JP7038422B2 - 多環芳香族誘導体化合物及びこれを用いた有機発光素子 - Google Patents
多環芳香族誘導体化合物及びこれを用いた有機発光素子 Download PDFInfo
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- JP7038422B2 JP7038422B2 JP2019217554A JP2019217554A JP7038422B2 JP 7038422 B2 JP7038422 B2 JP 7038422B2 JP 2019217554 A JP2019217554 A JP 2019217554A JP 2019217554 A JP2019217554 A JP 2019217554A JP 7038422 B2 JP7038422 B2 JP 7038422B2
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 204
- 239000000126 substance Substances 0.000 claims description 115
- 239000010410 layer Substances 0.000 claims description 78
- -1 R 42 Chemical compound 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 230000000903 blocking effect Effects 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000005264 aryl amine group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 13
- 150000001721 carbon Chemical class 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 2
- 150000001454 anthracenes Chemical class 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 151
- 238000003786 synthesis reaction Methods 0.000 description 151
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000000203 mixture Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000003367 polycyclic group Chemical group 0.000 description 12
- 230000002194 synthesizing effect Effects 0.000 description 12
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 7
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 7
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- 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 4
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 4
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C(*)*1c2c(C)nnnc2*C(c2nnnnc2C)=C1*)c1c(C)nnnn1 Chemical compound CC(C(*)*1c2c(C)nnnc2*C(c2nnnnc2C)=C1*)c1c(C)nnnn1 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 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 2
- 150000003852 triazoles Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- PRRIGGBFRPGBRY-UHFFFAOYSA-N (3-diphenylphosphanyl-1-naphthalen-1-ylnaphthalen-2-yl)-diphenylphosphane Chemical group C1=CC=CC=C1P(C=1C(=C(C=2C3=CC=CC=C3C=CC=2)C2=CC=CC=C2C=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 PRRIGGBFRPGBRY-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZPXDNSYFDIHPOJ-UHFFFAOYSA-N 1,5-dichloro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C=C1Cl ZPXDNSYFDIHPOJ-UHFFFAOYSA-N 0.000 description 1
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- 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
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 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
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003248 quinolines Chemical class 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
- 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000005507 spraying 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 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
- 239000011787 zinc oxide Substances 0.000 description 1
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Description
Q1~Q3は、互いに同一又は異なっており、それぞれ独立して、置換もしくは非置換の炭素数6~50の芳香族炭化水素環である、または置換もしくは非置換の炭素数2~50のヘテロ芳香環である。
各Zは、それぞれ独立してCRまたはNであり、置換基Rは互いに同一又は異なっており、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数5~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数5~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数5~30のアリールシリル基、ニトロ基、シアノ基、及びハロゲン基から選択されるいずれか1つである。
また、前記「置換もしくは非置換の炭素数1~10のアルキル基」、「置換もしくは非置換の炭素数6~30のアリール基」などにおいての前記アルキル基またはアリール基の炭素数は、前記置換基が置換された部分を考慮せずに非置換のものと見なしたときのアルキル部分またはアリール部分を構成する全炭素数を意味する。例えば、パラ位にブチル基が置換されたフェニル基は、炭素数4のブチル基で置換された炭素数6のアリール基に該当することを意味する。
Claims (15)
- 下記化学式A-3、A-4、A-5または化学式A-6で表される有機発光化合物であって、
前記R1~R3は、互いに同一又は異なっており、それぞれ独立して、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数5~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数5~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数5~30のアリールシリル基、ニトロ基、シアノ基、及びハロゲン基から選択されるいずれか1つであり、
Zは、CRまたはNであり、置換基Rは、互いに同一又は異なっており、それぞれ独立して、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数5~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数5~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数5~30のアリールシリル基、ニトロ基、シアノ基、及びハロゲン基から選択されるいずれか1つである有機発光化合物。 - 第1電極、前記第1電極に対向する第2電極、及び前記第1電極と第2電極との間に介在する1層以上の有機層を含み、
前記有機層の少なくとも1層が、請求項1に記載の化学式A-3、化学式A-4、化学式A-5または化学式A-6で表される化合物を1種以上含む、有機発光素子。 - 前記有機層は、電子注入層、電子輸送層、正孔注入層、正孔輸送層、電子阻止層、正孔阻止層及び発光層のうちの1層以上を含む有機発光素子であって、
前記有機層のうちの少なくとも1層が、化学式A-3、化学式A-4、化学式A-5または化学式A-6で表される有機発光化合物を含むことを特徴とする、請求項3に記載の有機発光素子。 - 前記発光層は、下記化学式Cで表されるアントラセン誘導体をホスト化合物として含むことを特徴とする、請求項4に記載の有機発光素子であって、
R21~R28は、それぞれ、同一又は異なっており、前記請求項1に記載の化学式A-3、化学式A-4、化学式A-5または化学式A-6のR1~R4で定義されたものと同一であり、
Ar9及びAr10は、それぞれ、互いに同一又は異なっており、互いに独立して、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~20のアルキニル基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数5~30のシクロアルケニル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数2~30のヘテロシクロアルキル基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数6~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数6~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、及び置換もしくは非置換の炭素数6~30のアリールシリル基から選択されるいずれか1つであり、
L13は、単結合であるか、または置換もしくは非置換の炭素数6~20のアリーレン基、または置換もしくは非置換の炭素数2~20のヘテロアリーレン基から選択されるいずれか1つであり、
kは、1~3の整数であり、前記kが2以上である場合に、それぞれのL13は互いに同一又は異なっている有機発光素子。 - 前記化学式CのL13は、単結合であるか、または置換もしくは非置換の炭素数6~20のアリーレン基であることを特徴とする、請求項5に記載の有機発光素子。
- 前記正孔輸送層及び電子阻止層は、それぞれ、下記化学式Dで表される化合物を含むことを特徴とする、請求項4に記載の有機発光素子であって、
R41~R43は、互いに同一又は異なっており、それぞれ独立して、水素、重水素、置換もしくは非置換の炭素数1~20のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数7~50のアリールアルキル基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数6~30のアリールシリル基、及びハロゲン基から選択されるいずれか1つであり、
L31~L34は、互いに同一又は異なっており、それぞれ独立して、単結合、置換もしくは非置換の炭素数6~50のアリーレン基、及び置換もしくは非置換の炭素数2~50のヘテロアリーレン基から選択されるいずれか1つであり、
Ar31~Ar34は、互いに同一又は異なっており、それぞれ独立して、置換もしくは非置換の炭素数6~50のアリール基、及び置換もしくは非置換の炭素数2~50のヘテロアリール基から選択されるいずれか1つであり、
nは、0~4の整数であり、nが2以上である場合に、R43を含むそれぞれの芳香族環は互いに同一又は異なっており、
m1~m3は、0~4の整数であり、m1およびm3がそれぞれ2以上である場合に、それぞれのR41、R42、またはR43は互いに同一又は異なっており、
R41~R43が結合されていない芳香族環の炭素原子は、水素または重水素と結合する有機発光素子。 - 前記Ar31~Ar34のうちの少なくとも1つは、下記化学式Eで表される置換基であることを特徴とする、請求項9に記載の有機発光素子であって、
R51~R54は、互いに同一又は異なっており、それぞれ独立して、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~20のアルキニル基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数5~30のシクロアルケニル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数2~30のヘテロシクロアルキル基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数5~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数5~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数5~30のアリールシリル基、ニトロ基、シアノ基、及びハロゲン基から選択されるいずれか1つであり、これらはそれぞれ互いに結合して環を形成することができ、
Yは、炭素原子または窒素原子であり、Zは、炭素原子、酸素原子、硫黄原子または窒素原子であり、
Ar35~Ar37は、互いに同一又は異なっており、それぞれ独立して、置換もしくは非置換の炭素数5~50のアリール基、及び置換もしくは非置換の炭素数3~50のヘテロアリール基から選択されるいずれか1つであり、
Zが酸素原子または硫黄原子である場合、Ar37は存在せず、Y及びZが窒素原子である場合、Ar35、Ar36及びAr37のいずれか1つのみが存在し、Yが窒素原子及びZが炭素原子である場合、Ar36は存在せず、
ただし、R51~R54及びAr35~Ar37のうち1つは、前記化学式Dでの連結基L31~L34のうちの1つと結合した単結合である有機発光素子。 - 前記正孔輸送層及び電子阻止層は、それぞれ、下記化学式Fで表される化合物を含むことを特徴とする、請求項4に記載の有機発光素子であって、
R61~R63は、互いに同一又は異なっており、それぞれ独立して、水素、重水素、置換もしくは非置換の炭素数1~30のアルキル基、置換もしくは非置換の炭素数6~50のアリール基、置換もしくは非置換の炭素数2~30のアルケニル基、置換もしくは非置換の炭素数2~20のアルキニル基、置換もしくは非置換の炭素数3~30のシクロアルキル基、置換もしくは非置換の炭素数5~30のシクロアルケニル基、置換もしくは非置換の炭素数2~50のヘテロアリール基、置換もしくは非置換の炭素数2~30のヘテロシクロアルキル基、置換もしくは非置換の炭素数1~30のアルコキシ基、置換もしくは非置換の炭素数6~30のアリールオキシ基、置換もしくは非置換の炭素数1~30のアルキルチオキシ基、置換もしくは非置換の炭素数6~30のアリールチオキシ基、置換もしくは非置換の炭素数1~30のアルキルアミン基、置換もしくは非置換の炭素数6~30のアリールアミン基、置換もしくは非置換の炭素数1~30のアルキルシリル基、置換もしくは非置換の炭素数6~30のアリールシリル基、置換もしくは非置換の炭素数1~30のアルキルゲルマニウム基、置換もしくは非置換の炭素数1~30のアリールゲルマニウム基、シアノ基、ニトロ基、及びハロゲン基から選択されるいずれか1つであり、
Ar51~Ar54は、互いに同一又は異なっており、それぞれ独立して、置換もしくは非置換の炭素数6~40のアリール基、または置換もしくは非置換の炭素数2~30のヘテロアリール基である有機発光素子。 - 前記有機発光素子は、平板ディスプレイ装置、フレキシブルディスプレイ装置、単色又は白色の平板照明装置(照明システム)及び単色又は白色のフレキシブル照明装置から選択されるいずれか1つに使用されることを特徴とする、請求項3に記載の有機発光素子。
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