JP2013118368A - ジベンゾ[f,h]キノキサリン化合物、発光素子、発光装置、電子機器、及び照明装置 - Google Patents
ジベンゾ[f,h]キノキサリン化合物、発光素子、発光装置、電子機器、及び照明装置 Download PDFInfo
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- JP2013118368A JP2013118368A JP2012242332A JP2012242332A JP2013118368A JP 2013118368 A JP2013118368 A JP 2013118368A JP 2012242332 A JP2012242332 A JP 2012242332A JP 2012242332 A JP2012242332 A JP 2012242332A JP 2013118368 A JP2013118368 A JP 2013118368A
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- dibenzo
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- -1 Dibenzo[f,h]quinoxaline compound Chemical class 0.000 title claims abstract description 230
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 239000000126 substance Substances 0.000 claims abstract description 97
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical group C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000006267 biphenyl group Chemical group 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 42
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 239000011593 sulfur Substances 0.000 claims description 27
- 125000001624 naphthyl group Chemical group 0.000 claims description 21
- 125000005561 phenanthryl group Chemical group 0.000 claims description 21
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 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 17
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000005286 illumination Methods 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 75
- 125000005509 dibenzothiophenyl group Chemical group 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 187
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- 229910052757 nitrogen Inorganic materials 0.000 description 27
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 230000005281 excited state Effects 0.000 description 21
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- 238000006722 reduction reaction Methods 0.000 description 14
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 13
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 13
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 11
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
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- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
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- 150000004706 metal oxides Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 125000005595 acetylacetonate group Chemical group 0.000 description 7
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- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 7
- HEZMWWAKWCSUCB-PHDIDXHHSA-N (3R,4R)-3,4-dihydroxycyclohexa-1,5-diene-1-carboxylic acid Chemical compound O[C@@H]1C=CC(C(O)=O)=C[C@H]1O HEZMWWAKWCSUCB-PHDIDXHHSA-N 0.000 description 6
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002484 cyclic voltammetry Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 230000006798 recombination Effects 0.000 description 6
- 238000005215 recombination Methods 0.000 description 6
- 238000004544 sputter deposition Methods 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- FOGYVQKYNUUYRS-UHFFFAOYSA-N 3-(6-phenyldibenzothiophen-4-yl)phenanthro[9,10-b]pyrazine Chemical compound C1=CC=CC=C1C1=CC=CC2=C1SC1=C(C=3N=C4C5=CC=CC=C5C5=CC=CC=C5C4=NC=3)C=CC=C12 FOGYVQKYNUUYRS-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
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- 238000000295 emission spectrum Methods 0.000 description 5
- 230000005283 ground state Effects 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
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- 239000010453 quartz Substances 0.000 description 5
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- 229910001930 tungsten oxide Inorganic materials 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 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 4
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
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- 238000004528 spin coating Methods 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
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- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical group C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- UOCMXZLNHQBBOS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2o1.Oc1ccccc1-c1nc2ccccc2o1 UOCMXZLNHQBBOS-UHFFFAOYSA-N 0.000 description 2
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 2
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- FEYJCWNQZBKYKT-UHFFFAOYSA-N 3-chlorophenanthro[9,10-b]pyrazine Chemical compound C1=CC=C2C3=NC(Cl)=CN=C3C3=CC=CC=C3C2=C1 FEYJCWNQZBKYKT-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 2
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 2
- UQVFZEYHQJJGPD-UHFFFAOYSA-N 9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UQVFZEYHQJJGPD-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group 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 2
- SXGIRTCIFPJUEQ-UHFFFAOYSA-N 9-anthracen-9-ylanthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C(C=3C4=CC=CC=C4C=C4C=CC=CC4=3)=C21 SXGIRTCIFPJUEQ-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 238000001420 photoelectron spectroscopy Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 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
Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
【解決手段】単数もしくは複数のジベンゾチオフェニル基又はジベンゾフラニル基がジベンゾ[f,h]キノキサリン骨格に直接結合した化合物を提供する。
【選択図】なし
Description
本実施の形態では、本発明の一態様のジベンゾ[f,h]キノキサリン化合物について説明する。本発明の一態様は、単数もしくは複数のジベンゾチオフェン−4−イル基又はジベンゾフラン−4−イル基がジベンゾ[f,h]キノキサリン骨格に直接結合した化合物である。
合成スキーム(A−1)に示すように、ハロゲン化ジベンゾキノキサリン化合物(a1)とジベンゾチオフェン−4−ホウ素化合物又はジベンゾフラン−4−ホウ素化合物(a2)とをカップリングさせることで、上記一般式(G1)で表されるジベンゾ[f,h]キノキサリン化合物を合成することができる。合成スキーム(A−1)を以下に示す。
本実施の形態では実施の形態1で説明したジベンゾ[f,h]キノキサリン化合物を用いた発光素子の詳細な構造の例について図1(A)を用いて以下に説明する。
本実施の形態は、複数の発光ユニットを積層した構成の発光素子(以下、積層型素子ともいう)の態様について、図1(B)を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する発光素子である。発光ユニットとしては、実施の形態2で示したEL層103と同様な構成を用いることができる。つまり、実施の形態2で示した発光素子は、1つの発光ユニットを有する発光素子であり、本実施の形態では、複数の発光ユニットを有する発光素子ということができる。
本実施の形態では、実施の形態1に記載のジベンゾ[f,h]キノキサリン化合物を含む発光素子(すなわち、実施の形態2又は実施の形態3に記載の発光素子)を用いた発光装置について説明する。
本実施の形態では、実施の形態1に記載のジベンゾ[f,h]キノキサリン化合物を用いた発光素子を照明装置として用いる例を図4を参照しながら説明する。図4(B)は照明装置の上面図、図4(A)は図4(B)におけるE−F断面図である。
本実施の形態では、実施の形態1に記載のジベンゾ[f,h]キノキサリン化合物を含む発光素子をその一部に含む電子機器の例について説明する。実施の形態1に記載のジベンゾ[f,h]キノキサリン化合物を含む発光素子は発光効率が良好であり、消費電力が低減された発光素子である。その結果、本実施の形態に記載の電子機器は、消費電力が低減された発光部を有する電子機器とすることが可能である。また、実施の形態1に記載のジベンゾ[f,h]キノキサリン化合物を含む発光素子は、駆動電圧の小さい発光素子であるため、駆動電圧の小さい電子機器とすることが可能である。また、実施の形態1に記載のジベンゾ[f,h]キノキサリン化合物を含む発光素子は寿命の長い発光素子であるため、本実施の形態に記載の電子機器は信頼性の高い電子機器とすることが可能である。
本実施例では、実施の形態1に構造式(101)として記載のジベンゾ[f,h]キノキサリン化合物である2−(6−フェニルジベンゾチオフェン−4−イル)ジベンゾ[f,h]キノキサリン(略称:2DBTDBq−IV)の合成方法について説明する。2DBTDBq−IVの構造式を以下に示す。
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極101は、発光素子の陽極として機能する電極である。
102 第2の電極
103 EL層
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
400 基板
401 第1の電極
402 補助電極
403 EL層
404 第2の電極
405 シール材
406 シール材
407 封止基板
408 空間
412 パッド
420 ICチップ
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 駆動回路部(ソース線駆動回路)
602 画素部
603 駆動回路部(ゲート線駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
623 nチャネル型TFT
624 pチャネル型TFT
901 筐体
902 液晶層
903 バックライトユニット
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
2001 筐体
2002 光源
3001 照明装置
5000 表示
5001 表示
5002 表示
5003 表示
5004 表示
5005 表示
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
7400 携帯電話機
9033 留め具
9034 スイッチ
9035 電源スイッチ
9036 スイッチ
9037 操作キー
9038 操作スイッチ
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a タッチパネル領域
9632b タッチパネル領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9638 コンバータ
9639 ボタン
Claims (23)
- ジベンゾ[f,h]キノキサリン骨格とジベンゾチオフェン骨格又はジベンゾフラン骨格が直接結合したジベンゾ[f,h]キノキサリン化合物を含む発光素子。
- ジベンゾ[f,h]キノキサリン骨格に置換又は無置換のジベンゾチオフェン−4−イル基または置換又は無置換のジベンゾフラン−4−イル基が直接結合したジベンゾ[f,h]キノキサリン化合物を含む発光素子。
- 下記一般式(G1)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R1乃至R10のいずれか一は置換又は無置換のジベンゾチオフェン−4−イル基または置換又は無置換のジベンゾフラン−4−イル基であり、他の基はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基、置換又は無置換のジベンゾチオフェン−4−イル基及び置換又は無置換のジベンゾフラン−4−イル基のいずれかである。) - 下記一般式(G1)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R1乃至R10のいずれか一は下記一般式(G1−1)で表される基であり、他の基はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基及び下記一般式(G1−2)で表される基のいずれかである。)
(一般式(G1−1)中、E1は硫黄又は酸素を表し、R11乃至R17はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。また一般式(G1−2)中、E2は硫黄又は酸素を表し、R21乃至R27はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。) - 下記一般式(G2)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R1、R2、R4、R5、R8及びR9のうちいずれか一は置換又は無置換のジベンゾチオフェン−4−イル基または置換又は無置換のジベンゾフラン−4−イル基であり、他の基はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基、置換又は無置換のジベンゾチオフェン−4−イル基及び置換又は無置換のジベンゾフラン−4−イル基のいずれかである。) - 下記一般式(G2)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R1、R2、R4、R5、R8及びR9のうちいずれか一は下記一般式(G1−1)で表される基であり、他の基はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基及び下記一般式(G1−2)で表される基のいずれかである。)
(一般式(G1−1)中、E1は硫黄又は酸素を表し、R11乃至R17はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。また一般式(G1−2)中、E2は硫黄又は酸素を表し、R21乃至R27はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。) - 下記一般式(G3)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R4及びR9のうち一方は置換又は無置換のジベンゾチオフェン−4−イル基または置換又は無置換のジベンゾフラン−4−イル基であり、他方は水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基、置換又は無置換のジベンゾチオフェン−4−イル基及び置換又は無置換のジベンゾフラン−4−イル基のいずれかである。) - 下記一般式(G3)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中、R4及びR9のうち一方は下記一般式(G1−1)で表される基であり、他方は水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基及び下記一般式(G1−2)で表される基のいずれかである。)
(一般式(G1−1)中、E1は硫黄又は酸素を表し、R11乃至R17はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。また一般式(G1−2)中、E2は硫黄又は酸素を表し、R21乃至R27はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。) - 下記一般式(G4)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R5及びR8の一方は置換又は無置換のジベンゾチオフェン−4−イル基または置換又は無置換のジベンゾフラン−4−イル基であり、他方は水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基、置換又は無置換のジベンゾチオフェン−4−イル基及び置換又は無置換のジベンゾフラン−4−イル基のいずれかである。) - 下記一般式(G4)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R5及びR8の一方は下記一般式(G1−1)で表される基であり、他方は水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基、置換又は無置換のビフェニル基、置換又は無置換のナフチル基、置換又は無置換のフェナントリル基、置換又は無置換のトリフェニレニル基及び下記一般式(G1−2)で表される基のいずれかである。)
(一般式(G1−1)中、E1は硫黄又は酸素を表し、R11乃至R17はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。また一般式(G1−2)中、E2は硫黄又は酸素を表し、R21乃至R27はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。) - 下記一般式(G5)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R2は置換又は無置換のジベンゾチオフェン−4−イル基または置換又は無置換のジベンゾフラン−4−イル基を表す。) - 下記一般式(G5)で表されるジベンゾ[f,h]キノキサリン化合物。
(但し、式中R2は下記一般式(G1−1)で表される基である。)
(一般式(G1−1)中、E1は硫黄又は酸素を表し、R11乃至R17はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。) - 請求項4、請求項6及び請求項8のいずれか一項において、前記一般式(G1−1)で表される基が下記一般式(G2−1)で表される基であり、前記一般式(G1−2)で表される基が下記一般式(G2−2)で表される基であるジベンゾ[f,h]キノキサリン化合物。
(但し式(G2−1)中、E1は硫黄又は酸素を表し、R11、R13及びR16はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。また一般式(G2−2)中、E2は硫黄又は酸素を表し、R21、R23及びR26はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。) - 請求項10において、前記一般式(G1−1)で表される基が下記一般式(G2−1)で表される基であるジベンゾ[f,h]キノキサリン化合物。
(但し、式中E1は硫黄又は酸素を表し、R11、R13及びR16はそれぞれ独立に水素、炭素数1〜6のアルキル基、置換又は無置換のフェニル基及び置換又は無置換のビフェニル基のいずれかを表す。) - 下記構造式(100)で表されるジベンゾ[f,h]キノキサリン化合物。
- 請求項3乃至請求項15のいずれか一項に記載のジベンゾ[f,h]キノキサリン化合物を含む発光素子。
- 陽極及び陰極間に発光層を有する発光素子において、
前記発光層が、発光物質と、請求項3乃至請求項15のいずれか一項に記載のジベンゾ[f,h]キノキサリン化合物とを含む発光素子。 - 陽極及び陰極間に発光層を有する発光素子において、
前記発光層が、発光物質と、電子輸送性化合物と、正孔輸送性化合物と、を含み、
前記電子輸送性化合物は、請求項3乃至請求項15のいずれか一項に記載のジベンゾ[f,h]キノキサリン化合物であり、
前記正孔輸送性化合物は、前記電子輸送性化合物よりも正孔輸送性が高く、カルバゾール骨格、トリアリールアミン骨格、ジベンゾチオフェン骨格、又はジベンゾフラン骨格を有する発光素子。 - 請求項18において、前記発光層の前記陽極側に接する層が前記発光層に含まれる前記正孔輸送性化合物を含む発光素子。
- 請求項18又は請求項19において、前記発光層の前記陰極側に接する層が前記ジベンゾ[f,h]キノキサリン化合物を含む発光素子。
- 請求項17乃至請求項20に記載の発光素子を発光部に備える発光装置。
- 請求項21に記載の発光装置を表示部に備える電子機器。
- 請求項21に記載の発光装置を発光部に備える照明装置。
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JP6109530B2 (ja) | 2017-04-05 |
JP2017139474A (ja) | 2017-08-10 |
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