JP2009146972A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- JP2009146972A JP2009146972A JP2007320557A JP2007320557A JP2009146972A JP 2009146972 A JP2009146972 A JP 2009146972A JP 2007320557 A JP2007320557 A JP 2007320557A JP 2007320557 A JP2007320557 A JP 2007320557A JP 2009146972 A JP2009146972 A JP 2009146972A
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- light emitting
- organic light
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- emitting device
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Images
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Abstract
【課題】中間層に含まれる材料が発光せず、発光効率が高い有機発光素子を提供する。
【解決手段】陰極と陽極との間に高分子化合物を含む発光層を有し、該陽極と該発光層との間にポリスチレン換算の数平均分子量が１×１０3以上であり、式（１）で表される基を有する脂肪族化合物を含み該発光層に接する中間層を有する有機発光素子を提供する。
−ＣＯ−Ｒ
（１）
［式（１）中、Ｒはアルキル基、アルコキシ基またはヒドロキシル基を表す。］
脂肪族化合物としては、ポリメチルメタクリレート等があげられる。
【選択図】図１Provided is an organic light-emitting element with high luminous efficiency, in which a material contained in an intermediate layer does not emit light.
A light emitting layer containing a polymer compound is provided between a cathode and an anode, and a polystyrene-reduced number average molecular weight is 1 × 10 3 or more between the anode and the light emitting layer. And an organic light emitting device having an intermediate layer in contact with the light emitting layer.
-CO-R
(1)
[In Formula (1), R represents an alkyl group, an alkoxy group, or a hydroxyl group. ]
Examples of the aliphatic compound include polymethyl methacrylate.
[Selection] Figure 1
Description
本発明は有機発光素子に関する。 The present invention relates to an organic light emitting device.
近年、有機発光素子の発光効率を高めるため、陽極と発光層との間に様々な中間層を挿入する検討が行われている。例えば、発光層に接して式（Ａ）で示される芳香族高分子化合物を含む中間層を有する有機発光素子が提案されている。（非特許文献１） In recent years, studies have been made to insert various intermediate layers between the anode and the light emitting layer in order to increase the light emission efficiency of the organic light emitting device. For example, an organic light emitting device having an intermediate layer containing an aromatic polymer compound represented by the formula (A) in contact with the light emitting layer has been proposed. (Non-Patent Document 1)
一般に、特定の色を発光する有機発光素子を製造する場合、当該特定の色を発光する材料を発光層に用いる。しかし、上記有機発光素子は、中間層に含まれる式（Ａ）で示される芳香族高分子化合物自体が発光するという課題がある。 Generally, when manufacturing an organic light emitting device that emits a specific color, a material that emits the specific color is used for the light emitting layer. However, the organic light emitting device has a problem that the aromatic polymer compound itself represented by the formula (A) contained in the intermediate layer emits light.
そこで本発明は、中間層に含まれる材料が発光せず、発光効率が高い有機発光素子を提供することを目的とする。 Accordingly, an object of the present invention is to provide an organic light-emitting device in which the material contained in the intermediate layer does not emit light and has high luminous efficiency.
即ち本発明は第一に、陰極と陽極との間に高分子化合物を含む発光層を有し、該陽極と該発光層との間にポリスチレン換算の数平均分子量が１×１０3以上であり、式（１）で表される基を有する脂肪族化合物を含み該発光層に接する中間層を有する有機発光素子を提供する。
−ＣＯ−Ｒ
（１）
［式（１）中、Ｒはアルキル基、アルコキシ基またはヒドロキシル基を表す。］
That is, the present invention first has a light emitting layer containing a polymer compound between the cathode and the anode, and the polystyrene-equivalent number average molecular weight is 1 × 10 3 or more between the anode and the light emitting layer. Provided is an organic light-emitting device having an intermediate layer containing an aliphatic compound having a group represented by the formula (1) and in contact with the light-emitting layer.
-CO-R
(1)
[In Formula (1), R represents an alkyl group, an alkoxy group, or a hydroxyl group. ]
本発明の有機発光素子は、中間層に含まれる材料が発光せず、優れた発光効率を示すため、本発明は工業的に極めて有用である。 The organic light-emitting device of the present invention is extremely useful industrially because the material contained in the intermediate layer does not emit light and exhibits excellent luminous efficiency.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
本発明の有機発光素子は、陰極と陽極との間に高分子化合物を含む発光層を有し、該陽極と該発光層との間に脂肪族化合物を含み該発光層に接する中間層を有する。 The organic light emitting device of the present invention has a light emitting layer containing a polymer compound between a cathode and an anode, and has an intermediate layer containing an aliphatic compound and in contact with the light emitting layer between the anode and the light emitting layer. .
本発明に用いられる脂肪族化合物は、ポリスチレン換算の数平均分子量が１×１０3以上であり、１×１０3〜１×１０6であることが好ましく、１×１０4〜１×１０5であることがより好ましい。また、ポリスチレン換算の重量平均分子量が１×１０3〜１×１０8であることが好ましく、１×１０4〜１×１０7であることがより好ましい。 The aliphatic compound used in the present invention has a polystyrene-equivalent number average molecular weight of 1 × 10 3 or more, preferably 1 × 10 3 to 1 × 10 6 , and preferably 1 × 10 4 to 1 × 10 5 . More preferably. Moreover, it is preferable that the weight average molecular weight of polystyrene conversion is 1 * 10 < 3 > -1 * 10 < 8 >, and it is more preferable that it is 1 * 10 < 4 > -1 * 10 < 7 >.
本発明に用いられる脂肪族化合物は、式（１）で表される基を有する。式（１）中、Ｒはアルキル基、アルコキシ基またはヒドロキシル基を表す。また、該脂肪族化合物は、環式構造を有していてもよい。 The aliphatic compound used in the present invention has a group represented by the formula (1). In formula (1), R represents an alkyl group, an alkoxy group or a hydroxyl group. The aliphatic compound may have a cyclic structure.
Ｒで表されるアルキル基は、直鎖状でも分岐状でもよく、シクロアルキル基でもよい。炭素数は通常１〜２０程度であり、アルキル基の具体例としては、メチル基、エチル基、ｎ−プロピル基、ｉ−プロピル基、ｎ−ブチル基、ｉ−ブチル基、ｓ−ブチル基、ｔ−ブチル基、ペンチル基、イソアミル基、ヘキシル基、シクロヘキシル基、ヘプチル基、オクチル基、２−エチルヘキシル基、ノニル基、デシル基等があげられる。 The alkyl group represented by R may be linear or branched, and may be a cycloalkyl group. The number of carbon atoms is usually about 1 to 20, and specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, Examples thereof include t-butyl group, pentyl group, isoamyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group and the like.
Ｒで表されるアルコキシ基は、直鎖状でも分岐状でもよく、シクロアルキルオキシ基でもよい。炭素数は通常１〜２０程度であり、アルコキシ基の具体例としては、メトキシ基、エトキシ基、ｎ−プロピルオキシ基、ｉ−プロピルオキシ基、ｎ−ブトキシ基、ｉ−ブトキシ基、ｓ−ブトキシ基、ｔ−ブトキシ基、ペンチルオキシ基、ヘキシルオキシ基、シクロヘキシルオキシ基、ヘプチルオキシ基、オクチルオキシ基、２−エチルヘキシルオキシ基、ノニルオキシ基、デシルオキシ基等があげられる。 The alkoxy group represented by R may be linear or branched, and may be a cycloalkyloxy group. The number of carbon atoms is usually about 1 to 20, and specific examples of the alkoxy group include methoxy group, ethoxy group, n-propyloxy group, i-propyloxy group, n-butoxy group, i-butoxy group, s-butoxy group. Group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group and the like.
本発明に用いられる脂肪族化合物は、芳香族基を有さないため、発光しない。そのため、該脂肪族化合物を含む中間層からの発光がなく、発光層から発光する色と中間層から発光する色が混色するという問題を生じないのである。 Since the aliphatic compound used in the present invention does not have an aromatic group, it does not emit light. Therefore, there is no light emission from the intermediate layer containing the aliphatic compound, and there is no problem that the color emitted from the light emitting layer and the color emitted from the intermediate layer are mixed.
本発明に用いられる脂肪族化合物は、式（１）で表される基以外の基を側鎖または末端に有していてもよい。具体的には、アルキル基、アルコキシ基等があげられる。 The aliphatic compound used in the present invention may have a group other than the group represented by the formula (1) in the side chain or the terminal. Specific examples include an alkyl group and an alkoxy group.
本発明に用いられる脂肪族化合物は、式（２）で表される繰り返し単位を有することが好ましい。
（２）
［式（２）中、Ｒ1はアルキル基または水素原子を表す。Ｒは前述と同じ意味を表す。］
The aliphatic compound used in the present invention preferably has a repeating unit represented by the formula (2).
(2)
[In the formula (2), R 1 represents an alkyl group or a hydrogen atom. R represents the same meaning as described above. ]
式（２）中、Ｒとしては、アルコキシ基が好ましい。 In the formula (2), R is preferably an alkoxy group.
Ｒ1がアルキル基である場合の具体例としては、Ｒの具体例として例示した基と同様の基があげられる。アルキル基の中ではメチル基が好ましい。 Specific examples in the case where R 1 is an alkyl group include the same groups as those exemplified as specific examples of R. Of the alkyl groups, a methyl group is preferred.
本発明に用いられる脂肪族化合物において、脂肪族化合物が有する全繰り返し単位の合計を１００とすると、式（２）で表される繰り返し単位の合計が１０〜１００であることが好ましい。 In the aliphatic compound used in the present invention, when the total number of all repeating units of the aliphatic compound is 100, the total number of repeating units represented by the formula (2) is preferably 10 to 100.
脂肪族化合物としては、ポリメチルメタクリレート、ポリエチルメタクリレート、ポリブチルメタクリレートポリアクリル酸、ポリアクリル酸メチル、ポリアクリル酸エチル、ポリアクリル酸ブチル等が好適に用いることができる。有機発光素子の発光効率の観点からは、脂肪族化合物の最高被占分子軌道(HOMO)エネルギーと最低空位分子軌道(LUMO)エネルギーの差が3.5eV以上であることが好ましく、中でも、脂肪族化合物がポリメチルメタクリレートであることがより好ましい。本発明に用いられる脂肪族化合物を成膜して中間層を製造する場合、塗布法で成膜することが可能である。 As the aliphatic compound, polymethyl methacrylate, polyethyl methacrylate, polybutyl methacrylate polyacrylic acid, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate and the like can be suitably used. From the viewpoint of the luminous efficiency of the organic light-emitting device, the difference between the highest occupied molecular orbital (HOMO) energy and the lowest vacant molecular orbital (LUMO) energy of the aliphatic compound is preferably 3.5 eV or more. Is more preferably polymethyl methacrylate. When the intermediate compound is manufactured by forming the aliphatic compound used in the present invention, it can be formed by a coating method.
本発明の有機発光素子が有する中間層の膜厚は、発光効率の観点から5nm以上であることが好ましい、正孔透過性の観点から15nm以下であることが好ましい。 The thickness of the intermediate layer of the organic light emitting device of the present invention is preferably 5 nm or more from the viewpoint of light emission efficiency, and preferably 15 nm or less from the viewpoint of hole permeability.
本発明の有機発光素子の層構成としては、
（１） 陽極／正孔注入層／中間層／発光層／陰極
（２） 陽極／正孔注入層／正孔輸送層／中間層／発光層／陰極
（３） 陽極／正孔注入層／中間層／発光層／電子注入層／陰極
（４） 陽極／正孔注入層／正孔輸送層／中間層／発光層／電子注入層／陰極
等が挙げられる。
As the layer structure of the organic light emitting device of the present invention,
(1) Anode / hole injection layer / intermediate layer / light emitting layer / cathode (2) Anode / hole injection layer / hole transport layer / intermediate layer / light emitting layer / cathode (3) Anode / hole injection layer / intermediate Layer / light emitting layer / electron injection layer / cathode (4) Anode / hole injection layer / hole transport layer / intermediate layer / light emitting layer / electron injection layer / cathode and the like.
本発明の有機発光素子が有する発光層は、電界印加時に陽極又は正孔注入層より正孔を注入することができ、陰極又は電子注入層より電子を注入することができる機能、注入した電荷(電子と正孔)を電界の力で移動させる機能、電子と正孔の再結合の場を提供し、これを発光につなげる機能を有するものである。 The light emitting layer of the organic light emitting device of the present invention can inject holes from the anode or the hole injection layer when an electric field is applied, and can inject electrons from the cathode or the electron injection layer. It has a function of moving electrons and holes) by the force of an electric field, a field of recombination of electrons and holes, and a function of connecting this to light emission.
本発明の有機発光素子が有する発光層が含む高分子化合物は、蛍光あるいは燐光を発光することが可能な高分子発光材料である。
高分子発光材料としては、公知の高分子発光材料である、ポリフルオレン誘導体(PF)、ポリパラフェニレンビニレン誘導体(PPV)、ポリフェニレン誘導体(PP)、ポリパラフェニレン誘導体(PPP)、ポリチオフェン誘導体、ポリジアルキルフルオレン(PDAF)、ポリフルオレンベンゾチアジアゾール(PFBT)、ポリアルキルチオフェン(PAT)等の共役系高分子化合物を好適に用いることができる。
また、これら高分子発光材料から成る発光層は、ペリレン系色素、クマリン系色素、ローダミン系色素などの高分子系色素材料や、ルブレン、ペリレン、9,10−ジフェニルアントラセン、テトラフェニルブタジエン、ナイルレッド、クマリン6、キナクリドン等の低分子色素材料を含有しても良い。
The polymer compound contained in the light emitting layer of the organic light emitting device of the present invention is a polymer light emitting material capable of emitting fluorescence or phosphorescence.
Polymer light-emitting materials include known polymer light-emitting materials such as polyfluorene derivative (PF), polyparaphenylene vinylene derivative (PPV), polyphenylene derivative (PP), polyparaphenylene derivative (PPP), polythiophene derivative, poly Conjugated polymer compounds such as dialkylfluorene (PDAF), polyfluorene benzothiadiazole (PFBT), and polyalkylthiophene (PAT) can be suitably used.
In addition, the light emitting layer composed of these polymer light emitting materials is composed of polymer dye materials such as perylene dyes, coumarin dyes, rhodamine dyes, rubrene, perylene, 9,10-diphenylanthracene, tetraphenylbutadiene, and Nile Red. In addition, a low molecular dye material such as coumarin 6 or quinacridone may be contained.
本発明の有機発光素子が有する陽極は、正孔注入層、正孔輸送層、発光層等に正孔を供給するものである。陽極の材料には、金属、合金、金属酸化物、電気伝導性化合物又はこれらの混合物等を用いることができる。具体的には、酸化スズ、酸化亜鉛、酸化インジウム、酸化インジウムスズ（ＩＴＯ）、酸化インジウム−酸化亜鉛（ＩＺＯ）等の導電性金属酸化物、又は金、銀、クロム、ニッケル等の金属、さらにこれらの導電性金属酸化物と金属との混合物又は積層物、ヨウ化銅、硫化銅等の無機導電性物質、ポリアニリン類、PEDOT（ポリ(3,4−エチレンジオキシチオフェン)、ポリピロール等の有機導電性材料及びこれらとＩＴＯとの積層物等が挙げられる。これらの中では、4.5eV以上の仕事関数を有することが好ましく、具体的には、ＩＴＯ、ＩＺＯ、金、プラチナ等があげられる。 The anode of the organic light emitting device of the present invention supplies holes to a hole injection layer, a hole transport layer, a light emitting layer and the like. As the material of the anode, a metal, an alloy, a metal oxide, an electrically conductive compound, a mixture thereof, or the like can be used. Specifically, conductive metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium oxide-zinc oxide (IZO), or metals such as gold, silver, chromium, nickel, Mixtures or laminates of these conductive metal oxides and metals, inorganic conductive materials such as copper iodide and copper sulfide, polyanilines, organic compounds such as PEDOT (poly (3,4-ethylenedioxythiophene) and polypyrrole) Examples thereof include conductive materials and laminates of these with ITO, etc. Among them, it is preferable to have a work function of 4.5 eV or more, and specific examples thereof include ITO, IZO, gold, and platinum.
本発明の有機発光素子が有する陰極は、電子注入層、電子輸送層、発光層等に電子を供給するものである。陰極の材料としては、金属、合金、金属ハロゲン化物、金属酸化物、電気伝導性化合物又はこれらの混合物を用いることができる。陰極の材料の具体例としては、アルカリ金属及びそのフッ化物もしくは酸化物、アルカリ土類金属及びそのフッ化物もしくは酸化物、金、銀、鉛、アルミニウム、合金または金属の混合物、希土類金属等があげられる。アルカリ金属としては、リチウム、ナトリウム、カリウム、セシウム等があげられる。アルカリ土類金属としては、マグネシウム、カルシウム、バリウム等があげられる。合金としては、ナトリウム− カリウム合金、リチウム− アルミニウム合金、マグネシウム−銀合金等があげられる。金属の混合物としては、ナトリウムとカリウムとの混合物、リチウムとアルミニウムとの混合物、マグネシウムと銀との混合物等があげられる。希土類金属としては、インジウム、イッテルビウム等があげられる。また、上記材料から成る単層構造であってもよいし、異種組成の複数層からなる多層構造であってもよい。 The cathode of the organic light emitting device of the present invention supplies electrons to an electron injection layer, an electron transport layer, a light emitting layer and the like. As a material for the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples of cathode materials include alkali metals and fluorides or oxides thereof, alkaline earth metals and fluorides or oxides thereof, gold, silver, lead, aluminum, alloys or mixtures of metals, rare earth metals, and the like. It is done. Examples of the alkali metal include lithium, sodium, potassium, cesium and the like. Examples of the alkaline earth metal include magnesium, calcium, barium and the like. Examples of the alloy include a sodium-potassium alloy, a lithium-aluminum alloy, and a magnesium-silver alloy. Examples of the metal mixture include a mixture of sodium and potassium, a mixture of lithium and aluminum, a mixture of magnesium and silver, and the like. Examples of rare earth metals include indium and ytterbium. In addition, a single layer structure made of the above materials may be used, or a multilayer structure made of a plurality of layers having different compositions may be used.
本発明の有機発光素子が正孔注入層および／または正孔輸送層を有する場合、陽極から正孔を注入する機能または正孔を輸送する機能を有していればよく、さらに陰極から注入された電子を障壁する機能を有していてもよい。正孔注入層、正孔輸送層に用いる材料としては、公知の材料を適宜選択して使用できるが、具体例としてはカルバゾール誘導体、トリアゾール誘導体、オキサゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体、ピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、芳香族第三級アミン化合物、スチリルアミン化合物、芳香族ジメチリディン系化合物、ポルフィリン系化合物、ポリシラン系化合物、ポリ（N−ビニルカルバゾール） 誘導体、有機シラン誘導体、およびこれらを含む重合体が挙げられる。また、アニリン系共重合体、チオフェンオリゴマー、ポリチオフェン等の導電性高分子オリゴマー、PEDOT（ポリ(3,4−エチレンジオキシチオフェン)、ポリピロール等の有機導電性材料も挙げることができる。前記材料は単成分であってもあるいは複数の成分からなる組成物であってもよい。また、前記正孔注入層及び前記正孔輸送層は、前記材料の１種又は２種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。 When the organic light-emitting device of the present invention has a hole injection layer and / or a hole transport layer, it may have a function of injecting holes from the anode or a function of transporting holes, and is further injected from the cathode. It may have a function of blocking electrons. As materials used for the hole injection layer and the hole transport layer, known materials can be appropriately selected and used. Specific examples include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyaryls. Alkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, Aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, organic silane derivatives, and polymers containing these. In addition, conductive polymer oligomers such as aniline copolymers, thiophene oligomers, and polythiophenes, and organic conductive materials such as PEDOT (poly (3,4-ethylenedioxythiophene) and polypyrrole are also included. The hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the materials. It may be a multilayer structure composed of a plurality of layers having the same composition or different compositions.
本発明の有機発光素子が、電子注入層および／または電子輸送層を有する場合、陰極から電子を注入する機能、電子を輸送する機能、陽極から注入された正孔を障壁する機能のいずれかを有しているものであればよい。電子注入層、電子輸送層に用いる材料としては、公知の材料を適宜選択して使用できるが、具体例としてはトリアゾール誘導体、オキサゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、フルオレノン誘導体、アントラキノジメタン誘導体、アントロン誘導体、ジフェニルキノン誘導体、チオピランジオキシド誘導体、カルボジイミド誘導体、フルオレニリデンメタン誘導体、ジスチリルピラジン誘導体、ナフタレン、ペリレン等の芳香環テトラカルボン酸無水物、フタロシアニン誘導体、８−キノリノール誘導体の金属錯体やメタルフタロシアニン、ベンゾオキサゾールやベンゾチアゾールを配位子とする金属錯体に代表される各種金属錯体、有機シラン誘導体等が挙げられる。また、前記電子注入層及び前記電子輸送層は、前記材料の１種又は２種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。 When the organic light-emitting device of the present invention has an electron injection layer and / or an electron transport layer, any one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode What is necessary is just to have. As materials used for the electron injection layer and the electron transport layer, known materials can be appropriately selected and used. Specific examples include triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane. Derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic ring tetracarboxylic anhydrides such as naphthalene and perylene, phthalocyanine derivatives, 8-quinolinol derivatives Examples include metal complexes, metal phthalocyanines, various metal complexes represented by metal complexes having benzoxazole or benzothiazole as a ligand, and organic silane derivatives. In addition, the electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the materials, or a multilayer structure composed of a plurality of layers having the same composition or different compositions. Good.
本発明の有機発光素子の中間層を除く各有機層の好ましい膜厚は材料の種類や層構成によって異なり特に制限されないが、一般的には膜厚が薄すぎるとピンホール等の欠陥が生じやすく、逆に厚すぎると高い印加電圧が必要となり効率が悪くなるため、通常は数ｎｍから１μｍの範囲が好ましい。 The preferred film thickness of each organic layer excluding the intermediate layer of the organic light-emitting device of the present invention varies depending on the type of material and the layer structure and is not particularly limited. Generally, however, if the film thickness is too thin, defects such as pinholes are likely to occur. On the other hand, if the thickness is too thick, a high applied voltage is required and the efficiency is deteriorated.
本発明の有機発光素子において、その素子構造は、陰極と陽極との間に高分子化合物を含む発光層を有し、該発光層に接して陽極との間に本発明に用いられる脂肪族化合物を含む中間層を有するものであれば特に限定されないが、ガラスまたはプラスチック基板上にインジウムスズ酸化物（ＩＴＯ）から成る陽極が形成され、その上に正孔注入層が成膜され、その上に正孔輸送層が成膜され、その上に中間層が成膜され、その上に発光層が成膜され、その上に陰極が形成された構造が望ましい。 In the organic light-emitting device of the present invention, the element structure has a light-emitting layer containing a polymer compound between the cathode and the anode, and the aliphatic compound used in the present invention in contact with the light-emitting layer and between the anode Is not particularly limited as long as it has an intermediate layer containing, but an anode made of indium tin oxide (ITO) is formed on a glass or plastic substrate, and a hole injection layer is formed thereon, on which A structure in which a hole transport layer is formed, an intermediate layer is formed thereon, a light emitting layer is formed thereon, and a cathode is formed thereon is desirable.
中間層上に発光層を塗布法で成膜する場合、特に、両方の層を塗布法によって形成する場合には、先に塗布した層が後から塗布する層に含まれる溶媒に溶解して積層構造を作成できなくなる事がある。この場合には、下層を溶媒不溶にする方法を用いることができる。溶媒不溶にする方法としては、脂肪族化合物自体に架橋基を合成的に付けるもの方法、アクリレート基に代表される架橋基を持った低分子化合物を架橋剤として混合させる方法、下層を加熱して上層作成に用いる有機溶媒に対して不溶化する方法、などが挙げられる。架橋剤を混合させる方法の具体例としては、例えば、架橋剤としてジペンタエリスリトールヘキサアクリレート(DPHA)、トリスペンタエリスリトールオクタアクリレート、１,４−ブタンジオールジアクリレート等を脂肪族化合物と混合して成膜し、その後加熱処理や紫外光照射処理等により中間層を不溶化することが出来る。
また、架橋以外で下層を溶解させずに積層するその他の方法として、隣り合った層に異なる極性の溶液を用いる方法があり、たとえば、下層を極性溶媒に溶解しない高分子化合物を含む溶液を用いて製造し、上層を製造する際、高分子化合物を極性溶媒に溶解させた溶液を塗布しても下層が溶解しないようにする方法などがある。
When the light emitting layer is formed on the intermediate layer by the coating method, particularly when both layers are formed by the coating method, the layer applied first is dissolved in the solvent contained in the layer to be applied later and laminated. The structure may not be created. In this case, a method of making the lower layer solvent insoluble can be used. As a method for making the solvent insoluble, a method of synthetically attaching a crosslinking group to the aliphatic compound itself, a method of mixing a low molecular compound having a crosslinking group represented by an acrylate group as a crosslinking agent, and heating the lower layer For example, a method of insolubilizing with respect to the organic solvent used for forming the upper layer may be mentioned. As a specific example of the method of mixing the crosslinking agent, for example, as a crosslinking agent, dipentaerythritol hexaacrylate (DPHA), trispentaerythritol octaacrylate, 1,4-butanediol diacrylate or the like is mixed with an aliphatic compound. Then, the intermediate layer can be insolubilized by heat treatment or ultraviolet light irradiation treatment.
In addition, as another method of laminating without dissolving the lower layer other than cross-linking, there is a method of using different polar solutions in adjacent layers, for example, using a solution containing a polymer compound that does not dissolve the lower layer in a polar solvent. When the upper layer is manufactured, the lower layer is not dissolved even if a solution in which a polymer compound is dissolved in a polar solvent is applied.
本発明の有機発光素子では、前記各層の形成方法は特に限定されず公知の方法を使用できる。具体的には、LB法、分子積層法、塗布法等があげられる。塗布法としては、キャスティング法、スピンコート法、バーコート方、ブレードコート法、ロールコート法、グラビア印刷、スクリーン印刷、インクジェット法等があげられる。これらの中では、製造プロセスを簡略化できる点で、塗布法で成膜することが好ましい。前記塗布法では、塗布液を調製し、該塗布液を所望の層（あるいは電極）上に、塗布・乾燥することによって形成することができる。塗布液中にはホスト材料または／及びバインダーとして樹脂を含有させてもよく、樹脂は溶媒に溶解状態とすることも、分散状態とすることもできる。前記樹脂としては、ポリビニルカルバゾール、ポリオレフィン等の非共役高分子化合物、ポリアリーレン等の共役高分子化合物を使用することができる。より具体的には、例えば、ポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルホン、ポリフェニレンオキシド、ポリブタジエン、ポリ（ N−ビニルカルバゾール） 、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリアミド、エチルセルロース、酢酸ビニル、ABS樹脂、ポリウレタン、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコン樹脂等から目的に応じて選択できる。溶液は目的に応じて副成分として、酸化防止剤、粘度調整剤等を含有しても良い。 In the organic light emitting device of the present invention, a method for forming each layer is not particularly limited, and a known method can be used. Specific examples include LB method, molecular lamination method, coating method and the like. Examples of the coating method include casting method, spin coating method, bar coating method, blade coating method, roll coating method, gravure printing, screen printing, and ink jet method. In these, it is preferable to form into a film by the coating method at the point which can simplify a manufacturing process. In the coating method, it can be formed by preparing a coating solution and coating and drying the coating solution on a desired layer (or electrode). The coating liquid may contain a resin as a host material or / and a binder, and the resin can be dissolved in a solvent or dispersed. As the resin, non-conjugated polymer compounds such as polyvinyl carbazole and polyolefin, and conjugated polymer compounds such as polyarylene can be used. More specifically, for example, polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin. Polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. can be selected according to the purpose. The solution may contain an antioxidant, a viscosity modifier and the like as subcomponents depending on the purpose.
溶液の溶媒は薄膜の成分を均一に溶解または分散し安定なものを公知の溶媒から適宜選択して使用できる。このような溶媒として、アルコール、ケトン、含塩素脂肪族炭化水素、芳香族炭化水素、脂肪族炭化水素、アミド、スルホキシド等があげられる。アルコールとしては、メタノール、エタノール、イソプロピルアルコール等があげられる。ケトンとしては、アセトン、メチルエチルケトン等があげられる。含塩素脂肪族炭化水素としては、クロロホルム、１，２−ジクロロエタン等があげられる。芳香族炭化水素としては、ベンゼン、トルエン、キシレン等があげられる。脂肪族炭化水素としては、ノルマルヘキサン、シクロヘキサン等があげられる。アミドとしては、ジメチルホルムアミド等があげられる。スルホキシドとしては、ジメチルスルホキシド等があげられる。溶液は、溶媒を１種類含んでいても、２種類以上含んでいてもよい。 As the solvent of the solution, a stable one in which the components of the thin film are uniformly dissolved or dispersed can be appropriately selected from known solvents. Examples of such a solvent include alcohol, ketone, chlorine-containing aliphatic hydrocarbon, aromatic hydrocarbon, aliphatic hydrocarbon, amide, sulfoxide and the like. Examples of the alcohol include methanol, ethanol, isopropyl alcohol and the like. Examples of the ketone include acetone and methyl ethyl ketone. Examples of chlorine-containing aliphatic hydrocarbons include chloroform and 1,2-dichloroethane. Aromatic hydrocarbons include benzene, toluene, xylene and the like. Examples of the aliphatic hydrocarbon include normal hexane and cyclohexane. Examples of the amide include dimethylformamide. Examples of the sulfoxide include dimethyl sulfoxide. The solution may contain one type of solvent or two or more types of solvent.
インクジェット法においては、インクの吐出性ならびにその再現性のために公知の成分を用いることが出来る。ノズルからのインクの蒸発を抑えるためには、アニソール、ビシクロヘキシル等の高沸点の溶媒を成分に用いることが好ましい。また成分を選択してインクの粘度を１〜１００mPa・ｓとすることが好ましい。 In the ink jet method, known components can be used for ink ejection and reproducibility. In order to suppress the evaporation of ink from the nozzle, it is preferable to use a high boiling point solvent such as anisole or bicyclohexyl as a component. Further, it is preferable that the viscosity of the ink is set to 1 to 100 mPa · s by selecting the components.
本発明の有機発光素子の用途は特に制限されないが、照明用光源、サイン用光源、バックライト用光源、ディスプレイ装置、プリンターヘッド等に用いることが出来る。ディスプレイ装置としては公知の駆動技術、駆動回路等を用い、セグンメント型、ドットマトリクス型等の構成を選択することができる。 The application of the organic light-emitting device of the present invention is not particularly limited, but it can be used for illumination light sources, sign light sources, backlight light sources, display devices, printer heads, and the like. As the display device, a known drive technology, drive circuit, or the like can be used to select a segment type, a dot matrix type, or the like.
実施例１（有機発光素子の作製）
本発明における有機発光素子の構造と製造方法を図１に基づいて以下に説明する。
ITO陽極が成膜されたガラス基板上に、正孔注入材料溶液をスピンコート法によって成膜し、膜厚60nmの正孔注入層を作製した。正孔注入層を成膜したガラス基板を200℃で10分加熱処理をして正孔注入層を不溶化させた。ここで正孔注入材料溶液にはスタルクヴイテック(株)より入手可能なPEDOT:PSS水溶液（ポリ(3,4−エチレンジオキシチオフェン)・ポリスチレンスルフォン酸、製品名Baytron）を用いた。
Example 1 (Preparation of organic light-emitting device)
The structure and manufacturing method of the organic light emitting device in the present invention will be described below with reference to FIG.
On the glass substrate on which the ITO anode was formed, a hole injection material solution was formed by spin coating to form a hole injection layer having a thickness of 60 nm. The glass substrate on which the hole injection layer was formed was heat-treated at 200 ° C. for 10 minutes to insolubilize the hole injection layer. Here, PEDOT: PSS aqueous solution (poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid, product name Baytron) available from Stark Vitec Co., Ltd. was used as the hole injection material solution.
ついで、正孔輸送性高分子材料をキシレン溶媒に重量濃度0.5%で溶解させ、正孔輸送性高分子材料溶液とした。正孔輸送性高分子材料溶液を前記正孔注入層上にスピンコート法によって成膜し、膜厚20nmの正孔輸送層を作製した。正孔輸送層を成膜したガラス基板を200℃で15分加熱処理して正孔輸送層を不溶化させた。 Next, the hole transporting polymer material was dissolved in a xylene solvent at a weight concentration of 0.5% to obtain a hole transporting polymer material solution. A hole transporting polymer material solution was formed on the hole injection layer by spin coating to produce a 20 nm thick hole transport layer. The glass substrate on which the hole transport layer was formed was heat-treated at 200 ° C. for 15 minutes to insolubilize the hole transport layer.
ついで、ポリメチルメタクリレート（PMMA）とジペンタエリスリトールヘキサアクリレート(DPHA)を重量比がPMMA:DPHA=100:20となるようにキシレン溶媒に溶解させ、中間層材料溶液とした。中間層材料溶液を前記正孔輸送層上にスピンコート法によって成膜し、膜厚10nmの中間層を作製した。中間層を成膜したガラス基板に紫外光を照射し、中間層を不溶化させた。 Subsequently, polymethyl methacrylate (PMMA) and dipentaerythritol hexaacrylate (DPHA) were dissolved in a xylene solvent so that the weight ratio would be PMMA: DPHA = 100: 20 to obtain an intermediate layer material solution. An intermediate layer material solution was formed on the hole transport layer by a spin coating method to prepare an intermediate layer having a thickness of 10 nm. The glass substrate on which the intermediate layer was formed was irradiated with ultraviolet light to insolubilize the intermediate layer.
ついで、高分子発光材料であるＬｕｍａｔｉｏｎ ＢＰ３６１（サメイション社製）をキシレン溶媒に重量濃度1.4%で溶解させ高分子発光材料溶液とした。高分子発光材料溶液を前記中間層上にスピンコート法によって成膜し、膜厚70nmの発光層を作製した。 Next, Lumination BP361 (manufactured by Summation), which is a polymer light emitting material, was dissolved in a xylene solvent at a weight concentration of 1.4% to obtain a polymer light emitting material solution. A polymer light emitting material solution was formed on the intermediate layer by spin coating to produce a light emitting layer having a thickness of 70 nm.
ついで、前記発光層を成膜したガラス基板を１３０℃で４５分加熱処理して溶媒を蒸発させた。ついで、前記発光層上に真空蒸着装置にてバリウムを５ｎｍ堆積させ、続いてアルミニウムを１００ｎｍ堆積させ陰極とした。ついで、２液混合型エポキシ樹脂と封止ガラス板を用いて、前記陰極を形成したガラス基板を封止し、有機発光素子１を作製した。定電圧・電流電源を準備して、有機発光素子１のITOを電源の陽極に、アルミニウムを電源の陰極に接続して電圧を印加し、電流注入によって有機発光素子１を発光させた。電流密度１.０ｍＡ／ｃｍ２で駆動させた時の有機発光素子１の発光効率を表１に示す。なお、有機発光素子１において、中間層に含まれる材料は発光しないため、発光層からの発光との混色は観測されなかった。 Subsequently, the glass substrate on which the light emitting layer was formed was heat-treated at 130 ° C. for 45 minutes to evaporate the solvent. Next, 5 nm of barium was deposited on the light emitting layer by a vacuum evaporation apparatus, and then 100 nm of aluminum was deposited to form a cathode. Next, the glass substrate on which the cathode was formed was sealed using a two-component mixed epoxy resin and a sealing glass plate, and an organic light emitting device 1 was manufactured. A constant voltage / current power source was prepared. A voltage was applied by connecting ITO of the organic light emitting device 1 to the anode of the power source and aluminum to the cathode of the power source, and the organic light emitting device 1 was caused to emit light by current injection. Table 1 shows the light emission efficiency of the organic light emitting device 1 when driven at a current density of 1.0 mA / cm 2. In the organic light emitting device 1, since the material contained in the intermediate layer does not emit light, no color mixture with the light emitted from the light emitting layer was observed.
実施例２
高分子発光材料としてＬｕｍａｔｉｏｎ ＧＰ１３００（サメイション社製）を用いた以外は実施例１と同様の製造方法で有機発光素子２を作製した。定電圧・電流電源を準備して、有機発光素子２のITOを電源の陽極に、アルミニウムを電源の陰極に接続して電圧を印加し、電流注入によって有機発光素子を発光させた。電流密度３０ｍＡ／ｃｄ２で駆動させた時の有機発光素子２の発光効率を表１に示す。なお、有機発光素子２において、中間層に含まれる材料は発光しないため、発光層からの発光との混色は観測されなかった。
Example 2
An organic light-emitting device 2 was produced by the same production method as in Example 1 except that Lumination GP1300 (manufactured by Summation) was used as the polymer light-emitting material. A constant voltage / current power source was prepared. A voltage was applied by connecting ITO of the organic light emitting device 2 to the anode of the power source and aluminum to the cathode of the power source, and the organic light emitting device was caused to emit light by current injection. Table 1 shows the luminous efficiency of the organic light emitting device 2 when driven at a current density of 30 mA / cd2. In the organic light emitting device 2, since the material contained in the intermediate layer does not emit light, no color mixture with the light emitted from the light emitting layer was observed.
比較例１
中間層を成膜しない以外は実施例１と同様の製造方法によって有機発光素子３を作製した。定電圧・電流電源を準備して、有機発光素子３のITOを電源の陽極に、アルミニウムを電源の陰極に接続して電圧を印加し、電流注入によって有機発光素子３を発光させた。電流密度１.０ｍＡ／ｃｍ２で駆動させた時の有機発光素子３の発光効率を表１に示す。
Comparative Example 1
An organic light emitting device 3 was produced by the same production method as in Example 1 except that no intermediate layer was formed. A constant voltage / current power source was prepared. A voltage was applied by connecting ITO of the organic light emitting element 3 to the anode of the power source and aluminum to the cathode of the power source, and the organic light emitting element 3 was caused to emit light by current injection. Table 1 shows the light emission efficiency of the organic light emitting device 3 when driven at a current density of 1.0 mA / cm 2.
比較例２
中間層を成膜しない以外は実施例２と同様の製造方法によって有機発光素子３を作製した。定電圧・電流電源を準備して、有機発光素子４のITOを電源の陽極に、アルミニウムを電源の陰極に接続して電圧を印加し、電流注入によって有機発光素子４を発光させた。電流密度１.０ｍＡ／ｃｍ２で駆動させた時の有機発光素子４の発光効率を表１に示す。
Comparative Example 2
An organic light emitting device 3 was produced by the same production method as in Example 2 except that no intermediate layer was formed. A constant voltage / current power source was prepared. A voltage was applied by connecting ITO of the organic light emitting element 4 to the anode of the power source and aluminum to the cathode of the power source, and the organic light emitting element 4 was caused to emit light by current injection. Table 1 shows the light emission efficiency of the organic light emitting device 4 when driven at a current density of 1.0 mA / cm 2.
表１から明らかであるように、同一高分子発光材料を用いた有機発光素子間（有機発光素子１と３、および、有機発光素子２と４）で比較すると、ポリメチルメタクリレートを含む中間層を有する本発明の有機発光素子（有機発光素子１と２）の発光効率は、中間層を有しない発光素子（有機発光素子３と４）に比べ、著しく高い。
As is clear from Table 1, when compared between organic light emitting devices using the same polymer light emitting material (organic light emitting devices 1 and 3 and organic light emitting devices 2 and 4), an intermediate layer containing polymethyl methacrylate is obtained. The light emitting efficiency of the organic light emitting device of the present invention (organic light emitting devices 1 and 2) is significantly higher than that of the light emitting devices (organic light emitting devices 3 and 4) having no intermediate layer.
Claims (4)
−ＣＯ−Ｒ
（１）
［式（１）中、Ｒはアルキル基、アルコキシ基またはヒドロキシル基を表す。］ A light emitting layer containing a polymer compound is provided between the cathode and the anode, and the number average molecular weight in terms of polystyrene is 1 × 10 3 or more between the anode and the light emitting layer, and is represented by the formula (1). The organic light emitting element which has the intermediate | middle layer which contains the aliphatic compound which has a group and contacts this light emitting layer.
-CO-R
(1)
[In Formula (1), R represents an alkyl group, an alkoxy group, or a hydroxyl group. ]
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| JPH08190986A (en) * | 1995-01-06 | 1996-07-23 | Sumitomo Chem Co Ltd | Organic electroluminescent device |
| US5853905A (en) * | 1997-09-08 | 1998-12-29 | Motorola, Inc. | Efficient single layer electroluminescent device |
| JP2006186269A (en) * | 2004-12-28 | 2006-07-13 | Tdk Corp | Organic el element and its manufacture |
| JP2007287623A (en) * | 2006-04-20 | 2007-11-01 | Dainippon Printing Co Ltd | Method for manufacturing organic electroluminescence element |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08190986A (en) * | 1995-01-06 | 1996-07-23 | Sumitomo Chem Co Ltd | Organic electroluminescent device |
| US5853905A (en) * | 1997-09-08 | 1998-12-29 | Motorola, Inc. | Efficient single layer electroluminescent device |
| JP2006186269A (en) * | 2004-12-28 | 2006-07-13 | Tdk Corp | Organic el element and its manufacture |
| JP2007287623A (en) * | 2006-04-20 | 2007-11-01 | Dainippon Printing Co Ltd | Method for manufacturing organic electroluminescence element |
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