JP4915279B2 - Light emitting element - Google Patents
Light emitting element Download PDFInfo
- Publication number
- JP4915279B2 JP4915279B2 JP2007137136A JP2007137136A JP4915279B2 JP 4915279 B2 JP4915279 B2 JP 4915279B2 JP 2007137136 A JP2007137136 A JP 2007137136A JP 2007137136 A JP2007137136 A JP 2007137136A JP 4915279 B2 JP4915279 B2 JP 4915279B2
- Authority
- JP
- Japan
- Prior art keywords
- light emitting
- group
- derivatives
- light
- transport layer
- 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.)
- Expired - Fee Related
Links
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- -1 nitrogen-containing aromatic compound Chemical class 0.000 claims description 19
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 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
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- ZRXVCYGHAUGABY-UHFFFAOYSA-O tris(4-bromophenyl)azanium Chemical compound C1=CC(Br)=CC=C1[NH+](C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 ZRXVCYGHAUGABY-UHFFFAOYSA-O 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
Description
本発明は、電気エネルギーを光に変換できる発光素子に関する。 The present invention relates to a light emitting element capable of converting electric energy into light.
有機発光素子は、陽極と陰極との間に有機発光層を備える。陰極から注入された電子と陽極から注入された正孔とが有機発光層内で再結合する際に、発光化合物の励起子を発生させ、この励起子が基底状態に戻る際に光を発生する。 The organic light emitting device includes an organic light emitting layer between an anode and a cathode. When electrons injected from the cathode and holes injected from the anode recombine in the organic light emitting layer, they generate excitons of the luminescent compound, and light is generated when these excitons return to the ground state. .
１９８７年に、コダック社のＣ．Ｗ．Ｔａｎｇらが、有機薄膜発光素子が高輝度に発光することを開示した（非特許文献１参照）。この文献には、ＩＴＯガラス基板上に、ジアミン化合物を正孔輸送層に、トリス（８−キノリノラート）アルミニウム（ＩＩＩ）を発光層に、Ｍｇ：Ａｇを陰極とした有機薄膜発光素子が開示されている。この有機薄膜発光素子は、１０Ｖ程度の駆動電圧で１，０００ｃｄ／ｍ２の緑色発光することが報告されている。 In 1987, Kodak's C.I. W. Tang et al. Disclosed that an organic thin film light emitting device emits light with high luminance (see Non-Patent Document 1). This document discloses an organic thin-film light-emitting device having an diamine compound as a hole transport layer, tris (8-quinolinolato) aluminum (III) as a light-emitting layer, and Mg: Ag as a cathode on an ITO glass substrate. Yes. This organic thin film light emitting element has been reported to emit green light of 1,000 cd / m 2 at a driving voltage of about 10V.
このような有機発光素子は、薄型であり、かつ低駆動電圧であっても高輝度に発光し、発光材料を選択することで多色発光が可能である。このため、ディスプレイなどへの応用が期待され、有機発光素子の研究・開発が活発に行われている。特に、実用化の観点から、素子の発光効率の向上、低駆動電圧化、発光寿命の向上を図る必要がある。 Such an organic light emitting element is thin and emits light with high luminance even at a low driving voltage, and multicolor light emission is possible by selecting a light emitting material. For this reason, application to a display etc. is anticipated, and research and development of an organic light emitting element are actively performed. In particular, from the viewpoint of practical use, it is necessary to improve the light emission efficiency of the device, lower the driving voltage, and improve the light emission lifetime.
素子の発光効率を支配する因子としては、電子と正孔の注入バランス因子（キャリアバランス）、キャリア再結合による発光性励起子の生成効率、発光量子効率が重要であることが知られている（非特許文献２参照）。 It is known that the factors that govern the light emission efficiency of the device are the electron and hole injection balance factor (carrier balance), the generation efficiency of luminescent excitons by carrier recombination, and the light emission quantum efficiency ( Non-patent document 2).
また、キャリア（電子、正孔）の移動度が高ければ、低駆動電圧化を向上させることができる。このため、高キャリア移動度を有する電子輸送材料や正孔輸送材料が開発されている。高キャリア移動度を有する電子輸送材料として、オキサジアゾール誘導体、トリアゾール誘導体（非特許文献３参照）や、フェナントロリン誘導体（特許文献１および特許文献２参照）など数多くの材料が開発されている。一方、高キャリア移動度を有する正孔輸送材料としては芳香族アミン化合物を中心とした材料が開発されており、これらが多く用いられている（非特許文献４，特許文献３および特許文献４参照）。
しかし、上記文献に記載された材料を用いても、発光素子の高効率化、低駆動電圧化および長寿命化のいずれにおいても充分なレベルに達していない。特に、低駆動電圧化と長寿命化とを備えた発光素子を得るためには、更なる改善が望まれている。 However, even if the materials described in the above-mentioned documents are used, the light emitting element has not reached a sufficient level in any of high efficiency, low driving voltage and long life. In particular, in order to obtain a light emitting device having a low driving voltage and a long life, further improvement is desired.
本発明は、上記問題に鑑みなされたものであり、その目的は、発光効率、低駆動電圧化、発光寿命が向上された発光素子を提供することにある。 The present invention has been made in view of the above problems, and an object of the present invention is to provide a light-emitting element with improved light emission efficiency, lower drive voltage, and light emission lifetime.
すなわち、本発明は以下のとおりである。
本発明は、陽極と陰極との間に、少なくとも正孔輸送層と発光層とを有する発光素子であって、前記正孔輸送層は、下記一般式（１）で表される化合物を含有する、発光素子である。
（Ｒ１〜Ｒ６は、それぞれ同一であっても、異なっていてもよく、水素、アルキル基、シクロアルキル基、アリール基を表す。Ａは、単結合、アリーレン基、ヘテロアリーレン基を表す。Ａｒ１〜Ａｒ３は、それぞれ同一であっても、異なっていてもよい、アリール基である。Ａｒ２−Ｎ−Ａｒ３は、縮合して環を形成していてもよい。）
That is, the present invention is as follows.
The present invention is a light emitting device having at least a hole transport layer and a light emitting layer between an anode and a cathode, and the hole transport layer contains a compound represented by the following general formula (1). , A light emitting element.
(R 1 to R 6 may be the same or different and each represents hydrogen, an alkyl group, a cycloalkyl group, or an aryl group. A represents a single bond, an arylene group, or a heteroarylene group. Ar 1 to Ar 3 are each an aryl group which may be the same or different, and Ar 2 —N—Ar 3 may be condensed to form a ring.
上記一般式（１）で表される化合物は、高い正孔輸送能を有する。このため、上記一般式（１）で表される化合物を正孔輸送層に用いると、駆動電圧を低下させた発光素子を提供することができる。 The compound represented by the general formula (1) has a high hole transport ability. For this reason, when the compound represented by the general formula (1) is used for the hole transport layer, a light-emitting element with a reduced driving voltage can be provided.
また、上記発光素子は、上記陰極と上記発光層との間に、少なくとも電子輸送層を有し、
上記電子輸送層は、不対電子対を有する含窒素芳香族化合物を含有するものであるとよい。
Further, the light emitting element has at least an electron transport layer between the cathode and the light emitting layer,
The electron transport layer may contain a nitrogen-containing aromatic compound having an unpaired electron pair.
上記したように発光効率を向上させるためには、電子と正孔の注入バランス因子（キャリアバランス）が重要となる。高い正孔輸送能を有する上記一般式（１）で表される化合物と、キャリアバランスをとるためには、電子輸送能の高い電子輸送層を設ければよい。不対電子対を有する含窒素芳香族化合物を含有するものは、電子輸送能が高いので、キャリアバランスをとることができる。この結果、発光効率の向上した発光素子を得ることができる。 As described above, in order to improve the light emission efficiency, an injection balance factor (carrier balance) of electrons and holes is important. In order to achieve a carrier balance with the compound represented by the general formula (1) having a high hole transport capability, an electron transport layer having a high electron transport capability may be provided. Those containing a nitrogen-containing aromatic compound having an unpaired electron pair have a high electron transporting ability, so that carrier balance can be achieved. As a result, a light emitting element with improved luminous efficiency can be obtained.
本発明の発光素子では、高い正孔輸送能を有する化合物を正孔輸送層に用いる。この結果、発光素子の低駆動電圧化を図ることができる。 In the light emitting device of the present invention, a compound having a high hole transport ability is used for the hole transport layer. As a result, the driving voltage of the light emitting element can be reduced.
さらに、電子輸送層を設ける場合に、電子輸送能の高い化合物を用いる。この結果、発光効率の向上した発光素子を得ることができる。 Further, when an electron transport layer is provided, a compound having a high electron transport ability is used. As a result, a light emitting element with improved luminous efficiency can be obtained.
以下に本発明を詳細に説明する。本発明の発光素子は、陽極と、陰極と、これらの電極間に、少なくとも、正孔輸送層と発光層とを、この順に備えている。また、本発明の発光素子は、陽極と、陰極と、これらの電極間に、少なくとも、正孔輸送層と発光層と電子輸送層とをこの順に備えていてもよい。 The present invention is described in detail below. The light-emitting element of the present invention includes an anode, a cathode, and at least a hole transport layer and a light-emitting layer in this order between these electrodes. In addition, the light-emitting element of the present invention may include an anode, a cathode, and at least a hole transport layer, a light-emitting layer, and an electron transport layer in this order between these electrodes.
［基板］
本発明の発光素子は、基板上に形成されていると、機械的強度を保てるので好ましい。基板としては、ソーダガラスや無アルカリガラスなどのガラス基板が好適に用いられる。ガラス基板の厚みは、機械的強度を保つのに十分な厚みがあればよいので、０．５ｍｍ以上あれば十分である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、ＳｉＯ２などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することもできる。
[substrate]
The light emitting device of the present invention is preferably formed on a substrate because the mechanical strength can be maintained. As the substrate, a glass substrate such as soda glass or non-alkali glass is preferably used. As the thickness of the glass substrate, it is sufficient that the thickness is sufficient to maintain the mechanical strength. The glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass, but soda lime glass with a barrier coat such as SiO 2 is also available on the market. it can.
さらに、基板上に形成される電極（特に、陽極）が安定に機能するのであれば、基板はガラスである必要はなく、例えば、プラスチック基板上に陽極を形成してもよい。 Furthermore, if the electrode (particularly the anode) formed on the substrate functions stably, the substrate does not have to be glass. For example, the anode may be formed on a plastic substrate.
［陽極］
本発明の発光素子に用いられる陽極の材料としては、正孔を有機層に効率よく注入できる材料であれば特に限定されない。好ましくは、比較的仕事関数の大きい材料である。例えば、酸化亜鉛、酸化錫、酸化インジウム、酸化亜鉛インジウム、酸化錫インジウム（ＩＴＯ）などの導電性金属酸化物、金、銀、クロムなどの金属、ヨウ化銅、硫化銅などの無機導電性物質、あるいはポリチオフェン、ポリピロールおよびポリアニリンなどの導電性ポリマーなどが挙げられる。これらの陽極電極材料は、単独で用いてもよく、複数の材料を混合して用いてもよい。また、陽極は一層構成でもよく、多層構成としてもよい。
[anode]
The material for the anode used in the light emitting device of the present invention is not particularly limited as long as it can efficiently inject holes into the organic layer. A material having a relatively high work function is preferable. For example, conductive metal oxides such as zinc oxide, tin oxide, indium oxide, indium zinc oxide and indium tin oxide (ITO), metals such as gold, silver and chromium, inorganic conductive materials such as copper iodide and copper sulfide Or conductive polymers such as polythiophene, polypyrrole and polyaniline. These anode electrode materials may be used alone, or a plurality of materials may be mixed and used. The anode may have a single layer structure or a multilayer structure.
電極の抵抗は、発光素子の発光に十分な電流が供給できる程度であればよい。発光素子の消費電力の観点からは、低抵抗であることが望ましい。例えば、３００Ω／□以下のＩＴＯ基板であれば素子電極として機能するが、好ましくは１００Ω／□以下の低抵抗品を使用するとよい。ＩＴＯの厚みは抵抗値に合わせて任意に選ぶ事ができるが、通常１００〜３００ｎｍの間で用いられることが多い。 The resistance of the electrode may be such that a current sufficient for light emission of the light emitting element can be supplied. From the viewpoint of power consumption of the light emitting element, it is desirable that the resistance is low. For example, an ITO substrate of 300Ω / □ or less functions as a device electrode, but a low-resistance product of 100Ω / □ or less is preferably used. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually used in a range of 100 to 300 nm.
基板上に、陽極を形成する方法は特に制限はなく、公知の方法を用いればよい。例えば、陽極としてＩＴＯ膜を形成する場合には、電子線ビーム法、スパッタリング法、化学反応法などの方法で形成すればよい。 The method for forming the anode on the substrate is not particularly limited, and a known method may be used. For example, when an ITO film is formed as the anode, it may be formed by a method such as an electron beam method, a sputtering method, or a chemical reaction method.
［陰極］
本発明の発光素子に用いられる陰極の材料としては、電子を有機層に効率良く注入できる物質であれば特に限定されない。例えば、一般に白金、金、銀、銅、鉄、錫、亜鉛、アルミニウム、インジウム、クロム、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウムおよびこれらの合金などが挙げられる。電子注入効率をあげて素子特性を向上させるためには、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウムなどの低仕事関数金属、またはこれらを含む合金が好ましい。
[cathode]
The material for the cathode used in the light emitting device of the present invention is not particularly limited as long as it can efficiently inject electrons into the organic layer. For example, platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium, sodium, potassium, cesium, calcium, magnesium, and alloys thereof are generally used. In order to improve the device characteristics by increasing the electron injection efficiency, low work function metals such as lithium, sodium, potassium, cesium, calcium, and magnesium, or alloys containing these metals are preferable.
これらの低仕事関数金属は、一般に大気中で不安定であることが多く、取り扱いが困難である。このため、有機層に微量のリチウムやマグネシウム等の低仕事関数の金属、あるいはフッ化リチウムのような大気中で安定な低仕事関数の金属塩をドーピング（真空蒸着の膜厚計表示で１ｎｍ以下）した後に、電極保護のために白金、金、銀、銅、鉄、錫、アルミニウムおよびインジウムなどの大気中でより安定な金属を積層して陰極とする方法が好ましい。更にこれら金属を用いた合金、そしてシリカ、チタニアおよび窒化ケイ素などの無機物、ポリビニルアルコール、塩化ビニル、炭化水素系高分子化合物などを保護膜層として積層することが、好ましい例として挙げられる。これらの電極の作製法は、抵抗加熱、電子線ビーム、スパッタリング、イオンプレーティングおよびコーティングなど、特に制限されない。 These low work function metals are generally unstable in the atmosphere and are difficult to handle. For this reason, the organic layer is doped with a small amount of a low work function metal such as lithium or magnesium, or a metal salt with a low work function that is stable in the air, such as lithium fluoride (1 nm or less on the film thickness display of vacuum deposition) In order to protect the electrode, a method in which a more stable metal such as platinum, gold, silver, copper, iron, tin, aluminum, and indium is laminated in the atmosphere to form a cathode is preferable. Furthermore, it is preferable to stack an alloy using these metals, inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. as a protective film layer. The production method of these electrodes is not particularly limited, such as resistance heating, electron beam, sputtering, ion plating and coating.
［正孔輸送層］
正孔輸送層は、陽極から正孔が注入され、注入された正孔を輸送する層である。正孔輸送層の材料としては、陽極からの正孔の注入を容易にし、また注入された正孔を輸送する能力が高いことが要求される。本発明では、正孔輸送材料として、少なくとも下記一般式（１）で表される化合物を含有する。
ここで、Ｒ１〜Ｒ６は、それぞれ同一であっても、異なっていてもよく、水素、アルキル基、シクロアルキル基、アリール基を表す。Ａは、単結合、アリーレン基、ヘテロアリーレン基を表す。Ａｒ１〜Ａｒ３は、それぞれ同一であっても、異なっていてもよい、アリール基である。Ａｒ２−Ｎ−Ａｒ３は、縮合して環を形成していてもよい。
[Hole transport layer]
The hole transport layer is a layer in which holes are injected from the anode and transports the injected holes. The material for the hole transport layer is required to facilitate injection of holes from the anode and to have a high ability to transport the injected holes. In the present invention, the hole transport material contains at least a compound represented by the following general formula (1).
Here, R 1 to R 6 may be the same or different and each represents hydrogen, an alkyl group, a cycloalkyl group, or an aryl group. A represents a single bond, an arylene group, or a heteroarylene group. Ar 1 to Ar 3 are aryl groups which may be the same or different from each other. Ar 2 —N—Ar 3 may be condensed to form a ring.
（Ｒ１〜Ｒ６）
Ｒ１〜Ｒ６を構成するアルキル基としては、炭素数が１〜２０の、より好ましくは１以上６以下の飽和脂肪族炭化水素基が挙げられる。具体的には、メチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、ｓｅｃ−ブチル基、イソブチル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基などのアルキル基、さらに好ましくは、メチル基、エチル基、ｎ−プロピル基、ｎ−ブチル基、ｔｅｒｔ−ブチル基が例示される。また、これらのアルキル基は、置換基を有していてもよい。置換基としては、特に制限はなく、例えばアルキル基、アリール基、ヘテロアリール基などが挙げられる。
(R 1 ~R 6)
Examples of the alkyl group constituting R 1 to R 6 include saturated aliphatic hydrocarbon groups having 1 to 20 carbon atoms, more preferably 1 to 6 carbon atoms. Specifically, alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, and n-hexyl group. More preferably, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group are exemplified. Moreover, these alkyl groups may have a substituent. There is no restriction | limiting in particular as a substituent, For example, an alkyl group, an aryl group, heteroaryl group etc. are mentioned.
Ｒ１〜Ｒ６を構成するシクロアルキル基としては、炭素数が６〜４０の、より好ましくは６〜１８の飽和脂環式炭化水素基が挙げられる。具体的には、シクロプロピル、シクロヘキシル、ノルボルニル、アダマンチルなどのシクロアルキル基が例示される。これらのシクロアルキル基においても、上記アルキル基と同様に、アルキル基、アリール基、ヘテロアリール基などの置換基を有していてもよい。 Examples of the cycloalkyl group constituting R 1 to R 6 include saturated alicyclic hydrocarbon groups having 6 to 40 carbon atoms, more preferably 6 to 18 carbon atoms. Specific examples include cycloalkyl groups such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl. These cycloalkyl groups may have a substituent such as an alkyl group, an aryl group, or a heteroaryl group, similarly to the above alkyl group.
Ｒ１〜Ｒ６を構成するアリール基としては、炭素数が６〜４０の、より好ましくは６〜１８の芳香族炭化水素基が挙げられる。具体的には、フェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などのアリール基、さらに好ましくはフェニル基、ナフチル基、ビフェニル基が例示される。これらのアリール基においても、上記アルキル基と同様に、アルキル基、アリール基、ヘテロアリール基などの置換基を有していてもよい。 Examples of the aryl group constituting R 1 to R 6 include an aromatic hydrocarbon group having 6 to 40 carbon atoms, more preferably 6 to 18 carbon atoms. Specifically, aryl groups such as phenyl group, naphthyl group, biphenyl group, phenanthryl group, terphenyl group and pyrenyl group, more preferably phenyl group, naphthyl group and biphenyl group are exemplified. These aryl groups may have a substituent such as an alkyl group, an aryl group, or a heteroaryl group, similarly to the above alkyl group.
（Ａ）
Ａを構成するアリーレン基は、芳香族炭化水素基から導かれる２価の基であり、通常炭素数が６〜４０である。具体的には、フェニル基、ナフチル基、ビフェニル基、フェナントリル基、ターフェニル基、ピレニル基などの芳香族炭化水素基から導かれる２価の基が挙げられる。アリーレン基は、さらに置換基を有していてもよい。
(A)
The arylene group constituting A is a divalent group derived from an aromatic hydrocarbon group, and usually has 6 to 40 carbon atoms. Specific examples include divalent groups derived from an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a pyrenyl group. The arylene group may further have a substituent.
Ａを構成するヘテロアリーレン基は、炭素以外の原子を環内に有する芳香族基から導かれる２価の基であり、通常炭素数が２〜３０である。具体的には、フラニル基、チオフェニル基、オキサゾリル基、ピリジル基、キノリニル基などの炭素以外の原子を環内に有する芳香族基から導かれる２価の基が挙げられる。ヘテロアリーレン基は、さらに置換基を有していてもよい。 The heteroarylene group constituting A is a divalent group derived from an aromatic group having an atom other than carbon in the ring, and usually has 2 to 30 carbon atoms. Specific examples include a divalent group derived from an aromatic group having an atom other than carbon in the ring, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, or a quinolinyl group. The heteroarylene group may further have a substituent.
Ａｒ１〜Ａｒ３を構成するアリール基は、上記Ｒ１〜Ｒ６のアリール基と同様である。 The aryl group constituting Ar 1 to Ar 3 is the same as the aryl group for R 1 to R 6 described above.
また、Ａｒ２−Ｎ−Ａｒ３は、縮合して環を形成していてもよい。形成される環とは、Ａｒ２〜Ａｒ３の中から選ばれる任意のアリール基が互いに結合した共役または非共役の縮合環である。これら縮合環は、環内構造に窒素、酸素、硫黄原子を含んでいてもよい。 Ar 2 —N—Ar 3 may be condensed to form a ring. The formed ring is a conjugated or non-conjugated condensed ring in which arbitrary aryl groups selected from Ar 2 to Ar 3 are bonded to each other. These condensed rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure.
次に、本発明の一般式（１）で表される化合物の好ましい具体例を挙げる。本発明の一般式（１）で表される化合物は、これらに限定されるものではない。式中、Ｍｅは、メチル基を意味する。 Next, the preferable specific example of a compound represented by General formula (1) of this invention is given. The compound represented by General formula (1) of this invention is not limited to these. In the formula, Me means a methyl group.
本発明の発光素子において、正孔輸送層は、単独の一般式（１）で表される化合物のみで構成してもよく、一般式（１）で表される化合物を複数混合して構成してもよく、その他の正孔輸送材料の一種類以上を本発明の化合物と混合して構成してもよい。使用できるその他の正孔輸送材料としては、特に制限はなく、公知の正孔輸送材料が挙げられる。具体的には、４，４’−ビス[Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ]ビフェニル（ＴＰＤ）、４，４’−ビス[Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ]ビフェニル（α−ＮＰＤ）、４，４’，４”−トリス[３−メチルフェニル（フェニル）アミノ]トリフェニルアミン（ｍ−ＭＴＤＡＴＡ）などのトリフェニルアミン誘導体、ビス（Ｎ−アリールカルバゾール）またはビス（Ｎ−アルキルカルバゾール）などのビスカルバゾール誘導体、オリゴフェニレン誘導体などが例示できる。 In the light emitting device of the present invention, the hole transport layer may be composed of only the compound represented by the general formula (1), or may be composed of a mixture of a plurality of compounds represented by the general formula (1). Alternatively, one or more other hole transport materials may be mixed with the compound of the present invention. There is no restriction | limiting in particular as another hole transport material which can be used, A well-known hole transport material is mentioned. Specifically, 4,4′-bis [N- (3-methylphenyl) -N-phenylamino] biphenyl (TPD), 4,4′-bis [N- (1-naphthyl) -N-phenylamino ] Triphenylamine derivatives such as biphenyl (α-NPD), 4,4 ′, 4 ″ -tris [3-methylphenyl (phenyl) amino] triphenylamine (m-MTDATA), bis (N-arylcarbazole) or Examples thereof include biscarbazole derivatives such as bis (N-alkylcarbazole) and oligophenylene derivatives.
（製造方法）
本発明にかかる一般式（１）で表される化合物は、公知の方法で製造することができる。以下に、製造方法の例を示すが、これらの製造方法に限定されるものではない。
(Production method)
The compound represented by the general formula (1) according to the present invention can be produced by a known method. Although the example of a manufacturing method is shown below, it is not limited to these manufacturing methods.
（１） 例えば、塩化鉄（ＩＩＩ）を用いて、カルバゾールを二量化する。（２） 次に、二量化したビスカルバゾール骨格の窒素原子へアリール基を導入する。導入は、例えば、銅触媒存在の下、ビスカルバゾール誘導体とハロゲン化アリールとのカップリング反応を用いる方法などを用いて行う。（３） 次に、ビスカルバゾール骨格の炭素原子へアリール基もしくはアリールアミノ基を導入する。導入は、臭素、Ｎ−ブロモコハク酸イミドなどのハロゲン化剤を用いてビスカルバゾール誘導体をハロゲン化した後、パラジウム触媒と塩基存在下、アリールボロン酸もしくはアリールアミンとハロゲン化ビスカルバゾール誘導体を反応させる方法などを用いて行う。 (1) For example, carbazole is dimerized using iron (III) chloride. (2) Next, an aryl group is introduced into the nitrogen atom of the dimerized biscarbazole skeleton. The introduction is performed, for example, by a method using a coupling reaction between a biscarbazole derivative and an aryl halide in the presence of a copper catalyst. (3) Next, an aryl group or an arylamino group is introduced into the carbon atom of the biscarbazole skeleton. Introduction is a method of halogenating a biscarbazole derivative using a halogenating agent such as bromine or N-bromosuccinimide, and then reacting an aryl boronic acid or arylamine with the halogenated biscarbazole derivative in the presence of a palladium catalyst and a base. Etc.
（正孔輸送層の形成方法）
正孔輸送層は、抵抗加熱式または電子ビーム式の真空蒸着による方法、各種溶媒により溶解あるいは高分子結着剤を用いて混合物を調整した後に基板上に塗布する方法などを用いて形成すればよい。素子特性および量産安定性の観点から、真空蒸着による方法がより好ましい。
(Method for forming hole transport layer)
The hole transport layer may be formed by using a resistance heating type or electron beam type vacuum deposition method, a method using a solvent dissolved in various solvents or a mixture prepared using a polymer binder and then applying the mixture onto a substrate. Good. From the viewpoint of device characteristics and mass production stability, a method by vacuum deposition is more preferable.
［正孔注入層］
正孔輸送層と陽極との間に、正孔注入層を設けてもよい。正孔注入層を設けると、陽極から注入される正孔を効率よく正孔輸送層へ輸送することができる。発光素子の素子構成が正孔輸送層と陽極とが直接接する構成の場合に、一般式（１）で表される化合物と陽極の材料とのエネルギーギャップにより、正孔の輸送が阻害される場合がある。この場合に、発光層本来の発光が得られないからである。
[Hole injection layer]
A hole injection layer may be provided between the hole transport layer and the anode. When the hole injection layer is provided, holes injected from the anode can be efficiently transported to the hole transport layer. When the element structure of the light emitting element is a structure in which the hole transport layer and the anode are in direct contact, the hole gap is hindered by the energy gap between the compound represented by the general formula (1) and the anode material. There is. This is because in this case, the original light emission of the light emitting layer cannot be obtained.
正孔注入層に用いる材料としては、特に制限はなく、公知の正孔注入材料を用いることができる。例えば、４，４’，４”−トリス（Ｎ−３−メチルフェニル−Ｎ−フェニル−アミノ）トリフェニルアミン（ｍ−ＭＴＤＡＴＡ）などのトリフェニルアミン誘導体、銅フタロシアニンなどのフタロシアニン誘導体などが挙げられる。 There is no restriction | limiting in particular as a material used for a positive hole injection layer, A well-known hole injection material can be used. Examples include triphenylamine derivatives such as 4,4 ′, 4 ″ -tris (N-3-methylphenyl-N-phenyl-amino) triphenylamine (m-MTDATA), phthalocyanine derivatives such as copper phthalocyanine, and the like. .
また、正孔注入層は、電子受容性の材料をドーパントとして用いた、二種以上の化合物により形成されていてもよい。電子受容性の材料としては、特に制限はなく、公知の電子受容性の材料を用いることができる。例えば、塩化鉄(III)や塩化アルミニウムのようなルイス酸化合物、酸化モリブデンまたは酸化バナジウムのような金属酸化物、テトラフルオロテトラシアノキノンジメタン（Ｆ４−ＴＣＮＱ）のようなキノン誘導体、５−スルホサリチル酸のようなスルホン酸化合物、トリス（４−ブロモフェニル）アミニウムヘキサクロロアンチモネート（ＴＢＰＡＨ）のようなアンモニウム塩などが挙げられる。 The hole injection layer may be formed of two or more compounds using an electron-accepting material as a dopant. There is no restriction | limiting in particular as an electron-accepting material, A well-known electron-accepting material can be used. For example, Lewis acid compounds such as iron (III) chloride and aluminum chloride, metal oxides such as molybdenum oxide or vanadium oxide, quinone derivatives such as tetrafluorotetracyanoquinone dimethane (F4-TCNQ), 5-sulfo Examples thereof include sulfonic acid compounds such as salicylic acid and ammonium salts such as tris (4-bromophenyl) aminium hexachloroantimonate (TBPAH).
［発光層］
発光層では、正孔と電子との結合により、発光材料の励起子を生じさせ、励起子が基底状態に戻る際に発光する。
[Light emitting layer]
In the light-emitting layer, excitons of the light-emitting material are generated by the combination of holes and electrons, and light is emitted when the excitons return to the ground state.
本発明において発光層は、１層であっても２層以上であってもよい。複数層の場合に、それぞれの層が異なる発光色で発光してもよい。 In the present invention, the light emitting layer may be a single layer or two or more layers. In the case of a plurality of layers, each layer may emit light with different emission colors.
発光層に用いられる発光材料は、単一の材料であっても、複数の材料（ホスト材料、発光性ドーパント）であってもよい。ホスト材料と発光性ドーパント材料との混合物を用いるのが好ましい。ホスト材料と発光性ドーパント材料との混合物を用いると、膜形成が容易で、正孔・電子輸送能に優れ、発光の機能を分離できるので、発光効率、色純度、素子寿命の長期化の観点から好ましい。 The light emitting material used for the light emitting layer may be a single material or a plurality of materials (host material, light emitting dopant). It is preferable to use a mixture of a host material and a luminescent dopant material. Using a mixture of a host material and a light-emitting dopant material facilitates film formation, excels in hole / electron transport capability, and separates the function of light emission, so that light emission efficiency, color purity, and device lifetime can be extended. To preferred.
発光層が複数層の場合には、各発光層において、ホスト材料もしくは発光性ドーパント材料のいずれか一種類のみが発光してもよいし、ホスト材料と発光性ドーパント材料がともに発光してもよい。また、使用するホスト材料と発光性ドーパント材料とは、それぞれ一種類を用いても、複数種の組み合わせであっても、いずれでもよい。発光性ドーパント材料は、発光層の全体に含まれていても、部分的に含まれていても、いずれでもよい。 When there are a plurality of light emitting layers, in each light emitting layer, either one of the host material or the light emitting dopant material may emit light, or both the host material and the light emitting dopant material may emit light. . Further, the host material and the light-emitting dopant material to be used may be either one kind or a combination of plural kinds. The luminescent dopant material may be included in the entire light emitting layer, or may be partially included.
発光層のホスト材料としては、特に限定されず、例えば、アントラセンやなどの縮合アリール環を有する化合物やその誘導体、具体的には、４，４’−ビス（Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ）ビフェニルなどの芳香族アミン誘導体、トリス（８−キノリノラート）アルミニウム（III）をはじめとする金属キレート化オキシノイド化合物、ジスチリルベンゼン誘導体などのビススチリル誘導体、テトラフェニルブタジエン誘導体、インデン誘導体、クマリン誘導体、オキサジアゾール誘導体、ピロロピリジン誘導体、ピレン誘導体、アントラセン誘導体やテトラセン誘導体などのアセン化合物、ペリノン誘導体、シクロペンタジエン誘導体、オキサジアゾール誘導体、カルバゾール誘導体、ピロロピロール誘導体、ポリマー系では、ポリフェニレンビニレン誘導体、ポリパラフェニレン誘導体、ポリフルオレン誘導体、ポリビニルカルバゾール誘導体、ポリチオフェン誘導体などが挙げられる。 The host material of the light-emitting layer is not particularly limited, and examples thereof include compounds having a condensed aryl ring such as anthracene and derivatives thereof, specifically, 4,4′-bis (N- (1-naphthyl) -N -Aromatic amine derivatives such as phenylamino) biphenyl, metal chelated oxinoid compounds such as tris (8-quinolinolato) aluminum (III), bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarins Derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, pyrene derivatives, acene compounds such as anthracene derivatives and tetracene derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, carbazole derivatives, pyrrolopyrrole derivatives, in polymer systems Polyphenylene vinylene derivatives, polyparaphenylene derivatives, polyfluorene derivatives, polyvinylcarbazole derivatives, and polythiophene derivatives.
発光層の発光性ドーパント材料としては、特に限定されず、例えば、ナフタレン、アントラセン、フェナンスレン、ピレン、トリフェニレン、ペリレン、フルオレン、インデンなどの縮合アリール環を有する化合物やその誘導体、フラン、ピロール、チオフェン、シロール、９−シラフルオレン、９，９’−スピロビシラフルオレン、ベンゾチオフェン、ベンゾフラン、インドール、ジベンゾチオフェン、ジベンゾフラン、イミダゾピリジン、フェナントロリン、ピラジン、ナフチリジン、キノキサリン、ピロロピリジン、チオキサンテンなどのヘテロアリール環を有する化合物やその誘導体、ボラン誘導体、ジスチリルベンゼン誘導体、４，４’−ビス（２−（４−ジフェニルアミノフェニル）エテニル）ビフェニル、４，４’−ビス（Ｎ−（スチルベン−４−イル）−Ｎ−フェニルアミノ）スチルベンなどのアミノスチリル誘導体、芳香族アセチレン誘導体、テトラフェニルブタジエン誘導体、スチルベン誘導体、アルダジン誘導体、ピロメテン誘導体、ジケトピロロ［３，４−ｃ］ピロール誘導体、２，３，６，７−テトラヒドロ−１，１，７，７−テトラメチル−１Ｈ，５Ｈ，１１Ｈ−１０−（２−ベンゾチアゾリル）キノリジノ［９，９ａ，１−ｇｈ］クマリン（Ｃ５４５Ｔ）などのクマリン誘導体、Ｎ，Ｎ’−ジメチル−キナクリドンなどのキナクリドン誘導体、イミダゾール、チアゾール、チアジアゾール、カルバゾール、オキサゾール、オキサジアゾール、トリアゾールなどのアゾール誘導体およびその金属錯体およびＮ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジフェニル−１，１’−ジアミンに代表される芳香族アミン誘導体などが挙げられる。 The light emitting dopant material of the light emitting layer is not particularly limited, for example, a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene and derivatives thereof, furan, pyrrole, thiophene, Heteroaryl rings such as silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene And its derivatives, borane derivatives, distyrylbenzene derivatives, 4,4′-bis (2- (4-diphenylaminophenyl) ethenyl) biphenyl, 4,4′-bis (N Aminostyryl derivatives such as (stilbene-4-yl) -N-phenylamino) stilbene, aromatic acetylene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, pyromethene derivatives, diketopyrrolo [3,4-c] pyrrole derivatives, 2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H, 11H-10- (2-benzothiazolyl) quinolidino [9,9a, 1-gh] coumarin (C545T), etc. Coumarin derivatives, quinacridone derivatives such as N, N′-dimethyl-quinacridone, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole and metal complexes thereof, and N, N′-diphenyl-N, N '-Di (3- Butylphenyl) -4,4'-like aromatic amines derivatives typified by diphenyl-1,1'-diamine.
発光性ドーパント材料の量は、多すぎると濃度消光現象が起きる。このため、ホスト材料に対して２０重量％以下で用いることが好ましく、さらに好ましくは１０重量％以下である。ドーピング方法としては、ホスト材料との共蒸着法、ホスト材料と混合してから蒸着する方法、またはホスト材料と発光性ドーパント材料を望む割合で溶媒に溶かし塗布する方法が挙げられる。 If the amount of the luminescent dopant material is too large, a concentration quenching phenomenon occurs. For this reason, it is preferable to use it at 20 weight% or less with respect to a host material, More preferably, it is 10 weight% or less. Examples of the doping method include a co-evaporation method with a host material, a method of vapor deposition after mixing with the host material, or a method of dissolving the host material and the light-emitting dopant material in a desired ratio and applying them.
発光層は、抵抗加熱式または電子ビーム式の真空蒸着による方法、発光材料を各種溶媒により溶解あるいは高分子結着剤を用いて混合物を調整した後に基板上に塗布する方法により形成される。素子特性の観点から真空蒸着による方法がより好ましい。 The light emitting layer is formed by a resistance heating type or electron beam type vacuum deposition method, or a method in which a light emitting material is dissolved in various solvents or a mixture is prepared using a polymer binder and then applied onto a substrate. From the viewpoint of device characteristics, a method by vacuum deposition is more preferable.
[電子輸送層]
電子輸送層は、陰極から電子が注入され、注入された電子を輸送する層である。電子輸送層は、電子輸送層には、電子注入効率が高く、注入された電子を効率良く輸送することが要求される。このため、電子輸送層を構成する電子輸送材料としては、電子親和力が大きく、しかも電子移動度が大きく、さらに安定性に優れ、トラップとなる不純物が製造時および使用時に発生しにくい物質であると好ましい。一方、正孔と電子の輸送バランスを考えた場合に、電子輸送層が陽極からの正孔が再結合せずに陰極側へ流れるのを効率よく阻止できる役割を主に果たすならば、電子輸送能力がそれ程高くない材料で構成されていてもよい。すなわち、電子輸送能力がそれ程高くない材料であっても、発光効率を向上させる効果は電子輸送能力が高い材料で構成されている場合と同等となる。したがって、本発明における電子輸送層には、正孔の移動を効率よく阻止できる正孔阻止材料で形成された層も同義のものとして含まれる。
[Electron transport layer]
The electron transport layer is a layer in which electrons are injected from the cathode and transports the injected electrons. The electron transport layer is required to have high electron injection efficiency and efficiently transport injected electrons. For this reason, the electron transport material constituting the electron transport layer is a substance having a large electron affinity, a large electron mobility, excellent stability, and a trapping impurity that is unlikely to be generated during manufacture and use. preferable. On the other hand, when considering the transport balance of holes and electrons, if the electron transport layer mainly plays a role of effectively preventing the holes from the anode from recombining and flowing to the cathode side, the electron transport You may be comprised with the material whose capability is not so high. In other words, even if the material has an electron transport capability that is not so high, the effect of improving the light emission efficiency is equivalent to that of a material that has a high electron transport capability. Accordingly, the electron transport layer in the present invention includes a layer formed of a hole blocking material capable of efficiently blocking the movement of holes as synonymous.
電子輸送層に用いられる電子輸送材料は、特に限定されず、ナフタレン、アントラセンなどの縮合多環芳香族誘導体、４，４’−ビス（ジフェニルエテニル）ビフェニルに代表されるスチリル系芳香環誘導体、アントラキノンやジフェノキノンなどのキノン誘導体、リンオキサイド誘導体、トリス（８−キノリノラート）アルミニウム（III）などのキノリノール錯体、ベンゾキノリノール錯体、ヒドロキシアゾール錯体、アゾメチン錯体、トロポロン金属錯体およびフラボノール金属錯体などの各種金属錯体が挙げられる。特に、駆動電圧を低減し、高効率発光が得られることから、不対電子を有する電子受容性窒素を含む含窒素芳香環構造を有する化合物を用いることが好ましい。 The electron transport material used for the electron transport layer is not particularly limited, and condensed polycyclic aromatic derivatives such as naphthalene and anthracene, styryl-based aromatic ring derivatives represented by 4,4′-bis (diphenylethenyl) biphenyl, Various metal complexes such as quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, quinolinol complexes such as tris (8-quinolinolato) aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes and flavonol metal complexes Is mentioned. In particular, a compound having a nitrogen-containing aromatic ring structure containing an electron-accepting nitrogen having an unpaired electron is preferably used because the driving voltage is reduced and high-efficiency light emission can be obtained.
ここで、電子受容性窒素とは、隣接原子との間に多重結合を形成している窒素原子を表す。窒素原子が高い電子陰性度を有することから、該多重結合は電子受容的な性質を有する。それゆえ、電子受容性窒素を含むヘテロアリール環は、高い電子親和性を有し、電子輸送能に優れ、電子輸送層に用いることで発光素子の駆動電圧を低減できる。電子受容性窒素を含むヘテロアリール環としては、例えば、ピリジン環、ピラジン環、ピリミジン環、キノリン環、キノキサリン環、ナフチリジン環、ピリミドピリミジン環、ベンゾキノリン環、フェナントロリン環、イミダゾール環、オキサゾール環、オキサジアゾール環、トリアゾール環、チアゾール環、チアジアゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、ベンズイミダゾール環、フェナンスロイミダゾール環などが挙げられる。 Here, the electron-accepting nitrogen represents a nitrogen atom that forms a multiple bond with an adjacent atom. Since the nitrogen atom has a high electronegativity, the multiple bond has an electron accepting property. Therefore, a heteroaryl ring containing electron-accepting nitrogen has high electron affinity, excellent electron transport ability, and can be used for an electron transport layer to reduce the driving voltage of a light-emitting element. Examples of the heteroaryl ring containing an electron-accepting nitrogen include, for example, a pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring, Examples thereof include an oxadiazole ring, a triazole ring, a thiazole ring, a thiadiazole ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, and a phenanthrimidazole ring.
ヘテロアリール環構造を有する化合物としては、例えば、ベンズイミダゾール誘導体、ベンズオキサゾール誘導体、ベンズチアゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体、ピラジン誘導体、フェナントロリン誘導体、キノキサリン誘導体、キノリン誘導体、ベンゾキノリン誘導体、ビピリジンやターピリジンなどのオリゴピリジン誘導体、キノキサリン誘導体およびナフチリジン誘導体などが好ましい化合物として挙げられる。中でも、トリス（Ｎ−フェニルベンズイミダゾール−２−イル）ベンゼンなどのイミダゾール誘導体、１，３−ビス［（４−ｔｅｒｔ−ブチルフェニル）−１，３，４−オキサジアゾリル］フェニレンなどのオキサジアゾール誘導体、Ｎ−ナフチル−２，５−ジフェニル−１，３，４−トリアゾールなどのトリアゾール誘導体、バソクプロインや１，３−ビス（１，１０−フェナントロリン−９−イル）ベンゼンなどのフェナントロリン誘導体、２，２’−ビス（ベンゾ［ｈ］キノリン−２−イル）−９，９’−スピロビフルオレンなどのベンゾキノリン誘導体、２，５−ビス[６’−（２’，２”−ビピリジル）]−１，１−ジメチル−３，４−ジフェニルシロールなどのビピリジン誘導体、１，３−ビス[４’−（２，２’：６’２”−ターピリジニル）]ベンゼンなどのターピリジン誘導体、ビス（１−ナフチル）−４−（１，８−ナフチリジン−２−イル）フェニルホスフィンオキサイドなどのナフチリジン誘導体が、電子輸送能の点から好ましく用いられる。 Examples of the compound having a heteroaryl ring structure include benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazine derivatives, phenanthroline derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives. Preferred examples include oligopyridine derivatives such as bipyridine and terpyridine, quinoxaline derivatives, and naphthyridine derivatives. Among them, imidazole derivatives such as tris (N-phenylbenzimidazol-2-yl) benzene and oxadiazole derivatives such as 1,3-bis [(4-tert-butylphenyl) -1,3,4-oxadiazolyl] phenylene Triazole derivatives such as N-naphthyl-2,5-diphenyl-1,3,4-triazole, phenanthroline derivatives such as bathocuproin and 1,3-bis (1,10-phenanthroline-9-yl) benzene, 2,2 Benzoquinoline derivatives such as' -bis (benzo [h] quinolin-2-yl) -9,9'-spirobifluorene, 2,5-bis [6 '-(2', 2 "-bipyridyl)]-1 Bipyridine derivatives such as 1,1-dimethyl-3,4-diphenylsilole, 1,3-bis [4 ′-(2,2 ′: 6′2 ″ -ter Lysinyl)] terpyridine derivatives such as benzene, naphthyridine derivatives such as bis (1-naphthyl) -4- (1,8-naphthyridin-2-yl) phenylphosphine oxide are preferably used from the viewpoint of electron transporting capability.
上記電子輸送材料は、単独でも用いてもよく、２種以上の電子輸送材料を混合して用いてもよく、その他の電子輸送材料の一種以上を上記の電子輸送材料に混合して用いてもよい。また、アルカリ金属やアルカリ土類金属などの金属と混合して用いることも可能である。 The electron transport material may be used alone, or two or more kinds of electron transport materials may be mixed and used, or one or more of other electron transport materials may be mixed and used in the electron transport material. Good. It is also possible to use a mixture with a metal such as an alkali metal or an alkaline earth metal.
電子輸送層のイオン化ポテンシャルは、特に限定されないが、好ましくは５．８ｅＶ以上８．０ｅＶ以下であり、より好ましくは６．０ｅＶ以上７．５ｅＶ以下である。 The ionization potential of the electron transport layer is not particularly limited, but is preferably 5.8 eV or more and 8.0 eV or less, and more preferably 6.0 eV or more and 7.5 eV or less.
電子輸送層は、抵抗加熱式または電子ビーム式の真空蒸着による方法、電子輸送材料を各種溶媒により溶解あるいは高分子結着剤を用いて混合物を調整した後に基板上に塗布する方法が用いて形成することができる。素子特性の観点から真空蒸着による方法がより好ましい。 The electron transport layer is formed by a resistance heating type or electron beam type vacuum deposition method, a method in which an electron transport material is dissolved in various solvents or a mixture is prepared using a polymer binder and then applied onto a substrate. can do. From the viewpoint of device characteristics, a method by vacuum deposition is more preferable.
本発明の発光素子において、各層の厚みは、発光物質の抵抗値にもよるので限定することはできないが、通常１〜１０００ｎｍの間から選ばれる。発光層、電子輸送層、正孔輸送層などの有機層の膜厚はそれぞれ、好ましくは１ｎｍ以上２００ｎｍ以下であり、さらに好ましくは５ｎｍ以上１００ｎｍ以下である。 In the light-emitting device of the present invention, the thickness of each layer depends on the resistance value of the light-emitting substance and cannot be limited, but is usually selected from 1 to 1000 nm. The thicknesses of the organic layers such as the light emitting layer, the electron transport layer, and the hole transport layer are each preferably 1 nm to 200 nm, and more preferably 5 nm to 100 nm.
その他、電子注入層、正孔ブロック層、保護膜、封止膜など、発光素子に設けられる公知の層や膜を設けてもよい。 In addition, a known layer or film provided in the light-emitting element such as an electron injection layer, a hole blocking layer, a protective film, or a sealing film may be provided.
本発明の発光素子は、電気エネルギーを光に変換する。ここで電気エネルギーとしては主に直流電流が使用されるが、パルス電流や交流電流を用いることも可能である。電流値および電圧値は特に制限はないが、素子の消費電力や寿命を考慮すると、できるだけ低いエネルギーで最大の輝度が得られるよう選べばよい。 The light emitting device of the present invention converts electrical energy into light. Here, a direct current is mainly used as the electric energy, but a pulse current or an alternating current can also be used. The current value and the voltage value are not particularly limited, but may be selected so that the maximum luminance can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the element.
本発明の発光素子は、例えばマトリクスおよび／またはセグメント方式で表示するディスプレイとして好適に用いられる。 The light emitting device of the present invention is suitably used as a display for displaying in a matrix and / or segment system, for example.
マトリクス方式とは、表示のための画素が格子状やモザイク状など二次元的に配置され、画素の集合で文字や画像を表示する。画素の形状やサイズは用途によって決まる。例えば、パソコン、モニター、テレビの画像および文字表示には、通常一辺が３００μｍ以下の四角形の画素が用いられ、また、表示パネルのような大型ディスプレイの場合は、一辺がｍｍオーダーの画素を用いることになる。モノクロ表示の場合は、同じ色の画素を配列すればよいが、カラー表示の場合には、赤、緑、青の画素を並べて表示させる。この場合、典型的にはデルタタイプとストライプタイプがある。そして、このマトリクスの駆動方法は、線順次駆動方法やアクティブマトリクスのどちらでもよい。線順次駆動はその構造が簡単であるが、動作特性を考慮した場合、アクティブマトリクスの方が優れる場合があるので、これも用途によって使い分けることが必要である。 In the matrix method, pixels for display are two-dimensionally arranged such as a lattice shape or a mosaic shape, and a character or an image is displayed by a set of pixels. The shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 μm or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become. In monochrome display, pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type. The matrix driving method may be either a line sequential driving method or an active matrix. Although the structure of the line sequential drive is simple, the active matrix may be superior in consideration of the operation characteristics, and it is necessary to use it depending on the application.
本発明におけるセグメント方式とは、予め決められた情報を表示するようにパターンを形成し、このパターンの配置によって決められた領域を発光させる方式である。例えば、デジタル時計や温度計における時刻や温度表示、オーディオ機器や電磁調理器などの動作状態表示および自動車のパネル表示などが挙げられる。そして、前記マトリクス表示とセグメント表示は同じパネルの中に共存していてもよい。 The segment system in the present invention is a system in which a pattern is formed so as to display predetermined information and an area determined by the arrangement of the pattern is caused to emit light. For example, the time and temperature display in a digital clock or a thermometer, the operation state display of an audio device or an electromagnetic cooker, the panel display of an automobile, and the like can be mentioned. The matrix display and the segment display may coexist in the same panel.
本発明の発光素子は、各種機器等のバックライトとしても好ましく用いられる。バックライトは、主に自発光しない表示装置の視認性を向上させる目的に使用され、液晶表示装置、時計、オーディオ装置、自動車パネル、表示板および標識などに使用される。特に、液晶表示装置、中でも薄型化が検討されているパソコン用途のバックライトに本発明の発光素子は好ましく用いられ、従来のものより薄型で軽量なバックライトを提供できる。 The light emitting device of the present invention is also preferably used as a backlight for various devices. The backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, the light-emitting element of the present invention is preferably used for a backlight for a liquid crystal display device, particularly a personal computer for which a reduction in thickness is being considered, and a backlight that is thinner and lighter than conventional ones can be provided.
以下本発明を詳細に説明するため実施例を挙げるが、本発明は実施例に限定されるものではない。なお、実施例にある化合物の番号は、上記の化学式に記載した番号を意味する。 EXAMPLES Examples will be given below to describe the present invention in detail, but the present invention is not limited to the examples. In addition, the number of the compound in an Example means the number described in said chemical formula.
（実施例１） 化合物［２３］の合成
アルゴン雰囲気下、塩化鉄（ＩＩＩ）３８．９ｇとクロロホルム２４０ｍＬを加えた２Ｌの三口フラスコに、カルバゾール２０．０ｇのクロロホルム４００ｍＬ懸濁液を室温にて撹拌しながら加え、一晩撹拌した。塩化鉄（ＩＩＩ）１２．２ｇのクロロホルム５０ｍＬ溶液を加え、さらに５時間撹拌した。この反応液を氷冷したのち、１Ｍ塩酸３２５ｍＬと酢酸エチル４００ｍＬを加え、３０分間撹拌した。析出した沈殿物を吸引濾過により濾取し、水、酢酸エチルで順次洗浄した。得られた固体をＮ，Ｎ’−ジメチルイミダゾリジノン（以下、「ＤＭＩ」という）１３０ｍＬに加え、１２０℃に加熱して溶解したのち、室温に冷却した。析出した沈殿物を吸引濾過により濾取し、ＤＭＩ、メタノールで順次洗浄したのち、７０℃にて２時間真空乾燥した。ついで、得られた固体を１，４−ジオキサン４００ｍＬに加え、１３０℃に加熱して溶解し、熱時濾過した。濾液を室温に冷却したのち、エバポレーターで減圧濃縮した。濃縮残渣を１，４−ジオキサン２０ｍＬに加え、１３０℃にて１時間撹拌したのち、放冷した。沈殿物を吸引濾過により濾取し、１，４−ジオキサン、メタノールで順次洗浄したのち、７０℃にて真空乾燥し、３，３’−ビスカルバゾール１１．３ｇを得た。
(Example 1) Synthesis of Compound [23] Under a argon atmosphere, a suspension of carbazole (20.0 g) in chloroform (400 mL) was stirred at room temperature in a 2 L three-necked flask containing 38.9 g of iron (III) chloride and 240 mL of chloroform. And stirred overnight. A solution of iron chloride (III) 12.2 g in chloroform 50 mL was added, and the mixture was further stirred for 5 hours. The reaction mixture was ice-cooled, 325 mL of 1M hydrochloric acid and 400 mL of ethyl acetate were added, and the mixture was stirred for 30 minutes. The deposited precipitate was collected by suction filtration and washed successively with water and ethyl acetate. The obtained solid was added to 130 mL of N, N′-dimethylimidazolidinone (hereinafter referred to as “DMI”), dissolved by heating to 120 ° C., and then cooled to room temperature. The deposited precipitate was collected by suction filtration, washed successively with DMI and methanol, and then vacuum-dried at 70 ° C. for 2 hours. Subsequently, the obtained solid was added to 400 mL of 1,4-dioxane, dissolved by heating to 130 ° C., and filtered while hot. The filtrate was cooled to room temperature and then concentrated under reduced pressure using an evaporator. The concentrated residue was added to 20 mL of 1,4-dioxane, stirred at 130 ° C. for 1 hour, and then allowed to cool. The precipitate was collected by suction filtration, washed successively with 1,4-dioxane and methanol, and then vacuum dried at 70 ° C. to obtain 11.3 g of 3,3′-biscarbazole.
次に、３，３’−ビスカルバゾール１０．０ｇ、４−ブロモトルエン１０．８ｇ、ビス（ジベンジリデンアセトン）パラジウム（０）［以下、「Ｐｄ（ｄｂａ）２」という］１．８１ｇ、トリ−ｔｅｒｔ−ブチルホスフィンテトラフルオロホウ酸錯体８２２ｍｇ、ｔｅｒｔ−ブトキシナトリウム６．０７ｇとキシレン３００ｍＬの混合溶液をアルゴン雰囲気下、１３０℃で２２時間撹拌した。室温にまで冷却したのち、トルエン３００ｍＬを加えて濾過し、濾液をエバポレーターで濃縮した。濃縮残渣をトルエン５０ｍＬに加え、１１０℃に加熱して溶解し、放冷した。析出した固体を濾過し、トルエン、ヘキサンで順次洗浄したのち、７０℃にて真空乾燥し、９−ｐ−トリル−９Ｈ−カルバゾール二量体１０．０ｇを得た。 Next, 10.0 g of 3,3′-biscarbazole, 10.8 g of 4-bromotoluene, bis (dibenzylideneacetone) palladium (0) [hereinafter referred to as “Pd (dba) 2 ”] 1.81 g, tri- A mixed solution of 822 mg of tert-butylphosphine tetrafluoroborate complex, 6.07 g of tert-butoxy sodium and 300 mL of xylene was stirred at 130 ° C. for 22 hours under an argon atmosphere. After cooling to room temperature, 300 mL of toluene was added and filtered, and the filtrate was concentrated with an evaporator. The concentrated residue was added to 50 mL of toluene, dissolved by heating to 110 ° C., and allowed to cool. The precipitated solid was filtered, washed sequentially with toluene and hexane, and then vacuum dried at 70 ° C. to obtain 10.0 g of 9-p-tolyl-9H-carbazole dimer.
アルゴン雰囲気下、９−ｐ−トリル−９Ｈ−カルバゾール二量体９．８０ｇのジクロロメタン３００ｍＬ溶液に、Ｎ−ブロモコハク酸イミド７．１５ｇのジクロロメタン２００ｍＬ懸濁液を加え、室温にて５時間撹拌した。析出した固体を濾過により除去し、濾液をエバポレーターにて濃縮した。濃縮残渣をトルエン４００ｍＬに加え、１１５℃に加熱して１時間撹拌したのち、放冷した。白色の沈殿物を濾過し、トルエン、ヘキサンで順次洗浄したのち、７０℃にて真空乾燥し、３−ブロモ−９−ｐ−トリル−９Ｈ−カルバゾール二量体１７．０ｇを得た。 Under an argon atmosphere, a suspension of 9.80 g of 9-p-tolyl-9H-carbazole dimer in 300 mL of dichloromethane was added a suspension of N-bromosuccinimide 7.15 g in dichloromethane 200 mL, and the mixture was stirred at room temperature for 5 hours. The precipitated solid was removed by filtration, and the filtrate was concentrated with an evaporator. The concentrated residue was added to 400 mL of toluene, heated to 115 ° C. and stirred for 1 hour, and then allowed to cool. The white precipitate was filtered, washed successively with toluene and hexane, and then vacuum dried at 70 ° C. to obtain 17.0 g of 3-bromo-9-p-tolyl-9H-carbazole dimer.
３−ブロモ−９−ｐ−トリル−９Ｈ−カルバゾール二量体２．４０ｇ、４−（ジフェニルアミノ）フェニルボロン酸２．１２ｇ、Ｐｄ（ｄｂａ）２２０６ｍｇ、トリ−ｔｅｒｔ−ブチルホスフィンテトラフルオロホウ酸錯体９３．５ｍｇ、ｔｅｒｔ−ブトキシナトリウム７０５ｍｇとキシレン７０ｍＬの混合溶液をアルゴン雰囲気下、１３０℃で１８時間撹拌した。室温にまで冷却したのち、トルエン７０ｍＬを加えて濾過し、濾液をエバポレーターで濃縮した。濃縮残渣をカラムクロマト（Ｗａｋｏｇｅｌ Ｃ−２００、ヘキサン／トルエン）にて分離したのち、熱トルエン２０ｍＬにて４回洗浄し、７０℃にて真空乾燥し、化合物［２３］０．６４ｇを得た。この化合物を、油拡散ポンプを用いて１×１０−３Ｐａの圧力下、２８０度で昇華精製を行ってから正孔輸送材料として使用した。 3-Bromo-9-p-tolyl-9H-carbazole dimer 2.40 g, 2.12 g of 4- (diphenylamino) phenylboronic acid, 206 mg of Pd (dba) 2 , tri-tert-butylphosphine tetrafluoroborate A mixed solution of 93.5 mg of the complex, 705 mg of tert-butoxy sodium and 70 mL of xylene was stirred at 130 ° C. for 18 hours under an argon atmosphere. After cooling to room temperature, 70 mL of toluene was added and filtered, and the filtrate was concentrated with an evaporator. The concentrated residue was separated by column chromatography (Wakogel C-200, hexane / toluene), washed 4 times with 20 mL of hot toluene, and vacuum dried at 70 ° C. to obtain 0.64 g of compound [23]. This compound was used as a hole transport material after sublimation purification at 280 degrees under a pressure of 1 × 10 −3 Pa using an oil diffusion pump.
（実施例２）
正孔輸送層に化合物［２３］を使った発光素子を次のように作製した。３８ｍｍ×４６ｍｍの無アルカリガラス基板（コーニング（株）製、＃１７３７）上にＩＴＯ導電膜（スパッタ品）を、ガラス基板中央部分に３８ｍｍ×１３ｍｍ、膜厚１５０ｎｍ（１１Ω／□）に形成し陽極とした。陽極が形成された基板をアセトン、“セミコクリン５６”（商品名、フルウチ化学（株）製）で１５分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールで１５分間超音波洗浄してから熱メタノールに１５分間浸漬させて乾燥させた。素子を作製する直前にこの基板を１時間ＵＶ−オゾン処理し、さらに真空蒸着装置内に設置して、装置内の真空度が５×１０−４Ｐａ以下になるまで排気した。抵抗加熱法によって、まず正孔注入層として銅フタロシアニン（以下、「ＣｕＰｃ」という）を１０ｎｍの厚さに成膜した。次に正孔輸送層として化合物［２３］を５０ｎｍ積層した。その上に発光層を以下の通りに形成した。ホスト材料としてトリス（８−キノリノラート）アルミニウム（ＩＩＩ）（Ａｌｑ３）を、発光性ドーパントとしてＮ，Ｎ’−ジメチル−キナクリドンをドープ濃度が２重量％になるように４０ｎｍの厚さに積層した。次に電子輸送層として下記に示す（Ｅ−１）を３５ｎｍの厚さに積層した。以上のようにして形成した有機層上に、フッ化リチウムを０．５ｎｍ蒸着した後、アルミニウム１００ｎｍを蒸着して陰極とし、５×５ｍｍ角の発光素子を作製した。ここで示した膜厚は水晶発振式膜厚モニター表示値である。この発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率４．２ｌｍ／Ｗの緑色発光が得られた。またこの発光素子を１０ｍＡ／ｃｍ２で直流駆動した時の輝度半減時間は９０００時間であった。
(Example 2)
A light emitting device using the compound [23] for the hole transport layer was produced as follows. An ITO conductive film (sputtered product) is formed on a 38 mm × 46 mm non-alkali glass substrate (# 1737 manufactured by Corning Co., Ltd.), and the anode is formed by forming 38 mm × 13 mm and a film thickness of 150 nm (11Ω / □) in the central portion of the glass substrate. It was. The substrate on which the anode was formed was ultrasonically cleaned with acetone, “Semicocrine 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. Subsequently, it was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes and dried. Immediately before the device was fabricated, this substrate was subjected to UV-ozone treatment for 1 hour, further placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 × 10 −4 Pa or less. First, copper phthalocyanine (hereinafter referred to as “CuPc”) was formed to a thickness of 10 nm as a hole injection layer by a resistance heating method. Next, 50 nm of compound [23] was laminated | stacked as a positive hole transport layer. A light emitting layer was formed thereon as follows. Tris (8-quinolinolato) aluminum (III) (Alq3) as a host material and N, N′-dimethyl-quinacridone as a light-emitting dopant were laminated to a thickness of 40 nm so that the doping concentration was 2% by weight. Next, (E-1) shown below as an electron transport layer was laminated to a thickness of 35 nm. On the organic layer formed as described above, 0.5 nm of lithium fluoride was vapor-deposited, and then 100 nm of aluminum was vapor-deposited as a cathode to produce a 5 × 5 mm square light emitting device. The film thickness shown here is a display value of the crystal oscillation type film thickness monitor. When this light emitting device was DC-driven at 10 mA / cm 2 , green light emission with a luminous efficiency of 4.2 lm / W was obtained. The luminance half time when this light emitting device was DC-driven at 10 mA / cm 2 was 9000 hours.
（比較例１）
正孔輸送層としてα−ＮＰＤを用いた以外は実施例２と同様にして発光素子を作製した。得られた発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率３．０ｌｍ／Ｗの緑色発光が得られた。またこの発光素子を１０ｍＡ／ｃｍ２で直流駆動した時の輝度半減時間は４０００時間であった。
(Comparative Example 1)
A light emitting device was produced in the same manner as in Example 2 except that α-NPD was used as the hole transport layer. When the obtained light emitting device was DC-driven at 10 mA / cm 2 , green light emission with a luminous efficiency of 3.0 lm / W was obtained. The luminance half time when this light emitting device was DC-driven at 10 mA / cm 2 was 4000 hours.
以上より、正孔輸送材料が本発明の化合物である実施例２の発光素子の発光効率、輝度半減時間は、比較例１の発光素子の発光効率、輝度半減時間より優れていることがわかる。 From the above, it can be seen that the light emission efficiency and luminance half-life of the light-emitting device of Example 2 in which the hole transport material is the compound of the present invention are superior to the light emission efficiency and luminance half-life of the light-emitting device of Comparative Example 1.
（比較例２）
正孔輸送層として下記の化合物（Ｈ−１）を用いた以外は実施例２と同様にして発光素子を作製した。得られた発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率３．５ｌｍ／Ｗの緑色発光が得られた。またこの発光素子を１０ｍＡ／ｃｍ２で直流駆動した時の輝度半減時間は３０００時間であった。
(Comparative Example 2)
A light emitting device was produced in the same manner as in Example 2 except that the following compound (H-1) was used as the hole transport layer. When the obtained light emitting device was DC-driven at 10 mA / cm 2 , green light emission with a luminous efficiency of 3.5 lm / W was obtained. The luminance half time when this light emitting device was DC-driven at 10 mA / cm 2 was 3000 hours.
以上より、正孔輸送材料が本発明の化合物である実施例２の発光素子の発光効率、輝度半減時間は、比較例２の発光素子の発光効率、輝度半減時間より優れていることがわかる。 From the above, it can be seen that the luminous efficiency and luminance half-life of the light-emitting device of Example 2 in which the hole transport material is the compound of the present invention are superior to the luminous efficiency and luminance half-life of the light-emitting device of Comparative Example 2.
（実施例３）
電子輸送層として下記の化合物（Ｅ−２）を用いた以外は実施例２と同様にして発光素子を作製した。得られた発光素子を１０ｍＡ／ｃｍ２で直流駆動したところ、発光効率４．０ｌｍ／Ｗの緑色発光が得られた。またこの発光素子を１０ｍＡ／ｃｍ２で直流駆動した時の輝度半減時間は８０００時間であった。本実施例の発光素子においても発光効率、輝度半減時間が優れていることがわかる。
(Example 3)
A light emitting device was produced in the same manner as in Example 2 except that the following compound (E-2) was used as the electron transport layer. When the obtained light-emitting element was DC-driven at 10 mA / cm 2 , green light emission with a luminous efficiency of 4.0 lm / W was obtained. The luminance half time when this light emitting device was DC-driven at 10 mA / cm 2 was 8000 hours. It can be seen that the light emitting element of this example is also excellent in luminous efficiency and luminance half time.
（実施例４〜５）
電子輸送層として下記の化合物（Ｅ−３）〜（Ｅ−４）を用いた以外は実施例２と同様にして発光素子を作製、評価した。各実施例の結果は表１に示した。
A light emitting device was prepared and evaluated in the same manner as in Example 2 except that the following compounds (E-3) to (E-4) were used as the electron transport layer. The results of each example are shown in Table 1.
表１から、本発明にかかる正孔輸送材料を用いた発光素子では、従来からの電子輸送層を用いても、電力効率（実施例４：３．８、実施例５：４．０）、輝度半減時間（実施例４：８０００、実施例５：７４００）ともに、比較例１、２の発光素子の電力効率（比較例１：３．０、比較例２：３．５）、輝度半減時間（比較例１：４０００、比較例２：３０００）に比べ、優れていることがわかる。
From Table 1, in the light emitting device using the hole transport material according to the present invention, even when a conventional electron transport layer is used, the power efficiency (Example 4: 3.8, Example 5: 4.0), Both the luminance half-life (Example 4: 8000, Example 5: 7400), the power efficiency (Comparative Example 1: 3.0, Comparative Example 2: 3.5) of the light-emitting elements of Comparative Examples 1 and 2, and the luminance half-time It can be seen that it is superior to (Comparative Example 1: 4000, Comparative Example 2: 3000).
Claims (2)
前記正孔輸送層は、下記一般式（１）で表される化合物を含有する、発光素子。
The said positive hole transport layer is a light emitting element containing the compound represented by following General formula (1).
前記電子輸送層は、不対電子対を有する含窒素芳香族化合物を含有する、請求項1に記載の発光素子。 Between the cathode and the light emitting layer, at least an electron transport layer,
2. The light emitting device according to claim 1, wherein the electron transport layer contains a nitrogen-containing aromatic compound having an unpaired electron pair.
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| US8828561B2 (en) | 2009-11-03 | 2014-09-09 | Cheil Industries, Inc. | Compound for organic photoelectric device and organic photoelectric device including the same |
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| CN103262287A (en) | 2010-12-28 | 2013-08-21 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element using same |
| US8803134B2 (en) | 2011-02-07 | 2014-08-12 | Idemitsu Kosan Co., Ltd. | Biscarbazole derivatives and organic electroluminescence |
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