JPH0288689A - Luminescent element of electric field - Google Patents

Luminescent element of electric field

Info

Publication number
JPH0288689A
JPH0288689A JP63240183A JP24018388A JPH0288689A JP H0288689 A JPH0288689 A JP H0288689A JP 63240183 A JP63240183 A JP 63240183A JP 24018388 A JP24018388 A JP 24018388A JP H0288689 A JPH0288689 A JP H0288689A
Authority
JP
Japan
Prior art keywords
layer
emitting layer
transport layer
organic dye
light emitting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP63240183A
Other languages
Japanese (ja)
Inventor
Shogo Saito
省吾 斎藤
Tetsuo Tsutsui
哲夫 筒井
Seiji Tokitou
静士 時任
Chibao Adachi
安達 千波夫
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Kasei Corp
Original Assignee
Mitsubishi Kasei Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp
Priority to JP63240183A priority Critical patent/JPH0288689A/en
Publication of JPH0288689A publication Critical patent/JPH0288689A/en
Pending legal-status Critical Current

Links

Abstract

PURPOSE:To obtain a luminescent element of electric field applicable to various kinds of display fields, providing high luminance emission even at low drive voltage, having a luminous layer consisting of a specific yellow organic pigment of perionone type. CONSTITUTION:In a luminescent element of electric field wherein a luminous layer sandwiched in between a hole transportation layer and a luminous layer or the hole transportation layer and an electron transportation layer is set between electrodes made of an electroconductive layer, the luminous layer consists of a yellow organic pigment of perinone type to give the aimed element. The thickness of the luminous layer is usually 500-3,000Angstrom (preferably 700-2,000Angstrom ).

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は電界発光素子に関するものであり、詳しくは、
発光層として有機色素を利用した電界発光素子に関する
ものである。
[Detailed Description of the Invention] (Industrial Application Field) The present invention relates to an electroluminescent device, and in detail,
The present invention relates to an electroluminescent device using an organic dye as a light emitting layer.

(先行技術) 従来、電界発光素子としては、発光層に例えば、硫化セ
レンや硫化亜鉛などの無機系蛍光体を用いたものが一般
的である。しかし、近年、発光層として、有機色素を利
用し発光させる方法が提案された。(特開昭59−19
4393号参照)すなわち、この方法では、電極間にホ
ール輸送層(正孔インジェクション帯域)と有機色素よ
りなる発光層を設け、これに電圧を印加し発光層を発光
させるものである。
(Prior Art) Conventionally, electroluminescent devices have generally used an inorganic fluorescent material such as selenium sulfide or zinc sulfide in a light emitting layer. However, in recent years, a method of emitting light using an organic dye as a light-emitting layer has been proposed. (Unexamined Japanese Patent Publication No. 59-19
4393) That is, in this method, a hole transport layer (hole injection zone) and a light emitting layer made of an organic dye are provided between electrodes, and a voltage is applied thereto to cause the light emitting layer to emit light.

ところが、この方法で開示されている有機色素を発光層
として用いた場合には、まだ発光の程度が不十分であり
、更に改良検討が望まれていた。
However, when the organic dye disclosed in this method is used as a light-emitting layer, the level of light emission is still insufficient, and further improvement studies have been desired.

(発明の目的と解決手段) 本発明者等は上記実情に鑑み、有機色素を発光層に利用
した電界発光素子において、低電圧でも高輝度に発光し
得る有機色素を提供することを目的として鋭意検討した
結果、ある特定の黄色系のペリノン型有機色素が好まし
い発光を示すことを見出し、本発明を完成した。
(Objects of the Invention and Means for Solving the Invention) In view of the above circumstances, the present inventors have made efforts to provide an organic dye that can emit light with high brightness even at a low voltage in an electroluminescent device using an organic dye in a light emitting layer. As a result of investigation, it was discovered that a certain yellow perinone-type organic dye exhibits preferable luminescence, and the present invention was completed.

すなわち、本発明の要旨は、導電層よりなる電極間に、
ホール輸送層と有機色素よりなる発光層、又は、ホール
輸送層と電子輸送層とに挾まれた有機色素よりなる発光
層が設けられた電界発光素子において、発光層が下記一
般式〔l〕で示される黄色系の有機色素で構成されてい
ることを特徴とする電界発光素子に存する。
That is, the gist of the present invention is that between the electrodes made of a conductive layer,
In an electroluminescent element provided with a light emitting layer made of a hole transport layer and an organic dye, or a light emitting layer made of an organic dye sandwiched between a hole transport layer and an electron transport layer, the light emitting layer is represented by the following general formula [l]. The present invention relates to an electroluminescent device characterized in that it is composed of the yellowish organic dye shown below.

(式中、Rはアルキル基又はフェニル基を表す)以下、
本発明の電界発光素子について添付図面に従い説明する
。第1図及び第2図は一例の本発明の電界発光素子の構
造を模式的に示す断面図であり、1は基板、2a、2b
は導電層、3はホール輸送層、4は発光層、5は電子輸
送層を表す。
(In the formula, R represents an alkyl group or a phenyl group) Below,
The electroluminescent device of the present invention will be explained with reference to the accompanying drawings. 1 and 2 are cross-sectional views schematically showing the structure of an electroluminescent device of the present invention as an example, in which 1 is a substrate, 2a, 2b
3 represents a conductive layer, 3 represents a hole transport layer, 4 represents a light emitting layer, and 5 represents an electron transport layer.

基板1は通常、ガラス板又はポリエステル、ポリカーボ
ネート、ポリサルホンなどの透明な合成樹脂フィルムで
構成されている。基板1上には導電層2aが設けられる
が、この導電層2aとしては通常、金、パラジウム、イ
ンジウム及び/又はスズなどの金属あるいは酸化物によ
り構成される。導電層2aの厚みは通常、100〜30
0人程度である。導電層の形成は常法に従って例えば、
スパッタリング法、真空蒸着法などの方法により行うこ
とができる。なお、この導電層2aは例えば、陽極とし
ての役割を果たすものである。また、この導電層は通常
、透明なものが望ましい。
The substrate 1 is usually made of a glass plate or a transparent synthetic resin film made of polyester, polycarbonate, polysulfone, or the like. A conductive layer 2a is provided on the substrate 1, and this conductive layer 2a is usually made of a metal or oxide such as gold, palladium, indium and/or tin. The thickness of the conductive layer 2a is usually 100 to 30
Approximately 0 people. The conductive layer is formed according to a conventional method, for example,
This can be carried out by a method such as a sputtering method or a vacuum evaporation method. Note that this conductive layer 2a serves, for example, as an anode. Further, it is usually desirable that this conductive layer be transparent.

導電層2aの上にはボール輸送層3が設けられるが、ホ
ール輸送層3としては、電場を与えられた電極間におい
て陽極からの正孔を適切に陰極へ伝達することができる
化合物により形成される。このような正孔伝達化合物は
例えば、特開昭59−194393号の第5〜6頁及び
米国特許第4175960号の第13〜14欄に解説さ
れるものなどが挙げられる。これら化合物の好ましい具
体例としては、N、N’−ジフェニル−N、N’ −(
3−メチルフェニル)−1,1°−ビフェニル−4,4
゛−ジアミン:1.1”−ビス(4−ジ−p−トリルア
ミノフェニル)シクロヘキサン=4.4°°−ビス(ジ
フェニルアミノ)クワトリフェニルなどの芳香族アミン
系化合物が挙げられる。ホール輸送層3は通常、真空蒸
着法により形成されるので、正孔伝達化合物の選定は膜
形成性の面からも考慮する必要がある。ホール輸送層3
の厚さは通常、500〜3000人、好ましくは100
0〜2000人で菖る。なお、ホール輸送層は陽極を形
成する導電層上に設ける必要がありもし、陽極と陰極が
逆の場合には、その形成層も反対側となる。
A ball transport layer 3 is provided on the conductive layer 2a, and the hole transport layer 3 is formed of a compound that can appropriately transmit holes from the anode to the cathode between the electrodes to which an electric field is applied. Ru. Examples of such hole transfer compounds include those described in pages 5-6 of Japanese Patent Application Laid-open No. 59-194393 and columns 13-14 of US Pat. No. 4,175,960. Preferred specific examples of these compounds include N,N'-diphenyl-N,N'-(
3-methylphenyl)-1,1°-biphenyl-4,4
-Diamine: Examples include aromatic amine compounds such as 1.1''-bis(4-di-p-tolylaminophenyl)cyclohexane = 4.4°°-bis(diphenylamino)quatriphenyl. Hole transport Since the layer 3 is usually formed by a vacuum evaporation method, the selection of the hole transport compound must also be considered from the aspect of film formation.Hole transport layer 3
The thickness is usually 500 to 3000, preferably 100
0 to 2,000 people will participate. Note that the hole transport layer needs to be provided on the conductive layer forming the anode, and if the anode and cathode are reversed, the layer forming the layer will also be on the opposite side.

本発明の電界発光素子は導電層2a、2bよりなる電極
間に、上述のホール輸送層3と発光層4を有するが、第
1図に示すように、発光層4の一方がホール輸送層3で
あり、しかも、他方に電子輸送層5を有する構造、また
、第2図に示すように、発光層4の一方がホール輸送層
3であるものの、他方は直接、導電層2bと接する構造
の二つのタイプのものがある。しかし、発光の効率面か
らは三層構造となった前者のタイプが特に望ましい。な
お、この場合、本発明の効果を阻害しなければ、その他
の層を更に設けても差し支えない。
The electroluminescent device of the present invention has the above-described hole transport layer 3 and light emitting layer 4 between the electrodes consisting of conductive layers 2a and 2b, and as shown in FIG. Moreover, as shown in FIG. 2, one of the light-emitting layers 4 is the hole-transporting layer 3, and the other is in direct contact with the conductive layer 2b. There are two types. However, from the viewpoint of light emission efficiency, the former type having a three-layer structure is particularly desirable. In this case, other layers may be provided as long as the effects of the present invention are not impaired.

第1図のように、発光層4の反対面に設けられる電子輸
送層5は電子を効果的に発光層4に送るための化合物に
より形成され、陰極となる導電層2bと接して設けられ
る。電子輸送層を形成する化合物としては上記の如き効
果を有する化合物であれば特に限定されず、例えば、下
記構造式で示されるようなペリレン化合物が代表的に挙
げられる。
As shown in FIG. 1, the electron transport layer 5 provided on the opposite side of the light-emitting layer 4 is formed of a compound for effectively transporting electrons to the light-emitting layer 4, and is provided in contact with the conductive layer 2b serving as a cathode. The compound forming the electron transport layer is not particularly limited as long as it has the above-mentioned effects, and representative examples thereof include perylene compounds as shown by the following structural formula.

電子輸送層5の厚さは通常、1000〜2000人程度
である。電子輸送層5も通常の真空蒸着法により形成さ
せることができる。
The thickness of the electron transport layer 5 is usually about 1,000 to 2,000 layers. The electron transport layer 5 can also be formed by a normal vacuum deposition method.

一方、導電層2bは陰極となるが、この導電層は透明で
ある必要は必すしもなく、例えば、マグネシウム、アル
ミニウム、銀などの適当な金属により構成することがで
きる。
On the other hand, the conductive layer 2b serves as a cathode, but this conductive layer does not necessarily have to be transparent and can be made of a suitable metal such as magnesium, aluminum, or silver.

本発明においては、上述のような電界発光素子における
発光層4として、前示一般式〔1〕で示される黄色系の
ペリノン型有機色素を用いることを必須の要件とする。
In the present invention, it is essential to use a yellow perinone type organic dye represented by the general formula [1] as the light emitting layer 4 in the electroluminescent device as described above.

すなわち、この有機色素を用いる場合には、低い駆動電
圧で高輝度の発光が得られるのである。また、発光層の
形成に際しても、真空蒸着により均質の膜形成ができる
That is, when this organic dye is used, high-intensity light emission can be obtained with a low driving voltage. Furthermore, when forming the light-emitting layer, a homogeneous film can be formed by vacuum deposition.

前示一般式中、Rで表されるアルキル基としては例えば
、メチル基、エチル基、直鎖あるいは分岐のプロピル基
、ブチル基、ヘキシル基、オクチル基などの炭素数1〜
8、好ましくは1〜4のアルキル基が挙げられる。また
、フェニれたものでもよい。発光層4の厚さは通常、5
00〜3000人、好ましくは700〜2000人であ
る。
In the above general formula, the alkyl group represented by R is, for example, a methyl group, an ethyl group, a linear or branched propyl group, a butyl group, a hexyl group, an octyl group, etc. having 1 to 1 carbon atoms.
8, preferably 1 to 4 alkyl groups. Also, it may be a feminized one. The thickness of the light emitting layer 4 is usually 5
00 to 3000 people, preferably 700 to 2000 people.

(発明の効果) 本発明の電界発光素子によれば、導電層/ホール輸送層
/発光層/(電子輸送層)/導電層が基板上に順次、設
けられ、しかも、発光層に特定の有機色素を採用してい
るため、再沸電層を電極とし電圧を印加した場合、低い
駆動電圧で高輝度の発光を得ることができる。従って、
本発明の電界発光素子は各種デイスプレィ分野への応用
が考えられ、その技術的価値は大きいものである。
(Effects of the Invention) According to the electroluminescent device of the present invention, the conductive layer/hole transport layer/emissive layer/(electron transport layer)/conductive layer are sequentially provided on the substrate, and the emissive layer contains a specific organic material. Since a dye is used, when a voltage is applied using the reboiling layer as an electrode, high-brightness light emission can be obtained with a low driving voltage. Therefore,
The electroluminescent device of the present invention can be applied to various display fields and has great technical value.

(実施例) 次に、本発明を実施例によって更に具体的に説明するが
、本発明はその要旨を超えない限り、以下の実施例の記
載に限定されるものではない。
(Examples) Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the description of the following Examples unless it exceeds the gist thereof.

実施例I 第1図に示す構造の電界発光素子を製造した。Example I An electroluminescent device having the structure shown in FIG. 1 was manufactured.

ガラス基板上に、先ず、下表に示す条件で真空蒸着によ
って、厚さ 約120人の金層(導電層)を形成し、そ
の上に、N、N″−ジフェニル−N、N”−(3−メチ
ルフェニル)−11−ビフェニル−4,4″−ジアミン
の膜(ホール輸送層)を約2000人の厚さで形成し、
次いで、下記構造式 〔真空蒸着の条件〕 で示されるペリノン化合物の膜(発光層)を約1000
人の厚さで形成し、更に、その上に、下記構造式 で示される化合物の膜(電子輸送N)を約1000人の
厚さで形成させた後、最後に厚さ約500人のマグネシ
ウム層(導電層)を順次、真空蒸着法によって形成した
First, a gold layer (conductive layer) with a thickness of about 120 nm was formed on a glass substrate by vacuum evaporation under the conditions shown in the table below, and on top of that, N,N''-diphenyl-N,N''-( A film (hole transport layer) of 3-methylphenyl)-11-biphenyl-4,4″-diamine is formed to a thickness of about 2000 μm,
Next, a film (emitting layer) of a perinone compound represented by the following structural formula [vacuum deposition conditions]
On top of that, a film of a compound represented by the following structural formula (electron transport N) is formed to a thickness of about 1,000 people, and finally a magnesium film is formed to a thickness of about 500 people. The layers (conductive layers) were sequentially formed by vacuum evaporation.

このようにして第1図に示すような構造を有する電界発
光素子を製作し、この素子のAu層をプラス、Mg層を
マイナスとし、60Vの電圧を印加したところ、IPW
/cI11の黄色の発光が確認された。その際の外部量
子効率を求めたところ、0.04%phoむon/ e
lectronであった。
In this way, an electroluminescent device having the structure shown in FIG.
/cI11 yellow luminescence was confirmed. When we calculated the external quantum efficiency at that time, it was 0.04%phomuon/e
It was an electron.

比較例1 実施例1において、発光層として下記構造式で示される
ペリレン化合物を用い、その他は実施例1と同様にして
電界発光素子を製作した。
Comparative Example 1 In Example 1, an electroluminescent device was manufactured in the same manner as in Example 1 except that a perylene compound represented by the following structural formula was used as the light emitting layer.

この素子について実施例1と同様に電圧を印加したとこ
ろ、発光量は0 、 1 HW / cliであり、そ
の際の外部量子効率は0.004%photon/ e
lectronであった。
When a voltage was applied to this device in the same manner as in Example 1, the amount of light emission was 0.1 HW/cli, and the external quantum efficiency at that time was 0.004% photon/e.
It was an electron.

実施例2 実施例1において、発光層として前示一般式(1)にお
けるRがエチル基、n−ブチル基、n−オクチル基、2
−エチル−ヘキシル基、フェニル基又はP−メトキシ−
フェニル基である各々の本発明の有機色素を用いた場合
にも、これら電界発光素子は良好な発光を示す。
Example 2 In Example 1, as a light emitting layer, R in the general formula (1) shown above is an ethyl group, an n-butyl group, an n-octyl group, or 2
-ethyl-hexyl group, phenyl group or P-methoxy-
Even when each of the organic dyes of the present invention having a phenyl group is used, these electroluminescent devices exhibit good luminescence.

【図面の簡単な説明】[Brief explanation of drawings]

第1図及び第2図は本発明の電界発光素子の一例を模式
的に示す断面図であり、1は基板、2a、2bは導電層
、3はボール輸送層、4ば発光層、5は電子輸送層を示
す。
1 and 2 are cross-sectional views schematically showing an example of the electroluminescent device of the present invention, in which 1 is a substrate, 2a and 2b are conductive layers, 3 is a ball transport layer, 4 is a light emitting layer, and 5 is a Shows an electron transport layer.

Claims (1)

【特許請求の範囲】[Claims]  (1)導電層よりなる電極間に、ホール輸送層と有機
色素よりなる発光層、又は、ホール輪送層と電子輸送層
とに挟まれた有機色素よりなる発光層が設けられた電界
発光素子において、発光層が下記一般式〔1〕で示され
る黄色系の有機色素で構成されていることを特徴とする
電界発光素子。 ▲数式、化学式、表等があります▼ (式中、Rはアルキル基又はフェニル基を表す)
(1) An electroluminescent device in which a light emitting layer made of a hole transport layer and an organic dye is provided between electrodes made of a conductive layer, or a light emitting layer made of an organic dye sandwiched between a hole transport layer and an electron transport layer. An electroluminescent device characterized in that the light-emitting layer is composed of a yellowish organic dye represented by the following general formula [1]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R represents an alkyl group or a phenyl group)
JP63240183A 1988-09-26 1988-09-26 Luminescent element of electric field Pending JPH0288689A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP63240183A JPH0288689A (en) 1988-09-26 1988-09-26 Luminescent element of electric field

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP63240183A JPH0288689A (en) 1988-09-26 1988-09-26 Luminescent element of electric field

Publications (1)

Publication Number Publication Date
JPH0288689A true JPH0288689A (en) 1990-03-28

Family

ID=17055703

Family Applications (1)

Application Number Title Priority Date Filing Date
JP63240183A Pending JPH0288689A (en) 1988-09-26 1988-09-26 Luminescent element of electric field

Country Status (1)

Country Link
JP (1) JPH0288689A (en)

Cited By (29)

* Cited by examiner, † Cited by third party
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JPH04212287A (en) * 1990-05-29 1992-08-03 Toppan Printing Co Ltd Organic membranous electro-luminescence(el) element
JPH04212284A (en) * 1990-04-27 1992-08-03 Toppan Printing Co Ltd Organic membranous electro-luminescence(el) element
US6013384A (en) * 1997-01-27 2000-01-11 Junji Kido Organic electroluminescent devices
US6396209B1 (en) 1998-12-16 2002-05-28 International Manufacturing And Engineering Services Co., Ltd. Organic electroluminescent device
US6423429B2 (en) 1998-03-02 2002-07-23 Junji Kido Organic electroluminescent devices
US6459199B1 (en) 1996-05-15 2002-10-01 Chemipro Kasei Kaisha, Limited Multicolor organic EL element having plurality of organic dyes, method of manufacturing the same, and display using the same
US6589673B1 (en) 1999-09-29 2003-07-08 Junji Kido Organic electroluminescent device, group of organic electroluminescent devices
US7326473B2 (en) 1998-02-17 2008-02-05 Junji Kido Organic electroluminescent devices
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