JP5242648B2 - 新規化合物ならびにそれを使用した有機電界発光素子、表示装置および照明装置 - Google Patents
新規化合物ならびにそれを使用した有機電界発光素子、表示装置および照明装置 Download PDFInfo
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- JP5242648B2 JP5242648B2 JP2010200210A JP2010200210A JP5242648B2 JP 5242648 B2 JP5242648 B2 JP 5242648B2 JP 2010200210 A JP2010200210 A JP 2010200210A JP 2010200210 A JP2010200210 A JP 2010200210A JP 5242648 B2 JP5242648 B2 JP 5242648B2
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
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- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 2
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- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 229910052792 caesium Inorganic materials 0.000 description 1
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- 238000010549 co-Evaporation Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 239000010931 gold Substances 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5045—Complexes or chelates of phosphines with metallic compounds or metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
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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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Pyridine Compounds (AREA)
Description
有機電界発光素子10は、基板11上に、陽極12、正孔輸送層13、発光層14、電子輸送層15、電子注入層16および陰極17を順次形成した構造を有する。正孔輸送層13、電子輸送層15および電子注入層16は、必要に応じて形成される。
、p−ビス(トリフェニルシリル)ベンゼン(UGH2)等を使用することができる。
図2に示す表示装置20は、横方向の制御線(CL)と縦方向の信号線(DL)がマトリックス状に配置された回路の中に、それぞれ画素21を配置した構成をとる。画素21には、発光素子25および発光素子25に接続された薄膜トランジスタ(TFT)26が含まれる。TFT26の一方の端子は制御線に接続され、他方の端子は信号線に接続される。信号線は、信号線駆動回路22に接続されている。また、制御線は、制御線駆動回路23に接続されている。信号線駆動回路22および制御線駆動回路23は、コントローラ24により制御される。
照明装置100は、ガラス基板101上に、陽極107、有機EL層106、および陰極105を順次積層した構成をとる。封止ガラス102は、陰極105を覆うように配置され、UV接着剤104を用いて固定される。封止ガラス102の陰極105側の面には、乾燥剤103が設置される。
ここで説明する[Cu(NMe2−py)2(PPh3)2]BF4は、4位にジメチルアミノ基を導入したピリジン(NMe2−py)およびトリフェニルホスフィン(PPh3)が銅イオンに配位し、対イオンがBF4 −である銅錯体である。以下に、[Cu(NMe2−py)2(PPh3)2]BF4の合成例を示す。
100mL三つ口フラスコに、テトラキスアセトニトリル銅(I)テトラフルオロボレイト(0.51g, 1.62mmol)およびトリフェニルホスフィン(0.85g, 3.24mmol)を入れ、真空乾燥を行った。三つ口フラスコ内を窒素で置換し、窒素置換したシリンジを用いて、窒素バブリングしたクロロホルムを25mL加えた。室温下、6時間撹拌後、反応溶液をろ過し、不溶物を取り除いた。ろ液にヘキサンを加えると、白色固体が析出した。ろ過して析出物を単離し、目的物質である[Cu(CH3CN)2(PPh3)2]BF4を得た(収率97%)。
50mL三つ口フラスコに、[Cu(CH3CN)2(PPh3)2]BF4(48.4mg, 0.064mmol)および4−ジメチルアミノピリジン(16.1mg, 0.13mmol)を入れ、真空乾燥を行った。三つ口フラスコ内を窒素で置換し、窒素置換したシリンジを用いて、窒素バブリングしたクロロホルムを5mL加えた。室温、窒素雰囲気下、6時間撹拌後、反応溶液をろ過して不溶物を取り除いた。ろ液の溶媒を留去した後、真空乾燥を行い、白色固体を得た。得られた白色固体を、クロロホルム/ヘキサンで再結晶を行うことで、目的物質である[Cu(NMe2−py)2(PPh3)2]BF4を得た(収率86%)。
上記の合成法によって得られた[Cu(NMe2−py)2(PPh3)2]BF4について、フォトルミネッセンス(PL)スペクトルを測定した。測定は、室温、固体状態において、
浜松フォトニクス製マルチチャンネル検出器PMA−11を用いて行った。その結果を図5に示す。励起波長365nmの紫外光で励起させたところ、発光ピーク490nmの青白色発光を示した。
合成した[Cu(NMe2−py)2(PPh3)2]BF4を発光ドーパントとして使用して有機EL素子を作製した。この素子の層構成は、以下の通りである。
上記のように作製した有機EL素子について、発光特性を調べた。図6(a)は、素子の電圧と電流密度との関係を示す図である。図6(b)は、素子の電圧と輝度との関係を示す図である。図6(c)は、素子の電圧と発光効率との関係を示す図である。発光効率は、輝度測定と電流および電圧の測定を同時に行うことによって求めた。輝度は、浜松フォトニクス社製視感度フィルタ付きSiフォトダイオードS7610を用いて測定した。また、電流および電圧の測定は、HEWLETT PACKARD社製半導体パラメータアナライザ4156bを用いて行った。
ピリジン環に置換基を有さない銅錯体[Cu(py)2(PPh3)2]+と、ピリジン環に電子供与性の置換基を導入した銅錯体[Cu(CH3−py)2(PPh3)2]+、[Cu(OMe−py)2(PPh3)2]+、[Cu(NH2−py)2(PPh3)2]+、および[Cu(NMe2−py)2(PPh3)2]+について、分子軌道計算による発光波長の見積もりを行った。[Cu(py)2(PPh3)2]+、[Cu(CH3−py)2(PPh3)2]+、[Cu(OMe−py)2(PPh3)2]+、[Cu(NH2−py)2(PPh3)2]+、および[Cu(NMe2−py)2(PPh3)2]+の構造を以下に示す。
Claims (6)
- 互いに離間して配置された陽極および陰極と、
前記陽極と前記陰極との間に配置され、ホスト材料および発光ドーパントを含む発光層と
を具備する有機電界発光素子であって、
前記発光ドーパントとして、請求項1または2に記載の化合物を含むことを特徴とする有機電界発光素子。 - 前記ホスト材料は、低分子または高分子であることを特徴とする請求項3に記載の有機電界発光素子。
- 請求項3に記載の有機電界発光素子を具備することを特徴とする表示装置。
- 請求項3に記載の有機電界発光素子を具備することを特徴とする照明装置。
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KR1020110014259A KR101343699B1 (ko) | 2010-09-07 | 2011-02-17 | 신규 화합물 및 그것을 사용한 유기 전계 발광 소자, 표시 장치 및 조명 장치 |
CN201410478814.6A CN104230988A (zh) | 2010-09-07 | 2011-02-18 | 新型化合物及使用其的有机场致发光元件、显示装置和照明装置 |
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US13/040,366 US20120056162A1 (en) | 2010-09-07 | 2011-03-04 | Novel compound and organic light-emitting diode, display and illuminating device using the same |
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