JP2012131775A - カルバゾール化合物、発光素子用材料、有機半導体材料、発光素子、発光装置、照明装置及び電子機器 - Google Patents
カルバゾール化合物、発光素子用材料、有機半導体材料、発光素子、発光装置、照明装置及び電子機器 Download PDFInfo
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- JP2012131775A JP2012131775A JP2011255625A JP2011255625A JP2012131775A JP 2012131775 A JP2012131775 A JP 2012131775A JP 2011255625 A JP2011255625 A JP 2011255625A JP 2011255625 A JP2011255625 A JP 2011255625A JP 2012131775 A JP2012131775 A JP 2012131775A
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- carbazole compound
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- -1 Carbazole compound Chemical class 0.000 title claims abstract description 146
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 239000000463 material Substances 0.000 title claims abstract description 112
- 239000004065 semiconductor Substances 0.000 title claims abstract description 16
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 150000002894 organic compounds Chemical class 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004434 sulfur atom Chemical group 0.000 claims description 21
- 125000003944 tolyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 13
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 24
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 10
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 8
- 239000010410 layer Substances 0.000 description 188
- 239000000126 substance Substances 0.000 description 108
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 239000000758 substrate Substances 0.000 description 40
- 239000000203 mixture Substances 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- 239000010408 film Substances 0.000 description 23
- 230000005284 excitation Effects 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 21
- 238000002347 injection Methods 0.000 description 21
- 239000007924 injection Substances 0.000 description 21
- 238000005259 measurement Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000000862 absorption spectrum Methods 0.000 description 20
- 238000007254 oxidation reaction Methods 0.000 description 20
- 239000002131 composite material Substances 0.000 description 19
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
- 238000006722 reduction reaction Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- 150000001716 carbazoles Chemical class 0.000 description 16
- 230000006870 function Effects 0.000 description 16
- 150000002431 hydrogen Chemical class 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 238000002484 cyclic voltammetry Methods 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 14
- 239000010409 thin film Substances 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000005281 excited state Effects 0.000 description 12
- 230000002349 favourable effect Effects 0.000 description 12
- 238000005381 potential energy Methods 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 11
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- NSABRUJKERBGOU-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 NSABRUJKERBGOU-UHFFFAOYSA-N 0.000 description 9
- 239000010453 quartz Substances 0.000 description 9
- 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
- 238000007740 vapor deposition Methods 0.000 description 9
- 238000000295 emission spectrum Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 238000000859 sublimation Methods 0.000 description 8
- 230000008022 sublimation Effects 0.000 description 8
- 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 7
- 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 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 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 6
- 238000000746 purification Methods 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 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
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 230000000295 complement effect Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 5
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000011787 zinc oxide Substances 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
- TXLRAQXGAKHLAO-UHFFFAOYSA-N 3-dibenzofuran-4-yl-9h-carbazole Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2C1=CC=C2NC3=CC=CC=C3C2=C1 TXLRAQXGAKHLAO-UHFFFAOYSA-N 0.000 description 4
- SDNQERUOELVIOF-UHFFFAOYSA-N 3-dibenzothiophen-4-yl-9h-carbazole Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2C1=CC=C2NC3=CC=CC=C3C2=C1 SDNQERUOELVIOF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 150000001556 benzimidazoles Chemical class 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
- 239000004305 biphenyl Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
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- 230000005283 ground state Effects 0.000 description 4
- 238000010438 heat treatment Methods 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
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 3
- 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 3
- CXDSUNAXNRKTQI-UHFFFAOYSA-N 3-dibenzofuran-4-yl-9-[4-(1-phenylbenzimidazol-2-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(N2C3=CC=C(C=C3C3=CC=CC=C32)C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=C1 CXDSUNAXNRKTQI-UHFFFAOYSA-N 0.000 description 3
- OOKRYIPMHLUQHU-UHFFFAOYSA-N 9-(4-bromophenyl)-9-phenylfluorene Chemical compound C1=CC(Br)=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 OOKRYIPMHLUQHU-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 125000005595 acetylacetonate group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
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- 235000010290 biphenyl Nutrition 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
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052760 oxygen Chemical group 0.000 description 3
- 239000001301 oxygen Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- 238000001308 synthesis method Methods 0.000 description 3
- 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 3
- 238000001771 vacuum deposition Methods 0.000 description 3
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- 239000003981 vehicle Substances 0.000 description 3
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- XAWQWMLNBYNXJX-UHFFFAOYSA-N n,n-diphenyl-9-[4-(10-phenylanthracen-9-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C(C=4C=CC=CC=4)=C4C=CC=CC4=3)C2=CC=1)C1=CC=CC=C1 XAWQWMLNBYNXJX-UHFFFAOYSA-N 0.000 description 1
- CRWAGLGPZJUQQK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-4-[2-[4-(n-(4-carbazol-9-ylphenyl)anilino)phenyl]ethenyl]-n-phenylaniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 CRWAGLGPZJUQQK-UHFFFAOYSA-N 0.000 description 1
- DKQKUOFOSZLDGL-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-n-phenyl-9,10-bis(2-phenylphenyl)anthracen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 DKQKUOFOSZLDGL-UHFFFAOYSA-N 0.000 description 1
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- RVHDEFQSXAYURV-UHFFFAOYSA-N n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)C=C1 RVHDEFQSXAYURV-UHFFFAOYSA-N 0.000 description 1
- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 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
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 235000009566 rice Nutrition 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
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- 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
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 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
- 150000003752 zinc compounds Chemical class 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 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
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Abstract
【解決手段】ジベンゾフラン骨格もしくはジベンゾチオフェン骨格の4位がカルバゾール骨格の3位に結合したカルバゾール基の窒素が、ベンゾイミダゾール骨格にフェニレン基を介して結合したカルバゾール化合物を提供する。当該カルバゾール化合物は良好なキャリア輸送性を有し、発光素子の材料や有機半導体材料として好適に用いることが出来る。
【選択図】なし
Description
本実施の形態におけるカルバゾール化合物は、ジベンゾフラン骨格もしくはジベンゾチオフェン骨格の4位がカルバゾール骨格の3位に結合したカルバゾール基の窒素が、ベンゾイミダゾール骨格にフェニレン基を介して結合した構造を有する。なお、ベンゾイミダゾール骨格は、1位の窒素が炭素数6乃至12のアリール基を有することとする。
続いて、本実施の形態では、下記一般式(G1)で表されるカルバゾール化合物の合成方法について説明する。カルバゾール化合物の合成方法としては種々の反応を適用することができる。例えば、以下に示す合成反応を行うことによって、一般式(G1)で表されるカルバゾール化合物を合成することができる。
本実施の形態では、実施の形態1に記載のカルバゾール化合物を有機半導体素子の一種である縦型トランジスタ(静電誘導トランジスタ:SIT)の活性層として用いる形態を例示する。
本実施の形態では実施の形態1に示したカルバゾール化合物を用いた発光素子の一態様について図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4で示した有機化合物を含む層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4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に記載のカルバゾール化合物を含む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4又は実施の形態5に示す発光素子をその一部に含む電子機器について説明する。実施の形態4又は実施の形態5に記載の発光素子は、実施の形態1に記載のカルバゾール化合物を含むことから、消費電力が低減された発光素子であり、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表示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4又は実施の形態5に記載の発光素子は、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。
本実施例では一般式(G1)で表されるカルバゾール誘導体である、2−[4−{3−(ジベンゾチオフェン−4−イル)−9H−カルバゾール−9−イル}フェニル]−1−フェニルベンゾイミダゾール(略称:DBTCzBIm−II)の合成方法について説明する。DBTCzBIm−IIの構造を下記構造式(100)に示す。
3.0g(12mmol)の3−ブロモカルバゾールと、2.8g(12mmol)のジベンゾチオフェン−4−ボロン酸と、150mg(0.5mol)のトリ(オルト−トリル)ホスフィンを、200mL三つ口フラスコへ入れ、フラスコ内を窒素置換した。この混合物へ40mLのトルエンと、40mLのエタノールと、15mL(2.0mol/L)の炭酸カリウム水溶液を加えた。フラスコ内を減圧下で攪拌することにより、混合物を脱気した。脱気後窒素置換し、この混合物へ、23mg(0.10mmol)の酢酸パラジウム(II)を加えてから、110℃で3時間還流した。還流後、混合物を室温までさましてから、得られた固体を吸引ろ過により回収した。回収した個体を100mLのトルエンに溶かし、この溶液をセライト(和光純薬工業株式会社、カタログ番号:531−16855)、フロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、アルミナを通してろ過した。得られたろ液を濃縮して得た固体を、トルエン/ヘキサンにより再結晶したところ白色固体を1.4g、収率32%で得た。ステップ1の合成スキームを(a−1)に示す。
0.36g(1.0mmol)のN−フェニル−2−(4−ブロモフェニル)ベンゾイミダゾールと、0.36g(1.0mmol)の3−(ジベンゾチオフェン−4−イル)−9H−カルバゾールを100mLの三口フラスコへ入れ、フラスコ内を窒素置換した。この混合物へ、10mLのトルエンと、0.10mLのトリ(tert−ブチル)ホスフィン(10wt%ヘキサン溶液)と、0.15g(4.3mmol)のナトリウム tert−ブトキシドを加えた。この混合物を、減圧下で攪拌しながら脱気した。この混合物を80℃に加熱してから、5.0mg(0.025mmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加え更に、80℃で3時間攪拌した。撹拌後、この混合物へ14mg(0.025mmol)のビス(ジベンジリデンアセトン)パラジウム(0)を追加してから、更に110℃で7.5時間撹拌した。撹拌後、混合物へ約30mLのトルエンを加えてから80℃で撹拌しこの混合物を、セライト(和光純薬工業株式会社、カタログ番号:531−16855)、フロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、アルミナを通して酢酸エチルを用いて熱ろ過した。得られたろ液を濃縮し、白色固体を得た。得られた個体を、トルエンに溶かし、シリカゲルカラムクロマドグラフィー(展開溶媒、ヘキサン:酢酸エチル=4:1)により精製し、さらにトルエン/ヘキサンを用いて再結晶しところ、白色個体を0.41g、収率65%で得た。ステップ2の合成スキームを(b−1)に示す。
本実施例では実施の形態1に示したカルバゾール誘導体である、2−[4−{3−(ジベンゾフラン−4−イル)−9H−カルバゾール−9−イル}フェニル]−1−フェニルベンゾイミダゾール(略称:DBFCzBIm−II)の合成方法について説明する。DBFCzBIm−IIの構造を下記構造式(200)に示す。
2.0g(8.1mmol)の3−ブロモカルバゾールと、1.7g(8.1mmol)のジベンゾフラン−4−ボロン酸と、150mg(0.5mol)のトリ(オルト−トリル)ホスフィンを、200mL三つ口フラスコへ入れ、フラスコ内を窒素置換した。この混合物へ20mLのトルエンと20mLのエタノールと、15mL(0.2mol)の炭酸カリウム水溶液(2.0mol/L)を加えた。フラスコ内を減圧下で攪拌することにより、混合物を脱気した。この混合物へ、23mg(0.10mmol)の酢酸パラジウム(II)を加えてから、80℃で還流した。還流後、混合物を室温までさましてから、得られた固体を吸引ろ過により回収した。回収した個体を100mLのトルエンに溶かし、この溶液をセライト(和光純薬工業株式会社、カタログ番号:531−16855)、フロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、アルミナを通してろ過した。得られたろ液を濃縮して得た固体を、トルエン/ヘキサンにより再結晶したところ白色固体を2.3g、収率85%で得た。ステップ1の合成スキームを(a−2)に示す。
0.70g(1.0mmol)の2−(4−ブロモフェニル)−3−フェニルベンゾイミダゾールと、0.67g(1.0mmol)の4−(9H−カルバゾール−3−イル)ジベンゾフランを100mLの三口フラスコへ入れ、フラスコ内を窒素置換した。この混合物へ、15mLのトルエンと、0.10mLのトリ(tert−ブチル)ホスフィン(10wt%ヘキサン溶液)と、0.48g(4.3mmol)のナトリウム tert−ブトキシドを加えた。この混合物を、減圧下で攪拌しながら脱気した。この混合物を110℃で20時間攪拌した。撹拌後、混合物を約30mLの水で2回洗浄し、有機層と水層を分離した後、水層を約30mLのトルエンで2回抽出した。有機層と抽出溶液を合わせて、約100mLの飽和食塩水で1回洗浄した。得られた有機層を硫酸マグネシウムにより乾燥し、この混合物をセライト(和光純薬工業株式会社、カタログ番号:531−16855)、フロリジール(和光純薬工業株式会社、カタログ番号:540−00135)、アルミナを通してろ過した。得られたろ液を濃縮し、褐色固体を得た。得られた褐色個体をシリカゲルカラムクロマトグラフィー(展開溶媒は酢酸エチル:トルエン=5:95)により精製し、さらにヘキサン/トルエンにより再結晶したところ、淡褐色個体を0.86g、収率71%で得た。ステップ2の合成スキームを(b−2)に示す。
まず、第1の電極102として110nmの膜厚でケイ素を含むインジウム錫酸化物(ITSO)が成膜されたガラス基板101を用意した。発光領域が2mm×2mmとなるように、ITSO表面は、2mm角の大きさで表面が露出するよう周辺をポリイミド膜で覆った。この基板上に発光素子を形成するための前処理として、基板表面を水で洗浄し、200℃で1時間焼成した後、UVオゾン処理を370秒行った。その後、10−4Pa程度まで内部が減圧された真空蒸着装置に基板を導入し、真空蒸着装置内の加熱室において170℃で30分間の真空焼成を行った後、基板を30分程度放冷した。
以上により得られた発光素子1及び発光素子2を、窒素雰囲気のグローブボックス内において、発光素子が大気に曝されないように封止する作業を行った後、これらの発光素子の動作特性について測定を行った。なお、測定は室温(25℃に保たれた雰囲気)で行った。
上記実施例で用いた4−フェニル−4’−(9−フェニルフルオレン−9−イル)トリフェニルアミン(略称:BPAFLP)(構造式(i))の合成方法について具体的に説明する。BPAFLPの構造を以下に示す。
100mL三口フラスコにて、マグネシウムを1.2g(50mmol)減圧下で30分加熱撹拌し、マグネシウムを活性化させた。これを室温に冷まして窒素雰囲気にした後、ジブロモエタン数滴を加えて発泡、発熱するのを確認した。ここにジエチルエーテル10mL中に溶かした2−ブロモビフェニル12g(50mmol)をゆっくり滴下した後、2.5時間加熱還流撹拌してグリニヤール試薬とした。
100mL三口フラスコへ、9−(4−ブロモフェニル)−9−フェニルフルオレンを3.2g(8.0mmol)、4−フェニル−ジフェニルアミンを2.0g(8.0mmol)、ナトリウム tert−ブトキシドを1.0g(10mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)を23mg(0.04mmol)加え、フラスコ内の雰囲気を窒素置換した。この混合物へ、脱水キシレン20mLを加えた。この混合物を、減圧下で攪拌しながら脱気した後、トリ(tert−ブチル)ホスフィン(10wt%ヘキサン溶液)0.2mL(0.1mmol)を加えた。この混合物を、窒素雰囲気下、110℃で2時間加熱撹拌した。
102 第1の電極
103 有機化合物を含む層
104 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
301 基板
302 第1の電極
304 第2の電極
311 電子輸送層
312 発光層
313 正孔輸送層
314 正孔注入層
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(ソース側駆動回路)
602 画素部
603 駆動回路部(ゲート側駆動回路)
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 有機化合物を含む層
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 有機化合物を含む層
956 電極
1201 ソース電極
1202 活性層
1203 ドレイン電極
1204 ゲート電極
2001 筐体
2002 光源
3001 照明装置
3002 照明装置
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
ス7306 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
Claims (22)
- 下記一般式(G1)で表されるカルバゾール化合物。
(但し、式中R1乃至R4はそれぞれ独立に水素、炭素数1乃至4のアルキル基、フェニル基及びトリル基のいずれかを表し、R5は炭素数6乃至12のアリール基を表す。また、R6乃至R13はそれぞれ独立に水素、炭素数1乃至4のアルキル基及び炭素数6乃至12のアリール基のいずれかを表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G2)で表されるカルバゾール化合物。
(但し、式中R1乃至R4はそれぞれ独立に水素、炭素数1乃至4のアルキル基、フェニル基及びトリル基のいずれかを表し、R5は炭素数6乃至12のアリール基を表す。また、R6、R7、R9及びR12はそれぞれ独立に水素、炭素数1乃至4のアルキル基及び炭素数6乃至12のアリール基のいずれかを表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G3)で表されるカルバゾール化合物。
(但し、式中R1乃至R4はそれぞれ独立に水素、炭素数1乃至4のアルキル基、フェニル基及びトリル基のいずれかを表し、R5は炭素数6乃至12のアリール基を表す。また、R7、R9及びR12はそれぞれ独立に水素、炭素数1乃至4のアルキル基及び炭素数6乃至12のアリール基のいずれかを表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G4)で表されるカルバゾール化合物。
(但し、式中R1乃至R4はそれぞれ独立に水素、炭素数1乃至4のアルキル基、フェニル基及びトリル基のいずれかを表し、R5は炭素数6乃至12のアリール基を表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G5)で表されるカルバゾール化合物。
(但し、式中R5は炭素数6乃至12のアリール基を表す。また、R6乃至R13はそれぞれ独立に水素、炭素数1乃至4のアルキル基及び炭素数6乃至12のアリール基のいずれかを表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G6)で表されるカルバゾール化合物。
(但し、式中R5は炭素数6乃至12のアリール基を表す。また、R6、R7、R9及びR12はそれぞれ独立に水素、炭素数1乃至4のアルキル基及び炭素数6乃至12のアリール基のいずれかを表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G7)で表されるカルバゾール化合物。
(但し、式中R5は炭素数6乃至12のアリール基を表す。また、R7、R9及びR12はそれぞれ独立に水素、炭素数1乃至4のアルキル基及び炭素数6乃至12のアリール基のいずれかを表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G8)で表されるカルバゾール化合物。
(但し、式中R5は炭素数6乃至12のアリール基を表す。また、Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G9)で表されるカルバゾール化合物。
(但し、式中Phは置換又は無置換のフェニレン基を表し、当該フェニレン基が置換基を有する場合、置換基としては炭素数1乃至4のアルキル基が適用できる。また、式中Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G10)で表されるカルバゾール化合物。
(但し、式中R5は炭素数6乃至12のアリール基を表す。また、R7、R9及びR12はそれぞれ独立に水素、炭素数1乃至4のアルキル基及び炭素数6乃至12のアリール基のいずれかを表す。また、Xは硫黄原子若しくは酸素原子である。) - 下記一般式(G11)で表されるカルバゾール化合物。
(但し、式中Xは硫黄原子若しくは酸素原子である。) - 下記構造式で表されるカルバゾール化合物。
- 下記構造式で表されるカルバゾール化合物。
- 請求項1又は請求項5において、R6乃至R13はそれぞれ独立に、水素、炭素数1乃至4のアルキル基、フェニル基、ナフチル基、ビフェニル基及びトリル基のいずれか一であるカルバゾール化合物。
- 請求項2、請求項3、請求項6、請求項7及び請求項10のいずれか一項において、
R6、R7、R9及びR12はそれぞれ独立に、水素、炭素数1乃至4のアルキル基、フェニル基、ナフチル基、ビフェニル基及びトリル基のいずれか一であるカルバゾール化合物。 - 請求項1乃至請求項8及び請求項10のいずれか一項において、R5がフェニル基、ナフチル基、ビフェニル基及びトリル基のいずれか一であるカルバゾール化合物。
- 請求項1乃至請求項16のいずれか一項に記載のカルバゾール化合物を含む有機半導体材料。
- 請求項1乃至請求項16のいずれか一項に記載のカルバゾール化合物を含む発光素子用材料。
- 一対の電極間に有機化合物を含む層を有し、
前記電極間に電圧をかけることにより前記有機化合物を含む層から光を得る発光素子であって、
前記有機化合物を含む層に、請求項1乃至請求項16のいずれか一項に記載のカルバゾール化合物を含む発光素子。 - 請求項19に記載の発光素子と、
前記発光素子を制御する手段とを含む発光装置。 - 請求項20に記載の発光装置を含む電子機器。
- 請求項19に記載の発光素子を光の供給手段として有する照明装置。
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KR101921042B1 (ko) | 2018-11-23 |
US8697885B2 (en) | 2014-04-15 |
KR20120059404A (ko) | 2012-06-08 |
US20120133274A1 (en) | 2012-05-31 |
JP5872861B2 (ja) | 2016-03-01 |
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