JPH10168443A - Phenylcarbazole derivative used for hole or electron transport layer of organic luminescent element - Google Patents
Phenylcarbazole derivative used for hole or electron transport layer of organic luminescent elementInfo
- Publication number
- JPH10168443A JPH10168443A JP8336653A JP33665396A JPH10168443A JP H10168443 A JPH10168443 A JP H10168443A JP 8336653 A JP8336653 A JP 8336653A JP 33665396 A JP33665396 A JP 33665396A JP H10168443 A JPH10168443 A JP H10168443A
- Authority
- JP
- Japan
- Prior art keywords
- transport layer
- hole
- electron transport
- phenylcarbazole
- carbazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- H10K85/649—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
-
- 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
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、電子材料、例えば
有機発光素子の正孔輸送層または電子輸送層等に用いる
のに適したフェニルカルバゾール誘導体に関する。[0001] The present invention relates to a phenylcarbazole derivative suitable for use in an electronic material, for example, a hole transport layer or an electron transport layer of an organic light emitting device.
【０００２】[0002]
【従来の技術】陰極から注入された電子と陽極から注入
された正孔が、両極に挟まれた有機蛍光体内で再結合す
る際に光を発する有機発光素子は古くから知られている
が、近年、有機発光層を挟んでその両側に電子輸送層と
正孔輸送層を積層したダブルヘテロ構造の素子が開発さ
れており、このダブルヘテロ構造の有機発光素子は、幅
広い応用の可能性を持つものとして注目されている。こ
のダブルヘテロ構造の有機発光素子においては、その正
孔または電子輸送層を形成する輸送材料は素子特性を左
右するために、特に重要な材料となる。2. Description of the Related Art An organic light emitting device that emits light when electrons injected from a cathode and holes injected from an anode recombine in an organic phosphor sandwiched between both electrodes has been known for a long time. In recent years, a double heterostructure device in which an electron transport layer and a hole transport layer are stacked on both sides of an organic light-emitting layer has been developed, and this double heterostructure organic light-emitting device has wide application potential. It has been attracting attention. In the organic light-emitting device having the double hetero structure, the transport material forming the hole or electron transport layer is a particularly important material because it affects the device characteristics.
【０００３】このようなキャリア輸送材料としては、ト
リフェニルアミン系化合物やオキサゾール誘導体等が代
表的に知られている。そして、これらの輸送材料は、有
機発光層の両側に真空蒸着法や溶液塗布法等によって薄
膜化されて形成され、更に陽極および陰極で直接または
間接的に挟持することによって、正孔または電子輸送層
を構成する。[0003] As such a carrier transporting material, triphenylamine compounds, oxazole derivatives and the like are typically known. These transport materials are formed on both sides of the organic light-emitting layer in a thin film by a vacuum deposition method or a solution coating method, and are directly or indirectly sandwiched between an anode and a cathode to transport holes or electrons. Make up the layers.
【０００４】[0004]
【発明が解決しようとする課題】ところで、以上のよう
な従来の輸送材料においては、膜厚の問題、および電子
のブロッキング等に起因して、電流を増加させなければ
発光効率が低く、また、合成しにくいという欠点があ
る。By the way, in the conventional transport materials as described above, the luminous efficiency is low unless the current is increased due to the problem of the film thickness and the blocking of electrons. There is a disadvantage that it is difficult to synthesize.
【０００５】例えば、低分子有機物質においてはＴＰＤ
（トリフェニルジアミン）等、比較的高性能を発現する
キャリア輸送材料が知られているが、素子の性能が低下
しやすく、また、合成が煩雑である点が指摘されてい
る。また、オキサゾール誘導体では、膜厚を薄くできる
ものの、薄膜の安定性に問題があり、発光効率が低いと
いう欠点があって、有機発光素子のキャリア輸送層とし
ては有効な効果を期待することはできない。For example, in the case of low molecular weight organic substances, TPD
Although carrier transporting materials that exhibit relatively high performance, such as (triphenyldiamine), are known, it is pointed out that the performance of the device is liable to decrease and the synthesis is complicated. Further, although the oxazole derivative can be reduced in film thickness, it has a problem in stability of the thin film and has a disadvantage of low luminous efficiency, so that an effective effect cannot be expected as a carrier transport layer of an organic light emitting device. .
【０００６】更に、大きな問題として、前記したトリフ
ェニルアミン系の輸送材料は、ガラス転移点が低く、そ
れを改善する必要があるばかりでなく、窒素原子の結合
しているフェニル環がトライアングル構造を示し、平面
構造になっていない。それ故に、窒素原子の余剰の電子
（または電荷）、過不足の電荷を生じたＥＬ電荷、ある
いは正孔輸送時に芳香環に電子を流しにくく、共鳴安定
化が期待できない構造になっているという欠点があっ
た。[0006] Further, as a major problem, the above-mentioned triphenylamine-based transport material has a low glass transition point, and it is necessary not only to improve it, but also the phenyl ring to which a nitrogen atom is bonded has a triangle structure. Shown, not a planar structure. Therefore, a surplus electron (or charge) of a nitrogen atom, an EL charge having an excess or deficiency of charge, or a difficulty in flowing an electron to an aromatic ring during hole transport, resulting in a structure in which resonance stabilization cannot be expected. was there.
【０００７】本発明はこのような実情に鑑みてなされた
もので、キャリア輸送層をはじめとする電子材料、特に
有機発光素子の正孔または電子輸送層に用いて、発光効
率が良好で、安定性に富み、しかも合成が容易なフェニ
ルカルバゾール誘導体の提供を目的としている。The present invention has been made in view of such circumstances, and is used for an electron material such as a carrier transport layer, in particular, for a hole or electron transport layer of an organic light emitting device, and has a good luminous efficiency and a stable luminous efficiency. An object of the present invention is to provide a phenylcarbazole derivative that is rich in properties and easy to synthesize.
【０００８】[0008]
【課題を解決するための手段】上記の目的を達成するた
め、請求項１の発明のフェニルカルバゾール誘導体は、
有機発光素子の正孔または電子輸送層等に用いられるフ
ェニルカルバゾール誘導体であって、カルバゾール環と
ベンゼン環とが結合したフェニルカルバゾール誘導体か
らなり、かつ、そのフェニルカルバゾール誘導体が下記
の一般式（１）で表されるユニットの複数によって構成
されていることを特徴としている。In order to achieve the above object, the phenylcarbazole derivative according to the first aspect of the present invention comprises:
A phenylcarbazole derivative used for a hole or electron transport layer or the like of an organic light emitting device, the phenylcarbazole derivative comprising a carbazole ring and a benzene ring bonded to each other, and the phenylcarbazole derivative is represented by the following general formula (1) Is characterized by being constituted by a plurality of units represented by.
【０００９】[0009]
【化３】 Embedded image
【００１０】また、同じ目的を達成するため、請求項２
の発明のフェニルカルバゾール誘導体は、下記の一般式
（２）で表されるユニットの複数によって構成されてい
ることを特徴としている。[0010] In order to achieve the same object, a second aspect is provided.
The phenylcarbazole derivative according to the invention is characterized by comprising a plurality of units represented by the following general formula (2).
【００１１】[0011]
【化４】 Embedded image
【００１２】一般式（１）または（２）で表されるユニ
ットからなる化合物である本発明のフェニルカルバゾー
ル誘導体においては、ベンゼン環に重複部分がなく、平
面構造を有しており、共鳴安定化して構成されることに
なる。従って、窒素原子の不対電子が、隣接するフェニ
ル基およびカルバゾール基に電子まはた正電荷の一部を
流れやすくするように配置されることになる。The phenylcarbazole derivative of the present invention, which is a compound comprising the unit represented by the general formula (1) or (2), has no overlapping portion in the benzene ring, has a planar structure, and has resonance stabilization. Will be configured. Therefore, the unpaired electrons of the nitrogen atom are arranged so as to easily flow a part of the electrons or the positive charges to the adjacent phenyl group and carbazole group.
【００１３】このような本発明のフェニルカルバゾール
誘導体の構造的な特徴とそれによってもたらされる機能
は、キャリア輸送材料、例えば電子輸送材料において
は、電界を与えられた電極間において陰極からの電子を
効率よく輸送することが必要で、電子の注入効率が高
く、注入された電子を効率よく輸送することが好まし
い、という条件に合致し、有機発光素子の正孔または電
子輸送層として用いた場合には、発光効率が高く、安定
性に富んで機能の劣化が少ないという目的を達成するこ
とが可能となる。The structural features of the phenylcarbazole derivative of the present invention and the functions provided thereby are as follows. In a carrier transporting material, for example, an electron transporting material, the efficiency of electrons from a cathode between electrodes to which an electric field is applied is improved. It is necessary to transport well, the electron injection efficiency is high, it is preferable to transport the injected electrons efficiently, and when used as a hole or electron transport layer of an organic light emitting device, It is possible to achieve the object of high luminous efficiency, high stability and little deterioration of the function.
【００１４】そして、以上のような本発明のフェニルカ
ルバゾール誘導体は、溶媒としてのο（オルト）−ジク
ロルベンゼンを用いてカルバゾールと反応後濾過するこ
とにより無機物を除去し、更に減圧濃縮して固形物を取
り出し、ベンゼン等で再結晶させることにより精製する
ことで、比較的簡単に得ることができる。The phenylcarbazole derivative of the present invention as described above is reacted with carbazole using o (ortho) -dichlorobenzene as a solvent, and then filtered to remove inorganic substances. The product can be obtained relatively easily by taking out the product and purifying it by recrystallization with benzene or the like.
【００１５】本発明のフェニルカルバゾール誘導体は、
有機発光素子の正孔輸送層または電子輸送層として用い
て特に上記した目的効果を達成するものであるが、本発
明を適用する有機発光素子の構造としては、ダブルヘテ
ロ構造のもののほか、発光層と電子輸送層を備えた構造
の素子、あるいは電子輸送層のみの素子であってもよ
い。The phenylcarbazole derivative of the present invention comprises
The organic light-emitting device achieves the above-described effects by using it as a hole-transport layer or an electron-transport layer of an organic light-emitting device. An element having a structure provided with an electron transport layer and an element having only an electron transport layer may be used.
【００１６】本発明のフェニルカルバゾール誘導体は、
前記一般式（１）または（２）で表されるユニットから
なるものであり、その具体的なユニットの構造または配
列は、後述の各実施例で示されるＤＣＢＰやＤＣＴＰの
ほかに、一般式（１）で示されるユニットを基本系とし
た例としては、下記の式（３）や（４）式で示される配
列を挙げることができる。また、一般式（２）で表され
るユニットを基本系としたものについても、ｎが２以上
であれば任意の配列を採ることができ、本発明において
は、要は一般式（１）または（２）で表されるユニット
からなるものであれば、その配列は問わない。The phenylcarbazole derivative of the present invention comprises
It comprises a unit represented by the general formula (1) or (2), and the specific structure or arrangement of the unit is, in addition to DCBP and DCTP shown in each embodiment described later, a general formula ( As an example in which the unit represented by 1) is used as a basic system, an array represented by the following formulas (3) and (4) can be given. In addition, a unit having a unit represented by the general formula (2) as a basic system can have an arbitrary arrangement as long as n is 2 or more. In the present invention, the general formula (1) The arrangement is not limited as long as it is composed of the unit represented by (2).
【００１７】[0017]
【化５】 Embedded image
【００１８】[0018]
【化６】 Embedded image
【００１９】[0019]
【実施例】以下、本発明に係るフェニルカルバゾール誘
導体の具体的な構造並びにその製造方法、および機能に
ついて詳しく述べる。EXAMPLES The specific structure of the phenylcarbazole derivative according to the present invention, its production method and its function will be described in detail below.
【００２０】＜実施例１＞下記の式（５）で表される
４，４−ジカルボゾリルビフェニルジアミン（ＤＣＢ
Ｐ）・・Ｃ36Ｈ24Ｎ2 について述べる。<Example 1> 4,4-dicarbazolylbiphenyldiamine (DCB) represented by the following formula (5)
P)... C 36 H 24 N 2 will be described.
【００２１】[0021]
【化７】 Embedded image
【００２２】このＤＣＢＰは、溶媒としてο−ジクロル
ベンゼンを用い、カルバゾールと反応させた後に、再結
晶させることによって得ることができる。この実施例１
においては、ο−ジクロルベンゼンとカルバゾールのほ
かに、炭酸カリウム、Ｃｕ粉末、および１８−クラウン
−６−エーテルを用い、これらを順に２５ｇ：２１．６
２ｇ：１７．８７ｇ：０．６６ｇ：５．４３ｇの質量比
（モル比では１：２．１：２．１：１／６：１／３とな
る）のもとに配合し、１９５°Ｃの窒素雰囲気下で２４
時間反応させた。This DCBP can be obtained by using o-dichlorobenzene as a solvent, reacting it with carbazole, and then recrystallizing it. Example 1
In addition to o-dichlorobenzene and carbazole, potassium carbonate, Cu powder, and 18-crown-6-ether were used in the order of 25 g: 21.6.
Formulated under a mass ratio of 2g: 17.87g: 0.66g: 5.43g (molar ratio is 1: 2.1: 2.1: 1/6: 1/3), 195 ° C 24 under nitrogen atmosphere
Allowed to react for hours.
【００２３】反応終了後、完全に溶媒を飛ばしてから脱
水ベンゼン中で約５回再結晶させ、真空乾燥させること
により、式（５）で示されるＤＣＢＰを５０〜６０％の
収率で得ることができた。得られたＤＣＢＰは融点２８
４．６６°Ｃであり、元素分析結果は次の〔表１〕の通
りであった。After completion of the reaction, the solvent is completely removed, then recrystallized about 5 times in dehydrated benzene, and dried under vacuum to obtain a DCBP represented by the formula (5) in a yield of 50 to 60%. Was completed. The obtained DCBP has a melting point of 28.
4.66 ° C., and the results of elemental analysis were as shown in [Table 1].
【００２４】[0024]
【表１】 [Table 1]
【００２５】このようにして得られたＤＣＢＰは、図１
に模式的に示すように、カルバゾール環とベンゼン環と
が相互に結合したユニットからなり、ベンゼン環部分に
おける重複部分がないので、平面構造で結びついている
が故に共鳴安定化した構造であって、窒素原子の不対電
子が隣接したフェニル基およびカルバゾール基に電子ま
たは正電荷の一部を流れやすくするように配置されるこ
とになる。The DCBP thus obtained is shown in FIG.
As schematically shown in FIG. 2, the carbazole ring and the benzene ring are composed of units bonded to each other, and there is no overlapping portion in the benzene ring portion. An unpaired electron of the nitrogen atom is arranged so as to facilitate a part of the electron or positive charge to the adjacent phenyl group and carbazole group.
【００２６】また、この実施例で得たＤＣＢＰと、従来
のＴＰＤ（トリフェニルジアミン）との発光特性の比較
結果を図２に示す。この図２は、下記の〔表２〕に示す
ように、厚さ１ｍｍのガラス基板の上に、ＭｇまたはＡ
ｌ−Ｌｉからなる陰極金属（厚さ１５００Å）、Ａｌｑ
３（アルミキノリノール鎖体、厚さ５００Å）からなる
電子輸送層、ＤＣＢＰまたはＴＰＤからなる正孔輸送層
（厚さ５００Å）、ＩＴＯからなる陽極（厚さ１０００
Å）を積層形成した各素子において、電極間に流れる電
流密度を種々に変化させたときの発光輝度の測定結果を
示すグラフである。FIG. 2 shows the results of a comparison of the light emission characteristics of DCBP obtained in this example and conventional TPD (triphenyldiamine). FIG. 2 shows that, as shown in Table 2 below, Mg or A was placed on a glass substrate having a thickness of 1 mm.
Cathode metal of l-Li (thickness 1500 °), Alq
3 (aluminum quinolinol chain, thickness 500 mm), a hole transport layer made of DCBP or TPD (thickness 500 mm), and an anode made of ITO (thickness 1000 mm)
7 is a graph showing the measurement results of the emission luminance when the current density flowing between the electrodes is variously changed in each of the devices formed by laminating 積 層).
【００２７】[0027]
【表２】 [Table 2]
【００２８】図２から明らかなように、ＤＣＢＰの発光
輝度がＴＰＤに比して優れていることが確認された。従
って、このＤＣＢＰは、有機発光素子のキャリア輸送材
料として使用するのに適していることが実証された。As is clear from FIG. 2, it was confirmed that the emission luminance of DCBP was superior to that of TPD. Therefore, it was proved that this DCBP was suitable for use as a carrier transporting material of an organic light emitting device.
【００２９】また、この実施例によって得られたＤＣＢ
Ｐの特性を示すために、Ｈ−ＮＭＲ分析結果（化学シフ
ト）と赤外分光分析結果をそれぞれ図３と図４に示す。 ＜実施例２＞下記の式（６）で表される４，４−ジカル
ボゾリルトリフェニルジアミン（ＤＣＴＰ）・・Ｃ42Ｈ28
Ｎ2 について述べる。Further, the DCB obtained by this embodiment
In order to show the characteristics of P, the results of H-NMR analysis (chemical shift) and the results of infrared spectroscopy are shown in FIGS. 3 and 4, respectively. <Example 2> The following 4,4-dicarboxylic Bozori Le triphenyl diamine represented by the formula (6) (DCTP) ·· C 42 H 28
Describe N 2.
【００３０】[0030]
【化８】 Embedded image
【００３１】このＤＣＴＰは、実施例１のＤＣＢＰと同
様、溶媒としてのο−ジクロルベンゼンを用いてカルバ
ゾールと反応させた後に、再結晶させて得ることができ
る。この例においては、その反応に際しては、ＤＣＢＰ
と同様にο−ジクロルベンゼンおよびカルバゾールのほ
かに炭酸カリウム、Ｃｕ粉末および１８−クラウン−６
−エーテルを配合するが、その配合割合は、上記の順に
重量比２．７ｇ：１．９７ｇ：１．８７ｇ：０．０６
ｇ：０．４９３ｇ（モル比では実施例１のＤＣＢＰと同
様に１：２．１：２．１：１／３：１／６）とし、１９
５°Ｃの窒素雰囲気下で２４時間反応させた。This DCTP can be obtained by reacting with carbazole using o-dichlorobenzene as a solvent and recrystallizing the same as in DCBP of Example 1. In this example, the reaction involved DCBP
In addition to ο-dichlorobenzene and carbazole, potassium carbonate, Cu powder and 18-crown-6
-The compounding ratio of the ether is 2.7 g: 1.97 g: 1.87 g: 0.06 in the order described above.
g: 0.493 g (1: 2.1: 2.1: 1/3: 1/6 in molar ratio as in the case of DCBP of Example 1), and
The reaction was performed under a nitrogen atmosphere at 5 ° C. for 24 hours.
【００３２】反応終了後に、完全に溶媒を飛ばしてから
脱水ベンゼン中で約５回再結晶させ、真空乾燥させるこ
とにより、式（６）で示されるＤＣＴＰを約３０％の収
率で得た。得られたＤＣＴＰは融点３２１．０°Ｃであ
り、元素分析結果は〔表３〕に示す通りであった。After completion of the reaction, the solvent was completely removed, recrystallized about 5 times in dehydrated benzene, and dried under vacuum to obtain DCTP represented by the formula (6) in a yield of about 30%. The obtained DCTP had a melting point of 321.0 ° C., and the results of elemental analysis were as shown in [Table 3].
【００３３】[0033]
【表３】 [Table 3]
【００３４】以上のようにして得られたＤＣＴＰも、実
施例１のＤＣＢＰと同様に、カルバゾール環とベンゼン
環とが相互に結合した構造のユニットからなり、ベンゼ
ン環部分での重複部分がなく、平面構造であるため、共
鳴安定化した構造であって、有機発光素子のキャリア輸
送層として有用に使用することができる。The DCTP obtained as described above, like the DCBP of Example 1, is composed of a unit having a structure in which a carbazole ring and a benzene ring are bonded to each other, and has no overlapping portion in the benzene ring portion. Since it has a planar structure, it has a resonance-stabilized structure and can be usefully used as a carrier transport layer of an organic light-emitting device.
【００３５】また、以上のようにして得たＤＣＴＰの特
性を示すために、Ｈ−ＮＭＲ分析結果（化学シフト）お
よび赤外分光分析結果をそれぞれ図５および図６に示
す。FIGS. 5 and 6 show the results of H-NMR analysis (chemical shift) and infrared spectroscopy, respectively, to show the characteristics of DCTP obtained as described above.
【００３６】[0036]
【発明の効果】以上のように、本発明のフェニルカルバ
ゾール誘導体は、フェニル基とカルバゾール基とが直接
結合したユニットの複数からなり、しかもそのユニット
内において、また、ユニットどうしにおいても、ベンゼ
ン環部分において重複部分がなく、平面構造を有して共
鳴安定化した構成であるが故に、窒素原子の不対電子が
隣接のフェニル基およびカルバゾール基に電子または正
電荷の一部が流れやすくなるように配置されることにな
り、キャリアの輸送材料として極めて有用な材料とな
る。As described above, the phenylcarbazole derivative of the present invention comprises a plurality of units in which a phenyl group and a carbazole group are directly bonded, and furthermore, within the units and between the units, the benzene ring moiety Because there is no overlap in the structure and the structure is resonance-stabilized with a planar structure, the unpaired electrons of the nitrogen atom make it easier for some of the electrons or positive charges to flow to the adjacent phenyl group and carbazole group. Thus, the material is extremely useful as a carrier transporting material.
【００３７】また、合成が容易で薄膜化することも可能
であることから、特に有機発光素子の正孔または電子輸
送層に用いた場合、従来のＴＰＤを用いる場合に比し
て、発光効率が高く、安定性に富み、しかも安価な素子
が得られる。In addition, since it is easy to synthesize and can be made into a thin film, the luminous efficiency is particularly higher when used for the hole or electron transport layer of an organic light emitting device than when a conventional TPD is used. A high-cost, highly stable, and inexpensive device can be obtained.
【図１】本発明の実施例１で得たＤＣＢＰの模式的構造
説明図FIG. 1 is a schematic structural explanatory view of DCBP obtained in Example 1 of the present invention.
【図２】本発明の実施例１で得たＤＣＢＰと、比較例と
してのＴＰＤの発光特性を比較するためのグラフFIG. 2 is a graph for comparing the light emission characteristics of DCBP obtained in Example 1 of the present invention and TPD as a comparative example.
【図３】本発明の実施例１で得たＤＣＢＰのＨ−ＮＭＲ
分析結果を示すグラフFIG. 3 is an H-NMR of DCBP obtained in Example 1 of the present invention.
Graph showing analysis results
【図４】本発明の実施例１で得てＤＣＢＰの赤外分光分
析結果を示すグラフFIG. 4 is a graph showing the results of infrared spectroscopic analysis of DCBP obtained in Example 1 of the present invention.
【図５】本発明の実施例２で得たＤＣＴＰのＨ−ＮＭＲ
分析結果を示すグラフFIG. 5: H-NMR of DCTP obtained in Example 2 of the present invention
Graph showing analysis results
【図６】本発明の実施例２で得たＤＣＴＰの赤外分光分
析結果を示すグラフFIG. 6 is a graph showing the results of infrared spectroscopic analysis of DCTP obtained in Example 2 of the present invention.
Claims (2)
に用いられる電子材料であって、カルバゾール環とベン
ゼン環とが結合したフェニルカルバゾール誘導体からな
り、かつ、このフェニルカルバゾール誘導体が下記の一
般式（１）で表されるユニットの複数によって構成され
ていることを特徴とする、有機発光素子の正孔または電
子輸送層等に用いられるフェニルカルバゾール誘導体。 【化１】 1. An electronic material used for a hole or electron transport layer or the like of an organic light-emitting device, comprising a phenylcarbazole derivative in which a carbazole ring and a benzene ring are bonded, and wherein the phenylcarbazole derivative has the following general formula: A phenylcarbazole derivative used for a hole or electron transport layer or the like of an organic light-emitting device, comprising a plurality of units represented by the formula (1). Embedded image
に用いられる電子材料であって、カルバゾール環とベン
ゼン環とが結合したフェニルカルバゾール誘導体からな
り、かつ、このフェニルカルバゾール誘導体が下記の一
般式（２）で表されるユニットの複数によって構成され
ていることを特徴とする、有機発光素子の正孔または電
子輸送層等に用いられるフェニルカルバゾール誘導体。 【化２】 2. An electronic material used for a hole or electron transport layer or the like of an organic light-emitting device, comprising a phenylcarbazole derivative in which a carbazole ring and a benzene ring are bonded, and wherein the phenylcarbazole derivative has the following general formula: A phenylcarbazole derivative used for a hole or electron transport layer or the like of an organic light-emitting device, comprising a plurality of units represented by the formula (2). Embedded image
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8336653A JPH10168443A (en) | 1996-12-17 | 1996-12-17 | Phenylcarbazole derivative used for hole or electron transport layer of organic luminescent element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8336653A JPH10168443A (en) | 1996-12-17 | 1996-12-17 | Phenylcarbazole derivative used for hole or electron transport layer of organic luminescent element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10168443A true JPH10168443A (en) | 1998-06-23 |
Family
ID=18301401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8336653A Pending JPH10168443A (en) | 1996-12-17 | 1996-12-17 | Phenylcarbazole derivative used for hole or electron transport layer of organic luminescent element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH10168443A (en) |
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