JP2001172232A - Electroluminescent element - Google Patents
Electroluminescent elementInfo
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- JP2001172232A JP2001172232A JP36278499A JP36278499A JP2001172232A JP 2001172232 A JP2001172232 A JP 2001172232A JP 36278499 A JP36278499 A JP 36278499A JP 36278499 A JP36278499 A JP 36278499A JP 2001172232 A JP2001172232 A JP 2001172232A
- Authority
- JP
- Japan
- Prior art keywords
- hole transport
- transport layer
- biphenyl
- organic compound
- tris
- 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.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、エレクトロルミネ
ッセンス素子に関し、さらに詳しくは、フルカラーのフ
ラットパネルディスプレイなどに好適に使用することの
できるエレクトロルミネッセンス素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electroluminescent device, and more particularly, to an electroluminescent device that can be suitably used for a full-color flat panel display and the like.
【０００２】[0002]
【従来の技術】近年のフルカラーのフラットパネルディ
スプレイなどの発達に伴って、有機エレクトロルミネッ
センス素子（以下、略して「ＥＬ素子」という場合があ
る）には、高輝度・高効率発光のみならず、高耐熱性・
高耐久性が求められている。例えば、カーナビゲーショ
ンシステムへの応用に関しては１００℃以上の耐熱性が
求められている。このため、ＥＬ素子を構成する正孔輸
送層にも高い耐熱性と耐久性が求められているが、正孔
輸送層用の材料としては、これまでにいくつかの有機金
属錯体並びにπ共役系分子が報告されているのみであ
る。2. Description of the Related Art With the development of full-color flat panel displays and the like in recent years, organic electroluminescent devices (hereinafter sometimes abbreviated as "EL devices") not only emit light with high luminance and efficiency but also emit light. High heat resistance
High durability is required. For example, heat resistance of 100 ° C. or higher is required for application to a car navigation system. For this reason, high heat resistance and high durability are also required for the hole transport layer constituting the EL element. However, as materials for the hole transport layer, some organometallic complexes and π-conjugated Only the molecule has been reported.
【０００３】[0003]
【発明が解決しようとする課題】上記のような有機化合
物材料は、モルフォルジー安定性や耐熱性に乏しいもの
である。したがって、発光輝度及び発光効率が高く、耐
熱性並びに耐久性に優れる正孔輸送層用材料を得ること
ができないのが現状であった。このため、上記フルカラ
ーのフラットパネルディスプレイなどの実用に供するこ
とのできるＥＬ素子を得ることができないでいた。The above-mentioned organic compound materials have poor morphological stability and heat resistance. Therefore, at present, it is impossible to obtain a material for a hole transport layer having high light emission luminance and light emission efficiency and excellent heat resistance and durability. For this reason, it has not been possible to obtain an EL element which can be put to practical use such as the above-mentioned full-color flat panel display.
【０００４】本発明は、高い発光輝度並びに高い発光効
率を有するとともに、耐熱性や耐久性にも優れた新規な
ＥＬ素子、並びにかかるＥＬ素子を実現するための新規
な正孔輸送層用の有機化合物材料を提供することを目的
とする。The present invention relates to a novel EL device having high luminous luminance and high luminous efficiency, and also having excellent heat resistance and durability, and a novel organic material for a hole transport layer for realizing such an EL device. It is intended to provide a compound material.
【０００５】[0005]
【課題を解決するための手段】本発明のＥＬ素子は、基
板と、透明電極と、正孔輸送層と、発光層と、背面電極
とを具え、これらがこの順に積層されて構成されてい
る。そして、前記正孔輸送層が、4、4'、4''-トリス
［ビフェニル-2-イル（フェニル）アミノ］トリフェニ
ルアミン及び4、4'、4''-トリス［ビフェニル-4-イル
（3-メチルフェニル）アミノ］トリフェニルアミンなる
有機化合物材料の少なくとも一方から構成されているこ
とを特徴とする。The EL device of the present invention comprises a substrate, a transparent electrode, a hole transport layer, a light emitting layer, and a back electrode, which are stacked in this order. . Then, the hole transport layer is composed of 4,4 ′, 4 ″ -tris [biphenyl-2-yl (phenyl) amino] triphenylamine and 4,4 ′, 4 ″ -tris [biphenyl-4-yl (3-methylphenyl) amino] triphenylamine.
【０００６】本発明者らは、発光強度及び発光効率に優
れ、さらには耐熱性や耐久性にも優れた新規なＥＬ素子
を開発すべく鋭意検討した。その結果、基板と、透明電
極と、正孔輸送層と、発光層と、背面電極とを具えるＥ
Ｌ素子において、前記正孔輸送層を上述したような特定
の有機化合物材料から構成するのみで前記のようなＥＬ
素子が得られることを見出したものである。[0006] The present inventors have intensively studied to develop a new EL device which is excellent in luminous intensity and luminous efficiency, and furthermore excellent in heat resistance and durability. As a result, an E including a substrate, a transparent electrode, a hole transport layer, a light emitting layer, and a back electrode is provided.
In the L element, the above-described EL can be obtained by merely forming the hole transport layer from the specific organic compound material as described above.
It has been found that an element can be obtained.
【０００７】4、4'、4''-トリス［ビフェニル-2-イル
（フェニル）アミノ］トリフェニルアミン（以下、略し
て、「o-PTDATA」という場合がある）及び4、4'、4''-
トリス［ビフェニル-4-イル（3-メチルフェニル）アミ
ノ］トリフェニルアミン（以下、略して、「p-PMTDAT
A」という場合がある）は、本発明者らが、新たに合成
して作り出した新規な有機化合物である。そして、合成
時において、この新規な有機化合物のガラス転移温度が
それぞれ約９３℃及び約１１０℃であり、高い温度まで
アモルファス状態の保持が可能であることを確認した。
さらに、これらの有機化合物は真空蒸着法を用いること
により、均一かつ透明なアモルファス膜を容易に形成で
きることをも確認した。4,4 ′, 4 ″ -Tris [biphenyl-2-yl (phenyl) amino] triphenylamine (hereinafter sometimes abbreviated as “o-PTDATA”) and 4,4 ′, 4 ''-
Tris [biphenyl-4-yl (3-methylphenyl) amino] triphenylamine (hereinafter abbreviated as “p-PMTDAT
A) is a novel organic compound newly synthesized and created by the present inventors. At the time of synthesis, the glass transition temperature of this novel organic compound was about 93 ° C. and about 110 ° C., respectively, and it was confirmed that the amorphous state could be maintained up to a high temperature.
Furthermore, it was also confirmed that a uniform and transparent amorphous film can be easily formed from these organic compounds by using a vacuum evaporation method.
【０００８】そこで、本発明者らは、この新規な有機化
合物をＥＬ素子の正孔輸送層に使用した場合において、
発光輝度並びに発光効率がどのように変化するか検討し
た。その結果、上記の正孔輸送層を有する構成のＥＬ素
子において、驚くべきことに、o-PTDATA及びp-PMTDATA
のそれぞれにおいて約１６０００ｃｄ／ｍ２以上の発光
輝度、及び約１．２ｌｍ／Ｗ以上の発光効率が得られる
ことを見出した。そして、これらo-PTDATA及びp-PMTDAT
Aが本来的に有する高いガラス転位温度に起因した高い
耐熱性及び耐久性と相伴って、これらの有機化合物が上
記構成のＥＬ素子の正孔輸送層用材料として極めて優れ
ていることを見出したものである。[0008] Then, the present inventors, when using this novel organic compound for the hole transport layer of the EL device,
We examined how the luminous brightness and luminous efficiency change. As a result, surprisingly, in the EL device having the above-described structure having the hole transport layer, o-PTDATA and p-PMTDATA
It was found that in each of the above, a light emission luminance of about 16000 cd / m 2 or more and a light emission efficiency of about 1.2 lm / W or more were obtained. And these o-PTDATA and p-PMTDAT
Along with the high heat resistance and durability due to the high glass transition temperature that A originally has, these organic compounds have been found to be extremely excellent as a material for the hole transport layer of the EL device having the above structure. Things.
【０００９】o-PTDATA及びp-PMTDATAを上記構成のＥＬ
素子の正孔輸送層として使用した場合において、高い発
光輝度と高い発光効率とを示す原因について明確ではな
いが、o-PTDATA及びp-PMTDATAが低いイオン化ポテンシ
ャルと高い正孔移動度を有していることが原因と推定さ
れる。[0009] The o-PTDATA and p-PMTDATA are converted to EL
When used as a hole transport layer of the device, it is not clear about the cause of high luminous brightness and high luminous efficiency, but o-PTDATA and p-PMTDATA have low ionization potential and high hole mobility. It is presumed to be the cause.
【００１０】[0010]
【発明の実施の形態】本発明を発明の実施の形態に基づ
いて詳細に説明する。図１は、本発明のＥＬ素子構成の
一例を示す概略図である。以下、図１に示すＥＬ素子構
成に基づき、本発明を詳細に説明する。図１に示すＥＬ
素子１０は、ガラス基板１と、透明電極としてのＩＴＯ
電極２と、第１の正孔輸送層３と、第２の正孔輸送層４
とを具えている。さらに、発光層５と、背面電極として
のＭｇＡｇ電極６とを具えている。そして、これらがこ
の順に積層されている。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described in detail based on embodiments of the present invention. FIG. 1 is a schematic diagram showing an example of the EL element configuration of the present invention. Hereinafter, the present invention will be described in detail based on the EL element configuration shown in FIG. EL shown in FIG.
The element 10 includes a glass substrate 1 and ITO as a transparent electrode.
Electrode 2, first hole transport layer 3, and second hole transport layer 4
With Further, it has a light emitting layer 5 and an MgAg electrode 6 as a back electrode. These are stacked in this order.
【００１１】第１の正孔輸送層３は、本発明にしたがっ
てo-PTDATA及びp-PMTDATAの少なくとも一方の有機化合
物から構成されている。これら有機化合物は以下に示す
ような構造を呈する。The first hole transport layer 3 is composed of at least one of o-PTDATA and p-PMTDATA organic compounds according to the present invention. These organic compounds have the following structures.
【００１２】[0012]
【化１】 Embedded image
【００１３】[0013]
【化２】 Embedded image
【００１４】o-PTDATAは、次のようにして製造する。す
なわち、4、4'、4''-トリヨードトリフェニルアミンを
メシチレン溶媒に溶解して得た溶液に、N-フェニル-2-
ビフェニリルアミン、炭酸カリウム、銅粉、及び18-ク
ラウン-6を加えて窒素雰囲気中で加熱撹拌し、溶媒を除
去する。そして、シリカゲルカラムクロマトグラフィ、
トルエン及びヘキサンとの混合溶媒からの再結晶により
精製して得る。p-PMTDATAは、上記N-フェニル-2-ビフェ
ニリルアミンに代えて、N-3-メチルフェニル-4-ビフェ
ニリルアミンを用いることによって得ることができる。[0014] The o-PTDATA is manufactured as follows. That is, a solution obtained by dissolving 4,4 ′, 4 ''-triiodotriphenylamine in a mesitylene solvent is added with N-phenyl-2-
Biphenylylamine, potassium carbonate, copper powder, and 18-crown-6 are added, and the mixture is heated and stirred in a nitrogen atmosphere to remove the solvent. And silica gel column chromatography,
It is obtained by purification by recrystallization from a mixed solvent of toluene and hexane. p-PMTDATA can be obtained by using N-3-methylphenyl-4-biphenylylamine instead of N-phenyl-2-biphenylylamine.
【００１５】第２の正孔輸送層４を構成する材料は、本
発明の目的を達成することができれば特には限定されな
い。例えば、N,N'-ビス（3-メチルフェニル）-N,N'-ジ
フェニル-(1,1'-ビフェニル)-4,4'-ジアミン及びN,N'-
ジ（1-ナフチル）-N,N'-ジフェニル-（1,1'−ビフェニ
ル）-4,4'-ジアミンなどの公知のπ共役系分子を用いる
ことができる。しかしながら、耐熱性に優れることか
ら、第２の正孔輸送層４は、N、N'-ジ（ビフェニル-4-
イル）-N、N'-ジフェニル-［1，1'-ビフェニル］-4，4'
-ジアミン（以下、略して「p-BPD」という場合がある）
なる有機化合物材料から構成することが好ましい。p-BP
D自体は公知の有機化合物であるが、かかる化合物は主
に電子写真感光体の分野で使用されており、ＥＬ素子に
おいては本発明者らが初めて応用し、上記のような特質
を見出したものである。The material constituting the second hole transport layer 4 is not particularly limited as long as the object of the present invention can be achieved. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine and N, N'-
Known π-conjugated molecules such as di (1-naphthyl) -N, N′-diphenyl- (1,1′-biphenyl) -4,4′-diamine can be used. However, because of its excellent heat resistance, the second hole transport layer 4 is made of N, N′-di (biphenyl-4-
Yl) -N, N'-diphenyl- [1,1'-biphenyl] -4,4 '
-Diamine (hereinafter sometimes abbreviated as "p-BPD")
It is preferable to be composed of an organic compound material. p-BP
D itself is a known organic compound, but such a compound is mainly used in the field of an electrophotographic photoreceptor, and the present inventors have applied the EL device for the first time and found the above-mentioned characteristics. It is.
【００１６】p-BPDは以下のような構造式を有し、次の
ようにして製造する。すなわち、N,N'-ジフェニルベン
ジンをメシチレン溶媒に溶解して得た溶液に、4-ヨード
ビフェニル、炭酸カリウム、銅粉、及び18-クラウン-6
を加えて窒素雰囲気中で加熱撹拌する。反応終了後溶媒
を除去し、シリカゲルカラムクロマトグラフィ、トルエ
ン及びヘキサンとの混合溶媒からの再結晶により精製し
て得る。[0016] p-BPD has the following structural formula and is manufactured as follows. That is, 4-iodobiphenyl, potassium carbonate, copper powder, and 18-crown-6 were added to a solution obtained by dissolving N, N'-diphenylbenzine in a mesitylene solvent.
And heating and stirring in a nitrogen atmosphere. After completion of the reaction, the solvent is removed and the product is purified by silica gel column chromatography and recrystallized from a mixed solvent of toluene and hexane.
【００１７】[0017]
【化３】 Embedded image
【００１８】第２の正孔輸送層４をこのような公知の有
機化合物材料から構成した場合においても、第１の正孔
輸送層３が本発明にしたがってo-PTDATA及びp-PMTDATA
の少なくとも一方から構成される、すなわち、正孔輸送
層の少なくとも一部がこれらの有機化合物から構成され
ることにより、本発明の目的であるＥＬ素子の高発光輝
度及び高発光効率が達成される。また、正孔輸送層全体
のガラス転移温度も比較的高い温度に維持されるため、
耐熱性及び耐久性に優れるＥＬ素子をも提供することが
できる。Even when the second hole transporting layer 4 is made of such a known organic compound material, the first hole transporting layer 3 is formed by o-PTDATA and p-PMTDATA according to the present invention.
In other words, when the hole transport layer is formed of at least one of these organic compounds, the EL device of the present invention achieves high luminance and high luminous efficiency. . In addition, the glass transition temperature of the entire hole transport layer is also maintained at a relatively high temperature,
An EL element having excellent heat resistance and durability can be provided.
【００１９】図１に示すＥＬ素子１０は、正孔輸送層を
第１の輸送層３と第２の輸送層４とから構成し、この第
１の正孔輸送層３を本発明にしたがってo-PTDATA及びp-
PMTDATAの少なくとも一方から構成している。しかしな
がら、正孔輸送層は、このように２つに分割して構成す
ることは必ずしも要求されない。本発明の目的を達成す
べく、正孔輸送層の少なくとも一部がo-PTDATA及びp-PM
TDATAの少なくとも一方の有機化合物材料から構成され
ていれば良い。また、正孔輸送層を３つ以上の層から構
成しても良い。In the EL element 10 shown in FIG. 1, the hole transport layer is composed of a first transport layer 3 and a second transport layer 4, and the first hole transport layer 3 is formed according to the present invention. -PTDATA and p-
It consists of at least one of PMTDATA. However, the hole transport layer is not necessarily required to be divided into two as described above. In order to achieve the object of the present invention, at least a part of the hole transport layer has o-PTDATA and p-PM
What is necessary is just to be comprised from at least one organic compound material of TDATA. Further, the hole transport layer may be composed of three or more layers.
【００２０】正孔輸送層を２つの正孔輸送層から構成す
る場合、図１に示すように、o-PTDATA及びp-PMTDATAの
少なくとも一方の有機化合物材料からなる第１の正孔輸
送層３を基板側に形成し、第２の正孔輸送層４を基板と
は反対側に形成する、すなわち、第１の正孔輸送層３及
び第２の正孔輸送層４を基板１の上方においてこの順に
形成することが好ましい。これにより、発光層の正孔注
入を容易に行うことができる。When the hole transport layer is composed of two hole transport layers, as shown in FIG. 1, the first hole transport layer 3 made of at least one organic compound material of o-PTDATA and p-PMTDATA is used. Is formed on the substrate side, and the second hole transport layer 4 is formed on the side opposite to the substrate. That is, the first hole transport layer 3 and the second hole transport layer 4 are formed above the substrate 1. It is preferable to form them in this order. Thus, holes can be easily injected into the light emitting layer.
【００２１】この場合において、第１の正孔輸送層３の
厚さは１００〜５００Åであることが好ましく、さらに
は２００〜３００Åであることが好ましい。また、第２
の正孔輸送層４の厚さは１００〜５００Åであることが
好ましく、さらには２００〜３００Åであることが好ま
しい。これにより、低電圧で高発光輝度及び高発光効率
の発光を得ることができる。また、第２の正孔輸送層４
にp-BPDを使用した場合において、上記のような発光層
への正孔注入を容易にすることができる。In this case, the thickness of the first hole transport layer 3 is preferably 100 to 500 °, more preferably 200 to 300 °. Also, the second
The hole transport layer 4 preferably has a thickness of 100 to 500 °, more preferably 200 to 300 °. Thus, light emission with high luminance and high light emission efficiency can be obtained at a low voltage. Further, the second hole transport layer 4
In the case where p-BPD is used, hole injection into the light emitting layer as described above can be facilitated.
【００２２】図１に示すＥＬ素子１０の発光層５につい
ても、本発明の目的を達成することのできる、ガラス転
移温度が比較的高い公知の材料から構成することができ
る。特に、トリス（8-キノリノラト）アルミニウム（以
下、略して「Alq3」という場合がある）なる有機化合物
材料から構成することが好ましい。この有機化合物材料
は、ＥＬ素子の発光層用材料として公知であり、比較的
高いガラス転移温度（約１７０℃）を有するとともに、
高い発光輝度と高い発光効率とを有する。したがって、
本発明の目的をさらに効果的に達成することができる。The light emitting layer 5 of the EL device 10 shown in FIG. 1 can also be made of a known material having a relatively high glass transition temperature, which can achieve the object of the present invention. In particular, it is preferable to use an organic compound material of tris (8-quinolinolato) aluminum (hereinafter, sometimes abbreviated as “Alq 3 ”). This organic compound material is known as a material for a light emitting layer of an EL device, has a relatively high glass transition temperature (about 170 ° C.), and
It has high light emission luminance and high light emission efficiency. Therefore,
The object of the present invention can be achieved more effectively.
【００２３】また、このような有機化合物材料からなる
発光層に用いた場合、この発光層の厚さは２００〜１０
００Åであることが好ましく、さらには３００〜６００
Åであることが好ましい。When used in a light emitting layer made of such an organic compound material, the thickness of the light emitting layer is 200 to 10
00 °, preferably 300 to 600
Å is preferred.
【００２４】Alq3は、以下のような構造を示し、次のよ
うにして製造する。すなわち、8-キノリノールと水酸化
ナトリウムを溶解させた水溶液に、塩化アルミニウム・
６水和物の水溶液を徐々に加え、撹拌する。得られた淡
黄色の析出物を濾取し、水でよく洗浄した後、昇華精製
を繰り返して行い、精製して得る。Alq 3 has the following structure and is manufactured as follows. That is, an aqueous solution of 8-quinolinol and sodium hydroxide dissolved in aluminum chloride
An aqueous solution of hexahydrate is slowly added and stirred. The obtained pale yellow precipitate is collected by filtration, washed well with water, and then repeatedly purified by sublimation to obtain a purified product.
【００２５】[0025]
【化４】 Embedded image
【００２６】なお、基板には図１に示すようなガラス基
板の他にＰＥＴフィルムなどを使用することができる。
また、透明電極についても、ＩＴＯ電極の他にダイアモ
ンドなどを使用することができる。さらに、背面電極に
ついてもＭｇＡｇ電極の他に、Ｃａ、Ａｌなどを使用す
ることができる。In addition, a PET film or the like can be used for the substrate in addition to the glass substrate shown in FIG.
Also, as the transparent electrode, diamond or the like can be used in addition to the ITO electrode. Further, for the back electrode, Ca, Al or the like can be used in addition to the MgAg electrode.
【００２７】[0027]
【実施例】以下、実施例により本発明のＥＬ素子の具体
例を示す。 実施例 本実施例においては、図１に示すようなＥＬ素子１０を
作製した。以下、ＥＬ素子１０の製造過程を順を追って
示す。EXAMPLES Specific examples of the EL device of the present invention will be described below with reference to examples. Example In this example, an EL element 10 as shown in FIG. 1 was manufactured. Hereinafter, the manufacturing process of the EL element 10 will be described step by step.
【００２８】（o-PTDATAの合成）4、4'、4''-トリヨー
ドトリフェニルアミン１２ｇをメシチレン溶媒に溶解し
て得た溶液に、N-フェニル-4-ビフェニリルアミン１０
ｇ、炭酸カリウム３０ｇ、銅粉１０ｇ、及び18-クラウ
ン-6の０．５ｇを加えて窒素雰囲気中、１７０℃で２５
時間加熱撹拌した。そして、溶媒を留去した後、シリカ
ゲルカラムクロマトグラフィ、トルエン及びヘキサンと
の混合溶媒からの再結晶により精製し、１．０ｇのo-PT
DATAを得た。(Synthesis of o-PTDATA) N-phenyl-4-biphenylylamine was added to a solution obtained by dissolving 12 g of 4,4 ′, 4 ″ -triiodotriphenylamine in a mesitylene solvent.
g, 30 g of potassium carbonate, 10 g of copper powder, and 0.5 g of 18-crown-6 at 25 ° C. in a nitrogen atmosphere at 170 ° C.
The mixture was heated and stirred for an hour. After distilling off the solvent, the residue was purified by silica gel column chromatography, recrystallization from a mixed solvent of toluene and hexane, and 1.0 g of o-PT
I got DATA.
【００２９】（p-PMTDATAの合成）4、4'、4''-トリヨー
ドトリフェニルアミン２１ｇをメシチレン溶媒に溶解し
て得た溶液に、N-3-メチルフェニル-4-ビフェニリルア
ミン４２ｇ、炭酸カリウム４７ｇ、銅粉５ｇ、及び18-
クラウン-6の０．５ｇを加えて窒素雰囲気中、１７０℃
で１０時間加熱撹拌した。溶媒を留去した後、シリカゲ
ルカラムクロマトグラフィ、トルエン及びヘキサンとの
混合溶媒からの再結晶により精製し、１．０ｇのp-PMTD
ATAを得た。(Synthesis of p-PMTDATA) A solution obtained by dissolving 21 g of 4,4 ′, 4 ″ -triiodotriphenylamine in a mesitylene solvent was charged with 42 g of N-3-methylphenyl-4-biphenylylamine. , Potassium carbonate 47g, copper powder 5g, and 18-
Add 0.5g of Crown-6 and add 170g in nitrogen atmosphere
For 10 hours. After evaporating the solvent, the residue was purified by silica gel column chromatography, recrystallization from a mixed solvent of toluene and hexane, and 1.0 g of p-PMTD
Got ATA.
【００３０】（ＥＬ素子の作製）ＩＴＯ電極２が形成さ
れた市販のガラス基板１を用い、このＩＴＯ電極２上
に、上記のようにして合成して得た粉末状のo-PTDATA又
はp-PMTDATAを蒸着源として用い、真空蒸着によって厚
さ３００Åのo-PTDATA又はp-PMTDATAからなる第１の正
孔輸送層３を形成した。次いで、粉末状のp-BPDを蒸着
源として用いることにより、蒸着法によって厚さ２００
Åのp-BPDからなる第２の正孔輸送層４を形成した。そ
の後、粉末状のAlq3を蒸着源として用いることにより、
蒸着法によって厚さ５００ÅのAlq3からなる発光層５を
形成した。次いで、同じく蒸着法によってＭｇＡｇ電極
６（Ｍｇの体積：Ａｇの体積＝１０：１）を厚さ１００
０Åに形成し、ＥＬ素子１０を得た。(Production of EL Element) Using a commercially available glass substrate 1 on which an ITO electrode 2 was formed, a powdery o-PTDATA or p- Using PMTDATA as an evaporation source, a first hole transport layer 3 made of o-PTDATA or p-PMTDATA having a thickness of 300 ° was formed by vacuum evaporation. Next, by using p-BPD in powder form as an evaporation source, a thickness of 200 μm was obtained by an evaporation method.
The second hole transporting layer 4 composed of p-BPD was formed. After that, by using powdered Alq 3 as an evaporation source,
A light emitting layer 5 made of Alq 3 having a thickness of 500 ° was formed by a vapor deposition method. Next, an MgAg electrode 6 (volume of Mg: volume of Ag = 10: 1) was deposited to a thickness of 100 by the same vapor deposition method.
Thus, the EL element 10 was obtained.
【００３１】（ＥＬ素子の評価）図２には、第１の正孔
輸送層３がo-PTDATA又はp-PMTDATAからなる２つのＥＬ
素子１０についての発光強度スペクトルを示した。どち
らの場合においても、発光層５のAlq3に起因した緑色の
発光が確認された。なお、発光強度スペクトルは、日立
製のＦ−４５００分光蛍光光度計を用い、室温、大気中
において、前記ＥＬ素子に８Ｖの電圧を印加することに
より実施した。(Evaluation of EL Element) FIG. 2 shows that the first hole transport layer 3 is composed of two ELs made of o-PTDATA or p-PMTDATA.
The emission intensity spectrum of the device 10 is shown. In both cases, green light emission due to Alq 3 in the light emitting layer 5 was confirmed. The emission intensity spectrum was measured using a Hitachi F-4500 spectrofluorometer at room temperature and in the air by applying a voltage of 8 V to the EL element.
【００３２】図３には、第１の正孔輸送層３がo-PTDATA
又はp-PMTDATAからなる２つのＥＬ素子１０について、
ＩＴＯ透明電極２及びＭｇＡｇ電極６にＩＴＯ電極側を
正とする電極を印加することによって測定した、発光輝
度及び電流密度のグラフを示す。図３から明らかなよう
に、印加電圧約３Ｖから発光が生じ始め、約１４Ｖの印
加電圧で、第１の正孔輸送層３にo-PTDATA又はp-PMTDAT
Aを用いてなるそれぞれのＥＬ素子１０について、約１
７０００ｃｄ／ｍ２の発光輝度が得られた。また、発光
輝度約３００ｃｄ／ｍ２における電流密度は１０ｍＡ／
ｃｍ２であり、１．２ｌｍ／Ｗの発光効率が得られるこ
とが判明した。すなわち、正孔輸送層に、本発明にした
がってo-PTDATA又はp-PMTDATAを用いてなるＥＬ素子１
０は高い発光輝度と発光効率とを有することが分かる。
なお、発光輝度及び電流密度は、アドバンテスト製のＴ
Ｒ−６１４３直流電源／電流源／モニタからなる発光輝
度測定装置、並びにミノルタ製ＬＳ−１００の輝度計を
用いて測定した。FIG. 3 shows that the first hole transport layer 3 is made of o-PTDATA.
Or about two EL elements 10 composed of p-PMTDATA,
4 is a graph of emission luminance and current density measured by applying an electrode with the ITO electrode side being positive to the ITO transparent electrode 2 and the MgAg electrode 6. As is apparent from FIG. 3, light emission starts to occur from an applied voltage of about 3 V, and o-PTDATA or p-PMTDAT is applied to the first hole transport layer 3 at an applied voltage of about 14 V.
For each EL element 10 using A, about 1
An emission luminance of 7000 cd / m 2 was obtained. The current density at an emission luminance of about 300 cd / m 2 is 10 mA /
cm 2 and a luminous efficiency of 1.2 lm / W was obtained. That is, the EL element 1 using o-PTDATA or p-PMTDATA in the hole transport layer according to the present invention.
It can be seen that 0 has high light emission luminance and light emission efficiency.
The light emission luminance and current density were measured by Advantest T
The measurement was performed using a light emission luminance measuring device composed of R-6143 DC power supply / current source / monitor, and a luminance meter LS-100 manufactured by Minolta.
【００３３】図４は、上記ＥＬ素子を室温から温度を上
昇させた場合の発光輝度の変化を示したものである。室
温において約３００ｃｄ／ｍ２の発光輝度を有するＥＬ
素子は、温度上昇とともにその発光輝度を若干減じるも
のの、約１５０℃においても約２３０ｃｄ／ｍ２の発光
輝度を有している。すなわち、本発明にしたがって得た
ＥＬ素子１０は、高い発光輝度及び発光効率に加えて、
高い耐熱性と耐久性とを具えることが判明した。なお、
発光輝度の温度変化は、温度センサー及びヒータを具え
たクライオスタット（Oxford ITC-502）中、０．１ｔｏ
ｒｒの真空中で実施した。FIG. 4 shows a change in light emission luminance when the temperature of the EL element is increased from room temperature. EL having an emission luminance of about 300 cd / m 2 at room temperature
The device has a light emission luminance of about 230 cd / m 2 even at about 150 ° C., although the light emission luminance slightly decreases with an increase in temperature. That is, the EL element 10 obtained according to the present invention has high emission luminance and emission efficiency,
It has been found that it has high heat resistance and durability. In addition,
The temperature change of the light emission brightness was 0.1 ton in a cryostat (Oxford ITC-502) equipped with a temperature sensor and a heater.
Performed in rr vacuum.
【００３４】以上、具体例を挙げながら発明の実施の形
態に基づいて本発明を詳細に説明してきたが、本発明は
上記内容に限定されるものではなく、本発明の範疇を逸
脱しない限りにおいて、あらゆる変形や変更が可能であ
る。As described above, the present invention has been described in detail based on the embodiments of the present invention with reference to specific examples. However, the present invention is not limited to the above contents, and the present invention is not limited thereto. All modifications and changes are possible.
【００３５】[0035]
【発明の効果】本発明によれば、発光輝度及び発光効率
に優れたＥＬ素子を得ることができる。また、正孔輸送
層に使用する有機化合物材料に起因して高い耐熱性と高
い耐久性とを具えるため、本ＥＬ素子を、例えばフルカ
ラーのフラットパネルディスプレイに用いた場合におい
ても、発光輝度及び発光効率が低下することがない。し
たがって、各種デバイスにおける発光素子として十分使
用に耐え得ることができる。According to the present invention, it is possible to obtain an EL device excellent in light emission luminance and light emission efficiency. In addition, in order to provide high heat resistance and high durability due to the organic compound material used for the hole transport layer, even when the present EL element is used for, for example, a full-color flat panel display, light emission luminance and Luminous efficiency does not decrease. Therefore, it can be sufficiently used as a light emitting element in various devices.
【図１】 本発明のＥＬ素子構成の一例を示す概略図で
ある。FIG. 1 is a schematic view showing an example of an EL element configuration according to the present invention.
【図２】 本発明のＥＬ素子の発光スペクトルの一例を
示すグラフである。FIG. 2 is a graph showing an example of an emission spectrum of the EL device of the present invention.
【図３】 本発明のＥＬ素子の発光輝度及び電圧−電流
密度特性の一例を示すグラフである。FIG. 3 is a graph showing an example of emission luminance and voltage-current density characteristics of the EL element of the present invention.
【図４】 本発明のＥＬ素子における発光輝度の温度特
性の一例を示すグラフである。FIG. 4 is a graph showing an example of a temperature characteristic of light emission luminance in the EL element of the present invention.
１ ガラス基板 ２ ＩＴＯ電極 ３ 第１の正孔輸送層 ４ 第２の正孔輸送層 ５ 発光層 ６ ＭｇＡｇ電極 １０ ＥＬ素子 Reference Signs List 1 glass substrate 2 ITO electrode 3 first hole transport layer 4 second hole transport layer 5 light emitting layer 6 MgAg electrode 10 EL element
Claims (11)
光層と、背面電極とを具え、これらがこの順に積層され
てなるエレクトロルミネッセンス素子であって、 前記正孔輸送層の少なくとも一部が、4、4'、4''-トリ
ス［ビフェニル-2-イル（フェニル）アミノ］トリフェ
ニルアミン及び4、4'、4''-トリス［ビフェニル-4-イル
（3-メチルフェニル）アミノ］トリフェニルアミンなる
有機化合物材料の少なくとも一方から構成されているこ
とを特徴とする、エレクトロルミネッセンス素子。1. An electroluminescent device comprising a substrate, a transparent electrode, a hole transport layer, a light emitting layer, and a back electrode, which are laminated in this order, wherein at least one of the hole transport layer Some are 4,4 ′, 4 ″ -tris [biphenyl-2-yl (phenyl) amino] triphenylamine and 4,4 ′, 4 ″ -tris [biphenyl-4-yl (3-methylphenyl 2.) An electroluminescent device, comprising at least one of organic compound materials of [amino] triphenylamine.
第２の正孔輸送層からなり、前記第１の正孔輸送層は、
4、4'、4''-トリス［ビフェニル-2-イル（フェニル）ア
ミノ］トリフェニルアミン及び4、4'、4''-トリス［ビ
フェニル-4-イル（3-メチルフェニル）アミノ］トリフ
ェニルアミンなる有機化合物材料の少なくとも一方から
構成されるとともに、前記第２の正孔輸送層は、N、N'-
ジ（ビフェニル-4-イル）-N、N'-ジフェニル-［1，1'-
ビフェニル］-4，4'-ジアミンなる有機化合物材料から
なることを特徴とする、請求項１に記載のエレクトロル
ミネッセンス素子。2. The hole transport layer comprises a first hole transport layer and a second hole transport layer, wherein the first hole transport layer comprises:
4,4 ′, 4 ″ -tris [biphenyl-2-yl (phenyl) amino] triphenylamine and 4,4 ′, 4 ″ -tris [biphenyl-4-yl (3-methylphenyl) amino] triphenylamine The second hole transport layer is composed of at least one of an organic compound material of phenylamine,
Di (biphenyl-4-yl) -N, N'-diphenyl- [1,1'-
2. The electroluminescent device according to claim 1, comprising an organic compound material of [biphenyl] -4,4'-diamine.
孔輸送層は、前記基板の上方においてこの順に積層され
てなることを特徴とする、請求項２に記載のエレクトロ
ルミネッセンス素子。3. The electroluminescent device according to claim 2, wherein the first hole transport layer and the second hole transport layer are stacked in this order above the substrate. .
〜５００Åであり、前記第２の正孔輸送層の厚さが、１
００〜５００Åであることを特徴とする、請求項３に記
載のエレクトロルミネッセンス素子。4. The method according to claim 1, wherein the thickness of the first hole transport layer is 100
Å500 °, and the thickness of the second hole transport layer is 1
4. The electroluminescent device according to claim 3, wherein the angle is from 00 to 500 [deg.].
ト）アルミニウムなる有機化合物材料からなることを特
徴とする、請求項１〜４のいずれか一に記載のエレクト
ロルミネッセンス素子。5. The electroluminescent device according to claim 1, wherein the light emitting layer is made of an organic compound material of tris (8-quinolinolato) aluminum.
Åであることを特徴とする、請求項５に記載のエレクト
ロルミネッセンス素子。6. The light emitting layer has a thickness of 200 to 1000.
The electroluminescent device according to claim 5, wherein?
（フェニル）アミノ］トリフェニルアミンなる有機化合
物。7. An organic compound comprising 4,4 ′, 4 ″ -tris [biphenyl-2-yl (phenyl) amino] triphenylamine.
（3-メチルフェニル）アミノ］トリフェニルアミンなる
有機化合物。8. An organic compound comprising 4,4 ′, 4 ″ -tris [biphenyl-4-yl (3-methylphenyl) amino] triphenylamine.
（フェニル）アミノ］トリフェニルアミンなるエレクト
ロルミネッセンス素子の正孔輸送層用有機化合物材料。9. An organic compound material for a hole transport layer of an electroluminescence device, which is 4,4 ′, 4 ″ -tris [biphenyl-2-yl (phenyl) amino] triphenylamine.
ル（3-メチルフェニル）アミノ］トリフェニルアミンな
るエレクトロルミネッセンス素子の正孔輸送層用有機化
合物材料。10. An organic compound material for a hole transport layer of an electroluminescence device, which is 4,4 ′, 4 ″ -tris [biphenyl-4-yl (3-methylphenyl) amino] triphenylamine.
N'-ジフェニル-［1，1'-ビフェニル］-4，4'-ジアミン
なるエレクトロルミネッセンス素子の正孔輸送層用有機
化合物材料。11. N, N′-di (biphenyl-4-yl) -N,
N'-diphenyl- [1,1'-biphenyl] -4,4'-diamine An organic compound material for a hole transport layer of an electroluminescent device.
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|---|---|---|---|
| JP36278499A JP3735703B2 (en) | 1999-12-21 | 1999-12-21 | Electroluminescence element |
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1999
- 1999-12-21 JP JP36278499A patent/JP3735703B2/en not_active Expired - Lifetime
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