JP6841672B2 - 発光素子、正孔輸送層用材料、発光素子用材料、発光装置、電子機器、および照明装置 - Google Patents
発光素子、正孔輸送層用材料、発光素子用材料、発光装置、電子機器、および照明装置 Download PDFInfo
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- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229960003569 hematoporphyrin Drugs 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000012905 input function Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- WOYDRSOIBHFMGB-UHFFFAOYSA-N n,9-diphenyl-n-(9-phenylcarbazol-3-yl)carbazol-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(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 WOYDRSOIBHFMGB-UHFFFAOYSA-N 0.000 description 1
- BBNZOXKLBAWRSH-UHFFFAOYSA-N n,9-diphenyl-n-[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)C2=CC=1)C1=CC=C(C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=C3C=CC=CC3=2)C=C1 BBNZOXKLBAWRSH-UHFFFAOYSA-N 0.000 description 1
- NCCYEOZLSGJEDF-UHFFFAOYSA-N n,n,9-triphenyl-10h-anthracen-9-amine Chemical compound C12=CC=CC=C2CC2=CC=CC=C2C1(C=1C=CC=CC=1)N(C=1C=CC=CC=1)C1=CC=CC=C1 NCCYEOZLSGJEDF-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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- MSCLVLGBAGCXEC-UHFFFAOYSA-N n-phenyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-9,9'-spirobi[fluorene]-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=C(C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MSCLVLGBAGCXEC-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001151 other effect Effects 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
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 150000005359 phenylpyridines Chemical class 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 150000003057 platinum Chemical class 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
- 238000005381 potential energy Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 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
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- HYXGAEYDKFCVMU-UHFFFAOYSA-N scandium oxide Chemical compound O=[Sc]O[Sc]=O HYXGAEYDKFCVMU-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing 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
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 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
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 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
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 238000007736 thin film deposition technique Methods 0.000 description 1
- 229930192474 thiophene Natural products 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
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 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
- 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
- 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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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- 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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Description
有機材料を用いた発光素子の場合、その寿命に影響を及ぼす要素にはさまざまなものがあるが、特に、正孔輸送材料の特性が大きく影響を及ぼす場合がある。その中でも、正孔輸送材料の輸送性の影響は大きく、正孔輸送材料の種類によって、その寿命に大きな違いが出てくる。
これら導電性材料は、真空蒸着法やスパッタリング法などの乾式法、インクジェット法、スピンコート法等を用いて成膜することが可能である。また、ゾル−ゲル法を用いて湿式法で形成しても良いし、金属材料のペーストを用いて湿式法で形成してもよい。
本実施の形態では、本発明の一態様の有機化合物について説明する。
本発明の一態様の有機化合物である一般式(G1−a)で表される有機化合物は、下記合成スキーム(a−1)または(a−2)のように合成することができる。
本発明の一般式(G1−b)で表される有機化合物は、下記合成スキーム(b−1)または(b−2)のように合成することができる。
本実施の形態では、実施の形態1に記載の発光素子を用いた発光装置について説明する。
本実施の形態では、実施の形態1に記載の発光素子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6(B)は照明装置の上面図、図6(A)は図6(B)におけるe−f断面図である。
本実施の形態では、実施の形態1に記載の発光素子をその一部に含む電子機器の例について説明する。実施の形態1に記載の発光素子は寿命が良好であり、信頼性の良好な発光素子である。その結果、本実施の形態に記載の電子機器は、信頼性の良好な発光部を有する電子機器とすることが可能である。
本合成例では、実施の形態において構造式(142)として表された本発明の一態様の有機化合物、N−(4−ビフェニル)−6,N−ジフェニルベンゾ[b]ナフト[1,2−d]フラン−8−アミン(略称:BnfABP)の合成例を具体的に例示する。BnfABPの構造式を以下に示す。
500mL三口フラスコに、8.5g(39mmol)のベンゾ[b]ナフト[1,2−d]フランを加え、フラスコ内を窒素置換した後、195mLのテトラヒドロフラン(THF)を加えた。この溶液を−75℃に冷却してから、この溶液に25mL(40mmol)のn−ブチルリチウム(1.59mol/L n−ヘキサン溶液)を滴下して加えた。滴下後、得られた溶液を室温で1時間攪拌した。所定時間経過後、この溶液を−75℃に冷却してから、ヨウ素10g(40mmol)をTHF40mLに溶かした溶液を滴下して加えた。滴下後、得られた溶液を室温に戻しながら17時間攪拌した。その後、この混合物にチオ硫酸ナトリウム水溶液を加え、1時間攪拌した後、この混合物の有機層を水で洗浄し、有機層を硫酸マグネシウムにより乾燥した。乾燥後、この混合物を自然濾過し、得られた溶液をフロリジール(和光純薬工業株式会社、カタログ番号:066−05265)、セライト(和光純薬工業株式会社、カタログ番号:537−02305)を通して吸引濾過した。得られた濾液を濃縮して得た固体を、トルエンにて再結晶を行ったところ、目的の白色粉末を収量6.0g(18mmol)、収率45%で得た。ステップ1の合成スキームを下記式(a−1)に示す。
200mL三口フラスコに、ステップ1合成した6−ヨードベンゾ[b]ナフト[1,2−d]フランを6.0g(18mmol)と、2.4g(19mmol)のフェニルボロン酸と、70mLのトルエンと、20mLのエタノールと、22mLの炭酸カリウム水溶液(2.0mol/L)を入れた。この混合物を減圧しながら攪拌することで脱気をした。脱気後フラスコ内を窒素下としてから、480mg(0.42mmol)のテトラキス(トリフェニルホスフィン)パラジウム(0)を加えた。この混合物を窒素気流下、90℃で12時間攪拌した。所定時間経過後、この混合物に水を加え、水層をトルエンにより抽出した。得られた抽出液と有機層を合わせて、水で洗浄後、硫酸マグネシウムにより乾燥した。この混合物を自然濾過し、得られた濾液を濃縮して得た固体を、トルエンに溶かした。得られた溶液をセライト(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)、アルミナを通して吸引濾過した。得られたろ液を濃縮して得た固体を、トルエンにより再結晶を行ったところ、目的の白色固体を収量4.9g(17mmol)、収率93%で得た。ステップ2の合成スキームを下記式(b−1)に示す。
300mL三口フラスコに、ステップ2で合成した6−フェニルベンゾ[b]ナフト[1,2−d]フランを4.9g(17mmol)入れ、フラスコ内を窒素置換した後、87mLのテトラヒドロフラン(THF)を加えた。この溶液を−75℃に冷却してから、この溶液に11mL(18mmol)のn−ブチルリチウム(1.59mol/L n−ヘキサン溶液)を滴下して加えた。滴下後、得られた溶液を室温で1時間攪拌した。所定時間経過後、この溶液を−75℃に冷却してから、ヨウ素4.6g(18mmol)をTHF18mLに溶かした溶液を滴下して加えた。得られた溶液を室温に戻しながら17時間攪拌した。その後、この混合物にチオ硫酸ナトリウム水溶液を加え、1時間攪拌した後、この混合物の有機層を水で洗浄し、有機層を硫酸マグネシウムにより乾燥した。この混合物を自然濾過して得られたろ液をセライト(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)、アルミナを通して吸引濾過した。得られたろ液を濃縮して得た固体を、トルエンにより再結晶を行ったところ、目的の白色固体を収量3.7g(8.8mmol)、収率53%で得た。ステップ3の合成スキームを下記式(c−1)に示す。
200mL三口フラスコに、5.0g(12mmol)のステップ3で合成した8−ヨード−6−フェニルベンゾ[b]ナフト[1,2−d]フランと、2.9g(30mmol)のナトリウム tert−ブトキシドを加え、フラスコ内を窒素置換した後、60mLのトルエンと、1.4g(13mmol)のアニリンと、0.4mLのトリ(tert−ブチル)ホスフィンの10wt%ヘキサン溶液を加えた。この混合物を減圧脱気した後、窒素気流下で60℃にしてから、60mg(0.1mmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加えて、この混合物を60℃で40分撹拌した。撹拌後、得られた混合物を水、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。自然ろ過により硫酸マグネシウムを除去した後、得られたろ液を濃縮し、白色固体を得た。この固体をシリカゲルカラムクロマトグラフィー(展開溶媒は、トルエン:ヘキサン=1:2)により精製したところ、目的物の白色固体を3.5g、収率77%で得た。ステップ4の合成スキームを下記式(d−1)に示す。
1H NMR(クロロホルム−d,500MHz):δ=6.23(s、1H)、7.04(t、J=7.5Hz、1H)、7.24−7.26(m、2H)、7.34−7.41(m、4H)、7.47(t、J=8.0Hz、1H)、7.54−7.60(m、3H)、7.74(t、J=7.5Hz、1H)、7.95(d、J=6.5Hz、2H)、7.99(dd、J1=1.5Hz、J2=7.0Hz、1H)、8.03(s、1H)、8.08(d、J=8.0Hz、1H)、8.66(d、J=9.0Hz、1H)
200mL三口フラスコに、1.3g(5.0mmol)の4−ブロモビフェニルと、ステップ4で合成した6,N−ジフェニルベンゾ[b]ナフト[1,2−d]フラン−8−アミンを1.9g(5.0mmol)と、0.14g(0.30mmol)の2−ジシクロヘキシルホスフィノ−2’,4’,6’−トリイソプロピルビフェニル (略称:X−Phos)と、1.5g(15mmol)のナトリウム tert−ブトキシドを加え、フラスコ内を窒素置換した後、25mLのトルエンを加えた。この混合物を減圧脱気した後、窒素気流下で60℃にしてから、61mg(0.10mmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加え、この混合物を80℃で3時間撹拌した。撹拌後、得られた混合物を水、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで洗浄した。自然ろ過により硫酸マグネシウムを除去した後、得られたろ液を濃縮し、褐色固体を得た。この固体をシリカゲルカラムクロマトグラフィー(展開溶媒は、トルエン:ヘキサン=3:7)により精製したところ、目的物の淡黄色固体を2.0g、収率67%で得た。ステップ5の合成スキームを下記式(e−1)に示す。
本合成例では、実施の形態において構造式(146)として表された本発明の一態様の有機化合物、N,N−ビス(ビフェニル−4−イル)−6−フェニルベンゾ[b]ナフト[1,2−d]フラン−8−アミン(略称:BBABnf)の合成例を具体的に例示する。BBABnfの構造式を以下に示す。
合成例1のステップ1と同様に合成した。
合成例1のステップ2と同様に合成した。
合成例1のステップ3と同様に合成した。
200mL三口フラスコに、実施例1のステップ3で得られた8−ヨード−6−フェニルベンゾ[b]ナフト[1,2−d]フランを2.1g(5.0mmol)と、1.6g(5.0mmol)のジ(1,1’−ビフェニル−4−イル)アミンと、0.17g(0.40mmol)の2−ジシクロヘキシルホスフィノ−2’,6’−ジメトキシ−1,1’−ビフェニル(略称:S−Phos)と、0.97g(10mmol)のナトリウム tert−−ブトキシドを加え、フラスコ内を窒素置換した後、25mLのキシレンを加えた。この混合物を減圧脱気した後、窒素気流下で80℃にしてから、0.12g(0.20mmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加え、この混合物を80℃で5.5時間撹拌し、更に100℃で5時間撹拌した。撹拌後、得られた混合物を水、飽和食塩水で洗浄し、有機層を硫酸マグネシウムで洗浄した。自然ろ過により硫酸マグネシウムを除去した後、得られたろ液を濃縮し、褐色固体を得た。得られた個体をトルエンに溶かし、セライト(和光純薬工業株式会社、カタログ番号:537−02305)とアルミナを通しろ過した。得られたろ液を濃縮し、目的物の黄色固体を2.0g、収率67%で得た。ステップ4の合成スキームを下記式(d−2)に示す。
1H NMR(ジクロロメタン−d2,500MHz):δ=7.14−7.19(m、3H)、7.22(d、J=8.5Hz、4H)、7.29−7.33(m、3H)、7.41(t、J=8.0Hz、4H)、7.44−7.49(m、3H)、7.55−7.58(m、5H)、7.61(d、J=8.0Hz、4H)、7.74(t、J=8.0Hz、1H)、8.02(s、1H)、8.06(d、J=8.0Hz、1H)、8.26(d、1H)、8.67(d、J=8.0Hz、1H)
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。
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。
発光素子3は、発光素子2における第2の正孔輸送層112−2をBBABnfの代わりにN−(4−ビフェニル)−6,N−ジフェニルベンゾ[b]ナフト[1,2−d]フラン−8−アミン(略称:BnfABP)を用いて形成した他は発光素子2と同様に作製した。
本合成例では、実施の形態において構造式(229)として表された本発明の一態様の有機化合物、N,N−ビス(4−ビフェニル)ベンゾ[b]ナフト[1,2−d]フラン−6−アミン(略称:BBABnf(6))の合成例を具体的に例示する。BBABnf(6)の構造式を以下に示す。
6−ヨードベンゾ[b]ナフト[1,2−d]フランは、実施例1の合成例1におけるステップ1と同様に合成した。
200mL三口フラスコに、ステップ1で得られた6−ヨードベンゾ[b]ナフト[1,2−d]フランを2.7g(8.0mmol)と、2.6g(8.0mmol)のビス(1,1’−ビフェニル−4−イル)アミンと、0.19g(0.40mmol)の2−ジシクロヘキシルホスフィノ−2’、4’、6’−トリイソプロピルビフェニル(略称:X−Phos)と、1.5g(15mmol)のナトリウム tert−ブトキシドを加え、フラスコ内を窒素置換した後、40mLのキシレンをさらに加えた。この混合物を減圧脱気した後、窒素気流下で80℃にしてから、0.11g(0.20mmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加え、この混合物を120℃で3時間撹拌した後、更に140℃で6.5時間撹拌した。撹拌後、得られた混合物を水、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。自然ろ過により硫酸マグネシウムを除去した後、得られたろ液を濃縮し、褐色固体を得た。得られた固体を高速液体クロマトグラフィー(移動相:クロロホルム)にて精製したところ、目的物の淡黄色固体を3.4g、収率79%で得た。ステップ2の合成スキームを下記式(d−3)に示す。
1H NMR(クロロホルム−d,500MHz):δ=7.25(d、J=8.5Hz、4H)、7.31(t、J=7.5Hz、2H)、7.41−7.48(m、6H)、7.51−7.54(m、6H)、7.60(d、J=8.0Hz、4H)、7.67(t、J=7.5Hz、1H)、7.73(s、1H)、7.88(d、J=8.0Hz、1H)、8.42(d、J=7.0Hz、1H)、6.83(d、J=8.0Hz、1H)
本合成例では、実施の形態において構造式(189)として表された本発明の一態様の有機化合物、N,N−ビス(4−ビフェニル)ベンゾ[b]ナフト[1,2−d]フラン−8−アミン(略称:BBABnf(8))の合成例を具体的に例示する。BBABnf(8)の構造式を以下に示す。
200mL三口フラスコに、8−クロロベンゾ[b]ナフト[1,2−d]フランを2.0g(8.0mmol)と、2.6g(8.0mmol)のビス(1,1’−ビフェニル−4−イル)アミンと、0.19g(0.40mmol)の2−ジシクロヘキシルホスフィノ−2’、4’、6’−トリイソプロピルビフェニル(略称:X−Phos)と、1.5g(15mmol)のナトリウム tert−ブトキシドを加え、フラスコ内を窒素置換した後、40mLのキシレンを加えた。この混合物を減圧脱気した後、窒素気流下で80℃にしてから、0.11g(0.20mmol)のビス(ジベンジリデンアセトン)パラジウム(0)を加え、この混合物を120℃で3時間撹拌した後、更に140℃で6.5時間撹拌した。撹拌後、得られた混合物を120℃で加熱し、熱いままセライト(和光純薬工業株式会社、カタログ番号:537−02305)、フロリジール(和光純薬工業株式会社、カタログ番号:066−05265)、アルミナを通して濾過した。得られたろ液を濃縮したとところ、淡褐色固体を得た。得られた固体を高速液体クロマトグラフィー(移動相:クロロホルム)により精製したところ、目的物の淡黄色固体を2.9g、収率68%で得た。ステップ1の合成スキームを下記式(d−4)に示す。
1H NMR(クロロホルム−d,500MHz):δ=7.23(d、J=8.5Hz、4H)、7.31(t、J=7.5Hz、2H)、7.36(d、J=8.0Hz、1H)、7.42(t、J=8.0Hz、4H)、7.47(d、J=8.0Hz、1H)、7.52(d、J=9.0Hz、4H)、7.56(t、J=7.5Hz、1H)、7.59−7.61(m、5H)、7.74(t、J=8.5Hz、1H)、7.87(d、J=8.0Hz、1H)、8.01(d、J=8.0Hz、1H)、8.25(d、J=8.0Hz、1H)、8.65(d、J=8.0Hz、1H)
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。
発光素子5は、発光素子4における第2の正孔輸送層112−2をBBABnf(6)の代わりにN,N−ジ(4−ビフェニル)ベンゾ[b]ナフト[1,2−d]フラン−8−アミン(略称:BBABnf(8))を用いて形成した他は発光素子4と同様に作製した。
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。
発光素子7は、発光素子6における第2の正孔輸送層112−2をBBABnf(6)の代わりにN,N−ジ(4−ビフェニル)ベンゾ[b]ナフト[1,2−d]フラン−8−アミン(略称:BBABnf(8))を用いて形成した他は発光素子6と同様に作製した。
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。
102 陰極
103 EL層
111 正孔注入層
112 正孔輸送層
112−1 第1の正孔輸送層
112−2 第2の正孔輸送層
112−3 第3の正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
116 電荷発生層
117 P型層
118 電子リレー層
119 電子注入バッファ層
400 基板
401 陽極
403 EL層
404 陰極
405 シール材
406 シール材
407 封止基板
412 パッド
420 ICチップ
501 陽極
502 陰極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 駆動回路部(ソース線駆動回路)
602 画素部
603 駆動回路部(ゲート線駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用FET
612 電流制御用FET
613 陽極
614 絶縁物
616 EL層
617 陰極
618 発光素子
730 絶縁膜
770 平坦化絶縁膜
772 導電膜
782 発光素子
783 液滴吐出装置
784 液滴
785 層
786 EL層
788 導電膜
901 筐体
902 液晶層
903 バックライトユニット
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
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
1024W 陽極
1024R 陽極
1024G 陽極
1024B 陽極
1025 隔壁
1028 EL層
1029 陰極
1031 封止基板
1032 シール材
1033 透明な基材
1034R 赤色の着色層
1034G 緑色の着色層
1034B 青色の着色層
1035 ブラックマトリクス
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
1400 液滴吐出装置
1402 基板
1403 液滴吐出手段
1404 撮像手段
1405 ヘッド
1406 点線
1407 制御手段
1408 記憶媒体
1409 画像処理手段
1410 コンピュータ
1411 マーカー
1412 ヘッド
1413 材料供給源
1414 材料供給源
1415 材料供給源
1416 ヘッド
2001 筐体
2002 光源
3001 照明装置
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
7210 第2の表示部
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
7400 携帯電話機
9033 留め具
9034 スイッチ
9035 電源スイッチ
9036 スイッチ
9038 操作スイッチ
9310 携帯情報端末
9311 表示パネル
9312 表示領域
9313 ヒンジ
9315 筐体
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a タッチパネル領域
9632b タッチパネル領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9637 操作キー
9638 コンバータ
9639 ボタン
Claims (25)
- 一対の電極間に、下記式(G1)で表される有機化合物(ただし、P−88で表される化合物を除く)を有する発光素子。
(但し、式(G1)中、R1乃至R8はそれぞれ独立に、水素、炭素数1乃至6の炭化水素基、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。また、AおよびBはそのどちらか一方が下記式(g1)で表される基であり、他方が水素、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、炭素数1乃至6の炭化水素基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。)
(但し、式(g1)中、Ar1、Ar2はそれぞれ独立に、置換または無置換の炭素数6乃至60の芳香族炭化水素基(ただし、該芳香族炭化水素基が置換基を有する場合、該置換基がベンゾナフトフラン基で置換されたアミノ基である場合を除く)、下記式(g2)で表される基のいずれか一を表す。)
(但し、式(g2)中、R11乃至R18はそれぞれ独立に、水素、炭素数1乃至6の炭化水素基、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。また、Z1およびZ2のどちらか一方が式(g1)における窒素原子と結合しており、他方が水素、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、炭素数1乃至6の炭化水素基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。)
- 一対の電極間に、下記式(G1’)で表される有機化合物を有する発光素子。
(但し、式(G1’)中、R1乃至R8はそれぞれ独立に、水素、炭素数1乃至6の炭化水素基、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。また、AおよびBはそのどちらか一方が下記式(g1)で表される基であり、他方が水素、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、炭素数1乃至6の炭化水素基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。)
(但し、式(g1)中、Ar1、Ar2はそれぞれ独立に、置換または無置換の炭素数6乃至60の芳香族炭化水素基(ただし、該芳香族炭化水素基が置換基を有する場合、該置換基がジナフトチオフェン基、ベンゾナフトフラン基で置換されたアミノ基である場合を除く)、下記式(g2)で表される基のいずれか一を表す。)
(但し、式(g2)中、R11乃至R18はそれぞれ独立に、水素、炭素数1乃至6の炭化水素基、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。また、Z1およびZ2のどちらか一方が式(g1)における窒素原子と結合しており、他方が水素、炭素数3乃至6の環式炭化水素基、炭素数1乃至6のアルコキシ基、シアノ基、ハロゲン、炭素数1乃至6のハロアルキル基、炭素数1乃至6の炭化水素基、置換または無置換の炭素数6乃至60の芳香族炭化水素基のいずれか一を表す。) - 請求項1または請求項2において、
前記式(g1)で表される基が下記式(g3)で表される基である発光素子。
(但し、式(g3)において、Ar3、Ar4はそれぞれ独立に、置換または無置換の芳香族炭化水素基、置換または無置換のベンゾナフトフラニル基、置換または無置換のジナフトフラニル基のいずれか一を表す。また、Ar5、Ar6はそれぞれ独立に、置換または無置換の芳香族炭化水素基を表し、nおよびmはそれぞれ独立に、0または1を表す。なお、Ar3とAr5の炭素数を足した数と、Ar4とAr6の炭素数を足した数は各々60以下であるものとする。) - 請求項3において、
前記Ar3および前記Ar4がそれぞれ独立に、置換または無置換のフェニル基、置換または無置換のナフチル基、置換または無置換のアントラセニル基、置換または無置換のピレニル基のいずれか一である発光素子。 - 請求項3または請求項4において、
前記Ar5及び前記Ar6がそれぞれ独立に、置換または無置換のフェニレン基、置換または無置換のナフチレン基、置換または無置換のアントラセニレン基、置換または無置換のピレニレン基のいずれか一である発光素子。 - 請求項3乃至請求項5のいずれか一項において、
前記Ar3および前記Ar4がフェニル基である発光素子。 - 請求項3乃至請求項6のいずれか一項において、
前記nおよび前記mの少なくとも一方が1である場合、前記Ar5および前記Ar6がフェニレン基である発光素子。 - 請求項3乃至請求項7のいずれか一項において、
前記nおよび前記mの一方が1であり、他方が0である発光素子。 - 一対の電極間に、下記式で表される有機化合物を有する発光素子。
- 一対の電極間に、下記式で表される有機化合物を有する発光素子。
- 一対の電極間に、下記式で表される有機化合物を有する発光素子。
- 一対の電極間に、下記式で表される有機化合物を有する発光素子。
- 置換または無置換のアミン骨格を1つのみ有し、かつ、置換または無置換のベンゾナフトフラン骨格を有する有機化合物(ただし、ジベンゾチオフェン基またはジナフトチオフェン基またはベンゾナフトチオフェン基を有する場合を除く)を含む、正孔輸送層用材料。
- 第1の置換基、第2の置換基、第3の置換基を有するアミン骨格を1つのみ有する有機化合物を含み、
前記第1の置換基は、置換または無置換のベンゾナフトフラン骨格を有し、
前記第2の置換基および前記第3の置換基は、ジベンゾチオフェン基またはジナフトチオフェン基またはベンゾナフトチオフェン基を有さない、正孔輸送層用材料。 - 置換または無置換のアミン骨格を1つのみ有し、かつ、置換または無置換のベンゾナフトフラン骨格を有する有機化合物を含み、
前記アミン骨格の窒素は、前記ベンゾナフトフラン骨格と直接結合し、
前記アミン骨格の他の置換基は、ジベンゾチオフェン基またはジナフトチオフェン基またはベンゾナフトチオフェン基を有さない、正孔輸送層用材料。 - 請求項13乃至請求項15のいずれか一項において、
前記アミン骨格が前記ベンゾナフトフラン骨格の6位または8位に結合する正孔輸送層用材料。 - 請求項13乃至請求項16のいずれか一項に記載の正孔輸送層用材料を有する発光素子。
- 置換または無置換のアミン骨格を1つのみ有し、かつ、置換または無置換のベンゾナフトフラン骨格を有する有機化合物(ただし、ジベンゾチオフェン基またはジナフトチオフェン基またはベンゾナフトチオフェン基を有する場合を除く)を含む、発光素子用材料。
- 第1の置換基、第2の置換基、第3の置換基を有するアミン骨格を1つのみ有する有機化合物を含み、
前記第1の置換基は、置換または無置換のベンゾナフトフラン骨格を有し、
前記第2の置換基および前記第3の置換基は、ジベンゾチオフェン基またはジナフトチオフェン基またはベンゾナフトチオフェン基を有さない、発光素子用材料。 - 置換または無置換のアミン骨格を1つのみ有し、かつ、置換または無置換のベンゾナフトフラン骨格を有する有機化合物を含み、
前記アミン骨格の窒素は、前記ベンゾナフトフラン骨格と直接結合し、
前記アミン骨格の他の置換基は、ジベンゾチオフェン基またはジナフトチオフェン基またはベンゾナフトチオフェン基を有さない、発光素子用材料。 - 請求項18乃至請求項20のいずれか一項において、
前記アミン骨格が前記ベンゾナフトフラン骨格の6位または8位に結合する発光素子用材料。 - 請求項18乃至請求項21のいずれか一項に記載の発光素子用材料を有する発光素子。
- 請求項1乃至請求項12、請求項17、及び請求項22のいずれか一項に記載の発光素子と、トランジスタ、または基板と、を有する発光装置。
- 請求項23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23に記載の発光装置と、筐体と、を有する照明装置。
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