JP7210858B2 - 新規な化合物およびこれを利用した有機発光素子 - Google Patents
新規な化合物およびこれを利用した有機発光素子 Download PDFInfo
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- JP7210858B2 JP7210858B2 JP2020500742A JP2020500742A JP7210858B2 JP 7210858 B2 JP7210858 B2 JP 7210858B2 JP 2020500742 A JP2020500742 A JP 2020500742A JP 2020500742 A JP2020500742 A JP 2020500742A JP 7210858 B2 JP7210858 B2 JP 7210858B2
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- 150000001875 compounds Chemical class 0.000 title claims description 152
- 239000010410 layer Substances 0.000 claims description 125
- 239000000126 substance Substances 0.000 claims description 71
- -1 biphenylyl Chemical group 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 238000002347 injection Methods 0.000 claims description 28
- 239000007924 injection Substances 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 239000012044 organic layer Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 125000004431 deuterium atom Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 description 50
- 238000004519 manufacturing process Methods 0.000 description 25
- 230000032258 transport Effects 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
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- 239000011368 organic material Substances 0.000 description 15
- 229940125904 compound 1 Drugs 0.000 description 13
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- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 9
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- 150000004982 aromatic amines Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 4
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007773 negative electrode material Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- 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 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 3
- MQRGCMXCVJPWHI-UHFFFAOYSA-N 9,9-diphenylfluoren-2-amine Chemical compound C12=CC(N)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 MQRGCMXCVJPWHI-UHFFFAOYSA-N 0.000 description 3
- ZGAFVMDDUCBXAI-UHFFFAOYSA-N 9-(4-chlorophenyl)phenanthrene Chemical compound C1=CC(Cl)=CC=C1C1=CC2=CC=CC=C2C2=CC=CC=C12 ZGAFVMDDUCBXAI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940126086 compound 21 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000007774 positive electrode material Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000008096 xylene 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
- 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
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- 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
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- 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
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- BNGNNFQSUWVWCW-UHFFFAOYSA-N 3-bromophenanthrene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3C=CC2=C1 BNGNNFQSUWVWCW-UHFFFAOYSA-N 0.000 description 2
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
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- 229910052791 calcium Inorganic materials 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- BXXLTVBTDZXPTN-UHFFFAOYSA-N methyl 2-iodobenzoate Chemical compound COC(=O)C1=CC=CC=C1I BXXLTVBTDZXPTN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 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
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 238000010992 reflux Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 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
- 125000001113 thiadiazolyl group Chemical group 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
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 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
- 238000007740 vapor deposition Methods 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Description
本出願は、2017年11月10日付の韓国特許出願第10-2017-0149680号および2018年9月13日付の韓国特許出願第10-2018-0109532号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として含まれる。
[化学式1]
R1、R2、R4およびR5は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換または非置換の炭素数1~60のアルキル、置換または非置換の炭素数1~60のアルコキシ、置換または非置換の炭素数1~60のチオアルキル、置換または非置換の炭素数3~60のシクロアルキル、置換または非置換の炭素数6~60のアリール、またはトリ(炭素数1~60のアルキル)シリルであり、
a、bおよびdは、それぞれ独立して、0~4の整数であり、
eは、0~3の整数であり、
L1およびL2は、それぞれ独立して、単一結合;置換または非置換の炭素数6~60のアリーレン;または置換または非置換のN、O、およびSで構成される群から選択されるいずれか一つ以上のヘテロ原子を含む炭素数2~60のヘテロアリーレンであり、
Ar1は、下記化学式2で表され、
[化学式2]
Ra、RbおよびRcのうちの一つがL1との結合手であり、残りは水素であり、
R3は、水素、重水素、ハロゲン、シアノ、置換または非置換の炭素数1~60のアルキル、置換または非置換の炭素数1~60のアルコキシ、置換または非置換の炭素数1~60のチオアルキル、置換または非置換の炭素数3~60のシクロアルキル、置換または非置換の炭素数6~60のアリール、またはトリ(炭素数1~60のアルキル)シリルであり、
cは、0~7の整数であり、
Ar2は、フェニル、ビフェニリル、ターフェニリル、クォーターフェニリル、ナフチル、ジメチルフルオレニル、トリフェニレニル、下記化学式3aで表される置換基、および下記化学式3bで表される置換基で構成される群から選択されるいずれか一つのアリール;またはジベンゾフラニルおよびジベンゾチオフェニルで構成される群から選択されるいずれか一つのヘテロアリールであり、前記Ar2は、非置換または1~5個の重水素で置換され、
[化学式1-1]
L1およびL2は、それぞれ独立して、単一結合;またはフェニレンであり、
Ar2は、フェニル、ビフェニリル、ターフェニリル、クォーターフェニリル、ナフチル、ジメチルフルオレニル、トリフェニレニル、下記化学式3aで表される置換基、および下記化学式3bで表される置換基で構成される群から選択されるいずれか一つのアリール;またはジベンゾフラニルおよびジベンゾチオフェニルで構成される群から選択されるいずれか一つのヘテロアリールであり、前記Ar2は、非置換または1~5個の重水素で置換される:
[化学式1-3]
L1およびL2は、それぞれ独立して、単一結合;またはフェニレンであり、
Ar2は、フェニル、ビフェニリル、ターフェニリル、クォーターフェニリル、ナフチル、ジメチルフルオレニル、トリフェニレニル、下記化学式3aで表される置換基、および下記化学式3bで表される置換基で構成される群から選択されるいずれか一つのアリールであり、前記Ar2は、非置換または1~5個の重水素で置換される:
[反応式1]
9,9-ジフェニル-9H-フルオレン-2-アミン(30g、89.97mmol)と、9-ブロモフェナントレン(23.6g、91.77mmol)、およびソジウム-t-ブトキシド(12.11g、125.9mol)をトルエンに入れて加熱攪拌した後、還流させ、[1,1'-ビス(ジフェニルホスフィノ)フェロセン]ジクロロパラジウム(658mg、1mol%)を入れた。常温に温度を下げ、反応を終了した後、テトラヒドロフランと酢酸エチルを使用して再結晶して、化合物A1(38.9g、収率85%)を製造した。
MS[M+H]+=510.65
前記化合物A1の製造で9-ブロモフェナントレンの代わりに2-ブロモフェナントレンを使用したことを除いては同様の方法で、化合物A2を製造した。
MS[M+H]+=510.65
前記化合物A1の製造で9-ブロモフェナントレンの代わりに3-ブロモフェナントレンを使用したことを除いては同様の方法で、化合物A3を製造した。
MS[M+H]+=510.65
前記化合物A1の製造で9-ブロモフェナントレンの代わりに4-ブロモビフェニルを使用したことを除いては同様の方法で、化合物A4を製造した。
MS[M+H]+=486.63
前記化合物A1の製造で9-ブロモフェナントレンの代わりに4-ブロモ-1,1';4',1''-ターフェニルを使用したことを除いては同様の方法で、化合物A5を製造した。
MS[M+H]+=562.73
前記化合物A1の製造で9-ブロモフェナントレンの代わりに4-ブロモ-ジベンゾ[b,d]フランを使用したことを除いては同様の方法で、化合物A6を製造した。
MS[M+H]+=500.61
2-ブロモ-9H-フルオレン(100g、407.96mmol)と50wt%ソジウムヒドロキシド水溶液(70g、897.51mmol)をジメチルスルホキシド(1000ml)に添加した後、160℃で1,4-ジブロモブタン(88.09g、407.96mmol)を滴下し、3時間加熱および攪拌した。常温に温度を下げ、反応を終了した後、トルエンおよび水で抽出した後、カラム精製して、前記a1化合物(アイボリー色の液体、120g、収率98%)を製造した。
MS[M+H]+=299.14
化合物a1(10g、33.55mmol)と9,9'-ジフェニル-9H-フルオレン-2-アミン(11.29g、33.89mmol)、およびソジウム-t-ブトキシド(4.5g、46.97mol)をトルエンに入れて加熱および攪拌した後、還流させ、[1,1'-ビス(ジフェニルホスフィノ)フェロセン]ジクロロパラジウム(490mg、2mmol%)を入れた。常温に温度を下げ、反応を終了した後、クロロホルムと酢酸エチルを使用して再結晶して、化合物A2を製造した。
MS[M+H]+=552.26
9-ブロモフェナントレン(50g、194.4mmol)と4-クロロフェニルボロン酸(31.93g、204.1mmol)をテトラヒドロフラン(300ml)に添加した後、2M炭酸カリウム水溶液(150ml)を添加し、テトラキストリフェニル-ホスフィノパラジウム(4.5g、2mol%)を入れた後、10時間加熱および攪拌した。常温に温度を下げ、反応を終了した後、炭酸カリウム水溶液を除去して層分離した。溶媒の除去後、白い固体を酢酸エチルで再結晶して、前記化合物B1(50.53g、収率90%)を製造した。
MS[M+H]+=289.77
前記化合物B1の製造で4-クロロフェニルボロン酸の代わりに3-クロロフェニルボロン酸を使用したことを除いては同様の方法で、化合物B2を製造した。
MS[M+H]+=289.77
前記化合物B1の製造で4-クロロフェニルボロン酸の代わりに2-クロロフェニルボロン酸を使用したことを除いては同様の方法で、化合物B3を製造した。
MS[M+H]+=289.77
前記化合物B1の製造で9-ブロモフェナントレンの代わりに3-ブロモフェナントレンを使用し、4-クロロフェニルボロン酸の代わりに3-クロロフェニルボロン酸を使用したことを除いては同様の方法で、化合物B2を製造した。
MS[M+H]+=289.77
実施例1:化合物1の製造
MS[M+H]+=662.85
MS[M+H]+=712.91
MS[M+H]+=702.91
MS[M+H]+=712.91
MS[M+H]+=738.95
MS[M+H]+=676.83
MS[M+H]+=752.93
MS[M+H]+=738.95
MS[M+H]+=815.04
MS[M+H]+=752.93
MS[M+H]+=804.36
段階1)化合物1-Aの製造
MS[M+H]+=666
MS[M+H]+=742
MS[M+H]+=742
段階1)化合物4-Aの製造
MS[M+H]+=667
MS[M+H]+=667
MS[M+H]+=743
MS[M+H]+=671
段階1)化合物8-Aの製造
MS[M+H]+=747
MS[M+H]+=751
段階1)化合物10-Aの製造
MS[M+H]+=665
MS[M+H]+=665
実験例1-1
ITO(インジウムスズ酸化物)が1,000Åの厚さに薄膜コーティングされたガラス基板(corning 7059 glass)を、分散剤を溶かした蒸留水に入れて超音波洗浄した。洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次ろ過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行した。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノール溶剤の順に超音波洗浄をし乾燥させた。
こうして準備されたITO透明電極上に、下記HI-1化合物を500Åの厚さに熱真空蒸着して正孔注入層を形成した。前記正孔注入層上に、前記製造した化合物1を900Åの厚さに真空蒸着して正孔輸送層を形成した後、次いで、前記正孔輸送層上に下記HT2化合物を50Åの厚さに真空蒸着して正孔調節層を形成した。前記正孔調節層上に、下記H1化合物と下記D1化合物を25:1の重量比で300Åの厚さに真空蒸着して発光層を形成した。前記発光層上に、下記E1化合物を300Åの厚さに真空蒸着して電子輸送層を形成した。前記電子輸送層上に、順次に12Å厚さのフッ化リチウム(LiF)と2,000Å厚さのアルミニウムを蒸着して負極を形成して、有機発光素子を製造した。
前記実験例1-1で正孔輸送層として化合物1の代わりに下記表1に記載される化合物を使用したことを除いては同様の方法で、有機発光素子を製造した。
前記実験例1-1で正孔輸送層として化合物1の代わりに下記表1に記載される化合物を使用したことを除いては同様の方法で、有機発光素子を製造した。下記表1で、HT1、HT3、HT4、HT7、およびHT8の化合物は以下の通りである。
ITO(インジウムスズ酸化物)が1,000Åの厚さに薄膜コーティングされたガラス基板(corning 7059 glass)を、分散剤を溶かした蒸留水に入れて超音波洗浄した。洗剤としてはフィッシャー社(Fischer Co.)製品を使用し、蒸留水としてはミリポア社(Millipore Co.)製品のフィルタ(Filter)で2次ろ過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返し超音波洗浄を10分間進行した。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノール溶剤の順に超音波洗浄をし乾燥させた。
前記実験例2-1で正孔輸送層および正孔調節層として下記表2に記載される化合物を使用したことを除いては同様の方法で、有機発光素子を製造した。
前記実験例2-1で正孔輸送層および正孔調節層として下記表2に記載される化合物を使用したことを除いては同様の方法で、有機発光素子を製造した。下記表2で、HT3、HT4、HT5、HT7、およびHT8の化合物は以下の通りである。
2:正極
3:発光層
4:負極
5:正孔注入層
6:正孔輸送層
7:正孔調節層
8:電子輸送層
Claims (10)
- 下記化学式1で表される化合物:
[化学式1]
R1、R2、R4およびR5は、それぞれ独立して、水素、または重水素であり、
a、bおよびdは、それぞれ独立して、0~4の整数であり、
eは、0~3の整数であり、
L1およびL2は、それぞれ独立して、単一結合;または重水素で置換または非置換の炭素数6~60のアリーレンであり、
Ar1は、下記化学式2で表され、
[化学式2]
R a は水素であり、RbおよびRcのうちの一つがL1との結合手であり、残りは水素であり、
R3は、水素、または重水素であり、
cは、0~7の整数であり、
Ar2は、フェニル、ビフェニリル、ターフェニリル、クォーターフェニリル、ナフチル、トリフェニレニル、下記化学式3aで表される置換基、および下記化学式3bで表される置換基で構成される群から選択されるいずれか一つのアリール;またはジベンゾフラニルおよびジベンゾチオフェニルで構成される群から選択されるいずれか一つのヘテロアリールであり、前記Ar2は、非置換または1~5個の重水素で置換され、
- R1、R2およびR4は、水素である、請求項1に記載の化合物。
- L1は、単一結合;非置換、または1~4個の重水素で置換されたフェニレン;または非置換、または1~8個の重水素で置換されたビフェニリレンである、請求項1または2に記載の化合物。
- R3は水素である、請求項1から3のいずれか一項に記載の化合物。
- 上記化学式1で表される化合物は、下記化学式1-2で表される、請求項1に記載の化合物:
[化学式1-2]
L1およびL2は、それぞれ独立して、単一結合;非置換、または1~4個の重水素で置換されたフェニレン;または非置換、または1~8個の重水素で置換されたビフェニリレンであり、
Ar2は、フェニル、ビフェニリル、ターフェニリル、クォーターフェニリル、ナフチル、トリフェニレニル、下記化学式3aで表される置換基、および下記化学式3bで表される置換基で構成される群から選択されるいずれか一つのアリール;またはジベンゾフラニルおよびジベンゾチオフェニルで構成される群から選択されるいずれか一つのヘテロアリールであり、前記Ar2は、非置換または1~5個の重水素で置換される:
- 下記化学式1で表される化合物:
[化学式1]
R1、R2、R4およびR5は、それぞれ独立して、水素、または重水素であり、
a、bおよびdは、それぞれ独立して、0~4の整数であり、
eは、0~3の整数であり、
L1は、重水素で置換または非置換の炭素数6~60のアリーレンであり、
L2は、単一結合;または重水素で置換または非置換の炭素数6~60のアリーレンであり、
Ar1は、下記化学式2で表され、
[化学式2]
RaがL1との結合手であり、 RbおよびRcは、水素であり、
R3は、水素、または重水素であり、
cは、0~7の整数であり、
Ar2は、フェニル、ビフェニリル、ターフェニリル、クォーターフェニリル、ナフチル、トリフェニレニル、下記化学式3aで表される置換基、および下記化学式3bで表される置換基で構成される群から選択されるいずれか一つのアリール;またはジベンゾフラニルおよびジベンゾチオフェニルで構成される群から選択されるいずれか一つのヘテロアリールであり、前記Ar2は、非置換または1~5個の重水素で置換される。
- 第1電極と、前記第1電極と対向して備えられた第2電極と、前記第1電極と前記第2電極との間に備えられた1層以上の有機物層とを含む有機発光素子であって、前記有機物層のうちの1層以上は、請求項1~8のいずれか一項に記載の化合物を含む、有機発光素子。
- 第1電極と、前記第1電極と対向して備えられた第2電極と、前記第1電極と前記第2電極との間に備えられた1層以上の有機物層とを含む有機発光素子であって、前記有機物層は、正孔注入層、正孔輸送層、正孔調節層、発光層、および電子輸送層を含み、前記正孔調節層は、下記化学式1で表される化合物を含む、有機発光素子:
[化学式1]
R1、R2、R4およびR5は、それぞれ独立して、水素、または重水素であり、
a、bおよびdは、それぞれ独立して、0~4の整数であり、
eは、0~3の整数であり、
L1およびL2は、それぞれ独立して、単一結合;または重水素で置換または非置換の炭素数6~60のアリーレンであり、
Ar1は、下記化学式2で表され、
[化学式2]
Ra、RbおよびRcのうちの一つがL1との結合手であり、残りは水素であり、
R3は、水素、または重水素であり、
cは、0~7の整数であり、
Ar2は、フェニル、ビフェニリル、ターフェニリル、クォーターフェニリル、ナフチル、トリフェニレニル、下記化学式3aで表される置換基、および下記化学式3bで表される置換基で構成される群から選択されるいずれか一つのアリール;またはジベンゾフラニルおよびジベンゾチオフェニルで構成される群から選択されるいずれか一つのヘテロアリールであり、前記Ar2は、非置換または1~5個の重水素で置換され、
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TW201922686A (zh) | 2019-06-16 |
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