JPH0417294A - Organic thin film el element - Google Patents

Organic thin film el element

Info

Publication number
JPH0417294A
JPH0417294A JP2120311A JP12031190A JPH0417294A JP H0417294 A JPH0417294 A JP H0417294A JP 2120311 A JP2120311 A JP 2120311A JP 12031190 A JP12031190 A JP 12031190A JP H0417294 A JPH0417294 A JP H0417294A
Authority
JP
Japan
Prior art keywords
thin film
organic
carboxylic acid
ester
group
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.)
Granted
Application number
JP2120311A
Other languages
Japanese (ja)
Other versions
JP2973465B2 (en
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
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Application filed by NEC Corp filed Critical NEC Corp
Priority to JP2120311A priority Critical patent/JP2973465B2/en
Publication of JPH0417294A publication Critical patent/JPH0417294A/en
Application granted granted Critical
Publication of JP2973465B2 publication Critical patent/JP2973465B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Abstract

PURPOSE:To improve luminous efficiency of an element and make it possible to slow a deterioration speed down by using 3,9-perylene carboxylic acid ester as a material used for an illuminant layer. CONSTITUTION:A principal component of an organic illuminant thin film layer 14 of an organic thin film EL element, which has the organic illuminant thin film layer 14 between a pair of electrodes one of which is transparent is 3,9- perylene carboxylic acid ester described in a formula I. In the formula I, R represents an alkyl group, an alkoxyl group, a phenyl group, or a subsituent phenyl group. The 3,9-perylene carboxylic acid ester to be used includes 3,9- perylene carboxylic acid diphenyl ester, 3,9-perylene carboxylic acid dimethyl ester, and 3,9-perylene carboxylic acid diethyl ester. Thus, luminescent characteristics and reliability can be improved.

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ティ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 (Industrial Application Field) The present invention relates to an organic thin film EL element used in flat light sources and displays.

(従来の技術) 有機物質を用いた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。例えばアントラセンやペリレン等の縮合多環芳
香族系を原料としてLB法や真空蒸着法で薄膜化した直
流駆動の有機薄膜EL素子が製造され、その発光特性が
研究されている。しかし、従来の有機薄膜EL素子は駆
動電圧が高く、かつその発光輝度・効率が無機薄膜EL
素子のそれと比ベて低かった。また、発光特性の劣化も
著しく、実用レベルのものではなかった。
(Prior Art) EL (electroluminescent) devices using organic materials are attracting attention as a means of realizing inexpensive, large-area, full-color display devices. For example, DC-driven organic thin-film EL devices have been produced using fused polycyclic aromatic systems such as anthracene and perylene as raw materials and made into thin films by the LB method or vacuum evaporation method, and their light-emitting characteristics have been studied. However, conventional organic thin film EL devices require a high driving voltage, and their luminance and efficiency are lower than those of inorganic thin film EL devices.
It was lower than that of Motoko. Furthermore, the luminescent properties were significantly deteriorated and were not at a practical level.

ところが、最近有機薄膜を積層構造にした新しいタイプ
の有機薄膜EL素子が報告され強い関心を集めている(
化学と工業、42巻、2023ページ、1989年)。
However, recently, a new type of organic thin film EL device with a layered structure of organic thin films has been reported and is attracting strong interest (
Chemistry and Industry, Volume 42, Page 2023, 1989).

強い蛍光を発する有機色素を有機発光体薄膜層に電荷輸
送性有機物を電荷注入層に使用して明るい発光を得たと
報告している。IOVの直流印加で数100cd/m2
の輝度を得ている。最大発光効率は1.01m/Wと、
実用レベルに近い性能を持っている。
They reported that bright light emission was obtained by using an organic dye that emits strong fluorescence as an organic light emitter thin film layer and a charge transporting organic substance as a charge injection layer. Several 100 cd/m2 with IOV DC application
The brightness is obtained. The maximum luminous efficiency is 1.01m/W,
It has performance close to a practical level.

(発明が解決しようとする課題) 前述したように、有機発光体薄膜と有機物の電荷注入層
とを積層した構造の有機薄膜EL素子は10Vの直流印
加で100cd/m以上の明るい発光を示す。この素子
は電流駆動型であるために上記の輝度を得るためには最
低でも10mA/Cm以上の電流を流さなければならな
い。しかし従来用いていた有機物の発光体層では安定し
て充分電流を流すことができなかった。これは通電によ
る発光体層の劣化や、蛍光体薄膜のモーホロジーの変化
によって電子と正孔が有機発光体層に注入されにくくな
ったためである。
(Problems to be Solved by the Invention) As described above, an organic thin film EL element having a structure in which an organic light emitting thin film and an organic charge injection layer are stacked emits bright light of 100 cd/m or more when a 10 V DC is applied. Since this element is of a current drive type, a current of at least 10 mA/Cm or more must flow in order to obtain the above brightness. However, the conventionally used organic light emitter layer was unable to stably and sufficiently flow current. This is because it becomes difficult for electrons and holes to be injected into the organic light emitting layer due to deterioration of the light emitting layer due to energization and changes in the morphology of the phosphor thin film.

従って、素子発光効率を更に向上させ、且つ劣化速度を
低下させることがこの有機薄膜EL素子の実用化の上で
非常に重要である。しかし、従来の技術ではこれらの問
題解決が困難であった。
Therefore, it is very important to further improve the device luminous efficiency and reduce the deterioration rate for the practical use of this organic thin film EL device. However, it has been difficult to solve these problems with conventional techniques.

(課題を解決するための手段) 従来技術の課題解決のために鋭意研究したところ、有機
発光体薄膜層の材料とし3,9−ペリレンジカルボン酸
エステルが優れた特性を示すことを見いだした。本発明
が提供する手段は、少なくとも一方が透明である一対の
電極間に、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、有機発光体薄膜層の主成分が一般
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
とを特徴とする有機薄膜EL素子である。また、前記一
対の電極間に、有機電荷輸送性薄膜と前記有機発光体薄
膜とを積層してもよい。
(Means for Solving the Problems) As a result of intensive research to solve the problems of the prior art, it was discovered that 3,9-perylene dicarboxylic acid ester exhibits excellent properties as a material for the organic light emitting thin film layer. The means provided by the present invention provides an organic thin film EL element having at least an organic light emitting thin film layer between a pair of electrodes, at least one of which is transparent, in which the main component of the organic light emitting thin film layer has a 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. Further, an organic charge transporting thin film and the organic light emitting thin film may be laminated between the pair of electrodes.

本発明に用いれる3、9−ペリレンジカルボン酸エステ
ルの例として、3,9−ペリレンジカルボン酸ジフェニ
ルエステル 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。
Examples of the 3,9-perylene dicarboxylic acid ester used in the present invention include 3,9-perylene dicarboxylic acid diphenyl ester thyl 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-dimethoxyphenyl) ester, 3,9-perylene dicarboxylic acid-
Di(p-dimethylaminophenyl) ester, 3,9
Examples include, but are not limited to, -perylene dicarboxylic acid di-(p-diethylaminophenyl) ester.

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Sn02:Sb。
Note that any material commonly used as a transparent electrode may be used; for example, in addition to ITO, Sn02:Sb may be used.

ZnO:AlやAuなどがあげられる。背面電極にはI
n。
ZnO: Examples include Al and Au. I on the back electrode
n.

Mg,AgやMg:Agなどが使われる。Mg, Ag, Mg:Ag, etc. are used.

本発明により、従来の有機薄膜EL素子に比べ発光効率
は1.5倍改善された。このように本発明で重要な点は
、発光体層に用いる材料が3,9−ペリレンジカルボン
酸エステルであることを特徴とする有機薄膜EL素子で
あり、発光体層以外の素子を構成する材料そのものでは
ない。また、有機発光体薄膜と背面電極の間に有機電子
注入層を設置した、いわゆる3層構造の有機薄膜EL素
子においても本発明は有効である。
According to the present invention, the luminous efficiency is improved by 1.5 times compared to conventional organic thin film EL devices. As described above, the important point of the present invention is an organic thin film EL device characterized in that the material used for the luminescent layer is 3,9-perylene dicarboxylic acid ester, and the material used for the device other than the luminescent layer It's not that. Further, the present invention is also effective in an organic thin film EL element having a so-called three-layer structure in which an organic electron injection layer is provided between an organic light emitting thin film and a back electrode.

(実施例) 以下実施例を以て、本発明の詳細な説明する。(Example) The present invention will be described in detail below with reference to Examples.

本発明に適用できる構造を第1図から第4図−二示す。Structures applicable to the present invention are shown in FIGS. 1 to 4-2.

基本的にはガラス基板11上に電極12および15で挟
まれた有機発光体薄膜層14を有する。これに加えて、
有機正孔輸送性薄膜層12や有機電子輸送性薄膜層16
を有してもよい。また、有機正孔輸送性薄膜12および
有機電子輸送性薄膜16を共に有してもよい。
Basically, it has an organic light emitting thin film layer 14 sandwiched between electrodes 12 and 15 on a glass substrate 11. In addition to this,
Organic hole transporting thin film layer 12 and organic electron transporting thin film layer 16
It may have. Moreover, it may have both the organic hole transporting thin film 12 and the organic electron transporting thin film 16.

実施例1 有機発光体として3,9−ペリレンジカルボン酸ジフェ
ニルエステルを用いた。第2図に示すようにガラス基板
11上にITO透明電極12を形成してから有機正孔輸
送性薄膜13として1,1−ビス(4−N、 N−ジト
リルアミノフェニル)シクロヘキサン薄膜を50OA、
更に有機発光体薄膜14を1000人、1O−7Tor
rの真空中で蒸着して形成した。最後に背面金属電極1
5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。
Example 1 3,9-perylene dicarboxylic acid diphenyl ester was used as an organic light emitter. As shown in FIG. 2, an ITO transparent electrode 12 is formed on a glass substrate 11, and then a 1,1-bis(4-N, N-ditolylaminophenyl)cyclohexane thin film is deposited at 50 OA as an organic hole transporting thin film 13. ,
Furthermore, the organic light emitting thin film 14 was heated to 1000 people and 10-7 Torr.
It was formed by vapor deposition in a vacuum of r. Finally, the back metal electrode 1
As No. 5, 1,500 layers of In were formed by electron beam evaporation to create 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430cd/m2の明るい赤
色発光が得られた。従来の素子に比べ発光輝度・効率が
1.5倍改善されている。
When the luminescent properties of this element were measured in dry nitrogen, bright red luminescence of 430 cd/m2 was obtained when a DC voltage of about 10 V was applied. Compared to conventional elements, luminance and efficiency are improved by 1.5 times.

実施例2 有機発光体として3,9−ペリレンジカルボン酸ジフェ
ニルエステルを用いた。第3図に示すようにカラス基板
11上にITO透明電極12を形成してから有機発光体
薄膜14を700人、1O−7Torrの真空中で蒸着
して形成した。更に電子輸送性薄膜層16として2−(
4’−tert−ブチルフェニル)−5−(4”−ビフ
ェニル)−1,3,4−オキサジアゾールを500人、
10−7Torrの真空中で蒸着して形成した。最後に
背面金属電極15としてInを電子ビーム蒸着法で15
00人形成して有機薄膜EL素子を作成した。
Example 2 3,9-perylene dicarboxylic acid diphenyl ester was used as an organic light emitter. As shown in FIG. 3, an ITO transparent electrode 12 was formed on a glass substrate 11, and then an organic light emitting thin film 14 was deposited by 700 people in a vacuum of 10-7 Torr. Further, as the electron transporting thin film layer 16, 2-(
4'-tert-butylphenyl)-5-(4''-biphenyl)-1,3,4-oxadiazole for 500 people,
It was formed by vapor deposition in a vacuum of 10-7 Torr. Finally, as the back metal electrode 15, In is deposited using an electron beam evaporation method.
00 people formed 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200cd/mの明るい赤色
発光が得られた。従来の素子に比べ発光輝度。
When the luminescent properties of this device were measured in dry nitrogen, bright red luminescence of 200 cd/m was obtained when a DC voltage of about 10 V was applied. Luminous brightness compared to conventional elements.

効率が1.2倍改善されている。Efficiency is improved by 1.2 times.

実施例3 有機発光体として3,9−ペリレンジカルボン酸ジフェ
ニルエステルを用いた。第4図に示すようにカラス基板
11上にITO透明電極12を形成してから有機正孔輸
送性薄膜13として1,1−ビス(4−N、N−ジトリ
アルアミノフェニル)シクロヘキサン薄膜を50OA、
有機発光体薄膜14を150人、1O−7Torrの真
空中で蒸着して形成した。更に電子輸送性薄膜層16と
し、て2−(4’−tert−ブチルフェニル)−5−
(4”−ビフェニル)−1,3,4−オキサジアゾール
を500人、10−7Torrの真空中で蒸着して形成
した。最後に背面金属電極15としてInを電子ビーム
蒸着法で1500人形成して3層構造の有機薄膜EL素
子を作成した。
Example 3 3,9-perylene dicarboxylic acid diphenyl ester was used as an organic light emitter. As shown in FIG. 4, an ITO transparent electrode 12 is formed on a glass substrate 11, and then a 1,1-bis(4-N,N-ditrialaminophenyl)cyclohexane thin film of 50OA is formed as an organic hole transporting thin film 13. ,
The organic light emitting thin film 14 was deposited by 150 people in a vacuum of 10-7 Torr. Further, as the electron transporting thin film layer 16, 2-(4'-tert-butylphenyl)-5-
(4"-biphenyl)-1,3,4-oxadiazole was deposited by 500 people in a vacuum of 10-7 Torr.Finally, In was deposited as the back metal electrode 15 by electron beam evaporation by 1500 people. An organic thin film EL device with a three-layer structure was fabricated.

この素子の発光特性を乾燥窒素中で測定したところ、約
15Vの直流電圧の印加で250cd/m2の明るい赤
色発光が得られた。従来の素子に比べ発光輝度・効率が
1.5倍改善されている。
When the luminescent properties of this element were measured in dry nitrogen, bright red luminescence of 250 cd/m2 was obtained when a DC voltage of about 15 V was applied. Compared to conventional elements, luminance and efficiency are improved by 1.5 times.

(発明の効果) 以上説明したように本発明により発光特性及び信頼性を
大幅に改善することができた。
(Effects of the Invention) As explained above, the present invention was able to significantly improve the light emission characteristics and reliability.

このように、本発明による有機薄膜EL素子は低電圧駆
動の薄膜発光体としてきわめて有効であり、その工業的
価値は高い。
As described above, the organic thin film EL device according to the present invention is extremely effective as a thin film light emitter driven at low voltage, and its industrial value is high.

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

第1図は本発明の有機薄膜EL素子の断面構造図、第2
図〜第4図は本発明の実施例の断面構造図である。 11・・・ガラス基板、12・・・ITO透明電極、1
30.・有機正孔輸送性薄膜層、 14・・・有機発光体薄膜層、15・・・背面電極、1
6・・・有機電デ輸送性薄膜層
FIG. 1 is a cross-sectional structural diagram of the organic thin film EL device of the present invention, and FIG.
4 to 4 are cross-sectional structural diagrams of embodiments of the present invention. 11... Glass substrate, 12... ITO transparent electrode, 1
30.・Organic hole transporting thin film layer, 14...Organic light emitter thin film layer, 15...Back electrode, 1
6...Organic charge transporting thin film layer

Claims (2)

【特許請求の範囲】[Claims] (1)少なくとも一方が透明である一対の電極間に、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、有機発光体薄膜層の主成分が一般式 ▲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
とを特徴とする有機薄膜EL素子。
(1) In an organic thin-film EL device that has at least an organic light-emitting thin film layer between a pair of electrodes, at least one of which is transparent, the main component of the organic light-emitting thin film layer has a general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ An organic thin film EL device characterized in that it is a 3,9-perylene dicarboxylic acid ester represented by the formula (wherein R is selected from the group consisting of an alkyl group, an alkoxyl group, a phenyl group, and a substituted phenyl group).
(2)少なくとも一方が透明である一対の電極間に、有
機電荷輸送性薄膜と有機発光体薄膜が積層された有機薄
膜EL素子において、有機発光体薄膜層の主成分が一般
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、フエニル基
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
とを特徴とする有機薄膜EL素子。
(2) In an organic thin film EL device in which an organic charge transporting thin film and an organic light emitting thin film are laminated between a pair of electrodes, at least one of which is transparent, the main component of the organic light emitting thin film layer has a general formula ▲ mathematical formula, chemical formula , tables, etc. ▼ (wherein R is selected from the group consisting of an alkyl group, an alkoxyl group, a phenyl group, and a substituted phenyl group). Organic thin film EL device.
JP2120311A 1990-05-10 1990-05-10 Organic thin film EL device Expired - Lifetime JP2973465B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2120311A JP2973465B2 (en) 1990-05-10 1990-05-10 Organic thin film EL device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2120311A JP2973465B2 (en) 1990-05-10 1990-05-10 Organic thin film EL device

Publications (2)

Publication Number Publication Date
JPH0417294A true JPH0417294A (en) 1992-01-22
JP2973465B2 JP2973465B2 (en) 1999-11-08

Family

ID=14783104

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2120311A Expired - Lifetime JP2973465B2 (en) 1990-05-10 1990-05-10 Organic thin film EL device

Country Status (1)

Country Link
JP (1) JP2973465B2 (en)

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
US10237375B2 (en) 2000-09-01 2019-03-19 Callahan Cellular L.L.C. Communications terminal, a system and a method for internet/network telephony

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
US10237375B2 (en) 2000-09-01 2019-03-19 Callahan Cellular L.L.C. Communications terminal, a system and a method for internet/network telephony

Also Published As

Publication number Publication date
JP2973465B2 (en) 1999-11-08

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