CN113429399A - 芘类衍生物,发光器件材料及发光器件 - Google Patents
芘类衍生物,发光器件材料及发光器件 Download PDFInfo
- Publication number
- CN113429399A CN113429399A CN202110783161.2A CN202110783161A CN113429399A CN 113429399 A CN113429399 A CN 113429399A CN 202110783161 A CN202110783161 A CN 202110783161A CN 113429399 A CN113429399 A CN 113429399A
- Authority
- CN
- China
- Prior art keywords
- organic
- compound
- layer
- bis
- light emitting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 80
- 150000003220 pyrenes Chemical class 0.000 title claims abstract description 23
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 39
- 230000005525 hole transport Effects 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 230000005693 optoelectronics Effects 0.000 claims 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 229910052805 deuterium Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 238000013086 organic photovoltaic Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 130
- -1 anthraquinone compounds Chemical class 0.000 description 92
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 150000001875 compounds Chemical class 0.000 description 84
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 80
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 80
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 76
- 239000007787 solid Substances 0.000 description 76
- 238000004128 high performance liquid chromatography Methods 0.000 description 46
- 238000005160 1H NMR spectroscopy Methods 0.000 description 44
- 239000012300 argon atmosphere Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 230000015572 biosynthetic process Effects 0.000 description 38
- 229910000029 sodium carbonate Inorganic materials 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000000243 solution Substances 0.000 description 33
- 238000001816 cooling Methods 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 31
- 125000001309 chloro group Chemical group Cl* 0.000 description 31
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- 238000012360 testing method Methods 0.000 description 30
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 28
- 238000011156 evaluation Methods 0.000 description 27
- 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 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 8
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 239000002356 single layer Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- QHBSIFCKNJXCHA-UHFFFAOYSA-N (3-phenylquinoxalin-2-yl)boronic acid Chemical compound B(C1=NC2=CC=CC=C2N=C1C3=CC=CC=C3)(O)O QHBSIFCKNJXCHA-UHFFFAOYSA-N 0.000 description 5
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 5
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 5
- BGKHQCLJYVUKNB-UHFFFAOYSA-N (9,9-dimethylfluoren-1-yl)boronic acid Chemical compound C1=CC(B(O)O)=C2C(C)(C)C3=CC=CC=C3C2=C1 BGKHQCLJYVUKNB-UHFFFAOYSA-N 0.000 description 4
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 4
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 4
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- CLCTZVRHDOAUGJ-UHFFFAOYSA-N N-[4-(3-chloro-4-cyanophenoxy)cyclohexyl]-6-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl]piperazin-1-yl]methyl]piperidin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC2=C(C=C1N1CCN(CC3CCN(CC3)C3=CC=C(N=N3)C(=O)NC3CCC(CC3)OC3=CC(Cl)=C(C=C3)C#N)CC1)C(=O)N(C1CCC(=O)NC1=O)C2=O CLCTZVRHDOAUGJ-UHFFFAOYSA-N 0.000 description 4
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940126086 compound 21 Drugs 0.000 description 4
- 229940125851 compound 27 Drugs 0.000 description 4
- 229940127271 compound 49 Drugs 0.000 description 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 230000001376 precipitating effect Effects 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- GGUYHZZGZZAVDH-UHFFFAOYSA-N 1,3-benzoxazol-2-ylboronic acid Chemical compound C1=CC=C2OC(B(O)O)=NC2=C1 GGUYHZZGZZAVDH-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 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 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000005581 pyrene group Chemical group 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XSAOVBUSKVZIBE-UHFFFAOYSA-N (9-phenylcarbazol-2-yl)boronic acid Chemical compound C=1C(B(O)O)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 XSAOVBUSKVZIBE-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- ZULYCUDVOSSRCO-UHFFFAOYSA-N 2,7-dibromo-10h-phenothiazine Chemical compound BrC1=CC=C2NC3=CC(Br)=CC=C3SC2=C1 ZULYCUDVOSSRCO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound 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
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- FXXVSQMPDFKASP-UHFFFAOYSA-N (9-phenylcarbazol-2-yl)oxyboronic acid Chemical compound C1(=CC=CC=C1)N1C2=CC=CC=C2C=2C=CC(=CC1=2)OB(O)O FXXVSQMPDFKASP-UHFFFAOYSA-N 0.000 description 1
- QIXPSFYLBFVSII-UHFFFAOYSA-N (9-phenylcarbazol-4-yl)boronic acid Chemical compound C12=CC=CC=C2C=2C(B(O)O)=CC=CC=2N1C1=CC=CC=C1 QIXPSFYLBFVSII-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- KWIVRAVCZJXOQC-UHFFFAOYSA-N 3h-oxathiazole Chemical class N1SOC=C1 KWIVRAVCZJXOQC-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
- SLVPZMREUNSKLJ-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C4=C(OC=3C1=2)C=CC=C4B(O)O Chemical compound C1=CC=CC=2C=CC=3C4=C(OC=3C1=2)C=CC=C4B(O)O SLVPZMREUNSKLJ-UHFFFAOYSA-N 0.000 description 1
- XPPGGCUYFLQRQX-UHFFFAOYSA-N C1=CC=CC=2C=CC=3OC4=C(C3C12)C=CC=C4B(O)O Chemical compound C1=CC=CC=2C=CC=3OC4=C(C3C12)C=CC=C4B(O)O XPPGGCUYFLQRQX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910000976 Electrical steel Inorganic materials 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 150000001217 Terbium Chemical class 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 230000000903 blocking effect Effects 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- RWWUBXBYBPQIJI-UHFFFAOYSA-N cesium;quinolin-8-ol Chemical compound [Cs].C1=CN=C2C(O)=CC=CC2=C1 RWWUBXBYBPQIJI-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical class N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- MORCTKJOZRLKHC-UHFFFAOYSA-N lithium;oxoboron Chemical compound [Li].O=[B] MORCTKJOZRLKHC-UHFFFAOYSA-N 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
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NUKKJECKNMQDTA-UHFFFAOYSA-N naphtho[1,2-b][1]benzofuran-9-ylboronic acid Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=C(B(O)O)C=C1O2 NUKKJECKNMQDTA-UHFFFAOYSA-N 0.000 description 1
- RADCOZFZMZLBQU-UHFFFAOYSA-N naphtho[1,2-b][1]benzothiol-10-ylboronic acid Chemical compound OB(O)c1cccc2c3ccc4ccccc4c3sc12 RADCOZFZMZLBQU-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines 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
- 150000003057 platinum Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Abstract
本发明涉及有机发光元件用芘类衍生物、含有芘类衍生物的发光器件材料及发光器件,更具体而言,涉及一种具有优异的色纯度和高亮度及发光效率的可溶性有机化合物以及使用该化合物的OLED器件。其特征在于下述通式(1)
Description
技术领域
本发明涉及有机发光元件用芘类衍生物、含有芘衍生物的发光器件材料及发光器件,更具体而言,涉及一种具有优异的色纯度和高亮度及发光效率的可溶性有机化合物以及使用该化合物的OLED器件。
背景技术
有机电激发光二极管(Organic Light-Emitting Diode,简称为OLED)。该发光器件具有薄型且能在低驱动电压下高亮度发光以及能通过选择发光材料而进行多色发光的特征,因此倍受关注。
该研究自从由柯达公司的C.W.Tang等揭示有机薄膜元件能以高亮度发光以来,大量OLED行业研究人员对于其应用,做了很多研究和推进。有机薄膜发光器件被广泛应用在各种主显示屏等中,其实用化取得长足的进展。
尽管有机电致发光的研究进展非常迅速,但仍有很多亟待解决的问题,例如外量子效率(EQE)仍然需要提高,如何设计与合成出色纯度更高、高效电子传输/空穴阻挡新材料等等。对于有机电致发光器件来说,器件的发光量子效率是各种因素的综合反映,也是衡量器件品质的一个重要指标。
电致发光一般可以分为荧光发光和磷光发光。在荧光发光中,单线态激发状态的有机分子跃迁至基态,由此发出光。另一方面,在磷光发光中,三线态激发状态的有机分子跃迁至基态,由此发出光。
目前来看,部分有机电致发光材料由于其性能优秀,已经在商业上有所应用,但作为有机电致发光器件中的主体材料,除了三线态能级要高于客体材料,防止激子跃迁释放的能量逆传递以外,更重要的是具有良好的空穴迁移性能。目前,主体材料中同时具有高三线态能级和良好空穴迁移率的材料仍然缺乏。因此,如何设计新的性能更好的主体材料,一直是本领域技术人员亟待解决的问题。
发明内容
如上所述,设计新的性能更好的主体材料是现阶段需要解决的问题。
本发明的目的是提供一种有机发光元件用芘类衍生物、含有芘衍生物的发光器件材料及发光器件,更具体而言,涉及一种具有优异的色纯度和高亮度及发光效率的可溶性有机化合物以及使用该化合物的OLED器件。
本发明提供一种芘类衍生物,该化合物具有下述通式(1)
其中R1选自如下取代或未取代的取代基
其中,R2,R3选自如下取代或未取代的取代基
其中,R4,R5,R6,R7独立的选自氢、取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基、取代或未取代的C4~C30杂芳基、或者是它们的组合;
进一步的优选的方式是,所述的有机化合物独立地选自下列化合物
本发明还提供上述一种含芘类衍生物在有机发光器件中的应用。
优选的,所述有机发光器件包括阳极、阴极以及位于阳极与阴极之间的若干个有机功能层,所述的有机功能层含有所述的芘类衍生物。
本发明的有益效果:
本发明提供一种芘类衍生物,该芘类衍生物具有通式(1)所示结构,芘环结构具有中等的三线态能级,在芘环的两侧分别设计连接供电子基团和吸电子基团,使之成为双极性材料,材料的空穴传输能力和电子传输能力得到平衡,有利于提升器件性能。另外芘环良好的平面性利于分子间的堆积,有利于减少不必要的振动能量损失,实现高效的发光性能。本发明的芘类衍生物,制备方法简单,原料易得,能够满足工业化需求。
本发明所述的有机电致发光器件是包含有芘类衍生物的发光元件,该发光元件包含基板、第一电极、有机物层、第二电极以及覆盖层,优选的器件结构可包括基板,位于基板上的第一电极,位于第一电极上的有机物层,位于有机物层上的第二电极,以及位于第二电极外侧的覆盖层,本发明所述的第二电极外侧是指背离第一电极的一侧。
本发明所述的有机物层可以包含发光层、空穴注入层、空穴传输层、电子传输层、电子注入层作为有机物层的结构。所述的发光元件的有机物层可以由单层结构形成,也可以由层叠包含发光层,空穴注入层,空穴传输层,电子传输层,电子注入层在内的多层结构形成;同时,所述的有机物层还可以包含一层或多层结构,例如,所述的空穴传输层可以包含第一空穴传输层以及第二空穴传输层。在本发明的发光元件中,除了所述发光层包含有本发明所述的芘类衍生物外,其它层均可以使用现有公知技术的用于所述层的任何材料。
本发明的发光元件中,基板材料可选用典型的有机发光元件中使用的任何基板。可以是钠玻璃或无碱玻璃或者透明柔性基板,也可以是不透明材料如硅或不锈钢的基板,还可以是柔性聚酰亚胺薄膜。不同基板材料具有不同的性能,应用方向不同。作为本发明的空穴传输层,可通过将空穴传输材料的一种或二种以上层叠或混合的方法,或通过使用空穴传输材料和高分子粘合剂的混合物的方法来形成。空穴传输材料需要在施加了电场的电极之间高效率地传输来自正极的空穴,因此希望空穴注入效率高、能够高效率地传输注入的空穴。因此,要求空穴传输材料具有适当电离势,适当的能级并且具有大的空穴迁移率,进一步材料稳定性优异,制造及使用过程中不容易产生会成为陷阱的杂质。对满足这样的条件的物质,没有特别限定,例如可以是咔唑衍生物、三芳胺衍生物、联苯二胺衍生物、芴衍生物、酞菁类化合物、六腈六氮杂苯并菲类化合物、喹吖啶酮类化合物、苝衍生物、蒽醌类化合物、F4-TCNQ、聚苯胺、聚噻吩、聚乙烯咔唑等,但不限于此。
作为本发明的发光层材料,除了包含本发明提供的芘类衍生物,也可以使用和掺杂材料(也称客体材料),可包含多个掺杂材料。另外发光层可为单一的发光层,也可为横向或纵向叠加在一起的复合发光层。对于掺杂材料的种类选择,可以为荧光材料,也可以为磷光材料。对于掺杂材料的用量选择,优选0.1~70%质量,更优选为0.1~30质量%、进一步优选为1~30质量%、更进一步优选为1~20质量%、特别优选为1~10质量%。
可用于本发明的荧光掺杂材料可包括:稠合多环芳族衍生物、苯乙烯基胺衍生物、稠环胺衍生物、含硼化合物、吡咯衍生物、吲哚衍生物、咔唑衍生物等,但不限于此。可用于本发明的磷光掺杂材料可包括:重金属配合物、磷光发光性的稀土类金属配合物等,但不限于此。重金属配合物可举出例如铱配合物、铂配合物、锇配合物等;稀土类金属配合物可举出例如铽络合物、铕络合物等,但不限于此。作为本发明的电子传输材料,优选具备良好电子迁移率的物质,同时具备合适的HOMO和LUMO能级。可作为本发明的电子传输材料包括:金属配合物、氧杂噻唑衍生物、噁唑衍生物、二氮唑衍生物、氮杂苯衍生物、菲罗啉衍生物、二氮蒽衍生物、含硅杂环类化合物、含硼杂环类化合物、氰基类化合物、喹啉衍生物、苯并咪唑衍生物等,但不限于此。
作为本发明的电子注入材料,优选具有传输电子能力的物质,同时具有从阴极注入电子的效应,具有优异的薄膜形成能力。可作为本发明的电子注入材料包括:碱金属化合物,例如氧化锂、氟化锂、8-羟基喹啉锂、氧化锂硼、碳酸铯、8-羟基喹啉铯、硅酸钾、氟化钙、氧化钙、氟化镁、氧化镁;芴酮;含氮五元环衍生物,例如,噁唑衍生物、恶二唑衍生物、咪唑衍生物;金属配合物;蒽醌二甲烷、联苯醌、蒽酮衍生物等,但不限于此,这些化合物可以单独使用,也可与其他材料混合使用。作为本发明的阴极材料,优选具有低功函数的材料,以便容易地将电子注入有机层。可用于本发明的阴极材料包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、铝、银、锡、铅,或者它们的合金;以及多层材料,例如LiF/Al或LiO2/Al,但不限于此。
本发明所述的有机物层材料,它们在使用时,可单独成膜形成单层结构,也可和其他材料一起混合成膜形成单层结构,或者形成单独成膜的单层的层叠结构、混合成膜的单层的叠层结构、单独成膜的单层和混合成膜的单层的叠层结构,但不限于此。本发明所述的有机电致发光器件可以通过依次层叠上述的结构而制造。制造方法可使用干式成膜法、湿式成膜法等公知方法。作为干式成膜法的具体例,可举出真空蒸镀法、溅射法、等离子体法、离子电镀法等。作为湿式成膜法的具体例,可举出旋涂法、浸渍法、流延法、喷墨法等各种涂布法,但不限于此。本发明所述有机发光器件可广泛应用于面板显示、照明光源、柔性OLED、电子纸、有机太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
具体实施方式
上述通式(1)所示的芘类衍生物的合成可以使用已知的方法进行。例如,使用镍、钯等过渡金属的交叉偶合反应。其他合成方法是使用镁或锌等过渡金属的C-C,C-N偶联生成反应。上述反应,限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki,Buchwald反应。
本发明的芘类衍生物用以下实施例举例说明,但并不限于这些实施例举例的芘类衍生物和合成方法。
本发明的初始原料和溶剂购于国药,一些常用的OLED中间体类等产品购于国内的OLED中间体厂商;各种钯催化剂,配体等购于sigma-Aldrich公司。
1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定;HPLC数据使用岛津LC-20AD高效液相仪来测定。
实施例和比较例中使用物质为:
(化合物1)2-(1,8-双(二苯并[b,d]呋喃-3-基)芘-4-基)-3-苯基喹喔啉
(化合物21)2-(1-(9,9'-螺环[芴]-3-基)芘-4-基)-3-苯基喹喔啉
(化合物27)2-(1,8-双(9,9-二甲基-9H-芴-1-基)芘-4-基)-3-苯基喹喔啉
(化合物49)2,2'-(4-(3-苯基喹喔啉-2-基)芘-1,8-二基)双(9-苯基-9H-咔唑)
(化合物66)9-苯基-4-(8-苯基-4-(3-苯基喹喔啉-2-基)芘-1-基)-9H咔唑
(化合物108)2-(1-(苯并[b]萘酚[2,1-d]噻吩-10-基)-8-苯基芘-4-基)-3-苯基喹喔啉
(化合物135)3,3'-(4-(3-苯基喹啉-2-基)芘-1,8-二基)双(5-苯基-5H-苯并[b]咔唑)
(化合物156)2,2'-(4-(3-苯基喹喔啉-2-基)芘-1,8-二基)双(苯并[d]恶唑)
(化合物178)11,11'-(4-(3-苯基喹喔啉-2-基)芘-1,8-二基)双(11H-苯并[a]咔唑)
(化合物184)3,6-二(二苯并[b,d]呋喃-3-基)-10,12-二苯基菲[4,5]喹唑啉
(化合物201)10,12-二苯基-3,6-双(9-苯基-9H-咔唑-2-基)菲并[4,5]喹唑啉
(化合物235)3,6-双(苯并[b]萘酚[1,2-d]噻吩-8-基)-10,12-二苯基菲[4,5]喹唑啉
(化合物270)3,6-二(9H-咔唑-9-基)-10,12-二苯基菲并[4,5]喹唑啉
(化合物314)3,6-双(萘并[2,1-b]苯并呋喃-8-基)-10,11-二苯基菲[4,5]喹喔啉
(化合物347)2,2'-(10,11-二苯基菲[4,5-fgh]喹喔啉-3,6-二基)双(苯并[d]恶唑)
(化合物376)3,6-双(9,9-二甲基-9H-芴-1-基)菲并[4,5]吩嗪
(化合物381)3,6-双(9-苯基-9H-咔唑-2-基)菲[4,5]苯那嗪
(化合物396)3,6-双(萘并[1,2-b]苯并呋喃-9-基)菲并[4,5]吩嗪
(化合物406)2,7-二(二苯并[b,d]呋喃-2-基)-10,11-二苯基菲[4,5]喹喔啉
(化合物414)2-(9,9'-螺环[芴]-3-基)-10,11-二苯基菲[4,5]喹恶啉
(化合物417)2,7-双(9,9-二甲基-9H-芴-1-基)-10,11-二苯基菲[4,5]喹恶啉
(化合物424)10,11-二苯基-2,7-双(9-苯基-9H-咔唑-4-基)菲[4,5]喹恶啉
(化合物439)2-(萘酚[1,2-b]苯并呋喃-10-基)-7-(萘酚[1,2-b]苯并呋喃-7-基)-10,11-二苯基菲[4,5]喹喔啉
(化合物460)10,11-二苯基-2,7-双(11-苯基-11H-苯并[a]咔唑-10-基)菲[4,5]喹喔啉
(化合物482)10,11-二苯基-2,7-双(1-苯基-1H-苯并[d]咪唑-2-基)菲[4,5]喹喔啉
(化合物496)2,7-二(二苯并[b,d]呋喃-4-基)-10,12-二苯基菲[4,5]喹唑啉
(化合物500)2,7-双(9,9-二甲基-9H-芴-1-基)-10,12-二苯基菲并[4,5]喹唑啉
(化合物509)2,2'-(10,12-二苯基菲[4,5]喹唑啉-2,7-二基)双(苯并[d]恶唑)
(化合物523)2,7-二(9H-咔唑-9-基)-10,12-二苯基菲并[4,5]喹唑啉
实施例1
化合物1的合成
氩气氛围下,反应器中加入1,8-二溴-4-氯代芘39.4g(100mmol)、二苯并[b,d]呋喃-3-基硼酸42.3g(200mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到37.0g的3,3'-(4-氯芘-1,8-二基)二二苯并[b,d]呋喃,收率65%,HPLC纯度98.5%。
1HNMR(DMSO):δ8.52(d,1H),8.30(d,1H),8.15(d,2H),8.03~7.98(m,4H),7.82~7.76(m,4H),7.72~7.70(m,3H),7.54(m,2H),7.39~7.31(m,4H)
在氩气氛下,反应容器中加入3,3'-(4-氯芘-1,8-二基)二二苯并[b,d]呋喃56.9克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到55.4g化合物1,收率75%,HPLC纯度99.3%。
1HNMR(DMSO):δ8.61(s,1H),8.52(d,1H),8.30(d,1H),8.15(d,2H),8.03~7.98(m,6H),7.82~7.67(m,10H),7.59~7.54(m,3H),7.39~7.31(m,6H).
实施例2
化合物21的合成
氩气氛围下,反应器中加入1-溴-4-氯代芘31.6g(100mmol)、3-硼酸-9,9'-螺二芴36.0g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚800ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到38.6g的3-(4-氯代芘-1-基)-9,9'-螺环[芴],收率70%,HPLC纯度98.9%。
1HNMR(DMSO):δ8.30(d,1H),8.18~8.15(m,2H),8.07~8.04(m,2H),7.92~7.89(m,5H),7.74~7.68(m,4H),7.55(d,1H),7.45(m,2H),7.38(m,1H),7.28~7.27(m,5H)
在氩气氛下,反应容器中加入3-(4-氯代芘-1-基)-9,9'-螺环[芴]55.1克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到57.6g化合物21,收率80%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.61(s,1H),8.30(d,1H),8.18~8.15(m,2H),8.07~8.03(m,4H),7.92~7.89(m,5H),7.74~7.68(m,4H),7.55(d,1H),7.45(m,2H),7.38(m,1H),7.28~7.27(m,5H)实施例3
化合物27的合成
氩气氛围下,反应器中加入1,8-二溴-4-氯代芘39.4g(100mmol)、(9,9-二甲基-9H-芴-1-基)硼酸47.6g(200mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到44.1g的4-氯-1,8-双(9,9-二甲基-9H-芴-1-基)芘,收率71%,HPLC纯度98.8%。
1HNMR(DMSO):δ8.52(d,1H),8.30(d,1H),8.15(d,2H),8.00(m,2H),7.90(m,2H),7.72~7.68(m,5H),7.57~7.55(m,4H),7.38(m,2H),7.28(m,2H),1.69(s,12H).
在氩气氛下,反应容器中加入4-氯-1,8-双(9,9-二甲基-9H-芴-1-基)芘62.1克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到63.3g化合物27,收率80%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.61(s,1H),8.52(d,1H),8.30(d,1H),8.15(d,2H),8.03~8.00(m,4H),7.90(m,2H),7.80(m,2H),7.70~7.55(m,11H),7.38(m,2H),7.28(m,2H),1.69(s,12H).
实施例4
化合物49的合成
氩气氛围下,反应器中加入1,8-二溴-4-氯代芘39.4g(100mmol)、(9-苯基-9H-咔唑-2-基)硼酸57.4g(200mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到53.9g的2,2'-(4-氯芘-1,8-二基)双(9-苯基-9H-咔唑),收率75%,HPLC纯度99.1%。
1HNMR(DMSO):δ8.55~8.52(m,3H),8.31~8.30(m,3H),8.15(d,2H),8.00(m,2H),7.94~7.91(m,4H),7.74~7.70(m,5H),7.62~7.58(m,6H),7.50(m,4H),7.35(m,2H),7.16(m,2H).
在氩气氛下,反应容器中加入2,2'-(4-氯芘-1,8-二基)双(9-苯基-9H-咔唑)71.9克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到69.3g化合物49,收率78%,HPLC纯度99.4%。
1HNMR(DMSO):δ8.61(s,1H),8.55(d,2H),8.52(d,1H),8.31~8.30(m,3H),8.15(d,2H),8.03(m,2H),7.94~7.91(m,4H),7.80(m,2H),7.74~7.70(m,5H),7.62~7.58(m,6H),7.50(m,4H),7.35(m,2H),7.16(m,2H).
实施例5
化合物66的合成
氩气氛围下,反应器中加入1,8-二溴-4-氯代芘39.4g(100mmol)、苯硼酸12.1g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到21.9g的1-溴-4-氯-8-苯基芘,收率56%,HPLC纯度98.5%。
1HNMR(DMSO):δ8.52(d,1H),8.15(d,1H),8.00(s,2H),7.79(d,2H),7.72~7.70(m,3H),7.46~7.41(m,3H).
氩气氛围下,反应器中加入1-溴-4-氯-8-苯基芘39.1g(100mmol)、(9-苯基-9H-咔唑-4-基)硼酸28.7g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到33.8g的4-(4-氯-8-苯基芘-1-基)-9-苯基-9H-咔唑,收率61%,HPLC纯度98.8%。
1HNMR(DMSO):δ8.55~8.52(m,2H),8.30(d,1H),8.15(d,2H),7.94~7.91(m,2H),7.79~7.70(m,5H),7.68~7.62(m,3H),7.58(m,1H),7.56~7.50(m,3H),7.46~7.35(m,4H).
在氩气氛下,反应容器中加入4-(4-氯-8-苯基芘-1-基)-9-苯基-9H-咔唑55.4克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到57.9g化合物66,收率80%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.61(s,1H),8.55~8.52(m,2H),8.30(d,1H),8.15(d,2H),8.03(m,2H),7.94~7.91(m,4H),7.80(m,2H),7.74~7.70(m,5H),7.62~7.58(m,6H),7.50(m,4H),7.35(m,2H),7.16(m,2H).
实施例6
化合物108的合成
氩气氛围下,反应器中加入1,8-二溴-4-氯代芘39.4g(100mmol)、苯硼酸12.1g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到21.9g的1-溴-4-氯-8-苯基芘,收率56%,HPLC纯度98.5%。
1HNMR(DMSO):δ8.52(d,1H),8.15(d,1H),8.00(s,2H),7.79(d,2H),7.72~7.70(m,3H),7.46~7.41(m,3H).
氩气氛围下,反应器中加入1-溴-4-氯-8-苯基芘39.1g(100mmol)、苯并[b]萘并[2,1-d]噻吩-10-基硼酸27.8g(100mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到35.4g的10-(4-氯-8-苯并芘-1-基)苯并[b]萘酚[2,1-d]噻吩,收率65%,HPLC纯度98.9%。
1HNMR(DMSO):δ8.55~8.52(m,2H),8.32~8.30(m,2H),8.16~8.15(m,3H),8.05~8.01(m,2H),7.83~7.79(m,3H),7.72(m,1H),7.70(m,3H),7.64(m,2H)7.46~7.41(m,3H).
在氩气氛下,反应容器中加入10-(4-氯-8-苯并芘-1-基)苯并[b]萘酚[2,1-d]噻吩54.5克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到51.4g化合物108,收率72%,HPLC纯度99.4%。
1HNMR(DMSO):δ8.61(s,1H),8.55~8.52(m,2H),8.30(d,1H),8.16~8.15(m,3H),8.05~8.01(m,4H),7.83(m,1H),7.80~7.79(m,4H),7.70(m,3H),7.67~7.64(m,4H),7.59(m,1H),7.46~7.41(m,3H),7.32(m,2H).
实施例7
化合物135的合成
氩气氛围下,反应器中加入1,8-二溴-4-氯代芘39.4g(100mmol)、(5-苯基-5H-苯并[b]咔唑-3-基)硼酸67.4g(200mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到59.8g的3,3'-(4-氯代芘-1,8-二基)双(5-苯基-5H-苯并[b]咔唑),收率73%,HPLC纯度99.1%。
1HNMR(DMSO):δ8.62(d,2H),8.5(m,1H),8.30~8.28(m,3H),8.22(m,2H),8.15(m,2H),8.11(m,2H),7.75~7.70(m,7H),7.69~7.62(m,6H),7.58~7.55(m,4H),7.50(m,4H),7.40(s,2H).
在氩气氛下,反应容器中加入3,3'-(4-氯代芘-1,8-二基)双(5-苯基-5H-苯并[b]咔唑)81.9克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到77.1g化合物135,收率78%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.62(d,2H),8.52(m,1H),8.30~8.28(m,3H),8.22(m,2H),8.15(m,2H),8.11(m,2H),7.75~7.70(m,6H),7.69~7.62(m,8H),7.59(m,1H),7.58~7.55(m,4H),7.50(m,4H),7.40(s,2H).
实施例8
化合物156的合成
氩气氛围下,反应器中加入1,8-二溴-4-氯代芘39.4g(100mmol)、苯并[d]恶唑-2-基硼酸32.6g(200mmol)、四(三苯基膦)钯1.16g(1.0mmol)、1.5M碳酸钠水溶液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,得到35.8g的2,2'-(4-氯代芘-1,8-二基)双(苯并[d]恶唑,收率76%,HPLC纯度99.1%。
1HNMR(DMSO):δ8.52(d,1H),8.30(d,1H),8.15(d,2H),7.74~7.70(m,5H),7.38(m,4H).
在氩气氛下,反应容器中加入2,2'-(4-氯代芘-1,8-二基)双(苯并[d]恶唑47.1克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到46.7g化合物156,收率73%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.62(d,1H),8.52(m,1H),8.30(m,3H),8.15(d,2H),8.03(m,2H)7.80(m,2H),7.74~7.70(m,6H),7.67~7.59(m,3H),7.38(m,4H),7.32(m,2H)
实施例9
化合物178的合成
在氩气氛下,反应容器中加入叔丁醇钾26.9克(240mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%)1,8-二溴-4-氯代芘39.4g(100mmol),11H-苯并[a]咔唑43.4克(200mmol)和1000mL乙二醇二甲醚(DME),在80℃加热搅拌15小时。反应混合物冷却到室温,加入500ml水,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到53.3克11,11'-(4-氯代芘-1,8-二基)双(11H-苯并[a]咔唑,HPLC纯度99.3%,收率80%.
1HNMR(DMSO):δ8.55~8.51(m,4H),8.25(m,2H),8.12~8.11(m,4H),7.94(m,4H),7.72~7.70(m,5H),7.67(m,2H),7.57(m,2H),7.35(m,2H),7.16(m,2H).
在氩气氛下,反应容器中加入11,11'-(4-氯代芘-1,8-二基)双(11H-苯并[a]咔唑66.7克(100mmol),(3-苯基喹喔啉-2-基)硼酸30.0g(120mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到66.1g化合物178,收率79%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.61(d,1H),8.55(m,2H),8.51(m,2H),8.25(d,2H),8.12~8.11(m,4H)8.03(m,2H),7.94(m,4H),7.80(m,2H),7.72~7.70(m,5H),7.67(m,2H),7.57(m,2H),7.35(m,2H),7.16(m,2H)
实施例10
化合物184的合成
在氩气氛下,反应瓶中加入N-(1,8-二溴芘-4-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到47.9克3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉收率84%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.35(d,2H),8.00(s,4H),7.80(m,2H),7.70~7.65(m,4H),7.50~7.49(m,4H)
在氩气氛下,反应容器中加入3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉56.4g(100mmol),二苯并[b,d]呋喃-3-基硼酸42.4克,[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%)(200mmol),1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到58.3克184,HPLC纯度99.6%,收率79%.
1HNMR(DMSO):δ8.35(m,2H),8.15(d,2H),8.06(m,2H),8.03(m,2H),7.98(m,2H),7.82(m,2H),7.80(m,2H),7.76(m,2H),7.70(m,2H),7.65(m,2H),7.54(m,2H)7.50(m,3H),7.49(m,1H),7.39(m,2H),7.31(m,2H).
实施例11
化合物201的合成
在氩气氛下,反应瓶中加入N-(1,8-二溴芘-4-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到47.9克3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉收率84%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.35(d,2H),8.00(s,4H),7.80(m,2H),7.70~7.65(m,4H),7.50~7.49(m,4H)
在氩气氛下,反应容器中加入3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉56.4g(100mmol),(9-苯基-9H-咔唑-2-基)硼酸57.4克(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%),1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到75.5克201,HPLC纯度99.7%,收率85%.
1HNMR(DMSO):δ8.55(m,2H),8.35(m,2H),8.31(m,2H),8.15(d,2H),8.06(d,2H),7.94~7.91(m,4H),7.80(m,2H),7.74(m,2H),7.70(m,2H),7.65~7.62(m,6H),7.58(m,2H),7.50(m,7H),7.35(m,2H),7.16(m,2H).
实施例12
化合物235的合成
在氩气氛下,反应瓶中加入N-(1,8-二溴芘-4-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到47.9克3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉收率84%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.35(d,2H),8.00(s,4H),7.80(m,2H),7.70~7.65(m,4H),7.50~7.49(m,4H)
在氩气氛下,反应容器中加入3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉56.4g(100mmol),苯并[b]萘酚[1,2-d]噻吩-8-基硼酸55.6克(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%)1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到72.3克235,HPLC纯度99.5%,收率83%.
1HNMR(DMSO):δ8.55~8.54(m,4H),8.35~8.32(m,4H),8.15(d,2H),8.06(m,2H),7.99(m,2H),7.80(m,4H),7.78(m,2H),7.70(m,4H),7.65(m,2H),7.61(m,2H),7.53(m,2H),7.50(m,3H).
实施例13
化合物270的合成
在氩气氛下,反应瓶中加入N-(1,8-二溴芘-4-基)苯甲酰胺50.5克(100mmol)和2-氯吡啶12.5克(120mmol)二氯甲烷300ml,降温至-78℃,然后加入三氟甲基磺酸酐31.0克(110mmol),将反应混合物置于冰水浴中并加热至0℃.加入苯甲腈11克(110mmol)。将反应混合物加热到45℃,反应6小时,冷却至室温加入三乙胺中和三氟甲烷磺酸盐。减压去除挥发物,采用闪蒸柱层析法(洗脱液:己烷中10%乙酸乙酯),得到47.9克3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉收率84%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.35(d,2H),8.00(s,4H),7.80(m,2H),7.70~7.65(m,4H),7.50~7.49(m,4H)
在氩气氛下,反应容器中加入1,8-二溴-4-氯代芘39.4g(100mmol),咔唑33.4克(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%),1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到58.9克270,HPLC纯度99.4%,收率80%.
1HNMR(DMSO):δ8.55(m,2H),8.35(m,2H),8.25(m,2H),8.19(m,2H),7.94(m,4H),7.80(m,2H),7.70(m,2H),7.65(m,2H),7.58(m,2H),7.50(m,5H),7.49(m,1H),7.35(m,2H),7.20(m,2H),7.16(m,2H).
实施例14
化合物314的合成
在氩气氛下,反应容器中加入3,6-二溴-10,11-二苯基菲[4,5-fgh]喹喔啉56.4克(100mmol),萘并[2,1-b]苯并呋喃-8-基硼酸52.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到72.1g化合物314,收率86%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.54(d,2H),8.15(d,2H),8.08~8.06(m,4H),8.03~8.02(m,6H),7.99(m,2H),7.70(s,2H),7.61~7.60(m,4H),7.59(m,2H),7.54~7.53(m,4H),7.51(m,2H),7.32(m,4H).
实施例15
化合物347的合成
在氩气氛下,反应容器中加入3,6-二溴-10,11-二苯基菲[4,5-fgh]喹喔啉56.4克(100mmol),苯并[d]恶唑-2-基硼酸32.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到57.0g化合物347,收率89%,HPLC纯度99.3%。
1HNMR(DMSO):δ8.30(d,2H),8.15(d,2H),8.03(m,4H),7.74~7.70(m,4H),7.59(m,2H),7.38(m,4H),7.32(m,4H)
实施例16
化合物376的合成
在氩气氛下,反应容器中加入3,6-二溴吩噻并[4,5-abc]吩嗪46.2克(100mmol),(9,9-二甲基-9H-芴-1-基)硼酸47.6g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到57.2g化合物376,收率83%,HPLC纯度99.3%。
1HNMR(DMSO):δ8.15(d,2H),8.06(m,2H),8.00(m,4H),7.90(d,2H),7.80(d,2H),7.70~7.67(m,6H),7.57~7.55(m,4H),7.38(m,2H),7.28(m,2H),1.69(s,12H).
实施例17
化合物381的合成
在氩气氛下,反应容器中加入3,6-二溴吩噻并[4,5-abc]吩嗪46.2克(100mmol),(9-苯基-9H-咔唑-2-基)硼酸57.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到68.4g化合物381,收率87%,HPLC纯度99.3%。
1HNMR(DMSO):δ8.55(d,2H),8.31(d,2H),8.15(d,4H),8.06(d,2H),7.80(m,2H)7.94~7.91(m,4H),7.74~7.70(m,4H),7.67(m,2H),7.62~7.58(m,6H),7.50(m,4H),7.35(m,2H),7.16(m,2H).
实施例18
化合物396的合成
在氩气氛下,反应容器中加入3,6-二溴吩噻并[4,5-abc]吩嗪46.2克(100mmol),萘并[1,2-b]苯并呋喃-9-基硼酸52.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到59.7g化合物396,收率81%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.16~8.11(m,6H),8.06(m,2H),8.03(m,2H),7.84~7.82(m,4H)7.80(d,2H),7.76(d,2H),7.70(s,2H),7.69(m,2H),7.67(m,4H),7.48(d,2H).
实施例19
化合物406的合成
在氩气氛下,反应容器中加入2,7-二溴吩噻并[4,5-abc]吩嗪46.2克(100mmol),二苯并[b,d]呋喃-2-基硼酸42.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到64.3g化合物406,收率87%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.46(s,2H),8.22(s,2H),8.03(m,4H),7.98(d,4H),7.92(s,2H)7.88(m,2H),7.83(d,2H),7.79(d,2H),7.59~7.54(m,4H),7.39(d,2H),7.32~7.31(m,6H).
实施例20
化合物414的合成
在氩气氛下,反应容器中加入2,7-二溴吩噻并[4,5-abc]吩嗪46.2克(100mmol),9,9'-螺环[芴]-3-基硼酸36.0g(100mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到56.9g化合物414,收率79%,HPLC纯度99.1%。
1HNMR(DMSO):δ8.46(s,1H),8.31(d,1H),8.22~8.18(m,2H),8.08(m,1H),8.04~8.03(m,5H),7.92~7.87(m,5H),7.74~7.68(m,2H),7.59~7.55(m,3H)7.45(m,2H),7.38(m,1H),7.32(m,4H),7.28~7.27(m,4H)
实施例21
化合物417的合成
在氩气氛下,反应容器中加入2,7-二溴-10,11-二苯基菲[4,5]喹恶啉56.4克(100mmol),(9,9-二甲基-9H-芴-1-基)硼酸47.6g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到66.4g化合物417,收率84%,HPLC纯度99.2%。
1HNMR(DMSO):δ8.46(s,2H),8.22(s,2H),8.03~8.00(m,6H),7.92~7.90(m,4H),7.68(m,2H),7.59~7.55(m,6H),7.38~7.28(m,8H),1.69(s,12H).
实施例22
化合物424的合成
在氩气氛下,反应容器中加入2,7-二溴-10,11-二苯基菲[4,5]喹恶啉56.4克(100mmol),(9-苯基-9H-咔唑-4-基)硼酸57.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到71.1g化合物424,收率80%,HPLC纯度99.4%。
1HNMR(DMSO):δ8.55(d,2H),8.46(s,2H),8.22(s,2H),8.03(m,4H),7.94~7.91(m,6H),7.68~7.62(m,6H),7.59~7.50(m,10H),7.35~7.32(m,6H),7.16(m,2H
实施例23
化合物439的合成
在氩气氛下,反应容器中加入2,7-二溴-10,11-二苯基菲[4,5]喹恶啉56.4克(100mmol),萘并[1,2-b]苯并呋喃-7-基硼酸52.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到71.3g化合物439,收率85%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.46(s,2H),8.22(s,2H),8.16~8.11(m,4H),8.03(m,4H),7.92(s,2H),7.84~7.82(m,4H),7.69~7.67(m,6H),7.59~7.57(m,4H),7.48(m,2H),7.32(m,4H).
实施例24
化合物460的合成
在氩气氛下,反应容器中加入2,7-二溴-10,11-二苯基菲[4,5]喹恶啉56.4克(100mmol),(11-苯基-11H-苯并[a]咔唑-10-基)硼酸67.4g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到83.1g化合物460,收率84%,HPLC纯度99.5%。
1HNMR(DMSO):δ8.65(d,2H),8.51~8.42(m,6H),8.22(s,2H),8.12~8.11(m,4H)8.03(m,4H),7.92(s,2H),7.72(d,2H),7.67~7.50(m,14H),7.59~7.57(m,4H),7.32(m,4H).
实施例25
化合物482的合成
在氩气氛下,反应容器中加入2,7-二溴-10,11-二苯基菲[4,5]喹恶啉56.4克(100mmol),(1-苯基-1H-苯并[d]咪唑-2-基)硼酸47.6g(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入500ml水,固体析出,过滤,得到的固体用乙醇洗涤,400ml甲苯重结晶得到64.1g化合物482,收率81%,HPLC纯度99.3%。
1HNMR(DMSO):δ8.56(m,2H),8.46(s,2H),8.22(s,2H),8.03(m,4H)8.03(m,4H),7.92(s,2H),7.81(d,2H),7.62(m,2H),7.59(m,2H),7.53(m,2H),7.48(m,4H),7.38(m,4H),7.32(m,4H).
实施例26
化合物496的合成
在氩气氛下,反应容器中加入3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉56.4g(100mmol),二苯并[b,d]呋喃-3-基硼酸42.4克(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%),1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到55.4克496,HPLC纯度99.6%,收率75%.
1HNMR(DMSO):δ8.46(s,2H),8.35(m,2H),8.22(s,2H),8.08~8.02(m,4H),7.98(d,2H),7.92(s,2H),7.80(d,2H),7.65(m,2H),7.54(m,2H),7.51~7.49(m,6H),7.39(m,2H),7.31(m,2H).
实施例27
化合物500的合成
在氩气氛下,反应容器中加入3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉56.4g(100mmol),(9,9-二甲基-9H-芴-1-基)硼酸47.6克(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%),1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到55.4克500,HPLC纯度99.6%,收率81%.
1HNMR(DMSO):δ8.46(s,2H),8.35(m,2H),8.22(s,2H),8.00(d,2H),,7.92(s,2H),7.90(d,2H),7.80(d,2H),7.68(d,2H),7.65(m,2H),7.57~7.55(m,4H),7.50(m,3H),7.38(m,2H),7.28(m,2H).
实施例28
化合物509的合成
在氩气氛下,反应容器中加入3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉56.4g(100mmol),苯并[d]恶唑-2-基硼酸32.4克(200mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%),1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,得到的固体用乙醇洗涤,500ml甲苯重结晶得到56.4克509,HPLC纯度99.6%,收率88%.
1HNMR(DMSO):δ8.46(s,2H),8.35(m,2H),8.22(s,2H),7.92(s,2H),7.80(d,2H),7.74(m,4H),7.65(m,2H),7.50~7.49(m,4H),7.38(m,4H).
实施例29
化合物523的合成
在氩气氛下,反应容器中加入叔丁醇钾26.9克(240mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%)3,6-二溴-10,12-二苯基菲并[4,5]喹唑啉56.4g(100mmol),咔唑33.4克(200mmol)和1000mL乙二醇二甲醚(DME),在80℃加热搅拌15小时。反应混合物冷却到室温,加入500ml水,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到63.4克523,HPLC纯度99.3%,收率86%.
1HNMR(DMSO):δ8.55(d,2H),8.35(m,2H),8.24(m,2H),8.19(m,2H),8.00(s,2H),7.94(d,2H),7.92(s,2H),7.80(m,2H),7.65(m,2H),7.58(m,2H),7.50~7.49(m,6H),7.35(m,2H),7.20(d,2H),7.16(d,2H).
器件实施方案
发光材料器件的评价
器件实施例中所用的各有机层化合物如下所示:
实施例30
器件制备方式:
器件的基本结构模型为:ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML:RD(Ir配合物)(40nm)=94:6/ETL(30nm)/LiF(1nm)/Al(80nm)
依次使用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
然后在真空气相蒸镀设备的衬底固定器上安装ITO衬底。在蒸镀设备中,控制体系压力在10-6托。向ITO衬底上蒸发厚度为60nm的空穴传输层材料HAT-CN。
然后蒸发厚度为40nm的发光层材料EML(化合物1),其中掺杂不同质量分数的RD金属铱配合物掺杂剂。
然后蒸发厚度为30nm的电子传输层材料ETL。
然后蒸发厚度为1nm的LiF为电子注入层。
最后蒸发厚度为80nm的Al作为阴极,利用玻璃封装盖对器件进行封装。
实施例31
除了EML材料为化合物21以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例32
除了EML材料为化合物27以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例33
除了EML材料为化合物49以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例34
除了EML材料为化合物66以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例35
除了EML材料为化合物108以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例36
除了EML材料为化合物135以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例37
除了EML材料为化合物156以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例38
除了EML材料为化合物178以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例39
除了EML材料为化合物184以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例40
除了EML材料为化合物201以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例41
除了EML材料为化合物235以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例42
除了EML材料为化合物270以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例43
除了EML材料为化合物314以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例44
除了EML材料为化合物347以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例45
除了EML材料为化合物376以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例46
除了EML材料为化合物381以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例47
除了EML材料为化合物396以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例48
除了EML材料为化合物406以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例49
除了EML材料为化合物414以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例50
除了EML材料为化合物417以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例51
除了EML材料为化合物424以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例52
除了EML材料为化合物439以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例53
除了EML材料为化合物460以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例54
除了EML材料为化合物482以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例55
除了EML材料为化合物496以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例56
除了EML材料为化合物500以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例57
除了EML材料为化合物509以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
实施例58
除了EML材料为化合物523以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
对比例1
除了EML材料为化合物RH-01以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
对比例2
除了EML材料为化合物RH-02以外,其余与实施例30作成相同的元件进行评价,测试结果见表1。
【表1】
器件结构除了发光层不同外,其它均一致,基于RH-01和RH-02的器件性能为参考,芘类衍生物的电流效率有了显著提升,,同时器件寿命也有所提升。综上所述,本发明所制备的新型芘类衍生物有机材料,在有机发光二极管上具有有较大的应用价值。
Claims (8)
3.一种有机光电器件,其特征在于,包括:
第一电极;
第二电极,与所述第一电极相面对;
有机功能层,夹设于所述第一电极和所述第二电极之间;
其中,有机功能层包含权利要求1-2中所述的有机化合物。
4.根据权利要求3所述的有机光电器件,其特征在于,有机光电器件为有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)及有机内存器件(Organic Memory Element)、照明和显示装置。
5.一种有机光电元件,包括阴极层、阳极层和有机层,该有机层包括空穴注入层、空穴传输层、发光层或活性层、电子注入层、电子传输层中至少一层,其特征在于:该器件的任一一层中含有权利要求1所述的有机化合物。
6.根据权利要求3或5所述的有机光电元件为有机电致发光器件,其特征在于,发光层中含有所述有机化合物和相应的客体材料,其中所述有机化合物的质量百分数在1%至99%,客体材料没有任何限制。
7.根据权利要求3至5所述的有机光电元件为有机电致发光器件,其特征在于,电子传输层中含有所述有机化合物,其中所述有机化合物的质量百分数在1%至100%。
8.一种显示或照明装置,其特征在于,所述的显示或照明装置含有权利要求3至7所述的有机光电元件。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110783161.2A CN113429399B (zh) | 2021-07-10 | 2021-07-10 | 芘类衍生物,发光器件材料及发光器件 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110783161.2A CN113429399B (zh) | 2021-07-10 | 2021-07-10 | 芘类衍生物,发光器件材料及发光器件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113429399A true CN113429399A (zh) | 2021-09-24 |
CN113429399B CN113429399B (zh) | 2024-03-26 |
Family
ID=77759966
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110783161.2A Active CN113429399B (zh) | 2021-07-10 | 2021-07-10 | 芘类衍生物,发光器件材料及发光器件 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113429399B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114292264A (zh) * | 2021-12-30 | 2022-04-08 | 广东工业大学 | 一种红色热活化延迟荧光材料、有机电致发光器件及其制备方法 |
US11527720B1 (en) | 2021-08-13 | 2022-12-13 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device, electronic device, and compound |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20090072152A (ko) * | 2007-12-28 | 2009-07-02 | 재단법인대구경북과학기술원 | 피렌 유도체 및 이를 이용한 유기전계발광소자 |
KR20110098646A (ko) * | 2010-02-26 | 2011-09-01 | 에스에프씨 주식회사 | 피렌계 화합물 및 이를 포함하는 유기전계발광소자 |
KR20130010594A (ko) * | 2011-07-19 | 2013-01-29 | (주)위델소재 | 파이렌 유도체 및 이를 이용한 유기전계 발광 소자 |
KR20160038309A (ko) * | 2014-09-30 | 2016-04-07 | (주)더블유에스 | 트리아졸기가 치환된 파이렌 유도체 및 이를 포함한 유기 전계발광 소자 |
CN107445929A (zh) * | 2017-08-09 | 2017-12-08 | 上海道亦化工科技有限公司 | 一种芘类有机电致发光化合物及其有机电致发光器件 |
CN107501218A (zh) * | 2017-08-09 | 2017-12-22 | 上海道亦化工科技有限公司 | 一种芘类有机电致发光化合物及其有机电致发光器件 |
CN108299388A (zh) * | 2017-12-26 | 2018-07-20 | 上海道亦化工科技有限公司 | 一种菲类衍生物及其用途和有机电致发光器件 |
CN108484507A (zh) * | 2018-04-04 | 2018-09-04 | 长春海谱润斯科技有限公司 | 一种芘类衍生物及其有机发光器件 |
CN108727389A (zh) * | 2017-04-21 | 2018-11-02 | 北京鼎材科技有限公司 | 芘衍生物及其在有机发光材料中的应用 |
-
2021
- 2021-07-10 CN CN202110783161.2A patent/CN113429399B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20090072152A (ko) * | 2007-12-28 | 2009-07-02 | 재단법인대구경북과학기술원 | 피렌 유도체 및 이를 이용한 유기전계발광소자 |
KR20110098646A (ko) * | 2010-02-26 | 2011-09-01 | 에스에프씨 주식회사 | 피렌계 화합물 및 이를 포함하는 유기전계발광소자 |
KR20130010594A (ko) * | 2011-07-19 | 2013-01-29 | (주)위델소재 | 파이렌 유도체 및 이를 이용한 유기전계 발광 소자 |
KR20160038309A (ko) * | 2014-09-30 | 2016-04-07 | (주)더블유에스 | 트리아졸기가 치환된 파이렌 유도체 및 이를 포함한 유기 전계발광 소자 |
CN108727389A (zh) * | 2017-04-21 | 2018-11-02 | 北京鼎材科技有限公司 | 芘衍生物及其在有机发光材料中的应用 |
CN107445929A (zh) * | 2017-08-09 | 2017-12-08 | 上海道亦化工科技有限公司 | 一种芘类有机电致发光化合物及其有机电致发光器件 |
CN107501218A (zh) * | 2017-08-09 | 2017-12-22 | 上海道亦化工科技有限公司 | 一种芘类有机电致发光化合物及其有机电致发光器件 |
CN108299388A (zh) * | 2017-12-26 | 2018-07-20 | 上海道亦化工科技有限公司 | 一种菲类衍生物及其用途和有机电致发光器件 |
CN108484507A (zh) * | 2018-04-04 | 2018-09-04 | 长春海谱润斯科技有限公司 | 一种芘类衍生物及其有机发光器件 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11527720B1 (en) | 2021-08-13 | 2022-12-13 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device, electronic device, and compound |
WO2023017704A1 (ja) * | 2021-08-13 | 2023-02-16 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子、電子機器及び化合物 |
CN114292264A (zh) * | 2021-12-30 | 2022-04-08 | 广东工业大学 | 一种红色热活化延迟荧光材料、有机电致发光器件及其制备方法 |
CN114292264B (zh) * | 2021-12-30 | 2023-11-10 | 广东工业大学 | 一种红色热活化延迟荧光材料、有机电致发光器件及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN113429399B (zh) | 2024-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6799174B2 (ja) | 有機発光素子および有機発光素子の有機物層用組成物 | |
CN112125872B (zh) | 杂环化合物和使用其的有机发光器件 | |
EP2719742B1 (en) | Novel compounds and organic electronic device using same | |
KR101029082B1 (ko) | 화합물 및 이를 이용한 유기전기소자, 그 전자장치 | |
KR101322828B1 (ko) | 유기화합물 및 이를 이용한 유기전기소자, 그 단말 | |
KR101053466B1 (ko) | 화합물 및 이를 이용한 유기전기소자, 그 전자장치, 내열성 측정법 | |
KR20130059265A (ko) | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 | |
KR101638665B1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
CN113402507B (zh) | 三亚苯衍生物,发光器件材料及发光器件 | |
KR20130093195A (ko) | 오원자 헤테로 고리를 포함하는 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 | |
CN113563871B (zh) | 主体材料、有机光电器件及显示或照明装置 | |
KR20130135516A (ko) | 벤조플루오렌을 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 | |
CN113429399B (zh) | 芘类衍生物,发光器件材料及发光器件 | |
CN115745977A (zh) | 一种电子传输材料及制备方法、有机电致发光器件 | |
KR101896009B1 (ko) | 인데노플루오렌을 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 | |
KR20130102669A (ko) | 사이클로 펜타 페난트렌을 포함하는 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 | |
KR20130101726A (ko) | 아크리딘 유도체를 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 | |
KR101298485B1 (ko) | 화합물 및 이를 이용한 유기전기소자, 그 단말 | |
CN113817462B (zh) | 主体材料、有机光电器件及显示或照明装置 | |
CN113717181B (zh) | 主体材料、有机光电器件及显示或照明装置 | |
CN114716418A (zh) | 杂环烷烃衍生物、有机光电器件和显示或照明装置 | |
CN113292514B (zh) | 一种哌嗪衍生物及包含其的有机光电器件 | |
CN113444097A (zh) | 三并咔唑衍生物、有机光电器件及显示或照明装置 | |
KR20130102428A (ko) | 아민 유도체를 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 | |
KR102580638B1 (ko) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |