JP6806341B2 - 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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- JP6806341B2 JP6806341B2 JP2017543999A JP2017543999A JP6806341B2 JP 6806341 B2 JP6806341 B2 JP 6806341B2 JP 2017543999 A JP2017543999 A JP 2017543999A JP 2017543999 A JP2017543999 A JP 2017543999A JP 6806341 B2 JP6806341 B2 JP 6806341B2
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 34
- -1 spirobifluorenyl group Chemical group 0.000 claims description 190
- 239000010410 layer Substances 0.000 claims description 177
- 239000000126 substance Substances 0.000 claims description 156
- 150000001875 compounds Chemical class 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 238000002347 injection Methods 0.000 claims description 44
- 239000007924 injection Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 239000012044 organic layer Substances 0.000 claims description 28
- 125000003367 polycyclic group Chemical group 0.000 claims description 23
- 230000000903 blocking effect Effects 0.000 claims description 21
- 230000005525 hole transport Effects 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000002560 nitrile group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000006267 biphenyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 150000001555 benzenes Chemical group 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- 125000005462 imide group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 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 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- ACYWVHCCUGTDEW-UHFFFAOYSA-N N-naphthalen-1-yl-9H-fluoren-1-amine Chemical group C1(=CC=CC2=CC=CC=C12)NC1=CC=CC=2C3=CC=CC=C3CC12 ACYWVHCCUGTDEW-UHFFFAOYSA-N 0.000 claims description 4
- WJOZUXJBWJTHQQ-UHFFFAOYSA-N N-phenyl-2-(2-phenylphenyl)aniline Chemical group C1(=CC=CC=C1)NC=1C(=CC=CC=1)C=1C(=CC=CC=1)C1=CC=CC=C1 WJOZUXJBWJTHQQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 4
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000005581 pyrene group Chemical group 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 4
- HCBCBXOFVPCOFI-UHFFFAOYSA-N N-(9H-fluoren-1-yl)-9H-carbazol-1-amine Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)NC1=CC=CC=2C3=CC=CC=C3CC12 HCBCBXOFVPCOFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 3
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- GZQBGAMLHSVJRT-UHFFFAOYSA-N n-(9h-fluoren-1-yl)-9h-fluoren-1-amine Chemical group C1C2=CC=CC=C2C2=C1C(NC=1C=CC=C3C4=CC=CC=C4CC=13)=CC=C2 GZQBGAMLHSVJRT-UHFFFAOYSA-N 0.000 claims description 3
- AEUUKUYCSNXLFJ-UHFFFAOYSA-N n-phenyl-9h-carbazol-1-amine Chemical group C=1C=CC(C2=CC=CC=C2N2)=C2C=1NC1=CC=CC=C1 AEUUKUYCSNXLFJ-UHFFFAOYSA-N 0.000 claims description 3
- UMGBMWFOGBJCJA-UHFFFAOYSA-N n-phenylphenanthren-1-amine Chemical group C=1C=CC(C2=CC=CC=C2C=C2)=C2C=1NC1=CC=CC=C1 UMGBMWFOGBJCJA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 2
- KIITVYZNZTTYIO-UHFFFAOYSA-N N-phenyl-11H-benzo[a]carbazol-1-amine Chemical group C1(=CC=CC=C1)NC1=CC=CC=2C=CC=3C=4C=CC=CC=4NC=3C=21 KIITVYZNZTTYIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- HGDIHUZVQPKSMO-UHFFFAOYSA-N methylphosphonoylmethane Chemical group CP(C)=O HGDIHUZVQPKSMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 4
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical class C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 91
- 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 39
- 229940126062 Compound A Drugs 0.000 description 36
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 33
- 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 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000002950 monocyclic group Chemical group 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 229940125904 compound 1 Drugs 0.000 description 20
- 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 18
- 229940126086 compound 21 Drugs 0.000 description 18
- 230000032258 transport Effects 0.000 description 18
- 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 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 0 CC(*C(C1=C2C=CC=CC12)=N1)=C(c2ccccc2)*1=C(CC1=C(C=CC=C2)C2=C2C=CC=CC2C11)[C@@]2C1=Cc1ccccc1C2 Chemical compound CC(*C(C1=C2C=CC=CC12)=N1)=C(c2ccccc2)*1=C(CC1=C(C=CC=C2)C2=C2C=CC=CC2C11)[C@@]2C1=Cc1ccccc1C2 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 10
- 229940127204 compound 29 Drugs 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000005241 heteroarylamino group Chemical group 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 229940125833 compound 23 Drugs 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 125000005264 aryl amine group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- RSHLUKXTYUYDIN-UHFFFAOYSA-N c(cc1)cc(cc2)c1c1c2c(c(cccc2)c2c2c3cccc2)c3[nH]1 Chemical compound c(cc1)cc(cc2)c1c1c2c(c(cccc2)c2c2c3cccc2)c3[nH]1 RSHLUKXTYUYDIN-UHFFFAOYSA-N 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 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 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000005416 organic matter Substances 0.000 description 4
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 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 3
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- SFMJNHNUOVADRW-UHFFFAOYSA-N n-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(C)=CC=C1N1C(=O)C=CC2=C1C1=CC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=C1N=C2 SFMJNHNUOVADRW-UHFFFAOYSA-N 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 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
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 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
- 238000012546 transfer Methods 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
- 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
- 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
- NVCBVYYESHBQKS-UHFFFAOYSA-L zinc;2-carboxyquinolin-8-olate Chemical compound [Zn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 NVCBVYYESHBQKS-UHFFFAOYSA-L 0.000 description 1
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Description
[化学式1]
L1は、直接結合;置換もしくは非置換のアリーレン基;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、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;置換もしくは非置換のピリジル基;置換もしくは非置換のピリミジル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のピリダジニル基;置換もしくは非置換のピラジニル基;または置換もしくは非置換の多環のヘテロアリール基であり、
R1〜R6のうち、R1とR2、R2とR3、またはR3とR4は互いに結合して、(R7)cで置換された環を形成し、残りは、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、
R7は、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、
a〜cはそれぞれ、1〜4の整数であり、
前記a〜cがそれぞれ2以上の場合、2以上の括弧内の構造は、互いに同一または異なり、
ただし、前記Ar1は、置換もしくは非置換のピリミジル基の場合、L1は、置換もしくは非置換のアリーレン基;または置換もしくは非置換のヘテロアリーレン基である。
[化学式1−1]
L1、Ar1、R1〜R7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;ジフェニルアミン基;ジビフェニルアミン基;N−フェニルビフェニルアミン基;N−フェニルナフチルアミン基;N−ビフェニルナフチルアミン基;N−ナフチルフルオレニルアミン基;N−フェニルフェナントレニルアミン基;N−ビフェニルフェナントレニルアミン基;N−フェニルフルオレニルアミン基;N−フェニルターフェニルアミン基;N−フェナントレニルフルオレニルアミン基;N−ビフェニルフルオレニルアミン基;および
前記−−−−は、前記L1を介して化学式1に結合する部位を意味する。
[A−1]
[反応式1]
[反応式2]
[化学式1−A]
n1は、1以上の整数であり、
Ar7は、置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L4は、直接結合;置換もしくは非置換のアリーレン基;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、
Ar8およびAr9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リール基;置換もしくは非置換のシリル基;置換もしくは非置換のゲルマニウム基;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アリールアルキル基;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、互いに結合して置換もしくは非置換の環を形成してもよいし、
n1が2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
[化学式2−A]
G11は、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、または下記化学式
G12は、フェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−ターフェニル−4−イル基、p−ターフェニル−3−イル基、p−ターフェニル−2−イル基、m−ターフェニル−4−イル基、m−ターフェニル−3−イル基、m−ターフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4"−t−ブチル−p−ターフェニル−4−イル基、または3−フルオランテニル基であり、
G13およびG14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ルコキシ基;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、
g12は、1〜5の整数であり、
g13およびg14はそれぞれ、1〜4の整数であり、
前記g12〜g14がそれぞれ2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
MS[M+H]+=394
MS[M+H]+=419
MS[M+H]+=399
MS[M+H]+=470
MS[M+H]+=494
MS[M+H]+=510
MS[M+H]+=444
MS[M+H]+=561
MS[M+H]+=637
MS[M+H]+=713
MS[M+H]+=677
MS[M+H]+=753
MS[M+H]+=559
MS[M+H]+=559
MS[M+H]+=559
MS[M+H]+=559
MS[M+H]+=725
MS[M+H]+=609
MS[M+H]+=576
MS[M+H]+=560
MS[M+H]+=549
MS[M+H]+=547
MS[M+H]+=625
MS[M+H]+=624
MS[M+H]+=713
MS[M+H]+=625
MS[M+H]+=624
MS[M+H]+=623
MS[M+H]+=522
MS[M+H]+=572
MS[M+H]+=598
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回濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で超音波洗浄を10分間2回繰り返した。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、プラズマ洗浄機に搬送した。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搬送した。
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4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の代わりに前記化合物6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の代わりに前記化合物8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の代わりに前記化合物9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の代わりに前記化合物10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の代わりに前記化合物11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の代わりに前記化合物12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の代わりに前記化合物32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の代わりに前記化合物35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の代わりに前記化合物37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の代わりに前記化合物39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の代わりに前記化合物40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の代わりに前記化合物41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の代わりに前記化合物42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の代わりに前記化合物43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において、電子阻止層としてEB1を用い、正孔輸送層としてNPBの代わりに実験例1−1〜1−16の化合物を用いたことを除けば、同様に実験した。
前記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。
前記実験例3−1における化合物21の代わりに前記化合物22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3−1における化合物21の代わりに前記化合物23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3−1における化合物21の代わりに前記化合物24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3−1における化合物21の代わりに前記化合物25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3−1における化合物21の代わりに前記化合物26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3−1における化合物21の代わりに前記化合物27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3−1における化合物21の代わりに前記化合物28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3−1における化合物21の代わりに前記化合物51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3−1における化合物21の代わりに前記化合物52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3−1における化合物21の代わりに前記化合物53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3−1における化合物21の代わりに前記化合物54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3−1における化合物21の代わりにGH2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3−1における化合物21の代わりにGH3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4−1における化合物29の代わりに前記化合物30を用いたことを除けば、実験例4−1と同様の方法で有機発光素子を作製した。
前記実験例4−1における化合物29の代わりに前記化合物31を用いたことを除けば、実験例4−1と同様の方法で有機発光素子を作製した。
前記実験例4−1における化合物29の代わりに前記化合物59を用いたことを除けば、実験例4−1と同様の方法で有機発光素子を作製した。
前記実験例4−1における化合物29の代わりに前記化合物60を用いたことを除けば、実験例4−1と同様の方法で有機発光素子を作製した。
前記実験例4−1における化合物29の代わりに前記化合物61を用いたことを除けば、実験例4−1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 (17)
- 下記化学式1で表されるヘテロ環化合物:
[化学式1]
L1は、非置換のアリーレン基であり、
Ar1は、重水素;ニトリル基;アルキル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;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;置換もしくは非置換のピリジル基;置換もしくは非置換のピリミジル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のピリダジニル基;置換もしくは非置換のピラジニル基;または置換もしくは非置換の多環のヘテロアリール基であり、
R1〜R6のうち、R1とR2、R2とR3、またはR3とR4の組み合わせのいずれか1つは互いに結合して、(R7)cで置換されたベンゼン環を形成し、残りは、それぞれ水素であり、
R7は、水素であり、
a〜cはそれぞれ、1〜4の整数であり、
前記a〜cがそれぞれ2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
ここで、「置換もしくは非置換の」という用語は、重水素;ハロゲン基;ニトリル基;アルキル基;シリル基;アミン基;ホスフィンオキシド基;アリール基;及びヘテロ環基からなる群より選択された1または2以上の置換基で置換されているか、前記例示された置換基のうちの2以上の置換基が連結された置換基で置換されているか、またはいずれの置換基も有しないことを意味する。 - 前記Ar1は、置換もしくは非置換のフェニル基;置換もしくは非置換のビフェニル基;置換もしくは非置換のフェナントレニル基;置換もしくは非置換のナフチル基;置換もしくは非置換のターフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のアントラセニル基;置換もしくは非置換のクリセニル基;置換もしくは非置換のクォーターフェニル基;置換もしくは非置換のスピロビフルオレニル基;置換もしくは非置換のピレニル基;置換もしくは非置換のトリフェニレニル基;置換もしくは非置換のペリレニル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のピリミジル基;置換もしくは非置換のピリジル基;置換もしくは非置換のキノリニル基;置換もしくは非置換のキナゾリニル基;置換もしくは非置換のベンゾキノリニル基;置換もしくは非置換のフェナントロリニル基;置換もしくは非置換のキノキサリニル基;置換もしくは非置換のジベンゾフラニル基;置換もしくは非置換のジベンゾチオフェン基;置換もしくは非置換のベンゾナフトフラニル;置換もしくは非置換のベンゾナフトチオフェン基;置換もしくは非置換のジメチルホスフィンオキシド基;置換もしくは非置換のジフェニルホスフィンオキシド;置換もしくは非置換のジナフチルホスフィンオキシド;置換もしくは非置換のベンズオキサゾリル基;置換もしくは非置換のベンゾチアゾリル基;置換もしくは非置換のベンズイミダゾリル基;置換もしくは非置換のトリフェニルシリル基;置換もしくは非置換のフェノチアジニル基;置換もしくは非置換のフェノキサジニル基;置換もしくは非置換のジフェニルアミン基;置換もしくは非置換のN−フェニルナフチルアミン基;置換もしくは非置換のN−フェニルビフェニルアミン基;置換もしくは非置換のN−フェニルフェナントレニルアミン基;置換もしくは非置換のN−ビフェニルナフチルアミン基;置換もしくは非置換のジビフェニルアミン基;置換もしくは非置換のN−ビフェニルフェナントレニルアミン基;置換もしくは非置換のジナフチルアミン基;置換もしくは非置換のN−クォーターフェニルフルオレニルアミン基;置換もしくは非置換のN−ターフェニルフルオレニルアミン基;置換もしくは非置換のN−ビフェニルターフェニルアミン基;置換もしくは非置換のN−ビフェニルフルオレニルアミン基;置換もしくは非置換のN−フェニルフルオレニルアミン基;置換もしくは非置換のN−ナフチルフルオレニルアミン基;置換もしくは非置換のN−フェナントレニルフルオレニルアミン基;置換もしくは非置換のジフルオレニルアミン基;置換もしくは非置換のN−フェニルターフェニルアミン基;置換もしくは非置換のN−フェニルカルバゾリルアミン基;置換もしくは非置換のN−ビフェニルカルバゾリルアミン基;置換もしくは非置換のN−フェニルベンゾカルバゾリルアミン基;置換もしくは非置換のN−ビフェニルベンゾカルバゾリルアミン基;置換もしくは非置換のN−フルオレニルカルバゾリルアミン基;置換もしくは非置換のベンゾカルバゾリル基;置換もしくは非置換のジベンゾカルバゾリル基;置換もしくは非置換のカルバゾリル基;置換もしくは非置換の
−−−−は、前記L1を介して化学式1に結合する部位であり、
[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ものである、
請求項1に記載のヘテロ環化合物。
ここで、「置換もしくは非置換の」という用語は、重水素;ハロゲン基;ニトリル基;アルキル基;シリル基;アミン基;ホスフィンオキシド基;アリール基;及びヘテロ環基からなる群より選択された1または2以上の置換基で置換されているか、前記例示された置換基のうちの2以上の置換基が連結された置換基で置換されているか、またはいずれの置換基も有しないことを意味する。 - 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1〜5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、正孔注入層または正孔輸送層を含み、
前記正孔注入層または正孔輸送層は、前記ヘテロ環化合物を含むものである、
請求項6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6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6に記載の有機発光素子。 - 前記有機物層は、正孔阻止層を含み、
前記正孔阻止層は、前記ヘテロ環化合物を含むものである、
請求項6に記載の有機発光素子。 - 前記有機物層は、電子輸送層、電子注入層、または電子輸送および電子注入を同時に行う層を含み、
前記電子輸送層、電子注入層、または電子輸送および電子注入を同時に行う層は、前記ヘテロ環化合物を含むものである、
請求項6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発光層の燐光ホストとして含むものである、
請求項6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、下記化学式1−Aで表される化合物を含むものである、
請求項6に記載の有機発光素子:
[化学式1−A]
n1は、1以上の整数であり、
Ar7は、置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L4は、直接結合;置換もしくは非置換のアリーレン基;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、
Ar8およびAr9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リール基;置換もしくは非置換のシリル基;置換もしくは非置換のゲルマニウム基;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アリールアルキル基;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、互いに結合して置換もしくは非置換の環を形成してもよいし、
n1が2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
ここで、「置換もしくは非置換の」という用語は、重水素;ハロゲン基;ニトリル基;ニトロ基;イミド基;アミド基;カルボニル基;エステル基;ヒドロキシ基;アルキル基;シクロアルキル基;アルコキシ基;アリールオキシ基;アルキルチオキシ基;アリールチオキシ基;アルキルスルホキシ基;アリールスルホキシ基;アルケニル基;シリル基;ホウ素基;アミン基;アリールホスフィン基;ホスフィンオキシド基;アリール基;及びヘテロ環基からなる群より選択された1または2以上の置換基で置換されているか、前記例示された置換基のうちの2以上の置換基が連結された置換基で置換されているか、またはいずれの置換基も有しないことを意味する。 - 前記L4は、直接結合であり、
Ar7は、2価のピレン基であり、
Ar8およびAr9は、互いに同一または異なり、それぞれ独立に、アルキル基で置換されたゲルマニウム基で置換もしくは非置換のアリール基であり、
n1は、2である、
請求項13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、下記化学式2−Aで表される化合物を含むものである、
請求項6に記載の有機発光素子:
[化学式2−A]
G11は、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、または下記化学式
G12は、フェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−ターフェニル−4−イル基、p−ターフェニル−3−イル基、p−ターフェニル−2−イル基、m−ターフェニル−4−イル基、m−ターフェニル−3−イル基、m−ターフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4"−t−ブチル−p−ターフェニル−4−イル基、または3−フルオランテニル基であり、
G13およびG14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ルコキシ基;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、
g12は、1〜5の整数であり、
g13およびg14はそれぞれ、1〜4の整数であり、
前記g12〜g14がそれぞれ2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
ここで、「置換もしくは非置換の」という用語は、水素;アルキル基;アルコキシ基;アリール基;及びヘテロアリール基からなる群より選択された1または2以上の置換基で置換されているか、前記例示された置換基のうちの2以上の置換基が連結された置換基で置換されているか、またはいずれの置換基も有しないことを意味する。 - 前記G11は、1−ナフチル基であり、
前記G12は、2−ナフチル基である、
請求項15に記載の有機発光素子。 - 前記発光層は、下記化学式2−Aで表される化合物を含むものである、
請求項13に記載の有機発光素子:
[化学式2−A]
G11は、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、または下記化学式
G12は、フェニル基、1−ナフチル基、2−ナフチル基、1−アントリル基、2−アントリル基、9−アントリル基、1−フェナントリル基、2−フェナントリル基、3−フェナントリル基、4−フェナントリル基、9−フェナントリル基、1−ナフタセニル基、2−ナフタセニル基、9−ナフタセニル基、1−ピレニル基、2−ピレニル基、4−ピレニル基、2−ビフェニリル基、3−ビフェニリル基、4−ビフェニリル基、p−ターフェニル−4−イル基、p−ターフェニル−3−イル基、p−ターフェニル−2−イル基、m−ターフェニル−4−イル基、m−ターフェニル−3−イル基、m−ターフェニル−2−イル基、o−トリル基、m−トリル基、p−トリル基、p−t−ブチルフェニル基、p−(2−フェニルプロピル)フェニル基、3−メチル−2−ナフチル基、4−メチル−1−ナフチル基、4−メチル−1−アントリル基、4'−メチルビフェニリル基、4"−t−ブチル−p−ターフェニル−4−イル基、または3−フルオランテニル基であり、
G13およびG14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ルコキシ基;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、
g12は、1〜5の整数であり、
g13およびg14はそれぞれ、1〜4の整数であり、
前記g12〜g14がそれぞれ2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
ここで、「置換もしくは非置換の」という用語は、水素;アルキル基;アルコキシ基;アリール基;及びヘテロアリール基からなる群より選択された1または2以上の置換基で置換されているか、前記例示された置換基のうちの2以上の置換基が連結された置換基で置換されているか、またはいずれの置換基も有しないことを意味する。
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JP2011222831A (ja) | 2010-04-12 | 2011-11-04 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
KR20120021203A (ko) | 2010-08-31 | 2012-03-08 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
WO2013069939A1 (ko) * | 2011-11-07 | 2013-05-16 | 덕산하이메탈(주) | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
KR102066437B1 (ko) | 2013-07-02 | 2020-01-15 | 덕산네오룩스 주식회사 | 광효율 개선층을 포함하는 유기전기소자 및 이를 포함하는 전자 장치 |
KR20150010016A (ko) * | 2013-07-17 | 2015-01-28 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
KR102188300B1 (ko) * | 2014-02-19 | 2020-12-08 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR102292572B1 (ko) * | 2014-11-07 | 2021-08-24 | 덕산네오룩스 주식회사 | 유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자 |
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- 2016-09-09 US US15/554,594 patent/US10421721B2/en active Active
- 2016-09-09 CN CN201680016504.XA patent/CN107406381B/zh active Active
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US9409404B2 (en) | 2013-03-22 | 2016-08-09 | Canon Finetech, Inc. | Liquid ejection head and liquid ejection apparatus |
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KR101844672B1 (ko) | 2018-04-03 |
JP2018509399A (ja) | 2018-04-05 |
CN107406381B (zh) | 2021-01-29 |
TW201718487A (zh) | 2017-06-01 |
TWI636043B (zh) | 2018-09-21 |
EP3351531A1 (en) | 2018-07-25 |
US20180037547A1 (en) | 2018-02-08 |
KR20170032170A (ko) | 2017-03-22 |
CN107406381A (zh) | 2017-11-28 |
EP3351531A4 (en) | 2019-05-08 |
US10421721B2 (en) | 2019-09-24 |
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