JP5875321B2 - フェナントレン化合物、発光素子、発光装置、電子機器及び照明装置 - Google Patents
フェナントレン化合物、発光素子、発光装置、電子機器及び照明装置 Download PDFInfo
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- JP5875321B2 JP5875321B2 JP2011233561A JP2011233561A JP5875321B2 JP 5875321 B2 JP5875321 B2 JP 5875321B2 JP 2011233561 A JP2011233561 A JP 2011233561A JP 2011233561 A JP2011233561 A JP 2011233561A JP 5875321 B2 JP5875321 B2 JP 5875321B2
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- -1 Phenanthrene compound Chemical class 0.000 title claims description 101
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 title claims description 62
- 239000000463 material Substances 0.000 claims description 64
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- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
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- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 238000005286 illumination Methods 0.000 claims description 3
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 15
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- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 12
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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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
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- 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
- 125000005595 acetylacetonate group Chemical group 0.000 description 7
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- CSHWQDPOILHKBI-UHFFFAOYSA-N perylene Chemical compound C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
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- 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 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 150000001639 boron compounds Chemical class 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-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
- 239000002019 doping agent Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
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- 238000010438 heat treatment Methods 0.000 description 6
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- 238000005259 measurement 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
- 238000000859 sublimation Methods 0.000 description 6
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- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
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- 239000011777 magnesium Substances 0.000 description 5
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 5
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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 5
- FHLAIKCAZNTSAN-UHFFFAOYSA-N 4-(4-phenanthren-9-ylphenyl)dibenzothiophene Chemical compound C1=CC=C2C(C3=CC=C(C=C3)C3=C4SC=5C(C4=CC=C3)=CC=CC=5)=CC3=CC=CC=C3C2=C1 FHLAIKCAZNTSAN-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound 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 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
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- NKHSXZJAUZUJHT-UHFFFAOYSA-N 4-[3-(3-phenanthren-9-ylphenyl)phenyl]dibenzothiophene Chemical compound C1=CC=C2C(C=3C=CC=C(C=3)C=3C=CC=C(C=3)C3=C4SC=5C(C4=CC=C3)=CC=CC=5)=CC3=CC=CC=C3C2=C1 NKHSXZJAUZUJHT-UHFFFAOYSA-N 0.000 description 3
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 3
- 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
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000003981 vehicle Substances 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
- 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
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- H—ELECTRICITY
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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
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- 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
- H10K50/166—Electron transporting layers comprising a multilayered structure
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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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- H—ELECTRICITY
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- 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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- H10K2101/00—Properties of the organic materials covered by group H10K85/00
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- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
- Y02B20/30—Semiconductor lamps, e.g. solid state lamps [SSL] light emitting diodes [LED] or organic LED [OLED]
Description
本実施の形態では、本発明の一態様に係るフェナントレン化合物について説明する。
合成スキーム(A−1)に示すように、フェナントレン誘導体のハロゲン化物(化合物1)と、ジベンゾフラン誘導体若しくはジベンゾチオフェン誘導体の有機ボロン化合物、又はジベンゾフラン誘導体若しくはジベンゾチオフェン誘導体のボロン酸(化合物2)とを、鈴木・宮浦反応によりカップリングさせることで、一般式(G1)で表されるフェナントレン化合物を得ることができる。
合成スキーム(B−1)に示すように、フェナントレン誘導体のハロゲン化物(化合物3)と、ジベンゾフラン誘導体若しくはジベンゾチオフェン誘導体の有機ボロン化合物、又はジベンゾフラン誘導体若しくはジベンゾチオフェン誘導体のボロン酸(化合物4)とを、鈴木・宮浦反応によりカップリングさせることで、一般式(G1)で表されるフェナントレン化合物を得ることができる。
本実施の形態では、本発明の一態様として、実施の形態1で説明したフェナントレン化合物を用いた発光素子について図1を用いて説明する。
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、積層型素子という)の態様について、図2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。
本実施の形態では、本発明の一態様の発光装置について図3を用いて説明する。なお、図3(A)は、発光装置を示す上面図、図3(B)は図3(A)をA−B及びC−Dで切断した断面図である。
本実施の形態では、本発明を適用した一態様である発光装置を用いて完成させた様々な電子機器および照明器具の一例について、図5乃至図7を用いて説明する。
1H NMR(CDCl3,300MHz):δ(ppm)=7.46−7.53(m,2H)、7.58−7.73(m,8H)、7.80(s,1H)、7.87−7.96(m,4H)、8.07(d,J=8.1Hz,1H)、8.18−8.24(m,2H)、8.76(d,J=8.1Hz,1H)、8.82(d,J=7.8Hz,1H)。
まず、ガラス基板1100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1101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。本実施例において、第1の電極1101は、陽極として用いた。
1H NMR(CDCl3,300MHz):δ(ppm)=7.44−7.48(m,2H)、7.52−7.84(m,14H)、7.89−7.92(m,2H)、8.01(dd,1H)、8.07−8.08(m,1H)、8.14−8.21(m,2H)、8.74(d,1H)、8.79(d,1H)。
まず、ガラス基板1100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1101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。本実施例において、第1の電極1101は、陽極として用いた。
発光素子2と同一基板を用い、発光層にDBTPPn−IIの代わりに、実施例3で示した4−[3’−(9−フェナントリル)ビフェニル−3−イル]ジベンゾチオフェン(略称:mDBTBPPn−II)を用いて発光素子2と同様に作製した。つまり、発光素子3の発光層は、mDBTBPPn−IIと、トリス(2−フェニルピリジナト−N,C2’)イリジウム(III)(略称:Ir(ppy)3)と、を共蒸着することにより作製した。ここで、発光層は、mDBTBPPn−II及びIr(ppy)3の重量比が、1:0.08(=mDBTBPPn−II:Ir(ppy)3)となるように調節し、膜厚10nmとした第1の発光層1113aと、mDBTBPPn−II及びIr(ppy)3の重量比が、1:0.04(=mDBTBPPn−II:Ir(ppy)3)となるように調節し、膜厚20nmとした第2の発光層1113bとの積層構造とした。
本参考例では、発光素子1乃至発光素子3の材料に用いた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)を合成する例を示す。
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。ここに脱水ジエチルエーテル10mL中に溶かした2−ブロモビフェニルを12g(50mmol)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、反応させた。
1H NMR(CDCl3、300MHz):δ(ppm)=6.63−7.02(m、3H)、7.06−7.11(m、6H)、7.19−7.45(m、18H)、7.53−7.55(m、2H)、7.75(d、J=6.9、2H)。
101 電極
102 EL層
103 電極
111 正孔注入層
112 正孔輸送層
113 発光層
113a 発光層
113b 発光層
114 電子輸送層
115 電子注入層
301 電極
303 電極
311 発光ユニット
312 発光ユニット
313 電荷発生層
401 ソース側駆動回路
402 画素部
403 ゲート側駆動回路
404 封止基板
405 シール材
407 空間
408 配線
409 FPC(フレキシブルプリントサーキット)
410 素子基板
411 スイッチング用TFT
412 電流制御用TFT
413 電極
414 絶縁物
416 EL層
417 電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
501 基板
502 電極
503 電極
504 EL層
505 絶縁層
506 隔壁層
600 表示装置
602 表示装置
604 表示部
606 表示部
801 照明装置
803 照明装置
805 メガネ
1100 ガラス基板
1101 電極
1103 電極
1111 正孔注入層
1112 正孔輸送層
1113 発光層
1114a 電子輸送層
1114b 電子輸送層
1115 電子注入層
7100 テレビジョン装置
7100a テレビジョン装置
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
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 入力手段(操作キー
7310 接続端子
7311 センサ
7312 マイクロフォン
7400 携帯電話機
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
7500 照明装置
7501 筐体
7503a 発光装置
7503b 発光装置
7503c 発光装置
7503d 発光装置
Claims (8)
- 下記式(G1)で表されるフェナントレン化合物。
(但し、式(G1)中、R11〜R19及びR21〜R27はそれぞれ独立に、水素、炭素数1〜4のアルキル基、又は炭素数6〜13の置換若しくは無置換のアリール基のいずれか一を表す。また、Arは、式(Ar−1)で表される置換基を表す。また、Zは硫黄原子または酸素原子を表す。)
- 下記式(G1)で表されるフェナントレン化合物。
(但し、式(G1)中、R 11 〜R 19 及びR 21 〜R 27 はそれぞれ独立に、式(R−1)〜(R23)で表されるいずれかの置換基を表す。また、Arは、式(Ar−1)で表される置換基を表す。また、Zは硫黄原子または酸素原子を表す。)
- 式(100)で表されるフェナントレン化合物。
- 請求項1乃至3のいずれか一に記載のフェナントレン化合物を含む発光素子。
- 請求項1乃至3のいずれか一に記載のフェナントレン化合物と、燐光性発光物質と、を発光層に含む発光素子。
- 請求項4または5に記載の発光素子を有する発光装置。
- 請求項6に記載の発光装置を搭載した電子機器。
- 請求項6に記載の発光装置を搭載した照明装置。
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