JP7430646B2 - Elデバイス、発光装置、電子機器、および照明装置 - Google Patents
Elデバイス、発光装置、電子機器、および照明装置 Download PDFInfo
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- JP7430646B2 JP7430646B2 JP2020556365A JP2020556365A JP7430646B2 JP 7430646 B2 JP7430646 B2 JP 7430646B2 JP 2020556365 A JP2020556365 A JP 2020556365A JP 2020556365 A JP2020556365 A JP 2020556365A JP 7430646 B2 JP7430646 B2 JP 7430646B2
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- 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
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 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
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- FPOBXNYAWLLCGZ-UHFFFAOYSA-N nickel(2+);1,2,3,4,5-pentamethylcyclopenta-1,3-diene Chemical compound [Ni+2].CC=1C(C)=C(C)[C-](C)C=1C.CC=1C(C)=C(C)[C-](C)C=1C FPOBXNYAWLLCGZ-UHFFFAOYSA-N 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-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
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- BZBAYMUKLAYQEO-UHFFFAOYSA-N phenylborane Chemical compound BC1=CC=CC=C1 BZBAYMUKLAYQEO-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HYXGAEYDKFCVMU-UHFFFAOYSA-N scandium oxide Chemical compound O=[Sc]O[Sc]=O HYXGAEYDKFCVMU-UHFFFAOYSA-N 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- DKWSBNMUWZBREO-UHFFFAOYSA-N terbium Chemical compound [Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb][Tb] DKWSBNMUWZBREO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 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 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-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
- 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
- ZVWKZXLXHLZXLS-UHFFFAOYSA-N zirconium nitride Chemical compound [Zr]#N ZVWKZXLXHLZXLS-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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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
- H10K85/30—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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- H10K85/631—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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- H10K85/649—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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Description
[先行技術文献]
[特許文献]
図2Aおよび図2Bは、アクティブマトリクス型発光装置の概念図である。
図3Aおよび図3Bは、アクティブマトリクス型発光装置の概念図である。
図4は、アクティブマトリクス型発光装置の概念図である。
図5Aおよび図5Bは、パッシブマトリクス型発光装置の概念図である。
図6Aおよび図6Bは、照明装置を表す図である。
図7A、図7B1、図7B2および図7Cは、電子機器を表す図である。
図8A乃至図8Cは、電子機器を表す図である。
図9は、照明装置を表す図である。
図10は、照明装置を表す図である。
図11は、車載表示装置及び照明装置を表す図である。
図12Aおよび図12Bは、電子機器を表す図である。
図13A乃至図13Cは、電子機器を表す図である。
図14Aおよび図14Bは、F9BPPadの1H NMRチャートである。
図15Aおよび図15Bは、F9BPPadの19F-NMRチャートである。
図16Aおよび図16Bは、Pad2F8BPの1H NMRチャートである。
図17Aおよび図17Bは、Pad2F8BPの19F-NMRチャートである。
図18は、F9BPPad、Pad2F8BP、DBT3P-IIおよびFATPAを用いた複合材料の屈折率を表すグラフである。
図19は、F9BPPadのトルエン溶液中における吸収スペクトルおよび発光スペクトルである。
図20は、Pad2F8BPのトルエン溶液中における吸収スペクトルおよび発光スペクトルである。
図21は、ELデバイス1-0、ELデバイス2-0、比較ELデバイス1-0および比較ELデバイス2-0の輝度-電流密度特性である。
図22は、ELデバイス1-0、ELデバイス2-0、比較ELデバイス1-0および比較ELデバイス2-0の電流効率-輝度特性である。
図23は、ELデバイス1-0、ELデバイス2-0、比較ELデバイス1-0および比較ELデバイス2-0の輝度-電圧特性である。
図24は、ELデバイス1-0、ELデバイス2-0、比較ELデバイス1-0および比較ELデバイス2-0の電流-電圧特性である。
図25は、ELデバイス1-0、ELデバイス2-0、比較ELデバイス1-0および比較ELデバイス2-0の外部量子効率-輝度特性である。
図26は、ELデバイス1-0、ELデバイス2-0、比較ELデバイス1-0および比較ELデバイス2-0の発光スペクトルである。
図27は、実施例のELデバイスと、比較例のELデバイスの1000cd/m2付近における色度xと外部量子効率との関係である。
図28は、実施例のELデバイスと、比較例のELデバイスの規格化輝度-時間変化特性である。
図29は、F9BPPadのMSスペクトルである。
図30は、Pad2F8BPのMSスペクトルである。
有機ELデバイス(以下、ELデバイスとも言う)は、通常、発光層やキャリア輸送層、キャリア注入層など、機能分離された複数の層から構成される有機化合物を含む層(EL層ともいう)を一対の電極間に挟んだ構造を有する。陽極と発光層との間には、正孔注入層や正孔輸送層が形成され、電極からEL層へ正孔をスムーズに注入し、発光層へ正孔を速やかに輸送および注入する役割を担う。
本実施の形態では、実施の形態1で示したELデバイスの詳しい態様について説明する。図1に、本発明の一態様のELデバイスを表す図を示す。図1Aに示したELデバイスは、陽極101と、陰極102、EL層103を有する。本発明の一態様のELデバイスは、EL層103に実施の形態1で説明した上記アリールアミン骨格またはアクリジン骨格を有し、フッ素を含む有機化合物(第1の物質)を含んでいる。第1の物質はEL層103中において、第2の物質と共に第1の層を形成していることが好ましい。なお、第1の物質は、第2の物質に電子供与性を示すものとする。
本実施の形態では、実施の形態2に記載のELデバイス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2に記載のELデバイスを照明装置として用いる例を図6を参照しながら説明する。図6Bは照明装置の上面図、図6Aは図6B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2に記載のELデバイス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2に記載のELデバイスは発光効率が良好であり、消費電力が小さいELデバイスである。その結果、本実施の形態に記載の電子機器は、消費電力が小さい発光部を有する電子機器とすることが可能である。
本実施例では、本発明の一態様である有機化合物、10-(2,2’,3,3’,4’,5,5’,6,6’-ノナフルオロ-4-ビフェニリル)9,9-ジフェニル-9H,10H-アクリジン(略称:F9BPPad)および10,10’-(2,2’,3,3’,5,5’,6,6’-オクタフルオロビフェニレン-4,4’-ジイル)ビス(9,9-ジフェニル-9H,10H-アクリジン)(略称:Pad2F8BP)の合成方法について説明する。F9BPPadおよびPad2F8BPの構造を以下に示す。
三口フラスコにリチウムアミド0.41g(16.5mmol)を入れ、一旦減圧操作をした後、フラスコ内を窒素置換した。このフラスコに脱水THF15mLを加え、撹拌した。この懸濁液に、9,9-ジフェニル-10H-アクリジン5.0g(15mmol)のTHF溶液45mLをシリンジにて滴下した。この混合懸濁液を約3時間室温にて撹拌し、反応させた。この混合物を-78℃に冷却した。冷却後、この混合物にデカフルオロビフェニル5.0g(15mmol)のTHF溶液15mLをシリンジにて滴下し、約2時間反応させた。この混合物を室温まで昇温し、一晩撹拌した。撹拌後、この混合物に水約50mLを加え、分液した。得られた水層を酢酸エチルで抽出した。分液して得られた有機層と抽出で得られた酢酸エチルを混合し、飽和炭酸水素ナトリウム水溶液で洗浄し、分液した。得られた有機層を硫酸マグネシウムを用いて水分を乾燥させた後、ろ別しエバポレータで溶媒を留去した。得られた混合物を、シリカゲルカラムクロマトグラフィーにて分離精製し、二種類の白色固体を得た。得られた二種類の白色固体のうち、一方は、10-(2,2’,3,3’,4’,5,5’,6,6’-ノナフルオロ-4-ビフェニリル)9,9-ジフェニル-9H,10H-アクリジン(略称:F9BPPad)3.2g(4.95mmol)(収率33%)で、他方は10,10’-(2,2’,3,3’,5,5’,6,6’-オクタフルオロビフェニレン-4,4’-ジイル)ビス(9,9-ジフェニル-9H,10H-アクリジン)(略称:Pad2F8BP)3.1g(3.20mmol)、(収率43%)であった。ステップ1の合成スキームを以下に示す。
1H-NMR.δ(CDCl3):7.17-7.28(m,8H),6.94-7.04(m,8H),6.48(d,2H,J=7.5Hz).
19F-NMR.δ(CDCl3):-159.9,-149.3,-141.7,-136.9,-136.3.
1H-NMR.δ(CDCl3):7.18-7.29(m,16H),6.95-7.05(m,16H),6.50(d,4H,J=8.0Hz).
19F-NMR.δ(CDCl3):-141.0,-136.0.
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、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は2mm×2mmとした。
ELデバイス1-1はELデバイス1-0における正孔注入層111を、F9BPPadと酸化モリブデン(VI)とを、重量比で2:0.5(=F9BPPad:酸化モリブデン)となるように50nm共蒸着した後、上記構造式(v)で表される4,4’,4’’-(ベンゼン-1,3,5-トリイル)トリ(ジベンゾチオフェン)(略称:DBT3P-II)と酸化モリブデン(VI)とを、重量比で2:0.5(=DBT3P-II:酸化モリブデン)となるように5nm共蒸着して正孔注入層111を形成した他はELデバイス1-0と同様に作製した。
ELデバイス2-0は、ELデバイス1-0における正孔注入層111で用いたF9BPPadを上記構造式(200)で表される10,10’-(2,2’,3,3’,5,5’,6,6’-オクタフルオロビフェニレン-4,4’-ジイル)ビス(9,9-ジフェニル-9H,10H-アクリジン)(略称:Pad2F8BP)に変えた他はELデバイス1-0と同様に作製した。
比較ELデバイス1-0は、ELデバイス1-0における正孔注入層111で用いたF9BPPadをDBT3P-IIに変えた他はELデバイス1-0と同様に作製した。
比較ELデバイス2-0は、ELデバイス1-0における正孔注入層111で用いたF9BPPadを上記構造式(vi)で表される4,4,8,8,12,12-ヘキサ-p-トリル-4H-8H-12H-12C-アザ-ジベンゾ[cd,mn]ピレン(略称:FATPA)に変えた他はELデバイス1-0と同様に作製した。
Claims (11)
- 陽極と、陰極と、前記陽極および前記陰極の間に、正孔注入層と、発光層と、を有し、
前記正孔注入層は、前記陽極と接しており、
前記正孔注入層は、第1の物質と第2の物質とを含み、
前記第1の物質は、前記第2の物質に対して電子供与性を示す物質であり、
前記第1の物質は、式(G2)で表される化合物であるELデバイス。
(一般式(G2)において、R1乃至R4およびR7乃至R10は、それぞれ独立に水素、炭素数1乃至6のアルキル基および炭素数1乃至6のフッ化アルキル基のいずれかである。R5およびR6は、それぞれ独立に水素、炭素数1乃至6のアルキル基、炭素数1乃至6のフッ化アルキル基および置換または無置換のフェニル基のいずれかである。R33はフッ素または下記一般式(g1)で表される基のいずれかである。)
(一般式(g1)において、R21乃至R24およびR27乃至R30は、それぞれ独立に水素、炭素数1乃至6のアルキル基および炭素数1乃至6のフッ化アルキル基のいずれかである。R25およびR26は、それぞれ独立に水素、炭素数1乃至6のアルキル基、炭素数1乃至6のフッ化アルキル基および置換または無置換のフェニル基のいずれかである。) - 請求項1において、
前記第1の物質の屈折率が1.8以下であるELデバイス。 - 請求項1または請求項2において、
前記第2の物質がモリブデン酸化物であるELデバイス。 - 請求項1乃至請求項3のいずれか一項において、
R1乃至R4およびR7乃至R10は、それぞれ独立に水素であるELデバイス。 - 請求項1乃至請求項4のいずれか一項において、
R21乃至R24およびR27乃至R30は、それぞれ独立に水素であるELデバイス。 - 請求項1乃至請求項5のいずれか一項において、
R5およびR6は、それぞれ独立にフェニル基であるELデバイス。 - 請求項1乃至請求項6のいずれか一項において、
R25およびR26は、それぞれ独立にフェニル基であるELデバイス。 - 請求項1乃至請求項7のいずれか一項において、
前記正孔注入層の膜厚が20nm以上であるELデバイス。 - 請求項1乃至請求項8のいずれか一項に記載のELデバイスと、トランジスタ、または、基板と、を有する発光装置。
- 請求項9に記載の発光装置と、センサ、操作ボタン、スピーカ、または、マイクと、
を有する電子機器。 - 請求項9に記載の発光装置と、筐体と、を有する照明装置。
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