JP2016213470A - 化合物、発光素子、発光装置、電子機器、及び照明装置 - Google Patents
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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- JP2016213470A JP2016213470A JP2016095085A JP2016095085A JP2016213470A JP 2016213470 A JP2016213470 A JP 2016213470A JP 2016095085 A JP2016095085 A JP 2016095085A JP 2016095085 A JP2016095085 A JP 2016095085A JP 2016213470 A JP2016213470 A JP 2016213470A
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- 150000001875 compounds Chemical class 0.000 title claims description 277
- -1 benzofuropyridyl group Chemical group 0.000 claims abstract description 191
- 239000000126 substance Substances 0.000 claims abstract description 147
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 87
- 125000000732 arylene group Chemical group 0.000 claims abstract description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
- 150000002504 iridium compounds Chemical class 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 267
- 239000000463 material Substances 0.000 claims description 143
- 125000004432 carbon atom Chemical group C* 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
- 125000004434 sulfur atom Chemical group 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 229910052741 iridium Inorganic materials 0.000 claims description 17
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 17
- 150000001721 carbon Chemical class 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 14
- 229910052786 argon Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 description 98
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
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- 239000000243 solution Substances 0.000 description 29
- 238000006467 substitution reaction Methods 0.000 description 29
- 238000000034 method Methods 0.000 description 28
- 238000004770 highest occupied molecular orbital Methods 0.000 description 27
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 27
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 24
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- 238000000862 absorption spectrum Methods 0.000 description 24
- 238000005259 measurement Methods 0.000 description 24
- 239000000047 product Substances 0.000 description 24
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- 230000005284 excitation Effects 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000007983 Tris buffer Substances 0.000 description 22
- 239000002131 composite material Substances 0.000 description 22
- 238000000295 emission spectrum Methods 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 238000010521 absorption reaction Methods 0.000 description 20
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 19
- 239000011159 matrix material Substances 0.000 description 19
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- 230000005281 excited state Effects 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- 238000007789 sealing Methods 0.000 description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 150000002894 organic compounds Chemical class 0.000 description 15
- 125000002524 organometallic group Chemical group 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 239000010409 thin film Substances 0.000 description 15
- 238000012546 transfer Methods 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 150000002391 heterocyclic compounds Chemical class 0.000 description 14
- 239000012046 mixed solvent Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 13
- 150000002500 ions Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 229910052710 silicon Inorganic materials 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
- 239000010453 quartz Substances 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 239000011787 zinc oxide Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000002189 fluorescence spectrum Methods 0.000 description 10
- 238000001296 phosphorescence spectrum Methods 0.000 description 10
- 125000005595 acetylacetonate group Chemical group 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- 150000002367 halogens Chemical group 0.000 description 9
- 239000011229 interlayer Substances 0.000 description 9
- 238000000859 sublimation Methods 0.000 description 9
- 230000008022 sublimation Effects 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
- 229910052782 aluminium Inorganic materials 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 229910003437 indium oxide Inorganic materials 0.000 description 8
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 8
- 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 8
- 239000012298 atmosphere Substances 0.000 description 7
- 230000002349 favourable effect Effects 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 229910044991 metal oxide Inorganic materials 0.000 description 7
- 150000004706 metal oxides Chemical class 0.000 description 7
- 238000005192 partition Methods 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 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 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-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
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 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 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 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 5
- DGJMJPVDIVPMJP-UHFFFAOYSA-N 6-methoxy-[1]benzofuro[3,2-b]pyridine Chemical compound COC1=CC=CC2=C1OC=1C2=NC=CC=1 DGJMJPVDIVPMJP-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
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- 239000003446 ligand Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000000691 measurement method Methods 0.000 description 5
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- 229910000476 molybdenum oxide Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
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- 239000003566 sealing material Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 5
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- 239000010937 tungsten Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000001747 exhibiting effect Effects 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 230000001443 photoexcitation Effects 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- 229910001930 tungsten oxide Inorganic materials 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- FVCRQHSSGHZIDA-UHFFFAOYSA-N 8-[3-(3-carbazol-9-ylphenyl)phenyl]-[1]benzofuro[3,2-b]pyridine Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C=1C=C(C=CC=1)C1=CC(=CC=C1)C=1C=CC2=C(C3=NC=CC=C3O2)C=1 FVCRQHSSGHZIDA-UHFFFAOYSA-N 0.000 description 3
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 239000002023 wood Substances 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 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】一対の電極と、一対の電極の間に挟まれたEL層を有し、EL層は、カルバゾール骨格を有する物質を有し、物質は、カルバゾール骨格が有する窒素原子を介して、置換または無置換の第1のアリーレン基と結合され、第1のアリーレン基は、置換もしくは無置換のベンゾフロピリジル基、または、置換もしくは無置換のベンゾチエノピリジル基と結合され、第1のアリーレン基は、1乃至5連結した、置換もしくは無置換の第2のアリーレン基を有する、発光素子。EL層は、さらに発光中心物質を含む層を有していてもよい。また、EL層は、さらにイリジウム化合物を含む層を有していてもよい。
【選択図】図1
Description
本実施の形態で説明する本発明の一態様の化合物は、カルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する化合物である。当該構造を有する化合物は、キャリア(特に電子)の輸送性に優れる。このことから、駆動電圧の低い発光素子を提供することができる。
本実施の形態では、カルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する化合物を有する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。
2’)イリジウム(III)アセチルアセトナート(略称:[Ir(piq)2(acac)])のようなピリジン骨格を有する有機金属イリジウム錯体の他、2,3,7,8,12,13,17,18−オクタエチル−21H,23H−ポルフィリン白金(II)(略称:PtOEP)のような白金錯体や、トリス(1,3−ジフェニル−1,3−プロパンジオナト)(モノフェナントロリン)ユーロピウム(III)(略称:[Eu(DBM)3(Phen)])、トリス[1−(2−テノイル)−3,3,3−トリフルオロアセトナト](モノフェナントロリン)ユーロピウム(III)(略称:[Eu(TTA)3(Phen)])のような希土類金属錯体が挙げられる。なお、ピリミジン骨格を有する有機金属イリジウム錯体は、信頼性や発光効率にも際だって優れるため、特に好ましい。また、ピラジン骨格を有する有機金属イリジウム錯体は、色度の良い赤色発光が得られるため、白色発光素子に適用することで演色性を高めることができる。なお、カルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する本発明の一態様に係る化合物も、発光を呈することから、発光中心材料としての使用も可能である。
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。一つの発光ユニットは、実施の形態2で示したEL層103と同様な構成を有する。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、カルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する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3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3記載の発光素子は、カルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する、本発明の一態様に係る化合物を含む発光素子を含むことから、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3に記載の発光素子は、駆動電圧の低い発光素子であるため、駆動電圧の低い電子機器とすることが可能である。
本合成例では、実施の形態1で説明したカルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する化合物である8−[3’−(9H−カルバゾール−9−イル)ビフェニル−3−イル]ベンゾ[4,5]フロ[3,2−b]ピリジン(略称:mCzBPBfpy)(構造式(112))の合成方法について説明する。mCzBPBfpyの構造式を下に示す。
まず始めに、8−ブロモベンゾ[4,5]フロ[3,2−b]ピリジン1.6g(6.4mmol)と、3’−(9H−カルバゾール−9−イル)−3−ビフェニルボロン酸2.6g(7.0mmol)と、トリ(オルトートリル)ホスフィン0.19g(0.64mmol)と、炭酸カリウム1.8g(13mmol)と、トルエン60mLと、エタノール12mLと、水6.0mLとを、200mL三口フラスコに加えた。この混合物を、減圧下で攪拌することで脱気し、フラスコ内の気体を窒素置換した。この混合物に、酢酸パラジウム(II)29mg(0.13mmol)を加え、窒素気流下、80℃で24時間攪拌した。所定時間経過後、この反応混合物に水を加え、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、水、飽和食塩水で洗浄し、有機層に硫酸マグネシウムを加えて水分を吸着させた。この混合物を自然ろ過し、ろ液を濃縮して茶色固体を得た。得られた固体をシリカゲルカラムクロマトグラフィー(トルエン)で精製し、白色粉末を得た。この粉末を酢酸エチル/ヘキサンの混合溶媒を用いて再結晶したところ、目的物の白色粉末を収量2.0g、収率64%で得た。本ステップの合成スキームを下記式(B−1)に示す。
次に、mCzBPBfpyのトルエン溶液の吸収スペクトルを図12に、発光スペクトルを図13に示す。また、薄膜の吸収スペクトルを図14に、発光スペクトルを図15に示す。吸収スペクトルの測定には紫外可視分光光度計(日本分光株式会社製、V550型)を用いた。また、発光スペクトルの測定には、蛍光光度計(浜松ホトニクス株式会社製、FS920)を用いた。トルエン溶液のスペクトルは、mCzBPBfpyのトルエン溶液を石英セルに入れて測定した。また、薄膜のスペクトルは、mCzBPBfpyを石英基板に蒸着してサンプルを作製した。なお、トルエン溶液の吸収スペクトルは石英セルにトルエンのみを入れて測定した吸収スペクトルを差し引いた吸収スペクトルを図示し、薄膜の吸収スペクトルは石英基板の吸収スペクトルを差し引いた吸収スペクトルを図示した。
まず、第1の電極101として70nm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を用意した。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い、電極面積は2mm×2mmとした。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。
比較発光素子1は、発光層以外は発光素子1と同様に形成した。比較発光素子1の発光層は、8−[3−(N−フェニル−9H−カルバゾール−3−イル)−9H−カルバゾール−9−イル]ベンゾ[4,5]フロ[3,2−b]ピリジン(略称:PCCzBfpy)(構造式(v))、トリス(1,3−ジメチル−5−フェニル−1H−1,2,4−トリアゾラト)イリジウム(III)(略称:[Ir(Mptz1−Me)3])、を、PCCzBfpy:[Ir(Mptz1−Me)3]=1:0.06(質量比)となるよう共蒸着することにより30nmの膜厚で形成した。
以上により得られた発光素子1及び比較発光素子1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。
本合成例では、実施の形態1で説明したカルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する化合物である6−[3’−(9H−カルバゾール−9−イル)ビフェニル−3−イル]ベンゾ[4,5]フロ[3,2−b]ピリジン(略称:mCzBPBfpy‐02)(構造式(122))の合成方法について説明する。mCzBPBfpy‐02の構造式を下に示す。
500mL三口フラスコに2−ブロモ−3−ヒドロキシピリジン4.7g(27mmol)と2−フルオロ−3−メトキシフェニルボロン酸5.0g(29mmol)と炭酸カリウム15g(110mmol)を加えフラスコ内の気体を窒素置換した。これに250mLのジメチルアセトアミドを加え、減圧下で攪拌することにより脱気した。この混合物にテトラキストリフェニルホスフィンパラジウム(0)0.62g(0.53mmol)を加え、窒素気流下、90℃で44時間攪拌した。所定時間経過後、160℃で30時間撹拌した。所定時間経過後、反応混合物に水を加え、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、水、飽和食塩水で洗浄し、有機層に硫酸マグネシウムを加えて水分を吸着させた。この混合物を自然ろ過し、ろ液を濃縮して黒色液体を得た。この液体をシリカゲルカラムクロマトグラフィー(トルエン:酢酸エチル=9:1)で精製し、白色固体を1.7g、収率32%で得た。本ステップの合成スキームを下記式(C−1)に示す。
200mL三口フラスコに6−メトキシベンゾ[4,5]フロ[3,2−b]ピリジン1.7g(8.4mmol)を加えフラスコ内を窒素置換した。脱水ジクロロメタン60mLを加え、この混合物を0℃に冷却した。これに三臭化ホウ素(1Mジクロロメタン溶液)17mLを滴下し、室温で24時間攪拌した。所定時間経過後、反応混合物に水を加え、水層をジクロロメタンで抽出した。得られた抽出溶液と有機層を合わせ、飽和炭酸水素ナトリウム水溶液、水、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで乾燥した。この混合物を自然ろ過し、ろ液を濃縮して黄色固体の6−ヒドロキシベンゾ[4,5]フロ[3,2−b]ピリジンを2.2g得た。
100mL三口フラスコに1,1,1−トリフルオロメタンスルホン酸ベンゾ[4,5]フロ[3,2−b]ピリジン−6−イル0.75g(2.4mmol)、3’−(9H−カルバゾール−9−イル)−3−ビフェニルボロン酸0.94g(2.6mmol)、トリ(オルト−トリル)ホスフィン72mg(0.24mmol)、炭酸カリウム0.65g(4.7mmol)、トルエン25mL、エタノール10mL、水5.0mLを加えた。この混合物を、減圧下で攪拌することで脱気し、フラスコ内の気体を窒素置換した。この混合物に、酢酸パラジウム(II)11mg(0.047mmol)を加え、窒素気流下、80℃で24時間攪拌した。所定時間経過後、反応混合物に水を加え、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、水、飽和食塩水で洗浄し、有機層に硫酸マグネシウムを加えて水分を吸着させた。この混合物を自然ろ過し、ろ液を濃縮して茶色固体を得た。得られた固体をシリカゲルカラムクロマトグラフィー(クロロホルム)で精製し、無色透明の油状物を得た。得られた油状物をヘキサン/トルエンの混合溶媒を用いて再結晶したところ、白色粉末を得た。得られた白色粉末は高速液体カラムクロマトグラフィー(HPLC)で精製した。得られたフラクションを濃縮し、無色透明の油状物を得た。得られた油状物をヘキサン/酢酸エチルの混合溶媒を用いて再結晶したところ、目的物の白色粉末を0.41g、収率36%で得た。本ステップの合成スキームを下記式(C−3)に示す。
次に、mCzBPBfpy−02のトルエン溶液の吸収スペクトルと発光スペクトルを測定した。測定は溶液の吸収スペクトルと発光スペクトルは実施例1の測定と同様におこなった。
本計算においては、カルバゾール骨格とベンゾフロピリジル基とが結合している構造を有する化合物群において、該カルバゾール骨格に結合した置換基が、化合物のHOMO準位、LUMO準位、およびT1準位に与える影響について評価するために、下記の化合物についての計算を行った。
次に、カルバゾール骨格とベンゾフロピリジル基とが結合している構造を有する化合物群において、カルバゾール骨格とベンゾフロピリジル基との間のアリーレン基が化合物のHOMO準位、LUMO準位、およびT1準位に与える影響について評価するために、下記の化合物についての計算を行った。
次に、カルバゾール骨格とベンゾフロピリジル基とが結合している構造を有する化合物群において、カルバゾール骨格とベンゾフロピリジル基との間のアリーレン基の置換位置が、化合物のHOMO準位、LUMO準位、およびT1準位に与える影響について評価するために、下記の化合物についての計算を行った。
次に、カルバゾール骨格とベンゾフロピリジル基とが結合している構造を有する化合物群において、ベンゾフロピリジル基に結合するアリーレン基の置換位置が、化合物のHOMO準位、LUMO準位、およびT1準位に与える影響について評価するために、下記の化合物についての計算を行った。
次に、カルバゾール骨格とベンゾチエノピリジル基とが結合している構造を有する化合物群において、ベンゾチエノピリジル基に結合するアリーレン基の置換位置が、化合物のHOMO準位、LUMO準位、およびT1準位に与える影響について評価するために、下記の化合物についての計算を行った。
次に、カルバゾール骨格とベンゾフロピリジル基とが結合している構造を有する化合物群において、ベンゾフロピリジル基に結合するアリーレン基の置換位置が、化合物のHOMO準位、LUMO準位、およびT1準位に与える影響について評価するために、下記の化合物についての計算を行った。
次に、カルバゾール骨格とベンゾフロピリジル基とが結合している構造を有する化合物群において、ベンゾフロピリジル基に結合するアリーレン基の置換位置が、化合物のHOMO準位、LUMO準位、およびT1準位に与える影響について評価するために、下記の化合物についての計算を行った。
本合成例では、実施の形態1で説明したカルバゾール骨格と、ベンゾフロピリジル基もしくはベンゾチエノピリジル基とが、アリーレン基を介して結合している構造を有する化合物である4−[3’−(9H−カルバゾール−9−イル)ビフェニル−3−イル]ベンゾ[4,5]フロ[3,2−b]ピリジン(略称:mCzBPBfpy−03)(構造式(134))の合成方法について説明する。mCzBPBfpy−03の構造式を下に示す。
100mL三口フラスコにベンゾ[4,5]フロ[3,2−b]ピリジン0.66g(3.9mmol)を加え、フラスコ内雰囲気を窒素置換した。これに脱水テトラヒドロフラン40mLを加え、窒素気流下−80℃に冷却した。冷却後、この溶液に1.0Mのリチウム ジイソプロピルアミド(略称:LDA)4.7mL(4.7mmol)を滴下した。この溶液を同温度で0.5時間撹拌した。所定時間経過後、ヨウ素1.5g(5.9mmol)を加え、室温まで昇温し20時間撹拌した。所定時間経過後、この混合物にチオ硫酸ナトリウム水溶液を加え、酢酸エチルによる抽出を行った。得られた溶液をシリカゲルカラムクロマトグラフィー(展開溶媒:トルエン/酢酸エチル=9/1)で精製し、目的物の茶色固体を0.73g、収率64%で得た。下記式(D−1)に示す。
シュレンクフラスコに4−ヨードベンゾ[4,5]フロ[3,2−b]ピリジンを0.73g(2.5mmol)、3’−(9H−カルバゾール−9−イル)−3−ビフェニルボロン酸1.0g(2.8mmol)、トリ(オルト−トリル)ホスフィン76mg(0.25mmol)、炭酸カリウム0.69g(5.0mmol)、トルエン13mL、エタノール2.5mL、水1.3mLを加えた。この混合物を、減圧下で攪拌することで脱気した後、フラスコ内雰囲気を窒素置換した。この混合物に、酢酸パラジウム(II)11mg(0.050mmol)を加え、窒素気流下、90℃で10時間攪拌した。所定時間経過後、トルエンによる抽出を行い、その後シリカゲルカラムクロマトグラフィー(展開溶媒:クロロホルム)で精製し、黄色い油状物を得た。これをヘキサン/トルエンの混合溶媒を用いて再結晶したところ、目的物の黄色粉末を収量0.75g、収率60%で得た。下記式(D−2)に示す。
次に、mCzBPBfpy−03のトルエン溶液の吸収スペクトルを図22に、発光スペクトルを図25に示す。また、薄膜の吸収スペクトルを図26に、発光スペクトルを図27に示す。測定法は溶液の吸収スペクトルと発光スペクトル、薄膜の発光スペクトルは実施例1の測定と同様におこなった。薄膜の吸収スペクトルの測定には紫外可視分光光度計(日立ハイテクノロジーズ製、U4100型)を用い、石英基板を含むスペクトルを求めた。
発光素子2は、正孔輸送層112から電子注入層115まで以外は発光素子1と同様に形成した。発光素子1の正孔輸送層112を3,3’−ビス(9−フェニル−9H−カルバゾール)(略称:PCCP)を20nmの膜厚で形成した。続けて、発光層113をPCCPとmCzBPBfpy−03とトリス{2−[5−(2−メチルフェニル)−4−(2,6−ジイソプロピルフェニル)−4H−1,2,4−トリアゾール−3−イル−κN2]フェニル−κC}イリジウム(III)(略称:[Ir(mpptz−diPrp)3])をPCCP:mCzBPBfpy−03:[Ir(mpptz−diPrp)3]=1:0.3:0.06(質量比)となるよう共蒸着することにより30nmの膜厚で形成し、続けてmCzBPBfpy−03:Ir(mpptz−diPrp)3=1:0.06(質量比)となるよう共蒸着することにより10nmの膜厚で形成した。続けて、電子輸送層114をmCzBPBfpy−03を10nmの膜厚で形成した。続けて、電子注入層115をバソフェナントロリン(略称:BPhen)を15nmの膜厚で形成し、続けてフッ化リチウムを1nmの膜厚で形成した。
以上により得られた発光素子2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。
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
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 引き回し配線
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
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
1001 基板
1002 下地絶縁膜
1003 ゲート絶縁膜
1006 ゲート電極
1007 ゲート電極
1008 ゲート電極
1020 第1の層間絶縁膜
1021 第2の層間絶縁膜
1022 電極
1024B 第1の電極
1024G 第1の電極
1024R 第1の電極
1024W 第1の電極
1025 隔壁
1028 EL層
1029 第2の電極
1031 封止基板
1032 シール材
1033 透明な基材
1034B 青色の着色層
1034G 緑色の着色層
1034R 赤色の着色層
1036 オーバーコート層
1037 第3の層間絶縁膜
1040 画素部
1041 駆動回路部
1042 周辺部
2001 筐体
2002 光源
3001 照明装置
3002 表示装置
5000 表示領域
5001 表示領域
5002 表示領域
5003 表示領域
5004 表示領域
5005 表示領域
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
7312 マイクロフォン
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
Claims (29)
- 一対の電極と、
前記一対の電極の間に挟まれたEL層を有し、
前記EL層は、カルバゾール骨格を有する物質を有し、
前記物質は、前記カルバゾール骨格が有する窒素原子を介して、置換または無置換の第1のアリーレン基と結合され、
前記第1のアリーレン基は、置換もしくは無置換のベンゾフロピリジル基、または、置換もしくは無置換のベンゾチエノピリジル基と結合され、
前記第1のアリーレン基は、1乃至5連結した、置換もしくは無置換の第2のアリーレン基を有する、発光素子。 - 請求項1において
前記EL層は、発光中心物質を含む層を有する、発光素子。 - 請求項1または請求項2において、
前記EL層は、イリジウム化合物を含む層を有する、発光素子。 - 下記一般式(G1)で表される化合物。
(式中A1は置換もしくは無置換のベンゾフロピリジル基もしくは置換もしくは無置換のベンゾチエノピリジル基を表し、Arは置換もしくは無置換の炭素数6乃至13のアリーレン基を表し、R11乃至R18は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、nは1乃至5の自然数を表す。) - 下記一般式(G2−1)で表される化合物。
(式中Arは置換もしくは無置換の炭素数6乃至13のアリーレン基を表し、R11乃至R18は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、nは1乃至5の自然数を表す。また、式中Yは、下記(G2−2)で表される。)
(式中R21乃至R27の一つは、(G2−1)のYとArとの間の単結合を表し、それ以外は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Q1は酸素原子または硫黄原子を表す。) - 下記一般式(G3−1)で表される化合物。
(式中R11乃至R18及びR31乃至R34は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または、置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、nは1乃至5の自然数を表す。また、式中Yは、下記(G3−2)で表される。)
(式中R21乃至R27の一つは、(G3−1)のYとフェニレン骨格との間の単結合を表し、その他のR21乃至R27は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Q1は酸素原子または硫黄原子を表す。) - 下記一般式(G4−1)で表される化合物。
(式中R11乃至R18、R31乃至R34及びR41乃至R44は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または、置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、式中Yは、下記(G4−2)で表される。)
(式中R21乃至R27の一つは、(G4−1)のYとフェニレン骨格との間の単結合を表し、その他のR21乃至R27は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Q1は酸素原子または硫黄原子を表す。) - 請求項5乃至7のいずれか一項において、
R25、R27またはR21のいずれか一がYとフェニレン骨格との間の前記単結合を表す、化合物。 - 下記化学式(112)で表される化合物。
- 下記化学式(122)で表される化合物。
- 下記化学式(134)で表される化合物。
- 一対の電極と、前記一対の電極の間に挟まれた有機層を有し、
前記有機層に、請求項3乃至請求項11のいずれか一項に記載の化合物を含む電子機器。 - 一対の電極と、前記一対の電極の間に挟まれたEL層を有し、
前記EL層に、請求項3乃至請求項11のいずれか一項に記載の化合物を含む発光素子。 - 請求項1乃至請求項3、または、請求項13のいずれか一項において、
前記EL層は、さらに発光中心物質を有する発光素子。 - 請求項1乃至請求項3、または、請求項13乃至請求項14のいずれか一項において、
前記EL層は、さらにイリジウム錯体を有する発光素子。 - 請求項1乃至請求項3、または、請求項13乃至請求項15のいずれか一項に記載の発光素子と、
ドライバと、FPCと、を有するディスプレイモジュール。 - 請求項1乃至請求項3、または、請求項13乃至請求項15のいずれか一項に記載の発光素子と、
前記発光素子を収納する容器と、を有する照明モジュール。 - 請求項1乃至請求項3、または、請求項13乃至請求項15のいずれか一項に記載の発光素子と、
前記発光素子を制御する手段を備えた発光装置。 - 請求項1乃至請求項3、または、請求項13乃至請求項15のいずれか一項に記載の発光素子と、
前記発光素子を制御する手段を備えた表示装置。 - 請求項1乃至請求項3、または、請求項13乃至請求項15のいずれか一項に記載の発光素子と、
前記発光素子を制御する手段を備えた照明装置。 - 請求項1乃至請求項3、または、請求項13乃至請求項15のいずれか一項に記載の発光素子と、
操作スイッチと、を有する電子機器。 - 下記一般式(G5)で表される化合物。
(式中R21乃至R26は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Q1は酸素原子または硫黄原子を表す。R100はトリフラート基、メシラート基、モノクラート基のいずれかを表す。) - 下記化学式(400)で表される化合物。
- 下記一般式(G6)で表される化合物。
(式中R21乃至R26は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Q1は酸素原子を表す。R101は置換もしくは無置換の炭素数1乃至6のアルキル基を表す。) - 下記化学式(410)で表される化合物。
- 下記一般式(G7)で表される化合物。
(式中R21乃至R26は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Q1は酸素原子または硫黄原子を表す。) - 下記化学式(420)で表される化合物。
- 下記一般式(G8)で表される化合物。
(式中R22乃至R27は各々独立に水素、置換もしくは無置換の炭素数1乃至6のアルキル基、または置換もしくは無置換の炭素数6乃至13のアリール基を表す。また、Q1は酸素原子または硫黄原子を表す。Xはハロゲンを表す。) - 下記化学式(430)で表される化合物。
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