CN108218722B - 新颖化合物及包含其的有机发光器件 - Google Patents
新颖化合物及包含其的有机发光器件 Download PDFInfo
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- CN108218722B CN108218722B CN201711325971.3A CN201711325971A CN108218722B CN 108218722 B CN108218722 B CN 108218722B CN 201711325971 A CN201711325971 A CN 201711325971A CN 108218722 B CN108218722 B CN 108218722B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 66
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 15
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000010410 layer Substances 0.000 claims description 80
- 239000000126 substance Substances 0.000 claims description 52
- 238000002347 injection Methods 0.000 claims description 29
- 239000007924 injection Substances 0.000 claims description 29
- 239000012044 organic layer Substances 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- -1 phenyl-substituted phenylene group Chemical group 0.000 abstract description 29
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 abstract description 3
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 abstract description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 abstract description 3
- 150000004982 aromatic amines Chemical class 0.000 abstract description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 125000005580 triphenylene group Chemical group 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 83
- 238000003786 synthesis reaction Methods 0.000 description 78
- 238000006243 chemical reaction Methods 0.000 description 32
- 238000000034 method Methods 0.000 description 25
- 239000000463 material Substances 0.000 description 23
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 238000001771 vacuum deposition Methods 0.000 description 11
- 238000000151 deposition Methods 0.000 description 9
- WNXNWOBGPRKOJF-UHFFFAOYSA-N 2-bromo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 WNXNWOBGPRKOJF-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000008021 deposition Effects 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 7
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000000203 mixture 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- 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 2
- 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 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 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 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
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- 125000001072 heteroaryl group Chemical group 0.000 description 2
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- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
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- HIHYAKDOWUFGBK-UHFFFAOYSA-N 1,3-dibromo-5-phenylbenzene Chemical group BrC1=CC(Br)=CC(C=2C=CC=CC=2)=C1 HIHYAKDOWUFGBK-UHFFFAOYSA-N 0.000 description 1
- LGYSGASOAOQCPG-UHFFFAOYSA-N 1-N,5-diphenyl-3-N,3-N-bis(4-phenylphenyl)benzene-1,3-diamine Chemical compound N(c1ccccc1)c1cc(cc(c1)-c1ccccc1)N(c1ccc(cc1)-c1ccccc1)c1ccc(cc1)-c1ccccc1 LGYSGASOAOQCPG-UHFFFAOYSA-N 0.000 description 1
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- PBWATBVKPGTOTB-UHFFFAOYSA-N 4-bromo-9,9-diphenylfluorene Chemical compound BrC1=CC=CC2=C1C1=CC=CC=C1C2(C=1C=CC=CC=1)C1=CC=CC=C1 PBWATBVKPGTOTB-UHFFFAOYSA-N 0.000 description 1
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 1
- GJXAVNQWIVUQOD-UHFFFAOYSA-N 4-bromodibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C(Br)=CC=C2 GJXAVNQWIVUQOD-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 150000001616 biphenylenes Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000005406 washing Methods 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
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Abstract
本发明涉及由苯基取代的亚苯基的双侧适用芳基胺的有机化合物,尤其是涉及在一侧导入二苯基芴、螺双芴、三亚苯、二苯并呋喃或二苯并噻吩的新颖化合物及包含其的有机发光器件。
Description
技术领域
本发明涉及新颖化合物及包含其的有机发光器件。
背景技术
在有机发光二极管中,用作有机物层的材料,按照功能,大体上可分为发光材料、空穴注入材料、空穴传输材料、电子传输材料、电子注入材料等。并且,上述发光材料按照分子量可分为高分子和低分子,按照发光机制可分为来源于电子的单重态激发态的荧光材料和来源于电子的三重态激发态的磷光材料,发光材料按照发光颜色,可分为蓝色、绿色、红色发光材料和为了呈现更好的天然色而所需的黄色及橙色发光材料。并且,为了增加色纯度,并通过能量转移来增加发光效率,可将主体/掺杂剂类用作发光物质。其原理在于,若将与主要构成发光层的主体相比能带隙小且发光效率优秀的少量掺杂剂混合于发光层,则主体中产生的激子向掺杂剂传输,从而发出效率高的光。此时,主体的波长向掺杂剂的波长范围移动,因而根据所利用的掺杂剂和主体的种类可获得所需波长的光。
至今,众所周知,这种有机发光器件中使用的物质有多种化合物,但在利用至今众所周知的物质的有机发光器件的情况下,由于高的驱动电压、低的效率及短寿命,需要持续开发新材料。因此,利用具有优秀的特性的物质,持续地努力开发具有低电压驱动、高亮度及长寿命的有机发光器件。
现有技术文献
专利文献
日本公开专利10-2015-530735
发明内容
本发明要提供新颖有机化合物及其制备方法以及包含其的有机发光器件。
但是,本发明要解决的问题不局限于以上描述的问题,未描述的另一问题将通过以下记载内容会让本发明所属技术领域的普通技术人员明确理解。
本发明的第一实施方式,提供由以下化学式1表示的化合物:
化学式1
在上述化学式1中,
Ar1为
Ar2至Ar4分别独立地表示苯基、联苯基或萘基,
L1及L2分别独立地表示直链,或者取代或未取代的C5-C30亚芳基,
在上述Ar1中,*意味着连接部位。
本发明的第二实施方式,提供包含本发明的化合物的有机发光器件。
本发明为由苯基取代的亚苯基的双侧适用芳基胺的有机化合物,尤其是在一侧导入二苯基芴、螺双芴、三亚苯、二苯并呋喃或二苯并噻吩,从而形成空穴注入及传输容易的HOMO,形成低的驱动电压,并实现高效率、长寿命的有机发光器件。并且,可维持高的三重态能量,可通过形成发光层内部的激子,可实现高效率,容易适用磷光器件,通过调节取代位置或苯环,在低分子下也可维持高Tg,由此可防止薄膜的重结晶,增加驱动稳定性及寿命。
本发明的化合物具有高的发光效率、高的色纯度等效果,适用于有机电致发光器件、太阳能发电用有机光电器件等,由此可大大贡献于柔性显示器、照明设备等OLED产业。
附图说明
图1示出本发明一实例的有机电致发光器件的简图。
附图标记的说明
100:基板 200:空穴注入层
300:空穴传输层 400:发光层
500:电子传输层 600:电子注入层
1000:阳极 2000:阴极
具体实施方式
以下,参照附图,详细说明本发明的实例及实施例,使得本发明所属技术领域的普通技术人员可容易实施。
但是,本发明能够以多种不同的形态实现,且不局限于在此说明的实例及实施例。并且,在图中,为了明确说明本发明,省略了与说明无关的部分,在说明书全文中,对于类似的部分,标注了类似的附图标记。
在本发明说明书全文中,当一个部件位于另一部件“上”时,不仅包括一个部件与另一部件相接触的情况,还包括在两个部件之间存在其他部件的情况。
在本发明说明书全文中,当一个部分“包括”一个结构要素时,除非有特别相反的记载,则意味着还可包括其他结构要素,而不是排除其他结构要素。在本发明说明书全文中使用的术语“约”、“实质上”等在所提及的含义上提示固有的制备及物质容差时以其数值或接近于其数值的含义使用,以防止昧良心的侵权人不当地利用为了帮助理解本发明而提及准确或绝对的数值的公开内容。在本发明说明书全文中使用的术语“~(的)步骤”或“~的步骤”不意味着“用于~的步骤”。
在本发明说明书全文中,马库什(Markush)形式的表现中所含的“这些的组合”这一术语意味着选自由马库什形式的表现中所记载的多个结构要素组成的组中的一种以上的混合或组合,意味着包括选自由上述多个结构要素组成的组中的一种以上。
在本发明说明书全文中,“A和/或B”这一记载意味着“A或B,或者A及B”。
在本发明说明书全文中,术语“芳基”意味着包含C5-30的芳香族烃环基,例如,苄基、苯基、萘基、联苯基、三联苯基、芴基、菲基、三苯基烯基、苯基烯基、屈基、荧烷噻吩甲基、苯并芴基、苯并三苯基烯基、苯并屈基、蒽基、均二苯乙烯基、芘基等的芳香族环,“杂芳基”作为包含至少一个杂元素的芳香族环,例如,意味着包含吡咯啉基、吡嗪基、吡啶基、吲哚基、异吲哚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、苯并苯硫基、二苯并苯硫基、喹啉基、异喹啉基、喹喔啉基、咔唑基、菲唳基、吖啶基、菲咯啉基、噻吩基及由吡啶环、吡嗪环、嘧啶环、哒嗪环、三嗪环、吲哚环、喹啉环、吖啶环、吡咯烷环、二烷环、哌啶环、吗啉环、哌嗪环、咔唑环、呋喃环、噻吩环、/>唑环、/>二唑环、苯并/>唑环、噻唑环、噻重氮环、苯并噻唑环、三唑环、咪唑环、苯并咪唑环、吡喃环、二苯并呋喃环形成的芳香族杂环基。
在本发明说明书全文中,术语“烷基”可以包含直链型或支链型的饱和或不饱和的C1-C6烷基,例如可包含甲基、乙基、丙基、丁基、戊基、己基或这些可能的所有同分异构体,但有可能不局限于此。
本发明说明书全文中,在术语“取代或未取代的”中,“取代”意味着可由选自由重氢、卤素、氨基、氰基、硝基或C1~C20的烷基、C2~C20的烯基、C1~C20的烷氧基、C3~C20的环烷基、C3~C20的杂环烷基、C6~C30的芳基及C5~C30的杂芳基组成的组中的一个以上的基取代。
本发明的第一实施方式,提供由以下化学式1表示的化合物:
化学式1
在化学式1中,
Ar1为
Ar2至Ar4分别独立地表示苯基、联苯基或萘基,
L1及L2分别独立地表示直链,或者取代或未取代的C5-C30亚芳基,
在上述Ar1中,*意味着连接部位。
上述Ar1为二苯基芴、螺双芴、三亚苯、二苯并呋喃或二苯并噻吩中的一个,从而形成空穴注入及传输容易的HOMO,形成低的驱动电压,并可实现高效率、长寿命的有机发光器件。
在本发明的一实例中,上述化学式1的化合物可包含由以下化学式2-1、化学式2-2或化学式3表示的化合物:
化学式2-1
化学式2-2
化学式3
在上述多个化学式中,
Ar2至Ar4、L1及L2如化学式1所定义。
在本发明的一实例中,上述化学式1的化合物可包含由以下化学式4表示的化合物:
化学式4
在上述化学式中,
Ar2至Ar4如化学式1所定义,
L1及L2两者均为直链或者两者均为亚苯基,
X为S或O。
在本发明的一实例中,当上述化学式4中,L1及L2两者为可取代的C5-C30亚芳香基时,例如为亚苯基时,移动性(mobility)变慢,效率会减少,驱动电压会变高。
在本发明的一实例中,L1及L2分别独立地可以是直链或亚苯基。
在本发明的一实例中,L1及L2均可以直链或亚苯基。例如,在上述化学式1至4中,L1及L2均可以直链,这种情况下,化合物的移动性好,效果会更加增加,驱动电压会更加降低。
在本发明的一实例中,上述化合物可具有约550至约810的分子量,例如,可以是约550至约750、约550至约700、约550至约650、约600至约810、约650至约810、约700至约810或约600至约750。当分子量小于550时,难以制备化合物,当分子量大于810时,存在沉积时沉积温度增加的问题。
在本发明的一实例中,上述化学式1的化合物可包含以下化合物,但有可能不局限于此:
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例如,上述化学式1的化合物可包含以下化合物。以下化合物的移动性好,由此效率会更增加,驱动电压会更加提高:
本发明的第二实施方式,提供包含由上述化学式1表示的化合物的有机发光器件。上述有机发光器件可在第一电极及第二电极之间包括包含本发明的化合物的1层以上的有机物层。
在本发明的一实例中,上述有机物层可以是空穴注入层、空穴传输层及发光补助层中的1层以上,但有可能不局限于此,此时,本发明的化合物可单独使用或者与公知的有机发光化合物一起使用。
在本发明的一实例中,上述有机发光器件可包括含有空穴传输物质的有机物层及含有由上述化学式1表示的化合物的有机物层,但有可能不局限于此。
在本发明的一实例中,含有由上述化学式1表示的化合物的有机物层可以是发光补助层。
上述有机发光器件在阳极(anode)与阴极(cathode)之间可包括1个以上的空穴注入层(HIL)、空穴传输层(HTL)、发光层(EML)、电子传输层(ETL)、电子注入层(EIL)等有机物层。
例如,上述有机发光器件可根据图1中所记载的结构来制备而成。有机发光器件至上而下依次层叠阳极(空穴注入电极1000)/空穴注入层200/空穴传输层300/发光层400/电子传输层500/电子注入层600/阴极(电子注入电极2000)。
在图1中,上述基板100可使用用于有机发光器件中使用的基板,尤其,可以为机械强度、热稳定性、透明性、表面平滑性、处理容易性及防水性优秀的玻璃基板或者可弯曲的塑料基板。
空穴注入电极1000用作用于注入有机发光器件的空穴的阳极。为了可注入空穴,利用具有低的功函数的物质,可由氧化铟锡(ITO)、氧化铟锌(IZO)、石墨烯(graphene)之类的透明材质形成。
可通过真空沉积法、旋涂法、浇铸法、LB(Langmuir-Blodgett)法之类的方法,将空穴注入层物质沉积在上述阳极电极上部,由此可形成空穴注入层200。在通过上述真空沉积法来形成空穴注入层的情况下,其沉积条件根据用作空穴注入层200的材料的化合物、所需的空穴注入层的结构及热特性等而不同,但通常可在50-500℃的沉积温度、10-8至10-3托的真空度、0.01至/sec的沉积速度、/>至5μm的层厚度范围内适当地进行选择。
接着,通过真空沉积法、旋涂法、铸造法、LB法等来在上述空穴注入层200上部沉积空穴传输层物质,由此可形成空穴传输层300。在通过上述真空沉积法来形成空穴传输层的情况下,其沉积条件因使用的化合物而不同,但通常,优选地,在与空穴注入层的形成几乎相同的条件范围内进行选择。上述空穴传输层可以是一个以上,例如,可以是空穴传输层及发光补助层等两个层。上述空穴传输层及发光补助层中的一个可以包含本发明的化学式1的化合物。
之后,通过真空沉积法、旋涂法、铸造法、LB法等来在上述空穴传输层上部沉积发光层物质,由此可形成发光层400。在通过上述真空沉积法来形成发光层的情况下,其沉积条件因使用的化合物而不同,但通常,优选地,在与空穴注入层的形成几乎相同的条件范围内进行选择。并且,上述发光层材料可将公知的化合物用作主体或掺杂剂。
并且,在发光层一起使用磷光掺杂剂时,为了防止三重态激子或者空穴扩散到电子传输层的现象,通过真空沉积法或者旋涂法,还可层叠空穴阻挡材料(HBL)。此时可使用的空穴阻挡物质不受特别限制,但可选择任何用作空穴阻挡材料的公知的物质来利用。例如可列举二唑衍生物或三唑衍生物、邻菲咯啉衍生物或日本特开平11-329734(A1)中记载的的空穴阻挡材料等,可使用代表性的Balq(双(8-羟基-2-甲基喹啉)-铝双酚盐)、邻菲咯啉(phenanthrolines)类化合物(例:UDC公司BCP(浴铜灵))等。
在如上形成的发光层400上部形成有电子传输层500,此时,上述电子传输层可通过真空沉积法、旋涂法、铸造法等方法来形成。并且,上述电子传输层的沉积条件因使用的化合物而不同,但通常,优选地,在与空穴注入层的形成几乎相同的条件范围内进行选择。
之后,可在上述电子传输层500上部沉积电子注入层物质来形成电子注入层600,此时,上述电子传输层可通过真空沉积法、旋涂法、铸造法等的方法来形成常规的电子注入层物质。
上述器件的空穴注入层200、空穴传输层300、发光层400、电子传输层500可使用本发明的化合物或如下的物质,或者,可一同使用本发明的化合物和公知的物质。
通过真空沉积法或溅射法等的方法来在电子注入层600上形成用于注入电子的阴极2000。作为阴极,可使用多种金属。具体例有铝、金、银等的物质。
本发明的有机发光器件不仅可以采用阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、阴极结构的有机发光器件,还可采用多种结构的有机发光器件的结构,根据需要,还可形成一层或两层的中间层。
如上所述,根据本发明形成的各个有机物层的厚度可根据所需的程度来进行调节,优选地,具体为10至1000nm,更具体为20至150nm。
并且,在本发明中,包含由上述化学式1表示的化合物的有机物层可将有机物层的厚度调节为分子单位,因而具有表面均匀且形态稳定性突出的优点。
针对本实施方式的有机发光化合物,均可适用对于本发明的第一实施方式记载的内容,但有可能不局限于此。
以下,通过本发明的实施例进行更具体的说明,本发明的范围不局限于本实施例。
实施例
制备例1:中间体I-1合成
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在氩或氮气氛下,在二苯胺8.46g(50mM)、3,5-二溴-1,1'-联苯21.84g(70mM)、Pd2(dba)3 1.6g(1.7mM)、50%P(t-Bu)3 2ml(4mM)、NaOtBu 14.7g(152mM)中加入甲苯300ml,回流7小时,加热。反应结束后,立即过滤之后,用二氯甲烷提取,加入MgSO4,过滤。去除过滤的有机层的溶剂之后,利用柱色谱进行纯化,由此获得中间体I-1(5-溴-N,N-二苯基-[1,1'-联苯基]-3-胺)16.41g。(收率:82%)
m/z:399.06(100.0%)、401.06(97.1%)、402.06(25.4%)、400.07(16.3%)、400.07(9.5%)、403.07(1.8%)、401.07(1.6%)、403.07(1.5%)、401.07(1.4%)
制备例2:中间体I-2合成
使用N-苯基-[1,1'-联苯基]-4-胺12.27g来代替二苯胺,除此之外,进行与制备例1相同的反应,由此获得中间体I-2(N-([1,1'-联苯基]-4-基)-5-溴-N-苯基-[1,1'-联苯基]-3-胺)19.54g。(收率:82%)
m/z:475.09(100.0%)、477.09(97.1%)、478.09(30.4%)、476.10(17.4%)、476.10(16.1%)、477.10(4.5%)、479.10(3.6%)、477.10(1.3%)、479.10(1.2%)
制备例3:中间体I-3合成
使用二([1,1'-联苯基]-4-基)胺16.08g来代替二苯胺,除此之外,进行与制备例1相同的反应,获得中间体I-3(N,N-二([1,1'-联苯基]-4-基)-5-溴-[1,1'-联苯基]-3-胺)22.11g。(收率:80%)
m/z:551.12(100.0%)、553.12(97.1%)、554.13(38.2%)、552.13(22.9%)、552.13(16.0%)、555.13(6.8%)、553.13(5.3%)、553.13(2.5%)
制备例4:中间体I-4合成
在氩或氮气氛下,投入I-1 20.02g(50mM)、苯胺7.5g(80mM)、Pd2(dba)3 1.2g(1.3mM)、P(t-Bu)3 1.5ml(3mM)g、NaOtBu 11.05g(115mM)之后加入甲苯200ml,5小时回流,加热。反应结束后,立即过滤之后,用二氯甲烷提取,加入MgSO4,过滤。去除过滤的有机层的溶剂之后,利用柱色谱进行纯化,由此获得中间体I-4(N3,N3,N5-三苯基-[1,1'-联苯基]-3,5-二胺)16.92g。(收率:82%)
m/z:412.19(100.0%)、413.20(32.1%)、414.20(2.9%)、414.20(2.5%)
制备例5:中间体I-5合成
使用I-2 23.82g来代替I-1,除此之外,进行与制备例4相同的反应,由此获得中间体I-5(N3-([1,1'-联苯基]-4-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-di胺)20.28g。(收率:83%)
m/z:488.23(100.0%)、489.23(38.7%)、490.23(7.8%)
制备例6:中间体I-6合成
使用27.63g的I-3来代替I-1,除此之外,进行与制备例3相同的反应,由此获得中间体I-6(N3,N3-二([1,1'-联苯基]-4-基)-N5-苯基-[1,1'-联苯基]-3,5-二胺)22.87g。(收率:81%)
m/z:564.26(100.0%)、565.26(44.3%)、566.26(11.2%)
合成例1:化合物1的合成
在氩或氮气氛下,投入2-溴-9,9-二苯基-9H-芴27.82g(70mM)、I-4 20.63g(50mM),进行与制备例1相同的反应,由此获得化合物1(N3-(9,9-二苯基-9H-芴-2-基)-N3,N5,N5-三苯基-[1,1'-联苯基]-3,5-二胺)29.16g。(收率:80%)
m/z:728.32(100.0%)、729.32(59.8%)、730.33(17.2%)、731.33(2.4%)
合成例2:化合物2合成
使用I-5 24.43g来代替I-4,除此之外,进行与合成例1相同的反应,由此获得化合物2(N3-([1,1'-联苯基]-4-基)-N5-(9,9-二苯基-9H-芴-2-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)32.2g。(收率:80%)
m/z:804.35(100.0%)、805.35(66.3%)、806.36(21.2%)、807.36(3.6%)
合成例3:化合物3合成
使用3-溴-9,9-二苯基-9H-芴27.82g来代替2-溴-9,9-二苯基-9H-芴,除此之外,进行与合成例1相同的反应,由此获得化合物3(N3-(9,9-二苯基-9H-芴-3-基)-N3,N5,N5-三苯基-[1,1'-联苯基]-3,5-二胺)29.52g。(收率:81%)
m/z:728.32(100.0%)、729.32(59.3%)、730.33(17.5%)、731.33(2.6%)
合成例4:化合物4合成
使用I-5 24.43g来代替I-4,除此之外,进行与合成例3相同的反应,由此获得化合物4(N3-([1,1'-联苯基]-4-基)-N5-(9,9-二苯基-9H-芴-3-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)33.41g。(收率:83%)
m/z:804.35(100.0%)、805.35(66.2%)、806.36(21.5%)、807.36(3.4%)
合成例5:化合物5合成
使用4-溴-9,9-二苯基-9H-芴27.82g来代替2-溴-9,9-二苯基-9H-芴,除此之外,进行与合成例1相同的反应,由此获得化合物5(N3-(9,9-二苯基-9H-芴-4-基)-N3,N5,N5-三苯基-[1,1'-联苯基]-3,5-二胺)29.89g。(收率:82%)
m/z:728.32(100.0%)、729.32(59.8%)、730.33(17.3%)、731.33(2.3%)
合成例6:化合物6合成
使用I-5 24.43g来代替I-4,除此之外,进行与合成例5相同的反应,由此获得化合物6(N3-([1,1'-联苯基]-4-基)-N5-(9,9-二苯基-9H-芴-4-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)32.61g。(收率:81%)
m/z:804.35(100.0%)、805.35(66.2%)、806.36(21.5%)、807.36(3.4%)
合成例7:化合物7合成
使用2-溴-9,9'-螺双[芴]27.67g来代替2-溴-9,9-二苯基-9H-芴,除此之外,进行与合成例1相同的反应,由此获得化合物7(N3-(9,9'-螺双[芴]-2-基)-N3,N5,N5-三苯基-[1,1'-联苯基]-3,5-二胺)29.81g。(收率:82%)
m/z:726.30(100.0%)、727.31(59.3%)、728.31(17.3%)、729.31(2.7%)
合成例8:化合物8合成
使用I-5 24.43g来代替I-4,除此之外,进行与合成例7相同的反应,由此获得化合物8(N3-(9,9'-螺双[芴]-2-基)-N5-([1,1'-联苯基]-4-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)32.52g。(收率:81%)
m/z:802.33(100.0%)、803.34(66.1%)、804.34(21.6%)、805.34(3.4%)
合成例9:化合物9合成
使用3-溴-9,9'-螺双[芴]27.67g来代替2-溴-9,9-二苯基-9H-芴,除此之外,进行与合成例1相同的反应,由此获得化合物9(N3-(9,9'-螺双[芴]-3-基)-N3,N5,N5-三苯基-[1,1'-联苯基]-3,5-二胺)30.17g。(收率:83%)
m/z:726.30(100.0%)、727.31(59.2%)、728.31(17.5%)、729.31(2.7%)
合成例10:化合物10合成
使用I-5 24.43g来代替I-4,除此之外,进行与合成例9相同的反应,由此获得化合物10(N3-(9,9'-螺双[芴]-3-基)-N5-([1,1'-联苯基]-4-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)32.93g。(收率:82%)
m/z:802.33(100.0%)、803.34(65.7%)、804.34(21.5%)、805.34(3.8%)
合成例11:化合物11合成
使用4-溴-9,9'-螺双[芴]27.67g来代替2-溴-9,9-二苯基-9H-芴,除此之外,进行与合成例1相同的反应,由此获得化合物11(N3-(9,9'-螺双[芴]-4-基)-N3,N5,N5-三苯基-[1,1'-联苯基]-3,5-二胺)29.08g。(收率:80%)
m/z:726.30(100.0%)、727.31(59.3%)、728.31(17.5%)、729.31(2.6%)
合成例12:化合物12合成
使用I-5 24.43g来代替I-4,除此之外,进行与合成例11相同的反应,由此获得化合物12(N3-(9,9'-螺双[芴]-4-基)-N5-([1,1'-联苯基]-4-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)32.91g。(收率:82%)
m/z:802.33(100.0%)、803.34(66.4%)、804.34(21.7%)、805.34(3.8%)
合成例13:化合物13合成
使用2-溴二苯并[b,d]呋喃17.3g来代替2-溴-9,9-二苯基-9H-芴,除此之外,进行与合成例1相同的反应,由此获得化合物13(N3-([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]呋喃-2-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)25.86g。(收率:79%)
m/z:654.27(100.0%)、655.27(51.7%)、656.27(13.3%)、657.28(1.5%)
合成例14:化合物14合成
使用I-6 28.24g来代替I-5,除此之外,进行与合成例13相同的反应,由此获得化合物14(N3,N3-二([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]呋喃-2-基)-N5-苯基-[1,1'-联苯基]-3,5-二胺)29.61g。(收率:81%)
m/z:730.30(100.0%)、731.30(58.6%)、732.31(16.6%)、733.31(2.2%)
合成例15:化合物15合成
使用3-溴二苯并[b,d]呋喃17.3g来代替2-溴二苯并[b,d]呋喃,除此之外,进行与合成例13相同的反应,由此获得化合物15(N3-([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]呋喃-3-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)26.19g。(收率:80%)
m/z:654.27(100.0%)、655.27(51.6%)、656.27(13.4%)、657.28(1.5%)
合成例16:化合物16合成
使用I-6 28.24g来代替I-5,除此之外,进行与合成例15相同的反应,由此获得化合物16(N3,N3-二([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]呋喃-3-基)-N5-苯基-[1,1'-联苯基]-3,5-二胺)29.24g。(收率:80%)
m/z:730.30(100.0%)、731.30(58.1%)、732.31(16.8%)、733.31(2.5%)
合成例17:化合物17合成
使用4-溴二苯并[b,d]呋喃17.3g来代替2-溴二苯并[b,d]呋喃,除此之外,进行与合成例13相同的反应,由此获得化合物17(N3-([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]呋喃-4-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)26.85g。(收率:82%)
m/z:654.27(100.0%)、655.27(51.5%)、656.27(13.5%)、657.28(1.5%)
合成例18:化合物18合成
使用I-6 28.24g来代替I-5,除此之外,进行与合成例17相同的反应,由此获得化合物18(N3,N3-二([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]呋喃-4-基)-N5-苯基-[1,1'-联苯基]-3,5-二胺)29.61g。(收率:81%)
m/z:730.30(100.0%)、731.30(58.2%)、732.31(16.8%)、733.31(2.4%)
合成例19:化合物19合成
使用2-溴二苯并[b,d]噻吩18.42g来代替2-溴二苯并[b,d]呋喃,除此之外,进行与合成例13相同的反应,由此获得化合物19(N3-([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]噻吩-2-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)27.17g。(收率:81%)
m/z:670.24(100.0%)、671.25(51.5%)、672.25(13.4%)、672.24(4.6%)、673.24(2.1%)、673.25(1.6%)
合成例20:化合物20合成
使用I-6 28.24g来代替I-5,除此之外,进行与合成例19相同的反应,由此获得化合物20(N3,N3-二([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]噻吩-2-基)-N5-苯基-[1,1'-联苯基]-3,5-二胺)29.89g。(收率:80%)
m/z:746.28(100.0%)、747.28(58.5%)、748.28(16.8%)、748.27(4.3%)、749.27(2.7%)、749.29(2.2%)
合成例21:化合物21合成
使用3-溴二苯并[b,d]噻吩18.42g来代替2-溴二苯并[b,d]呋喃,除此之外,进行与合成例13相同的反应,由此获得化合物21(N3-([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]噻吩-3-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)27.84g。(收率:83%)
m/z:670.24(100.0%)、671.25(51.5%)、672.25(13.5%)、672.24(4.6%)、673.24(2.2%)、673.25(1.5%)
合成例22:化合物22合成
使用I-6 28.24g来代替I-5,除此之外,进行与合成例21相同的反应,由此获得化合物22(N3,N3-二([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]噻吩-3-基)-N5-苯基-[1,1'-联苯基]-3,5-二胺)30.63g。(收率:82%)
m/z:746.28(100.0%)、747.28(58.8%)、748.28(16.9%)、748.27(4.1%)、749.27(2.5%)、749.29(2.2%)
合成例23:化合物23合成
使用4-溴二苯并[b,d]噻吩18.42g来代替2-溴二苯并[b,d]呋喃,除此之外,进行与合成例13相同的反应,由此获得化合物23(N3-([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]噻吩-4-基)-N3,N5-二苯基-[1,1'-联苯基]-3,5-二胺)26.51g。(收率:79%)
m/z:670.24(100.0%)、671.25(51.7%)、672.25(13.4%)、672.24(4.2%)、673.24(2.5%)、673.25(1.5%)
合成例24:化合物24合成
使用I-6 28.24g来代替I-5,除此之外,进行与合成例23相同的反应,由此获得化合物24(N3,N3-二([1,1'-联苯基]-4-基)-N5-(二苯并[b,d]噻吩-4-基)-N5-苯基-[1,1'-联苯基]-3,5-二胺)29.88g。(收率:80%)
m/z:746.28(100.0%)、747.28(58.1%)、748.28(16.4%)、748.27(4.7%)、749.27(2.9%)、749.29(2.4%)
合成例25:化合物25合成
使用2-溴三亚苯21.5g来代替2-溴-9,9-二苯基-9H-芴,除此之外,进行与合成例2相同的反应,由此获得化合物25(N3-([1,1'-联苯基]-4-基)-N3,N5-二苯基-N5-(三亚苯-2-基)-[1,1'-联苯基]-3,5-二胺)28.6g。(收率:80%)
m/z:714.30(100.0%)、715.31(58.1%)、716.31(16.8%)、717.31(2.5%)
合成例26:化合物26合成
使用I-6 24.43g来代替I-5,除此之外,进行与合成例25相同的反应,由此获得化合物26(N3,N3-二([1,1'-联苯基]-4-基)-N5-苯基-N5-(三亚苯-2-基)-[1,1'-联苯基]-3,5-二胺)30.85g。(收率:78%)
m/z:790.33(100.0%)、791.34(65.1%)、792.34(20.9%)、793.34(3.1%)
制备例7:有机发光器件的制备
对通过蒸馏水超声波以的厚度将氧化铟锡(ITO)涂敷成薄膜的玻璃基板进行洗涤。若蒸馏水洗涤结束,则利用异丙醇、丙酮、甲醇等的溶剂来进行超声波洗涤,并进行干燥之后,移送至等离子清洗机,然后利用氧等离子来将上述基板清洗5分钟之后,在氧化铟锡基板上部利用热真空沉积器(thermal evaporator),作为空穴注入层将/>的HI01进行制膜,将/>的HATCN进行制膜,作为空穴传输层将/>的化合物1进行制膜。然后,作为上述发光层掺杂7%的GH:Ir(ppy)3,以/>进行制膜。接着,作为电子传输层将/> 的ET:Liq(1:1)进行制膜之后,将/>的LiF、/>的铝(Al)进行制膜,并将该器件密封(Encapsulation)于手套箱中,从而制备了有机发光器件(实施例1)。
通过如上所述的方式使用化合物2至化合物26来代替化合物1,从而制备了有机发光器件(实施例2至实施例26)。
比较例
使用以下Ref.1至Ref.7(比较例1至7)来代替化合物1,除此之外,与上述制备例7相同地制备了有机发光器件。
实验例1:有机发光器件的性能评价
利用吉时利2400源测量单元(Kiethley 2400source measurement unit)施加电压来注入电子及空穴,利用柯尼卡美能达(Konica Minolta)分光辐射计(CS-2000)来测定发光时的亮度,由此在大气压条件下,测定对于施加电压的电流密度及亮度,从而评价了实施例及比较例的有机发光器件的性能,并将其结果示于表1中。表1
/>
如上述表1所示,当比较使用两个氮原子之间取代苯基的亚苯基的本发明的化合物、使用取代1个苯基的亚联苯基的比较例1、比较例2、使用未取代的亚联苯基的比较例5至比较例7、取代一个二苯并呋喃或二苯并噻吩的实施例13至实施例24、取代2个二苯并呋喃或二苯并噻吩的比较例3、比较例4时,可确认到呈现高效率、长寿命的特性,电压也降低。由此可知,本发明的化合物可降低有机发光器件的驱动电压,并可提高效率,可改善寿命。尤其是,当一侧导入二苯并呋喃或二苯并噻吩的芳基胺之间追加亚苯基的情况下,具体的,使用了相当于本发明的化学式1的结构中,L1及L2均为亚苯基的情况的Ref.1及Ref.2的比较例1及2,移动性(mobility)变得更慢,由此可确认效率减少,驱动电压增加。
上述本发明的说明是用于例示性的,本发明所属技术领域的普通技术人员可以理解在不变更本发明的技术思想或必要特征的情况下,能够以其他具体方式容易变形。因此,应理解以上描述的多个实施例在所有方面是例示性的,而不是限定性的。例如,以单一型说明的各个结构要素可分散地实施,同样,说明为分散的多个结构要素也能够以结合的方式实施。
本发明的范围由所附的专利发明要求保护范围表示,而不是上述详细说明,专利发明要求保护范围的含义及范围以及由其等同概念导出的所有变更或变形的方式应当被解释为包括在本发明的范围中。
Claims (9)
1.一种化合物,其特征在于,由以下化学式1表示:
化学式1
在上述化学式1中,
Ar1为
Ar2至Ar4分别独立地表示苯基、或联苯基,但当Ar1为二苯并呋喃或二苯并噻吩时,Ar2至Ar4中的至少一个为联苯基,
L1及L2均为直链,
在上述Ar1中,*意味着连接部位。
2.根据权利要求1所述的化合物,其特征在于,上述化合物包含由以下化学式2-1、化学式2-2或化学式3表示的化合物:
化学式2-1
化学式2-2
化学式3
在上述化学式中,Ar2至Ar4、L1及L2如权利要求1所定义。
3.根据权利要求1所述的化合物,其特征在于,上述化合物包含由以下化学式4表示的化合物:
化学式4
在上述化学式中,
Ar2至Ar4如权利要求1所定义,
L1及L2两者均为直链,
X为S或O。
4.根据权利要求1至3中任一项所述的化合物,其特征在于,上述化合物具有550至810的分子量。
5.根据权利要求1所述的化合物,其特征在于,上述化合物包含以下化合物中的一种:
6.一种有机发光器件,其特征在于,在第一电极及第二电极之间包括包含一种以上权利要求1所示的化合物的1层以上的有机物层。
7.根据权利要求6所述的有机发光器件,其特征在于,上述有机物层为空穴注入层、空穴传输层及发光补助层中的1层以上。
8.根据权利要求6所述的有机发光器件,其特征在于,上述有机发光器件包括含有空穴传输物质的有机物层及由权利要求1所述的化学式1表示的化合物的有机物层。
9.根据权利要求8所述的有机发光器件,其特征在于,含有由上述化学式1表示的化合物的有机物层为发光补助层。
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CN115710187A (zh) * | 2021-03-03 | 2023-02-24 | 江苏三月科技股份有限公司 | 一种芳胺类有机化合物及包含该化合物的有机电致发光器件 |
CN113582855B (zh) * | 2021-07-30 | 2024-01-26 | 长春海谱润斯科技股份有限公司 | 一种二胺类有机化合物及其有机发光器件 |
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