was completed by sampling a spot plate. Naturally cooling, pouring the reaction liquid into a 500ml beaker, adding 200ml distilled water, mechanically stirring for 30min, carrying out suction filtration on the mixed liquid, leaching a filter cake with 100ml distilled water for 2 times, and leaching with 100ml ethanol to obtain light yellow solid powder. Finally, the solid powder was taken up in methylene chloride: the petroleum ether=1:5 eluate was purified on a silica gel column to give intermediate D1 with HPLC purity 99.11% and yield 76.58%.
In a three-necked flask, nitrogen was introduced, 0.02mol of intermediate D1, 100ml DMF,0.02mol B-1,0.0002mol of palladium acetate was added, stirring was performed, then 0.03mol of aqueous K3PO4 solution was added, the reaction was performed under reflux with heating for 14 hours, and the reaction was completed at a sampling point. Naturally cooling, pouring the reaction liquid into a 500ml beaker, adding 200ml distilled water, mechanically stirring for 30min, carrying out suction filtration on the mixed liquid, leaching a filter cake with 100ml distilled water for 2 times, and leaching with 100ml ethanol to obtain light yellow solid powder. Finally, the solid powder was taken up in methylene chloride: the petroleum ether=1:5 eluate was purified on a silica gel column to give compound 1 with hplc purity 99.25% and yield 78.21%. Elemental analysis (C42H 29N 3O) theory: c,85.25; h,4.94; n,7.10; test value: c,85.26; h,4.90; n,7.12.LC-MS: measurement value: 592.38 ([ M+H ] +); accurate quality: 591.23.
The procedure of example 1 was repeated to synthesize the following compounds; wherein the reaction conditions were similar except that starting material a, starting material B and intermediate C as set forth in table 1 below were used:
TABLE 1
The nmr hydrogen spectrum data of the compounds prepared in the examples herein are shown in table 2:
TABLE 2
The organic compound of the present invention is used in a light-emitting device, and can be used as a host material of a light-emitting layer or an electron transport material. The HOMO/LUMO energy level, the glass transition temperature Tg, the decomposition temperature Td, the S1 energy level, the T1 energy level, the evaporation temperature and the electron mobility were measured for the inventive compound and the comparative compound, respectively, and the measurement results are shown in table 3.
TABLE 3 Table 3
Note 1: the singlet state energy level S1 and the triplet state energy level T1 are tested by a fluorescent-3 series fluorescence spectrometer of Horiba, the test condition of the material is toluene solution of 2 x10 -5 mol/L, wherein the test temperature of S1 is 25 ℃, and the test temperature of T1 is 77K. 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), tested as an atmospheric environment. When the vapor deposition temperature is 10 < -4 > Pa, the vapor deposition rate of the material is 1A/S. The electron mobility was measured using the time of flight (TOF) method, and the measuring equipment was CMM-250 for Japan spectroscopy. Eg, lumo=homo-Eg was tested by a double beam uv-vis spectrophotometer (beijing general purpose company, model: TU-1901).
It can also be seen from Table 3 that, compared with the comparative compound, the HOMO and LUMO levels and the S1 and triplet energy levels (T1.gtoreq.2.5 eV) of the present invention are comparable to the comparative compound, while Tg and Td are significantly higher than the comparative compound, but the evaporation temperature is significantly lower than the comparative compound, and thus the thermal stability and evaporation stability of the compound of the present invention are significantly better than the comparative compound. Furthermore, the electron mobility of the compounds of the invention is significantly higher than that of the comparative compounds, which suggests that the compounds of the invention are more suitable for use in device functional layers requiring electron transport, such as electron transport materials and light emitting layer host materials in organic electroluminescent devices.
In addition, the organic compound has more proper HOMO and LUMO energy levels and triplet state energy levels (T1 is more than or equal to 2.5 eV), can be used as a luminescent layer main body material or an electron transport material of an organic electroluminescent device, has good carrier mobility, and can effectively reduce device driving voltage. The glass transition temperature of the material is higher than 120 ℃, which shows that the material has good film stability and can inhibit crystallization of the material. And compared with the comparative material, the material has higher glass transition temperature and decomposition temperature, so that the evaporation thermal stability of the material is improved, and the working stability of a device prepared from the material is improved. Finally, the material has lower evaporation temperature, and the difference between the evaporation temperature and the decomposition temperature is further increased, so that the evaporation stability of the material can be effectively improved, and the industrial window of material evaporation is improved.
Device preparation examples
The effect of the compounds synthesized according to the present invention in the application as host materials and electron transport materials for light emitting layers in devices will be described in detail below with reference to device examples 1 to 34 and device comparative examples 1 to 3. Device examples 2-34 and device comparative examples 1-3 were identical in the fabrication process 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 host material or electron transport material of the light emitting layer in the device was changed, as compared with device example 1. The device stack structure is shown in table 4, and the performance test results of each device are shown in table 5.
The molecular structural formula of the related material is shown as follows:
Device example 1
The preparation process comprises the following steps:
as shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, the anode is ITO (15 nm)/Ag (150 nm)/ITO (15 nm), and the anode layer 2 is washed, i.e., alkali washing, pure water washing, drying are sequentially performed, and then ultraviolet-ozone washing is performed to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-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 and P-1 was 97:3. Next, HT-1 was evaporated to 138nm thickness as a hole transport layer 4. EB-1 was then evaporated to a thickness of 42nm as electron blocking layer 5. After the evaporation of the electron blocking material, a light emitting layer 6 of the OLED light emitting device is fabricated, which comprises h1:h2=1:1 (the mass ratio of H1 to H2 is 1:1 as a main material, GD-1 as a doping material, the doping material doping ratio is 6% by weight, and the light emitting layer film thickness is 40nm, after the evaporation of the light emitting layer 6, the vacuum evaporation of the compound 1 and the Liq is continued, the mass ratio of the compound 1 to the Liq is 1:1, the film thickness is 35nm, and this layer is an electron transport layer 7. On the electron transport layer 7, a Yb layer with the film thickness of 1nm is fabricated by a vacuum evaporation device, this layer is an electron injection layer 8. On the electron injection layer 8, a Mg: ag electrode layer with the film thickness of 15nm is fabricated by a vacuum evaporation device, the Mg/Ag mass ratio is 1:9, this layer is a cathode layer 9, and then a CPL-1 with the film thickness of 70nm is evaporated as an optical coupling layer 10 on this basis.
Device examples 2-34 and device comparative examples 1-3 were prepared in a similar manner to device example 1, and the substrates each used a transparent PI film, and the anodes each used ITO (15 nm)/Ag (150 nm)/ITO (15 nm), except that the parameters in table 4 below were used.
TABLE 4 Table 4
Device test examples
The devices prepared in II were tested for driving voltage, current efficiency, CIEx, CIEy and LT95 lifetime. The voltage, current efficiency, CIEx, CIEy were tested using an IVL (current-voltage-brightness) test system (fresco scientific instruments, su) with a current density of 10mA/cm2.LT95 refers to the time taken for the device brightness to decay to 95% of the initial brightness, and the current density at the time of testing is 20mA/cm2; the life test system is an EAS-62C type OLED device life tester of Japanese systems research company. The test results are shown in Table 5 below.
TABLE 5
As can be seen from the device test data results of table 5 above, the device driving voltage prepared using the compounds of the present invention as electron transport layer materials is significantly reduced, while at the same time the current efficiency is significantly improved, and the device lifetime is greatly prolonged, for example, by substantially more than 1.2 times that of the comparative device, as compared to the comparative device using ET-1, ET-2 and ET-3 as electron transport layer materials. Compared with the comparative example device 1 prepared by using H1 and H2 as the main materials of the light-emitting layer, the driving voltage of the device prepared by using H1 and the compound of the invention as the main materials of the light-emitting layer is also obviously reduced, the current efficiency is obviously improved, the service life is greatly prolonged, and the service life is basically prolonged by more than 1.2 times.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Claims (9)
1. An organic compound containing triazine and dibenzofuran, which is characterized in that the structure of the organic compound is shown as a general formula (1):
in the general formula (1),
Ar 1 is phenyl or pyridyl;
Ar 2 is phenyl, biphenyl, naphthyl, pyridyl, quinolinyl, or phenanthryl;
R is one of the formulas A-1 to A-8;
2. the organic compound according to claim 1, wherein the organic compound is represented by one of structures represented by general formulae (2) to (9);
In the general formulae (2) to (9),
Ar 1 is phenyl or pyridyl;
Ar 2 is phenyl, biphenyl, naphthyl, pyridyl, quinolyl or phenanthryl.
3. The compound according to claim 2, wherein the compound is represented by any one of structures represented by general formulae (10) to (41);
In the general formulae (10) to (41), ar 2 is independently represented by phenyl, biphenyl, naphthyl, pyridyl, quinolyl or phenanthryl.
4. The compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
5. an organic electroluminescent device comprising a first electrode, a second electrode, and a plurality of organic thin film layers between the first electrode and the second electrode, wherein the organic thin film layers comprise a light emitting layer and one or more of a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, and an electron injecting layer, characterized in that at least one of the organic thin film layers contains one or more organic compounds according to any one of claims 1 to 4.
6. The organic electroluminescent device according to claim 5, wherein the electron transport layer or the light emitting layer contains one or more organic compounds according to any one of claims 1 to 4.
7. The organic electroluminescent device of claim 5, wherein the electron transport layer further comprises other electron transport materials, preferably further comprising a compound lithium octahydroxyquinoline.
8. Use of an organic compound according to any one of claims 1 to 4 as an electron transport layer material in an organic electroluminescent device.
9. Use of the organic compound according to any one of claims 1 to 4 as a host material for a light-emitting layer in an organic electroluminescent device.
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| KR20200086233A (en) * | 2019-01-08 | 2020-07-16 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
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