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JP3547769B2 - Electroluminescent device - Google Patents
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JP3547769B2 - Electroluminescent device - Google Patents

Electroluminescent device Download PDF

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Publication number
JP3547769B2
JP3547769B2 JP29135892A JP29135892A JP3547769B2 JP 3547769 B2 JP3547769 B2 JP 3547769B2 JP 29135892 A JP29135892 A JP 29135892A JP 29135892 A JP29135892 A JP 29135892A JP 3547769 B2 JP3547769 B2 JP 3547769B2
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Japan
Prior art keywords
organic
transport layer
injection electrode
electroluminescent device
oxadiazole
Prior art date
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Expired - Fee Related
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JP29135892A
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Japanese (ja)
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JPH06140156A (en
Inventor
佳高 西尾
健志 佐野
政行 藤田
孝則 藤井
祐次 浜田
賢一 柴田
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Sanyo Electric Co Ltd
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Sanyo Electric Co Ltd
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Priority to US08/142,970 priority patent/US5449564A/en
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  • Luminescent Compositions (AREA)
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Description

【0001】
【産業上の利用分野】
本発明は、電界発光素子に関し、特に、有機電子輸送層に新規な有機材料を用いた有機電界発光素子に関する。
【0002】
【従来の技術】
近年、情報機器の多様化に伴って、CRTより低消費電力で空間占有容積が少ない平面表示素子のニーズが高まっている。このような平面表示素子としては、液晶、プラズマディスプレイ等があるが、特に最近は、自己発光型で表示が鮮明な電界発光素子が注目されている。
【0003】
ここで、電界発光素子は構成する材料により、無機電界発光素子と有機電界発光素子とに大別することができ、無機電界発光素子は既に実用化されている。
しかしながら、無機電界発光素子の駆動方式は、高電界の印加によって加速された電子が、発光中心を衝突励起して発光させるという所謂衝突励起型発光であるため、高電圧で駆動する必要がある。このため、周辺機器の高コスト化を招来するという課題を有していた。
【0004】
これに対し、有機電界発光素子は、電極から注入された電荷が発光体中で再結合して発光するという、所謂、注入型発光であるため、低電圧で駆動することができる。しかも、有機化合物の分子構造を変更することによって任意の発光色を容易に得ることができるといった利点もある。したがって、有機電界発光素子は、これからの表示素子として、非常に有望である。
【0005】
ここで、有機電界発光素子は、一般に、2層構造〔ホール注入電極と電子注入電極との間に、ホール輸送層と、発光層とが形成された構造(SH−A構造)、またはホール注入電極と電子注入電極との間に、発光層と、電子輸送層とが形成された構造(SH−B構造)〕或いは3層構造〔ホール注入電極と電子注入電極との間に、ホール輸送層と、発光層と、電子輸送層とが形成された構造(DH構造)〕のような素子構造を有している。上記ホール注入電極としては、金やITOのような仕事関数の大きな電極材料を用い、上記電子注入電極としては、Mgのような仕事関数の小さな電極材料を用いる。また、上記ホール輸送層、発光層、電子輸送層には有機材料が用いられ、ホール輸送層はp型半導体の性質、電子輸送層はn型半導体の性質を有する材料が用いられる。上記発光層は、上記SH−A構造ではn型半導体の性質、SH−B構造ではp型半導体の性質、DH構造では中性に近い性質を有する材料が用いられる。いずれにしてもホール注入電極から注入されたホールと電子注入電極から注入された電子が発光層とホール(又は、電子)輸送層の界面、及び発光層内で再結合して発光するという原理である。
【0006】
【発明が解決しようとする課題】
ところで、上記有機電界発光素子の有機材料の選択は、素子の諸特性に大きく影響を与える。この諸特性の中でも、素子の耐久性の向上は重要な課題である。この耐久性を向上させる一つの方法として、有機電子輸送層に製膜性がよく、結晶化しにくい材料を用いる方法がある。
【0007】
現在、知られている比較的製膜性が良く、結晶化の起こりにくい化合物としては、特願平3−222793号に記載のオキサジアゾール系化合物がある。
しかしながら、この化合物を有機電子輸送層の材料として用いた電界発光素子も耐久性の良さは充分ではなく、更なる耐久性の向上が必要となっている。
本発明は、上記現状に鑑みなされたものであり、耐久性の高い電界発光素子を提供することを目的とする。
【0008】
【課題を解決するための手段】
上記目的を達成するために、請求項1の発明は、ホール注入電極と、電子注入電極との間に、有機発光層と有機電子輸送層とを備えた電界発光素子において、前記有機電子輸送層には、複数のオキサジアゾー ル環を1つのビフェニル基によって連結してなり、各オキサジアゾール環の置換基が3個以上のベンゼン環からなる縮合多環芳香族で構成されたオキサジアゾー ル系化合物が用いられていることを特徴とする。
【0009】
請求項2の発明は、請求項1記載の縮合多環芳香族が3個のベンゼン環からなるアントラセン、あるいはフェナントレンであることを特徴とする。
請求項3の発明は、請求項1記載の縮合多環芳香族が4個のベンゼン環からなるピレンであることを特徴とする。
【0012】
【作用】
上記のように構成することにより、以下のような作用が得られる。
先ず、本発明のオキサジアゾール系化合物は、分子内に嵩高い縮合多環芳香族基を有する。製膜された化合物の結晶化は、分子が規則正しく並ぶことによって起こるが、本発明のオキサジアゾール系化合物の場合、この嵩高い縮合多環芳香族基が分子が規則正しく並ぶことを邪魔することにより、製膜後も結晶化を起こしにくく製膜性がよい。
【0013】
加えて、本発明のオキサジアゾール系化合物は、膜形成を行なった際に、上記特願平3−222793号に記載のオキサジアゾール系化合物より、有機発光層に用いた化合物となじみが良く、製膜した後の膜の状態が良いという利点を有している。
ここで、本発明のオキサジアゾール系化合物は、一般に、下記化1或いは化2に示すような方法で合成する。尚、反応時間については、各々の化合物により異なっている。
【0014】
【化1】

Figure 0003547769
【0015】
【化2】
Figure 0003547769
【0016】
【実施例】
本発明の実施例を図面に基づいて以下に、説明を行なう。
(参考例1)
図1は、本発明の一実施例に係る電界発光素子の断面図であり、ガラス基板1
上には、ホール注入電極2と、有機ホール輸送層3と、有機発光層4と、有機電
子輸送層5と、電子注入電極6とが、ガラス基板1側から順に形成されている。
【0017】
それぞれの部材の材料としては、ホール注入電極2にはインジウム−スズ酸化物(ITO)、有機ホール輸送層3には下記化3に示すジアミン誘導体(TPD)、有機発光層4には下記化4に示すペリレン誘導体、有機電子輸送層5には下記化5に示すオキサジアゾール系化合物、電子注入電極6にはMgIn合金が、それぞれ用いられている。
【0018】
【化3】
Figure 0003547769
【0019】
【化4】
Figure 0003547769
【0020】
【化5】
Figure 0003547769
【0021】
ここで、上記構成の電界発光素子を、以下のようにして作製した。
先ず、ガラス基板1上にインジウム−スズ酸化物(ITO)からなるホール注入電極2が形成された基板を、中性洗剤、及び、水により洗浄した後、アセトン中で20分間、イソプロピルアルコール中で約20分間超音波洗浄をした。この後、上記ホール注入電極2上に、ジアミン誘導体(TPD 上記化3に示す)を真空蒸着して有機ホール輸送層3を形成した後、この有機ホール輸送層3上に、ペリレン誘導体(上記化4に示す)を真空蒸着して、有機発光層4を形成した。さらに、有機発光層4上にオキサジアゾール系化合物(上記化5に示す)を真空蒸着して有機電子輸送層5を作製した。しかる後、有機電子輸送層5上に、MgとInとを10:1の比率で共蒸着して、電子注入電極6を形成して、電界発光素子を作製した。尚、上記蒸着はいずれも、真空度1×10−6Torr、基板温度20℃、有機層の蒸着速度2Å/secという条件下で行った。
【0022】
ところで、上記オキサジアゾール系化合物の合成は、以下のようにして行った。
先ず、下記化6に示すように、市販のカルボキシル基を有する縮合多環芳香族化合物より、C. Gundu Rao等の方法(ORGANIC PREPARETIONS AND PROCEDURES INT. 12(3−4),P.225−228(1980))に基づいてエチルエステルを合成した。
【0023】
【化6】
Figure 0003547769
【0024】
続いて、下記化7に示すように、上記反応によって得られたエチルエステルを用いて浜田等の方法(日本化学会誌,1991,(11),p.1540−1548)に基づいて合成した。
【0025】
【化7】
Figure 0003547769
【0026】
このように作製した電界発光素子を、以下(a1 )素子と称する。
(参考例2)
有機電子輸送層の材料として、下記化8に示すオキサジアゾール系化合物を用いた以外は、上記参考例1と同様に素子を作製した。
(実施例1)
有機電子輸送層の材料として、下記化9に示すオキサジアゾール系化合物を用いた以外は、上記参考例1と同様に素子を作製した。
(参考例3)
有機電子輸送層の材料として、下記化10に示すオキサジアゾール系化合物を用いた以外は、上記参考例1と同様に素子を作製した。
【0027】
【化8】
Figure 0003547769
【0028】
【化9】
Figure 0003547769
【0029】
【化10】
Figure 0003547769
【0030】
また、オキサジアゾール系化合物の合成も上記参考例1の合成方法と同様の手
順で行なった。
このように作製した電界発光素子を、それぞれ以下(a2 )素子〜(a4 )素
子と称する。
(比較例1、2)
有機電子輸送層の材料として、下記化11、化12に示す縮合多環芳香族を有
していないオキサジアゾール系化合物を用いた以外は、上記参考例1と同様に素
子を作製した。
【0031】
【化11】
Figure 0003547769
【0032】
【化12】
Figure 0003547769
【0033】
このように、作製した電界発光素子を、それぞれ以下(x1 )素子、(x2 )
素子と称する。
〔実験1〕
上記参考例の(a 1 )(a 2 )(a 4 )素子、上記本発明の(a 3 )素子、及び、比較例の(x1 )素子、(x2 )素子を用いて、ホール注入電極2側にプラス、電子注入電極5側にマイナスを直流電圧として印加し、発光時間、最高輝度等の発光特性を調べたので、下記表1に示す。
【0034】
【表1】
Figure 0003547769
【0035】
発光色は、赤色で発光ピーク波長は630nmであった。
表1から明らかなように、本発明の(a3)素子は、比較例の(x1 )素子、(x2 )素子と比較して、発光時間が長かく、参考例と比べても最高輝度の値が最も高いことが分かる。これは、有機電子輸送層に用いたオキサジアゾール系化合物の製膜性が良く、結晶化しにくいため、化合物の結晶化による素子の破壊を抑えることができたためと考えられる。
【0036】
更に、製膜性の向上について調べるために、以下のような実験を行った。
〔実験2〕
上記(a)素子、(a)素子、及び、(x)素子(x)素子を用いて、製膜状態を調べたので、その結果を図2に示す。
具体的な実験条件としては、作成した素子を発光させずそのまま放置した場合の、素子1mm当たりの結晶領域の経時変化を調べた。
【0037】
図2から明らかなように、(x1 )素子(x2 )素子と比較して、参考例の(a1 )素子、(a4 )素子は、約1/2〜1/3結晶が発生しにくく、また結晶の成長も遅く製膜性が良いことがわかる。
〔その他の事項〕
上記実施例では素子構造が、3層構造についての説明を行なったが、2層構造の内でも、電子注入電極とホール注入電極との間に有機電子輸送層と、有機発光層とを有するSH−B構造のもので同様の効果を得ることができる。
【0038】
また、上記実施例では、縮合多環芳香族がアントラセン、または、ナフタレンであるオキサジアゾール系化合物についてしか述べていないが、本発明はこれに限らず、縮合多環芳香族としてフェナントレン、ピレンを用いることもできる。
これに加えて、複数のオキサジアゾール環の間に、アルキル鎖が存在するオキサジアゾール系化合物も用いることができる。
【0039】
更に、ホール注入電極として、上記実施例ではITO膜を用いたが、この他に金の半透明膜等、仕事関数が高く、透明性が高いものであれば用いることができる。
また、有機ホール輸送材料として、上記化1に示すジアミン誘導体(TPD)を用いたが、他の各種ジアミン誘導体(Y.Takeshita et.al.,Report on Progressin Polymer Physics in Japan,vol.30,503(1987))やポリビニルカルバゾール(T.Fujii et al.,J.PhotoPolymer Sci.and Tech.,vol.4,135(1991)) 等も用いることができる。
【0040】
【発明の効果】
以上説明したように、本発明によれば、製膜性に優れ、結晶化しにくい縮合多環芳香族基を有するオキサジアゾールを複数有したオキサジアゾール系化合物を、有機電子輸送層の材料として用いることにより、電界発光素子の耐久性が向上するという効果を奏した。
【図面の簡単な説明】
【図1】本発明の一例にかかる電界発光素子の断面図である。
【図2】電界発光素子1mm当たりの結晶領域の経時変化を示すグラフである。
【符号の説明】
1 ガラス基板
2 ホール注入電極
3 有機ホール輸送層
4 有機発光層
5 有機電子輸送層
6 電子注入電極[0001]
[Industrial applications]
The present invention relates to an electroluminescent device, and more particularly, to an organic electroluminescent device using a novel organic material for an organic electron transport layer.
[0002]
[Prior art]
2. Description of the Related Art In recent years, with the diversification of information devices, there is an increasing need for a flat display element having lower power consumption and a smaller space occupation volume than a CRT. As such a flat display element, there are a liquid crystal, a plasma display, and the like. In recent years, a self-luminous electroluminescent element with a clear display has attracted attention.
[0003]
Here, the electroluminescent element can be roughly classified into an inorganic electroluminescent element and an organic electroluminescent element depending on a constituent material, and the inorganic electroluminescent element has already been put to practical use.
However, the driving method of the inorganic electroluminescent element is a so-called collision excitation type light emission in which electrons accelerated by application of a high electric field collide and excite a light emission center to emit light, and therefore, it is necessary to drive at a high voltage. For this reason, there has been a problem that the cost of peripheral devices is increased.
[0004]
On the other hand, the organic electroluminescent element is a so-called injection type light emission in which charges injected from an electrode are recombined in a light emitting body to emit light, and thus can be driven at a low voltage. In addition, there is an advantage that any emission color can be easily obtained by changing the molecular structure of the organic compound. Therefore, the organic electroluminescent device is very promising as a future display device.
[0005]
Here, the organic electroluminescent element generally has a two-layer structure (a structure in which a hole transport layer and a light emitting layer are formed between a hole injection electrode and an electron injection electrode (SH-A structure), or a hole injection structure). A structure in which a light emitting layer and an electron transport layer are formed between an electrode and an electron injection electrode (SH-B structure)] or a three-layer structure [a hole transport layer between a hole injection electrode and an electron injection electrode] (DH structure) in which a light-emitting layer and an electron transport layer are formed]. An electrode material having a large work function such as gold or ITO is used as the hole injection electrode, and an electrode material having a small work function such as Mg is used as the electron injection electrode. An organic material is used for the hole transport layer, the light emitting layer, and the electron transport layer. A material having the property of a p-type semiconductor is used for the hole transport layer, and a material having the property of an n-type semiconductor is used for the electron transport layer. The light emitting layer is made of a material having the property of an n-type semiconductor in the SH-A structure, the property of a p-type semiconductor in the SH-B structure, and the property close to neutral in the DH structure. In any case, the principle is that holes injected from the hole injection electrode and electrons injected from the electron injection electrode recombine at the interface between the light emitting layer and the hole (or electron) transport layer and within the light emitting layer to emit light. is there.
[0006]
[Problems to be solved by the invention]
By the way, the selection of the organic material of the organic electroluminescent device greatly affects various characteristics of the device. Among these various characteristics, improvement of the durability of the element is an important issue. As one method of improving the durability, there is a method of using a material having good film-forming properties and being hardly crystallized for the organic electron transport layer.
[0007]
Oxadiazole compounds described in Japanese Patent Application No. 3-222793 are currently known as compounds having relatively good film-forming properties and hardly causing crystallization.
However, an electroluminescent device using this compound as a material for an organic electron transport layer does not have sufficient durability, and further improvement in durability is required.
The present invention has been made in view of the above situation, and has as its object to provide a highly durable electroluminescent device.
[0008]
[Means for Solving the Problems]
In order to achieve the above object, the invention according to claim 1 is an electroluminescent device comprising an organic light emitting layer and an organic electron transport layer between a hole injection electrode and an electron injection electrode. Contains several oxadiazo Oxadiazole compounds in which the oxa rings are linked by one biphenyl group, and the substituent of each oxadiazole ring is composed of a condensed polycyclic aromatic ring composed of three or more benzene rings. Features.
[0009]
The invention according to claim 2 is characterized in that the fused polycyclic aromatic according to claim 1 is anthracene or phenanthrene composed of three benzene rings.
The invention of claim 3 is characterized in that the fused polycyclic aromatic according to claim 1 is pyrene comprising four benzene rings.
[0012]
[Action]
With the above configuration, the following operation can be obtained.
First, the oxadiazole-based compound of the present invention has a bulky condensed polycyclic aromatic group in the molecule. Crystallization of the formed compound occurs when the molecules are regularly arranged.In the case of the oxadiazole-based compound of the present invention, the bulky condensed polycyclic aromatic group prevents the molecules from being regularly arranged. In addition, crystallization hardly occurs even after film formation, and the film forming property is good.
[0013]
In addition, the oxadiazole-based compound of the present invention is more compatible with the compound used in the organic light-emitting layer than the oxadiazole-based compound described in Japanese Patent Application No. 3-222793 when a film is formed. This has the advantage that the state of the film after film formation is good.
Here, the oxadiazole-based compound of the present invention is generally synthesized by a method shown in Chemical Formula 1 or Chemical Formula 2 below. The reaction time differs depending on each compound.
[0014]
Embedded image
Figure 0003547769
[0015]
Embedded image
Figure 0003547769
[0016]
【Example】
Embodiments of the present invention will be described below with reference to the drawings.
(Reference Example 1)
FIG. 1 is a cross-sectional view of an electroluminescent device according to one embodiment of the present invention.
On the top, a hole injection electrode 2, an organic hole transport layer 3, an organic light emitting layer 4, an organic electron transport layer 5, and an electron injection electrode 6 are sequentially formed from the glass substrate 1 side.
[0017]
The material of each member is indium-tin oxide (ITO) for the hole injection electrode 2, diamine derivative (TPD) shown in the following formula 3 for the organic hole transport layer 3, and the following formula 4 for the organic light emitting layer 4. , An oxadiazole-based compound shown in Chemical Formula 5 below, and an MgIn alloy for the electron injection electrode 6.
[0018]
Embedded image
Figure 0003547769
[0019]
Embedded image
Figure 0003547769
[0020]
Embedded image
Figure 0003547769
[0021]
Here, the electroluminescent device having the above configuration was produced as follows.
First, a substrate on which a hole injection electrode 2 made of indium-tin oxide (ITO) is formed on a glass substrate 1 is washed with a neutral detergent and water, and then in acetone for 20 minutes and in isopropyl alcohol. Ultrasonic cleaning was performed for about 20 minutes. Thereafter, a diamine derivative (TPD shown in the above formula 3) is vacuum-deposited on the hole injecting electrode 2 to form an organic hole transport layer 3, and then a perylene derivative (the above 4) was vacuum-deposited to form an organic light emitting layer 4. Further, an oxadiazole-based compound (shown in Chemical Formula 5) was vacuum-deposited on the organic light-emitting layer 4 to form an organic electron transport layer 5. Thereafter, Mg and In were co-deposited on the organic electron transporting layer 5 at a ratio of 10: 1 to form the electron injection electrode 6, thereby producing an electroluminescent device. Note that all of the above vapor depositions were performed under the conditions of a degree of vacuum of 1 × 10 −6 Torr, a substrate temperature of 20 ° C., and a vapor deposition rate of an organic layer of 2 ° / sec.
[0022]
By the way, the synthesis of the oxadiazole-based compound was performed as follows.
First, as shown in the following chemical formula 6, a commercially available condensed polycyclic aromatic compound having a carboxyl group is converted to C.I. Ethyl esters were synthesized based on the method of Gundu Rao et al. (ORGANIC PREPARATIONS AND PROCEDURES INT. 12 (3-4), P. 225-228 (1980)).
[0023]
Embedded image
Figure 0003547769
[0024]
Subsequently, as shown in the following Chemical Formula 7, the ethyl ester obtained by the above reaction was used to synthesize according to the method of Hamada et al. (Journal of the Chemical Society of Japan, 1991, (11), pp. 1540-1548).
[0025]
Embedded image
Figure 0003547769
[0026]
The electroluminescent device manufactured in this manner is hereinafter referred to as (a1) device.
(Reference Example 2)
A device was manufactured in the same manner as in Reference Example 1 except that an oxadiazole-based compound represented by Chemical Formula 8 below was used as a material for the organic electron transport layer.
(Example 1)
A device was produced in the same manner as in Reference Example 1 except that an oxadiazole-based compound represented by Chemical Formula 9 below was used as a material for the organic electron transporting layer.
(Reference Example 3)
A device was produced in the same manner as in Reference Example 1 except that an oxadiazole-based compound represented by Chemical Formula 10 below was used as a material for the organic electron transporting layer.
[0027]
Embedded image
Figure 0003547769
[0028]
Embedded image
Figure 0003547769
[0029]
Embedded image
Figure 0003547769
[0030]
Further, the synthesis of the oxadiazole-based compound was performed in the same procedure as the synthesis method of Reference Example 1 described above.
The electroluminescent devices thus manufactured are hereinafter referred to as (a2) device to (a4) device, respectively.
(Comparative Examples 1 and 2)
An element was fabricated in the same manner as in Reference Example 1 except that an oxadiazole-based compound having no condensed polycyclic aromatic compound shown in Chemical Formulas 11 and 12 below was used as a material for the organic electron transport layer.
[0031]
Embedded image
Figure 0003547769
[0032]
Embedded image
Figure 0003547769
[0033]
The electroluminescent devices thus manufactured were respectively referred to as (x1) device and (x2)
It is called an element.
[Experiment 1]
Using the (a 1 ), (a 2 ), and (a 4 ) elements of the reference example, the (a 3 ) element of the present invention , and the (x 1) and (x 2) elements of the comparative example, a hole injection electrode 2 was prepared. The positive side and the negative side as a DC voltage were applied to the electron injection electrode 5 side, and the light emission characteristics such as the light emission time and the maximum luminance were examined.
[0034]
[Table 1]
Figure 0003547769
[0035]
The luminescent color was red and the luminescent peak wavelength was 630 nm.
As is clear from Table 1, the (a3) device of the present invention has a longer light emission time than the (x1) device and the (x2) device of the comparative examples, and has the highest luminance value as compared with the reference example. Is the highest. This is presumably because the oxadiazole-based compound used for the organic electron transporting layer had good film-forming properties and was difficult to crystallize, so that destruction of the element due to crystallization of the compound could be suppressed.
[0036]
Further, the following experiment was conducted in order to examine the improvement of the film forming property.
[Experiment 2]
Using (a 1 ) element, (a 4 ) element, and (x 1 ) element (x 2 ) element, the film formation state was examined. The results are shown in FIG.
As a specific experimental condition, a change with time of a crystal region per 1 mm 2 of the device when the formed device was left as it was without emitting light was examined.
[0037]
As is apparent from FIG. 2, the (a1) element and the (a4) element of the reference example are less likely to generate about 1/2 to 1/3 crystals as compared with the (x1) element (x2) element. It can be seen that the crystal growth is slow and the film forming property is good.
[Other matters]
In the above embodiment, the description has been given of the case where the element structure is the three-layer structure. However, even in the two-layer structure, the SH having the organic electron transport layer and the organic light emitting layer between the electron injection electrode and the hole injection electrode is used. The same effect can be obtained with the -B structure.
[0038]
Further, in the above examples, the condensed polycyclic aromatic is anthracene or an oxadiazole-based compound which is naphthalene, but the present invention is not limited thereto, and phenanthrene and pyrene are used as condensed polycyclic aromatics. It can also be used.
In addition, an oxadiazole compound having an alkyl chain between a plurality of oxadiazole rings can be used.
[0039]
Further, although an ITO film is used in the above embodiment as the hole injection electrode, other materials having a high work function and high transparency, such as a gold translucent film, can be used.
Further, the diamine derivative (TPD) shown in Chemical Formula 1 was used as the organic hole transport material, but other various diamine derivatives (Y. Takeshita et. Al., Report on Progressin Polymer Physics in Japan, vol. 30, 503). (1987)) and polyvinyl carbazole (T. Fujii et al., J. Photo Polymer Sci. And Tech., Vol. 4, 135 (1991)).
[0040]
【The invention's effect】
As described above, according to the present invention, an oxadiazole-based compound having a plurality of oxadiazoles having a condensed polycyclic aromatic group that is excellent in film-forming properties and is difficult to crystallize is used as a material for an organic electron transporting layer. The use of such a material has the effect of improving the durability of the electroluminescent device.
[Brief description of the drawings]
FIG. 1 is a cross-sectional view of an electroluminescent device according to an example of the present invention.
FIG. 2 is a graph showing a change over time of a crystal region per 1 mm 2 of an electroluminescent element.
[Explanation of symbols]
REFERENCE SIGNS LIST 1 glass substrate 2 hole injection electrode 3 organic hole transport layer 4 organic light emitting layer 5 organic electron transport layer 6 electron injection electrode

Claims (3)

ホール注入電極と、電子注入電極との間に、有機発光層と有機電子輸送層とを備えた電界発光素子において、前記有機電子輸送層には、複数のオキサジアゾーAn electroluminescent device including an organic light emitting layer and an organic electron transport layer between a hole injection electrode and an electron injection electrode, wherein the organic electron transport layer includes a plurality of oxadiazo ル環を1つのビフェニル基によって連結してなり、各オキサジアゾール環の置換基が3個以上のベンゼン環からなる縮合多環芳香族で構成されたオキサジアゾーOxadiazols in which each of the oxadiazole rings is a condensed polycyclic aromatic ring composed of three or more benzene rings. ル系化合物が用いられていることを特徴とする電界発光素子。An electroluminescent device characterized by using a metal compound. 上記縮合多環芳香族が、3個のベンゼン環からなるアントラセン、あるいはフェナントレンであることを特徴とする請求項1記載の電界発光素子。The electroluminescent device according to claim 1, wherein the condensed polycyclic aromatic is anthracene comprising three benzene rings or phenanthrene. 上記縮合多環芳香族が、4個のベンゼン環からなるピレンであることを特徴とする請求項1記載の電界発光素子。The electroluminescent device according to claim 1, wherein the condensed polycyclic aromatic is pyrene comprising four benzene rings.
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