CN110741002A - Novel heterocyclic compound and organic light emitting device comprising the same - Google Patents
Novel heterocyclic compound and organic light emitting device comprising the same Download PDFInfo
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- CN110741002A CN110741002A CN201880039613.2A CN201880039613A CN110741002A CN 110741002 A CN110741002 A CN 110741002A CN 201880039613 A CN201880039613 A CN 201880039613A CN 110741002 A CN110741002 A CN 110741002A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 6
- 239000010410 layer Substances 0.000 claims description 126
- 239000000126 substance Substances 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 66
- 239000012044 organic layer Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 4
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- 125000005842 heteroatom Chemical group 0.000 claims description 4
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- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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- 230000015572 biosynthetic process Effects 0.000 description 61
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- 230000005525 hole transport Effects 0.000 description 12
- UOQCHAHZQHMEBE-UHFFFAOYSA-N 4-(4-chlorophenyl)-6-phenyl-2-(3-phenylphenyl)pyrimidine Chemical compound Clc1ccc(cc1)-c1cc(nc(n1)-c1cccc(c1)-c1ccccc1)-c1ccccc1 UOQCHAHZQHMEBE-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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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 3
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 3
- PIWNKSHCLTZKSZ-UHFFFAOYSA-N 8-bromoquinoline Chemical compound C1=CN=C2C(Br)=CC=CC2=C1 PIWNKSHCLTZKSZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
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- 239000010405 anode material Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
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- 125000004185 ester group Chemical group 0.000 description 3
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000010409 thin film Substances 0.000 description 3
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- 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
- 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
- WTAPZWXVSZMMDG-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WTAPZWXVSZMMDG-UHFFFAOYSA-N 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 2
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- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 125000005241 heteroarylamino group Chemical group 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 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 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
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
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- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- AHYDHCHTAAUWQZ-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-naphthalen-1-yl-2H-pyrimidine Chemical compound Clc1cccc(c1)N1CN=C(C=C1)c1cccc2ccccc12 AHYDHCHTAAUWQZ-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
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- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- 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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- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
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- 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
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Abstract
The invention provides a novel heterocyclic compound and an organic light-emitting element using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2017-0135362, 18/2017, and korean patent application No. 10-2018-0088201, 27/2018, including the entire disclosure of the korean patent application as part of the present specification.
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light-emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.
Development of new materials for organic materials used in the organic light-emitting devices described above is continuously demanded.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1 described above,
Y1and Y2Each independently is hydrogen; substituted or unsubstituted C1-40An alkyl group; substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing O, N, Si and or more of S2-60(ii) a heteroaryl group, wherein,
ar is substituted or unsubstituted C containing O, N, Si and or more of S2-60A heteroaryl group; phenyl substituted with cyano; triphenylsilane; or diphosphine oxides
Each L is independently a direct bond; substituted or unsubstituted C6-60Arylene, or C containing a heteroatom selected from N, O, S and any or more of Si2-60A heteroarylene group, a heteroaryl group,
R1to R3Each independently is halogen; a hydroxyl group; a cyano group; a nitrile group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substituted or unsubstituted C1-60A thioalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstitutedC1-60A haloalkoxy group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C1-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing O, N, Si and or more of S2-60(ii) a heteroaryl group, wherein,
m is a number of 0 to 4,
n is a number of from 0 to 2,
o is a number of from 0 to 3,
z is 1 to 4, but o + z is 4 or less.
The present invention also provides types of organic light-emitting elements, each of which includes a th electrode, a second electrode provided so as to face the th electrode, and an organic layer including or more layers between the th electrode and the second electrode, wherein or more layers of the organic layer include the compound represented by chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting element in which improvement of efficiency, lower driving voltage, and/or improvement of life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission.
Drawings
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole adjusting layer 7, a light-emitting layer 8, an electron adjusting layer 9, an electron transport layer 10, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the context of the present specification,
and
refers to a bond to another substituent.
As used herein, the phrase "substituted or unsubstituted" refers to a compound substituted with atoms by a substituent selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group(s) ((R))
Alkyl thio xy); arylthio radicals (A), (B), (C
Aryl thio xy); alkylsulfonyl (Alkyl sulfo xy); arylsulfonyl (
Aryl sulfoxy), silyl, boryl, alkyl, cycloalkyl, alkenyl, Aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino, or or more substituents among heterocyclic groups containing N, O and S atoms, or substituted or unsubstituted with or linked to 2 or more substituents among the above-exemplified substituents.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or a branched chain, the number of carbon atoms is not particularly limited, but is preferably 1 to 40, according to the embodiment, the number of carbon atoms of the alkyl group is 1 to 20, according to the embodiment, the number of carbon atoms of the alkyl group is 1 to 10, according to the embodiment, the number of carbon atoms of the alkyl group is 1 to 6, and specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a.
In the present specification, the above alkenyl group may be a straight chain or a branched chain, the number of carbon atoms is not particularly limited, but is preferably 2 to 40, according to the embodiment, the above alkenyl group has 2 to 20, according to the embodiment, the above alkenyl group has 2 to 10, according to the embodiment, the above alkenyl group has 2 to 6 carbon atoms, and specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (diphenylen-1-yl) ethen-1-yl, stilbenyl, styryl, and the like, but is not limited thereto.
In the present specification, a cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to the embodiment, the cycloalkyl group has 3 to 30 carbon atoms, according to the embodiment, the cycloalkyl group has 3 to 20 carbon atoms, according to the embodiment, the cycloalkyl group has 3 to 6 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl groupAccording to the embodiment, the above aryl group has 6 to 30 carbon atoms, according to the embodiment, the above aryl group has 6 to 20 carbon atoms, and with respect to the above aryl group, as the monocyclic aryl group, phenyl, biphenyl, terphenyl, and the like are possible, but not limited theretoAnd a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like. But is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing at least 1 of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
in the above chemical formula 1, Y1And Y2May each independently be methyl or phenyl.
In the above chemical formula 1, m, n and o may be 0.
In the above chemical formula 1, z may be 1.
The above chemical formula 1 may be any selected from the group consisting of the compounds represented by the following chemical formulas 1-1 to 1-8.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1 to 4]
[ chemical formulas 1 to 5]
[ chemical formulas 1 to 6]
[ chemical formulas 1 to 7]
[ chemical formulas 1 to 8]
In the above chemical formulas 1-1 to 1-8,
each L is independently a direct bond; substituted or unsubstituted C6-60Arylene, or C containing a heteroatom selected from N, O, S and any or more of Si2-60A heteroarylene group, a heteroaryl group,
ar may be substituted or unsubstituted C comprising O, N, Si and or more of S2-60A heteroaryl group; phenyl substituted with cyano; triphenylsilane; or a diphosphine oxide.
Preferably, each Ar may be independently any selected from the following groups.
X1To X4Each independently is N or CR', but at least or more of them are N,
r' is hydrogen, or substituted or unsubstituted C1-60The alkyl group of (a) is,
X5is N, S or O, and the content of the active carbon,
R4and R5Each independently is halogen; a hydroxyl group; a cyano group; a nitrile group; a nitro group; an amine group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substituted or unsubstituted C1-60A thioalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C1-60A haloalkoxy group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C1-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing O, N, Si and or more of S2-60A heteroaryl group.
Preferably, each L may be independently any selected from the following structures.
Preferably, the compound represented by the above chemical formula 1 may be any selected from the following structures.
The compound represented by the above chemical formula 1 can be produced by the following production methods represented by the following reaction formulae 1 and 2 as examples, and the production method can be embodied by steps in the production examples described later.
[ reaction formula 1]
[ reaction formula 2]
In the above reaction formulas 1 and 2, the descriptions of L and Ar are the same as those defined above.
examples of the present invention provide kinds of organic light-emitting elements each including a th electrode, a second electrode provided so as to face the th electrode, and an organic layer including layers or more between the th electrode and the second electrode, wherein layers or more of the organic layers include the compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole adjusting layer, a light-emitting layer, an electron adjusting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include an electron transport layer, an electron modulation layer, an electron injection layer, a hole blocking layer, or a light emitting layer, and the electron transport layer, the electron modulation layer, the electron injection layer, the hole blocking layer, or the light emitting layer may include the compound represented by chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron transport layer or an electron injection layer including the compound represented by the chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron transport and electron injection includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting element according to the present invention may be an organic light emitting element of a structure (normal type) in which an anode, or more organic layers, and a cathode are sequentially stacked on a substrate, and further, an organic light emitting element according to the present invention may be an organic light emitting element of a reverse structure (inverted type) in which a cathode, or more organic layers, and an anode are sequentially stacked on a substrate, and for example, a structure example of an organic light emitting element according to a embodiment of the present invention is shown in fig. 1 and 2.
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.
Fig. 2 shows an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole adjusting layer 7, a light-emitting layer 8, an electron adjusting layer 9, an electron transport layer 10, and a cathode 4 in the structure described above, the compound represented by the above chemical formula 1 may be contained in layers or more among the above hole injection layer, hole transport layer, hole adjusting layer, light-emitting layer, electron adjusting layer, and electron transport layer.
In addition, the organic light emitting device may further include a hole blocking layer, an electron injection layer, or the like, and the compound represented by the chemical formula 1 may be included in the hole blocking layer or the electron injection layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that or more layers among the organic layers include the compound represented by chemical formula 1, and further, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting element according to the present invention can be manufactured by stacking the th electrode, the organic layer, and the second electrode in this order on the substrate, and in this case, it can be manufactured by forming an anode by evaporating metal or a metal oxide having conductivity or an alloy thereof on the substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation), forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then evaporating a substance that can be used as a cathode on the organic layer.
In addition, when the compound represented by the above chemical formula 1 is used to manufacture an organic light emitting device, the organic layer may be formed not only by a vacuum deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting element can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In examples, the th electrode is an anode and the second electrode is a cathode, or the th electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); such as ZnO: al or SNO2: a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection material is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection material: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimerized styryl (dimerizidetstyryl) compoundsAn agent; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,Diindenoperene (Periflanthene) and the like, as the styrylamine compound, a compound in which at least arylethenyl groups are substituted with a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino groups, specifically, styrylamine, styryldiamine, styryltrriamine, styryltretraamine and the like are mentioned, but not limited thereto.
The electron transporting material is a layer which receives electrons from the electron injecting layer and transports the electrons to the light emitting layer as an electron transporting materialThe substance is a substance capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3Electron transport layers may be used with any desired cathode material as used in the art.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: the organic light-emitting device has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injection layer, and has excellent thin-film formation ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting element according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.
In the following, preferred embodiments are set forth to aid in understanding the invention. However, the following examples are merely illustrative of the present invention, and the present invention is not limited thereto.
Production example 1-1
1) Synthesis of A1-1
DMF (400ml) was added to 9, 9-dimethyl-9H-fluoren-2-ol (150.7g, 716.7mmol) and dissolved, and NBS (177.98g, 716.7mmol) was slowly added dropwise at 0 ℃ and then stirred at room temperature for 3 hours. After extraction with water and chloroform (chloroform) at room temperature, the white solid was recrystallized from hexane to produce the above-mentioned compound A1-1(165g, yield: 80%).
MS[M+H]+＝290.17
2) Synthesis of A1-2
A1-1(20g, 69.16mmol), bis (pinacolato) diboron (19.3g, 76.0mmol) and potassium acetate (13.3g, 138.3mmol) were charged to 200mL of 1, 4-bis
To the mixture was added palladium dibenzylideneacetone (795mg, 0.02 mol%) and tricyclohexylphosphine (775mg, 0.04 mol%) under reflux with stirring, and the mixture was stirred under reflux for 12 hours. At the end of the reaction, the mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure, chloroform was added to the residue to dissolve the residue, the solution was washed with water to separate an organic layer, and anhydrous magnesium sulfate (Magnesiu) was addedm sulfate) was dried. This was distilled under reduced pressure, and stirred with ethyl acetate and ethanol to give A1-2(19.76g, yield 86%).
MS[M+H]+＝337.24
3) Synthesis of A1-3
A1-2(20g, 58.48mmol) was put into 100ml of a 2M aqueous NaOH solution, and after the temperature was stabilized at 0 ℃, hydrogen peroxide (3eq) was slowly added dropwise. After completion of the reaction, 60ml of hydrogen chloride was added dropwise thereto at 0 ℃ for neutralization, and after cooling to room temperature, filtration was carried out, followed by washing with water and hexane, thereby producing the above-mentioned compound A1-3(10.76g, yield: 80%).
MS[M+H]+＝227.28
Production examples 1 and 2
1) Synthesis of B1-1
B1-1 was produced by the same method except that 9, 9-diphenyl-9H-fluoren-2-ol was used instead of 9, 9-dimethyl-9H-fluoren-2-ol in the synthesis of a 1-1.
MS[M+H]+＝414.31
2) Synthesis of B1-2
B1-2 was produced by the same method except that B1-1 was used in place of A1-1 in the synthesis of A1-2.
MS[M+H]+＝460.38
3) Synthesis of B1-3
B1-3 was produced by the same method except that B1-2 was used in place of A1-2 in the above-mentioned synthesis of A1-3.
MS[M+H]+＝351.42
Production example 2-1: synthesis of A2-1
A1-3(20g, 88.38mmol), 1-bromo-2, 3-difluorobenzene (17.91g, 92.80mmol) and potassium carbonate (36.64g, 265mmol) were added to dimethylformamide (300ml), and the mixture was stirred under heating for 3 hours. After the reaction was completed by cooling to room temperature, water was added, the mixture was filtered, the filtrate was dissolved in chloroform and extracted, and column chromatography was performed using ethyl acetate and hexane to obtain a2-1(26.8g, yield 80%).
MS[M+H]+＝380.25
Production example 2-2: synthesis of A2-2
In the synthesis of A2-1, A2-2 was produced by the same method.
MS[M+H]+＝380.25
Production examples 2 to 3: synthesis of A2-3
A2-3 was produced by the same method except that 4-bromo-1, 2-difluorobenzene was used instead of 1-bromo-2, 3-difluorobenzene in the synthesis of a 2-1.
MS[M+H]+＝380.25
Production examples 2 to 4: synthesis of A2-4
In the synthesis of A2-3, A2-4 was produced by the same method.
MS[M+H]+＝380.25
Production examples 2 to 5: synthesis of B2-1
B2-1 was synthesized in the same manner as described above except that in the synthesis of A2-1, B1-3 was used in place of A1-3 and B2-1 was used in place of A2-1.
MS[M+H]+＝504.40
Production examples 2 to 6: synthesis of B2-2
In the synthesis of B2-1, B2-2 was produced by the same method.
MS[M+H]+＝504.40
Production examples 2 to 7: synthesis of B2-3
B2-3 was produced by the same method except that 4-bromo-1, 2-difluorobenzene was used instead of 1-bromo-2, 3-difluorobenzene in the synthesis of B2-1.
MS[M+H]+＝504.40
Production examples 2 to 8: synthesis of B2-4
In the synthesis of B2-3, B2-4 was produced by the same method.
MS[M+H]+＝504.40
Production example 3-1: synthesis of A3-1
Mixing the compound A2-1(20g, 52.73mmol), bis (pinacolato) diboron (14.73g, 58.0mmol) and potassium acetate (10.1g, 105.4mmol) were charged to 200mL of 1, 4-bis
To the mixture was added palladium dibenzylideneacetone (606mg, 0.02 mol%) and tricyclohexylphosphine (595mg, 0.04 mol%) under reflux with stirring, and the mixture was stirred under reflux for 12 hours. At the end of the reaction, the mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure, and chloroform was added to and dissolved in the residue, and the residue was washed with water to separate an organic layer, and then dried over anhydrous Magnesium sulfate (Magnesium sulfate). This was distilled under reduced pressure and recrystallized from ethyl acetate to give A3-1(19.33g, yield 86%).
MS[M+H]+＝427.32
Production example 3-2: synthesis of A3-2
A3-2 was produced by the same method except that A2-2 was used in place of A2-1 in the synthesis of A3-1.
MS[M+H]+＝427.32
Production examples 3 to 3: synthesis of A3-3
A3-3 was produced by the same method except that A2-3 was used in place of A2-1 in the synthesis of A3-1.
MS[M+H]+＝427.32
Production examples 3 to 4: synthesis of A3-4
A3-4 was produced by the same method except that A2-4 was used in place of A2-1 in the synthesis of A3-1.
MS[M+H]+＝427.32
Production examples 3 to 5: synthesis of B3-1
B3-1 was produced by the same method except that B2-1 was used in place of A2-1 in the synthesis of A3-1.
MS[M+H]+＝551.46
Production examples 3 to 6: synthesis of B3-2
B3-2 was synthesized in the same manner as described above except that B2-2 was used in place of B2-1 in the synthesis of B3-1.
MS[M+H]+＝551.46
Production examples 3 to 7: synthesis of B3-3
B3-3 was produced by the same method except that B2-3 was used in place of B2-1 in the synthesis of B3-1.
MS[M+H]+＝551.46
Production examples 3 to 8: synthesis of B3-4
B3-4 was synthesized in the same manner as described above except that B2-4 was used in place of B2-1 in the synthesis of B3-1.
MS[M+H]+＝551.46
Production example 4-1: synthesis of Compound 1
After completely dissolving the above-mentioned compound A3-1(10.0g, 23.45mmol) and 2- ([1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine (9.92g, 23.69mmol) in tetrahydrofuran (300ml), a 2M aqueous potassium carbonate solution (150ml) was added, and tetrakis (triphenylphosphine) palladium (542mg, 2 mol%) was added, followed by stirring with heating for 10 hours. After the reaction was completed by cooling the temperature to room temperature, the aqueous potassium carbonate solution was removed to conduct layer separation. After removal of the solvent, the white solid was recrystallized from tetrahydrofuran and ethyl acetate to produce the above compound 1(12.48g, yield 78%).
MS[M+H]+＝683.82
Production example 4-2: synthesis of Compound 2
MS[M+H]+＝648.78
Production examples 4 to 3: synthesis of Compound 3
MS[M+H]+＝698.79
Production examples 4 to 4: synthesis of Compound 4
MS[M+H]+＝479.55
Production examples 4 to 5: synthesis of Compound 5
1) Synthesis of A4-1
A4-1 was synthesized in the same manner as in the synthesis of the above compound 1, except that A3-4 was used instead of A3-1 and 2-chloro-4- (4-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine.
MS[M+H]+＝567.06
2) Synthesis of Compound 5
A4-1(15g, 26.4mmol), 9H-carbazole (15g, 27.3mmol) and sodium tert-butoxide (4.56g, 59.2mol) were added to xylene, and after heating and stirring, reflux was performed, bis [ (tri-tert-butylphosphine) ] palladium (269mg, 2 mmol) was added. After the reaction was completed by cooling to room temperature, compound 5(15.08g, 82%) was produced by recrystallization from tetrahydrofuran and ethyl acetate.
MS[M+H]+＝697.81
Production examples 4 to 6: synthesis of Compound 6
MS[M+H]+＝693.82
Production examples 4 to 7: synthesis of Compound 7
MS[M+H]+＝730.87
Production examples 4 to 8: synthesis of Compound 8
1) Synthesis of B4-1
B4-1 was synthesized in the same manner as in the synthesis of compound 1 above, except that B3-2 was used instead of A3-1 and 2-chloro-4- (3-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -3-yl) -4- (4-chlorophenyl) -6-phenylpyrimidine.
MS[M+H]+＝767.30
2) Synthesis of Compound 8
MS[M+H]+＝833.96
Production examples 4 to 9: synthesis of Compound 9
MS[M+H]+＝732.86
Production examples 4 to 10: synthesis of Compound 10
MS[M+H]+＝552.65
Production examples 4 to 11: synthesis of Compound 11
Compound 11 was synthesized in the same manner as described above except that 3- (3-chlorophenyl) -6- (naphthalen-1-yl) pyrimidine was used instead of 8-bromoquinoline in the synthesis of Compound 10.
MS[M+H]+＝705.83
Production examples 4 to 12: synthesis of Compound 12
Compound 12 was synthesized in the same manner as described above except that 2- (4-chlorophenyl) -4, 6-diphenyl-1, 3, 5-triazine was used instead of 8-bromoquinoline for the synthesis of compound 10.
MS[M+H]+＝732.86
Example 1
ITO (indium tin oxide) is addedThe glass substrate (corning 7059 glass) coated with a thin film was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fisher Co, and the distilled water used was distilled water obtained by twice filtering with a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.
On the ITO transparent electrode thus prepared, HAT (hexanitrile hexaazatriphenylene) was added as a precursor
The thickness of (3) was subjected to thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, HT1 as a substance for transporting holes
After forming a hole transport layer by vacuum evaporation, HT2 was formed in a film thickness on the hole transport layerVacuum evaporation is performed to form a hole control layer. On the above hole-regulating layer, a host H1 and a dopant D1 compound (25:1) are addedThe thickness of (2) is vacuum-evaporated to form a light-emitting layer. Next, on the above-mentioned light-emitting layer, ETM1 compound is added
Is deposited in vacuum to form an electron control layer, and then the compound 1 and LiQ (1:1) synthesized in production example 4-1 are deposited on the electron control layer
The electron transport layers are sequentially formed by vacuum deposition. On the electron transport layer, lithium fluoride (LiF) is sequentially added
Thickness of (2), adding Mg and Ag (10:1) toIs evaporated and then is evaporatedThe cathode was formed of aluminum in a thickness to manufacture an organic light emitting element.
In the above process, the evaporation speed of the organic material is maintained
Maintenance of lithium fluoride
The deposition rate of aluminum is maintained at 3 to 3The deposition rate of (3).
Examples 2 to 16
An organic light-emitting element was produced in the same manner as in example 1, except that compounds shown in table 1 below and LIQ (1:1) were used in a specific ratio as an electron transport layer instead of compound 1 and LIQ.
Example 17
An organic light-emitting element was produced in the same manner as in example 1, except that compound 1 was used instead of ETM1 for the electron control layer and ETM2 was used instead of compound 1 for the electron transport layer.
Examples 18 to 23
In example 17, an organic light-emitting element was produced by the same method except that in the electron-transporting layer, compounds described in table 2 below were used instead of compound 1 as the electron-adjusting layer, and ETM2 and LIQ were used in specific ratios described in table 2 below.
Examples 24 to 32
In example 1, an experiment was performed by the same method except that the compound described in table 3 below was used in place of ETM1 as the electron adjusting layer and the compound described in table 3 below was used in a specific ratio in place of compound 1 and LIQ (1:1) as the electron transporting layer.
Comparative examples 1 to 11
In example 1, an experiment was performed by the same method except that the compound described in table 3 below was used in place of ETM1 as the electron adjusting layer and the compound described in table 3 below was used in a specific ratio in place of compound 1 and LIQ (1:1) as the electron transporting layer.
Current (20 mA/cm) was applied to the organic light-emitting elements manufactured in examples 1 to 32 and comparative examples 1 to 11 described above2) The voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in tables 1 to 3 below, respectively.
[ Table 1]
[ Table 2]
[ Table 3]
From tables 1 to 3 described above, it was confirmed that examples 1 to 32 exhibited excellent characteristics of low voltage, remarkable efficiency and lifetime as compared with comparative examples 1 to 11.
[ notation ] to show
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: hole adjusting layer 8: luminescent layer
9: electron adjusting layer 10: an electron transport layer.
Claims (10)
1, kinds of compounds represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the metal oxide is represented by,
Y1and Y2Each independently is hydrogen; substituted or unsubstituted C1-40An alkyl group; substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing O, N, Si and or more of S2-60(ii) a heteroaryl group, wherein,
ar is substituted or unsubstituted C containing O, N, Si and or more of S2-60A heteroaryl group; phenyl substituted with cyano; triphenylsilane; or a diphosphine oxide, or a mixture of diphosphine oxides,
each L is independently a direct bond; substituted or unsubstituted C6-60Arylene, or C containing a heteroatom selected from N, O, S and any or more of Si2-60A heteroarylene group, a heteroaryl group,
R1to R3Each independently is halogen; a hydroxyl group; a cyano group; a nitrile group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substitutionOr unsubstituted C1-60A thioalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C1-60A haloalkoxy group; substituted or unsubstituted C3-60A cycloalkyl group; substituted or unsubstituted C1-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing O, N, Si and or more of S2-60(ii) a heteroaryl group, wherein,
m is a number of 0 to 4,
n is a number of from 0 to 2,
o is a number of from 0 to 3,
z is 1 to 4, but o + z is 4 or less.
2. The compound of claim 1, wherein Y1And Y2Each independently being methyl or phenyl.
3. The compound of claim 1, wherein m, n, and o are 0.
4. The compound of claim 1, wherein z is 1.
5. The compound according to claim 1, wherein the chemical formula 1 is any selected from the compounds represented by the following chemical formulae 1-1 to 1-8:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1 to 3
Chemical formulas 1 to 4
Chemical formulas 1 to 5
Chemical formulas 1 to 6
Chemical formulas 1 to 7
Chemical formulas 1 to 8
In the chemical formulas 1-1 to 1-8,
the descriptions of L and Ar are the same as defined in claim 1.
6. The compound of claim 1, wherein each Ar is independently any selected from the following structures:
X1to X4Each independently is N or CR', but at least or more of them are N,
r' is hydrogen, or substituted or unsubstituted C1-60The alkyl group of (a) is,
X5is N, S or O, and the content of the active carbon,
R4and R5Each independently is halogen; a hydroxyl group; cyanogen (CN)A group; a nitrile group; a nitro group; an amino group; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60A haloalkyl group; substituted or unsubstituted C1-60A thioalkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C1-60A haloalkoxy group; substituted or unsubstituted C3-60An epoxy group; substituted or unsubstituted C1-60An alkenyl group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C6-60Aryloxy group, or substituted or unsubstituted C containing O, N, Si and or more of S2-60A heteroaryl group.
7. The compound of claim 1, wherein each L is independently a direct bond or any selected from the following structures.
8. The compound of claim 1, wherein the compound represented by chemical formula 1 is any selected from the group consisting of:
9, kinds of organic light-emitting elements, which comprises a th electrode, a second electrode provided so as to face the th electrode, and an organic layer having or more layers between the th electrode and the second electrode, wherein or more layers of the organic layer contain the compound according to any of claims 1 to 8.
10. The organic light-emitting element according to claim 9, wherein the organic layer containing the compound is an electron-transporting layer, an electron-modulating layer, an electron-injecting layer, a hole-blocking layer, or a light-emitting layer.
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| CN113582966A (en) * | 2021-07-28 | 2021-11-02 | 西安瑞联新材料股份有限公司 | 2-bromodibenzo [1,4] dioxane compound, preparation method and application |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130064601A (en) * | 2011-12-08 | 2013-06-18 | 주식회사 두산 | Novel compounds and organic electro luminescence device using the same |
| CN105121594A (en) * | 2012-09-28 | 2015-12-02 | 第一毛织株式会社 | Compound for organic optoelectronic device, organic light-emitting device containing same, and display device including said organic light-emitting device |
| KR20160010706A (en) * | 2014-07-17 | 2016-01-28 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light-emitting device including the same |
| KR20160076367A (en) * | 2014-12-22 | 2016-06-30 | 주식회사 두산 | Organic compound and organic electroluminescent device comprising the same |
| CN106279055A (en) * | 2015-05-12 | 2017-01-04 | 上海和辉光电有限公司 | A kind of indeno anthracene compound of miscellaneous generation and application thereof |
| CN106458961A (en) * | 2014-04-09 | 2017-02-22 | 株式会社斗山 | Organic compound and organic electroluminescent element comprising same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100430549B1 (en) | 1999-01-27 | 2004-05-10 | 주식회사 엘지화학 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
-
2018
- 2018-07-27 KR KR1020180088201A patent/KR102103506B1/en active IP Right Grant
- 2018-08-07 CN CN201880039613.2A patent/CN110741002B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130064601A (en) * | 2011-12-08 | 2013-06-18 | 주식회사 두산 | Novel compounds and organic electro luminescence device using the same |
| CN105121594A (en) * | 2012-09-28 | 2015-12-02 | 第一毛织株式会社 | Compound for organic optoelectronic device, organic light-emitting device containing same, and display device including said organic light-emitting device |
| CN106458961A (en) * | 2014-04-09 | 2017-02-22 | 株式会社斗山 | Organic compound and organic electroluminescent element comprising same |
| KR20160010706A (en) * | 2014-07-17 | 2016-01-28 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light-emitting device including the same |
| KR20160076367A (en) * | 2014-12-22 | 2016-06-30 | 주식회사 두산 | Organic compound and organic electroluminescent device comprising the same |
| CN106279055A (en) * | 2015-05-12 | 2017-01-04 | 上海和辉光电有限公司 | A kind of indeno anthracene compound of miscellaneous generation and application thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112010866A (en) * | 2020-09-07 | 2020-12-01 | 京东方科技集团股份有限公司 | Dioxin compound and preparation method and application thereof |
| CN113582966A (en) * | 2021-07-28 | 2021-11-02 | 西安瑞联新材料股份有限公司 | 2-bromodibenzo [1,4] dioxane compound, preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20190043456A (en) | 2019-04-26 |
| KR102103506B1 (en) | 2020-04-22 |
| CN110741002B (en) | 2023-12-05 |
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