JP7292206B2 - 有機化合物、発光素子、発光装置、電子機器および照明装置 - Google Patents
有機化合物、発光素子、発光装置、電子機器および照明装置 Download PDFInfo
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- JP7292206B2 JP7292206B2 JP2019532222A JP2019532222A JP7292206B2 JP 7292206 B2 JP7292206 B2 JP 7292206B2 JP 2019532222 A JP2019532222 A JP 2019532222A JP 2019532222 A JP2019532222 A JP 2019532222A JP 7292206 B2 JP7292206 B2 JP 7292206B2
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 238000000967 suction filtration 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
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000004808 supercritical fluid chromatography Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 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
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-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
- 238000002411 thermogravimetry Methods 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
- 125000005580 triphenylene group Chemical group 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
- 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
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical class [S-2].[Zn+2] DRDVZXDWVBGGMH-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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
-
- 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
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/631—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
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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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
- H10K50/15—Hole transporting layers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
本発明の一態様の有機化合物は、下記一般式(G1)または一般式(G2)で表される有機化合物である。
本発明の一般式(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(G2-a)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。
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2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。
300mL三つ口フラスコへ8.9g(40mmol)の3-ブロモ-2-ナフトールと、10g(60mmol)の5-クロロ-2-フルオロフェニルボロン酸と、0.24g(0.080mmol)のトリ(オルト-トリル)ホスフィンと、40mLの炭酸カリウム水溶液(2.0mmol/L)と、トルエン120mL、エタノール50mLをいれ、混合した。この混合物の減圧脱気をした後、フラスコ内を窒素置換した。この混合物を60℃に加熱してから、90mg(40μmol)の酢酸パラジウム(II)を加え、80℃で8時間撹拌した。撹拌後、この混合物にさらに5.8g(35mmol)の5-クロロ-2-フルオロフェニルボロン酸と、90mg(40μmol)の酢酸パラジウム(II)を加え、80℃で8時間撹拌した。攪拌後、室温まで冷却し、得られた混合物を水と飽和食塩水で洗浄し、水層と有機層を分離した後、有機層を硫酸マグネシウムで乾燥した。この混合物を自然濾過し、ろ液を濃縮して乾燥させた。乾燥後、黒色固体を7.6g得た。ステップ1の合成スキームを以下に示す。
500mLナスフラスコに、ステップ1で得られた7.6gの黒色固体と、7.6g(55mmol)の炭酸カリウムと、110mLのN-メチル-2-ピロリドン(略称:NMP)を入れ、120℃で7時間撹拌した。得られた混合物を吸引ろ過し、炭酸カリウムを除去した。得られたろ液に2mol/Lの塩酸を10mL加えてろ液を中和したところ、白色沈殿が生じた。この白色沈殿を吸引ろ過で回収し、酢酸エチル、水、エタノールで洗浄したところ、白色固体を3.5g、ステップ1とステップ2を併せた収率として34%で得た。ステップ2の合成スキームを以下に示す。
還流管を付けた300mL三口フラスコに、2.0g(8.0mmol)の2-クロロベンゾ[b]ナフト[2,3-d]フランと、2.6g(8.0mmol)のビス(4-ビフェニリル)アミンと、56mg(0.16mmol)のジ-tert-ブチル(1-メチル-2,2-ジフェニルシクロプロピル)ホスフィン(商品名:cBRIDP(登録商標))と、1.5g(16mmol)ナトリウム tert-ブトキシドと、トルエン100mLを入れ、この混合物を減圧脱気し、フラスコ内を窒素置換してから、ビス(ベンジリデンアセトン)パラジウム46mg(80μmol)を加えた。この混合物を、110℃で13時間撹拌した。撹拌後、得られた混合物に水を加え、水層と有機層を分離してから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併せて水と飽和食塩水で洗浄し、硫酸マグネシウムにより乾燥させた。この混合物をろ過し得られたろ液を濃縮したところ、褐色固体を3.7g、収率86%で得た。ステップ3の合成スキームを以下に示す。
300mL三つ口フラスコへ7.5g(34mmol)の3-ブロモ-2-ナフトールと、5.9g(34mmol)の3-クロロ-2-フルオロフェニルボロン酸と、0.21g(67μmol)のトリ(オルト-トリル)ホスフィンと、30mLの炭酸カリウム水溶液(2.0mol/L)、トルエン110mL、エタノール30mLをいれ、混合物の減圧脱気をした後、フラスコ内を窒素置換した。この混合物を60℃に加熱した後、76mg(34μmol)の酢酸パラジウム(II)を加え、80℃で8時間撹拌した。撹拌後、さらに3.0g(17mmol)の3-クロロ-2-フルオロフェニルボロン酸と、36mg(16μmol)の酢酸パラジウム(II)を加え、80℃で8時間撹拌した。攪拌後、室温まで冷却し、得られた混合物を水と飽和食塩水で洗浄し、水層と有機層を分離してから、有機層を硫酸マグネシウムで乾燥した。この混合物を自然濾過し、ろ液を濃縮して乾燥させた。乾燥後、黒色固体を6.1g得た。ステップ1の合成スキームを以下に示す。
500mLナスフラスコに、ステップ1で得られた黒色固体6.1gと、6.3g(44mmol)の炭酸カリウムと、110mLのN-メチル-2-ピロリドン(NMP)を入れ、120℃で7時間撹拌した。得られた混合物を吸引ろ過し、炭酸カリウムを除去した。得られたろ液に2.0mol/Lの塩酸を10mL加えて中和した。この混合物に水を加え、有機層と水層を分離してから、水層を酢酸エチルにて抽出した。得られた抽出液と有機層を合わせて水と飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。この混合物を自然濾過し得られたろ液を濃縮したところ、褐色固体4.9gを得た。この褐色固体を、超臨界流体クロマトグラフィー(SFC)(移動相:液体二酸化炭素:テトラヒドロフラン=7:3)にて精製したところ、目的物の淡黄色固体を2.2g、ステップ1とステップ2を併せた収率として26%で得た。ステップ2の合成スキームを以下に示す。
還流管を付けた300mL三口フラスコに、1.5g(6.0mmol)の4-クロロベンゾ[b]ナフト[2,3-d]フランと、1.9g(6.0mmol)のビス(4-ビフェニリル)アミンと、42mg(0.12mmol)のジ-tert-ブチル(1-メチル-2,2-ジフェニルシクロプロピル)ホスフィン(cBRIDP(登録商標))と、1.2g(12mmol)ナトリウム tert-ブトキシドと、トルエン90mLを入れ、減圧脱気をしたあとにフラスコ内を窒素置換した。この混合物へ、ビス(ベンジリデンアセトン)パラジウム34mg(60μmol)を加えた後、110℃で6時間撹拌した。得られた混合物に水を加え、水層と有機層を分離した後、水層をトルエンにて抽出した。得られた抽出液と有機層を併せて水と飽和食塩水で洗浄し、硫酸マグネシウムにより乾燥させた。この混合物を自然濾過し、得られたろ液を濃縮したところ、目的物の褐色固体を2.7g、収率83%で得た。
ステップ3の合成スキームを以下に示す。
200mL三口フラスコに、2.9g(20mmol)の1-ナフトールと、13g(40mmol)の炭酸カリウムを加え、フラスコ内を窒素置換した。この混合物へ、110mLのN-メチルピロリドンン(NMP)と、7.5g(40mmol)の1-ブロモ-2-フルオロベンゼンを加え、この混合物を170℃で4時間撹拌した。撹拌後、得られた混合物へ100mLの2mol/Lの塩酸を加えて室温で撹拌した。撹拌後この混合物の有機層を100mLの2mol/Lの塩酸で2回洗浄し、水層をトルエンで2回抽出した。抽出溶液と有機層を併せてから100mLの2mol/Lの塩酸と飽和食塩水を用いて洗浄し、得られた有機層へ硫酸マグネシウムを加えて乾燥した。この混合物を自然濾過し、得られたろ液を濃縮し褐色の化合物を得た。この化合物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=1:1)で精製したところ、目的物の無色透明油状物を4.1g、収率69%で得た。ステップ1の合成スキームを以下に示す。
500mLナスフラスコに、4.1g(14mmol)の2-ブロモフェニル-1-ナフチルエーテルと、0.20mg(0.40mmol)のトリフェニルホスフィンと、10g(30mmol)の炭酸セシウムを加え、フラスコ内を窒素置換した。この混合物へ100mLのNMPを加えたのち、この混合物を減圧脱気した。この混合物へ、89mg(0.40mmol)の酢酸パラジウム(II)を加えてから、窒素気流下、180℃で3時間半攪拌した。撹拌後、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、2mol/Lの塩酸と、飽和炭酸ナトリウム水溶液と、飽和食塩水で洗浄後、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たところ、目的物の淡褐色固体を3.0g、収率99%で得た。ステップ2の合成スキームを以下に示す。
200mL三口フラスコに、3.0g(14mmol)のベンゾ[b]ナフト[2,1-d]フランを加え、フラスコ内を窒素置換した後、70mL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8.5mL(14mmol)のn-ブチルリチウム(1.64mol/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。撹拌後、この溶液を-75℃に冷却してから、ヨウ素3.6g(14mmol)をTHF10mL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。撹拌後、得られた溶液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、水層を酢酸エチルで抽出した。抽出液と有機層を合わせて、飽和食塩水で洗浄し、得られた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、得られた溶液を濃縮したところ、目的の白色固体を収量4.4g、収率93%で得た。ステップ3の合成スキームを以下に示す。
1H NMR(クロロホルム-d,500MHz):δ=7.16(t,J=7.8Hz,1H),7.59(td,J1=7.5Hz,J2=1.5Hz,1H),7.67(td,J1=7.5Hz,J2=1.0Hz,1H),7.80(d,J=8.5Hz,1H),7.83(dd,J1=8.0Hz,J2=1.5Hz,1H),7.94-7.96(m,2H),7.99(d,J=8.0Hz,1H),8.53(d,J=8.5Hz,1H)
還流管を付けた200mL三口フラスコに、2.0g(6.0mmol)の10-ヨードベンゾ[b]ナフト[2,1-d]フランと、1.9g(6.0mmol)のビス(4-ビフェニリル)アミンと、42mg(0.12mmol)のジ-tert-ブチル(1-メチル-2,2-ジフェニルシクロプロピル)ホスフィン(cBRIDP(登録商標))と、1.2g(12mmol)ナトリウム tert-ブトキシドと、トルエン70mLを入れ、この混合物を減圧脱気した後、フラスコ内を窒素置換した。ビス(ベンジリデンアセトン)パラジウム34mg(0.060mmol)を加えた後、110℃で10時間撹拌した。撹拌後、得られた混合物へ水を加え、水層をトルエンにて抽出した。有機層と得られた抽出液を併せて水と飽和食塩水で洗浄し、硫酸マグネシウムにより乾燥させた。この混合物を自然濾過し、得られたろ液を濃縮した。得られた粗生成物を、シリカゲルクロマトグラフィー(移動相はヘキサン:トルエン=5:1)により精製したところ、目的物の褐色固体を0.75g、収率23%で得た。ステップ4の合成スキームを以下に示す。
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70nmとし、電極面積は2mm×2mmとした。
発光素子2は電子輸送層114を、上記構造式(vii)で表される2-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]ジベンゾ[f,h]キノキサリン(略称:2mDBTBPDBq-II)を15nmとなるように蒸着した後、NBPhenを膜厚10nmとなるように蒸着し形成した他は、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70nmとし、電極面積は2mm×2mmとした。
発光素子4は電子輸送層114を、上記構造式(vii)で表される2-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]ジベンゾ[f,h]キノキサリン(略称:2mDBTBPDBq-II)を15nmとなるように蒸着した後、NBPhenを膜厚10nmとなるように蒸着し形成した他は、発光素子3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70nmとし、電極面積は2mm×2mmとした。
発光素子6はPCPPnを膜厚30nmとなるように蒸着し正孔輸送層112を形成した他は、発光素子5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、第1の電極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、第1の電極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10は電子輸送層114を、上記構造式(vii)で表される2-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]ジベンゾ[f,h]キノキサリン(略称:2mDBTBPDBq-II)を15nmとなるように蒸着した後、NBPhenを膜厚10nmとなるように蒸着し形成した他は、発光素子9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70nmとし、電極面積は2mm×2mmとした。
発光素子12は電子輸送層114を、上記構造式(vii)で表される2-[3’-(ジベンゾチオフェン-4-イル)ビフェニル-3-イル]ジベンゾ[f,h]キノキサリン(略称:2mDBTBPDBq-II)を15nmとなるように蒸着した後、NBPhenを膜厚10nmとなるように蒸着し形成した他は、発光素子11と同様に作製した。
Claims (15)
- 下記一般式(G1)で表される有機化合物。
(但し、一般式(G1)中、R1乃至R10は一つが下記一般式(g1)で表される基であり、残り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、フッ素、炭素数1乃至6のハロアルキル基および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、一般式(g1)において、Ar3、Ar4はそれぞれ独立に、置換または無置換の炭素数6乃至10の芳香族炭化水素基および下記一般式(g2)乃至下記一般式(g4)で表される基のいずれか一を表す。また、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10の2価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乃至2の整数を表すが、Ar3が下記一般式(g4)で表される基である場合にはnは1または2であり、Ar4が下記一般式(g4)で表される基である場合にはmは1または2であるものとする。なお、nが2の場合、二つのAr1はそれぞれ異なっていても同じであっても良く、また、mが2の場合、2つのAr2はそれぞれ異なっていても同じであっても良い。また、Ar3、Ar4が炭素数6乃至10の芳香族炭化水素基であって置換基を有する場合、当該置換基は炭素数6乃至10の芳香族炭化水素基、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、フッ素、炭素数1乃至6のハロアルキル基および下記一般式(g2)乃至(g4)で表される基のいずれか一または複数である。なお、nおよびmが0であり、Ar3およびAr4がフェニル基であり、当該フェニル基の2位および6位が芳香族炭化水素基で置換されている構成は除くものとする。)
(但し、一般式(g2)中、R31乃至R40はその1つが単結合を表し、上記一般式(g1)における窒素原子、Ar3またはAr4に結合する。残り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、ハロゲンおよび炭素数1乃至6のハロアルキル基のいずれか一を表す。
また、一般式(g3)中、R41乃至R50はその1つが単結合を表し、上記一般式(g1)における窒素原子、Ar3またはAr4に結合する。残り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、および炭素数1乃至6のハロアルキル基のいずれか一を表す。
また、一般式(g4)中、R51乃至R60はその1つが単結合を表し、上記一般式(g1)におけるAr3またはAr4に結合する。残り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、ハロゲンおよび炭素数1乃至6のハロアルキル基のいずれか一を表す。) - 請求項1において、
前記一般式(g1)で表される基が前記一般式(G1)で表される有機化合物におけるR7乃至R10のいずれか一に結合する有機化合物。 - 請求項1において、
前記一般式(g1)で表される基が前記一般式(G1)で表される有機化合物におけるR1、R8およびR10のいずれか一に結合する有機化合物。 - 下記一般式(G2)で表される有機化合物。
(但し、一般式(G2)中、R17乃至R20は一つが下記一般式(g1)で表される基であり、残り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、フッ素、炭素数1乃至6のハロアルキル基および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。R11乃至R16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、フッ素、炭素数1乃至6のハロアルキル基および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、一般式(g1)において、Ar3、Ar4はそれぞれ独立に、置換または無置換の炭素数6乃至10の芳香族炭化水素基および下記一般式(g2)乃至下記一般式(g4)で表される基のいずれか一を表す。また、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10の2価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乃至2の整数を表すが、Ar3が下記一般式(g4)で表される基である場合にはnは1または2であり、Ar4が下記一般式(g4)で表される基である場合にはmは1または2であるものとする。なお、nが2の場合、二つのAr1はそれぞれ異なっていても同じであっても良く、また、mが2の場合、2つのAr2はそれぞれ異なっていても同じであっても良い。また、Ar3、Ar4が炭素数6乃至10の芳香族炭化水素基であって置換基を有する場合、当該置換基は炭素数6乃至10の芳香族炭化水素基、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、フッ素、炭素数1乃至6のハロアルキル基および下記一般式(g2)乃至(g4)で表される基のいずれか一または複数である。
ただし、一般式(g1)が[1,1’:3’,1’’-ターフェニル]-2’-アミノ基を有する場合を除く。)
(但し、一般式(g2)中、R31乃至R40はその1つが単結合を表し、上記一般式(g1)における窒素原子、Ar3またはAr4に結合する。残り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、ハロゲンおよび炭素数1乃至6のハロアルキル基のいずれか一を表す。
また、一般式(g3)中、R41乃至R50はその1つが単結合を表し、上記一般式(g1)における窒素原子、Ar3またはAr4に結合する。残り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、および炭素数1乃至6のハロアルキル基のいずれか一を表す。
また、一般式(g4)中、R51乃至R60はその1つが単結合を表し、上記一般式(g1)におけるAr3またはAr4に結合する。残り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、ハロゲンおよび炭素数1乃至6のハロアルキル基のいずれか一を表す。) - 請求項4において、
前記一般式(g1)で表される基が前記一般式(G2)で表される有機化合物におけるR18またはR20に結合する有機化合物。 - 請求項1乃至請求項5のいずれか一項おいて、
前記nおよび前記mは、それぞれ独立に1または2である有機化合物。 - 請求項1乃至請求項6のいずれか一項において、
前記Ar3およびAr4がそれぞれ独立に置換又は無置換の炭素数6乃至10の芳香族炭化水素基である有機化合物。 - 請求項1乃至請求項7のいずれか一項において、
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のいずれか一である有機化合物。 - 請求項1乃至請求項8のいずれか一項において、
前記Ar1および前記Ar2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のいずれか一項において、
前記nおよび前記mが2である有機化合物。 - 請求項1乃至請求項10のいずれか一項において、
前記nおよび前記mが1である有機化合物。 - 陽極と陰極との間に請求項1乃至請求項11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12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13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13に記載の発光装置と、
筐体と、
を有する照明装置。
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