CN115124495A - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
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- CN115124495A CN115124495A CN202110333375.XA CN202110333375A CN115124495A CN 115124495 A CN115124495 A CN 115124495A CN 202110333375 A CN202110333375 A CN 202110333375A CN 115124495 A CN115124495 A CN 115124495A
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- organic
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- phenyl
- organic compound
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- 239000000463 material Substances 0.000 claims abstract description 113
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 34
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000002347 injection Methods 0.000 claims description 37
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- 230000000903 blocking effect Effects 0.000 claims description 21
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- 239000010409 thin film Substances 0.000 claims description 13
- 239000002019 doping agent Substances 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004431 deuterium atom Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 abstract description 19
- 230000008020 evaporation Effects 0.000 abstract description 17
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 11
- 230000009477 glass transition Effects 0.000 abstract description 9
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- 125000005577 anthracene group Chemical group 0.000 abstract description 6
- 150000002987 phenanthrenes Chemical group 0.000 abstract description 2
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- 239000010410 layer Substances 0.000 description 144
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
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- 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 42
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- -1 amino-substituted quinone derivatives Chemical class 0.000 description 13
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
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- 230000000052 comparative effect Effects 0.000 description 10
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- 230000000694 effects Effects 0.000 description 9
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 8
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- 125000004986 diarylamino group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 125000005561 phenanthryl group Chemical group 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 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 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 5
- 235000010323 ascorbic acid Nutrition 0.000 description 5
- 229960005070 ascorbic acid Drugs 0.000 description 5
- 239000011668 ascorbic acid Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 235000011056 potassium acetate Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
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- 238000011160 research Methods 0.000 description 4
- 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 3
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 3
- JPBWZIPCMDZOPM-UHFFFAOYSA-N 2-(4-chlorophenyl)aniline Chemical group NC1=CC=CC=C1C1=CC=C(Cl)C=C1 JPBWZIPCMDZOPM-UHFFFAOYSA-N 0.000 description 3
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 3
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 3
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 3
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-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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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
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- 101710110702 Probable chorismate pyruvate-lyase 1 Proteins 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical compound C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 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 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 159000000006 cesium salts Chemical class 0.000 description 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- JOFBTOVNZIUWPX-UHFFFAOYSA-N dibenzofuran-1-ylboronic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2B(O)O JOFBTOVNZIUWPX-UHFFFAOYSA-N 0.000 description 1
- FQENSZQWKVWYPA-UHFFFAOYSA-N dibenzofuran-3-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3OC2=C1 FQENSZQWKVWYPA-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 238000005457 optimization Methods 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 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
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 238000011056 performance test Methods 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
- 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
- 230000001737 promoting effect Effects 0.000 description 1
- IQUNDDNVZDOOAB-UHFFFAOYSA-N prop-2-yne-1,1-diamine Chemical class NC(N)C#C IQUNDDNVZDOOAB-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 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
- 230000000171 quenching effect Effects 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-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
- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an organic compound and an organic electroluminescent device comprising the same, belonging to the technical field of semiconductor materials, wherein the structure of the organic compound is shown as a general formula (1); 9 and 10 positions of anthracene are respectively connected with a dibenzofuran derivative group and a phenyl or deuterated phenyl substituted phenanthrene group, the organic compound has higher glass transition temperature and molecular thermal stability, lower evaporation temperature, higher carrier mobility and proper HOMO energy level, and when the compound is used as a material of an organic electroluminescent device, the voltage and the efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to an organic compound and application thereof in an organic electroluminescent device.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various different functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting 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 OLED electroluminescence is generated.
Currently, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and will further expand to large-size application fields such as televisions, however, compared with actual product application requirements, the performance of the OLED device, such as light emitting efficiency and service life, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the light emitting material may be further classified into a host light emitting material and a dopant material. In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, a host material used as a light-emitting layer has good bipolar property, and an appropriate HOMO/LUMO energy level.
The main blue light host material mainly uses anthracene as a mother nucleus, because the anthracene mother nucleus material has good bipolar property, and can form triplet state-triplet state coupling correspondingly, thereby being beneficial to improving the efficiency of the device. However, the host material is not capable of achieving the device effects of low voltage, high efficiency and long life only by the anthracene core, and it is necessary to perform branch substitution on anthracene. Early substituent groups are mainly aryl groups, such as phenyl, biphenyl, naphthyl and the like, and the structure has higher driving voltage and higher power consumption of devices due to the lower carrier transport speed. And the film crystallinity and durability of the material have certain defects. At present, heteroaryl is introduced to 9 and 10 positions of anthracene of a host material, such as dibenzofuran, naphthofuran, benzimidazole and the like, and the structure has a higher carrier transmission rate and a higher glass transition temperature, so that the driving voltage of a device can be effectively reduced, and the service life of the device can be prolonged. Accordingly, the required properties of host materials are also increasing, and particularly, blue host materials are required not only to have good material stability but also to achieve good efficiency and lifetime at low driving voltage.
Since it is difficult to obtain a good balance among a driving voltage, device efficiency and lifetime of a host material of a light-emitting layer in the prior art, and there is a certain defect particularly in heat resistance and light durability of the material, it is a long-standing problem of material research to solve the above-mentioned problem of a host material for blue light.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides an organic compound, which has anthracene as a core, and has specific sites connected to a dibenzofuran derivative group and a phenyl or deuterated phenyl substituted phenanthrene group at positions 9 and 10, respectively, and has excellent heat resistance and light durability, and the organic compound can obtain a good balance among driving voltage, device efficiency and lifetime.
The technical scheme provided by the invention is as follows: an organic compound having a structure represented by general formula (1):
in the general formula (1), anthracene is connected with the position of '1' or '3' of the left dibenzofuran group;
R 1 ～R 5 each independently represents a hydrogen atom, a deuterium atom, a phenyl group or a deuterated phenyl group;
n represents 0,1, 2 or 3;
R 6 is represented by phenyl or deuterationA phenyl group.
The invention also provides an organic electroluminescent device which comprises an anode and a cathode, wherein a plurality of organic thin film layers are arranged between the anode and the cathode, and at least one organic thin film layer contains the organic compound.
The beneficial technical effects of the invention are as follows:
(1) the 9, 10-bit asymmetric substitution of anthracene can effectively destroy the symmetry of molecules, is favorable for inhibiting the plane accumulation of molecules, inhibiting the phase crystallization of material film, and improves the film stability and durability of the material.
(2) The anthracene is connected with the No. 1 position and the No. 3 position of the dibenzofuran, so that the space stereology of molecules can be improved, the interaction among molecules can be inhibited, the evaporation temperature of the material can be reduced, and the evaporation decomposition of the material can be inhibited; meanwhile, the 1 st position and the 3 rd position of dibenzofuran are connected with anthracene, so that delocalization and dispersion of electrons and holes in the whole molecule are facilitated, excessive concentration of the electrons and the holes is inhibited, the quenching effect of triplet excitons can be effectively inhibited, and the service life of the device is prolonged.
(3) The 2 or 3 position of the phenanthryl group is substituted by phenyl or deuterated phenyl, so that the material has good carrier mobility, particularly the electron mobility and the hole mobility are improved, and the driving voltage of a device can be effectively reduced; however, other sites except the 2-site and the 3-site of the phenanthrene are connected with anthracene, the mobility of the material is relatively low, and the voltage of the device is relatively high.
(4) The introduction of the substituted phenanthryl group containing phenyl or deuterated phenyl can improve the glass transition temperature of the material, inhibit the film crystallization of the material, and improve the thermal stability and durability of the material, thereby prolonging the service life of the device.
(5) After the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the driving voltage of the device can be effectively reduced, the service life of the device is prolonged, and the compound has a good application effect in the OLED light-emitting device and a good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
it comprises a substrate 1 and a substrate from bottom to top in sequence; 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. a light extraction 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 features in the embodiments and the embodiments of the present invention may be combined with each other without conflict. The invention is further described with reference to the following drawings and specific examples, which are not intended to be limiting.
In the present invention, unless otherwise specified, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule. Further, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between the energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level is, the lower the energy of the energy level is.
Any numerical range recited herein is intended to include all sub-ranges subsumed within the range with the same numerical precision. For example, "1.0 to 10.0" is intended to include all sub-ranges between (and including 1.0 and 10.0) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, all sub-ranges having a minimum value equal to or greater than 1.0 and a maximum value of equal to or less than 10.0. Any maximum numerical limitation recited herein is intended to include all smaller numerical limitations subsumed therein, and any minimum numerical limitation recited herein is intended to include all larger numerical limitations subsumed therein. Accordingly, applicants reserve the right to modify the specification, including the claims, to specifically describe any sub-ranges that fall within the ranges specifically described 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. In addition, 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 reference numerals refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, and other structures, "upper", "lower", "top", and "bottom" and the like used to indicate orientation only indicate orientation in a certain specific state, and do not mean that the related structures can exist only in the orientation; conversely, if the structure is repositioned, e.g., inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of the electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is further from the substrate is the "top" side.
An organic compound represented by the general formula (1):
in the general formula (1), anthracene is connected with the position of '1' or '3' of the left dibenzofuran group;
R 1 ～R 5 each independently represents a hydrogen atom, a deuterium atom, a phenyl group or a deuterated phenyl group;
n represents 0,1, 2 or 3;
R 6 represented as phenyl or deuterated phenyl.
Preferably, the organic compound has a structure represented by general formula (1-1) or general formula (1-2):
in the general formula (1-1) and the general formula (1-2), R 1 ～R 5 Independently represent a hydrogen atom, a deuterium atom, a phenyl group or a deuterated phenyl group;
n represents 0,1, 2 or 3;
R 6 represented as phenyl or deuterated phenyl.
Preferably, the compound is any one of structures represented by general formulas (1-3) to (1-6):
in the general formulae (1-3) to (1-6), R 1 ～R 5 Independently represent a hydrogen atom, a deuterium atom, a phenyl group or a deuterated phenyl group;
n represents 0,1, 2 or 3;
R 6 independently represent phenyl or deuterated phenyl.
In a preferred embodiment, the deuterated phenyl group can represent the following structure:
preferably, the specific structure of the organic compound is any one of the following structures:
organic electroluminescent device
The invention provides an organic electroluminescent device, which comprises an anode and a cathode, wherein a plurality of organic thin film layers are arranged between the anode and the cathode, and at least one organic thin film layer contains an organic compound shown in a general formula (1).
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
the organic electroluminescent device comprises a substrate 1 and a substrate from bottom to top in sequence; 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. a light extraction layer;
as the substrate of the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples are transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; flexible PI film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use varies depending on the nature 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 may be 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), Indium Tin Zinc Oxide (ITZO), or the like. When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include 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 50-500nm, preferably 70-300nm and more preferably 100-200 nm.
The organic functional material layer arranged between the first electrode and the second electrode sequentially comprises a hole transport region, a light emitting layer and an electron transport 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 materials of the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known materials used in OLED devices.
Examples of the above-mentioned materials may be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrylanthracene derivatives, styrylamine derivatives and other styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylenes and their derivatives, polythiophenes and their derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymer oligomers, aromatic tertiary amine compounds, styrene amine compounds, triamines, tetraamines, benzidine, propynediamine derivatives, hydrazone derivatives, stilbene derivatives, phenanthroline derivatives, and other derivatives, fluorine derivatives, and other derivatives, fluorine derivatives, and other compounds, fluorine derivatives, and fluorine, P-phenylenediamine derivatives, m-phenylenediamine derivatives, 1 '-bis (4-diarylaminophenyl) cyclohexane, 4' -bis (diarylamine) biphenyls, bis [4- (diarylamino) phenyl ] methanes, 4 '-bis (diarylamino) terphenyls, 4' -bis (diarylamino) quaterphenyls, 4 '-bis (diarylamino) diphenyl ethers, 4' -bis (diarylamino) diphenylsulfanes, bis [4- (diarylamino) phenyl ] dimethylmethanes, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes, 2-diphenylethylene compounds, and the like.
In a preferred embodiment of the present invention, the organic thin film layer includes a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and the electron blocking layer is a compound shown as follows:
furthermore, according to the matching requirements of the devices, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of 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 conducting film layer having the above-described various functions is not particularly limited.
The hole injection layer comprises a host organic material that conducts holes and a P-type dopant material having a deep HOMO level (and correspondingly 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 for conducting holes used in the anode interface buffer layer must have a certain characteristic with the P-doped material, so that it is expected that a charge transfer state between the host material and the doped material will occur, ohmic contact between the buffer layer and the anode will be achieved, and efficient injection from the electrode to hole injection conduction will be achieved.
In view of the above empirical summary, for the hole host materials with different HOMO levels, different P-doped materials need to be selected and matched to realize ohmic contact of the interface, so as to improve the hole injection effect.
Thus, in one embodiment of the present invention, for better hole injection, the hole injection layer further comprises a P-type dopant material with charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or a cyclopropane derivative, such as 4,4',4 "- ((1E,1' E, 1" E) -cyclopropane-1, 2, 3-trimethylenetri (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 dopant 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 the hole injection layer, the hole transport layer, and the electron blocking layer are formed, a corresponding light emitting layer is formed over the electron blocking layer.
The light emitting layer may include a host material using the organic compound represented by the general formula (1) of the present invention and a dopant material, which may be a blue dopant material that is conventional in the art.
In a preferred embodiment of the present invention, the light-emitting layer comprises a host material containing an organic compound represented by the general formula (1) and a dopant material which is:
in the light-emitting layer of the present invention, the ratio of the host material to the guest 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. A preferable range of the thickness is 5nm to 50nm, further preferably 10 to 50nm, and more preferably 15 to 30nm, but the thickness is not limited to this range.
In the present invention, the electron transport region may include, in order from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed over the light emitting layer, but is not limited thereto.
The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light emitting layer to the cathode, thereby extending the lifetime of the device and improving 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 having a hole-blocking effect known in the art can be used, 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-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives such as 9,9'- (5- (6- ([1,1' -biphenyl ] -4-yl) -2-phenylpyrimidin-4-yl) -1, 3-phenylene) bis (9H-carbazole) (CAS No. 1345338-69-3), 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;
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.
In a preferred embodiment of the present invention, the organic thin film layer includes a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and the electron transport layer is a compound shown as follows:
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/Al, Mg, BaF, Ba, Ag, or compounds or mixtures 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/Al, Mo, Ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20 nm.
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 layers 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 for preparing the 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, LITI, or the like may be used, but are not limited thereto. In the present invention, it is preferable that the respective layers are formed by a vacuum evaporation method. The individual process conditions in the vacuum evaporation process can be routinely selected by the person skilled in the art according to the actual requirements.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
The raw materials involved in the synthetic examples of the present invention are either commercially available or prepared by conventional preparation methods in the art;
synthesis of intermediate A-1:
to 150mL of Schlenk tube were added 2mmol of ascorbic acid, 20mmol of 4' -chloro-2-aminobiphenyl and 100mmol of phenylacetylene, followed by evacuation for 10 minutes and then by 3 replacements with dry nitrogen gas for 4 minutes each. Then, magnetic stirring was turned on, 20ml of DMSO was added by a syringe, and after completion of the addition, stirring was carried out for 5 minutes, and then 6mmol of n-butyl nitrite was slowly added through the syringe. After 12 hours at room temperature, the reaction was complete as determined by spot plate TLC. The reaction solution was diluted with 50ml of water, extracted with 50ml of ether, the combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure through a silica gel column to give 2-chloro-10-phenylphenanthrene, LC-MS: measurement value: 289.16([ M + H)] + ) (ii) a Accurate quality: 288.07.
in a 150ml three-necked flask, 10mmol of 2-chloro-10-phenylphenanthrene, 12mmol of pinacol ester, 0.05mol of Xphos, 0.05mol of (allyl) PdCl-Xphos, 22mmol of potassium acetate and 50ml of toluene were added, and the reaction was stirred at 35 ℃ for 3 hours under nitrogen. And (3) completely reacting the TLC raw material, cooling to room temperature, carrying out rotary evaporation on the reaction liquid, and passing through a silica gel column to obtain an intermediate A-1, LC-MS: measurement value: 381.25([ M + H)] + ) (ii) a Accurate quality: 380.19.
synthesis of intermediate A-2:
to 150mL of Schlenk tube was added 2mmol of ascorbic acid and 20mmol of 5-chloro [1,1' -biphenyl]-2-amine and 100mmol phenylacetylene, evacuated for 10 minutes and then replaced 3 times with dry nitrogen for 4 minutes each. Then, magnetic stirring was turned on, 20ml of DMSO was added by a syringe, and after completion of the addition, stirring was carried out for 5 minutes, and then 6mmol of n-butyl nitrite was slowly added through the syringe. After 14 hours at room temperature, the reaction was complete as determined by spot plate TLC. The reaction solution was poured into 50ml of waterAfter dilution, extraction with 50ml of ether was carried out, the combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, then subjected to reduced pressure distillation, and passed through a silica gel column to give 3-chloro-9-phenylphenanthrene, LC-MS: measurement value: 289.21([ M + H)] + ) (ii) a Accurate quality: 288.07.
in a 150ml three-necked flask, 10mmol of 3-chloro-9-phenylphenanthrene, 12mmol of pinacol ester, 0.05mol of Xphos, 0.05mol of (allyl) PdCl-Xphos, 22mmol of potassium acetate and 50ml of toluene were added, and the reaction was stirred at 35 ℃ for 4 hours under nitrogen. And (3) completely reacting the TLC raw material, cooling to room temperature, carrying out rotary evaporation on the reaction liquid, and passing through a silica gel column to obtain an intermediate A-2, LC-MS: measurement value: 381.32([ M + H)] + ) (ii) a Accurate quality: 380.19.
synthesis of intermediate A-3:
to 150mL of Schlenk tube were added 2mmol of ascorbic acid, 20mmol of 4' -chloro-2-aminobiphenyl and 100mmol of 1- ethynylbenzene 2,3,4,5,6-d5, and the mixture was evacuated for 10 minutes and then replaced with dry nitrogen for 3 times for 4 minutes each. Then, magnetic stirring was turned on, 20ml of DMSO was added by a syringe, and after completion of the addition, stirring was carried out for 5 minutes, and then 6mmol of n-butyl nitrite was slowly added through the syringe. After 13 hours at room temperature, the reaction was complete as determined by spot plate TLC. The reaction mixture was diluted with 50ml of water, extracted with 50ml of ether, the combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure through a silica gel column to give 2-chloro-10- (phenyl-d 5) phenanthrene, LC-MS: measurement value: 294.21([ M + H)] + ) (ii) a Accurate quality: 293.10.
in a 150ml three-necked flask, 10mmol of 2-chloro-10- (phenyl-d 5) phenanthrene, 12mmol of pinacol ester, 0.05mol of XPhos, 0.05mol of (allyl) PdCl-XPhos, 22mmol of potassium acetate and 50ml of toluene are added, and the reaction is stirred at 35 ℃ for 5 hours under nitrogen. Performing TLC (dot-thin-layer chromatography) on the spot plate to completely react, cooling to room temperature, performing rotary evaporation on reaction liquid, and passing through a silica gel column to obtain an intermediate A-3, LC-MS: measurement value: 386.40([ M + H)] + ) (ii) a Accurate quality: 385.23.
synthesis of intermediate A-4:
to 150mL of Schlenk tube was added 2mmol of ascorbic acid and 20mmol of 5-chloro [1,1' -biphenyl]-2-amine and 100mmol of 1- ethynylbenzene 2,3,4,5,6-d5, evacuated for 10 minutes and then replaced 3 times with dry nitrogen for 4 minutes each. Then, magnetic stirring was turned on, 20ml of DMSO was added by a syringe, and after completion of the addition, stirring was carried out for 5 minutes, and then 6mmol of n-butyl nitrite was slowly added through the syringe. After 15 hours at room temperature, the reaction was complete as determined by spot plate TLC. The reaction mixture was diluted with 50ml of water, extracted with 50ml of ether, the combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure through a silica gel column to give 3-chloro-9- (phenyl-d 5) phenanthrene, LC-MS: measurement value: 294.26([ M + H)] + ) (ii) a Accurate quality: 293.10.
in a 150ml three-necked flask, 3-chloro-9- (phenyl-d 5) phenanthrene, 12mmol pinacol ester, 0.05mol Xphos, 0.05mol (allyl) PdCl-Xphos, 22mmol potassium acetate and 50ml toluene were added, and the reaction was stirred at 35 ℃ for 5 hours under nitrogen. And (3) completely reacting the TLC raw material, cooling to room temperature, carrying out rotary evaporation on the reaction liquid, and passing through a silica gel column to obtain an intermediate A-4, LC-MS: measurement value: 386.31([ M + H)] + ) (ii) a Accurate quality: 385.23.
synthesis of intermediate A-5:
to 150mL of Schlenk tube were added 2mmol of ascorbic acid, 20mmol of 4' -chloro-2-aminobiphenyl and 100mmol of 1-ethynyl-4-d, followed by vacuum evacuation for 10 minutes and then 3 replacements with dry nitrogen gas for 4 minutes each. Then, magnetic stirring was turned on, 20ml of DMSO was added by syringe and droppedAfter the addition was complete, stirring was carried out for 5 minutes, and then 6mmol of n-butyl nitrite was slowly added via syringe. After 16 hours at room temperature, the reaction was complete as determined by spot plate TLC. The reaction solution was diluted with 50ml of water, extracted with 50ml of ether, the combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure through a silica gel column to give 2-chloro-10- (phenyl-4-d) phenanthrene, LC-MS: measurement value: 290.15([ M + H)] + ) (ii) a Accurate quality: 289.08.
in a 150ml three-necked flask, 10mmol of 2-chloro-10- (phenyl-4-d) phenanthrene, 12mmol of pinacol ester, 0.05mol of Xphos, 0.05mol of (allyl) PdCl-Xphos, 22mmol of potassium acetate and 50ml of toluene were added, and the reaction was stirred at 35 ℃ for 6 hours under nitrogen. And (3) completely reacting the TLC raw material, cooling to room temperature, carrying out rotary evaporation on the reaction liquid, and passing through a silica gel column to obtain an intermediate A-5, LC-MS: measurement value: 382.35([ M + H)] + ) (ii) a Accurate quality: 381.20.
synthesis of intermediate B-1:
in a 200ml three-necked flask, 10mmol of 9, 10-dibromoanthracene, 10mmol of dibenzofuran-3-boronic acid, 40ml of toluene, 40ml of ethanol, 40ml of water, 0.02mmol of tetrakis (triphenylphosphine) palladium, and 30mmol of sodium carbonate were added, and the mixture was purged with nitrogen for 5 minutes. Then, the mixture was mechanically stirred, heated to reflux, and reacted for 10 hours under heat. Then, plate TLC was spotted to confirm that 10mmol of 9, 10-dibromoanthracene as a starting material had reacted completely, and the reaction mixture was naturally cooled to room temperature. The reaction liquid was extracted 2 times with 50ml of ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, rotary evaporated, extracted with dichloromethane: passing the eluent with petroleum ether being 1:5 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain an intermediate B-1, LC-MS: measurement value: 423.18([ M + H)] + ) (ii) a Accurate quality: 422.03.
synthesis of intermediate B-2:
in a 200ml three-necked flask, 10mmol of 9, 10-dibromoanthracene, 10mmol of dibenzofuran-1-boronic acid, 40ml of toluene, 40ml of ethanol, 40ml of water, 0.02mmol of tetrakis (triphenylphosphine) palladium and 30mmol of sodium carbonate were added, and the mixture was purged with nitrogen for 5 minutes. Then, the mixture was mechanically stirred, heated to reflux, and reacted for 12 hours while maintaining the temperature. Then, plate TLC was spotted to confirm that 10mmol of 9, 10-dibromoanthracene as a starting material had reacted completely, and the reaction mixture was naturally cooled to room temperature. The reaction liquid was extracted 2 times with 50ml of ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, rotary evaporated, extracted with dichloromethane: passing the eluent with petroleum ether being 1:6 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain an intermediate B-2, LC-MS: measurement value: 423.23([ M + H)] + ) (ii) a Accurate quality: 422.03.
synthesis of intermediate B-3:
in a 200ml three-necked flask, 10mmol of 9, 10-dibromoanthracene and 10mmol of (7-phenyldibenzo [ b, d ] are charged]Furan-1-yl) boronic acid, 40ml of toluene, 40ml of ethanol, 40ml of water, 0.02mmol of tetrakis (triphenylphosphine) palladium, 30mmol of sodium carbonate, and replacement with nitrogen for 5 minutes. Subsequently, the mixture was mechanically stirred, heated to reflux and reacted for 13 hours while maintaining the temperature. Then, plate TLC was spotted to confirm that 10mmol of 9, 10-dibromoanthracene as a starting material had reacted completely, and the reaction mixture was naturally cooled to room temperature. The reaction liquid was extracted 2 times with 50ml of ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, rotary evaporated, washed with dichloromethane: passing the eluent with petroleum ether being 1:4 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain an intermediate B-3, LC-MS: measurement value: 499.25([ M + H)] + ) (ii) a Accurate quality: 498.06.
synthesis of intermediate B-4:
in a 200ml three-necked flask, 10mmol of 9, 10-dibromoanthracene and 10mmol of (9-phenyldibenzo [ b ]) were added，d]Furan-3-yl) boronic acid, 40ml of toluene, 40ml of ethanol, 40ml of water, 0.02mmol of tetrakis (triphenylphosphine) palladium, 30mmol of sodium carbonate, and replacement with nitrogen for 5 minutes. Then, the mixture was mechanically stirred, heated to reflux and reacted for 14 hours under heat. Then, plate TLC was spotted to confirm that 10mmol of 9, 10-dibromoanthracene as a starting material had reacted completely, and the reaction mixture was naturally cooled to room temperature. The reaction liquid was extracted 2 times with 50ml of ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, rotary evaporated, washed with dichloromethane: passing the eluent with petroleum ether being 1:3 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain an intermediate B-4, LC-MS: measurement value: 499.31([ M + H)] + ) (ii) a Accurate quality: 498.06.
synthesis of intermediate B-5:
in a 200ml three-necked flask, 10mmol of 9, 10-dibromoanthracene, 10mmol (dibenzo [ b, d ]) was added]Furan-1-yl-d 7) boronic acid, 40ml toluene, 40ml ethanol, 40ml water, 0.02mmol tetrakis (triphenylphosphine) palladium, 30mmol sodium carbonate, displacement with nitrogen for 5 minutes. Then, the mixture was mechanically stirred, heated to reflux, and reacted for 15 hours under heat. Then, plate TLC was spotted to confirm that 10mmol of 9, 10-dibromoanthracene as a starting material had reacted completely, and the reaction mixture was naturally cooled to room temperature. The reaction liquid was extracted 2 times with 50ml of ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, rotary evaporated, washed with dichloromethane: passing the eluent with the petroleum ether ratio of 1:5 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain an intermediate B-5, LC-MS: measurement value: 430.22([ M + H ]] + ) (ii) a Accurate quality: 429.07.
synthesis of intermediate B-6:
in a 200ml three-necked flask, 10mmol of 9, 10-dibromoanthracene, 10mmol (dibenzo [ b, d ]) was added]Furan-3-yl-d 7) boronic acid, 40ml toluene, 40ml ethanol, 40ml water, 0.02mmol tetrakis (triphenylphosphine) palladium, 30mmol sodium carbonate, displacement with nitrogen for 5 minutes. Subsequently, the mixture was mechanically stirred, heated to reflux and reacted for 13 hours while maintaining the temperature. Then, plate TLC was spotted to confirm that 10mmol of 9, 10-dibromoanthracene as a starting material had reacted completely, and the reaction mixture was naturally cooled to room temperature. The reaction liquid was extracted 2 times with 50ml of ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, rotary evaporated, washed with dichloromethane: passing the eluent with the petroleum ether ratio of 1:4 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain an intermediate B-6, LC-MS: measurement value: 430.31([ M + H)] + ) (ii) a Accurate quality: 429.07.
example 1: synthesis of Compound 1
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-1, 10mmol of intermediate B-1 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 16 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling, the mixture was extracted 2 times with 50ml of ethyl acetate, the organic phases were combined, the extract was dried over anhydrous magnesium sulfate, and the residue was extracted with dichloromethane: passing the eluent with the ratio of petroleum ether to 1:3 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain the compound 1. Elemental analysis Structure (C) 46 H 28 O) theoretical value: c, 92.59; h, 4.73; test values are: c, 92.62; h, 4.70. LC-MS: measurement value: 597.36([ M + H)] + ) (ii) a Accurate quality: 596.21.
example 2: synthesis of Compound 2
In a 250mL three-necked flask, nitrogen was purged and 11mmol of intermediate A-3, 10mmol of intermediate B-1 and 33mmol of K were added 2 CO 3 Adding a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water, introducing nitrogen for protection, adding 0.03mmol of tetrakis (triphenylphosphine) palladium, stirring, heating for reflux reaction for 18 hours, sampling spot plate TLC, and confirming the raw materialThe reaction was complete. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: passing the eluent at a ratio of 1:3 with petroleum ether through a silica gel column, and rotary evaporating the filtrate to obtain the compound 2. Elemental analysis Structure (C) 46 H 23 D 5 O) theoretical value: c, 91.82; h, 5.53; test values are: c, 91.81; h, 5.55. LC-MS: measurement value: 602.34([ M + H)] + ) (ii) a Accurate quality: 601.25.
example 3: synthesis of Compound 4
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-1, 10mmol of intermediate B-6 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 14 hours, and completion of the reaction of the starting material was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: passing the eluent with the ratio of petroleum ether to 1:5 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain the compound 4. Elemental analysis Structure (C) 46 H 21 D 7 O) theoretical value: c, 91.51; h, 5.84; (ii) a Test values are: c, 91.48; h, 5.86. LC-MS: measurement value: 604.19([ M + H)] + ) (ii) a Accurate quality: 603.26.
example 4: synthesis of Compound 6
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-1, 10mmol of intermediate B-2 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 15 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. Natural coolingExtracted 2 times with 50ml ethyl acetate, the organic phases are combined, the extracts are dried over anhydrous magnesium sulphate, the mixture is dried over dichloromethane: passing the eluent with the ratio of petroleum ether to 1:6 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain the compound 6. Elemental analysis Structure (C) 46 H 28 O) theoretical value: c, 92.59; h, 4.73; test values are: c, 92.58; h, 4.75. LC-MS: measurement value: 597.30([ M + H)] + ) (ii) a Accurate quality: 596.21.
example 5: synthesis of Compound 7
In a 250mL three-necked flask, nitrogen was purged and 11mmol of intermediate A-3, 10mmol of intermediate B-2 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 17 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: passing the eluent with the ratio of petroleum ether to 1:4 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain the compound 7. Elemental analysis Structure (C) 46 H 23 D 5 O) theoretical value: c, 91.82; h, 5.53; test values: c, 91.85; h, 5.50; . LC-MS: measurement value: 602.43([ M + H ]] + ) (ii) a Accurate quality: 601.25.
example 6: synthesis of Compound 9
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-1, 10mmol of intermediate B-5 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 15 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. Cooling naturally, extracting with 50ml ethyl acetate for 2 times, and mixingAnd the organic phase, the extract was dried over anhydrous magnesium sulfate, washed with dichloromethane: passing the eluent with the ratio of petroleum ether to 1:5 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain the compound 9. Elemental analysis Structure (C) 46 H 21 D 7 O) theoretical value: c, 91.51; h, 5.84; test values are: c, 91.53; h, 5.82; . LC-MS: measurement value: 604.38([ M + H ]] + ) (ii) a Accurate quality: 603.26.
example 7: synthesis of Compound 11
In a 250mL three-necked flask, nitrogen was purged and 11mmol of intermediate A-1, 10mmol of intermediate B-4 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 18 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: the eluent with petroleum ether ratio of 1:4 is passed through a silica gel column, and the filtrate is rotary evaporated to obtain the compound 11. Elemental analysis Structure (C) 52 H 32 O) theoretical value: c, 92.83; h, 4.79; test values are: c, 92.86; h, 4.77; . LC-MS: measurement value: 673.40([ M + H)] + ) (ii) a Accurate quality: 672.25.
example 8: synthesis of Compound 19
In a 250mL three-necked flask, nitrogen was purged and 11mmol of intermediate A-3, 10mmol of intermediate B-3 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was purged, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, followed by stirring and heating under reflux for 13 hours, and completion of the reaction of the starting material was confirmed by TLC on a sample plate. Cooling naturally, extracting with 50ml ethyl acetate for 2 times, mixing organic phases, and extracting with anhydrous waterDried over magnesium sulfate, with dichloromethane: the eluent containing 1:4 of petroleum ether was passed through a silica gel column, and the filtrate was rotary evaporated to give compound 19. Elemental analysis Structure (C) 52 H 27 D 5 O) theoretical value: c, 92.14; h, 5.50; test values: c, 92.16; h, 5.51; . LC-MS: measurement value: 678.42([ M + H)] + ) (ii) a Accurate quality: 677.28.
example 9: synthesis of Compound 42
In a 250mL three-necked flask, nitrogen was purged and 11mmol of intermediate A-2, 10mmol of intermediate B-1 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 16 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: passing the eluent with the ratio of petroleum ether to 1:5 through a silica gel column, and carrying out rotary evaporation on the filtrate to obtain the compound 42. Elemental analysis Structure (C) 46 H 28 O) theoretical value: c, 92.59; h,4.73 test value: c, 92.57; h, 4.75. LC-MS: measurement value: 597.38([ M + H)] + ) (ii) a Accurate quality: 596.21.
example 10: synthesis of Compound 43
In a 250mL three-necked flask, nitrogen was purged and 11mmol of intermediate A-4, 10mmol of intermediate B-1 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 14 hours, and completion of the reaction of the starting material was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane:the eluent containing 1:4 of petroleum ether was passed through a silica gel column, and the filtrate was rotary evaporated to give compound 43. Elemental analysis Structure (C) 46 H 23 D 5 O) theoretical value: c, 91.82; h,5.53 test value: c, 91.78; h, 5.55. LC-MS: measurement value: 602.47([ M + H)] + ) (ii) a Accurate quality: 601.25.
example 11: synthesis of Compound 45
In a 250mL three-necked flask, nitrogen was purged and 11mmol of intermediate A-2, 10mmol of intermediate B-6 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 15 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: the eluent with petroleum ether being 1:3 is passed through a silica gel column, and the filtrate is rotary evaporated to obtain the compound 45. Elemental analysis Structure (C) 46 H 21 D 7 O) theoretical value: c, 91.51; h,5.84 test value: c, 91.48; h, 5.87. LC-MS: measurement value: 604.53([ M + H)] + ) (ii) a Accurate quality: 603.26.
example 12: synthesis of Compound 48
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-2, 10mmol of intermediate B-2 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 17 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: 1:4 petroleum ether eluentSilica gel column, rotary evaporation of filtrate to obtain compound 48. Elemental analysis Structure (C) 46 H 28 O) theoretical value: c, 92.59; h,4.73 test value: c, 92.55; h, 4.77. LC-MS: measurement value: 597.44([ M + H)] + ) (ii) a Accurate quality: 596.21.
example 13: synthesis of Compound 49
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-4, 10mmol of intermediate B-2 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 13 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling, the mixture was extracted 2 times with 50ml of ethyl acetate, the organic phases were combined, the extract was dried over anhydrous magnesium sulfate, and the residue was extracted with dichloromethane: the eluent with petroleum ether ratio of 1:5 is passed through a silica gel column, and the filtrate is rotary evaporated to obtain the compound 49. Elemental analysis Structure (C) 46 H 23 D 5 O) theoretical value: c, 91.82; h,5.53 test value: c, 91.84; h, 5.50. LC-MS: measurement value: 602.41([ M + H)] + ) (ii) a Accurate quality: 601.25.
example 14: synthesis of Compound 51
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-2, 10mmol of intermediate B-5 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 14 hours, and completion of the reaction of the starting material was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: passing the eluent with the ratio of petroleum ether to 1:6 through a silica gel column, and rotatably evaporating the filtrate to obtain the compound51. Elemental analysis Structure (C) 46 H 21 D 7 O) theoretical value: c, 91.51; h, 5.84; test values: c, 91.47; h, 5.88. LC-MS: measurement value: 604.21([ M + H)] + ) (ii) a Accurate quality: 603.26.
example 15: synthesis of Compound 92
In a 250mL three-necked flask, nitrogen was bubbled and 11mmol of intermediate A-5, 10mmol of intermediate B-1 and 33mmol of K were added 2 CO 3 After a mixed solution of 40ml of toluene, 40ml of ethanol and 40ml of water was added and nitrogen gas was introduced for protection, 0.03mmol of tetrakis (triphenylphosphine) palladium was added thereto, the mixture was stirred and heated under reflux for 17 hours, and completion of the reaction of the starting materials was confirmed by TLC on a sample point plate. After cooling naturally, extraction was performed 2 times with 50ml of ethyl acetate, the organic phases were combined, and the extract was dried over anhydrous magnesium sulfate, extracted with dichloromethane: the eluent with petroleum ether being 1:5 is passed through a silica gel column, and the filtrate is rotary evaporated to obtain the compound 92. Elemental analysis Structure (C) 46 H 27 DO) theoretical value: c, 92.43; h, 4.89; test values: c, 92.46; h, 4.85; . LC-MS: measurement value: 597.39([ M + H)] + ) (ii) a Accurate quality: 596.22.
the organic compound of the present invention is used in a light-emitting device, and can be used as a material for a light-emitting layer. The HOMO level, glass transition temperature (Tg), decomposition temperature (Td), singlet level (S1) and evaporation temperature were measured for the inventive compound and the comparative compound, respectively, and the results are shown in Table 1.
TABLE 1
Note 1: the singlet energy level S1 was measured by the Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10 -5 A toluene solution of mol/mL; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi-Nachi Co.), with a heating rate of 10 ℃/min(ii) a The thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy testing system (IPS3) in an atmospheric environment. The temperature of the evaporation temperature is the temperature when the evaporation rate of the material is 1 angstrom/s under the vacuum degree of 10-4 pa. Hole/electron mobility: the materials were fabricated into single charge devices and tested by the space charge (induced) limited current method (SCLC), where the hole mobility and electron mobility of BH-1 were taken as the standard "100" and the data for the other materials as relative values.
The data in table 1 show that the compound of the present invention has suitable HOMO level and singlet level, and can be applied to a light emitting layer as a host material, and the glass transition temperature of the compound of the present invention is greater than 120 ℃, which indicates that the compound of the present invention has good film stability and durability. In addition, compared with a comparative material, the compound provided by the invention has a lower evaporation temperature, and the difference between the evaporation temperature and the decomposition temperature is large, so that the evaporation industrial window of the material can be effectively improved, and the evaporation thermal decomposition risk of the material can be reduced. Meanwhile, compared with a contrast material, the compound has higher glass transition temperature, can effectively inhibit crystallization of a material film in a phase state, and improves the durability of the material, thereby being beneficial to prolonging the service life of a device. Furthermore, compared with a contrast material, the compound provided by the invention has higher hole mobility and electron mobility, and is beneficial to improving the transmission rate of holes and electrons, so that the working voltage of the device is effectively reduced, and the power consumption of the device is reduced.
The effect of the compound synthesized by the present invention as a host material for a light emitting layer in a device is explained in detail by device examples 1 to 15 and device comparative examples 1 to 4 below. Device examples 2 to 15 and device comparative examples 1 to 4 were compared with device example 1, and the manufacturing processes of the devices were completely the same, and the same substrate material and electrode material were used, and the film thicknesses of the electrode materials were also kept the same, except that the host material of the light emitting layer in the device was changed. The device stack structure is shown in table 2, and the performance test results of each device are shown in table 3.
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, and the ITO (15nm)/Ag (150nm)/ITO (15nm) anode layer 2 is washed, i.e., sequentially washed with alkali, washed with pure water, dried, and then washed with ultraviolet-ozone 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 with a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to P-1 was 97: 3. HT-1 was then evaporated to a thickness of 140nm as hole transport layer 4. EB-1 was then evaporated to a thickness of 5nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, the light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the OLED light emitting device comprises that the OLED light emitting layer 6 uses the compound 1 as a main material, BD as a doping material, the doping proportion of the doping material is 3% by weight, and the thickness of the light emitting layer is 20 nm. After the light-emitting layer 6, ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 35nm, and this layer was an electron-transporting layer 7. On the electron transport layer 7, a Yb layer having a film thickness of 1nm was formed by a vacuum deposition apparatus, and this layer was an electron injection layer 8. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 13 nm-thick Mg: an Ag electrode layer, wherein the mass ratio of Mg to Ag is 1:9, and the Ag electrode layer is a cathode layer 9; then, CPL-1 was evaporated to 65nm as a light extraction layer 10.
After the electroluminescent device was fabricated according to the above procedure, the efficiency data and the light decay life of the device were measured, and the results are shown in table 3. The molecular structural formula of the related material is shown as follows:
TABLE 2
The devices were tested for drive voltage, current efficiency, CIEx, CIEy, and LT95 lifetimes. Voltage, Current efficiency, CIEx, CIEy were tested using the IVL (Current-Voltage-Brightness) test System (Fushida scientific instruments, Suzhou) at a current density of 10mA/cm 2 . LT95 refers to the time taken for the luminance of the device to decay to 95% of the initial luminance, with a current density of 50mA/cm under test 2 (ii) a The life test system is an EAS-62C type OLED device life tester of Japan systems research company. The efficiency and lifetime data for each device example and device comparative example are shown in table 3.
TABLE 3
| Numbering | Voltage (V) | Current efficiency (cd/A) | CIEx | CIEy | LT95(Hr) |
| Device comparative example 1 | 4.01 | 9.0 | 0.1392 | 0.0435 | 72 |
| Device comparative example 2 | 3.95 | 8.6 | 0.1395 | 0.0438 | 67 |
| Device comparative example 3 | 3.90 | 9.3 | 0.1394 | 0.0432 | 74 |
| Device comparative example 4 | 3.86 | 8.7 | 0.1398 | 0.0440 | 69 |
| Device example 1 | 3.63 | 9.0 | 0.1394 | 0.0438 | 80 |
| Device example 2 | 3.65 | 8.9 | 0.1401 | 0.0441 | 82 |
| Device example 3 | 3.61 | 9.2 | 0.1397 | 0.0442 | 85 |
| Device example 4 | 3.59 | 9.6 | 0.1401 | 0.0440 | 93 |
| Device example 5 | 3.64 | 9.4 | 0.1396 | 0.0445 | 90 |
| Device example 6 | 3.67 | 9.2 | 0.1397 | 0.0442 | 92 |
| Device example 7 | 3.70 | 9.0 | 0.1403 | 0.0439 | 92 |
| |
3.73 | 9.5 | 0.1405 | 0.0450 | 94 |
| Device example 9 | 3.62 | 9.6 | 0.1398 | 0.0445 | 88 |
| Device example 10 | 3.62 | 9.6 | 0.1400 | 0.0441 | 95 |
| Device example 11 | 3.58 | 9.5 | 0.1398 | 0.0437 | 87 |
| Device example 12 | 3.60 | 9.5 | 0.1396 | 0.0430 | 91 |
| Device example 13 | 3.72 | 9.2 | 0.1395 | 0.0442 | 87 |
| Device example 14 | 3.70 | 8.9 | 0.1404 | 0.0446 | 81 |
| Device example 15 | 3.66 | 9.3 | 0.1402 | 0.0439 | 82 |
To further illustrate the excellent heat and light durability of the inventive material, a single film heat and light test was performed on the inventive and comparative materials as shown in table 4 below:
TABLE 4
| Single film material | Initial purity (%) | Purity after Heat resistance (%) | Light fastness post purity (%) |
| |
99.80 | 99.75 | 99.77 |
| Compound 2 | 99.85 | 99.82 | 99.81 |
| |
99.92 | 99.88 | 99.87 |
| |
99.84 | 99.82 | 99.80 |
| |
99.93 | 99.90 | 99.91 |
| |
99.88 | 99.83 | 99.85 |
| Compound 11 | 99.78 | 99.75 | 99.74 |
| Compound 19 | 99.95 | 99.94 | 99.93 |
| Compound 42 | 99.96 | 99.92 | 99.89 |
| Compound 43 | 99.89 | 99.86 | 99.87 |
| Compound 45 | 99.86 | 99.81 | 99.83 |
| Compound 48 | 99.90 | 99.85 | 99.84 |
| Compound 49 | 99.97 | 99.96 | 99.95 |
| Compound 51 | 99.99 | 99.95 | 99.97 |
| Compound 92 | 99.91 | 99.87 | 99.86 |
| BH-1 | 99.88 | 99.08 | 98.92 |
| BH-2 | 99.92 | 99.12 | 99.03 |
| BH-3 | 99.90 | 98.86 | 98.90 |
| BH-4 | 99.95 | 98.79 | 98.82 |
Note 2: and (3) a heat-resistant durability experiment, namely putting 0.2g of sample into an ampoule bottle, then vacuumizing to 10-3pa, putting the ampoule bottle at the evaporation temperature of the material for heat resistance for 11 days, and taking out the material for HPLC test after the experiment is finished. In the illumination durability experiment, the material is evaporated on quartz glass by an evaporation mode to prepare a single mode, and then the single mode is packaged by a UV (ultraviolet) curing mode. And (3) placing the packaged wafer in xenon lamp aging equipment for light resistance Test, wherein the equipment is SUGA Test XT750, the humidity is set to be 40%, the environmental temperature is set to be 40 ℃, the irradiance is 700W/m2 (within the wavelength range of 400-800 nm), the illumination time is 5 days, and after the experiment is finished, taking out the wafer for HPLC Test.
As can be seen from the data results in tables 3 and 4, the organic light emitting device of the present invention has greatly improved driving voltage and device lifetime compared to the OLED device of the known host material, and particularly, the material of the present invention has great advantages in terms of heat resistance and light endurance of the material, so as to improve the working lifetime of the device.
Therefore, the asymmetric 9, 10-position anthracene substituted compound is constructed in the structure, so that the symmetry of the molecule can be effectively destroyed, and the membrane phase crystallization of the molecule can be inhibited. Meanwhile, phenyl or deuterated phenyl is introduced to replace phenanthryl and dibenzofuran groups, and the connecting site of dibenzofuran is adjusted, so that an unexpected technical effect is achieved. Specifically, the introduction of phenyl or deuterated phenyl substituted phenanthryl can improve the glass transition temperature of the material, further inhibit the crystallization of a molecular film, and improve the heat-resistant durability of the material, so that the service life of a device is prolonged; after the 1 or 3 position of the dibenzofuran is connected with the 9 or 10 position of the anthracene, the space interaction of molecules can be increased, the agglomeration or accumulation effect of materials is inhibited, the evaporation temperature of the materials is reduced, the evaporation industrial window of the materials is improved, the evaporation decomposition of the materials is inhibited, and the service life of a device is prolonged. Furthermore, 9 or 10 of anthracene are connected to 1 or 3 of dibenzofuran, are favorable to releiving of electron cloud, increase the tolerance in electron and hole, are favorable to improving carrier mobility to reduce device driving voltage, reduce the device consumption, be favorable to promoting device working life.
The compound of the invention is a compound which takes anthracene as a mother nucleus, 9-position anthracene is connected with 1 or 3-position of dibenzofuran, and 10-position anthracene is connected with phenyl or deuterated phenyl substituted phenanthryl, so that the compound is used as a main material to be applied to an OLED device, the voltage of the device is reduced by about 10%, the efficiency of the device is improved by about 20%, the service life of the device is improved by 30%, and the compound is unexpected for technicians in the field. Particularly, after 9 th position of anthracene is connected with 1 or 3 th position of dibenzofuran, the film crystallinity stability of the compound can be improved, the evaporation temperature of the material can be reduced, the electronic tolerance of the material can be improved, and the outstanding technical effects can be obtained. On the basis, after phenyl or deuterated phenyl substituted phenanthryl is introduced, the glass transition temperature of the material can be increased, the crystallization of a molecular film is further inhibited, the heat resistance and durability of the material are improved, and the service life of a device is prolonged. It is unexpected for those skilled in the art that the optimization and selection of the attachment site have led to a great breakthrough and progress in the performance of the material.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and should not be taken as limiting the scope of the present invention, which is intended to cover any modifications, equivalents, improvements, etc. within the spirit and scope of the present invention.
Claims (10)
1. An organic compound having a structure represented by general formula (1):
in the general formula (1), anthracene is connected with the position of '1' or '3' of the left dibenzofuran group;
R 1 ～R 5 each independently represents a hydrogen atom, a deuterium atom, a phenyl group or a deuterated phenyl group;
n represents 0,1, 2 or 3;
R 6 represented as phenyl or deuterated phenyl.
2. The organic compound according to claim 1, wherein the organic compound has a structure represented by general formula (1-1) or general formula (1-2):
in the general formula (1-1) and the general formula (1-2), R 1 ～R 5 Independently represent a hydrogen atom, a deuterium atom, a phenyl group or a deuterated phenyl group;
n represents 0,1, 2 or 3;
R 6 represented as phenyl or deuterated phenyl.
3. The organic compound according to claim 1, wherein the compound has any one of the structures represented by general formulae (1-3) to (1-6):
in the general formulae (1-3) to (1-6), R 1 ～R 5 Independently hydrogen atom, deuterium atom, phenyl or deuterated phenyl;
n represents 0,1, 2 or 3;
R 6 independently represent phenyl or deuterated phenyl.
4. The organic compound according to any one of claims 1 to 3, wherein the deuterated phenyl group can represent the following structure:
5. The organic compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
6. an organic electroluminescent device comprising an anode and a cathode with a plurality of organic thin film layers therebetween, wherein at least one of the organic thin film layers contains the organic compound according to any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the organic thin film layer comprises a light-emitting layer containing the organic compound according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 6, wherein the organic thin film layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a dopant material, the host material comprises the organic compound according to any one of claims 1 to 5, and the dopant material is:
9. the organic electroluminescent device as claimed in claim 8, wherein the organic thin film layer further comprises a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer and an electron injection layer, and the electron blocking layer is a compound of:
10. the organic electroluminescent device according to claim 8, wherein the organic thin film layer further comprises a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer and an electron injection layer, and the electron transport layer is a compound represented by the following formula:
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Address after: B312-194, No. 2 Fengwei Road, Huizhi Enterprise Center, Xishan Economic and Technological Development Zone, Xishan District, Wuxi City, Jiangsu Province, 214000 Applicant after: Jiangsu March Technology Co.,Ltd. Address before: 214112 No.210 Xinzhou Road, New District, Wuxi City, Jiangsu Province Applicant before: Jiangsu March Technology Co.,Ltd. |
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