JPH0455493A - Organic thin film el element - Google Patents

Organic thin film el element

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Publication number
JPH0455493A
JPH0455493A JP2164412A JP16441290A JPH0455493A JP H0455493 A JPH0455493 A JP H0455493A JP 2164412 A JP2164412 A JP 2164412A JP 16441290 A JP16441290 A JP 16441290A JP H0455493 A JPH0455493 A JP H0455493A
Authority
JP
Japan
Prior art keywords
thin film
organic
ester
dicarboxylic acid
organic light
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
JP2164412A
Other languages
Japanese (ja)
Inventor
Koji Utsuki
功二 宇津木
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.)
NEC Corp
Original Assignee
NEC 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 NEC Corp filed Critical NEC Corp
Priority to JP2164412A priority Critical patent/JPH0455493A/en
Publication of JPH0455493A publication Critical patent/JPH0455493A/en
Pending legal-status Critical Current

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  • Electroluminescent Light Sources (AREA)
  • Luminescent Compositions (AREA)

Abstract

PURPOSE:To obtain the subject element usable as a flat light source or a display capable of obtaining by only changing concentration of an organic luminescent material using a specific 3,9-perylene dicarboxylic acid ester as the organic luminescent material. CONSTITUTION:The objective element contains 3,9-perylene dicarboxylic acid ester expressed by the formula (R is alkyl, alkoxy, phenyl or substituted phenyl) as an organic luminescent material. As an example of said ester, diphenyl ester, dimethyl ester, diethyl ester, di(p-dimethyoxyphenyl) ester, di(p-diethoxyphenyl) ester, di(p-diaminophenyl) ester, di(p-dimethylaminophenyl) ester or di(p- diethylaminophenyl) ester, etc., of 3,9-perylene dicarboxylic acid, is exemplified.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は平面光源やデイスプレィに使用される有機薄膜
EL素子に関するものである。
DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to an organic thin film EL element used for flat light sources and displays.

(従来の技術) 有機の蛍光物質を有機発光体薄膜層としたEL(電界発
光)素子は、安価な大面積フルカラー表示素子を実現す
るものとして注目を集めている。雑誌「化学と工業」4
2巻、2023ページ、1989年には、強い蛍光を発
する有機色素を有機発光体薄膜層に使用し、青、緑、赤
色の明るい発光のEL素子が報告されている。この素子
では薄膜状で強い蛍光を発し、ピンホール欠陥の少ない
有機色素を用いたことで、高輝度なマルチカラー発光を
実現できたと考えられている。
(Prior Art) An EL (electroluminescent) device using an organic fluorescent material as an organic light-emitting thin film layer is attracting attention as a device for realizing an inexpensive large-area full-color display device. Magazine “Chemistry and Industry” 4
Vol. 2, p. 2023, 1989 reports an EL device that uses an organic dye that emits strong fluorescence in an organic light emitting thin film layer and emits bright blue, green, and red light. It is thought that this device was able to achieve high-brightness, multicolor light emission by using organic dyes that emit strong fluorescence in a thin film and have few pinhole defects.

(発明が解決しようとする課題) 前述の有機色素をもちいた有機薄膜EL素子は青、緑、
赤の発光を示す。しかし、一つの色素から得られる発光
色は一種類だけであり、高輝度なマルチカラー表示有機
薄膜EL素子実現のためにはまだ色素材料や素子構造を
十分検討しなければならない。
(Problem to be solved by the invention) The organic thin film EL device using the above-mentioned organic dye has blue, green,
Shows red luminescence. However, only one type of luminescent color can be obtained from one dye, and in order to realize a high-brightness multicolor display organic thin film EL device, sufficient consideration must be given to the dye material and device structure.

本発明は以上述べたような従来の事情に対処してなされ
たもので高輝度なマルチカラー発光の有機薄膜EL素子
を提供することを目的とする。
The present invention has been made in response to the above-mentioned conventional circumstances, and an object of the present invention is to provide an organic thin film EL device that emits high-luminance, multi-color light.

(課題を解決するための手段) 本発明は、少なくとも一方が透明な一対の電極間に、有
機電荷輸送性材料と有機発光材料の混合膜から成る有機
発光体薄膜層を少なくとも有する有機薄膜EL素子にお
いて有機発光材料が一般式(式中、Rはアルキル基、ア
ルコキシル基、フェニル基および置換フェニル基からな
る群から選ばれる。) で示される3、9−ペリレンジカルボン酸エステルであ
ることを特徴する有機薄膜EL素子である。
(Means for Solving the Problems) The present invention provides an organic thin film EL element having at least an organic light emitting thin film layer made of a mixed film of an organic charge transporting material and an organic light emitting material between a pair of electrodes, at least one of which is transparent. wherein the organic luminescent material is a 3,9-perylene dicarboxylic acid ester represented by the general formula (wherein R is selected from the group consisting of an alkyl group, an alkoxyl group, a phenyl group, and a substituted phenyl group). This is an organic thin film EL device.

このような構成をとることにより、濃度消光が防止され
、特性の優れた有機薄膜EL素子が得られる。また、有
機発光体薄膜層に含まれる3、9−ペリレンジカルボン
酸エステルの濃度によって発光色を緑から赤色まで変え
ることが可能である。
By adopting such a configuration, concentration quenching can be prevented and an organic thin film EL device with excellent characteristics can be obtained. Furthermore, the color of the emitted light can be changed from green to red depending on the concentration of 3,9-perylene dicarboxylic acid ester contained in the organic light emitting thin film layer.

本発明の有機薄膜EL素子としては、第1図のようにガ
ラス基板11上に透明電極12と背面電極15との間に
有機発光体薄膜層14のみが形成されたものの他、第2
図のように有機発光体薄膜層14と有機電子輸送性薄膜
層16が形成されたもの、第3図のように有機発光体薄
膜層14と有機正孔輸送性薄膜層13が形成されたもの
、および第4図のように有機発光体薄膜層14、有機電
子輸送性薄膜層16および有機正孔輸送性薄膜層13が
形成されたものが挙げられる。特に第2図から第4図に
示すように、有機発光体薄膜層と電極の間に有機電荷輸
送性薄膜を形成したものは、電極からの電荷注入効率を
高めることができ、更に有効である。
The organic thin film EL device of the present invention includes an organic light emitting thin film layer 14 formed on a glass substrate 11 between a transparent electrode 12 and a back electrode 15 as shown in FIG.
As shown in the figure, an organic light emitting thin film layer 14 and an organic electron transporting thin film layer 16 are formed, and as shown in FIG. 3, an organic light emitting thin film layer 14 and an organic hole transporting thin film layer 13 are formed. , and one in which an organic light emitting thin film layer 14, an organic electron transporting thin film layer 16, and an organic hole transporting thin film layer 13 are formed as shown in FIG. In particular, as shown in FIGS. 2 to 4, a structure in which an organic charge transporting thin film is formed between the organic light emitter thin film layer and the electrode is more effective because it can increase the efficiency of charge injection from the electrode. .

なお、透明電極として通常用いられるものはいずれでも
よく、例えばITO以外には5n02 :Sb、 Zn
O:A1やAuなどがあげられる。背面電極にはIn、
 Mg、 AgやMg : Agなどが使われる。
Note that any material commonly used as a transparent electrode may be used. For example, in addition to ITO, 5n02:Sb, Zn
O: Examples include A1 and Au. In the back electrode,
Mg, Ag, Mg:Ag, etc. are used.

本発明の有機発光材料として用いられる3、9−ペリレ
ンジカルボン酸エステルの具体的な例としては、3,9
−ペリレンジカルボン酸ジフェニルエステル、3,9−
ペリレンジカルボン酸ジメチルエステル、3.9−ペリ
レンジカルボン酸ジエチルエステル、3,9−ペリレン
ジカルボン酸−ジー(p−ジメトキシフェニル)エステ
ル、3,9−ペリレンジカルボン酸、ジー(0−ジメト
キシフェニル)エステル、3,9−ペリレンジカルボン
酸−ジー(p−ジェトキシフェニル)エステル、3,9
−ペリレンジカルボン酸−ジー(p−ジアミノフェニル
)エステル、3,9−ペリレンジカルボン酸−ジ−(1
)−ジメチルアミノフェニル)エステル、3,9−ペリ
レンジカルボン酸−ジー(p−ジエチルアミノフェニル
)エステルなどがあるがこの限りではない。
Specific examples of 3,9-perylene dicarboxylic acid esters used as the organic luminescent material of the present invention include 3,9-perylene dicarboxylic acid esters.
-Perylene dicarboxylic acid diphenyl ester, 3,9-
perylene dicarboxylic acid dimethyl ester, 3,9-perylene dicarboxylic acid diethyl ester, 3,9-perylene dicarboxylic acid di(p-dimethoxyphenyl) ester, 3,9-perylene dicarboxylic acid, di(0-dimethoxyphenyl) ester, 3,9-perylene dicarboxylic acid-di(p-jethoxyphenyl) ester, 3,9
-perylene dicarboxylic acid di-(p-diaminophenyl) ester, 3,9-perylene dicarboxylic acid di-(1
)-dimethylaminophenyl) ester, 3,9-perylene dicarboxylic acid di(p-diethylaminophenyl) ester, but are not limited to these.

これらの有機発光材料は、有機電荷輸送材料と混合して
用いられる。この有機電荷輸送材料としては、シクロヘ
キサン誘導体、オキサジアゾール誘導体、銅フタロシア
ニン誘導体、コバルトフタロシアニン誘導体、無金属フ
タロシアニン誘導体、ポリ−3−メチルチオフェン、ポ
リビニルカルバゾール誘導体などがある。
These organic light emitting materials are used in combination with organic charge transport materials. Examples of the organic charge transport material include cyclohexane derivatives, oxadiazole derivatives, copper phthalocyanine derivatives, cobalt phthalocyanine derivatives, metal-free phthalocyanine derivatives, poly-3-methylthiophene, and polyvinylcarbazole derivatives.

(実施例) 以下、本発明の実施例について詳細に説明する。(Example) Examples of the present invention will be described in detail below.

実施例1 有機発光体薄膜層の有機発光材料として3,9−ペリレ
ンジカルボン酸ジフェニルエステルを用い、さらに、そ
の層に含まれる有機電荷輸送性材料として1,1ビス(
4−N、N−ジトリルアミノフェニル)シクロヘキサン
を用いた。第1図に示すようにガラス基板11上にIT
O透明電極12を形成してから上記の有機発光材料が有
機発光体薄膜層中に0.1モル%含まれるように有機電
荷輸送性材料と1O−7Torrの真空中で共蒸着して
有機発光体薄膜層13を1oooλ形成した。最後に背
面金属電極14としてInを電子ビーム蒸着法で150
0人形成して有機薄膜EL素子を作成した。
Example 1 3,9-perylene dicarboxylic acid diphenyl ester was used as the organic light emitting material of the organic light emitting thin film layer, and 1,1 bis(
4-N,N-ditolylaminophenyl)cyclohexane was used. As shown in FIG.
After forming the O transparent electrode 12, the organic light emitting material is co-deposited with an organic charge transporting material in a vacuum of 1O-7 Torr so that the organic light emitting material is contained in the organic light emitting thin film layer at 0.1 mol% to produce organic light emission. A body thin film layer 13 having a thickness of 100λ was formed. Finally, as the back metal electrode 14, In is applied to 150% by electron beam evaporation method.
An organic thin film EL device was created by 0 people.

この素子の発光特性を乾燥窒素中で測定したところ、約
7■の直流電圧の印加で約100cd/m2の明るい黄
色発光が得られた。この有機薄膜EL素子を電流密度0
.5mA/am2の状態でエージング試験をしたところ
輝度半減時間は300時間以上であった。従来の素子で
は100から300時間であった。
When the luminescent properties of this device were measured in dry nitrogen, bright yellow luminescence of about 100 cd/m 2 was obtained by applying a DC voltage of about 7 μm. This organic thin film EL element has a current density of 0
.. When an aging test was conducted at 5 mA/am2, the luminance half-life was over 300 hours. In conventional devices, the time was 100 to 300 hours.

実施例2 有機発光体薄膜層の有機発光材料として3,9−ペリレ
ンジカルボン酸ジフェニ゛ルエステルを用い、さらに、
その層に含まれる有機電荷輸送性材料として1,1−ビ
ス(4−N、N−ジトリルアミノフェニル)シクロヘキ
サンを用いた。第1図に示すようにガラス基板11上に
ITO透明電極12を形成してから上記の有機発光材料
が有機発光体薄膜層中に10モル%含まれるように有機
電荷輸送性材料と1O−7Torrの真空中で共蒸着し
て有機発光体薄膜層13を1000人形成した。
Example 2 3,9-perylene dicarboxylic acid diphenyl ester was used as the organic luminescent material of the organic luminescent thin film layer, and further,
1,1-bis(4-N,N-ditolylaminophenyl)cyclohexane was used as the organic charge transporting material contained in the layer. As shown in FIG. 1, an ITO transparent electrode 12 is formed on a glass substrate 11, and then an organic charge-transporting material is mixed at 1O-7 Torr so that the above-mentioned organic luminescent material is contained in the organic luminescent thin film layer in an amount of 10 mol%. 1000 organic light emitting thin film layers 13 were formed by co-evaporation in a vacuum.

最後に背面金属電極14としてInを電子ビーム蒸着法
で1500人形成して有機薄膜EL素子を作成した。
Finally, 1,500 In was formed as the back metal electrode 14 by electron beam evaporation to produce an organic thin film EL device.

この素子の発光特性を乾燥窒素中で測定したところ、約
10Vの直流電圧の印加で約100cd/m2の明るい
赤色発光が得られた。
When the luminescent properties of this device were measured in dry nitrogen, bright red luminescence of about 100 cd/m2 was obtained when a DC voltage of about 10 V was applied.

実施例1,2かられかるように有機発光材料の濃度を変
えることにより発光色をかえることができる。同様にし
て、オレンジ、緑の発光を得ることができる。
As shown in Examples 1 and 2, the color of the emitted light can be changed by changing the concentration of the organic light emitting material. Similarly, orange and green luminescence can be obtained.

(発明の効果) 以上説明したように本発明の有機薄膜EL素子は、有機
発光材料の濃度を変えるだけで多種類の発光色を得るこ
とができ、マルチカラーの有機薄膜EL素子に有効であ
る。
(Effects of the Invention) As explained above, the organic thin film EL device of the present invention can obtain a wide variety of luminescent colors simply by changing the concentration of the organic light emitting material, and is effective for multicolor organic thin film EL devices. .

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

第1図は本発明の実施例に使用した有機薄膜EL素子の
断面構造を示す。第2図は有機発光体薄膜層と背面電極
の間に有機電子輸送性薄膜層を設けた2層構造の有機薄
膜EL素子の断面構造を示す。第3図は有機発光体薄膜
層と透明電極の間に有機正孔輸送性薄膜層を設けた2層
構造の有機薄膜EL素子の断面構造を示す。第4図は3
層構造の有機薄膜EL素子の断面構造を示す。 11・・・ガラス基板、12・・・透明電極、13・・
・有機正孔輸送性薄膜層、14・・・有機発光体薄膜層
、15・・・背面電極、16・・・有機電子輸送性薄膜
層。
FIG. 1 shows a cross-sectional structure of an organic thin film EL device used in an example of the present invention. FIG. 2 shows a cross-sectional structure of an organic thin film EL device having a two-layer structure in which an organic electron transporting thin film layer is provided between an organic light emitting thin film layer and a back electrode. FIG. 3 shows a cross-sectional structure of an organic thin film EL device having a two-layer structure in which an organic hole transporting thin film layer is provided between an organic light emitting thin film layer and a transparent electrode. Figure 4 is 3
1 shows a cross-sectional structure of an organic thin film EL device with a layered structure. 11...Glass substrate, 12...Transparent electrode, 13...
-Organic hole transporting thin film layer, 14...Organic light emitter thin film layer, 15...Back electrode, 16...Organic electron transporting thin film layer.

Claims (1)

【特許請求の範囲】[Claims] (1)少なくとも一方が透明な一対の電極間に、有機電
荷輸送性材料と有機発光材料の混合膜から成る有機発光
体薄膜層を少なくとも有する有機薄膜EL素子において
有機発光材料が一般式 ▲数式、化学式、表等があります▼ (式中、Rはアルキル基、アルコキシル基、フェニル基
および置換フェニル基からなる群から選ばれる。) で示される3,9−ペリレンジカルボン酸エステルであ
ることを特徴する有機薄膜EL素子。
(1) In an organic thin-film EL element having at least an organic light-emitting thin film layer consisting of a mixed film of an organic charge transporting material and an organic light-emitting material between a pair of electrodes, at least one of which is transparent, the organic light-emitting material is expressed by the general formula ▲Math. There are chemical formulas, tables, etc. ▼ (In the formula, R is selected from the group consisting of an alkyl group, an alkoxyl group, a phenyl group, and a substituted phenyl group.) Characterized by being a 3,9-perylene dicarboxylic acid ester represented by Organic thin film EL device.
JP2164412A 1990-06-22 1990-06-22 Organic thin film el element Pending JPH0455493A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2164412A JPH0455493A (en) 1990-06-22 1990-06-22 Organic thin film el element

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2164412A JPH0455493A (en) 1990-06-22 1990-06-22 Organic thin film el element

Publications (1)

Publication Number Publication Date
JPH0455493A true JPH0455493A (en) 1992-02-24

Family

ID=15792653

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2164412A Pending JPH0455493A (en) 1990-06-22 1990-06-22 Organic thin film el element

Country Status (1)

Country Link
JP (1) JPH0455493A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0965629A1 (en) * 1998-06-15 1999-12-22 Toyo Ink Mfg. Co., Ltd. Compound for organic electroluminescence device and organic electroluminescence device
US6465116B1 (en) 1998-06-08 2002-10-15 Nec Corporation Organic electroluminescent device
US6699594B1 (en) 1998-06-08 2004-03-02 Nec Corporation Organic electroluminescent device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6465116B1 (en) 1998-06-08 2002-10-15 Nec Corporation Organic electroluminescent device
US6699594B1 (en) 1998-06-08 2004-03-02 Nec Corporation Organic electroluminescent device
EP0965629A1 (en) * 1998-06-15 1999-12-22 Toyo Ink Mfg. Co., Ltd. Compound for organic electroluminescence device and organic electroluminescence device

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