JP2016153400A - 有機化合物、発光素子、ディスプレイモジュール、照明モジュール、発光装置、表示装置、電子機器及び照明装置 - Google Patents
有機化合物、発光素子、ディスプレイモジュール、照明モジュール、発光装置、表示装置、電子機器及び照明装置 Download PDFInfo
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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
- 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
- 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
- 125000004957 naphthylene group Chemical group 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 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
- 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 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
- 239000012466 permeate Substances 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 229960000286 proflavine Drugs 0.000 description 1
- 230000002250 progressing effect Effects 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
- UWCCQBULRKZOAC-UHFFFAOYSA-N pyridine-2,3-dicarboximidamide Chemical compound NC(=N)C1=CC=CN=C1C(N)=N UWCCQBULRKZOAC-UHFFFAOYSA-N 0.000 description 1
- XNPMXMIWHVZGMJ-UHFFFAOYSA-N pyridine-2,6-dicarbonitrile Chemical compound N#CC1=CC=CC(C#N)=N1 XNPMXMIWHVZGMJ-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 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
- 239000002994 raw material Substances 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
- 230000007017 scission Effects 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
- 239000004332 silver Substances 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- 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
- 150000003568 thioethers Chemical class 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
- 238000012795 verification Methods 0.000 description 1
- 238000005406 washing 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
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- H—ELECTRICITY
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/649—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
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- Electroluminescent Light Sources (AREA)
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- Pyridine Compounds (AREA)
Abstract
【解決手段】式(G1)で示されるベンゾ[h]キナゾリン環を2つ又は3つ有する有機化合物化合物。
[置換基Aは芳香環又は複素芳香環を含むC3〜30の置換基;R1〜R7は夫々独立にH、C1〜6のアルキル基又は置換/無置換のC6〜13の芳香族炭化水素基;nは2又は3]
【選択図】なし
Description
本発明の一態様は、ベンゾ[h]キナゾリン環を2つまたは3つ有する有機化合物である。
まず、下記一般式(G0)で表されるアミジン誘導体を合成する。下記一般式(G0)で表されるアミジン誘導体は、以下のような簡便な合成スキーム(A)により合成できる。下記スキーム(A)では、原料であるアミジン誘導体(A1)と芳香族炭化水素のハロゲン化物(A2)とをカップリングすることにより、一般式(G0)で表されるアミジン誘導体が得られる。なお、合成スキーム(A)において、Qはハロゲンを表す。
続いて、一般式(G1)で表される有機化合物は、下記合成スキーム(B)のように簡便な合成スキームにより合成できる。下記スキーム(B)では、一般式(G0)で表されるアミジン誘導体とアルデヒド誘導体(A3)とを反応することにより、一般式(G1)で表される有機化合物が得られる。または、中間体(B1)を経由しても良い。中間体(B1)を経由する場合は、中間体(B1)と脱水素化剤を適当な溶媒中で反応させることにより、一般式(G1)で表される有機化合物が得られる。なお、脱水素化剤として、ベンゾキノン誘導体や硫黄などが挙げられる。
本実施の形態では実施の形態1で説明した有機化合物を用いた発光素子の詳細な構造の例について図1(A)を用いて以下に説明する。
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、実施の形態1に記載の本発明の一態様の有機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1に記載の有機化合物を含む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に記載の有機化合物を含む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に記載の有機化合物を含む発光素子は耐熱性が良好であり、耐熱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。また、また、実施の形態1に記載の有機化合物を含む発光素子を用いた発光装置はクロストークを抑制することが可能であるため、表示品質の良好な電子機器とすることが可能である。
本実施例では、実施の形態1で構造式(100)として示した2,2’−(ピリジン−2,6−ジイル)ビス(4−フェニルベンゾ[h]キナゾリン)(略称:2,6(P−Bqn)2Py)の合成方法について説明する。2,6(P−Bqn)2Pyの構造を以下に示す。
2,6−ピリジンジカルボニトリル15.4g(119mmol)、メタノール(脱水)250mLを500mL三口フラスコに入れ、混合した。この混合物にナトリウムメトキシド591mg(10.9mmol)を加え、窒素気流下、室温で16時間撹拌した。その後、塩化アンモニム12.7g(238mmol)を加え、窒素気流下、室温で2日間撹拌した。反応後、反応混合物を濃縮し、酢酸エチルを加えて超音波を照射して塊を粉砕し、吸引ろ過をして白色固体を25.5g、収率91%で得た。核磁気共鳴法(NMR)により得られた白色固体が2,6−ピリジンジカルボキサミジン2塩酸塩であることを確認した。ステップ1の合成スキームを下記式(a−1)に示す。
2,6−ピリジンジカルボキサミジン2塩酸塩11.6g(49.2mmol)、炭酸セシウム64.1g(197mmol)、ヨウ化銅0.937g(4.92mmol)を反応容器に入れ、フラスコ内を窒素置換した。この混合物にN,N−ジメチルホルムアミド100mL、1−ヨードナフタレン25.0g(98.4mmol)を入れ、フラスコ内を減圧しながら攪拌して脱気した後、窒素気流下、90℃で33時間加熱した。反応混合物を吸引ろ過した後、水とクロロホルムで残渣を洗浄し、先に得たろ液と洗浄液を合わせてろ液を得た。得られたろ液をクロロホルムで抽出した。得られた抽出溶液を水、飽和食塩水で洗浄し、無水硫酸マグネシウムを加えて乾燥させた。乾燥後の混合物を自然ろ過し、ろ液を濃縮して、黄緑色油状物を16.8g、収率82%で得た。EI−MS測定(Electron Impact−Mass Spectrometry)、核磁気共鳴法(NMR)により、得られた黄緑色油状物が中間体のN,N’−ジ(ナフタレン−1−イル)−2,6−ピリジンジカルボキサミジンであることを確認した。
ステップ2の合成スキームを下記式(b−1)に示す。
N,N’−ジ(ナフタレン−1−イル)−2,6−ピリジンジカルボキサミジン16.8g、ベンズアルデヒド25mLを500mLナスフラスコに入れ、窒素気流下、185℃で1.5時間加熱した。反応後の混合物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、トルエンと酢酸エチルをトルエン:酢酸エチル=5:1で混合した溶媒を用いた。目的物のフラクションを濃縮して得られた固体に酢酸エチルを加え、超音波を照射して塊を粉砕し、吸引ろ過をして黄色固体を得た。この黄色固体をトルエンで再結晶し、黄色固体を3.8g、収率13%で得た。NMRにより得られた黄色固体が目的物のジヒドロ体であることを確認した。このジヒドロ体2.0g(3.3mmol)、キシレン100mLを500mL三口フラスコに加えた。この混合物にp−クロラニル3.3g(13.2mmol)を加え、窒素気流下、160℃で8時間加熱した。反応混合物にトルエンを加え、セライト(和光純薬工業株式会社、カタログ番号:531−16855)を通して吸引ろ過した。得られたろ液を濃縮し、固体を得た。得られた固体にアセトンを加えて超音波を照射して塊を粉砕し、吸引ろ過をして固体を得た。得られた固体をトルエンで再結晶し、白色固体を1.4g、収率73%で得た。得られた白色固体1.4gをトレインサブリメーション法により圧力3.5×10−3Pa、300℃の条件で6時間加熱して、昇華精製を行った。昇華精製後、0.675g、回収率50%で白色固体を得た。ステップ3の合成スキームを下記式(c−1)に示す。
id Chromatography Mass Spectrometry,LC/MS分析を行った。
本実施例では、実施の形態1で構造式(101)として示した2,2’−(ピリジン−2,6−ジイル)ビス[4−(2−ナフチル)ベンゾ[h]キナゾリン](略称:2,6(N−Bqn)2Py)の合成方法について説明する。2,6(N−Bqn)2Pyの構造を以下に示す。
実施例1における合成例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。
N,N’−ジ(ナフタレン−1−イル)−2,6−ピリジンジカルボキサミジン0.93g、2−ナフトアルデヒド3.3g(21mmol)を300mLナスフラスコに入れ、窒素気流下、190℃で3時間加熱した。反応混合物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、まず、ジクロロメタンを用い、次いで、ジクロロメタン:酢酸エチル=5:1の混合溶媒を用い、次いで、ジクロロメタン:酢酸エチル=1:1の混合溶媒を用いた。得られた目的物のフラクションを濃縮して、黄色固体を得た。ステップ3の合成スキームを下記式(c−2)に示す。
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、第1の電極101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。ここで、第1の電極101は、発光素子の陽極として機能する電極である。
比較発光素子1は発光素子1の電子輸送層における2,6(P−Bqn)2Pyを上記構造式(v)で表される2,6(P2Pm)2Pyに変えた他は発光素子1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、第1の電極101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。ここで、第1の電極101は、発光素子の陽極として機能する電極である。
比較発光素子2は発光素子2の電子輸送層における2,6(P−Bqn)2Pyを2,6(P2Pm)2Pyに変えた他は発光素子2と同様に作製した。
本実施例では、実施の形態1で構造式(401)として示した2,2’−(2,2’−ビピリジン−6,6’−ジイル)ビス(4−フェニルベンゾ[h]キナゾリン)(略称:6,6’(P−Bqn)2BPy)の合成方法について説明する。6,6’(P−Bqn)2BPyの構造を以下に示す。
2,2’−ビピリジン−6,6’−ジカルボニトリル6.2g(30mmol)、メタノール(脱水)120mLを300mL三口フラスコに入れた。この混合物にナトリウムメトキシド149mg(2.8mmol)を加え、窒素気流下、室温で4日間撹拌した。その後、塩化アンモニム3.2g(60mmol)を加え、窒素気流下、室温で2日間撹拌し、反応させた。反応後、吸引ろ過をして固体を得た。得られた固体を酢酸エチルで洗浄し、白色固体を8.5g、収率90%で得た。核磁気共鳴法(NMR)により得られた白色固体が2,2’−ビピリジン−6,6’−ジカルボキサミジン2塩酸塩であることを確認した。ステップ1の合成スキームを下記式(a−3)に示す。
2,2’−ビピリジン−6,6’−ジカルボキサミジン2塩酸塩8.5g(27mmol)、炭酸セシウム35g(109mmol)、ヨウ化銅0.51g(2.7mmol)を反応容器に入れ、フラスコ内を窒素置換した。この混合物にN,N−ジメチルホルムアミド60mL、1−ヨードナフタレン14g(54mmol)、N,N−ジメチルエチレンジアミン0.48g(5.4mmol)を入れ、フラスコ内を減圧しながら攪拌して脱気後、窒素気流下、90℃で26時間加熱した。反応混合物を吸引ろ過し、水とクロロホルムでろ物を洗浄し、ろ液を得た。得られたろ液をクロロホルムで抽出した。得られた抽出溶液を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムを加えて乾燥させた。得られた混合物を自然ろ過し、ろ液を濃縮して、固体を得た。得られた固体にトルエンを加え、吸引ろ過をして黄色固体を4.3g、収率32%で得た。核磁気共鳴法(NMR)により得られた黄色固体がN,N’−ジ(ナフタレン−1−イル)−2,2’−ビピリジン−6,6’−ジカルボキサミジンであることを確認した。ステップ2の合成スキームを下記式(b−3)に示す。
N,N’−ジ(ナフタレン−1−イル)−2,2’−ビピリジン−6,6’−ジカルボキサミジン4.3g(8.7mmol)、ベンズアルデヒド9.2g(87mmol)を200mL三口フラスコに入れ、窒素気流下、180℃で1時間加熱した。反応後の混合物をシリカカラムクロマトグラフィーにより精製した。展開溶媒には、トルエン:酢酸エチル=10:1を用いた。得られたフラクションを濃縮して、得られた固体に酢酸エチルを加え、超音波を照射して塊を粉砕し、吸引ろ過をして黄色固体を2.4g、収率41%で得た。核磁気共鳴法(NMR)により得られた黄色固体が目的物のジヒドロ体であることを確認した。このジヒドロ体2.4g(3.6mmol)、キシレン360mLを1000mL三口フラスコに加えた。この混合物にp−クロラニル3.6g(14mmol)を加え、窒素気流下、160℃で5時間加熱した。反応混合物にトルエンを加えて吸引ろ過をして黄色固体を1.8g、収率75%で得た。得られた固体1.8gをトレインサブリメーション法により昇華精製し、1.3g、回収率72%で白色固体を得た。なお、昇華精製の条件は、圧力3.0×10−3Pa、330℃、17時間であった。ステップ3の合成スキームを下記式(c−3)に示す。
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、第1の電極101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。ここで、第1の電極101は、発光素子の陽極として機能する電極である。
比較発光素子3は発光素子3の電子輸送層114及び電子注入層115を、電子輸送層114として2,6(P−Bqn)2Pyを15nm、電子注入層115として上記構造式(vii)で表されるBPhenを10nm成膜した他は発光素子3と同様に作製した。
102 第2の電極
103 EL層
103_1 第1の発光ユニット
103_2 第2の発光ユニット
111 正孔注入層
111_1 第1の正孔注入層
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
113 発光層
113_1 第1の発光層
113_2 第2の発光層
114 電子輸送層
114_1 第1の電子輸送層
114_2 第2の電子輸送層
115 電子注入層
115_1 第1の電子注入層
115_2 第2の電子注入層
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 第1の電極
403 EL層
404 第2の電極
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 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 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
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 発光素子の第1の電極
1024R 発光素子の第1の電極
1024G 発光素子の第1の電極
1024B 発光素子の第1の電極
1025 隔壁
1028 EL層
1029 発光素子の第2の電極
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
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 (30)
- 下記一般式(G1)で表される有機化合物。
(但し、一般式(G1)中、置換基Aは芳香環又は複素芳香環を含む炭素数3乃至30の置換基を表す。また、R1乃至R7はそれぞれ独立に水素、炭素数1乃至6のアルキル基及び置換又は無置換の炭素数6乃至13の芳香族炭化水素基のいずれかを表し、nは2又は3である。) - 下記一般式(G2)で表される有機化合物。
(但し、一般式(G2)中、置換基Aは芳香環又は複素芳香環を含む炭素数3乃至30の置換基を表す。また、R1は水素、炭素数1乃至6のアルキル基及び置換又は無置換の炭素数6乃至13の芳香族炭化水素基のいずれかを表し、nは2又は3である。) - 請求項1又は請求項2において、前記nが2である有機化合物。
- 下記一般式(G3)で表される有機化合物。
(但し、一般式(G3)中、置換基Aは芳香環又は複素芳香環を含む炭素数3乃至30の置換基を表す。また、R1は水素、炭素数1乃至6のアルキル基及び炭素数6乃至13の芳香族炭化水素基のいずれかを表す。) - 請求項1乃至請求項4のいずれか一項において、前記置換基Aがベンゼン骨格を含む環又はピリジン骨格を一つ又は複数含む炭素数3乃至30の置換基である有機化合物。
- 請求項1乃至請求項5のいずれか1項において、前記置換基Aがベンゼン骨格を含む環又はピリジン骨格を一つ含む炭素数3乃至30の置換基である有機化合物。
- 請求項3乃至請求項6のいずれか一項において、前記置換基Aがフェニレン基又はピリジンジイル基である有機化合物。
- 下記一般式(G4)で表される有機化合物。
(但し、一般式(G4)中、R1は水素、炭素数1乃至6のアルキル基及び炭素数6乃至13の芳香族炭化水素基のいずれかを表す。) - 請求項1乃至請求項8のいずれか一項において、前記R1がフェニル基又はナフチル基である有機化合物。
- 請求項1乃至請求項9のいずれか一項に記載の有機化合物を含む発光素子。
- 請求項1乃至請求項9のいずれか一項に記載の有機化合物を電子輸送層に含む発光素子。
- 請求項1乃至請求項9のいずれか一項に記載の有機化合物を電子注入層に含む発光素子。
- 請求項1乃至請求項9のいずれか一項に記載の有機化合物を含むタンデム型発光素子。
- 請求項1乃至請求項9のいずれか一項に記載の有機化合物を電荷発生層の陽極側に接する層に含む発光素子。
- 陽極と、
陰極と、
前記陽極と前記陰極との間に挟まれたEL層とを有し、
前記EL層は各々異なる機能を有する複数の層状の領域を有し、
前記陰極と接する前記層状の領域にベンゾ[h]キナゾリン環を2つまたは3つ有する有機化合物を含む発光素子。 - 陽極と、
陰極と、
前記陽極と前記陰極との間に挟まれたEL層とを有し、
前記EL層は少なくとも発光層と電子注入層とを有し、
前記電子注入層にベンゾ[h]キナゾリン骨格を2つまたは3つ有する有機化合物を含む発光素子。 - 陽極と、
陰極と、
前記陽極と前記陰極との間に挟まれたEL層とを有し、
前記EL層は少なくとも発光層と電荷発生層とを有し、
前記電荷発生層にベンゾ[h]キナゾリン骨格を2つまたは3つ有する有機化合物を含む発光素子。 - 陽極と、
陰極と、
前記陽極と前記陰極との間に挟まれたEL層とを有し、
前記EL層は少なくとも発光層と電子輸送層とを有し、
前記電子輸送層にベンゾ[h]キナゾリン骨格を2つまたは3つ有する有機化合物を含む発光素子。 - 請求項16乃至請求項18のいずれか一項において、
前記有機化合物は、炭素数3乃至30の芳香環又は複素芳香環を含む置換基にベンゾ[h]キナゾリン骨格が2つまたは3つ結合した有機化合物である発光素子。 - 請求項16乃至請求項18のいずれか一項において、
前記有機化合物は、炭素数3乃至30の複素芳香環を含む置換基にベンゾ[h]キナゾリン骨格が2つまたは3つ結合した有機化合物である発光素子。 - 請求項16乃至請求項18のいずれか一項において、
前記有機化合物は、ピリジン環にベンゾ[h]キナゾリン骨格が2つまたは3つ結合した有機化合物である発光素子。 - 請求項16乃至請求項18のいずれか一項において、
前記有機化合物は、ピリジン環にベンゾ[h]キナゾリン骨格が2つ結合した有機化合物である発光素子。 - 請求項22において、
前記ピリジン環の置換位置は2位および6位である発光素子。 - 請求項19乃至請求項23のいずれか一項において、
前記ベンゾ[h]キナゾリン骨格の置換位置は2位である発光素子。 - 請求項10乃至請求項20のいずれか一項に記載の発光素子を含むディスプレイモジュール。
- 請求項10乃至請求項20のいずれか一項に記載の発光素子を含む照明モジュール。
- 請求項10乃至請求項20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10乃至請求項20のいずれか一項に記載の発光素子を表示部に有し、前記発光素子を制御する手段を備えた表示装置。
- 請求項10乃至請求項20のいずれか一項に記載の発光素子を照明部に有し、前記発光素子を制御する手段を備えた照明装置。
- 請求項10乃至請求項20のいずれか一項に記載の発光素子を有する電子機器。
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CN116018040A (zh) | 2023-04-25 |
US20160240794A1 (en) | 2016-08-18 |
WO2016132250A1 (en) | 2016-08-25 |
CN107250131A (zh) | 2017-10-13 |
TWI696616B (zh) | 2020-06-21 |
JP6664231B2 (ja) | 2020-03-13 |
JP6887539B2 (ja) | 2021-06-16 |
KR20230088859A (ko) | 2023-06-20 |
KR20170117084A (ko) | 2017-10-20 |
JP2020094056A (ja) | 2020-06-18 |
TW201638082A (zh) | 2016-11-01 |
US10476009B2 (en) | 2019-11-12 |
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