JP6638926B2 - ヘテロ環化合物およびこれを含む有機発光素子 - Google Patents
ヘテロ環化合物およびこれを含む有機発光素子 Download PDFInfo
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- JP6638926B2 JP6638926B2 JP2018508222A JP2018508222A JP6638926B2 JP 6638926 B2 JP6638926 B2 JP 6638926B2 JP 2018508222 A JP2018508222 A JP 2018508222A JP 2018508222 A JP2018508222 A JP 2018508222A JP 6638926 B2 JP6638926 B2 JP 6638926B2
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 30
- 239000010410 layer Substances 0.000 claims description 187
- 150000001875 compounds Chemical class 0.000 claims description 137
- 239000000126 substance Substances 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000011368 organic material Substances 0.000 claims description 24
- 230000005525 hole transport Effects 0.000 claims description 22
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 22
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 21
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 21
- 230000000903 blocking effect Effects 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 18
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 125000006267 biphenyl group Chemical group 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 7
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 7
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Chemical group 0.000 claims description 3
- 125000005580 triphenylene group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- UTAHFAJHGGPJEQ-UHFFFAOYSA-N (2-phenylphenyl)phosphane Chemical compound PC1=CC=CC=C1C1=CC=CC=C1 UTAHFAJHGGPJEQ-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 153
- -1 nitro, hydroxy, carbonyl Chemical group 0.000 description 88
- 125000003118 aryl group Chemical group 0.000 description 68
- 125000004432 carbon atom Chemical group C* 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 230000032258 transport Effects 0.000 description 40
- 238000002347 injection Methods 0.000 description 39
- 239000007924 injection Substances 0.000 description 39
- 125000001072 heteroaryl group Chemical group 0.000 description 35
- 238000004519 manufacturing process Methods 0.000 description 35
- 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 28
- 125000002950 monocyclic group Chemical group 0.000 description 28
- 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 28
- 239000000758 substrate Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000012153 distilled water Substances 0.000 description 25
- 239000000463 material Substances 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 125000003367 polycyclic group Chemical group 0.000 description 23
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 22
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 19
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000004140 cleaning Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 14
- 229910052782 aluminium Inorganic materials 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000003599 detergent Substances 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- 238000004506 ultrasonic cleaning Methods 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000010409 thin film Substances 0.000 description 7
- 125000005264 aryl amine group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 125000005567 fluorenylene group Chemical group 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000005549 heteroarylene group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 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 5
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical class C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000005241 heteroarylamino group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
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- 238000007738 vacuum evaporation Methods 0.000 description 5
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- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 0 CC1(C)c(cc2[o]c3cccc(I*)c3c2c2)c2-c2ccccc12 Chemical compound CC1(C)c(cc2[o]c3cccc(I*)c3c2c2)c2-c2ccccc12 0.000 description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 4
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
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- 125000005165 aryl thioxy group Chemical group 0.000 description 4
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
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- AFBZMKWCZFFWIC-HVEFNXCZSA-N (3s)-3-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-sulfanylpropanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-[ Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@@H](N)C(C)C)C1=CNC=N1 AFBZMKWCZFFWIC-HVEFNXCZSA-N 0.000 description 3
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- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 3
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- 239000000956 alloy Substances 0.000 description 3
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 125000005566 carbazolylene group Chemical group 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- HGDIHUZVQPKSMO-UHFFFAOYSA-N methylphosphonoylmethane Chemical group CP(C)=O HGDIHUZVQPKSMO-UHFFFAOYSA-N 0.000 description 3
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- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
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- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- NJVSFOMTEFOHMI-UHFFFAOYSA-N n,2-diphenylaniline Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1NC1=CC=CC=C1 NJVSFOMTEFOHMI-UHFFFAOYSA-N 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HCISEFFYVMEPNF-UHFFFAOYSA-N n-phenyl-9h-fluoren-1-amine Chemical group C=12CC3=CC=CC=C3C2=CC=CC=1NC1=CC=CC=C1 HCISEFFYVMEPNF-UHFFFAOYSA-N 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 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
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 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
- 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 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
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 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
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 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
- 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
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 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
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl 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
- 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
- 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 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
- 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
- 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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- Furan Compounds (AREA)
Description
[化学式1]
R1およびR2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアルキル基であり、
R3〜R5は、互いに同一または異なり、それぞれ独立に、水素;重水素;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミド基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアミン基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
L1は、直接結合;置換もしくは非置換の単環もしくは2環のアリーレン基;置換もしくは非置換のフェナントレニレン基;置換もしくは非置換のフェニレニレン基;置換もしくは非置換のフルオレニレン基;置換もしくは非置換の4環以上のアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、
Ar1は、置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
r3は、1〜4の整数であり、
r4は、1または2であり、
r5は、1〜3の整数であり、
r3〜r5がそれぞれ複数の場合、複数の括弧内の構造は、互いに同一または異なる。
[化学式2]
R1〜R5、r3〜r5、L1およびAr1の定義は、前記化学式1と同じである。
[化学式6]
L1およびAr1の定義は、前記化学式1と同じである。
[化学式7]
L1およびAr1の定義は、前記化学式1と同じである。
−−−−は、前記L1を介して化学式1に結合する部位を意味する。
[化学式a]
X1〜X12のうちのいずれか1つは、前記L1を介して化学式1に結合する部位であり、残りは、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であるか、隣接した基は互いに連結されて、置換もしくは非置換の環を形成する。
前記Ar1は、重水素;フッ素基;ニトリル基;メチル基;t−ブチル基;フェニル基;ビフェニル基;ナフチル基;フルオレニル基;フェナントレニル基;カルバゾリル基;ベンゾカルバゾリル基;ピリジル基;トリアジニル基;トリフェニレニル基;ピリミジル基;キノリニル基;ジベンゾフラニル基;ジベンゾチオフェン基;ベンズイミダゾリル基;ベンゾチアゾリル基;ベンズオキサゾリル基;チオフェン基;ジメチルホスフィンオキシド基;ジフェニルホスフィンオキシド基;ジナフチルホスフィンオキシド基;トリメチルシリル基;トリフェニルシリル基;および
[A−1]
[一般式1]
[反応式1]
MS[M+H]+=526
MS[M+H]+=451
MS[M+H]+=516
MS[M+H]+=592
MS[M+H]+=592
MS[M+H]+=592
MS[M+H]+=489
MS[M+H]+=591
MS[M+H]+=526
MS[M+H]+=681
MS[M+H]+=561
MS[M+H]+=553
MS[M+H]+=514
MS[M+H]+=590
ITO(indium tin oxide)が1,000Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、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次濾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分間進行させた。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、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
前記実験例1−1における化合物1の代わりに前記化合物2を用いたことを除けば、実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における化合物1の代わりに下記EB1の化合物を用いたことを除けば、前記実験例1−1と同様の方法で有機発光素子を作製した。
前記実験例1−1における化合物1の代わりに下記EB2の化合物を用いたことを除けば、前記実験例1−1と同様の方法で有機発光素子を作製した。
製造例で製造された化合物を通常知られた方法で高純度昇華精製をした後、下記のような方法で緑色有機発光素子を製造した。
前記比較例2−1におけるCBPの代わりに前記化合物3を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記実験例2における化合物CBPの代わりに前記化合物4を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物5を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物6を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物7を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物8を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物14を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物16を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物20を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物22を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物26を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物28を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物31を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに前記化合物32を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに下記GH1の化合物を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
前記比較例2−1における化合物CBPの代わりに下記GH2の化合物を用いたことを除けば、比較例2−1と同様の方法で有機発光素子を作製した。
製造例で製造された化合物を通常知られた方法で高純度昇華精製をした後、下記のような方法で赤色有機発光素子を製造した。
前記実験例3−1における化合物7の代わりに前記化合物CBPを用いたことを除けば、実験例3−1と同様の方法で有機発光素子を作製した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物3を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物4を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物5を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物6を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物8を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物13を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物14を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物15を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物16を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物18を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物19を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物20を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物21を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物22を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物25を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物26を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物27を用いたことを除けば、同様に実験した。
前記実験例1−1において、前記電子輸送層としてET1の代わりに化合物28を用いたことを除けば、同様に実験した。
前記実験例4−1において、前記電子輸送層として化合物3の代わりに下記ET2の化合物を用いたことを除けば、同様の方法で有機発光素子を作製した。
前記実験例4−1において、前記電子輸送層として化合物3の代わりに下記ET3の化合物を用いたことを除けば、同様の方法で有機発光素子を作製した。
ITO(indium tin oxide)が1,000Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、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次濾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分間進行させた。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、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
[HAT]
[EBL]
[BH]
前記比較例5におけるR−1の代わりに前記化合物ET−2を用いたことを除けば、比較例5と同様の方法で有機発光素子を作製した。
前記比較例5におけるR−1の代わりに前記化合物ET−3を用いたことを除けば、比較例5と同様の方法で有機発光素子を作製した。
前記比較例5におけるR−1の代わりに前記化合物ET−4を用いたことを除けば、比較例5と同様の方法で有機発光素子を作製した。
前記比較例5におけるR−1の代わりに前記化合物ET−5を用いたことを除けば、比較例5と同様の方法で有機発光素子を作製した。
前記比較例5におけるR−1の代わりに前記化合物ET−6を用いたことを除けば、比較例5と同様の方法で有機発光素子を作製した。
ITO(indium tin oxide)が1,000Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、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次濾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分間進行させた。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、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
[HAT]
[EBL]
[GH]
前記比較例6におけるR−2の代わりに前記化合物ET−4を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−5を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−6を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−7を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−8を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−9を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−10を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−11を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−15を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−2を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−3を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−13を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−14を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−12を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
前記比較例6におけるR−2の代わりに前記化合物ET−16を用いたことを除けば、比較例6と同様の方法で有機発光素子を作製した。
ITO(indium tin oxide)が1,000Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、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次濾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分間進行させた。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、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機に基板を輸送させた。
[EBL]
[BH]
前記比較例7におけるR−3の代わりに前記化合物ET−4を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−5を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−6を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−9を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−10を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−17を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−11を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−18を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−2を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−13を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−14を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−15を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−16を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−19を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
前記比較例7におけるR−3の代わりに前記化合物ET−20を用いたことを除けば、比較例7と同様の方法で有機発光素子を作製した。
20:基板
30:第1電極
40:発光層
50:第2電極
60:正孔注入層
70:正孔輸送層
80:電子輸送層
90:電子注入層
Claims (9)
- 下記化学式1で表されるヘテロ環化合物:
[化学式1]
R1およびR2は、メチル基であり、
R3〜R5は、水素であり、
L1は、直接結合;2価のフェニル基;または2価のカルバゾール基であり、
Ar1は、フェナントレン基;トリフェニレン基;ジメチルフルオレン基;ナフチル基;ジベンゾフラン基;ジベンゾチオフェン基;フェニル基で置換のピリジン基;フェニル基、ビフェニル基、あるいはナフチル基で置換あるいは非置換のカルバゾール基;ベンゾカルバゾール基;フェニル基で置換のベンゾイミダゾール基;フェニル基、ビフェニル基、ジメチルフルオレン基、ジベンゾフラン基、あるいはジベンゾチオフェン基で置換のトリアジン基;フェニル基、ジベンゾフラン基、ジメチルフルオレン基、ナフチル基、あるいはビフェニル基で置換のキナゾリン基;フェニル基あるいはビフェニル基で置換のピリミジン基;またはビフェニルホスフィンオキシド基であり、
r3は、1〜4の整数であり、
r4は、1または2であり、
r5は、1〜3の整数であり、
r3〜r5がそれぞれ複数の場合、複数の括弧内の構造は、互いに同一または異なる。 - 前記化学式1は、下記化学式2〜5のうちのいずれか1つで表されるものである、
請求項1に記載のヘテロ環化合物:
[化学式2]
R1〜R5、r3〜r5、L1およびAr1の定義は、前記化学式1と同じである。 - 前記化学式1は、
下記化合物の中から選択されるいずれか1つである、
請求項1に記載のヘテロ環化合物:
- 第1電極と、
前記第1電極に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層または2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1〜3のいずれか1項に記載のヘテロ環化合物を含むものである
有機発光素子。 - 前記有機物層は、正孔輸送層を含み、
前記正孔輸送層は、前記ヘテロ環化合物を含むものである、
請求項4に記載の有機発光素子。 - 前記有機物層は、電子阻止層を含み、
前記電子阻止層は、前記ヘテロ環化合物を含むものである、
請求項4に記載の有機発光素子。 - 前記有機物層は、電子輸送層を含み、
前記電子輸送層は、前記ヘテロ環化合物を含むものである、
請求項4に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、前記ヘテロ環化合物を含むものである、
請求項4に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、前記ヘテロ環化合物を前記発光層のホストとして含むものである、
請求項4に記載の有機発光素子。
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PCT/KR2017/001998 WO2017146483A1 (ko) | 2016-02-23 | 2017-02-23 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
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TWI638811B (zh) | 2018-10-21 |
CN108026061B (zh) | 2021-08-17 |
US20180261777A1 (en) | 2018-09-13 |
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