JP7282737B2 - 正孔輸送層用材料、発光素子、発光装置、電子機器および照明装置 - Google Patents
正孔輸送層用材料、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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Images
Classifications
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S2/00—Systems of lighting devices, not provided for in main groups F21S4/00 - F21S10/00 or F21S19/00, e.g. of modular construction
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
- F21S6/00—Lighting devices intended to be free-standing
-
- 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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- Indole Compounds (AREA)
Description
本発明の一態様は、ベンゾカルバゾール骨格、ジベンゾカルバゾール骨格またはトリベンゾカルバゾール骨格のいずれか一と、カルバゾール骨格、ベンゾカルバゾール骨格およびジベンゾカルバゾール骨格またはトリベンゾカルバゾール骨格のいずれか一が、ナフタレン-1,4-ジイル基またはナフタレン-1,5-ジイル基で結合する有機化合物である。これらの骨格または基は各々置換基を有していても良い。
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2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2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2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。
本実施例では、本発明の一態様の有機化合物である8,8’-(ナフタレン-1,4-ジイル)ビス(11-フェニル-11H-ベンゾ[a]カルバゾール)(略称:PaBC2N)の合成方法について詳しく説明する。PaBC2Nの構造式を以下に示す。
本実施例では、本発明の一態様の有機化合物である12,12’-(ナフタレン-1,4-ジイル)ビス(9-フェニル-9H-ジベンゾ[a,c]カルバゾール)(略称:PacDBC2N)の合成方法について詳しく説明する。PacDBC2Nの構造式を以下に示す。
得られたトルエン溶液の吸収スペクトルおよび発光スペクトルの測定結果を図18に示す。横軸は波長、縦軸は吸収強度および発光強度を表す。また、固体薄膜の吸収スペクトルおよび発光スペクトルの測定結果を図19に示す。
本実施例では、本発明の一態様の有機化合物である10,10’-(ナフタレン-1,4-ジイル)ビス(7-フェニルベンゾ[c]カルバゾール)(略称:PcBC2N)の合成方法について詳しく説明する。PcBC2Nの構造式を以下に示す。
本実施例では、本発明の一態様の有機化合物である11-フェニル-8-[4-(9-フェニルカルバゾール-3-イル)-1-ナフチル]ベンゾ[a]カルバゾール(略称:PCNPaBC)の合成方法について詳しく説明する。PCNPaBCの構造式を以下に示す。
本実施例では、本発明の一態様の有機化合物である7-フェニル-10-[4-(9-フェニルカルバゾール-3-イル)-1-ナフチル]ベンゾ[c]カルバゾール(略称:PCNPcBC)の合成方法について詳しく説明する。PCNPcBCの構造式を以下に示す。
200mLの3口フラスコに3-(4-ブロモ-1-ナフチル)-9-フェニル-9H-カルバゾール2.0g(4.5mmol)、2-(ベンゾ[c]カルバゾール-10-イル)-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン1.9g(5.4mmol)、トリス(2-メチルフェニル)ホスフィン0.28g(0.91mmol)、炭酸カリウム1.5g(11mmol)、トルエン45mL、エタノール6mL、水6mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物に酢酸パラジウム(II)0.070g(0.31mmol)を加え、窒素気流下、80℃で6時間、90℃で8時間撹拌した。撹拌後、有機層と水層を分離してから水層をトルエンで抽出した。得られた抽出溶媒と有機層を合わせ、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して油状物質を得た。得られた油状物質をシリカゲルクロマトグラフィー(トルエン:ヘキサン=11:9)で精製し、さらに酢酸エチルとメタノールの混合溶媒で再結晶したところ、目的物の白色固体を収量2.0g、収率76%で得た。ステップ1の合成スキームを以下に示す。
100mLの3口フラスコに10-[4-(9-フェニルカルバゾール-3-イル)-1-ナフチル]ベンゾ[c]カルバゾール2.0g(3.3mmol)、ヨードベンゼン0.75mL(6.7mmol)、ナトリウムtert-ブトキシド0.68g(7.0mmol)、キシレン17mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物にトリtert-ブチルホスフィン10wt%ヘキサン溶液0.40mL(0.13mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)0.074g(0.13mmol)を加え、窒素気流下、150℃で14時間撹拌した。撹拌後、得られた混合物に水を加え、有機層と水層を分離した後、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して油状物質を得た。得られた油状物質をシリカゲルクロマトグラフィー(トルエン:ヘキサン=1:2)で精製し、さらに酢酸エチルとメタノールの混合溶媒で再結晶したところ、目的物の白色固体を1.8g、収率84%で得た。ステップ2の合成スキームを以下に示す。
本実施例では、本発明の一態様の有機化合物である7-フェニル-10-[5-(9-フェニルカルバゾール-3-イル)-1-ナフチル]ベンゾ[c]カルバゾール(略称:1,5PCNPcBC)の合成方法について詳しく説明する。1,5PCNPcBCの構造式を以下に示す。
300mLの3口フラスコに3-(5-ブロモ-1-ナフチル)-9-フェニルカルバゾール2.0g(4.4mmol)、2-(ベンゾ[c]カルバゾール-10-イル)-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン1.8g(5.2mmol)、トリス(2-メチルフェニル)ホスフィン0.13g(0.44mmol)、炭酸カリウム1.5g(11mmol)、トルエン43mL、エタノール5mL、水5mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物に酢酸パラジウム(II)0.036g(0.16mmol)を加え、窒素気流下、100℃で11時間撹拌した。撹拌後、得られた混合物の水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、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。得られた混合物を自然濾過し、濾液を濃縮して油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィー(トルエン)で精製し、さらに酢酸エチルとメタノールの混合溶媒で再結晶したところ、目的物の白色固体を2.0g、収率80%で得た。ステップ1の合成スキームを以下に示す。
100mLの3口フラスコに10-[5-(9-フェニルカルバゾール-3-イル)-1-ナフチル]ベンゾ[c]カルバゾール2.0g(3.5mmol)、ヨードベンゼン0.80mL(7.1mmol)、ナトリウムtert-ブトキシド0.68g(7.1mmol)、キシレン18mLを加えた。この混合物を減圧下で撹拌することで脱気し、フラスコ内を窒素置換した。この混合物にトリ-tert-ブチルホスフィン10wt%ヘキサン溶液0.30mL(0.098mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)0.043g(0.075mmol)を加え、窒素気流下、150℃で7時間撹拌した。撹拌後、得られた混合物に水を加え、有機層と水層を分離した後、水層をトルエンで抽出した。得られた抽出溶液と有機層を合わせ、飽和食塩水で洗浄し、硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して、油状物質を得た。得られた油状物質をシリカゲルカラムクロマトグラフィー(トルエン:ヘキサン=1:1)で精製し、さらに酢酸エチルとメタノールとの混合溶媒と、トルエンとヘキサンの混合溶媒で2回再結晶したところ、目的物の白色固体を収量1.9g、収率84%で得た。ステップ2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、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子1は、発光素子1における正孔注入層111および正孔輸送層112に用いたPaBC2N)を上記構造式(vi)で表される3,3’-(ナフタレン-1,4-ジイル)ビス(9-フェニル-9H-カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子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、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子2は、発光素子2における正孔注入層111および正孔輸送層112に用いたPcBC2Nを上記構造式(vi)で表される3,3’-(ナフタレン-1,4-ジイル)ビス(9-フェニル-9H-カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子2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4mm2(2mm×2mm)とした。
比較発光素子3は、発光素子3における正孔注入層111および正孔輸送層112に用いたPCNPaBCを上記構造式(vi)で表される3,3’-(ナフタレン-1,4-ジイル)ビス(9-フェニル-9H-カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子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、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
比較発光素子4は、発光素子4における正孔注入層111および正孔輸送層112に用いたPCNPcBCを上記構造式(vi)で表される3,3’-(ナフタレン-1,4-ジイル)ビス(9-フェニル-9H-カルバゾール)(略称:PCzN2)に変えて作製した他は発光素子4と同様に作製した。
本実施例では、本発明の一態様の有機化合物である2,2’-(ナフタレン-1,4-ジイル)ビス(5-フェニル-5H-ベンゾ[b]カルバゾール)(略称:PbBC2N)の合成方法について詳しく説明する。PbBC2Nの構造式を以下に示す。
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、陽極101を形成した。なお、その膜厚は70nmとし、電極面積は4mm2(2mm×2mm)とした。
Claims (13)
- 式(G1)で表される正孔輸送層用材料。
(式(G1)において、Lは置換もしくは無置換のナフタレン-1,4-ジイル基または置換もしくは無置換のナフタレン-1,5-ジイル基を表す。また、AとBは同一の構造を有し、Aは式(gA)で表される基を表す。)
(式(gA)において、Ar1は環を形成する炭素原子の数が6乃至13の置換または無置換のアリール基を表す。また、R1乃至R7のうち、R1およびR2、R4およびR5、R5およびR6、並びにR6およびR7は、その少なくとも一つの組み合わせにおいて縮合してベンゼン環を形成し、残りはそれぞれ独立に水素、炭素原子数1乃至6のアルキル基、炭素原子数3乃至6のシクロアルキル基、または、炭素原子数6乃至25の置換もしくは無置換のアリール基のいずれかを表す。) - 請求項1乃至請求項3のいずれか一項において、
前記式(gA)で表される基の、R4およびR5、R5およびR6、並びにR6およびR7の少なくとも一つの組み合わせにおいて縮合してベンゼン環が形成されている正孔輸送層用材料。 - 請求項1乃至請求項3のいずれか一項において、
前記式(gA)で表される基の、R4およびR5、並びに、R6およびR7の少なくとも一つの組み合わせで縮合してベンゼン環が形成されている正孔輸送層用材料。 - 請求項1乃至請求項8のいずれか一項において、
前記Ar1がフェニル基である正孔輸送層用材料。 - 請求項1乃至請求項9のいずれか一項に記載の正孔輸送層用材料を含む発光素子。
- 請求項10に記載の発光素子と、
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10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12に記載の発光装置と、
筐体と、を有する照明装置。
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JP2010195708A (ja) | 2009-02-25 | 2010-09-09 | Toyo Ink Mfg Co Ltd | カルバゾリル基を有する化合物およびその用途 |
JP2012014500A (ja) | 2010-07-01 | 2012-01-19 | Alpine Electronics Inc | 電子機器及びタッチパネルの校正方法 |
JP2016508131A (ja) | 2012-12-24 | 2016-03-17 | ドクサンネオルクス シーオー., エルティーディー.Duk San Neolux Co., Ltd. | 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 |
CN103936653A (zh) | 2013-12-12 | 2014-07-23 | 石家庄诚志永华显示材料有限公司 | 苯并咔唑类oled材料及其制备方法与应用 |
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