JP2003073665A - Material for light-emitting element - Google Patents
Material for light-emitting elementInfo
- Publication number
- JP2003073665A JP2003073665A JP2001265803A JP2001265803A JP2003073665A JP 2003073665 A JP2003073665 A JP 2003073665A JP 2001265803 A JP2001265803 A JP 2001265803A JP 2001265803 A JP2001265803 A JP 2001265803A JP 2003073665 A JP2003073665 A JP 2003073665A
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- JP
- Japan
- Prior art keywords
- light emitting
- emitting material
- light
- present
- integer
- 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
Links
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、有機エレクトロル
ミネッセント（ＥＬ）素子及びエレクトロケミルミネッ
セント（ＥＣＬ）素子などの発光素子に用いられる発光
材料に関するものである。TECHNICAL FIELD The present invention relates to a light emitting material used for a light emitting element such as an organic electroluminescent (EL) element and an electrochemiluminescent (ECL) element.
【０００２】[0002]
【従来の技術】近年、半導体回路の高密度集積化が進
み、高機能な情報端末が小型化し、携帯が可能となっ
た。このため、薄型、軽量、低消費電力の表示素子の研
究が活発化している。例えば、液晶ディスプレイ（ＬＣ
Ｄ）は小型携帯機器からノート型パソコンのディスプレ
イまでをカバーし、ブラウン管ディスプレイ（ＣＲＴ）
に置き換わる存在にまで成長している。さらに、動画に
耐え得る次世代型表示素子として有機ＥＬ素子などが注
目されている。2. Description of the Related Art In recent years, high-density integration of semiconductor circuits has progressed, and highly functional information terminals have become smaller and portable. For this reason, research on thin, lightweight, and low power consumption display elements has become active. For example, a liquid crystal display (LC
D) covers everything from small portable devices to laptop displays, and cathode ray tube displays (CRT)
It has grown to become a replacement for. Further, organic EL elements and the like have been attracting attention as next-generation display elements that can endure moving images.
【０００３】エレクトロケミルミネッセント（ＥＣＬ）
素子も、上記のような素子の１つである。ＥＣＬ素子
は、有機ＥＬ素子と同様、自発光型素子であるが、その
最大の特徴は溶液から発光が得られる点である。Electrochemiluminescent (ECL)
The element is also one of the elements described above. Like the organic EL element, the ECL element is a self-luminous element, but its main feature is that it can emit light from a solution.
【０００４】上記有機ＥＬ素子などの発光素子に用いら
れる発光材料としては、印加した電流に対し高い輝度を
示すもの、すなわち発光効率の高いものが求められてい
る。このような発光材料として、三重項状態から発光す
る材料である、以下の構造を有するトリス（２−フェニ
ルピリジン）イリジウム：Ｉｒ（ｐｐｙ）３が知られて
いる。As a light emitting material used for a light emitting element such as the above organic EL element, a material exhibiting a high luminance with respect to an applied current, that is, a material having a high luminous efficiency is required. As such a light emitting material, tris (2-phenylpyridine) iridium: Ir (ppy) 3 having the following structure, which is a material that emits light from the triplet state, is known.
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】[0006]
【発明が解決しようとする課題】しかしながら、上記の
発光材料は、発光電圧が高いという問題があった。本発
明の目的は、発光効率が高く、かつ発光電圧が低い発光
素子用発光材料を提供することにある。However, the above-mentioned light emitting material has a problem that the light emitting voltage is high. An object of the present invention is to provide a light emitting material for a light emitting device, which has high luminous efficiency and low emission voltage.
【０００７】[0007]
【課題を解決するための手段】本発明の発光素子用発光
材料は、以下の一般式（Ｉ）で表されることを特徴とす
るイリジウム含有有機金属化合物である。The light emitting material for a light emitting device of the present invention is an iridium-containing organometallic compound represented by the following general formula (I).
【０００８】[0008]
【化３】 [Chemical 3]
【０００９】（ここでＲは、ＣnＨ2n+1（ｎは１〜１０
の整数）、ＯＣnＨ2n+1（ｎは１〜５の整数）、Ｎ（Ｃn
Ｈ2n+1)2（ｎは１〜５の整数）、フェニル基、ナフチル
基、ＣＮ、Ｆ、Ｃｌ、Ｂｒ、またはＩを表す。）
本発明の発光材料の構造は、従来のＩｒ（ｐｐｙ）３の
配位子であるピリジンの３位の位置に置換基Ｒが導入さ
れている。置換基Ｒとしては、上記のようなものが挙げ
られるが、これらの中でも、炭素数１〜１０（好ましく
は炭素数１〜５）のアルキル基、フェニル基、ナフチル
基等が特に好ましい。(Here, R is C n H 2n + 1 (n is 1 to 10)
, N), OC n H 2n + 1 (n is an integer of 1 to 5), N (C n
H 2n + 1 ) 2 (n is an integer of 1 to 5), a phenyl group, a naphthyl group, CN, F, Cl, Br, or I. In the structure of the light emitting material of the present invention, the substituent R is introduced at the 3-position of pyridine, which is a conventional Ir (ppy) 3 ligand. Examples of the substituent R include those described above, and among these, an alkyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms), a phenyl group, a naphthyl group and the like are particularly preferable.
【００１０】置換基Ｒを上記の位置に導入することによ
り、発光電圧を低くすることができ、発光効率を高める
ことができる。上記本発明の発光材料は、Ｉｒ（ｐｐ
ｙ）３と同様の合成方法により合成することができる。
例えば、Ｉｎｏｒｇ．Ｃｈｅｍ．１９９１，３０，１６
８５〜１６８７頁に記載された方法により合成すること
ができる。具体的には、Ｉｒ（ａｃａｃ）3に、３位に
置換基Ｒを導入した２−フェニルピリジンを反応させる
ことにより合成することができる。By introducing the substituent R into the above position, the emission voltage can be lowered and the emission efficiency can be increased. The light emitting material of the present invention is Ir (pp
y) It can be synthesized by the same synthesis method as in 3.
For example, Inorg. Chem. 1991,30,16
It can be synthesized by the method described on pages 85 to 1687. Specifically, it can be synthesized by reacting Ir (acac) 3 with 2-phenylpyridine having a substituent R introduced at the 3-position.
【００１１】本発明の発光材料は、有機ＥＬ素子及びＥ
ＣＬ素子などの発光材料として用いることができる。有
機ＥＬ素子の発光材料として用いる場合には、発光層に
ホストとともに含有されるドーパントとして用いること
ができる。The luminescent material of the present invention is an organic EL device or an E device.
It can be used as a light emitting material for CL devices and the like. When used as a light emitting material for an organic EL device, it can be used as a dopant contained in the light emitting layer together with the host.
【００１２】本発明の有機ＥＬ素子は、上記本発明の発
光材料を発光層に含有することを特徴としている。The organic EL device of the present invention is characterized by containing the above-mentioned light emitting material of the present invention in a light emitting layer.
【００１３】[0013]
【発明の実施の形態】以下、本発明を具体的な実施例に
より説明するが、本発明は以下の実施例に限定されるも
のではない。BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described below with reference to specific examples, but the present invention is not limited to the following examples.
【００１４】（実施例１）ガラス基板上に、ＩＴＯから
なる陽極を形成し、この上にホール輸送層、発光層、ホ
ールブロック層、電子輸送層、及び陰極を真空蒸着法に
より形成し、陽極／ホール輸送層／発光層／ホールブロ
ック層／電子輸送層／陰極の素子構造を有する有機ＥＬ
素子を作製した。(Example 1) An anode made of ITO was formed on a glass substrate, and a hole transport layer, a light emitting layer, a hole block layer, an electron transport layer, and a cathode were formed thereon by a vacuum vapor deposition method, and the Organic EL having a device structure of / hole transport layer / light emitting layer / hole block layer / electron transport layer / cathode
A device was produced.
【００１５】陽極として、厚み１０００ÅのＩＴＯ膜を
形成した。ホール輸送層として、厚み５００ÅのＮＰＢ
の層を形成した。発光層として、ホストであるＣＢＰに
６重量％のドーパントを含有させたものを厚み１００Å
となるように形成した。An ITO film having a thickness of 1000 liters was formed as an anode. As a hole transport layer, NPB with a thickness of 500Å
Layers were formed. As the light emitting layer, CBP as a host containing 6% by weight of a dopant has a thickness of 100 Å
Was formed so that
【００１６】ホールブロック層として、厚み１００Åの
ＢＣＰの層を形成した。電子輸送層として、厚み２００
ÅのＡｌｑの層を形成した。陰極として、厚み２０００
ÅのＭｇＩｎの層を形成した。As the hole blocking layer, a BCP layer having a thickness of 100Å was formed. The electron transport layer has a thickness of 200
A layer of Alq was formed. As a cathode, thickness 2000
A Å layer of MgIn was formed.
【００１７】ＮＰＢは、Ｎ，Ｎ′−ジ（ナフタレン−１
−イル）−Ｎ，Ｎ′−ジフェニル−ベンジジンであり、
以下の構造を有する化合物である。NPB is N, N'-di (naphthalene-1).
-Yl) -N, N'-diphenyl-benzidine,
It is a compound having the following structure.
【００１８】[0018]
【化４】 [Chemical 4]
【００１９】ＣＢＰは、４，４′−ビス（カルバゾール
−９−イル）−ビフェニルであり、以下の構造を有する
化合物である。CBP is 4,4'-bis (carbazol-9-yl) -biphenyl, which is a compound having the following structure.
【００２０】[0020]
【化５】 [Chemical 5]
【００２１】ＢＣＰは、２，９−ジメチル−４，７−ジ
フェニル−１，１０−フェナントロリンであり、以下の
構造を有する化合物である。BCP is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, which is a compound having the following structure.
【００２２】[0022]
【化６】 [Chemical 6]
【００２３】Ａｌｑは、トリス（８−ヒドロキシキノリ
ナト）アルミニウムであり、以下の構造を有する化合物
である。Alq is tris (8-hydroxyquinolinato) aluminum, which is a compound having the following structure.
【００２４】[0024]
【化７】 [Chemical 7]
【００２５】本実施例では、発光層に含ませるドーパン
トとして、トリス（３−メチル−２−フェニルピリジ
ン）イリジウム：Ｉｒ（３Ｍｅｐｐｙ）３を用いた。こ
の化合物は、以下の構造を有する本発明の発光材料であ
る。In this example, tris (3-methyl-2-phenylpyridine) iridium: Ir (3Meppy) 3 was used as the dopant contained in the light emitting layer. This compound is a light emitting material of the present invention having the following structure.
【００２６】[0026]
【化８】 [Chemical 8]
【００２７】上記構造式から明らかなように、置換基Ｒ
としてメチル基を有する本発明の発光材料である。As is clear from the above structural formula, the substituent R
Is a light emitting material of the present invention having a methyl group as.
【００２８】（実施例２）発光層に含ませるドーパント
として、トリス（３−エチル−２−フェニルピリジン）
イリジウム：Ｉｒ（３Ｅｔｐｐｙ）３を用いる以外は、
上記実施例１と同様にして有機ＥＬ素子を作製した。こ
の化合物は、以下の構造を有する本発明の発光材料であ
る。Example 2 Tris (3-ethyl-2-phenylpyridine) was used as a dopant contained in the light emitting layer.
Iridium: Ir (3Etppy) 3 is used
An organic EL device was produced in the same manner as in Example 1 above. This compound is a light emitting material of the present invention having the following structure.
【００２９】[0029]
【化９】 [Chemical 9]
【００３０】上記構造式に示すように、置換基Ｒとして
エチル基を有する本発明の発光材料である。As shown in the above structural formula, the luminescent material of the present invention has an ethyl group as the substituent R.
【００３１】（実施例３）発光層に含ませるドーパント
として、トリス（３−フェニル−２−フェニルピリジ
ン）イリジウム：Ｉｒ（３Ｐｈｐｐｙ）３を用いる以外
は、上記実施例１と同様にして、有機ＥＬ素子を作製し
た。この化合物は、以下の構造を有する本発明の発光材
料である。Example 3 An organic EL device was manufactured in the same manner as in Example 1 except that tris (3-phenyl-2-phenylpyridine) iridium: Ir (3Phppy) 3 was used as the dopant contained in the light emitting layer. A device was produced. This compound is a light emitting material of the present invention having the following structure.
【００３２】[0032]
【化１０】 [Chemical 10]
【００３３】上記構造式に示すように、置換基Ｒとして
フェニル基を有する本発明の発光材料である。As shown in the above structural formula, the luminescent material of the present invention has a phenyl group as the substituent R.
【００３４】（比較例１）発光層に含ませるドーパント
として、従来のＩｒ（ｐｐｙ）３を用いる以外は、上記
実施例１と同様にして有機ＥＬ素子を作製した。Comparative Example 1 An organic EL device was prepared in the same manner as in Example 1 except that the conventional Ir (ppy) 3 was used as the dopant contained in the light emitting layer.
【００３５】〔有機ＥＬ素子の発光特性の評価〕以上の
ようにして作製した実施例１〜３及び比較例１の有機Ｅ
Ｌ素子について、１０ｍＡ／ｃｍ2の電流を電極に印加
し、発光効率、発光波長、最大輝度、及び輝度８０００
ｃｄ／ｍ2のときの駆動電圧を測定した。測定結果を表
１に示す。[Evaluation of Light Emitting Properties of Organic EL Element] Organic E of Examples 1 to 3 and Comparative Example 1 produced as described above.
For the L element, a current of 10 mA / cm 2 was applied to the electrodes, and the luminous efficiency, the emission wavelength, the maximum luminance, and the luminance of 8000
The driving voltage at cd / m 2 was measured. The measurement results are shown in Table 1.
【００３６】[0036]
【表１】 [Table 1]
【００３７】表１から明らかなように、ドーパント材料
として、本発明に従う発光材料を用いた実施例１〜３
は、ドーパント材料として、従来のＩｒ（ｐｐｙ）３を
用いた比較例１に比べ、発光効率が高くなるとともに、
駆動電圧（発光電圧）が低下していることがわかる。As is apparent from Table 1, Examples 1 to 3 using the light emitting material according to the present invention as the dopant material.
Is higher in luminous efficiency than Comparative Example 1 using Ir (ppy) 3 as a dopant material, and
It can be seen that the drive voltage (light emission voltage) has dropped.
【００３８】[0038]
【発明の効果】本発明の発光材料を用いることにより、
有機ＥＬ素子及びＥＣＬ素子などの発光素子において、
発光効率を高めることができ、発光電圧を低減すること
ができる。従って、本発明の発光材料は、携帯機器など
の低電圧駆動機器における発光素子に有用なものであ
る。By using the light emitting material of the present invention,
In light emitting devices such as organic EL devices and ECL devices,
The light emission efficiency can be increased and the light emission voltage can be reduced. Therefore, the light emitting material of the present invention is useful as a light emitting element in a low voltage driving device such as a mobile device.
Claims (3)
徴とする発光素子用発光材料。 【化１】 （ここでＲは、ＣnＨ2n+1（ｎは１〜１０の整数）、Ｏ
ＣnＨ2n+1（ｎは１〜５の整数）、Ｎ（ＣnＨ2n+1)2（ｎ
は１〜５の整数）、フェニル基、ナフチル基、ＣＮ、
Ｆ、Ｃｌ、Ｂｒ、またはＩを表す。）1. A light emitting material for a light emitting device, which is represented by the following general formula (I). [Chemical 1] (Here, R is C n H 2n + 1 (n is an integer of 1 to 10), O
C n H 2n + 1 (n is an integer of 1 to 5), N (C n H 2n + 1 ) 2 (n
Is an integer of 1 to 5), a phenyl group, a naphthyl group, CN,
Represents F, Cl, Br, or I. )
光層にホストとともに含有されるドーパントであること
を特徴とする請求項１に記載の発光素子用発光材料。2. The light emitting material for a light emitting device according to claim 1, which is a dopant contained together with the host in the light emitting layer of the organic electroluminescent device.
光層に含有することを特徴とする有機エレクトロルミネ
ッセント素子。3. An organic electroluminescent element comprising the light emitting material according to claim 1 or 2 in a light emitting layer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001265803A JP3960765B2 (en) | 2001-09-03 | 2001-09-03 | Luminescent material for light emitting device |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001265803A JP3960765B2 (en) | 2001-09-03 | 2001-09-03 | Luminescent material for light emitting device |
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|---|---|
| JP2003073665A true JP2003073665A (en) | 2003-03-12 |
| JP3960765B2 JP3960765B2 (en) | 2007-08-15 |
Family
ID=19092214
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Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003109758A (en) * | 2001-09-27 | 2003-04-11 | Konica Corp | Organic electroluminescent element |
| WO2005083033A1 (en) * | 2004-02-26 | 2005-09-09 | Konica Minolta Holdings, Inc. | Material for organic electroluminescence element, organic electroluminescence element, display device and illumination device |
| EP1642951A2 (en) * | 2004-10-04 | 2006-04-05 | LG Electronics Inc. | Iridium-based luminescent compounds having phenylpyridine moieties with organosilicon group, and organic electroluminescence devices using the compounds as colour-emitting materials |
| JP2008091906A (en) * | 2007-09-26 | 2008-04-17 | Konica Minolta Holdings Inc | Organic electroluminescent element |
| EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
| EP2276089A2 (en) | 2004-07-27 | 2011-01-19 | Global OLED Technology LLC | Method for reducing moisture contamination in a top-emitting oled using a dessicant |
| US8034465B2 (en) | 2007-06-20 | 2011-10-11 | Global Oled Technology Llc | Phosphorescent oled having double exciton-blocking layers |
| US8057916B2 (en) | 2005-04-20 | 2011-11-15 | Global Oled Technology, Llc. | OLED device with improved performance |
| WO2012041851A1 (en) | 2010-09-29 | 2012-04-05 | Basf Se | Security element |
| WO2012045710A1 (en) | 2010-10-07 | 2012-04-12 | Basf Se | Phenanthro[9,10-b]furans for electronic applications |
| US8247088B2 (en) | 2008-08-28 | 2012-08-21 | Global Oled Technology Llc | Emitting complex for electroluminescent devices |
| US8253126B2 (en) | 1999-12-31 | 2012-08-28 | Lg Chem. Ltd. | Organic electronic device |
| US8324800B2 (en) | 2008-06-12 | 2012-12-04 | Global Oled Technology Llc | Phosphorescent OLED device with mixed hosts |
| JP2013539206A (en) * | 2010-07-30 | 2013-10-17 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Electroluminescent device using electroluminescent compound as luminescent material |
| US8680693B2 (en) | 2006-01-18 | 2014-03-25 | Lg Chem. Ltd. | OLED having stacked organic light-emitting units |
| US8956738B2 (en) | 2005-10-26 | 2015-02-17 | Global Oled Technology Llc | Organic element for low voltage electroluminescent devices |
| US9028979B2 (en) | 2009-06-18 | 2015-05-12 | Basf Se | Phenanthroazole compounds as hole transporting materials for electro luminescent devices |
| US9040170B2 (en) | 2004-09-20 | 2015-05-26 | Global Oled Technology Llc | Electroluminescent device with quinazoline complex emitter |
| US9079872B2 (en) | 2010-10-07 | 2015-07-14 | Basf Se | Phenanthro[9, 10-B]furans for electronic applications |
| US9118020B2 (en) | 2006-04-27 | 2015-08-25 | Global Oled Technology Llc | Electroluminescent devices including organic eil layer |
| US9666826B2 (en) | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| US20170213990A1 (en) * | 2016-01-27 | 2017-07-27 | Nichem Fine Technology Co., Ltd. | Compound and electronic device including same |
| CN108250247A (en) * | 2016-12-23 | 2018-07-06 | 环球展览公司 | Electroluminescent organic material and device |
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