JP2008074939A - Organic electroluminescence element material, organic electroluminescence element, display device and illumination device - Google Patents

Organic electroluminescence element material, organic electroluminescence element, display device and illumination device Download PDF

Info

Publication number
JP2008074939A
JP2008074939A JP2006255132A JP2006255132A JP2008074939A JP 2008074939 A JP2008074939 A JP 2008074939A JP 2006255132 A JP2006255132 A JP 2006255132A JP 2006255132 A JP2006255132 A JP 2006255132A JP 2008074939 A JP2008074939 A JP 2008074939A
Authority
JP
Japan
Prior art keywords
group
general formula
layer
organic electroluminescence
organic el
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
JP2006255132A
Other languages
Japanese (ja)
Other versions
JP5589251B2 (en
Inventor
Tomohiro Oshiyama
Shinya Otsu
Motoaki Sugino
信也 大津
智寛 押山
元昭 杉野
Original Assignee
Konica Minolta Holdings Inc
コニカミノルタホールディングス株式会社
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 Konica Minolta Holdings Inc, コニカミノルタホールディングス株式会社 filed Critical Konica Minolta Holdings Inc
Priority to JP2006255132A priority Critical patent/JP5589251B2/en
Publication of JP2008074939A publication Critical patent/JP2008074939A/en
Application granted granted Critical
Publication of JP5589251B2 publication Critical patent/JP5589251B2/en
Application status is Active legal-status Critical
Anticipated expiration legal-status Critical

Links

Images

Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic electroluminescence element material which exhibits high light emission brightness and a long half-life, to provide an organic electroluminescence element, and to provide an illumination device and a display device each using the element. <P>SOLUTION: This organic electroluminescence element material is characterized by containing a compound having a structure represented by general formula (1) (wherein, Xa is O, S, Se, or Te; Z<SB>1</SB>, Z<SB>2</SB>are each an aromatic hydrocarbon ring or aromatic heterocyclic group, wherein one of Z<SB>1</SB>, Z<SB>2</SB>is the aromatic heterocyclic group; Z<SB>3</SB>is a divalent linkage group or a single bond) as a substituent in the molecule. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は、有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置に関する The present invention relates to an organic electroluminescence device material, an organic electroluminescent element, a display device and a lighting device

従来、発光型の電子ディスプレイデバイスとして、エレクトロルミネッセンスディスプレイ(以下、ELDという)がある。 Conventionally, an emission type electronic display device, an electroluminescence display (hereinafter, referred to as ELD) it is. ELDの構成要素としては、無機エレクトロルミネッセンス素子や有機エレクトロルミネッセンス素子(以下、有機EL素子ともいう)が挙げられる。 The components of the ELD, an inorganic electroluminescent element and an organic electroluminescent device (hereinafter, also referred to as organic EL element). 無機エレクトロルミネッセンス素子は平面型光源として使用されてきたが、発光素子を駆動させるためには交流の高電圧が必要である。 Inorganic electroluminescent element has been used as a flat light source, but in order to drive the element requires a high voltage of alternating current. 有機EL素子は発光する化合物を含有する発光層を陰極と陽極で挟んだ構成を有し、発光層に電子及び正孔を注入して、再結合させることにより励起子(エキシトン)を生成させ、このエキシトンが失活する際の光の放出(蛍光・リン光)を利用して発光する素子であり、数V〜数十V程度の電圧で発光が可能であり、更に自己発光型であるために視野角に富み、視認性が高く、薄膜型の完全固体素子であるために、省スペース、携帯性等の観点から注目されている。 The organic EL element has a structure in which between a cathode and an anode of the light-emitting layer containing a compound that emits light, by injecting electrons and holes into the light emitting layer, by recombination to generate excitons, the excitons is an element that emits light by utilizing emission (fluorescence-phosphorescence) of light when a deactivated, is capable of emitting in several V~ several tens V voltage of about, for more self-luminescent rich in viewing angle, the visibility increases, because a complete solid element of the thin film type, space saving, has attracted attention in view of portability or the like.

しかしながら、今後の実用化に向けた有機EL素子においては、更に低消費電力で効率よく高輝度に発光する有機EL素子の開発が望まれている。 However, in the organic EL element for future practical use, it has been desired to develop an organic EL element that emits light more efficiently a high luminance with low power consumption.

特許第3093796号公報では、スチルベン誘導体、ジスチリルアリーレン誘導体またはトリススチリルアリーレン誘導体に微量の蛍光体をドープし、発光輝度の向上、素子の長寿命化を達成している。 In Japanese Patent No. 3093796 publication, stilbene derivatives, phosphor traces were doped distyrylarylene derivatives or tris styrylarylene derivative, improvement of emission luminance, and achieving a long lifetime of the device. また、8−ヒドロキシキノリンアルミニウム錯体をホスト化合物として、これに微量の蛍光体をドープした有機発光層を有する素子(例えば、特開昭63−264692号公報)、8−ヒドロキシキノリンアルミニウム錯体をホスト化合物として、これにキナクリドン系色素をドープした有機発光層を有する素子(例えば、特開平3−255190号公報)等が知られている。 Also, 8-hydroxyquinoline aluminum complex as a host compound, this element having an organic light-emitting layer doped with a slight amount of a fluorescent substance (e.g., JP-A-63-264692), 8-hydroxyquinoline aluminum complex host compound as a device (e.g., JP-a-3-255190 publication) having an organic light-emitting layer doped with a quinacridone type dye thereto and the like are known.

上記文献に開示されている技術では、励起一重項からの発光を用いる場合一重項励起子と三重項励起子の生成比が1:3であるため、発光性励起種の生成確率が25%であることと、光の取り出し効率が約20%であるため外部取り出し量子効率(ηext)の限界は5%とされている。 In the technique disclosed in the above document, generation ratio of singlet excitons and triplet excitons case of using the light emission from an excited singlet 1: For a 3, generation probability of an emitting exciton species 25% and that, the limit of external extraction quantum efficiency (ηext) for the light extraction efficiency is about 20% is 5%.

以上のように、励起一重項からの発光を用いる場合、一重項励起子と三重項励起子の生成比が1:3であるため発光性励起種の生成確率が25%であり、光の取り出し効率が約20%であるため、外部取り出し量子効率(ηext)の限界は5%とされている。 As described above, when using the light emission from the singlet excited, generating ratio of singlet excitons and triplet excitons is 1: generation probability of an emitting exciton species is 3 are 25%, the light extraction since efficiency of about 20%, the limit of external extraction quantum efficiency (ηext) is 5%.

ところが、プリンストン大より励起三重項からのリン光発光を用いる有機EL素子の報告(M.A.Baldo et al.,Nature、395巻、151〜154頁(1998年))がされて以来、室温でリン光を示す材料の研究が活発になってきている。 However, reports of the organic EL element, employing phosphorescence through the excited triplet from Princeton (M.A.Baldo et al., Nature, 395, pp. 151-154 (1998)) since been at room temperature study of materials that exhibit phosphorescence have come to be active in.

例えば、M. For example, M. A. A. Baldo et al. Baldo et al. ,Nature、403巻、17号、750〜753頁(2000年)、また米国特許第6,097,147号明細書等にも開示されている。 , Nature, 403, pp. 17 No., pp. 750-753 (2000), also disclosed in U.S. Patent No. 6,097,147 and the like.

励起三重項を使用すると、内部量子効率の上限が100%となるため励起一重項の場合に比べて原理的に発光効率が4倍となり、冷陰極管とほぼ同等の性能が得られる可能性があることから照明用途としても注目されている。 With triplet, theoretically luminous efficiency is 4 times of the case of the excited singlet for the upper limit of the internal quantum efficiency of 100% possibility that almost the same performance as a cold cathode tube is obtained It has attracted attention as a lighting applications since there.

例えば、S. For example, S. Lamansky et al. Lamansky et al. ,J. , J. Am. Am. Chem. Chem. Soc. Soc. ,123巻、4304頁(2001年)等においては、多くの化合物がイリジウム錯体系等重金属錯体を中心に合成検討されている。 , 123, pp. In such page 4304 (2001), many compounds have been synthesized and studied about the heavy metal complexes such as iridium complexes. また、前述のM. In addition, the above-mentioned M. A. A. Baldo et al. Baldo et al. ,Nature,403巻、17号、750〜753頁(2000年)においては、ドーパントとして、トリス(2−フェニルピリジン)イリジウムを用いた検討がされている。 , Nature, 403, pp. 17 No. in the page 750-753 (2000), as a dopant tris (2-phenylpyridine) has been studied using iridium.

中心金属をイリジウムの代わりに、白金としたオルトメタル化錯体も注目されている。 The central metal instead of iridium, ortho-metalated complexes and platinum have also been noted. この種の錯体に関しては、配位子に特徴を持たせた例が多数知られている。 For this type of complex, examples which gave characterized ligands are known numerous.

これらリン光発光性ドーパントのホスト化合物として、CBP、m−CPに代表されるカルバゾール誘導体がよく知られている(例えば、特許文献1、2参照。)。 As a host compound of phosphorescent dopant, CBP, carbazole derivatives represented by m-CP is well known (e.g., see Patent Documents 1 and 2.). 特に、青発光のホスト化合物としては、バンドギャップの大きなm−CPやその誘導体が知られている。 In particular, as the host compound of the blue emission, large m-CP and derivative thereof bandgap is known.

一方、正孔阻止層(エキシトン阻止層)の導入により高い発光輝度を得る技術も開示されている。 On the other hand, a technique of obtaining a high luminance by the introduction of a hole blocking layer (exciton blocking layer) is also disclosed. 例えば、パイオニア社により、ある種のアルミニウム錯体を使用する例、フッ素置換化合物を用いることにより、高効率な発光を達成している(例えば、特許文献3、非特許文献1参照。)。 For example, the Pioneer, examples of the use of certain aluminum complex, by using a fluorine-substituted compound, have achieved high-efficiency light emission (e.g., Patent Document 3, Non-Patent Reference 1.).

しかしながら、これらの有機EL材料を用いても効率と寿命を十分に満足する性能に至っておらず、更なる改善が求められていた。 However, not led to satisfactory for performance efficiency and lifetime using these organic EL materials, a further improvement has been required.
国際公開第03/80760号パンフレット WO 03/80760 pamphlet 国際公開第04/74399号パンフレット WO 04/74399 pamphlet 特開2002−8860号公報 JP 2002-8860 JP

本発明は、高い発光輝度を示し、且つ半減寿命の長い有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、及び該素子を用いた照明装置、表示装置を提供することである。 The present invention shows high luminance and long organic electroluminescence element material half-life organic electroluminescent device, and a lighting apparatus using the element is to provide a display device.

本発明の上記目的は、下記の構成により達成される。 The above object of the present invention is achieved by the following constitutions.

1. 1. 下記一般式(1)で表される構造を置換基として分子内に有する化合物を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ス素子材料。 The organic electroluminescent device material characterized by a structure represented by the following general formula (1) a compound having in the molecule as a substituent.

(式中、Xaは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。Z 1 、Z 2は芳香族炭化水素環または芳香族複素環を表すが、いずれか一方は芳香族複素環である。Z 3は2価の連結基または単なる結合手を表す。) (Wherein, Xa is an oxygen atom, a sulfur atom, .Z 1 representing a selenium atom or a tellurium atom, Z 2 represents an aromatic hydrocarbon ring or aromatic heterocyclic ring, is either an aromatic heterocyclic .Z 3 represents a divalent linking group or a single bond.)
2. 2. 前記一般式(1)において、Z 3が単なる結合手を表すことを特徴とする前記1に記載の有機エレクトロルミネッセンス素子材料。 In the general formula (1), the organic electroluminescent device material as described in 1 above, wherein the Z 3, characterized in that the representative of mere bond.

3. 3. 前記一般式(1)において、Z 1 、Z 2の少なくとも一方が六員環であることを特徴とする前記1または2に記載の有機エレクトロルミネッセンス素子材料。 In the general formula (1), the organic electroluminescent device material as described in 1 or 2, wherein at least one of Z 1, Z 2 is a six-membered ring.

4. 4. 前記一般式(1)が下記一般式(2)で表されることを特徴とする前記1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to any one of the 1 to 3, characterized in that the general formula (1) is represented by the following general formula (2).

(式中、Xbは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。X 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 、X 18は各々炭素原子または窒素原子を表すが、その少なくとも一つは窒素原子である。R 1 、R 2は各々置換基を表す。n、mは0≦n+m≦7を満たす0から4の整数を表す。) (Wherein, Xb is an oxygen atom, a sulfur atom, .X 11 representing a selenium atom or a tellurium atom, X 12, X 13, X 14, X 15, X 16, X 17, X 18 are each a carbon atom or a nitrogen atom represents a, .n representing the at least one of which is a nitrogen atom .R 1, R 2 are each a substituent, m represents an integer from 0 satisfying 0 ≦ n + m ≦ 7 4 .)
5. 5. 前記一般式(2)が下記一般式(3)で表されることを特徴とする前記3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescent device material as described in the 3, characterized in that the general formula (2) is represented by the following general formula (3).

(式中、Xcは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 31 、R 32は各々置換基を表す。n31は0から3の整数、m31は0から4の整数を表す。) (Wherein, Xc represents an oxygen atom, a sulfur atom, a selenium atom or .R 31 representing a tellurium atom, R 32 is .n31 each represent a substituent an integer from 0 to 3, m31 represents an integer of 0 to 4. )
6. 6. 前記一般式(2)が下記一般式(4)で表されることを特徴とする前記3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescent device material as described in the 3, characterized in that the general formula (2) is represented by the following general formula (4).

(式中、Xdは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 41 、R 42は各々置換基を表す。n41は0から3の整数、m41は0から4の整数を表す。) (Wherein, Xd represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom represents .R 41, R 42 are each an integer of .n41 representing a substituent from 0 3, m41 represents an integer of 0 to 4. )
7. 7. 前記一般式(2)が下記一般式(5)で表されることを特徴とする前記3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescent device material as described in the 3, characterized in that the general formula (2) is represented by the following general formula (5).

(式中、Xeは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 51 、R 52は各々置換基を表す。n51は0から3の整数、m51は0から4の整数を表す。) (Wherein, Xe represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom .R 51, R 52 is .n51 each represent a substituent an integer from 0 to 3, the integer m51 is from 0 to 4. )
8. 8. 前記一般式(2)が下記一般式(6)で表されることを特徴とする前記3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescent device material as described in the 3, characterized in that the general formula (2) is represented by the following general formula (6).

(式中、Xfは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 61 、R 62は各々置換基を表す。n61は0から3の整数、m61は0から4の整数を表す。) (Wherein, Xf represents an oxygen atom, a sulfur atom, .R 61 representing a selenium atom or a tellurium atom, R 62 is .n61 each represent a substituent an integer from 0 to 3, m61 represents an integer of 0 to 4. )
9. 9. 前記一般式(1)が下記一般式(7)で表されることを特徴とする前記1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to any one of the 1 to 3, characterized in that the general formula (1) is represented by the following general formula (7).

(式中、Xgは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。X 21 、X 22 、X 23 、X 24 、X 25 、X 26 、X 27 、X 28は各々炭素原子または窒素原子を表すが、X 21 、X 22 、X 23 、X 24の少なくとも一つ、且つX 25 、X 26 、X 27 、X 28の少なくとも一つは窒素原子である。R 3 、R 4は各々置換基を表す。p、qは0≦p+q≦6を満たす0から3の整数を表す。) (Wherein, Xg represents an oxygen atom, a sulfur atom, .X 21 representing a selenium atom or a tellurium atom, X 22, X 23, X 24, X 25, X 26, X 27, X 28 are each a carbon atom or a nitrogen atom represents a, at least one, and X 25, .R 3, R 4 at least one is a nitrogen atom of X 26, X 27, X 28 are each substituted X 21, X 22, X 23 , X 24 It represents a group .p, q is an integer of from 0 satisfying 0 ≦ p + q ≦ 6 3.)
10. 10. ホスト化合物及びリン光性化合物を含有する発光層を有する有機エレクトロルミネッセンス素子であって、該素子を構成するいずれかの層に前記1〜9のいずれか1項に記載の有機エレクトロルミネッセンス素子材料を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ス素子。 An organic electroluminescent device having a light-emitting layer containing a host compound and a phosphorescent compound, an organic electroluminescence device material according to any one of the any of the layers constituting the the element 1-9 the organic electroluminescent device characterized by containing.

11. 11. 前記いずれかの層が発光層であることを特徴とする前記10に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to the 10, wherein the one of the layers is a light emitting layer.

12. 12. 前記いずれかの層が正孔阻止層であることを特徴とする前記10に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to the 10, wherein the one of the layers is a hole blocking layer.

13. 13. 前記リン光性化合物がイリジウム錯体化合物または白金錯体化合物であることを特徴とする前記10〜12のいずれか1項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of the 10-12, wherein the phosphorescent compound is an iridium complex compound or a platinum complex compound.

14. 14. 発光が白色であることを特徴とする前記10〜13のいずれか1項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of the 10-13, wherein the light emission is white.

15. 15. 前記10〜14のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする表示装置。 Display device characterized by having an organic electroluminescent element of any one of the above 10 to 14.

16. 16. 前記10〜14のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする照明装置。 Lighting apparatus characterized by having an organic electroluminescent element of any one of the above 10 to 14.

本発明の有機エレクトロルミネッセンス素子材料により、高い発光輝度を示し、且つ半減寿命の長い有機エレクトロルミネッセンス素子、及び該素子を用いた照明装置、表示装置を提供することができた。 The organic electroluminescence element material of the present invention show a high luminance, and a long organic electroluminescent device half-life, and a lighting device using the element, it is possible to provide a display device.

以下、本発明を詳細に説明する。 The present invention will be described in detail.

本発明者等は、鋭意検討の結果、前記一般式(1)〜(7)で表される構造を置換基として分子内に有する化合物を少なくとも1種用いることにより、高い発光輝度を示し、且つ半減寿命の長い有機EL素子、及び該有機EL素子を有する照明装置、表示装置を提供できることを見いだした。 The present inventors have conducted intensive result of examination, by using at least one compound having the general formula (1) to (7) represented by the molecular structure as a substituent group, a high luminance, and long organic EL device half-life, and a lighting apparatus having the organic EL device was found to be able to provide a display device. 併せて、上記の化合物を組み合わせることにより、高効率なフルカラー画像表示装置が得られることが判った。 In addition, by combining the above compounds, it was found that high-efficiency full-color image display device can be obtained.

本発明の有機EL素子とは、該有機EL素子を構成する少なくとも一つの層に、前記一般式(1)〜(7)で表される構造を置換基として分子内に有する化合物の少なくとも1種を含有することが、本発明に記載の効果を得るための必須要件であるが、好ましくは上記の化合物を発光層、または正孔阻止層に含有せしめることである。 The organic EL device of the present invention, at least one layer constituting the organic EL device, at least one of the general formulas (1) to (7) a compound having a structure represented by the intramolecular as a substituent to contain is is a prerequisite for obtaining the effects described in the present invention, preferably to allowed to contain the above-mentioned compound in the light emitting layer, or a hole blocking layer.

カルバゾール誘導体は、リン光性有機EL素子の発光ホストとして効率や寿命の面で優れた性能を示す。 Carbazole derivatives exhibit excellent performance in terms of efficiency and life as a light emitting host of phosphorescent organic EL device. 我々はこの特性を更に向上させるために、種々の置換基を導入して改良を検討した。 To further improve this property was studied improved by introducing various substituents. その結果、本発明で開示した前記一般式(1)〜(7)で表される構造を置換基として分子内に有する化合物を有機EL素子材料の発光ホストとして評価した結果、発光効率、及び発光寿命の改善効果が認められた。 As a result, a result of a compound having in the molecule the structure represented by the general formula disclosed in the present invention (1) to (7) as a substituent and rated as a light emitting host of an organic EL device material, luminous efficiency, and emission improvement of life was observed. 更に、カルバゾール誘導体以外の母核を有する化合物へも適用したところ、同様な改善効果が得られることが見出された。 Furthermore, was also applied to a compound having a nucleus other than a carbazole derivative, it has been found that the same improvement effect is obtained.

また、前記一般式(1)〜(7)で表される構造は複素環の一種であることから、この構造の導入により電位が下がるため、正孔阻止層への適用も期待できる。 The structure represented by the general formula (1) to (7) since it is a kind of heterocyclic, since the potential is lowered by the introduction of this structure, even application to the hole blocking layer can be expected. 実際に、本発明で開示した前記一般式(1)〜(7)で表される構造を置換基として分子内に有する化合物を有機EL素子材料の正孔阻止材料として評価した結果、発光ホストとして使用した場合と同様の改善効果が得られることが見出された。 Indeed, the general formula (1) Results of evaluation - a compound having in the molecule the structure represented as a substituent (7) as a hole blocking material of an organic EL device material disclosed in the present invention, as a light emitting host it has been found that the same improvement effect and when used is obtained.

本発明に係る一般式(1)〜(7)で表される構造を置換基として分子内に有する化合物は、一般式(1)〜(7)で表される構造の置換基と後述する中心骨格とを結合した構造である。 A compound having a structure represented by the intramolecular as substituents in the general formula according to the present invention (1) to (7), the general formula (1) center, which will be described later with a substituent having a structure represented by - (7) a structure in which combines the skeleton.

前記一般式(1)において、Xaは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。 In Formula (1), Xa represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom. 1 、Z 2は芳香族炭化水素環または芳香族複素環を表すが、いずれか一方は芳香族複素環である。 Z 1, Z 2 represents an aromatic hydrocarbon ring or aromatic heterocyclic ring, either one is an aromatic heterocyclic ring. 3は2価の連結基または単なる結合手を表す。 Z 3 represents a divalent linking group or a single bond.

1 、Z 2が表す芳香族炭化水素環は、具体的にはベンゼン環、ナフタレン環、アントラセン環、フェナントレン環、トリフェニレン環、ペリレン環等が挙げられる。 Aromatic hydrocarbon ring represented by Z 1, Z 2 are, specifically a benzene ring, a naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, a perylene ring, and the like. 更に該芳香族炭化水素環基は、例えば、下記Gで説明する置換基によって置換されていてもよく、更に縮合環(例えば、9−フェナントリルに炭化水素環を縮合させた9−ピレニル環、ベンゼン環に複素環を縮合させた8−キノリル環等)を形成してもよい。 Further aromatic hydrocarbon ring group, for example, may be substituted by a substituent as described below G, further condensed rings (e.g., 9-pyrenyl ring by condensation of hydrocarbon ring 9-phenanthryl, benzene ring heterocyclic ring may form a 8-quinolyl ring) which by condensing.

1 、Z 2が表す芳香族複素環は、具体的には、ピリジン環、ピリミジン環、ピリダジン環、イソオキサゾリン環、イソチアゾリン環、ピラゾリン環、ピロール環、フラン環、チオフェン環等が挙げられる。 Heteroaromatic ring Z 1, Z 2 represents, specifically, a pyridine ring, a pyrimidine ring, a pyridazine ring, isoxazoline ring, isothiazoline ring, pyrazoline ring, a pyrrole ring, a furan ring and a thiophene ring. 更に該芳香族複素環は、例えば、置換基によって置換されていてもよく、更に縮合環を形成してもよい。 Further aromatic heterocycle, for example, may be substituted by a substituent, it may further form a condensed ring.

置換基としては、アルキル基(例えば、メチル基、エチル基、プロピル基、イソプロピル基、t−ブチル基、ペンチル基、ヘキシル基、オクチル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基等)、シクロアルキル基(例えば、シクロペンチル基、シクロヘキシル基等)、アルケニル基(例えば、ビニル基、アリル基等)、アルキニル基(例えば、エチニル基、プロパルギル基等)、アリール基(例えば、フェニル基、キシリル基、メシチル基等)、ヘテロアリール基(例えば、フリル基、チエニル基、ピリジル基、ピリダジル基、ピリミジル基、ピラジル基、トリアジル基、イミダゾリル基、ピラゾリル基、チアゾリル基、キナゾリル基、フタラジル基、カルバゾリル基、ジベンゾフリル基等)、ヘテロ環基(例えば、 Examples of the substituent include an alkyl group (e.g., methyl group, an ethyl group, a propyl group, an isopropyl group, t- butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group, tridecyl group, tetradecyl group, etc. pentadecyl group), cycloalkyl group (e.g., cyclopentyl, cyclohexyl), an alkenyl group (e.g., vinyl group, allyl group, etc.), an alkynyl group (e.g., ethynyl group, propargyl group), an aryl group (e.g., phenyl group, xylyl group , mesityl group, etc.), a heteroaryl group (e.g., furyl group, a thienyl group, a pyridyl group, pyridazinyl group, pyrimidyl group, pyrazinyl group, a triazyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, quinazolyl group, a phthalazyl group, a carbazolyl group , dibenzofuryl group), a Hajime Tamaki (e.g., ロリジル基、イミダゾリジル基、モルホリル基、オキサゾリジル基等)、アルコキシ基(例えば、メトキシ基、エトキシ基、プロピルオキシ基、ペンチルオキシ基、ヘキシルオキシ基、オクチルオキシ基、ドデシルオキシ基等)、シクロアルコキシ基(例えば、シクロペンチルオキシ基、シクロヘキシルオキシ基等)、アリールオキシ基(例えば、フェノキシ基、ナフチルオキシ基等)、アルキルチオ基(例えば、メチルチオ基、エチルチオ基、プロピルチオ基、ペンチルチオ基、ヘキシルチオ基、オクチルチオ基、ドデシルチオ基等)、シクロアルキルチオ基(例えば、シクロペンチルチオ基、シクロヘキシルチオ基等)、アリールチオ基(例えば、フェニルチオ基、ナフチルチオ基等)、アルコキシカルボニル基(例えば、メチルオキ Rorijiru group, imidazolidyl group, morpholyl group, oxazolidyl group), an alkoxy group (e.g., methoxy group, ethoxy group, propyloxy group, a pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.), cycloalkoxy group (e.g., cyclopentyloxy group, cyclohexyloxy group, etc.), an aryloxy group (e.g., phenoxy group, naphthyloxy group, etc.), an alkylthio group (e.g., methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio , dodecylthio group, etc.), cycloalkylthio groups (for example, cyclopentylthio group, cyclohexylthio group, etc.), an arylthio group (e.g., phenylthio group, naphthylthio group, etc.), an alkoxycarbonyl group (e.g., Mechiruoki カルボニル基、エチルオキシカルボニル基、ブチルオキシカルボニル基、オクチルオキシカルボニル基、ドデシルオキシカルボニル基等)、アリールオキシカルボニル基(例えば、フェニルオキシカルボニル基、ナフチルオキシカルボニル基等)、スルファモイル基(例えば、アミノスルホニル基、メチルアミノスルホニル基、ジメチルアミノスルホニル基、ブチルアミノスルホニル基、ヘキシルアミノスルホニル基、シクロヘキシルアミノスルホニル基、オクチルアミノスルホニル基、ドデシルアミノスルホニル基、フェニルアミノスルホニル基、ナフチルアミノスルホニル基、2−ピリジルアミノスルホニル基等)、アシル基(例えば、アセチル基、エチルカルボニル基、プロピルカルボニル基、ペンチルカルボニル基、シクロヘキシル Carbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxy group, a dodecyl group), an aryloxycarbonyl group (e.g., phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), a sulfamoyl group (e.g., amino sulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butyl aminosulfonyl group, hexyl aminosulfonyl group, cyclohexylaminosulfonyl group, octyl aminosulfonyl group, dodecyl aminosulfonyl group, a phenyl aminosulfonyl group, naphthyl aminosulfonyl group, 2- pyridyl aminosulfonyl group), an acyl group (e.g., acetyl group, ethylcarbonyl group, propyl group, pentyl group, cyclohexyl カルボニル基、オクチルカルボニル基、2−エチルヘキシルカルボニル基、ドデシルカルボニル基、フェニルカルボニル基、ナフチルカルボニル基、ピリジルカルボニル基等)、アシルオキシ基(例えば、アセチルオキシ基、エチルカルボニルオキシ基、ブチルカルボニルオキシ基、オクチルカルボニルオキシ基、ドデシルカルボニルオキシ基、フェニルカルボニルオキシ基等)、アミド基(例えば、メチルカルボニルアミノ基、エチルカルボニルアミノ基、ジメチルカルボニルアミノ基、プロピルカルボニルアミノ基、ペンチルカルボニルアミノ基、シクロヘキシルカルボニルアミノ基、2−エチルヘキシルカルボニルアミノ基、オクチルカルボニルアミノ基、ドデシルカルボニルアミノ基、フェニルカルボニルアミノ基、ナフチルカルボ Carbonyl group, octyl group, 2-ethylhexyl group, a dodecyl group, a phenyl group, naphthyl group, pyridyl group, etc.), an acyloxy group (e.g., acetyl group, ethylcarbonyl group, butyl carbonyl group, octyl carbonyloxy group, dodecyloxy carbonyl group, a phenyl carbonyl group and the like), amide groups (e.g., methyl group, an ethylcarbonylamino group, dimethylamino carbonyl amino group, a propyl carbonyl group, pentyl carbonyl group, cyclohexyl carbonyl amino group, 2-ethylhexyl carbonylamino group, an octyl carbonylamino group, a dodecyl carbonylamino group, a phenylcarbonyl group, Nafuchirukarubo ルアミノ基等)、カルバモイル基(例えば、アミノカルボニル基、メチルアミノカルボニル基、ジメチルアミノカルボニル基、プロピルアミノカルボニル基、ペンチルアミノカルボニル基、シクロヘキシルアミノカルボニル基、オクチルアミノカルボニル基、2−エチルヘキシルアミノカルボニル基、ドデシルアミノカルボニル基、フェニルアミノカルボニル基、ナフチルアミノカルボニル基、2−ピリジルアミノカルボニル基等)、ウレイド基(例えば、メチルウレイド基、エチルウレイド基、ペンチルウレイド基、シクロヘキシルウレイド基、オクチルウレイド基、ドデシルウレイド基、フェニルウレイド基ナフチルウレイド基、2−ピリジルアミノウレイド基等)、スルフィニル基(例えば、メチルスルフィニル基、エチルスルフィ Arylamino group), a carbamoyl group (e.g., aminocarbonyl group, methylaminocarbonyl group, a dimethylaminocarbonyl group, propylamino group, pentyl amino group, cyclohexylamino group, octylaminocarbonyl group, 2-ethylhexyl amino group , dodecyl aminocarbonyl group, a phenylaminocarbonyl group, naphthyl aminocarbonyl group, 2-pyridylaminocarbonyl group), a ureido group (e.g., methylureido group, an ethylureido group, pentylureido group, a cyclohexyl ureido group, an octyl ureido group, dodecyl ureido group, a phenyl ureido group Nafuchiruureido group, 2-pyridyl-amino ureido group), a sulfinyl group (e.g., methylsulfinyl group, Echirusurufi ル基、ブチルスルフィニル基、シクロヘキシルスルフィニル基、2−エチルヘキシルスルフィニル基、ドデシルスルフィニル基、フェニルスルフィニル基、ナフチルスルフィニル基、2−ピリジルスルフィニル基等)、アルキルスルホニル基(例えば、メチルスルホニル基、エチルスルホニル基、ブチルスルホニル基、シクロヘキシルスルホニル基、2−エチルヘキシルスルホニル基、ドデシルスルホニル基等)、アリールスルホニル基(フェニルスルホニル基、ナフチルスルホニル基、2−ピリジルスルホニル基等)、アミノ基(例えば、アミノ基、エチルアミノ基、ジメチルアミノ基、ブチルアミノ基、シクロペンチルアミノ基、2−エチルヘキシルアミノ基、ドデシルアミノ基、アニリノ基、ナフチルアミノ基、2−ピリジルアミノ基 Group, butyl sulfinyl group, cyclohexyl sulfinyl group, 2-ethylhexyl sulfinyl group, dodecyl sulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridyl-sulfinyl group, etc.), an alkylsulfonyl group (e.g., methylsulfonyl group, ethylsulfonyl group , butylsulfonyl group, a cyclohexyl-sulfonyl group, 2-ethylhexyl-sulfonyl group, a dodecyl sulfonyl group), an arylsulfonyl group (phenylsulfonyl group, naphthylsulfonyl group, 2-pyridyl sulfonyl group), an amino group (e.g., amino group, ethyl amino group, dimethylamino group, butylamino group, cyclopentylamino group, a 2-ethylhexyl group, dodecyl group, an anilino group, naphthylamino group, 2-pyridylamino group 等)、ハロゲン原子(例えば、フッ素原子、塩素原子、臭素原子等)、フッ化炭化水素基(例えば、フルオロメチル基、トリフルオロメチル基、ペンタフルオロエチル基、ペンタフルオロフェニル基等)、シアノ基、ニトロ基、ヒドロキシ基、メルカプト基、シリル基(例えば、トリメチルシリル基、トリイソプロピルシリル基、トリフェニルシリル基、フェニルジエチルシリル基等)等が挙げられる。 Etc.), a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom), fluorinated hydrocarbon radicals (e.g., fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, a pentafluorophenyl group), a cyano group , nitro group, hydroxy group, a mercapto group, a silyl group (e.g., trimethylsilyl group, triisopropylsilyl group, triphenylsilyl group, a phenyl diethyl silyl group and the like) and the like.

3が表す2価の連結基としては、アルキレン、アルケニレン、アルキニレン、アリーレンなどの炭化水素基のほか、ヘテロ原子を含むものであってもよい。 Examples of the divalent linking group represented by Z 3, alkylene, alkenylene, alkynylene, other hydrocarbon group such as an arylene, may contain a heteroatom. 例えば、チオフェン−2,5−ジイル基や、ピラジン−2,3−ジイル基のような、ヘテロ芳香族化合物に由来する2価の連結基であってもよいし、酸素や硫黄などのカルコゲン原子であってもよい。 For example, thiophene-2,5-diyl group, such as pyrazine-2,3-diyl group may be a divalent linking group derived from heteroaromatic compounds, chalcogen atom such as oxygen or sulfur, it may be. また、アルキルイミノ基、ジアルキルシランジイル基やジアリールゲルマンジイル基のような、ヘテロ原子を会して連結する基であってもよい。 Further, alkylimino, such as dialkyl silane diyl group or diaryl germanium-diyl group may be a group of linked gathered heteroatoms. 3が表す単なる結合手とは、連結する置換基同士を直接結合する結合手である。 The single bond represented by Z 3, is a bond that binds to the substituent groups to each other directly linked.

本発明ではZ 3が単なる結合手であることが好ましい。 It is preferred that Z 3 is a single bond in the present invention. また、Z 1 、Z 2の少なくとも一方が六員環であることが好ましく、ともに六員環であることがより好ましい。 Further, it is preferable that at least one of Z 1, Z 2 is a six-membered ring, and more preferably both six-membered ring. これにより、より一層発光効率と高くすることができ、またより一層長寿命化させることができる。 This can be as high as more luminous efficiency, also it can be further longer life.

前記一般式(1)は、より具体的には前記一般式(2)または一般式(7)で表される。 Formula (1) is represented by the more general formula specifically (2) or the general formula (7). そして、一般式(2)は、より具体的には一般式(3)〜一般式(6)のいずれかで表される。 Then, the general formula (2) is represented by any one of the more specifically the general formula (3) to formula (6).

一般式(2)において、Xbは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。 In the general formula (2), Xb represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom. 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 、X 18は各々炭素原子または窒素原子を表すが、その少なくとも一つは窒素原子である。 X 11, X 12, X 13 , X 14, X 15, X 16, X 17, X 18 is each represents a carbon atom or a nitrogen atom, at least one of which is a nitrogen atom. 1 、R 2は各々置換基を表す。 R 1, R 2 each represents a substituent. n、mは0≦n+m≦7を満たす0から4の整数を表す。 n, m is an integer of from 0 satisfying 0 ≦ n + m ≦ 7 4. 1 、R 2が表す置換基は、一般式(1)で挙げられた置換基と同義である。 Substituents R 1, R 2 represents is the same as the substituents listed in formula (1).

一般式(3)において、Xcは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。 In the general formula (3), Xc represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom. 31 、R 32は各々置換基を表す。 R 31, R 32 each represent a substituent. n31は0から3の整数、m31は0から4の整数を表す。 n31 is an integer from 0 to 3, m31 represents an integer of 0 to 4. 31 、R 32が表す置換基は、一般式(1)で挙げられた置換基と同義である。 Substituents R 31, R 32 represents is the same as the substituents listed in formula (1).

一般式(4)において、Xdは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。 In the general formula (4), Xd represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom. 41 、R 42は各々置換基を表す。 R 41, R 42 each represent a substituent. n41は0から3の整数、m41は0から4の整数を表す。 n41 is an integer from 0 to 3, m41 represents an integer of 0 to 4. 41 、R 42が表す置換基は、一般式(1)で挙げられた置換基と同義である。 Substituents R 41, R 42 represents is the same as the substituents listed in formula (1).

一般式(5)において、Xeは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。 In the general formula (5), Xe represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom. 51 、R 52は各々置換基を表す。 R 51, R 52 each represent a substituent. n51は0から3の整数、m51は0から4の整数を表す。 n51 is an integer from 0 to 3, m51 represents an integer of 0 to 4. 51 、R 52が表す置換基は、一般式(1)で挙げられた置換基と同義である。 Substituents R 51, R 52 represents is the same as the substituents listed in formula (1).

一般式(6)において、Xfは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。 In the general formula (6), Xf represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom. 61 、R 62は各々置換基を表す。 R 61, R 62 each represent a substituent. n61は0から3の整数、m61は0から4の整数を表す。 n61 is an integer from 0 to 3, m61 represents an integer of 0 to 4. 61 、R 62が表す置換基は、一般式(1)で挙げられた置換基と同義である。 Substituents R 61, R 62 represents is the same as the substituents listed in formula (1).

一般式(7)において、Xgは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。 In the general formula (7), Xg represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom. 21 、X 22 、X 23 、X 24 、X 25 、X 26 、X 27 、X 28は各々炭素原子または窒素原子を表すが、X 21 、X 22 、X 23 、X 24の少なくとも一つ、且つX 25 、X 26 、X 27 、X 28の少なくとも一つは窒素原子である。 At least one of X 21, X 22, X 23 , X 24, X 25, X 26, X 27, X 28 is each represents a carbon atom or a nitrogen atom, X 21, X 22, X 23, X 24, and at least one of X 25, X 26, X 27 , X 28 is a nitrogen atom. 3 、R 4は各々置換基を表す。 R 3, R 4 each represents a substituent. p、qは0≦p+q≦6を満たす0から3の整数を表す。 p, q is an integer of from 0 satisfying 0 ≦ p + q ≦ 6 3. 3 、R 4が表す置換基は、一般式(1)で挙げられた置換基と同義である。 R 3, substituent R 4 represents is synonymous with the substituents mentioned in the general formula (1).

以下に、一般式(1)〜(7)で表される構造の置換基の具体例を列挙する。 Hereinafter, Specific examples of the substituent of the structure represented by the general formula (1) to (7).

中心骨格としては、以下にその具体例が挙げられる。 The central skeleton, and specific examples are listed below. なお、*は一般式(1)〜(7)で表される構造の置換基の結合点を表す。 Note that * represents the general formula (1) point of attachment for a substituent of the structure represented by - (7).

一般式(1)〜(7)で表される構造の置換基と中心骨格から形成される、本発明に係る化合物の具体例を以下に示す。 Formula (1) it is formed from substituents and the central skeleton of the structure represented by - (7), specific examples of the compounds according to the present invention are shown below.

本発明に係る上記化合物は、例えば、Organic Lettersの第7巻、23号、5241〜5244頁(2005年)に記載の参考文献等の方法を適用することにより合成できる。 The compounds of the present invention, for example, Volume 7 of Organic Letters, 23 items, can be synthesized by applying the method such references described on pages 5241-5244 (2005).

《有機EL素子材料の有機EL素子への適用》 "I applied to the organic EL element of the organic EL element material"
本発明の有機EL素子材料を用いて本発明の有機EL素子を作製する場合、有機EL素子の構成層(詳細は後述する)の中で、発光層または正孔阻止層に本発明の有機EL素子材料を用いることが好ましい。 When fabricating the organic EL device of the present invention using an organic EL device material of the present invention, among the constituent layers of the organic EL element (the details will be described later), the organic EL of the present invention to a light emitting layer or a hole blocking layer it is preferable to use a device material. また、発光層中では上記のようにホスト化合物(発光ホストともいう)として好ましく用いられる。 Further, preferably used as a host compound, as described above (also referred to as a light-emitting host) in the light-emitting layer.

(発光ホストと発光ドーパント) (Light-emitting host and the light-emitting dopant)
発光層中の主成分であるホスト化合物である発光ホストに対するリン光性化合物(発光ドーパントともいう)との混合比は、好ましくは質量で0.1〜30質量%未満の範囲に調整することである。 The mixing ratio between phosphorescent compound (also referred to as a light-emitting dopant) to the emission host is a host compound which is a main component in the light-emitting layer is preferably by adjusting to a range of less than 0.1 to 30 mass% by mass is there.

発光ドーパントは大きく分けて、蛍光を発光する蛍光性ドーパントとリン光を発光するリン光性ドーパントの2種類がある。 Emitting dopant is roughly classified into two types of phosphorescent dopants that emit fluorescent dopant and phosphorescent which emits fluorescence.

前者(蛍光性ドーパント)の代表例としては、クマリン系色素、ピラン系色素、シアニン系色素、クロコニウム系色素、スクアリウム系色素、オキソベンツアントラセン系色素、フルオレセイン系色素、ローダミン系色素、ピリリウム系色素、ペリレン系色素、スチルベン系色素、ポリチオフェン系色素、または希土類錯体系蛍光体等が挙げられる。 The former Representative examples of (fluorescent dopant), coumarin dyes, pyran based dyes, cyanine dyes, croconium dyes, squarylium dyes, oxobenzanthracene based dyes, fluorescein based dyes, rhodamine based dyes, pyrylium based dyes, perylene dyes, stilbene dyes, polythiophene dyes or rare earth complex based fluorescent material or the like, can be mentioned.

後者(リン光性ドーパント)の代表例としては、好ましくは元素周期表で8族、9族、10族の遷移金属元素を含有する錯体系化合物であり、更に好ましくはイリジウム錯体化合物、白金錯体化合物である。 Typical examples of the latter (phosphorescent dopant), Group 8 preferably in the periodic table, Group 9, a complex compound containing a transition metal element of Group 10, more preferably an iridium complex compound, a platinum complex compound it is.

具体的には以下の特許公報に記載されている化合物である。 It is specifically a compound that is described in the following patent publications.

国際公開第00/70655号パンフレット、特開2002−280178号公報、特開2001−181616号公報、特開2002−280179号公報、特開2001−181617号公報、特開2002−280180号公報、特開2001−247859号公報、特開2002−299060号公報、特開2001−313178号公報、特開2002−302671号公報、特開2001−345183号公報、特開2002−324679号公報、国際公開第02/15645号パンフレット、特開2002−332291号公報、特開2002−50484号公報、特開2002−332292号公報、特開2002−83684号公報、特表2002−540572号公報、特開2002−117978号公報、特開20 WO 00/70655 pamphlet, JP 2002-280178, JP 2001-181616, JP 2002-280179, JP 2001-181617, JP 2002-280180, JP open 2001-247859, JP 2002-299060, JP 2001-313178, JP 2002-302671, JP 2001-345183, JP 2002-324679, JP-WO 02/15645 pamphlet, JP 2002-332291, JP 2002-50484, JP 2002-332292, JP 2002-83684, JP-Kohyo 2002-540572, JP 2002- 117,978, JP 20 2−338588号公報、特開2002−170684号公報、特開2002−352960号公報、国際公開第01/93642号パンフレット、特開2002−50483号公報、特開2002−100476号公報、特開2002−173674号公報、特開2002−359082号公報、特開2002−175884号公報、特開2002−363552号公報、特開2002−184582号公報、特開2003−7469号公報、特表2002−525808号公報、特開2003−7471号公報、特表2002−525833号公報、特開2003−31366号公報、特開2002−226495号公報、特開2002−234894号公報、特開2002−235076号公報、特開2002−241751号公報 2-338588, JP 2002-170684, JP 2002-352960, JP-WO 01/93642 pamphlet, JP 2002-50483, JP 2002-100476, JP 2002 -173674, JP 2002-359082, JP 2002-175884, JP 2002-363552, JP 2002-184582, JP 2003-7469, JP-Kohyo 2002-525808 , JP 2003-7471, JP-Kohyo 2002-525833, JP 2003-31366, JP 2002-226495, JP 2002-234894 and JP Patent Application 2002-235076 , JP 2002-241751 JP 特開2001−319779号公報、特開2001−319780号公報、特開2002−62824号公報、特開2002−100474号公報、特開2002−203679号公報、特開2002−343572号公報、特開2002−203678号公報等。 JP 2001-319779, JP 2001-319780, JP 2002-62824, JP 2002-100474, JP 2002-203679, JP 2002-343572, JP Publication No. 2002-203678.

以下に、具体例の一部を示す。 Hereinafter, some of examples.

更に、下記化合物も本発明において用いられる。 Furthermore, the following compounds are also used in the present invention.

(発光ホスト) (Light-emitting host)
本発明に用いられるホスト化合物とは、発光層に含有される化合物のうちで室温(25℃)においてリン光発光のリン光量子収率が、0.01未満の化合物を表す。 The host compound used in the present invention, phosphorescence quantum yield of the phosphorescence emission at room temperature (25 ° C.) among the compounds contained in the light-emitting layer represents less than 0.01 compound.

本発明に係る化合物と併用してもよい発光ホストとしては構造的には特に制限はないが、代表的にはカルバゾール誘導体、トリアリールアミン誘導体、芳香族ボラン誘導体、含窒素複素環化合物、チオフェン誘導体、フラン誘導体、オリゴアリーレン化合物等の基本骨格を有するもの、またはカルボリン誘導体や該カルボリン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが窒素原子で置換されている環構造を有する誘導体等が挙げられる。 There is no particular limitation on the structural as may luminescent host be used in combination with the compounds of the present invention, typically carbazole derivatives, triarylamine derivatives, aromatic borane derivatives, nitrogen-containing heterocyclic compounds, thiophene derivatives , furan derivatives, those having a basic skeleton such oligoarylene compound, or a derivative having a cyclic structure in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of carboline derivatives and the carboline derivative is substituted by a nitrogen atom etc. the. 中でも、カルバゾール誘導体、カルボリン誘導体や該カルボリン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが窒素原子で置換されている環構造を有する誘導体が好ましく用いられる。 Among them, carbazole derivatives, derivatives having a cyclic structure in which at least one is substituted with a nitrogen atom of the carbon atoms of a hydrocarbon ring constituting a carboline ring of carboline derivatives and the carboline derivatives are preferably used.

以下に、本発明に係る化合物と併用してもよい発光ホストの具体例を挙げるが、本発明はこれらに限定されない。 Hereinafter, specific examples of the compound in combination with emission may host according to the present invention, the present invention is not limited thereto. これらの化合物は正孔阻止材料として使用することも好ましい。 These compounds also preferably used as a hole-blocking material.

本発明に係る発光層においては、ホスト化合物として公知のホスト化合物を複数種併用して用いてもよい。 In the light-emitting layer according to the present invention may be used in plural kinds in combination known host compound as a host compound. ホスト化合物を複数種用いることで、電荷の移動を調整することが可能であり、有機EL素子を高効率化することができる。 By using a plurality of host compounds, it is possible to control the transfer of charges can be highly efficient organic EL element. これらの公知のホスト化合物としては、正孔輸送能、電子輸送能を有しつつ、且つ発光の長波長化を防ぎ、なお且つ高Tg(ガラス転移温度)である化合物が好ましい。 These known host compound having a positive hole transporting ability and an electron transporting ability, and prevents the longer wavelength of emission, noted and having a high Tg (glass transition temperature).

また、本発明に用いられる発光ホストは低分子化合物でも、繰り返し単位をもつ高分子化合物でもよく、ビニル基やエポキシ基のような重合性基を有する低分子化合物(蒸着重合性発光ホスト)でもいい。 The light emitting host used in the present invention is also a low molecular weight compound may be a polymer compound having a repeating unit, say even low molecular compound (an evaporation polymerizing emission host) having a polymerizable group such as a vinyl group and an epoxy group .

発光ホストとしては、正孔輸送能、電子輸送能を有しつつ、且つ発光の長波長化を防ぎ、なお且つ高Tg(ガラス転移温度)である化合物が好ましい。 The light-emitting host, a hole transporting ability and an electron transporting ability, and prevents the longer wavelength of emission, noted and having a high Tg (glass transition temperature).

発光ホストの具体例としては、以下の文献に記載されている化合物が好適である。 Specific examples of the light emitting host, it is preferable compounds described in the following documents. 例えば、特開2001−257076号公報、特開2002−308855号公報、特開2001−313179号公報、特開2002−319491号公報、特開2001−357977号公報、特開2002−334786号公報、特開2002−8860号公報、特開2002−334787号公報、特開2002−15871号公報、特開2002−334788号公報、特開2002−43056号公報、特開2002−334789号公報、特開2002−75645号公報、特開2002−338579号公報、特開2002−105445号公報、特開2002−343568号公報、特開2002−141173号公報、特開2002−352957号公報、特開2002−203683号公報、特開2002−3632 For example, JP 2001-257076, JP 2002-308855, JP 2001-313179, JP 2002-319491, JP 2001-357977, JP 2002-334786, JP- JP 2002-8860, JP 2002-334787, JP 2002-15871, JP 2002-334788, JP 2002-43056, JP 2002-334789, JP 2002-75645, JP 2002-338579, JP 2002-105445, JP 2002-343568, JP 2002-141173, JP 2002-352957, JP 2002- 203683, JP 2002-3632 7号公報、特開2002−231453号公報、特開2003−3165号公報、特開2002−234888号公報、特開2003−27048号公報、特開2002−255934号公報、特開2002−260861号公報、特開2002−280183号公報、特開2002−299060号公報、特開2002−302516号公報、特開2002−305083号公報、特開2002−305084号公報、特開2002−308837号公報等。 7, JP 2002-231453, JP 2003-3165, JP 2002-234888, JP 2003-27048, JP 2002-255934, JP No. 2002-260861 , JP 2002-280183, JP 2002-299060, JP 2002-302516, JP 2002-305083, JP 2002-305084, JP 2002-308837 Patent Laid .

また、発光層はホスト化合物として更に蛍光極大波長を有するホスト化合物を含有していてもよい。 The light emitting layer may contain a host compound further having a fluorescence maximum wavelength as a host compound. この場合、他のホスト化合物とリン光性化合物から蛍光性化合物へのエネルギー移動で、有機EL素子としての電界発光は蛍光極大波長を有する他のホスト化合物からの発光も得られる。 In this case, energy transfer from other host compound and a phosphorescent compound to a fluorescent compound, an electroluminescent as an organic EL element is also obtained emission from other host compound having a fluorescence maximum wavelength. 蛍光極大波長を有するホスト化合物として好ましいのは、溶液状態で蛍光量子収率が高いものである。 Preferred as a host compound having a fluorescence maximum wavelength is a high fluorescent quantum yield in a solution state. ここで、蛍光量子収率は10%以上、特に30%以上が好ましい。 Here, the fluorescence quantum yield of 10% or more, particularly 30% or more is preferable. 具体的な蛍光極大波長を有するホスト化合物としては、クマリン系色素、ピラン系色素、シアニン系色素、クロコニウム系色素、スクアリウム系色素、オキソベンツアントラセン系色素、フルオレセイン系色素、ローダミン系色素、ピリリウム系色素、ペリレン系色素、スチルベン系色素、ポリチオフェン系色素等が挙げられる。 The host compound having a specific fluorescence maximum wavelength, coumarin dyes, pyran based dyes, cyanine dyes, croconium dyes, squarylium dyes, oxobenzanthracene based dyes, fluorescein based dyes, rhodamine based dyes, pyrylium based dyes , perylene dyes, stilbene dyes, and polythiophene dyes and the like. 蛍光量子収率は、前記第4版実験化学講座7の分光IIの362頁(1992年版、丸善)に記載の方法により測定することができる。 Fluorescence quantum yield, the fourth edition 362 pp Bunko II Jikken Kagaku Koza 7 (1992) published by Maruzen may be measured by the method described in.

次に、代表的な有機EL素子の構成について述べる。 Next, there will be described a configuration of a typical organic EL device.

《有機EL素子の構成層》 "Constituent layers of the organic EL element"
本発明の有機EL素子の構成層について説明する。 It described layers constituting the organic EL device of the present invention.

本発明の有機EL素子の層構成の好ましい具体例を以下に示すが、本発明はこれらに限定されない。 Preferred examples of the layer structure of the organic EL device of the present invention are shown below, but the invention is not limited thereto.

(i)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極 (ii)陽極/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極 (iii)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極 (iv)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極 (v)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極 (vi)陽極/陽極バッファー層/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極 (vii)陽極/陽極バッファー層/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極 《阻止層(電子阻止層、正孔阻止層)》 (I) anode / hole transport layer / luminescent layer / hole blocking layer / electron transport layer / cathode (ii) anode / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode (iii) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode (iv) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode ( v) anode / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (vi) anode / anode buffer layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode (vii) anode / anode buffer layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode "blocking layer (electron blocking layer, hole blocking layer)"
本発明に係る阻止層(例えば、電子阻止層、正孔阻止層)について説明する。 Blocking layer according to the present invention (e.g., an electron blocking layer, hole blocking layer) will be described.

本発明においては、正孔阻止層に本発明の有機EL素子材料を用いることが好ましく、特に好ましくは正孔阻止層に用いることである。 In the present invention, it is preferable to use an organic EL device material of the present invention to the hole blocking layer, particularly preferably be used for the hole blocking layer.

本発明の有機EL素子材料を正孔阻止層に含有させる場合、請求項1〜9のいずれか1項に記載されている本発明の有機EL素子材料を、正孔阻止層の層構成成分として100質量%の状態で含有させてもよいし、他の有機化合物等と混合してもよい。 Case of containing an organic EL device material of the present invention in the hole blocking layer, an organic EL device material of the present invention described in any one of claims 1 to 9, as a layer constituent of a hole blocking layer may be contained in the 100 mass% state, it may be mixed with other organic compounds.

本発明に係る阻止層の膜厚としては好ましくは3〜100nmであり、更に好ましくは5〜30nmである。 Preferably the thickness of the blocking layer according to the present invention is 3 to 100 nm, more preferably from 5 to 30 nm.

《正孔阻止層》 "Hole blocking layer"
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。 Has the function of the electron transporting layer in a broad sense, a hole blocking layer, while having a function of transporting electrons made very small material capable of transporting holes, blocking holes while transporting electrons it is possible to improve the probability of recombination of electrons and holes by.

《電子阻止層》 "Electron blocking layer"
一方、電子阻止層とは広い意味では正孔輸送層の機能を有し、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料からなり、正孔を輸送しつつ電子を阻止することで電子と正孔の再結合確率を向上させることができる。 On the other hand, has the functions of hole transport layer in a broad sense, the electron blocking layer, the ability to transport electrons while having a function of transporting holes but a very small material, an electron while transporting holes it is possible to improve the probability of recombination of electrons and holes by inhibiting. また、後述する正孔輸送層の構成を必要に応じて電子阻止層として用いることができる。 Furthermore, it can be used as the electron blocking layer optionally the structure of a positive hole transport layer described later.

《正孔輸送層》 "Hole transport layer"
正孔輸送層とは正孔を輸送する機能を有する材料を含み、広い意味で正孔注入層、電子阻止層も正孔輸送層に含まれる。 Comprise a material having a function of transporting holes from the hole transport layer, a hole injection layer in a broad sense, an electron blocking layer are included in the hole transport layer. 正孔輸送層は単層もしくは複数層設けることができる。 The hole transport layer may be a single layer or plural layers.

正孔輸送材料としては特に制限はなく、従来、光導伝材料において正孔の電荷注入輸送材料として慣用されているものや、有機EL素子の正孔注入層、正孔輸送層に使用される公知のものの中から任意のものを選択して用いることができる。 There are no particular limitations on the hole-transporting material, known materials, objects or which are conventionally used as the charge injection transport material of the hole in Hikarishirubeden material, the hole injection layer of the organic EL element, is used in the hole transporting layer it can be used to select any one from among those.

正孔輸送材料は正孔の注入もしくは輸送、電子の障壁性のいずれかを有するものであり、有機物、無機物のいずれであってもよい。 The hole transport material of the hole injection or transport, which has any of the electron barrier property, organic matter may be any of inorganic substance. 例えば、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体及びピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチリルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、アニリン系共重合体、また導電性高分子オリゴマー、特にチオフェンオリゴマー等が挙げられる。 For example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymer, and an electroconductive oligomer, particularly a thiophene oligomer.

正孔輸送材料としては上記のものを使用することができるが、ポルフィリン化合物、芳香族第三級アミン化合物及びスチリルアミン化合物、特に芳香族第三級アミン化合物を用いることが好ましい。 As a positive hole-transporting materials can be used those described above, porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, it is particularly preferable to use an aromatic tertiary amine compound.

芳香族第三級アミン化合物及びスチリルアミン化合物の代表例としては、N,N,N′,N′−テトラフェニル−4,4′−ジアミノフェニル;N,N′−ジフェニル−N,N′−ビス(3−メチルフェニル)−〔1,1′−ビフェニル〕−4,4′−ジアミン(TPD);2,2−ビス(4−ジ−p−トリルアミノフェニル)プロパン;1,1−ビス(4−ジ−p−トリルアミノフェニル)シクロヘキサン;N,N,N′,N′−テトラ−p−トリル−4,4′−ジアミノビフェニル;1,1−ビス(4−ジ−p−トリルアミノフェニル)−4−フェニルシクロヘキサン;ビス(4−ジメチルアミノ−2−メチルフェニル)フェニルメタン;ビス(4−ジ−p−トリルアミノフェニル)フェニルメタン;N,N′−ジフェニル−N,N′− Aromatic Representative examples of tertiary amine compounds and styrylamine compounds, N, N, N ', N'- tetraphenyl-4,4'-diaminophenyl; N, N'-diphenyl -N, N' bis (3-methylphenyl) - [1,1'-biphenyl] -4,4'-diamine (TPD); 2,2-bis (4-di -p- tolyl-aminophenyl) propane; 1,1-bis (4-di -p- tolyl-aminophenyl) cyclohexane; N, N, N ', N'- tetra -p- tolyl-4,4'-diaminobiphenyl; 1,1-bis (4-di -p- tolyl aminophenyl) -4-phenyl cyclohexane; bis (4-dimethylamino-2-methylphenyl) phenyl methane, bis (4-di -p- tolyl-aminophenyl) phenyl methane; N, N'-diphenyl -N, N ' - (4−メトキシフェニル)−4,4′−ジアミノビフェニル;N,N,N′,N′−テトラフェニル−4,4′−ジアミノジフェニルエーテル;4,4′−ビス(ジフェニルアミノ)クオードリフェニル;N,N,N−トリ(p−トリル)アミン;4−(ジ−p−トリルアミノ)−4′−〔4−(ジ−p−トリルアミノ)スチリル〕スチルベン;4−N,N−ジフェニルアミノ−(2−ジフェニルビニル)ベンゼン;3−メトキシ−4'−N,N−ジフェニルアミノスチルベンゼン;N−フェニルカルバゾール、更には米国特許第5,061,569号明細書に記載されている2個の縮合芳香族環を分子内に有するもの、例えば、4,4′−ビス〔N−(1−ナフチル)−N−フェニルアミノ〕ビフェニル(NPD)、特開平4−30868 (4-methoxyphenyl) -4,4'-diaminobiphenyl; N, N, N ', N'- tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis (diphenylamino) click Audrey phenyl; N, N, N-tri (p- tolyl) amine; 4- (di -p- tolylamino) -4 '- [4- (di -p- tolylamino) styryl] stilbene; 4-N, N-diphenylamino - (2-diphenylvinyl) benzene; 3-methoxy--4'N, N-diphenylamino stilbene; N- phenyl carbazole, even the two that are described in U.S. Patent No. 5,061,569 those having a condensed aromatic ring in the molecule, for example, 4,4'-bis [N-(1-naphthyl) -N- phenylamino] biphenyl (NPD), JP-a-4-30868 号公報に記載されているトリフェニルアミンユニットが3つスターバースト型に連結された4,4′,4′−トリス〔N−(3−メチルフェニル)−N−フェニルアミノ〕トリフェニルアミン(MTDATA)等が挙げられる。 Triphenylamine units disclosed in JP is coupled to the three starburst 4,4 ', 4'-tris [N- (3- methylphenyl) -N- phenylamino] triphenylamine (MTDATA ), and the like.

更にこれらの材料を高分子鎖に導入した、またはこれらの材料を高分子の主鎖とした高分子材料を用いることもできる。 Furthermore it is also possible to use these materials are introduced in a polymer chain or a polymer having the material as the polymer main chain. また、p型−Si、p型−SiC等の無機化合物も正孔注入材料、正孔輸送材料として使用することができる。 Further, it is possible to p-type -Si, inorganic compounds such as p-type -SiC used hole injection material, a hole transport material.

この正孔輸送層は上記正孔輸送材料を、例えば、真空蒸着法、スピンコート法、キャスト法、インクジェット法、LB法等の公知の方法により、薄膜化することにより形成することができる。 The hole transport layer is the hole transport material, for example, vacuum deposition, spin coating, casting method, an ink jet method, by a known method LB method, can be formed by thinning. 正孔輸送層の膜厚については特に制限はないが、通常は5〜5000nm程度である。 No particular limitation is imposed on the thickness of the hole transport layer but, usually, about 5 to 5000 nm. この正孔輸送層は上記材料の一種または二種以上からなる一層構造であってもよい。 The hole transport layer may have a single layer structure made of one or two or more of the above materials.

《電子輸送層》 "Electron transport layer"
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入層、正孔阻止層も電子輸送層に含まれる。 Made of a material having a function of transporting electrons from the electron transporting layer, an electron injection layer in a broad sense, a hole blocking layer are included in an electron transport layer. 電子輸送層は単層もしくは複数層を設けることができる。 The electron transport layer may be provided as a single layer or plural layers.

従来、単層の電子輸送層、及び複数層とする場合は発光層に対して陰極側に隣接する電子輸送層に用いられる電子輸送材料(正孔阻止材料を兼ねる)としては、下記の材料が知られている。 Conventionally, an electron-transporting layer of a single layer, and if a plurality of layers as an electron transporting material for the electron transport layer adjacent to the cathode side of the light-emitting layer (also serving as a hole blocking material), the following materials Are known.

更に、電子輸送層は陰極より注入された電子を発光層に伝達する機能を有していればよく、その材料としては従来公知の化合物の中から任意のものを選択して用いることができる。 Furthermore, the electron-transporting layer may have a function of transporting electrons injected from the cathode to the light-emitting layer, as a material thereof may be used optionally selected from known compounds.

この電子輸送層に用いられる材料(以下、電子輸送材料という)の例としては、ニトロ置換フルオレン誘導体、ジフェニルキノン誘導体、チオピランジオキシド誘導体、ナフタレンペリレン等の複素環テトラカルボン酸無水物、カルボジイミド、フレオレニリデンメタン誘導体、アントラキノジメタン及びアントロン誘導体、オキサジアゾール誘導体、カルボリン誘導体、または該カルボリン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが窒素原子で置換されている環構造を有する誘導体等が挙げられる。 The material for the electron-transporting layer (hereinafter, referred to as an electron transporting material) Examples of a nitro-substituted fluorene derivatives, diphenyl derivatives, thiopyran dioxide derivatives, heterocyclic tetracarboxylic anhydride such as naphthalene perylene, carbodiimide, deflection distyrylpyrazine derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, carboline derivatives or ring in which at least one carbon atom of a hydrocarbon ring constituting a carboline ring of the carboline derivative is substituted by a nitrogen atom, derivative having the structure. 更に上記オキサジアゾール誘導体において、オキサジアゾール環の酸素原子を硫黄原子に置換したチアジアゾール誘導体、電子吸引性基として知られているキノキサリン環を有するキノキサリン誘導体も電子輸送材料として用いることができる。 Furthermore, in the above oxadiazole derivatives, may be used an oxygen atom in the oxadiazole ring of thiadiazole derivative substituted by a sulfur atom, a quinoxaline derivative also electron-transporting material having a quinoxaline ring known as an electron withdrawing group.

更にこれらの材料を高分子鎖に導入した、またはこれらの材料を高分子の主鎖とした高分子材料を用いることもできる。 Furthermore it is also possible to use these materials are introduced in a polymer chain or a polymer having the material as the polymer main chain.

また8−キノリノール誘導体の金属錯体、例えば、トリス(8−キノリノール)アルミニウム(Alq)、トリス(5,7−ジクロロ−8−キノリノール)アルミニウム、トリス(5,7−ジブロモ−8−キノリノール)アルミニウム、トリス(2−メチル−8−キノリノール)アルミニウム、トリス(5−メチル−8−キノリノール)アルミニウム、ビス(8−キノリノール)亜鉛(Znq)等、及びこれらの金属錯体の中心金属がIn、Mg、Cu、Ca、Sn、GaまたはPbに置き替わった金属錯体も電子輸送材料として用いることができる。 The metal complexes of 8-quinolinol derivatives, such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc., and the central metal of these metal complexes is an in, Mg, Cu can Ca, Sn, even Ga or Pb is used as an electron transport material. その他、メタルフリーもしくはメタルフタロシアニン、またはそれらの末端がアルキル基やスルホン酸基等で置換されているものも電子輸送材料として好ましく用いることができる。 Other, it can be preferably used as the electron transport material also those metal-free or metal phthalocyanine, or their ends are substituted with an alkyl group and a sulfonic acid group. また、発光層の材料として例示したジスチリルピラジン誘導体も、電子輸送材料として用いることができるし、正孔注入層、正孔輸送層と同様にn型−Si、n型−SiC等の無機半導体も電子輸送材料として用いることができる。 Further, distyryl pyrazine derivative exemplified as a material for the light emitting layer may preferably be used as the electron transporting material, a hole injection layer, n-type -Si like the hole transport layer, an inorganic semiconductor such as n-type -SiC it can be used as the electron transporting material.

この電子輸送層は上記電子輸送材料を、例えば、真空蒸着法、スピンコート法、キャスト法、インクジェット法、LB法等の公知の方法により、薄膜化することにより形成することができる。 The electron transport layer is the electron transport material, for example, vacuum deposition, spin coating, casting method, an ink jet method, by a known method LB method, can be formed by thinning. 電子輸送層の膜厚については特に制限はないが、通常は5〜5000nm程度である。 There is no particular limitation on the thickness of the electron transport layer generally is about 5 to 5000 nm. この電子輸送層は上記材料の一種または二種以上からなる一層構造であってもよい。 The electron transport layer may have a single layer structure made of one or two or more of the above materials.

次に、本発明の有機EL素子の構成層として用いられる注入層について説明する。 Next, a description will be given injection layer used as a constituent layer of the organic EL device of the present invention.

《注入層》:電子注入層、正孔注入層 注入層は必要に応じて設け、電子注入層と正孔注入層があり、上記のごとく陽極と発光層または正孔輸送層の間、及び陰極と発光層または電子輸送層との間に存在させてもよい。 "Injection layer": the electron injection layer, provided if the hole injection layer injecting layer need, there is an electron injection layer and the hole injection layer, between the as the anode luminescent layer or a hole transport layer, and a cathode it may be present between the light-emitting layer or an electron transport layer.

注入層とは駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、「有機EL素子とその工業化最前線(1998年11月30日 エヌ・ティー・エス社発行)」の第2編第2章「電極材料」(123〜166頁)に詳細に記載されており、正孔注入層(陽極バッファー層)と電子注入層(陰極バッファー層)とがある。 An injection layer is a layer which is arranged between an electrode and an organic layer to decrease an operating voltage and emission brightness enhancement, "Organic EL element and its Industrialization Front (Nov. 30, 1998 issued from NTS Inc.) 2 Chapter 2 of "is described in detail in" electrode material "(page 123 to 166), there is a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).

陽極バッファー層(正孔注入層)は特開平9−45479号、同9−260062号、同8−288069号の各公報等にもその詳細が記載されており、具体例として、銅フタロシアニンに代表されるフタロシアニンバッファー層、酸化バナジウムに代表される酸化物バッファー層、アモルファスカーボンバッファー層、ポリアニリン(エメラルディン)やポリチオフェン等の導電性高分子を用いた高分子バッファー層等が挙げられる。 Anode buffer layer (hole injection layer) JP 9-45479, the 9-260062 Patent describes a also detailed in the Publication of Nos. 8-288069, as a specific example, represented by copper phthalocyanine a phthalocyanine buffer layer is an oxide buffer layer represented by a vanadium oxide, an amorphous carbon buffer layer, polyaniline (emeraldine) and a polymer buffer layer employing an electroconductive polymer such as polythiophene.

陰極バッファー層(電子注入層)は特開平6−325871号、同9−17574号、同10−74586号の各公報等にもその詳細が記載されており、具体的にはストロンチウムやアルミニウム等に代表される金属バッファー層、フッ化リチウムに代表されるアルカリ金属化合物バッファー層、フッ化マグネシウムに代表されるアルカリ土類金属化合物バッファー層、酸化アルミニウムに代表される酸化物バッファー層等が挙げられる。 Cathode buffer layer (electron injection layer) JP-6-325871, the 9-17574 JP, in the Publication of Nos. 10-74586 describes a the details, in particular in the strontium or aluminum a metal buffer layer represented by an alkali metal compound buffer layer represented by lithium fluoride, an alkaline earth metal compound buffer layer represented by magnesium fluoride and an oxide buffer layer represented by aluminum oxide.

上記バッファー層(注入層)はごく薄い膜であることが望ましく、素材にもよるがその膜厚は0.1〜100nmの範囲が好ましい。 The buffer layer (injecting layer) is preferably a very thin film, although it depends on the material thickness thereof in the range of 0.1~100nm is preferred.

この注入層は上記材料を、例えば、真空蒸着法、スピンコート法、キャスト法、インクジェット法、LB法等の公知の方法により、薄膜化することにより形成することができる。 The injection layer is the material, for example, vacuum deposition, spin coating, casting method, an ink jet method, by a known method LB method, can be formed by thinning. 注入層の膜厚については特に制限はないが、通常は5〜5000nm程度である。 No particular limitation is imposed on the thickness of the injection layer, but usually is about 5 to 5000 nm. この注入層は上記材料の一種または二種以上からなる一層構造であってもよい。 The injection layer may have a single layer structure made of one or two or more of the above materials.

《陽極》 "anode"
本発明の有機EL素子に係る陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。 The anode of the organic EL device of the present invention, a large work function (4 eV or more) metals, an alloy, is preferably used a conductive compound and a mixture thereof as an electrode material. このような電極物質の具体例としては、Au等の金属、CuI、インジウムチンオキシド(ITO)、SnO 2 、ZnO等の導電性透明材料が挙げられる。 Specific examples of such an electrode material, metals such as Au, CuI, indium tin oxide (ITO), a conductive transparent material SnO 2, ZnO and the like. また、IDIXO(In 23 −ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。 It may also be used IDIXO (In 2 O 3 -ZnO) spruce amorphous in can prepare a transparent conductive film material.

陽極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。 Anode to form a thin film by a method such as vapor deposition or sputtering of the electrode material, if not desired shape pattern may be formed of, or pattern accuracy requires less by photolithography (degree or 100 [mu] m) , a pattern may be formed through a mask of a desired form at the time of depositing or spattering of the electrode material. この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。 When light is emitted through the anode, the transmittance is preferably set to not greater than 10%, the sheet resistance as an anode is preferably several hundreds Omega / □ or less. 更に膜厚は材料にもよるが、通常10〜1000nm、好ましくは10〜200nmの範囲で選ばれる。 Further, although the layer thickness depends on the material, usually 10 to 1000 nm, preferably chosen in the range of 10 to 200 nm.

《陰極》 "cathode"
一方、本発明に係る陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。 On the other hand, as a cathode according to the present invention, a small work function (also referred to as an electron injecting metal) (4 eV or less) metal, alloy, and an electroconductive compound, or a mixture thereof is used as the electrode material. このような電極物質の具体例としては、ナトリウム、ナトリウム−カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al 23 )混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。 Specific examples of the electrode substance include sodium, sodium - potassium alloy, magnesium, lithium, magnesium / copper mixture, a magnesium / silver mixture, a magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3) mixture, indium, a lithium / aluminum mixture, and rare earth metals. これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al 23 )混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。 Among these, from the viewpoint of electron injection property and durability against oxidation or the like, a mixture of a second metal values ​​of the electron injection metal and a work function than this is the large stable metal, such as magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3) mixture, lithium / aluminum mixture, and aluminum.

陰極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させることにより作製することができる。 Cathode can be prepared by the method such as evaporation or spattering of the electrode material to form a thin film. また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10〜1000nm、好ましくは50〜200nmの範囲で選ばれる。 The sheet resistance is preferably several hundreds Omega / □ or less of the cathode, the layer thickness is generally 10 to 1000 nm, is preferably selected in the range of 50 to 200 nm. なお発光を透過させるため、有機EL素子の陽極または陰極のいずれか一方が透明または半透明であれば、発光輝度が向上し好都合である。 Note to transmit emission, either one of an anode or a cathode of the organic EL element is transparent or translucent, it is advantageous to improve emission luminance.

《基体(基板、基材、支持体等ともいう)》 "Substrate (substrate, the substrate, also referred to as a support, or the like)"
本発明の有機EL素子に係る基体としては、ガラス、プラスチック等の種類には特に限定はなく、また透明のものであれば特に制限はないが、好ましく用いられる基板としては、例えば、ガラス、石英、光透過性樹脂フィルムを挙げることができる。 As the substrate according to the organic EL device of the present invention, the glass is not particularly limited to a type of plastic, also it is not particularly limited as long as the transparent, the substrate preferably used include glass, quartz , mention may be made of a light transmissive resin film. 特に好ましい基体は、有機EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。 Particularly preferred is a resin film capable of providing flexibility to the organic EL element.

樹脂フィルムとしては、例えば、ポリエチレンテレフタレート(PET)、ポリエチレンナフタレート(PEN)、ポリエーテルスルホン(PES)、ポリエーテルイミド、ポリエーテルエーテルケトン、ポリフェニレンスルフィド、ポリアリレート、ポリイミド、ポリカーボネート(PC)、セルローストリアセテート(TAC)、セルロースアセテートプロピオネート(CAP)等からなるフィルム等が挙げられる。 As the resin film, for example, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyetherimide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), a film and the like made of cellulose acetate propionate (CAP) and the like.

樹脂フィルムの表面には、無機物もしくは有機物の被膜またはその両者のハイブリッド被膜が形成されていてもよく、水蒸気透過率が0.01g/m 2・day以下の高バリア性フィルムであることが好ましい。 The surface of the resin film may be a hybrid coating of inorganic or organic coating or both has been formed, it is preferable water vapor permeability is high barrier film follows 0.01g / m 2 · day.

本発明の有機EL素子の発光の室温における外部取り出し効率は、1%以上であることが好ましく、より好ましくは2%以上である。 External extraction efficiency of light emission at room temperature of the organic EL device of the present invention is preferably at least 1%, more preferably not less than 2%. ここに、外部取り出し量子効率(%)=有機EL素子外部に発光した光子数/有機EL素子に流した電子数×100である。 Here, the external extraction quantum efficiency (%) = number of electrons × 100 was flowed to the number of photons / organic EL device emitting organic EL device the outside.

また、カラーフィルター等の色相改良フィルター等を併用してもよい。 It may be used in combination hue improving filter such as a color filter.

照明用途で用いる場合には、発光ムラを低減させるために粗面加工したフィルム(アンチグレアフィルム等)を併用することもできる。 When used in lighting applications, it may be used in combination roughened films (anti-glare film or the like) in order to reduce the unevenness of light emission.

多色表示装置として用いる場合は、少なくとも2種類の異なる発光極大波長を有する有機EL素子からなるが、有機EL素子を作製する好適な例を説明する。 When used as a multicolor display apparatus, it consists of an organic EL element having at least two different emission maximum wavelength, illustrating a preferred example of manufacturing an organic EL element.

《有機EL素子の作製方法》 "Method for manufacturing the organic EL element"
本発明の有機EL素子の作製方法の一例として、陽極/正孔注入層/正孔輸送層/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極からなる有機EL素子の作製法について説明する。 As an example of a method for manufacturing an organic EL device of the present invention, an anode / hole injection layer / hole transport layer / luminescent layer / hole blocking layer / electron transport layer / cathode buffer layer / preparation method of the organic EL device comprising a cathode It will be described.

まず適当な基体上に所望の電極物質、例えば、陽極用物質からなる薄膜を1μm以下、好ましくは10〜200nmの膜厚になるように、蒸着やスパッタリング等の方法により形成させ、陽極を作製する。 Desired electrode material on a first suitable substrate, e.g., below 1μm, a thin film made of an anode substance, preferably to have a thickness of 10 to 200 nm, it is formed by a method such as vapor deposition or sputtering, to prepare an anode . 次に、この上に素子材料である正孔注入層、正孔輸送層、発光層、正孔阻止層、電子輸送層等の有機化合物を含有する薄膜を形成させる。 Next, a hole injection layer, which is a device material on the hole transporting layer, light emitting layer, a hole blocking layer, forming a thin film containing an organic compound such as an electron-transporting layer.

この有機化合物を含有する膜の薄膜化の方法としては、スピンコート法、キャスト法、インクジェット法、蒸着法、印刷法等があるが、均質な膜が得られやすく、且つピンホールが生成しにくい等の点から真空蒸着法またはスピンコート法が特に好ましい。 As a method for thinning the film containing the organic compound, a spin coating method, a casting method, an inkjet method, an evaporation method, a printing method and the like, homogeneous film is liable to be obtained, and pinholes are not easily generated vacuum deposition or spin-coating method from the viewpoint of equal is particularly preferred. 更に層ごとに異なる製膜法を適用してもよい。 Further it may apply different film method per layer. 製膜に蒸着法を採用する場合、その蒸着条件は使用する化合物の種類等により異なるが、一般にボート加熱温度50〜450℃、真空度10 -6 〜10 -2 Pa、蒸着速度0.01〜50nm/秒、基板温度−50〜300℃、膜厚0.1〜5μmの範囲で適宜選ぶことが望ましい。 When employing the vapor deposition film, the depositing conditions thereof are varied according to kinds of materials used, generally boat temperature 50 to 450 ° C., vacuum of 10 -6 to 10 -2 Pa, deposition rate 0.01 50 nm / sec, substrate temperature -50~300 ° C., it is desirable to select appropriate thickness in the range of 0.1 to 5 [mu] m.

これらの層の形成後、その上に陰極用物質からなる薄膜を1μm以下好ましくは50〜200nmの範囲の膜厚になるように、例えば、蒸着やスパッタリング等の方法により形成させ、陰極を設けることにより所望の有機EL素子が得られる。 After formation of these layers, a thin film made of a cathode material is formed thereon as hereinafter preferably 1μm make a layer thickness in the range of 50 to 200 nm, for example, is formed by a method such as vapor deposition or sputtering, providing a cathode desired organic EL device can be obtained by. この有機EL素子の作製は、一回の真空引きで一貫して正孔注入層から陰極まで作製するのが好ましいが、途中で取り出して異なる製膜法を施しても構わない。 Preparation of the organic EL element, but may be subjected to film formation method different extraction halfway preferably made from a single consistently positive hole injection layer by vacuuming up the cathode. その際、作業を乾燥不活性ガス雰囲気下で行う等の配慮が必要となる。 At that time, the required to be carried out under a dry inert gas atmosphere.

《表示装置》 "Display device"
本発明の表示装置について説明する。 Described display device of the present invention. 本発明の表示装置は上記有機EL素子を有する。 Display device of the present invention having the above organic EL element.

本発明の表示装置は単色でも多色でもよいが、ここでは多色表示装置について説明する。 Display device of the present invention may be a multi-colored in monochrome, is described here multicolor display device. 多色表示装置の場合は発光層形成時のみシャドーマスクを設け、一面に蒸着法、キャスト法、スピンコート法、インクジェット法、印刷法等で膜を形成できる。 For multicolor display device provided with a shadow mask only at the time of forming the light emitting layer, a vapor deposition method, a casting method, a spin coating method, an inkjet method, the film can be formed by a printing method or the like.

発光層のみパターニングを行う場合、その方法に限定はないが、好ましくは蒸着法、インクジェット法、印刷法である。 If patterning is performed only the light emitting layer is not limited to this method, it is preferably an evaporation method, an inkjet method, a printing method. 蒸着法を用いる場合においては、シャドーマスクを用いたパターニングが好ましい。 In the case of using the evaporation method, patterning using a shadow mask is preferred.

また、作製順序を逆にして、陰極、電子輸送層、正孔阻止層、発光層、正孔輸送層、陽極の順に作製することも可能である。 Further, by reversing the preparation order, a cathode, an electron transport layer, a hole blocking layer, an emission layer, a hole transport layer, it is also possible to prepare the order of the anode.

このようにして得られた多色表示装置に直流電圧を印加する場合には、陽極を+、陰極を−の極性として電圧2〜40V程度を印加すると発光が観測できる。 When a DC voltage is applied to the multicolor display device obtained in this manner, an anode and +, cathode - polarity voltage of approximately 2~40V the emission can be observed applied as the. また、逆の極性で電圧を印加しても電流は流れずに発光は全く生じない。 Also, no at all emission without current flows even if a voltage is applied in reverse polarity. 更に交流電圧を印加する場合には、陽極が+、陰極が−の状態になったときのみ発光する。 Furthermore, when an AC voltage is applied, the anode +, cathode - emits light only in a state. なお、印加する交流の波形は任意でよい。 The waveform of the alternating current may be arbitrary.

多色表示装置は表示デバイス、ディスプレイ、各種発光光源として用いることができる。 Multicolor display device can be utilized as a display device, a display, or various light emission sources. 表示デバイス、ディスプレイにおいて、青、赤、緑発光の3種の有機EL素子を用いることによりフルカラーの表示が可能となる。 The display device or the display, blue, red, full color display becomes possible by using three kinds of organic EL elements of green light emission.

表示デバイス、ディスプレイとしては、テレビ、パソコン、モバイル機器、AV機器、文字放送表示、自動車内の情報表示等が挙げられる。 Display device, as a display, a television, a personal computer, a mobile device, AV equipment, a display for text broadcasting, and an information display used in a car. 特に静止画像や動画像を再生する表示装置として使用してもよく、動画再生用の表示装置として使用する場合の駆動方式は、単純マトリクス(パッシブマトリクス)方式でもアクティブマトリクス方式でもどちらでもよい。 May be used as a display device, in particular for reproducing still images and moving images, driving method when used as a display for reproducing a moving image, it may be both an active matrix mode in a simple matrix (passive matrix) method.

発光光源としては家庭用照明、車内照明、時計や液晶用のバックライト、看板広告、信号機、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙げられるが、これに限定するものではない。 Home lighting as a light emission source, interior lighting, backlight of a watch or a liquid crystal, a panel advertisement, traffic lights, light sources of optical storage medium, an electrophotographic copying machine of the light source for an optical communication device of the light source, a light source such as a light sensor including but not limited to this.

《照明装置》 "Lighting device"
本発明の照明装置について説明する。 It illustrates lighting device of the present invention. 本発明の照明装置は上記有機EL素子を有する。 Lighting apparatus of the present invention having the above organic EL element.

本発明の有機EL素子に共振器構造を持たせた有機EL素子として用いてもよく、このような共振器構造を有した有機EL素子の使用目的としては、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙げられるが、これらに限定されない。 Resonator structure to the organic EL device of the present invention may be used as the organic EL element having a, as the intended use of the organic EL element having such a resonator structure, the optical storage medium source, an electrophotographic copying machine of the light source for an optical communication device of a light source for an optical sensor include, but are not limited to. また、レーザー発振をさせることにより上記用途に使用してもよい。 It may also be used in the applications by the laser oscillation.

また、本発明の有機EL素子は照明用や露光光源のような一種のランプとして使用してもよいし、画像を投影するタイプのプロジェクション装置や、静止画像や動画像を直接視認するタイプの表示装置(ディスプレイ)として使用してもよい。 Further, the organic EL device of the present invention may be used as a type of lamps, such as illumination lamp or a light source for exposure, as a projection device for projecting an image, display type viewing the still images and moving images directly it may be used as a device (display). 動画再生用の表示装置として使用する場合の駆動方式は、単純マトリクス(パッシブマトリクス)方式でもアクティブマトリクス方式でもどちらでもよい。 Drive system when used as a display device for reproducing a moving image, it may be both an active matrix mode in a simple matrix (passive matrix) method. または、異なる発光色を有する本発明の有機EL素子を2種以上使用することにより、フルカラー表示装置を作製することが可能である。 Alternatively, the organic EL device of the present invention having different emission colors by using two or more, it is possible to produce a full color display device.

以下、本発明の有機EL素子を有する表示装置の一例を図面に基づいて説明する。 It will be described below based on an example of a display device having an organic EL device of the present invention with reference to the drawings.

図1は有機EL素子から構成される表示装置の一例を示した模式図である。 Figure 1 is a schematic diagram showing an example of a display containing an organic EL device. 有機EL素子の発光により画像情報の表示を行う、例えば、携帯電話等のディスプレイの模式図である。 For displaying image information due to light emission from the organic EL element, for example, it is a schematic view of a display such as a mobile phone.

ディスプレイ1は複数の画素を有する表示部A、画像情報に基づいて表示部Aの画像走査を行う制御部B等からなる。 Display 1 comprises a display unit A, the control unit B for performing the image scanning in the display section A based on image information having a plurality of pixels. 制御部Bは表示部Aと電気的に接続され、複数の画素それぞれに外部からの画像情報に基づいて走査信号と画像データ信号を送り、走査信号により走査線毎の画素が画像データ信号に応じて順次発光して画像走査を行って画像情報を表示部Aに表示する。 The control unit B is electrically connected to the display section A, it transmits a scanning signal and an image data signal based on image information from the outside to each of the plurality of pixels, from each pixel due to the scanning signal corresponding to the image data signal displaying the image information on the display unit a performs sequential emission to image scanning Te.

図2は表示部Aの模式図である。 Figure 2 is a schematic drawing of a display section A.

表示部Aは基板上に、複数の走査線5及びデータ線6を含む配線部と複数の画素3等とを有する。 Display unit A on the substrate, and a plurality of pixels 3 such as a wiring portion including a plurality of scanning lines 5 and the data line 6. 表示部Aの主要な部材の説明を以下に行う。 Given below a description of the main members of the display portion A.

図においては、画素3の発光した光が白矢印方向(下方向)へ取り出される場合を示している。 In figure shows a case where light emission of the pixels 3 is taken out in the direction of an arrow.

配線部の走査線5及び複数のデータ線6はそれぞれ導電材料からなり、走査線5とデータ線6は格子状に直交して、直交する位置で画素3に接続している(詳細は図示していない)。 Becomes the wiring portion of the scanning lines 5 and plural data lines 6 from the respective conductive material, the lines 5 and the lines 6 being crossed with each other at a right angle, and connected with the pixels 3 at the crossed points (shown not). 画素3は走査線5から走査信号が印加されると、データ線6から画像データ信号を受け取り、受け取った画像データに応じて発光する。 Pixel 3 when the scanning signal is applied from the scanning lines 5, receive the data signal from the data lines 6, and emit light corresponding to received image data. 発光の色が赤領域の画素、緑領域の画素、青領域の画素を適宜同一基板上に並置することによって、フルカラー表示が可能となる。 Pixel color emitting red region, pixels in the green region, side by side on suitable same substrate pixel of blue region, full-color display is possible.

次に、画素の発光プロセスを説明する。 Next, an emission process of pixels will be explained.

図3は画素の模式図である。 Figure 3 is a schematic diagram of a pixel.

画素は有機EL素子10、スイッチングトランジスタ11、駆動トランジスタ12、コンデンサ13等を備えている。 The organic EL element 10 is a pixel switching transistor 11, driving transistor 12, and a capacitor 13, and the like. 複数の画素に有機EL素子10として、赤色、緑色、青色発光の有機EL素子を用い、これらを同一基板上に並置することでフルカラー表示を行うことができる。 As the organic EL element 10 to a plurality of pixels, red, green, an organic EL element of blue emission, full color display can be performed by side by side on the same substrate.

図3において、制御部Bからデータ線6を介してスイッチングトランジスタ11のドレインに画像データ信号が印加される。 3, the image data signal is applied to the drain of the switching transistor 11 via a data line 6 from the control unit B. そして、制御部Bから走査線5を介してスイッチングトランジスタ11のゲートに走査信号が印加されると、スイッチングトランジスタ11の駆動がオンし、ドレインに印加された画像データ信号がコンデンサ13と駆動トランジスタ12のゲートに伝達される。 When the scanning signal to the gate of the switching transistor 11 is applied from the control unit B through the scanning line 5, the switching transistor 11 is switched on, the image data signal applied to the drain and the capacitor 13 driving transistor 12 It is transmitted to the gate.

画像データ信号の伝達により、コンデンサ13が画像データ信号の電位に応じて充電されるとともに、駆動トランジスタ12の駆動がオンする。 The transmission of the image data signal, the capacitor 13 is charged according to the electric potential of the image data signals, the driving transistor 12 is switched on. 駆動トランジスタ12は、ドレインが電源ライン7に接続され、ソースが有機EL素子10の電極に接続されており、ゲートに印加された画像データ信号の電位に応じて電源ライン7から有機EL素子10に電流が供給される。 Drive transistor 12 has a drain connected to the power supply line 7, the source is connected to the electrode of the organic EL element 10, the organic EL device 10 from power supply line 7 in response to the potential of the image data signal applied to the gate current is supplied.

制御部Bの順次走査により走査信号が次の走査線5に移ると、スイッチングトランジスタ11の駆動がオフする。 Progressive scanning signal by the scanning of the control unit B is to the next scanning line 5, the driving of the switching transistor 11 is turned off. しかし、スイッチングトランジスタ11の駆動がオフしてもコンデンサ13は充電された画像データ信号の電位を保持するので、駆動トランジスタ12の駆動はオン状態が保たれて、次の走査信号の印加が行われるまで有機EL素子10の発光が継続する。 However, since the drive of the switching transistor 11 is capacitor 13 is also turned off to hold the charged potential of image data signal, driving of the driving transistor 12 is kept turned on, the next application of the scanning signals is performed emission of the organic EL element 10 continues until. 順次走査により次に走査信号が印加されたとき、走査信号に同期した次の画像データ信号の電位に応じて駆動トランジスタ12が駆動して有機EL素子10が発光する。 When the next scanning signal by sequential scanning is applied, the driving transistor 12 organic EL element 10 emits light in response to the potential of the next image data signal synchronized with the scanning signal.

即ち、有機EL素子10の発光は複数の画素それぞれの有機EL素子10に対して、アクティブ素子であるスイッチングトランジスタ11と駆動トランジスタ12を設けて、複数の画素3それぞれの有機EL素子10の発光を行っている。 That is, the organic EL device 10 emitting the each of the plurality of pixels of the organic EL element 10, provided with a switching transistor 11 and driving transistor 12 which is an active element, the emission of a plurality of pixels 3 each organic EL element 10 Is going. このような発光方法をアクティブマトリクス方式と呼んでいる。 Such a light-emitting method is called an active matrix system.

ここで、有機EL素子10の発光は複数の階調電位を持つ多値の画像データ信号による複数の階調の発光でもよいし、2値の画像データ信号による所定の発光量のオン、オフでもよい。 Here, light emission of the organic EL element 10 may be emission with plural gradations according to image signal data having plural gradation potentials, or emission of on by binary image data signal in the off good. また、コンデンサ13の電位の保持は次の走査信号の印加まで継続して保持してもよいし、次の走査信号が印加される直前に放電させてもよい。 Further, the holding potential of the capacitor 13 may be continuously maintained until the next application of the scanning signal, or may be discharged immediately before the next scanning signal is applied.

本発明においては、上述したアクティブマトリクス方式に限らず、走査信号が走査されたときのみデータ信号に応じて有機EL素子を発光させるパッシブマトリクス方式の発光駆動でもよい。 In the present invention, not limited to the active matrix method as described above, it may be light emission driving a passive matrix type light emission of organic EL element according to the data signal only when the scan signal is scanned.

図4はパッシブマトリクス方式による表示装置の模式図である。 Figure 4 is a schematic drawing of a display employing a passive matrix method. 図4において、複数の走査線5と複数の画像データ線6が画素3を挟んで対向して格子状に設けられている。 4, a plurality of scanning lines 5 and the data lines 6 are provided on opposite sides of the pixel 3 in a lattice pattern.

順次走査により走査線5の走査信号が印加されたとき、印加された走査線5に接続している画素3が画像データ信号に応じて発光する。 When applied scanning signal of the scanning line 5 according to successive scanning, pixel 3 connecting to the applied scanning line 5 emits according to the image data signals.

パッシブマトリクス方式では画素3にアクティブ素子が無く、製造コストの低減が計れる。 No active element in the pixel 3 in the passive matrix method, which reduces manufacturing cost.

また、本発明の有機EL材料は照明装置として、実質白色の発光を生じる有機EL素子に適用できる。 The organic EL material of the present invention as a lighting device, can be applied to an organic EL device which emits light of substantially white. 複数の発光材料により複数の発光色を同時に発光させて混色により白色発光を得る。 Obtain white light by color mixing simultaneously emit light a plurality of emission colors by a plurality of light-emitting materials. 複数の発光色の組み合わせとしては、青色、緑色、青色の3原色の3つの発光極大波長を含有させたものでもよいし、青色と黄色、青緑と橙色等の補色の関係を利用した2つの発光極大波長を含有したものでもよい。 As a combination of the plurality of emission colors, blue, green, may be one which contains three light-emitting maximum wavelength of the blue of the three primary colors, blue and yellow, blue green and the like two utilizing complementary colors orange emission maximum wavelength may be one containing.

また、複数の発光色を得るための発光材料の組み合わせは、複数のリン光または蛍光で発光する材料を複数組み合わせたもの、蛍光またはリン光で発光する発光材料と、発光材料からの光を励起光として発光する色素材料との組み合わせたもののいずれでもよいが、本発明に係る白色有機EL素子においては、発光ドーパントを複数組み合わせ混合するだけでよい。 Also, the combination of the luminescent material for obtaining a plurality of emission colors, pumping a combination a plurality of materials that emit light in a plurality of phosphorescent or fluorescent, and luminescent material that emits light by fluorescence or phosphorescence, light from the light-emitting material it may be any of the combination of the dye material that emits a light, in the white organic EL device according to the present invention, it is a light-emitting dopant only several combinations mixed. 発光層もしくは正孔輸送層あるいは電子輸送層等の形成時のみマスクを設け、マスクにより塗り分ける等単純に配置するだけでよく、他層は共通であるのでマスク等のパターニングは不要であり、一面に蒸着法、キャスト法、スピンコート法、インクジェット法、印刷法等で、例えば、電極膜を形成でき、生産性も向上する。 The mask is provided only during the formation of such light-emitting layer or hole transporting layer or the electron transport layer need only equal simple arrangement separately applying a mask, the patterning of the mask, etc. Since the other layers are common is not necessary, one surface the vapor deposition method, a casting method, a spin coating method, an inkjet method, a printing method or the like, for example, the electrode film can be formed, thereby improving productivity. この方法によれば、複数色の発光素子をアレー状に並列配置した白色有機EL装置と異なり、素子自体が発光白色である。 According to this method, unlike the white organic EL device arranged in parallel a plurality of colors of light emitting elements in an array, the element itself is a light emitting white.

発光層に用いる発光材料としては特に制限はなく、例えば、液晶表示素子におけるバックライトであれば、CF(カラーフィルター)特性に対応した波長範囲に適合するように、本発明に係る金属錯体、また公知の発光材料の中から任意のものを選択して組み合わせて白色化すればよい。 There is no particular limitation on the light-emitting material used in the light emitting layer, for example, if the backlight in the liquid crystal display device, CF to match the wavelength range corresponding to the (color filter) characteristics, the metal complex according to the present invention, also it may be whitened combination optionally selected from the known light emitting material.

このように、本発明に係る白色発光有機EL素子は、前記表示デバイス、ディスプレイに加えて、各種発光光源、照明装置として、家庭用照明、車内照明、また露光光源のような一種のランプとして、また液晶表示装置のバックライト等、表示装置にも有用に用いられる。 Thus, white light-emitting organic EL device according to the present invention, the display device, in addition to the display, or various light emission sources, a lighting device, home lighting, as a type of lamps, such as interior lighting, also the exposure light source, the backlight of a liquid crystal display device, used in useful to a display device.

その他、時計等のバックライト、看板広告、信号機、光記憶媒体等の光源、電子写真複写機の光源、光通信処理機の光源、光センサーの光源等、更には表示装置を必要とする一般の家庭用電気器具等広い範囲の用途が挙げられる。 Other, backlight such as a watch, billboards, traffic lights, light sources, such as an optical storage medium, an electrophotographic copying machine of the light source for an optical communication device of the light source, a light source for a photo-sensor, and further the general that require display device household electrical appliances and the like include the wide range of applications.

以下、実施例により本発明を説明するが、本発明はこれらに限定されない。 The present invention will be described below by way of examples, the present invention is not limited thereto.

実施例1 Example 1
《有機EL素子1−1の作製》 "Fabrication of organic EL element 1-1"
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をiso−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。 Substrate and ITO was 150nm deposited on glass as an anode (NH Techno Glass: NA-45) after patterning, the transparent substrate having the ITO transparent electrode was subjected to ultrasonic washing with iso- propyl alcohol , dried with dry nitrogen gas and subjected to UV-ozone cleaning for 5 minutes. この透明支持基板を市販の真空蒸着装置の基板ホルダーに固定し、一方5つのタンタル製抵抗加熱ボートにα−NPD、H4、Ir−12、BAlq、Alq 3をそれぞれ入れ、真空蒸着装置(第1真空槽)に取り付けた。 Put this transparent supporting substrate was fixed to a substrate holder of a vacuum deposition apparatus available on the market, whereas five tantalum resistance heating boat α-NPD, H4, Ir- 12, BAlq, the Alq 3, respectively, a vacuum vapor deposition apparatus (a first It was attached to a vacuum chamber).

更に、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボートにアルミニウムをそれぞれ入れ、真空蒸着装置の第2真空槽に取り付けた。 Further, lithium fluoride tantalum resistance heating boat, placed respectively aluminum to tungsten resistance heating boat was attached to the second vacuum chamber of a vacuum deposition apparatus.

まず、第1の真空槽を4×10 -4 Paまで減圧した後、α−NPDの入った前記加熱ボートに通電して加熱し、蒸着速度0.1〜0.2nm/秒で透明支持基板に膜厚20nmの厚さになるように蒸着し、正孔注入/輸送層を設けた。 First, after the vacuum of the first vacuum chamber to 4 × 10 -4 Pa, and heated by supplying an electric current to the boat containing alpha-NPD, a transparent supporting substrate at a deposition rate of 0.1 to 0.2 nm / sec It was deposited to a thickness of the film thickness 20nm to, a hole injection / transport layer.

更に、H4の入った前記加熱ボートとIr−12の入ったボートをそれぞれ独立に通電して発光ホストであるH4と発光ドーパントであるIr−12の蒸着速度が100:6になるように調節し、膜厚30nmの厚さになるように蒸着し、発光層を設けた。 Moreover, the deposition rate of the H4 of containing said heating boat and Ir-12 Ir-12 of entering the boat is H4 and the light emitting dopant which is a light-emitting host energized independently is 100: of 6 as adjusted , it was deposited to a thickness of a film thickness 30 nm, which a light-emitting layer.

次いで、BAlqの入った前記加熱ボートに通電して加熱し、蒸着速度0.1〜0.2nm/秒で厚さ10nmの正孔阻止層を設けた。 Then heated by supplying an electric current to the heating boat charged with BAlq, form a hole blocking layer having a thickness of 10nm at a deposition rate of 0.1 to 0.2 nm / sec. 更にAlq 3の入った前記加熱ボートを通電して加熱し、蒸着速度0.1〜0.2nm/秒で膜厚20nmの電子輸送層を設けた。 Further heated by energizing the heating boat charged with Alq 3, an electron transporting layer having a thickness of 20nm at a deposition rate of 0.1 to 0.2 nm / sec.

次に、電子輸送層まで成膜した素子を真空のまま第2真空槽に移した後、電子輸送層の上にステンレス鋼製の長方形穴あきマスクが配置されるように装置外部からリモートコントロールして設置した。 Then, after transferring the formed elements in the second vacuum chamber while the vacuum to the electron-transporting layer, and a remote control from the outside of the apparatus as stainless steel rectangular perforated mask is placed on the electron transport layer It was installed Te.

第2真空槽を2×10 -4 Paまで減圧した後、フッ化リチウム入りのボートに通電して蒸着速度0.01〜0.02nm/秒で膜厚0.5nmの陰極バッファー層を設け、次いでアルミニウムの入ったボートに通電して、蒸着速度1〜2nm/秒で膜厚150nmの陰極をつけ、有機EL素子1−1を作製した。 After decompression of the second vacuum chamber to 2 × 10 -4 Pa, a cathode buffer layer of a thickness 0.5nm provided at a deposition rate 0.01~0.02Nm / sec by supplying an electric current to the boat of lithium fluoride-containing, then energized boat containing aluminum, with a cathode having a thickness 150nm at a deposition rate of 1 to 2 nm / sec, to produce an organic EL element 1-1.

《有機EL素子1−2〜1−16の作製》 "Fabrication of organic EL element 1-2~1-16"
有機EL素子1−1の作製において、ホスト化合物のH4を表1に記載のホスト化合物に変更した以外は同様にして、有機EL素子1−2〜1−16を作製した。 In the preparation of the organic EL element 1-1, except that H4, host compounds were changed to the host compounds listed in Table 1 in the same manner, an organic EL device was fabricated 1-2~1-16.

《有機EL素子の評価》 "Evaluation of Organic EL element"
得られた有機EL素子1−1〜1−16を評価するに際しては、作製後の各有機EL素子の非発光面をガラスケースで覆い、厚み300μmのガラス基板を封止用基板として用いて、周囲にシール材として、エポキシ系光硬化型接着剤(東亞合成社製ラックストラックLC0629B)を適用し、これを上記陰極上に重ねて前記透明支持基板と密着させ、ガラス基板側からUV光を照射して、硬化させて、封止して、図5、図6に示すような照明装置を形成して評価した。 In assessing the organic EL device 1-1 to 1-16 obtained are non-light emitting surface of the organic EL element after fabricated covered with a glass casing, using a glass substrate having a thickness of 300μm as a substrate for sealing, as a sealing material around, epoxy photocuring adhesive (manufactured by Toagosei Co., Ltd. LUX track LC0629B) was applied, which was in close contact with the transparent supporting substrate superimposed on said cathode, irradiated with UV light from the glass substrate side to, cured, sealed, 5, it was evaluated by forming the lighting device shown in FIG.

図5は照明装置の概略図を示し、有機EL素子101はガラスカバー102で覆われている(なお、ガラスカバーでの封止作業は、有機EL素子101を大気に接触させることなく窒素雰囲気下のグローブボックス(純度99.999%以上の高純度窒素ガスの雰囲気下)で行った)。 Figure 5 shows a schematic view of a lighting device, the organic EL element 101 is covered with glass cover 102 (the sealing operation of the glass cover, under a nitrogen atmosphere without the organic EL element 101 into contact with the atmosphere of the glove box was carried out (under an atmosphere of purity of 99.999% or more of the high-purity nitrogen gas)). 図6は照明装置の断面図を示し、図6において、105は陰極、106は有機EL層、107は透明電極付きガラス基板を示す。 Figure 6 shows a cross-sectional view of a lighting device, in FIG. 6, 105 cathode 106 organic EL layer, 107 denotes a glass substrate with a transparent electrode. なお、ガラスカバー102内には窒素ガス108が充填され、捕水剤109が設けられている。 Note that the glass cover 102 in a nitrogen gas 108 is filled, Tomizuzai 109 is provided.

(外部取り出し量子効率) (External extraction quantum efficiency)
有機EL素子を室温(約23〜25℃)、2.5mA/cm 2の定電流条件下による点灯を行い、点灯開始直後の発光輝度(L)[cd/m 2 ]を測定することにより、外部取り出し量子効率(η)を算出した。 The organic EL device at room temperature (about 23 to 25 ° C.), by perform lighting by constant current condition of 2.5 mA / cm 2, to measure the lighting start immediately after the emission luminance (L) [cd / m 2 ], external extraction was calculated quantum efficiency (eta). ここで、発光輝度の測定はCS−1000(コニカミノルタセンシング製)を用いた。 The measurement of emission luminance with CS-1000 (produced by Konica Minolta Sensing). 外部取り出し量子効率は有機EL素子1−1を100とする相対値で表した。 External extraction quantum efficiency was represented by a relative value to the organic EL element 1-1 and 100.

(発光寿命) (Emission lifetime)
有機EL素子を室温下、2.5mA/cm 2の定電流条件下による連続点灯を行い、初期輝度の半分の輝度になるのに要する時間(τ 1/2 )を測定した。 At room temperature the organic EL device, the continuous lighting by constant current condition of 2.5 mA / cm 2, to measure the time taken to become half of the initial luminance (τ 1/2). 発光寿命は有機EL素子1−1を100と設定する相対値で表した。 Emission lifetime was expressed by a relative value to set the organic EL element 1-1 and 100.

得られた結果を表9に示す。 The results obtained are shown in Table 9.

表9から、本発明に係る化合物を用いて作製した有機EL素子は、比較例の有機EL素子に比べ、高い発光効率と発光寿命の長寿命化が達成できることが明らかである。 Table 9, the organic EL element manufactured using the compounds according to the present invention, compared with the organic EL device of Comparative Example, it is clear that the lifetime of high luminous efficiency and emission lifetime can be achieved.

実施例2 Example 2
《有機EL素子2−1の作製》 "Fabrication of organic EL element 2-1"
陽極としてガラス上にITOを150nm成膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をiso−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。 Substrate and ITO was 150nm deposited on glass as an anode (NH Techno Glass: NA-45) after patterning, the transparent substrate having the ITO transparent electrode was subjected to ultrasonic washing with iso- propyl alcohol , dried with dry nitrogen gas and subjected to UV-ozone cleaning for 5 minutes. この透明支持基板を市販の真空蒸着装置の基板ホルダーに固定し、一方5つのタンタル製抵抗加熱ボートにα−NPD、H4、Ir−1、BAlq、Alq 3をそれぞれ入れ、真空蒸着装置(第1真空槽)に取り付けた。 Put this transparent supporting substrate was fixed to a substrate holder of a vacuum deposition apparatus available on the market, whereas five tantalum resistance heating boat α-NPD, H4, Ir- 1, BAlq, the Alq 3, respectively, a vacuum vapor deposition apparatus (a first It was attached to a vacuum chamber).

更に、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボートにアルミニウムをそれぞれ入れ、真空蒸着装置の第2真空槽に取り付けた。 Further, lithium fluoride tantalum resistance heating boat, placed respectively aluminum to tungsten resistance heating boat was attached to the second vacuum chamber of a vacuum deposition apparatus.

まず、第1の真空槽を4×10 -4 Paまで減圧した後、α−NPDの入った前記加熱ボートに通電して加熱し、蒸着速度0.1〜0.2nm/秒で透明支持基板に膜厚20nmの厚さになるように蒸着し、正孔注入/輸送層を設けた。 First, after the vacuum of the first vacuum chamber to 4 × 10 -4 Pa, and heated by supplying an electric current to the boat containing alpha-NPD, a transparent supporting substrate at a deposition rate of 0.1 to 0.2 nm / sec It was deposited to a thickness of the film thickness 20nm to, a hole injection / transport layer.

更に、H4の入った前記加熱ボートとIr−1の入ったボートをそれぞれ独立に通電して発光ホストであるH4と発光ドーパントであるIr−1の蒸着速度が100:6になるように調節し、膜厚30nmの厚さになるように蒸着し、発光層を設けた。 Moreover, the heating boat and Ir-1 of containing a deposition rate of Ir-1 is H4 and the light emitting dopant which is a light-emitting host energized boat independently containing the H4 100: of 6 as adjusted , it was deposited to a thickness of a film thickness 30 nm, which a light-emitting layer.

次いで、BAlqの入った前記加熱ボートに通電して加熱し、蒸着速度0.1〜0.2nm/秒で厚さ10nmの正孔阻止層を設けた。 Then heated by supplying an electric current to the heating boat charged with BAlq, form a hole blocking layer having a thickness of 10nm at a deposition rate of 0.1 to 0.2 nm / sec. 更にAlq 3の入った前記加熱ボートを通電して加熱し、蒸着速度0.1〜0.2nm/秒で膜厚20nmの電子輸送層を設けた。 Further heated by energizing the heating boat charged with Alq 3, an electron transporting layer having a thickness of 20nm at a deposition rate of 0.1 to 0.2 nm / sec.

次に、電子輸送層まで成膜した素子を真空のまま第2真空槽に移した後、電子輸送層の上にステンレス鋼製の長方形穴あきマスクが配置されるように装置外部からリモートコントロールして設置した。 Then, after transferring the formed elements in the second vacuum chamber while the vacuum to the electron-transporting layer, and a remote control from the outside of the apparatus as stainless steel rectangular perforated mask is placed on the electron transport layer It was installed Te.

第2真空槽を2×10 -4 Paまで減圧した後、フッ化リチウム入りのボートに通電して蒸着速度0.01〜0.02nm/秒で膜厚0.5nmの陰極バッファー層を設け、次いでアルミニウムの入ったボートに通電して、蒸着速度1〜2nm/秒で膜厚150nmの陰極をつけ、有機EL素子1−1を作製した。 After decompression of the second vacuum chamber to 2 × 10 -4 Pa, a cathode buffer layer of a thickness 0.5nm provided at a deposition rate 0.01~0.02Nm / sec by supplying an electric current to the boat of lithium fluoride-containing, then energized boat containing aluminum, with a cathode having a thickness 150nm at a deposition rate of 1 to 2 nm / sec, to produce an organic EL element 1-1.

《有機EL素子2−2〜2−9の作製》 "Fabrication of organic EL element 2-2~2-9"
有機EL素子2−1の作製において、正孔阻止化合物のBAlqを表2に記載の正孔阻止化合物に変更した以外は同様にして、有機EL素子2−2〜2−9を作製した。 In the preparation of the organic EL element 2-1, except that the BAlq hole blocking compound was replaced by the hole blocking compounds described in Table 2 in the same manner, an organic EL device was fabricated 2-2~2-9.

《有機EL素子の評価》 "Evaluation of Organic EL element"
実施例1と同様の評価を行った。 It was evaluated in the same manner as in Example 1. 得られた結果を表10に示す。 The results obtained are shown in Table 10.

表10から、本発明に係る化合物を用いて作製した有機EL素子は、比較例の有機EL素子に比べ、高い発光効率と発光寿命の長寿命化が達成できることが明らかである。 Table 10, the organic EL element manufactured using the compounds according to the present invention, compared with the organic EL device of Comparative Example, it is clear that the lifetime of high luminous efficiency and emission lifetime can be achieved.

実施例3 Example 3
《フルカラー表示装置の作製》 "Preparation of a full-color display device"
(青色発光素子の作製) (Preparation of blue light emitting element)
実施例1の有機EL素子1−11を青色発光素子として用いた。 The organic EL element 1-11 of Example 1 was used as a blue light emitting element.

(緑色発光素子の作製) (Preparation of green light emitting element)
実施例2の有機EL素子2−2を緑色発光素子として用いた。 Using the organic EL element 2-2 of Example 2 as a green light emitting element.

(赤色発光素子の作製) (Preparation of red light-emitting element)
実施例2の有機EL素子2−2において、Ir−1をIr−9に変更した以外は同様にして、赤色発光素子を作製し、これを赤色発光素子として用いた。 In the organic EL element 2-2 of Example 2, except for changing the Ir-1 to Ir-9 in the same manner, to produce a red light emitting element, it was used as red light emitting element.

上記で作製した赤色、緑色、青色発光有機EL素子を同一基板上に並置し、図1に記載のような形態を有するアクティブマトリクス方式フルカラー表示装置を作製した。 Red prepared above, green, juxtaposing a blue emitting organic EL device on the same substrate to fabricate an active matrix type full color display apparatus having a configuration as described in Figure 1. 図2には、作製した前記表示装置の表示部Aの模式図のみを示した。 FIG. 2 shows only schematic drawing of a display section A of the display device manufactured. 即ち、同一基板上に複数の走査線5及びデータ線6を含む配線部と並置した複数の画素3(発光の色が赤領域の画素、緑領域の画素、青領域の画素等)とを有し、配線部の走査線5及び複数のデータ線6はそれぞれ導電材料からなり、走査線5とデータ線6は格子状に直交して、直交する位置で画素3に接続している(詳細は図示せず)。 That is, a plurality of pixels 3 (the color of light emission pixels in the red area, the pixels of the green region, pixels etc. blue region) juxtaposed with wiring section containing plural scanning lines 5 and plural data lines 6 on the same substrate and Yes and become wiring portions of the scanning lines 5 and plural data lines 6 from the respective conductive material, the lines 5 and the lines 6 perpendicular to the grid pattern, and connected with the pixels 3 at the crossed points ( not shown). 前記複数画素3は、それぞれの発光色に対応した有機EL素子、アクティブ素子であるスイッチングトランジスタと駆動トランジスタそれぞれが設けられたアクティブマトリクス方式で駆動されており、走査線5から走査信号が印加されるとデータ線6から画像データ信号を受け取り、受け取った画像データに応じて発光する。 Wherein the plurality of pixels 3, the organic EL elements corresponding to the respective emission colors, respectively switching transistor and the driving transistor is an active device are driven by an active matrix system which is provided, the scanning signal from the scanning lines 5 are applied and receive the data signal from the data lines 6, and emit light corresponding to received image data. このように赤、緑、青の画素を適宜、並置することによって、フルカラー表示装置を作製した。 Thus red, green, by appropriately juxtaposing blue pixels, to produce a full color display device.

このフルカラー表示装置は駆動することにより、輝度が高く、高耐久性を有し、且つ鮮明なフルカラー動画表示が得られることが分かった。 By this full-color display device to be driven, high luminance, has high durability, and sharp full-color moving image display could be obtained.

実施例4 Example 4
《白色発光素子及び白色照明装置の作製−1》 "Preparation of white light emitting element and a white illumination device -1"
実施例1の透明電極基板の電極を20mm×20mmにパターニングし、その上に実施例1と同様に正孔注入/輸送層としてα−NPDを25nmの厚さで成膜し、更に化合物12の入った前記加熱ボートと例示化合物Ir−13の入ったボート及びIr−9の入ったボートをそれぞれ独立に通電して、発光ホストである化合物12と発光ドーパントであるIr−13及びIr−9の蒸着速度が100:5:0.6になるように調節し、膜厚30nmの厚さになるように蒸着し、発光層を設けた。 Patterning the transparent electrode substrate of the electrode of Example 1 in 20 mm × 20 mm, was deposited alpha-NPD in the same manner as in Example 1 thereon as a hole injecting / transporting layer with a thickness of 25 nm, further compounds 12 energized containing said heating boat and the exemplified compound Ir-13 containing boat and Ir-9 of entering the boat independently of Ir-13 and Ir-9 is the compound 12 is a light-emitting host emitting dopant the deposition rate of 100: 5: adjusted to 0.6, was deposited to a thickness of a film thickness 30 nm, which a light-emitting layer.

次いで、BCPを10nm成膜して正孔阻止層を設けた。 Then, a hole blocking layer was 10nm deposited BCP. 更に、Alq 3を40nmで成膜し電子輸送層を設けた。 Furthermore, it was deposited Alq 3 at 40nm an electron transporting layer.

次に、実施例1と同様に電子注入層の上に、ステンレス鋼製の透明電極とほぼ同じ形状の正方形穴あきマスクを設置し、陰極バッファー層としてフッ化リチウム0.5nm及び陰極としてアルミニウム150nmを蒸着成膜した。 Next, on the same way an electron injection layer as in Example 1, a square perforated mask having substantially the same shape as the stainless steel of the transparent electrode is placed, aluminum 150nm as lithium 0.5nm and a cathode fluoride as a cathode buffer layer was vapor deposited.

この素子を実施例1と同様な方法及び同様な構造の封止缶を具備させ、図5、図6に示すような平面ランプを作製した。 The device is provided with a sealing can in a similar manner and similar structure as in Example 1, FIG. 5, to prepare a flat lamp shown in FIG. この平面ランプに通電したところほぼ白色の光が得られ、照明装置として使用できることが分かった。 Almost white light obtained was energized to this plane lamp was found to be used as a lighting device.

実施例5 Example 5
《白色発光素子及び白色照明装置の作製−2》 "Preparation of white light emitting element and a white illumination device -2"
陽極として100mm×100mm×1.1mmのガラス基板上にITO(インジウムチンオキシド)を100nm製膜した基板(NHテクノグラス社製NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。 After patterning the ITO (indium tin oxide) to 100 mm × 100 mm × 1.1 mm glass substrate as an anode substrate was 100nm film formation (NH Techno Glass NA-45), provided with the ITO transparent electrode the transparent supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas and subjected to UV-ozone cleaning for 5 minutes.

この透明支持基板上に、ポリ(3,4−エチレンジオキシチオフェン)−ポリスチレンスルホネート(PEDOT/PSS、Bayer社製、Baytron P Al 4083)を純水で70%に希釈した溶液を3000rpm、30秒でスピンコート法により製膜した後、200℃にて1時間乾燥し、膜厚30nmの第1正孔輸送層を設けた。 This transparent support substrate, poly (3,4-ethylenedioxythiophene) - polystyrene sulfonate (PEDOT / PSS, Bayer Co., Baytron P Al 4083) 3000 rpm a solution prepared by diluting 70% with pure water for 30 seconds in after it is deposited by spin coating, dried 1 hour at 200 ° C., was provided with the first hole transport layer having a thickness of 30 nm.

この基板を窒素雰囲気下に移し、第1正孔輸送層上に50mgの化合物Aを10mlのトルエンに溶解した溶液を1000rpm、30秒の条件下、スピンコート法により製膜した。 Transferring the substrate to a nitrogen atmosphere, a solution of compound A 50mg to first hole transport layer was dissolved in toluene 10 ml 1000 rpm, 30 seconds under the conditions of, was formed by spin coating. 180秒間紫外光を照射し、光重合・架橋を行った後、60℃で1時間真空乾燥し第2正孔輸送層とした。 Irradiated with 180 seconds by ultraviolet light, after photopolymerization, crosslinking was 1 hour vacuum drying and the second hole transport layer at 60 ° C..

次に、化合物B(60mg)、Ir−14(3.0mg)、Ir−15(3.0mg)をトルエン6mlに溶解した溶液を用い、1000rpm、30秒の条件下、スピンコート法により製膜した。 Next, Compound B (60mg), Ir-14 (3.0mg), Ir-15 using a solution in toluene 6ml the (3.0 mg), 1000 rpm, 30 seconds under the conditions of, film by spin coating did. 15秒間紫外光を照射し、光重合・架橋を行わせ、更に真空中150℃で1時間加熱を行い、発光層とした。 Irradiated with 15 seconds by ultraviolet light, to perform the photopolymerization, crosslinking, further subjected to 1 hour heating at 0.99 ° C. in vacuo to a light-emitting layer.

更に、化合物C(20mg)をトルエン6mlに溶解した溶液を用い、1000rpm、30秒の条件下、スピンコート法により製膜した。 Moreover, Compound C a (20 mg) using a solution in toluene 6 ml, under the conditions of 1000 rpm, 30 seconds, a film was formed by spin coating. 15秒間紫外光を照射し、光重合・架橋を行わせ、更に真空中80℃で1時間加熱を行い、正孔阻止層とした。 Irradiated with 15 seconds by ultraviolet light, to perform the photopolymerization, crosslinking, further subjected to 1 hour heating at 80 ° C. in vacuo to a hole blocking layer.

続いて、この基板を真空蒸着装置の基板ホルダーに固定し、モリブデン製抵抗加熱ボートにAlq 3を200mg入れ、真空蒸着装置に取り付けた。 Subsequently, the substrate was fixed to a substrate holder of a vacuum deposition apparatus, the Alq 3 was placed 200mg to molybdenum resistance heating boat was attached to a vacuum deposition apparatus. 真空槽を4×10 -4 Paまで減圧した後、Alq 3の入った前記加熱ボートに通電して加熱し、蒸着速度0.1nm/秒で前記電子輸送層の上に蒸着して、更に膜厚40nmの電子輸送層を設けた。 After pressure in the vacuum tank was reduced to 4 × 10 -4 Pa, and heated by supplying an electric current to the boat containing Alq 3, it is deposited on the electron transport layer at a deposition rate of 0.1 nm / sec, further film an electron transporting layer having a thickness 40 nm. なお、蒸着時の基板温度は室温であった。 The substrate temperature during the deposition was room temperature. 引き続き、フッ化リチウム0.5nm及びアルミニウム110nmを蒸着して陰極を形成し、白色発光有機EL素子を作製した。 Subsequently, to form a cathode by depositing lithium fluoride 0.5nm and aluminum 110 nm, to produce a white light-emitting organic EL device.

この素子に通電したところほぼ白色の光が得られ、照明装置として使用できることが判った。 This device substantially white light is obtained was energized, it was found to be usable as a lighting device.

実施例6 Example 6
《有機EL素子6−1〜6−5の作製》 "Fabrication of organic EL element 6-1 to 6-5"
陽極として100mm×100mm×1.1mmのガラス基板上にITO(インジウムチンオキシド)を100nm製膜した基板(NHテクノグラス社製NA45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をイソプロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。 After patterning the ITO substrate with 100nm film forming the (indium tin oxide) (NH Techno Glass NA45) to 100 mm × 100 mm × 1.1 mm glass substrate as an anode, a transparent support having the ITO transparent electrode the substrate was ultrasonically washed with isopropyl alcohol, dried with dry nitrogen gas and subjected to UV-ozone cleaning for 5 minutes.

この基板を市販のスピンコータに取り付け、Baytron P(PEDOT/PSS溶液(ポリ(3,4)エチレンジオキシチオフェン−ポリスチレンスルホン酸ドープ体)/バイエル社製)をスピンコートで塗布した後、150℃で1.5時間真空乾燥し、ホール注入層を作製した(膜厚50nm)。 Mounting the substrate in a commercially available spin coater, Baytron P (PEDOT / PSS solution (poly (3,4) ethylenedioxythiophene - polystyrene sulfonic acid doped material) / Bayer Co.) was coated by spin coating, at 0.99 ° C. 1.5 hours and vacuum-dried to produce a hole injection layer (film thickness 50 nm).

次いで、CBP(60mg)とIr−1(3.0mg)をトルエン6mlに溶解した溶液を用い、1000rpm、30秒の条件下、スピンコートし(膜厚約60nm)、60℃で1時間真空乾燥し発光層とした。 Then, using a solution CBP a (60 mg) and Ir-1 (3.0 mg) was dissolved in toluene 6 ml, 1000 rpm, 30 seconds under the conditions of, by spin coating (film thickness of about 60 nm), 1 hour and vacuum dried at 60 ° C. It was to the light-emitting layer.

この透明支持基板を市販の真空蒸着装置の基板ホルダーに固定し、モリブデン製抵抗加熱ボートにバソキュプロイン(BCP)を200mg入れ、別のモリブデン製抵抗加熱ボートにAlq 3を200mg入れ、真空蒸着装置に取り付けた。 The transparent supporting substrate was fixed to a substrate holder of a vacuum deposition apparatus available on the market, putting 200mg of bathocuproine (BCP) to resistive heating molybdenum boat, Alq 3 is placed 200mg in a third resistive heating molybdenum boat, attached to a vacuum vapor deposition apparatus It was.

次いで、真空槽を4×10 -4 Paまで減圧した後、Alq 3の入った前記加熱ボートに通電して加熱し、蒸着速度0.1nm/秒で前記電子輸送層の上に蒸着して、更に膜厚40nmの電子注入層を設けた。 Next, after the pressure in the vacuum tank was reduced to 4 × 10 -4 Pa, and heated by supplying an electric current to the boat containing Alq 3, it is deposited on the electron transport layer at a deposition rate of 0.1 nm / sec, further provided an electron injection layer having a thickness of 40 nm. なお、蒸着時の基板温度は室温であった。 The substrate temperature during the deposition was room temperature. 引き続きフッ化リチウム0.5nm及びアルミニウム110nmを蒸着して陰極を形成し、有機EL素子6−1を作製した。 Subsequently forming a cathode by depositing lithium fluoride 0.5nm and aluminum 110 nm, to manufacture an organic EL element 6-1.

有機EL素子6−1の作製において、発光層のCBPを表9に示す化合物に置き換えた以外は、有機EL素子6−1と同じ方法で6−2〜6−5を作製した。 In the preparation of the organic EL element 6-1, except that the CBP luminescent layers was replaced with compounds shown in Table 9, were prepared 6-2~6-5 in the same manner as the organic EL element 6-1.

《有機EL素子の評価》 "Evaluation of Organic EL element"
以下のようにして作製した有機EL素子6−1〜6−5の評価を行い、その結果を表9に示す。 It evaluates the organic EL elements 6-1 to 6-5 were prepared as follows, and the results are shown in Table 9.

(外部取り出し量子効率) (External extraction quantum efficiency)
作製した有機EL素子について、23℃、乾燥窒素ガス雰囲気下で2.5mA/cm 2定電流を印加した時の外部取り出し量子効率(%)を測定した。 The organic EL devices fabricated, 23 ° C., 2.5 mA under a dry nitrogen atmosphere / cm 2 external extraction quantum efficiency upon application of a constant current (%) was measured. なお測定には同様に分光放射輝度計CS−1000(コニカミノルタセンシング製)を用いた。 Incidentally using a spectral radiance meter CS-1000 (produced by Konica Minolta Sensing) As for the measurement.

表11の外部取り出し量子効率の測定結果は、有機EL素子6−1の測定値を100とした時の相対値で表した。 Taking out measurement of the quantum efficiency of the table 11 is expressed by a relative value when the measurement value of the organic EL element 6-1 and 100.

表11から、本発明の有機EL素子は、高効率化が達成されていることが分かった。 Table 11, the organic EL device of the present invention has been found to increase in efficiency have been achieved.

有機EL素子から構成される表示装置の一例を示した模式図である。 It is a schematic diagram showing an example of a display containing an organic EL device. 表示部Aの模式図である。 It is a schematic drawing of a display section A. 画素の模式図である。 It is a schematic diagram of a pixel. パッシブマトリクス方式フルカラー表示装置の模式図である。 It is a schematic view of a passive matrix full-color displays. 照明装置の概略図である。 It is a schematic view of a lighting device. 照明装置の模式図である。 It is a schematic view of the lighting device.

符号の説明 DESCRIPTION OF SYMBOLS

1 ディスプレイ 3 画素 5 走査線 6 データ線 7 電源ライン 10 有機EL素子 11 スイッチングトランジスタ 12 駆動トランジスタ 13 コンデンサ A 表示部 B 制御部 102 ガラスカバー 105 陰極 106 有機EL層 107 透明電極付きガラス基板 108 窒素ガス 109 捕水剤 1 displays three pixels 5 scan lines 6 data lines 7 supply line 10 organic EL element 11 switching transistor 12 driving transistor 13 capacitor A display unit B control section 102 glass cover 105 cathode 106 organic EL layer 107 transparent electrode-coated glass substrate 108 Nitrogen gas 109 Tomizuzai

Claims (16)

  1. 下記一般式(1)で表される構造を置換基として分子内に有する化合物を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ス素子材料。 The organic electroluminescent device material characterized by a structure represented by the following general formula (1) a compound having in the molecule as a substituent.
    (式中、Xaは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。Z 1 、Z 2は芳香族炭化水素環または芳香族複素環を表すが、いずれか一方は芳香族複素環である。Z 3は2価の連結基または単なる結合手を表す。) (Wherein, Xa is an oxygen atom, a sulfur atom, .Z 1 representing a selenium atom or a tellurium atom, Z 2 represents an aromatic hydrocarbon ring or aromatic heterocyclic ring, is either an aromatic heterocyclic .Z 3 represents a divalent linking group or a single bond.)
  2. 前記一般式(1)において、Z 3が単なる結合手を表すことを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子材料。 In Formula (1), an organic electroluminescence device material according to claim 1, wherein a Z 3 represents a single bond.
  3. 前記一般式(1)において、Z 1 、Z 2の少なくとも一方が六員環であることを特徴とする請求項1または2に記載の有機エレクトロルミネッセンス素子材料。 In Formula (1), an organic electroluminescence device material according to claim 1 or 2, wherein at least one of Z 1, Z 2 is a six-membered ring.
  4. 前記一般式(1)が下記一般式(2)で表されることを特徴とする請求項1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to claim 1, wherein the general formula (1) is represented by the following general formula (2).
    (式中、Xbは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。X 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 、X 18は各々炭素原子または窒素原子を表すが、その少なくとも一つは窒素原子である。R 1 、R 2は各々置換基を表す。n、mは0≦n+m≦7を満たす0から4の整数を表す。) (Wherein, Xb is an oxygen atom, a sulfur atom, .X 11 representing a selenium atom or a tellurium atom, X 12, X 13, X 14, X 15, X 16, X 17, X 18 are each a carbon atom or a nitrogen atom represents a, .n representing the at least one of which is a nitrogen atom .R 1, R 2 are each a substituent, m represents an integer from 0 satisfying 0 ≦ n + m ≦ 7 4 .)
  5. 前記一般式(2)が下記一般式(3)で表されることを特徴とする請求項3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to claim 3, wherein the general formula (2) is represented by the following general formula (3).
    (式中、Xcは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 31 、R 32は各々置換基を表す。n31は0から3の整数、m31は0から4の整数を表す。) (Wherein, Xc represents an oxygen atom, a sulfur atom, a selenium atom or .R 31 representing a tellurium atom, R 32 is .n31 each represent a substituent an integer from 0 to 3, m31 represents an integer of 0 to 4. )
  6. 前記一般式(2)が下記一般式(4)で表されることを特徴とする請求項3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to claim 3, wherein the general formula (2) is represented by the following general formula (4).
    (式中、Xdは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 41 、R 42は各々置換基を表す。n41は0から3の整数、m41は0から4の整数を表す。) (Wherein, Xd represents an oxygen atom, a sulfur atom, a selenium atom or a tellurium atom represents .R 41, R 42 are each an integer of .n41 representing a substituent from 0 3, m41 represents an integer of 0 to 4. )
  7. 前記一般式(2)が下記一般式(5)で表されることを特徴とする請求項3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to claim 3, wherein the general formula (2) is represented by the following general formula (5).
    (式中、Xeは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 51 、R 52は各々置換基を表す。n51は0から3の整数、m51は0から4の整数を表す。) (Wherein, Xe represents an oxygen atom, a sulfur atom, a selenium atom or tellurium atom .R 51, R 52 is .n51 each represent a substituent an integer from 0 to 3, the integer m51 is from 0 to 4. )
  8. 前記一般式(2)が下記一般式(6)で表されることを特徴とする請求項3に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to claim 3, wherein the general formula (2) is represented by the following general formula (6).
    (式中、Xfは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。R 61 、R 62は各々置換基を表す。n61は0から3の整数、m61は0から4の整数を表す。) (Wherein, Xf represents an oxygen atom, a sulfur atom, .R 61 representing a selenium atom or a tellurium atom, R 62 is .n61 each represent a substituent an integer from 0 to 3, m61 represents an integer of 0 to 4. )
  9. 前記一般式(1)が下記一般式(7)で表されることを特徴とする請求項1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子材料。 The organic electroluminescence device material according to claim 1, wherein the general formula (1) is represented by the following general formula (7).
    (式中、Xgは酸素原子、硫黄原子、セレン原子またはテルル原子を表す。X 21 、X 22 、X 23 、X 24 、X 25 、X 26 、X 27 、X 28は各々炭素原子または窒素原子を表すが、X 21 、X 22 、X 23 、X 24の少なくとも一つ、且つX 25 、X 26 、X 27 、X 28の少なくとも一つは窒素原子である。R 3 、R 4は各々置換基を表す。p、qは0≦p+q≦6を満たす0から3の整数を表す。) (Wherein, Xg represents an oxygen atom, a sulfur atom, .X 21 representing a selenium atom or a tellurium atom, X 22, X 23, X 24, X 25, X 26, X 27, X 28 are each a carbon atom or a nitrogen atom represents a, at least one, and X 25, .R 3, R 4 at least one is a nitrogen atom of X 26, X 27, X 28 are each substituted X 21, X 22, X 23 , X 24 It represents a group .p, q is an integer of from 0 satisfying 0 ≦ p + q ≦ 6 3.)
  10. ホスト化合物及びリン光性化合物を含有する発光層を有する有機エレクトロルミネッセンス素子であって、該素子を構成するいずれかの層に請求項1〜9のいずれか1項に記載の有機エレクトロルミネッセンス素子材料を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ス素子。 An organic electroluminescent device having a light-emitting layer containing a host compound and a phosphorescent compound, an organic electroluminescence device material according to any one of claims 1 to 9 to one of the layers constituting the the element the organic electroluminescent device characterized by containing a.
  11. 前記いずれかの層が発光層であることを特徴とする請求項10に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to claim 10, wherein the one of the layers is a light emitting layer.
  12. 前記いずれかの層が正孔阻止層であることを特徴とする請求項10に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescence device according to claim 10, wherein the one of the layers is a hole blocking layer.
  13. 前記リン光性化合物がイリジウム錯体化合物または白金錯体化合物であることを特徴とする請求項10〜12のいずれか1項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 10 to 12, wherein the phosphorescent compound is an iridium complex compound or a platinum complex compound.
  14. 発光が白色であることを特徴とする請求項10〜13のいずれか1項に記載の有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 10-13, wherein the light emission is white.
  15. 請求項10〜14のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする表示装置。 Display device characterized by having an organic electroluminescent element of any one of claims 10 to 14.
  16. 請求項10〜14のいずれか1項に記載の有機エレクトロルミネッセンス素子を有することを特徴とする照明装置。 Lighting apparatus characterized by having an organic electroluminescent element of any one of claims 10 to 14.
JP2006255132A 2006-09-21 2006-09-21 The organic electroluminescent device material Active JP5589251B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2006255132A JP5589251B2 (en) 2006-09-21 2006-09-21 The organic electroluminescent device material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2006255132A JP5589251B2 (en) 2006-09-21 2006-09-21 The organic electroluminescent device material

Publications (2)

Publication Number Publication Date
JP2008074939A true JP2008074939A (en) 2008-04-03
JP5589251B2 JP5589251B2 (en) 2014-09-17

Family

ID=39347326

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2006255132A Active JP5589251B2 (en) 2006-09-21 2006-09-21 The organic electroluminescent device material

Country Status (1)

Country Link
JP (1) JP5589251B2 (en)

Cited By (263)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010098223A (en) * 2008-10-20 2010-04-30 Konica Minolta Holdings Inc Organic electroluminescence device, organic electroluminescence material, display device and illuminating device
US20100187984A1 (en) * 2009-01-16 2010-07-29 Universal Display Corporation Materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
WO2010090077A1 (en) * 2009-02-06 2010-08-12 コニカミノルタホールディングス株式会社 Organic electroluminescent element, and illumination device and display device each comprising the element
JP2011084531A (en) * 2009-10-19 2011-04-28 Konica Minolta Holdings Inc Material for organic electroluminescent element, organic electroluminescent element, illumination device and display device
WO2011051404A1 (en) 2009-10-28 2011-05-05 Basf Se Heteroleptic carbene complexes and use thereof in organic electronics
WO2011073149A1 (en) 2009-12-14 2011-06-23 Basf Se Metal complexes comprising diazabenzimidazol carbene-ligands and the use thereof in oleds
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
WO2012090967A1 (en) 2010-12-28 2012-07-05 出光興産株式会社 Material for organic electroluminescent elements, and organic electroluminescent element using same
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
WO2012102967A1 (en) 2011-01-24 2012-08-02 Universal Display Corporation Aza - dibenzothiophene, aza - dibenzofuran and aza - dibenzoselenophene derivatives for use in oled ' s
US8269317B2 (en) 2010-11-11 2012-09-18 Universal Display Corporation Phosphorescent materials
JP2012190843A (en) * 2011-03-08 2012-10-04 Toshiba Corp Organic electroluminescent element, display unit, and lighting device
WO2012153780A1 (en) * 2011-05-11 2012-11-15 出光興産株式会社 Novel compound, material for organic electroluminescence device, and organic electroluminescence device
US8367223B2 (en) 2008-11-11 2013-02-05 Universal Display Corporation Heteroleptic phosphorescent emitters
US8409729B2 (en) 2011-07-28 2013-04-02 Universal Display Corporation Host materials for phosphorescent OLEDs
US8432095B2 (en) 2011-05-11 2013-04-30 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
US8440326B2 (en) 2008-06-30 2013-05-14 Universal Display Corporation Hole transport materials containing triphenylene
JP2013138230A (en) * 2013-02-12 2013-07-11 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device, and luminaire
US8492006B2 (en) 2011-02-24 2013-07-23 Universal Display Corporation Germanium-containing red emitter materials for organic light emitting diode
JP2013145890A (en) * 2013-02-12 2013-07-25 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device and lighting system
JP2013157634A (en) * 2013-05-01 2013-08-15 Konica Minolta Inc Organic electroluminescent element material
US8545996B2 (en) 2009-11-02 2013-10-01 The University Of Southern California Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes
US8552420B2 (en) 2011-08-09 2013-10-08 Universal Display Corporation OLED light panel with controlled brightness variation
US8564192B2 (en) 2011-05-11 2013-10-22 Universal Display Corporation Process for fabricating OLED lighting panels
US8563737B2 (en) 2011-02-23 2013-10-22 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US8580394B2 (en) 2009-11-19 2013-11-12 Universal Display Corporation 3-coordinate copper(I)-carbene complexes
US8580399B2 (en) 2011-04-08 2013-11-12 Universal Display Corporation Substituted oligoazacarbazoles for light emitting diodes
WO2014012972A1 (en) 2012-07-19 2014-01-23 Basf Se Dinuclear metal complexes comprising carbene ligands and the use thereof in oleds
US8652656B2 (en) 2011-11-14 2014-02-18 Universal Display Corporation Triphenylene silane hosts
US8659036B2 (en) 2011-06-17 2014-02-25 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
WO2014030666A1 (en) 2012-08-24 2014-02-27 コニカミノルタ株式会社 Transparent electrode, electronic device, and method for manufacturing transparent electrode
US20140054563A1 (en) * 2012-08-24 2014-02-27 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US8673458B2 (en) 2010-06-11 2014-03-18 Universal Display Corporation Delayed fluorescence OLED
US8692241B1 (en) 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US8691401B2 (en) 2010-04-16 2014-04-08 Basf Se Bridged benzimidazole-carbene complexes and use thereof in OLEDS
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US8723209B2 (en) 2012-04-27 2014-05-13 Universal Display Corporation Out coupling layer containing particle polymer composite
US20140131676A1 (en) * 2012-11-09 2014-05-15 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US20140131663A1 (en) * 2012-11-09 2014-05-15 Universal Display Corporation Iridium Complexes With Aza-Benzo Fused Ligands
US8742657B2 (en) 2010-06-11 2014-06-03 Universal Display Corporation Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications
US8748011B2 (en) 2011-02-23 2014-06-10 Universal Display Corporation Ruthenium carbene complexes for OLED material
US8748012B2 (en) 2011-05-25 2014-06-10 Universal Display Corporation Host materials for OLED
JP2014131079A (en) * 2014-03-13 2014-07-10 Konica Minolta Inc Material for organic electroluminescent element, organic electroluminescent element, illuminating device and display device
US8795850B2 (en) 2011-05-19 2014-08-05 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology
JP2014158039A (en) * 2014-04-04 2014-08-28 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device and lighting system
US8822708B2 (en) 2007-08-08 2014-09-02 Universal Display Corporation Benzo-fused thiophene / triphenylene hybrid materials
JP2014170946A (en) * 2014-04-04 2014-09-18 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device and luminaire
WO2014147134A1 (en) 2013-03-20 2014-09-25 Basf Se Azabenzimidazole carbene complexes as efficiency booster in oleds
WO2014157494A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Material for organic electroluminescent elements, organic electroluminescent element, display device and lighting device
WO2014157618A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Organic electroluminescent element, and lighting device and display device which are provided with same
US8871361B2 (en) 2011-02-23 2014-10-28 Universal Display Corporation Tetradentate platinum complexes
WO2014177518A1 (en) 2013-04-29 2014-11-06 Basf Se Transition metal complexes with carbene ligands and the use thereof in oleds
US8884316B2 (en) 2011-06-17 2014-11-11 Universal Display Corporation Non-common capping layer on an organic device
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
US8927749B2 (en) 2013-03-07 2015-01-06 Universal Display Corporation Organic electroluminescent materials and devices
US8926119B2 (en) 2011-08-04 2015-01-06 Universal Display Corporation Extendable light source with variable light emitting area
US8927308B2 (en) 2011-05-12 2015-01-06 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
WO2015000955A1 (en) 2013-07-02 2015-01-08 Basf Se Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
US8946697B1 (en) 2012-11-09 2015-02-03 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US8952362B2 (en) 2012-08-31 2015-02-10 The Regents Of The University Of Michigan High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion
US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US8968887B2 (en) 2010-04-28 2015-03-03 Universal Display Corporation Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
US8969592B2 (en) 2012-01-10 2015-03-03 Universal Display Corporation Heterocyclic host materials
US8987451B2 (en) 2012-01-03 2015-03-24 Universal Display Corporation Synthesis of cyclometallated platinum(II) complexes
US9005772B2 (en) 2011-02-23 2015-04-14 Universal Display Corporation Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
WO2015063046A1 (en) 2013-10-31 2015-05-07 Basf Se Azadibenzothiophenes for electronic applications
US9040962B2 (en) 2010-04-28 2015-05-26 Universal Display Corporation Depositing premixed materials
US9054323B2 (en) 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US9059412B2 (en) 2012-07-19 2015-06-16 Universal Display Corporation Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs
US9076973B2 (en) 2008-09-03 2015-07-07 Universal Display Corporation Phosphorescent materials
JP2015151352A (en) * 2014-02-13 2015-08-24 国立大学法人山形大学 Benzofuropyrimidine derivative, host material comprising the same and organic electroluminescent element using the same
US9118017B2 (en) 2012-02-27 2015-08-25 Universal Display Corporation Host compounds for red phosphorescent OLEDs
US9130177B2 (en) 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
US9142786B2 (en) 2007-03-08 2015-09-22 Universal Display Corporation Phosphorescent materials
US9142792B2 (en) 2010-06-18 2015-09-22 Basf Se Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
US9166175B2 (en) 2012-11-27 2015-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US9163174B2 (en) 2012-01-04 2015-10-20 Universal Display Corporation Highly efficient phosphorescent materials
US9175211B2 (en) 2010-03-03 2015-11-03 Universal Display Corporation Phosphorescent materials
US9181270B2 (en) 2014-02-28 2015-11-10 Universal Display Corporation Method of making sulfide compounds
US9184399B2 (en) 2012-05-04 2015-11-10 Universal Display Corporation Asymmetric hosts with triaryl silane side chains
US9190623B2 (en) 2012-11-20 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9190621B2 (en) 2007-03-08 2015-11-17 Universal Display Corporation Materials for organic light emitting diode
US9193745B2 (en) 2011-11-15 2015-11-24 Universal Display Corporation Heteroleptic iridium complex
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US9212197B2 (en) 2011-05-19 2015-12-15 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants
US9217004B2 (en) 2011-11-21 2015-12-22 Universal Display Corporation Organic light emitting materials
US9224958B2 (en) 2013-07-19 2015-12-29 Universal Display Corporation Organic electroluminescent materials and devices
US9231218B2 (en) 2012-07-10 2016-01-05 Universal Display Corporation Phosphorescent emitters containing dibenzo[1,4]azaborinine structure
US9252377B2 (en) 2011-07-14 2016-02-02 Universal Display Corporation Inorganic hosts in OLEDs
WO2016016791A1 (en) 2014-07-28 2016-02-04 Idemitsu Kosan Co., Ltd (Ikc) 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds)
EP2982676A1 (en) 2014-08-07 2016-02-10 Idemitsu Kosan Co., Ltd. Benzimidazo[2,1-B]benzoxazoles for electronic applications
US9281483B2 (en) 2006-02-10 2016-03-08 Universal Display Corporation Organic electroluminescent materials and devices
EP2993215A1 (en) 2014-09-04 2016-03-09 Idemitsu Kosan Co., Ltd. Azabenzimidazo[2,1-a]benzimidazoles for electronic applications
US9287513B2 (en) 2012-09-24 2016-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US9293712B2 (en) 2013-10-11 2016-03-22 Universal Display Corporation Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
US9306179B2 (en) 2013-11-08 2016-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US9312499B1 (en) 2015-01-05 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9312505B2 (en) 2012-09-25 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9315724B2 (en) 2011-06-14 2016-04-19 Basf Se Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs
US9318710B2 (en) 2012-07-30 2016-04-19 Universal Display Corporation Organic electroluminescent materials and devices
US9324949B2 (en) 2013-07-16 2016-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US20160118594A1 (en) * 2014-10-22 2016-04-28 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
EP3015469A1 (en) 2014-10-30 2016-05-04 Idemitsu Kosan Co., Ltd. 5-((benz)imidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications
WO2016079169A1 (en) 2014-11-18 2016-05-26 Basf Se Pt- or pd-carbene complexes for use in organic light emitting diodes
WO2016079667A1 (en) 2014-11-17 2016-05-26 Idemitsu Kosan Co., Ltd. Indole derivatives for electronic applications
US9373802B2 (en) 2011-02-07 2016-06-21 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
EP3034506A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 4-functionalized carbazole derivatives for electronic applications
EP3034507A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs)
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
US9397310B2 (en) 2011-07-14 2016-07-19 Universal Display Corporation Organice electroluminescent materials and devices
US9397302B2 (en) 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US9397309B2 (en) 2014-03-13 2016-07-19 Universal Display Corporation Organic electroluminescent devices
US9406893B2 (en) 2010-09-09 2016-08-02 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
EP3053918A1 (en) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd 2-carbazole substituted benzimidazoles for electronic applications
EP3054498A1 (en) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd. Bisimidazodiazocines
US9419225B2 (en) 2013-03-14 2016-08-16 Universal Display Corporation Organic electroluminescent materials and devices
EP3056498A1 (en) * 2015-02-13 2016-08-17 Samsung SDI Co., Ltd. Diazadibenzofurane and diazadibenzothiophene derivatives and their use in organic optoelectronic devices
EP3061759A1 (en) 2015-02-24 2016-08-31 Idemitsu Kosan Co., Ltd Nitrile substituted dibenzofurans
US9435021B2 (en) 2010-07-29 2016-09-06 University Of Southern California Co-deposition methods for the fabrication of organic optoelectronic devices
US9444075B2 (en) 2014-11-26 2016-09-13 Universal Display Corporation Emissive display with photo-switchable polarization
US9450195B2 (en) 2014-12-17 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
EP3070144A1 (en) 2015-03-17 2016-09-21 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
US9455411B2 (en) 2008-09-25 2016-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US9455417B2 (en) 2011-12-13 2016-09-27 Universal Display Corporation Split electrode for organic devices
EP3072943A1 (en) 2015-03-26 2016-09-28 Idemitsu Kosan Co., Ltd. Dibenzofuran/carbazole-substituted benzonitriles
US9461254B2 (en) 2012-01-03 2016-10-04 Universal Display Corporation Organic electroluminescent materials and devices
EP3075737A1 (en) 2015-03-31 2016-10-05 Idemitsu Kosan Co., Ltd Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes
US9478758B1 (en) 2015-05-08 2016-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US9484541B2 (en) 2014-10-20 2016-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
US9502656B2 (en) 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9502672B2 (en) 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9512136B2 (en) 2012-11-26 2016-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US9512355B2 (en) 2011-12-09 2016-12-06 Universal Display Corporation Organic light emitting materials
WO2016193243A1 (en) 2015-06-03 2016-12-08 Udc Ireland Limited Highly efficient oled devices with very short decay times
US9537106B2 (en) 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9553274B2 (en) 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US9590180B2 (en) 2007-06-23 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9590195B2 (en) 2014-02-28 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9590194B2 (en) 2014-02-14 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
EP3150604A1 (en) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes
EP3150606A1 (en) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes
WO2017056053A1 (en) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes
WO2017056055A1 (en) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes
US9634265B2 (en) 2009-04-28 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US9647218B2 (en) 2013-11-14 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9647217B2 (en) 2014-02-24 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9647221B2 (en) 2011-07-14 2017-05-09 Universal Display Corporation Organic light-emitting devices
US9647227B2 (en) 2005-04-13 2017-05-09 Universal Display Corporation Organic light emitting devices
WO2017078182A1 (en) 2015-11-04 2017-05-11 Idemitsu Kosan Co., Ltd. Benzimidazole fused heteroaryls
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
US9663544B2 (en) 2012-07-25 2017-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US9673406B2 (en) 2009-05-20 2017-06-06 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
US9673407B2 (en) 2014-02-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9673401B2 (en) 2013-06-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9670404B2 (en) 2012-06-06 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
WO2017093958A1 (en) 2015-12-04 2017-06-08 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes
US9691993B2 (en) 2014-04-09 2017-06-27 Universal Display Corporation Organic electroluminescent materials and devices
WO2017109727A1 (en) 2015-12-21 2017-06-29 Idemitsu Kosan Co., Ltd. Hetero-condensed phenylquinazolines and their use in electronic devices
US9711730B2 (en) 2015-01-25 2017-07-18 Universal Display Corporation Organic electroluminescent materials and devices
EP3200255A2 (en) 2016-01-06 2017-08-02 Konica Minolta, Inc. Organic electroluminescent element, method for producing organic electroluminescent element, display, and lighting device
US9725476B2 (en) 2012-07-09 2017-08-08 Universal Display Corporation Silylated metal complexes
US9735378B2 (en) 2013-09-09 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9735373B2 (en) 2013-06-10 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9735377B2 (en) 2005-05-06 2017-08-15 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US9741941B2 (en) 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US9748503B2 (en) 2013-09-13 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9748504B2 (en) 2014-03-25 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9748500B2 (en) 2015-01-15 2017-08-29 Universal Display Corporation Organic light emitting materials
US9755159B2 (en) 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
US9755164B2 (en) 2011-06-08 2017-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US9761814B2 (en) 2014-11-18 2017-09-12 Universal Display Corporation Organic light-emitting materials and devices
US9761807B2 (en) 2013-07-15 2017-09-12 Universal Display Corporation Organic light emitting diode materials
US9773985B2 (en) 2012-05-21 2017-09-26 Universal Display Corporation Organic electroluminescent materials and devices
US9780316B2 (en) 2015-03-16 2017-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US9783564B2 (en) 2011-07-25 2017-10-10 Universal Display Corporation Organic electroluminescent materials and devices
WO2017178864A1 (en) 2016-04-12 2017-10-19 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
EP3239161A1 (en) 2013-07-31 2017-11-01 UDC Ireland Limited Luminescent diazabenzimidazole carbene metal complexes
JP2017533893A (en) * 2014-10-30 2017-11-16 エルジー・ケム・リミテッド Ring compounds and organic light emitting devices comprising the same
US9831437B2 (en) 2013-08-20 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9831447B2 (en) 2013-10-08 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9847498B2 (en) 2014-04-14 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847497B2 (en) 2014-02-18 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9853229B2 (en) 2013-10-23 2017-12-26 University Of Southern California Organic electroluminescent materials and devices
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US9862739B2 (en) 2014-03-31 2018-01-09 Udc Ireland Limited Metal complexes, comprising carbene ligands having an O-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
US9871214B2 (en) 2015-03-23 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US9871212B2 (en) 2014-11-14 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US9899612B2 (en) 2006-12-08 2018-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US9911928B2 (en) 2015-03-19 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9911931B2 (en) 2014-06-26 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929353B2 (en) 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929360B2 (en) 2016-07-08 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9932359B2 (en) 2013-08-30 2018-04-03 University Of Southern California Organic electroluminescent materials and devices
US9935277B2 (en) 2014-01-30 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9935276B2 (en) 2013-02-21 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9954180B2 (en) 2010-08-20 2018-04-24 Universal Display Corporation Bicarbazole compounds for OLEDs
EP3318566A1 (en) 2012-09-20 2018-05-09 UDC Ireland Limited Azadibenzofurans for electronic applications
US9978956B2 (en) 2015-07-15 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9978961B2 (en) 2014-01-08 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9997712B2 (en) 2013-03-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US10003033B2 (en) 2014-02-18 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US10003034B2 (en) 2013-09-30 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US10008679B2 (en) 2014-04-14 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US10008678B2 (en) 2008-12-12 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US10008677B2 (en) 2011-01-13 2018-06-26 Universal Display Corporation Materials for organic light emitting diode
US10033004B2 (en) 2015-06-01 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US10038151B2 (en) 2014-11-12 2018-07-31 Universal Display Corporation Organic electroluminescent materials and devices
US10043987B2 (en) 2014-09-29 2018-08-07 Universal Display Corporation Organic electroluminescent materials and devices
US10056565B2 (en) 2013-11-20 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US10069090B2 (en) 2012-11-20 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US10074806B2 (en) 2013-08-20 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices
US10079349B2 (en) 2011-05-27 2018-09-18 Universal Display Corporation Organic electroluminescent materials and devices
US10084143B2 (en) 2008-09-16 2018-09-25 Universal Display Corporation Phosphorescent materials
US10109799B2 (en) 2015-05-21 2018-10-23 Universal Display Corporation Organic electroluminescent materials and devices
US10121975B2 (en) 2013-07-03 2018-11-06 Universal Display Corporation Organic electroluminescent materials and devices
US10135007B2 (en) 2014-09-29 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10135008B2 (en) 2014-01-07 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10144867B2 (en) 2015-02-13 2018-12-04 Universal Display Corporation Organic electroluminescent materials and devices
US10147892B2 (en) 2010-12-07 2018-12-04 The University Of Southern California Organic electroluminescent materials and devices
US10153443B2 (en) 2016-07-19 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10153445B2 (en) 2016-11-21 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10158089B2 (en) 2011-05-27 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
EP3415521A1 (en) 2011-06-14 2018-12-19 UDC Ireland Limited Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in oleds
US10177316B2 (en) 2015-02-09 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10177318B2 (en) 2015-10-29 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10181564B2 (en) 2015-08-26 2019-01-15 Universal Display Corporation Organic electroluminescent materials and devices
US10199581B2 (en) 2013-07-01 2019-02-05 Universal Display Corporation Organic electroluminescent materials and devices
US10199582B2 (en) 2013-09-03 2019-02-05 University Of Southern California Organic electroluminescent materials and devices
US10205105B2 (en) 2016-08-15 2019-02-12 Universal Display Corporation Organic electroluminescent materials and devices
US10211413B2 (en) 2012-01-17 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US10208026B2 (en) 2014-03-18 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10236458B2 (en) 2016-10-24 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10253252B2 (en) 2014-12-30 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10256427B2 (en) 2014-04-15 2019-04-09 Universal Display Corporation Efficient organic electroluminescent devices
US10256411B2 (en) 2015-05-21 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10256419B2 (en) 2014-05-08 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10270046B2 (en) 2015-03-06 2019-04-23 Universal Display Corporation Organic electroluminescent materials and devices
US10276809B2 (en) 2016-04-05 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10297770B2 (en) 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10301338B2 (en) 2014-05-08 2019-05-28 Universal Display Corporation Organic electroluminescent materials and devices
US10340464B2 (en) 2016-11-10 2019-07-02 Universal Display Corporation Organic electroluminescent materials and devices
US10347851B2 (en) 2013-12-20 2019-07-09 Udc Ireland Limited Highly efficient OLED devices with very short decay times
US10355227B2 (en) 2013-12-16 2019-07-16 Universal Display Corporation Metal complex for phosphorescent OLED
US10355222B2 (en) 2015-02-06 2019-07-16 Universal Display Corporation Organic electroluminescent materials and devices
US10361381B2 (en) 2015-09-03 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10381580B2 (en) 2018-01-03 2019-08-13 Universal Display Corporation Organic electroluminescent materials and devices

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018043761A1 (en) 2016-09-05 2018-03-08 Idemitsu Kosan Co.,Ltd. Specifically substituted aza-dibenzofurans and aza-dibenzothiophenes for organic electronic devices

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002284862A (en) * 2001-03-23 2002-10-03 Tdk Corp Polymer compound and producing method and using method thereof
JP2004002703A (en) * 2002-03-15 2004-01-08 Sumitomo Chem Co Ltd Polymeric compound and polymeric luminescent element using the same
JP2004059899A (en) * 2002-06-05 2004-02-26 Sumitomo Chem Co Ltd Polymer compound and polymeric light-emitting element using the same
WO2004074399A1 (en) * 2003-02-20 2004-09-02 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using same
JP2005126686A (en) * 2003-09-12 2005-05-19 Sumitomo Chemical Co Ltd Light emitting material and light emitting device using the same
JP2005132829A (en) * 2003-10-06 2005-05-26 Sumitomo Chemical Co Ltd Aromatic compound
WO2005113531A1 (en) * 2004-05-21 2005-12-01 Toray Industries, Inc. Light-emitting device material and light-emitting device
JP2007177225A (en) * 2005-12-01 2007-07-12 Sumitomo Chemical Co Ltd Polymeric compound and polymeric light emitting element using the same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002284862A (en) * 2001-03-23 2002-10-03 Tdk Corp Polymer compound and producing method and using method thereof
JP2004002703A (en) * 2002-03-15 2004-01-08 Sumitomo Chem Co Ltd Polymeric compound and polymeric luminescent element using the same
JP2004059899A (en) * 2002-06-05 2004-02-26 Sumitomo Chem Co Ltd Polymer compound and polymeric light-emitting element using the same
WO2004074399A1 (en) * 2003-02-20 2004-09-02 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using same
JP2005126686A (en) * 2003-09-12 2005-05-19 Sumitomo Chemical Co Ltd Light emitting material and light emitting device using the same
JP2005132829A (en) * 2003-10-06 2005-05-26 Sumitomo Chemical Co Ltd Aromatic compound
WO2005113531A1 (en) * 2004-05-21 2005-12-01 Toray Industries, Inc. Light-emitting device material and light-emitting device
JP2007177225A (en) * 2005-12-01 2007-07-12 Sumitomo Chemical Co Ltd Polymeric compound and polymeric light emitting element using the same

Cited By (367)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9871219B2 (en) 2005-04-13 2018-01-16 Universal Display Corporation Organic light emitting devices
US9647227B2 (en) 2005-04-13 2017-05-09 Universal Display Corporation Organic light emitting devices
US9735377B2 (en) 2005-05-06 2017-08-15 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US9281483B2 (en) 2006-02-10 2016-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US9548462B2 (en) 2006-02-10 2017-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US9893306B2 (en) 2006-02-10 2018-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US10158090B2 (en) 2006-02-10 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US9899612B2 (en) 2006-12-08 2018-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US9853227B2 (en) 2007-03-08 2017-12-26 Universal Display Corporation Organic electroluminescent materials and devices
US9577201B2 (en) 2007-03-08 2017-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US10230060B2 (en) 2007-03-08 2019-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US9190621B2 (en) 2007-03-08 2015-11-17 Universal Display Corporation Materials for organic light emitting diode
US9142786B2 (en) 2007-03-08 2015-09-22 Universal Display Corporation Phosphorescent materials
US9911930B2 (en) 2007-03-08 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9590180B2 (en) 2007-06-23 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US10374171B2 (en) 2007-08-08 2019-08-06 Universal Display Corporation Organic electroluminescent materials and devices
US9577200B2 (en) 2007-08-08 2017-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US10312450B2 (en) 2007-08-08 2019-06-04 Universal Display Corporation Organic electroluminescent materials and devices
US8822708B2 (en) 2007-08-08 2014-09-02 Universal Display Corporation Benzo-fused thiophene / triphenylene hybrid materials
US9608206B2 (en) 2007-08-08 2017-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US9997727B2 (en) 2007-08-08 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US8580402B2 (en) 2007-12-28 2013-11-12 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US9123903B2 (en) 2007-12-28 2015-09-01 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US9997726B2 (en) 2007-12-28 2018-06-12 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
US8440326B2 (en) 2008-06-30 2013-05-14 Universal Display Corporation Hole transport materials containing triphenylene
US9630983B2 (en) 2008-09-03 2017-04-25 Universal Display Corporation Organic electroluminescent material and devices
US10186672B2 (en) 2008-09-03 2019-01-22 Universal Display Corporation Organic electroluminescent materials and devices
US9076973B2 (en) 2008-09-03 2015-07-07 Universal Display Corporation Phosphorescent materials
US10084143B2 (en) 2008-09-16 2018-09-25 Universal Display Corporation Phosphorescent materials
US9455411B2 (en) 2008-09-25 2016-09-27 Universal Display Corporation Organic electroluminescent materials and devices
JP2010098223A (en) * 2008-10-20 2010-04-30 Konica Minolta Holdings Inc Organic electroluminescence device, organic electroluminescence material, display device and illuminating device
US8367223B2 (en) 2008-11-11 2013-02-05 Universal Display Corporation Heteroleptic phosphorescent emitters
US10008678B2 (en) 2008-12-12 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
JP2015017114A (en) * 2009-01-16 2015-01-29 ユニバーサル ディスプレイ コーポレイション New materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
US9518063B2 (en) 2009-01-16 2016-12-13 Universal Display Corporation Organic electroluminescent materials and devices
JP2012515216A (en) * 2009-01-16 2012-07-05 ユニバーサル ディスプレイ コーポレイション Aza for Pholed - dibenzothiophene or bruises - new material with a dibenzofuran nucleus
KR20110116177A (en) * 2009-01-16 2011-10-25 유니버셜 디스플레이 코포레이션 New materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
CN106397453A (en) * 2009-01-16 2017-02-15 通用显示公司 Materials with aza-dibenzothiophene or aza-dibenzofuran core for PHOLED
US9067947B2 (en) 2009-01-16 2015-06-30 Universal Display Corporation Organic electroluminescent materials and devices
JP2017071642A (en) * 2009-01-16 2017-04-13 ユニバーサル ディスプレイ コーポレイション New materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
KR101744463B1 (en) 2009-01-16 2017-06-07 유니버셜 디스플레이 코포레이션 New materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
KR101702148B1 (en) * 2009-01-16 2017-02-03 유니버셜 디스플레이 코포레이션 New materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
US20100187984A1 (en) * 2009-01-16 2010-07-29 Universal Display Corporation Materials with aza-dibenzothiophene or aza-dibenzofuran core for pholed
US8952363B2 (en) 2009-01-16 2015-02-10 Universal Display Corporation Organic electroluminescent materials and devices
TWI570126B (en) * 2009-01-16 2017-02-11 Universal Display Corp Process for making an aza-dibenzothiophene compound or an aza-dibenzofuran compound
US9831442B2 (en) 2009-01-16 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
WO2010090077A1 (en) * 2009-02-06 2010-08-12 コニカミノルタホールディングス株式会社 Organic electroluminescent element, and illumination device and display device each comprising the element
US9617255B2 (en) 2009-02-06 2017-04-11 Konica Minolta, Inc. Organic electroluminescent element, and illumination device and display device each comprising the element
JP5541167B2 (en) * 2009-02-06 2014-07-09 コニカミノルタ株式会社 The organic electroluminescence element, an illumination device and a display device equipped with the element
US10312458B2 (en) 2009-03-23 2019-06-04 Universal Display Corporation Organic electroluminescent materials and devices
US9184397B2 (en) 2009-03-23 2015-11-10 Universal Display Corporation Heteroleptic iridium complexes as dopants
US10374173B2 (en) 2009-04-28 2019-08-06 Universal Display Corporation Organic electroluminescent materials and devices
US9634265B2 (en) 2009-04-28 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US9673406B2 (en) 2009-05-20 2017-06-06 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
JP2011084531A (en) * 2009-10-19 2011-04-28 Konica Minolta Holdings Inc Material for organic electroluminescent element, organic electroluminescent element, illumination device and display device
WO2011051404A1 (en) 2009-10-28 2011-05-05 Basf Se Heteroleptic carbene complexes and use thereof in organic electronics
US8545996B2 (en) 2009-11-02 2013-10-01 The University Of Southern California Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes
US9773986B2 (en) 2009-11-19 2017-09-26 The University Of Southern California Copper(I)-carbene complexes and organic electroluminescent devices
US8580394B2 (en) 2009-11-19 2013-11-12 Universal Display Corporation 3-coordinate copper(I)-carbene complexes
US9487548B2 (en) 2009-12-14 2016-11-08 Udc Ireland Limited Metal complexes comprising diazabenzimidazolocarbene ligands and the use thereof in OLEDs
WO2011073149A1 (en) 2009-12-14 2011-06-23 Basf Se Metal complexes comprising diazabenzimidazol carbene-ligands and the use thereof in oleds
US10090476B2 (en) 2009-12-14 2018-10-02 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDs
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
US9175211B2 (en) 2010-03-03 2015-11-03 Universal Display Corporation Phosphorescent materials
US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US8691401B2 (en) 2010-04-16 2014-04-08 Basf Se Bridged benzimidazole-carbene complexes and use thereof in OLEDS
US9040962B2 (en) 2010-04-28 2015-05-26 Universal Display Corporation Depositing premixed materials
US8968887B2 (en) 2010-04-28 2015-03-03 Universal Display Corporation Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
US8673458B2 (en) 2010-06-11 2014-03-18 Universal Display Corporation Delayed fluorescence OLED
US9543532B2 (en) 2010-06-11 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9140428B2 (en) 2010-06-11 2015-09-22 Universal Display Corporation Triplet-triplet annihilation up-conversation for display and lighting applications
US8742657B2 (en) 2010-06-11 2014-06-03 Universal Display Corporation Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications
US9142792B2 (en) 2010-06-18 2015-09-22 Basf Se Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide
US9435021B2 (en) 2010-07-29 2016-09-06 University Of Southern California Co-deposition methods for the fabrication of organic optoelectronic devices
US9954180B2 (en) 2010-08-20 2018-04-24 Universal Display Corporation Bicarbazole compounds for OLEDs
US9406893B2 (en) 2010-09-09 2016-08-02 Semiconductor Energy Laboratory Co., Ltd. Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US9401482B2 (en) 2010-10-08 2016-07-26 Universal Display Corporation Organic electroluminescent materials and devices
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
US8269317B2 (en) 2010-11-11 2012-09-18 Universal Display Corporation Phosphorescent materials
US10147892B2 (en) 2010-12-07 2018-12-04 The University Of Southern California Organic electroluminescent materials and devices
WO2012090967A1 (en) 2010-12-28 2012-07-05 出光興産株式会社 Material for organic electroluminescent elements, and organic electroluminescent element using same
KR20140015285A (en) 2010-12-28 2014-02-06 이데미쓰 고산 가부시키가이샤 Material for organic electroluminescent elements, and organic electroluminescent element using same
US9923151B2 (en) 2010-12-28 2018-03-20 Idemitsu Kosan Co., Ltd. Material for organic electroluminescent elements, and organic electroluminescent element using same
US10008677B2 (en) 2011-01-13 2018-06-26 Universal Display Corporation Materials for organic light emitting diode
US9130177B2 (en) 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
JP2018088526A (en) * 2011-01-24 2018-06-07 ユニバーサル ディスプレイ コーポレイション Electron transporting compound
WO2012102967A1 (en) 2011-01-24 2012-08-02 Universal Display Corporation Aza - dibenzothiophene, aza - dibenzofuran and aza - dibenzoselenophene derivatives for use in oled ' s
US8415031B2 (en) 2011-01-24 2013-04-09 Universal Display Corporation Electron transporting compounds
US10230057B2 (en) 2011-02-07 2019-03-12 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
US9373802B2 (en) 2011-02-07 2016-06-21 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
US9818958B2 (en) 2011-02-07 2017-11-14 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
US8754232B2 (en) 2011-02-23 2014-06-17 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US9005772B2 (en) 2011-02-23 2015-04-14 Universal Display Corporation Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
US9947880B2 (en) 2011-02-23 2018-04-17 Universal Display Corporation Organic electroluminescent materials and devices
US8748011B2 (en) 2011-02-23 2014-06-10 Universal Display Corporation Ruthenium carbene complexes for OLED material
US8871361B2 (en) 2011-02-23 2014-10-28 Universal Display Corporation Tetradentate platinum complexes
US8563737B2 (en) 2011-02-23 2013-10-22 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US8492006B2 (en) 2011-02-24 2013-07-23 Universal Display Corporation Germanium-containing red emitter materials for organic light emitting diode
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
US8580403B2 (en) 2011-03-08 2013-11-12 Kabushiki Kaisha Toshiba Organic light-emitting diode, display and illuminating device
US9972793B2 (en) 2011-03-08 2018-05-15 Universal Display Corporation Organic electroluminescent materials and devices
JP2012190843A (en) * 2011-03-08 2012-10-04 Toshiba Corp Organic electroluminescent element, display unit, and lighting device
US8580399B2 (en) 2011-04-08 2013-11-12 Universal Display Corporation Substituted oligoazacarbazoles for light emitting diodes
US9397312B2 (en) 2011-05-11 2016-07-19 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
US9537111B2 (en) 2011-05-11 2017-01-03 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, and organic electroluminescence device
US8564192B2 (en) 2011-05-11 2013-10-22 Universal Display Corporation Process for fabricating OLED lighting panels
CN103502233A (en) * 2011-05-11 2014-01-08 出光兴产株式会社 Novel compound, material for organic electroluminescence device, and organic electroluminescence device
WO2012153780A1 (en) * 2011-05-11 2012-11-15 出光興産株式会社 Novel compound, material for organic electroluminescence device, and organic electroluminescence device
US8432095B2 (en) 2011-05-11 2013-04-30 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
US8927308B2 (en) 2011-05-12 2015-01-06 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
US9450027B2 (en) 2011-05-12 2016-09-20 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
US9212197B2 (en) 2011-05-19 2015-12-15 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants
US9257658B2 (en) 2011-05-19 2016-02-09 Universal Display Corporation Method of making organic electroluminescent materials
US8795850B2 (en) 2011-05-19 2014-08-05 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology
US8748012B2 (en) 2011-05-25 2014-06-10 Universal Display Corporation Host materials for OLED
US10158089B2 (en) 2011-05-27 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US10079349B2 (en) 2011-05-27 2018-09-18 Universal Display Corporation Organic electroluminescent materials and devices
US9755164B2 (en) 2011-06-08 2017-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US9847495B2 (en) 2011-06-08 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9812656B2 (en) 2011-06-08 2017-11-07 Universal Display Corporation Organic electroluminescent materials and devices
US10297769B2 (en) 2011-06-08 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US9315724B2 (en) 2011-06-14 2016-04-19 Basf Se Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs
EP3415521A1 (en) 2011-06-14 2018-12-19 UDC Ireland Limited Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in oleds
US10340313B2 (en) 2011-06-17 2019-07-02 Universal Display Corporation Non-common capping layer on an organic device
US8884316B2 (en) 2011-06-17 2014-11-11 Universal Display Corporation Non-common capping layer on an organic device
US8659036B2 (en) 2011-06-17 2014-02-25 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
US9054343B2 (en) 2011-06-17 2015-06-09 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
US9252377B2 (en) 2011-07-14 2016-02-02 Universal Display Corporation Inorganic hosts in OLEDs
US9397310B2 (en) 2011-07-14 2016-07-19 Universal Display Corporation Organice electroluminescent materials and devices
US9647221B2 (en) 2011-07-14 2017-05-09 Universal Display Corporation Organic light-emitting devices
US9783564B2 (en) 2011-07-25 2017-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US10214551B2 (en) 2011-07-25 2019-02-26 Universal Display Corporation Organic electroluminescent materials and devices
US8409729B2 (en) 2011-07-28 2013-04-02 Universal Display Corporation Host materials for phosphorescent OLEDs
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants
US8926119B2 (en) 2011-08-04 2015-01-06 Universal Display Corporation Extendable light source with variable light emitting area
US9313857B2 (en) 2011-08-04 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US8552420B2 (en) 2011-08-09 2013-10-08 Universal Display Corporation OLED light panel with controlled brightness variation
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
US8652656B2 (en) 2011-11-14 2014-02-18 Universal Display Corporation Triphenylene silane hosts
US9142788B2 (en) 2011-11-14 2015-09-22 Universal Display Corporation Host materials for OLEDs
US9193745B2 (en) 2011-11-15 2015-11-24 Universal Display Corporation Heteroleptic iridium complex
US9217004B2 (en) 2011-11-21 2015-12-22 Universal Display Corporation Organic light emitting materials
US9512355B2 (en) 2011-12-09 2016-12-06 Universal Display Corporation Organic light emitting materials
US9455417B2 (en) 2011-12-13 2016-09-27 Universal Display Corporation Split electrode for organic devices
US9461254B2 (en) 2012-01-03 2016-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US8987451B2 (en) 2012-01-03 2015-03-24 Universal Display Corporation Synthesis of cyclometallated platinum(II) complexes
US9163174B2 (en) 2012-01-04 2015-10-20 Universal Display Corporation Highly efficient phosphorescent materials
US8969592B2 (en) 2012-01-10 2015-03-03 Universal Display Corporation Heterocyclic host materials
US9447113B2 (en) 2012-01-10 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US10211413B2 (en) 2012-01-17 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US9118017B2 (en) 2012-02-27 2015-08-25 Universal Display Corporation Host compounds for red phosphorescent OLEDs
US9054323B2 (en) 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US9548459B2 (en) 2012-03-15 2017-01-17 Universal Display Corporation Organic materials for organic light emitting devices
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
US8723209B2 (en) 2012-04-27 2014-05-13 Universal Display Corporation Out coupling layer containing particle polymer composite
US9184399B2 (en) 2012-05-04 2015-11-10 Universal Display Corporation Asymmetric hosts with triaryl silane side chains
US9773985B2 (en) 2012-05-21 2017-09-26 Universal Display Corporation Organic electroluminescent materials and devices
US9670404B2 (en) 2012-06-06 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9502672B2 (en) 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9725476B2 (en) 2012-07-09 2017-08-08 Universal Display Corporation Silylated metal complexes
US9231218B2 (en) 2012-07-10 2016-01-05 Universal Display Corporation Phosphorescent emitters containing dibenzo[1,4]azaborinine structure
EP3133079A1 (en) 2012-07-19 2017-02-22 UDC Ireland Limited Dinuclear metal complexes comprising carbene ligands and the use thereof in oleds
US9590196B2 (en) 2012-07-19 2017-03-07 Udc Ireland Limited Dinuclear metal complexes comprising carbene ligands and the use thereof in OLEDs
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9059412B2 (en) 2012-07-19 2015-06-16 Universal Display Corporation Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs
WO2014012972A1 (en) 2012-07-19 2014-01-23 Basf Se Dinuclear metal complexes comprising carbene ligands and the use thereof in oleds
US9663544B2 (en) 2012-07-25 2017-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US9627631B2 (en) 2012-07-30 2017-04-18 Universal Display Corporation Organic electroluminescent materials and devices
US9318710B2 (en) 2012-07-30 2016-04-19 Universal Display Corporation Organic electroluminescent materials and devices
CN103626784A (en) * 2012-08-24 2014-03-12 通用显示公司 Phosphorescent emitters with phenylimidazole ligands
WO2014030666A1 (en) 2012-08-24 2014-02-27 コニカミノルタ株式会社 Transparent electrode, electronic device, and method for manufacturing transparent electrode
US20140054563A1 (en) * 2012-08-24 2014-02-27 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US9978958B2 (en) 2012-08-24 2018-05-22 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US8952362B2 (en) 2012-08-31 2015-02-10 The Regents Of The University Of Michigan High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion
EP3318566A1 (en) 2012-09-20 2018-05-09 UDC Ireland Limited Azadibenzofurans for electronic applications
US10249827B2 (en) 2012-09-20 2019-04-02 Udc Ireland Limited Azadibenzofurans for electronic applications
US9287513B2 (en) 2012-09-24 2016-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US9312505B2 (en) 2012-09-25 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US8692241B1 (en) 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US20140131663A1 (en) * 2012-11-09 2014-05-15 Universal Display Corporation Iridium Complexes With Aza-Benzo Fused Ligands
US20140131676A1 (en) * 2012-11-09 2014-05-15 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US10033002B2 (en) 2012-11-09 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US9685617B2 (en) 2012-11-09 2017-06-20 Universal Display Corporation Organic electronuminescent materials and devices
US9634264B2 (en) 2012-11-09 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US8946697B1 (en) 2012-11-09 2015-02-03 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US9190623B2 (en) 2012-11-20 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10069090B2 (en) 2012-11-20 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US9512136B2 (en) 2012-11-26 2016-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US9166175B2 (en) 2012-11-27 2015-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US9670185B2 (en) 2012-12-07 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10069081B2 (en) 2012-12-07 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
JP2013138230A (en) * 2013-02-12 2013-07-11 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device, and luminaire
JP2013145890A (en) * 2013-02-12 2013-07-25 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device and lighting system
US10367154B2 (en) 2013-02-21 2019-07-30 Universal Display Corporation Organic electroluminescent materials and devices
US9935276B2 (en) 2013-02-21 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US8927749B2 (en) 2013-03-07 2015-01-06 Universal Display Corporation Organic electroluminescent materials and devices
US9419225B2 (en) 2013-03-14 2016-08-16 Universal Display Corporation Organic electroluminescent materials and devices
WO2014147134A1 (en) 2013-03-20 2014-09-25 Basf Se Azabenzimidazole carbene complexes as efficiency booster in oleds
US9997712B2 (en) 2013-03-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
WO2014157494A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Material for organic electroluminescent elements, organic electroluminescent element, display device and lighting device
WO2014157618A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Organic electroluminescent element, and lighting device and display device which are provided with same
WO2014177518A1 (en) 2013-04-29 2014-11-06 Basf Se Transition metal complexes with carbene ligands and the use thereof in oleds
JP2013157634A (en) * 2013-05-01 2013-08-15 Konica Minolta Inc Organic electroluminescent element material
US9537106B2 (en) 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US9735373B2 (en) 2013-06-10 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9673401B2 (en) 2013-06-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US10199581B2 (en) 2013-07-01 2019-02-05 Universal Display Corporation Organic electroluminescent materials and devices
EP3266789A1 (en) 2013-07-02 2018-01-10 UDC Ireland Limited Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes
WO2015000955A1 (en) 2013-07-02 2015-01-08 Basf Se Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes
US10121975B2 (en) 2013-07-03 2018-11-06 Universal Display Corporation Organic electroluminescent materials and devices
US9761807B2 (en) 2013-07-15 2017-09-12 Universal Display Corporation Organic light emitting diode materials
US9324949B2 (en) 2013-07-16 2016-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US9553274B2 (en) 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US9224958B2 (en) 2013-07-19 2015-12-29 Universal Display Corporation Organic electroluminescent materials and devices
EP3239161A1 (en) 2013-07-31 2017-11-01 UDC Ireland Limited Luminescent diazabenzimidazole carbene metal complexes
US10074806B2 (en) 2013-08-20 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices
US9831437B2 (en) 2013-08-20 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9932359B2 (en) 2013-08-30 2018-04-03 University Of Southern California Organic electroluminescent materials and devices
US10199582B2 (en) 2013-09-03 2019-02-05 University Of Southern California Organic electroluminescent materials and devices
US9735378B2 (en) 2013-09-09 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9748503B2 (en) 2013-09-13 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US10003034B2 (en) 2013-09-30 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9831447B2 (en) 2013-10-08 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9293712B2 (en) 2013-10-11 2016-03-22 Universal Display Corporation Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
US10128450B2 (en) 2013-10-23 2018-11-13 University Of Southern California Organic electroluminescent materials and devices
US9853229B2 (en) 2013-10-23 2017-12-26 University Of Southern California Organic electroluminescent materials and devices
WO2015063046A1 (en) 2013-10-31 2015-05-07 Basf Se Azadibenzothiophenes for electronic applications
US9306179B2 (en) 2013-11-08 2016-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US9647218B2 (en) 2013-11-14 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US10033000B2 (en) 2013-11-15 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US10056565B2 (en) 2013-11-20 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US10355227B2 (en) 2013-12-16 2019-07-16 Universal Display Corporation Metal complex for phosphorescent OLED
US10347851B2 (en) 2013-12-20 2019-07-09 Udc Ireland Limited Highly efficient OLED devices with very short decay times
US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10135008B2 (en) 2014-01-07 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US9978961B2 (en) 2014-01-08 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9755159B2 (en) 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
US9935277B2 (en) 2014-01-30 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
JP2015151352A (en) * 2014-02-13 2015-08-24 国立大学法人山形大学 Benzofuropyrimidine derivative, host material comprising the same and organic electroluminescent element using the same
US9590194B2 (en) 2014-02-14 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9847497B2 (en) 2014-02-18 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10003033B2 (en) 2014-02-18 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9502656B2 (en) 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9647217B2 (en) 2014-02-24 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9673407B2 (en) 2014-02-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9181270B2 (en) 2014-02-28 2015-11-10 Universal Display Corporation Method of making sulfide compounds
US9590195B2 (en) 2014-02-28 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9397309B2 (en) 2014-03-13 2016-07-19 Universal Display Corporation Organic electroluminescent devices
JP2014131079A (en) * 2014-03-13 2014-07-10 Konica Minolta Inc Material for organic electroluminescent element, organic electroluminescent element, illuminating device and display device
US10208026B2 (en) 2014-03-18 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US9748504B2 (en) 2014-03-25 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US10118939B2 (en) 2014-03-31 2018-11-06 Udc Ireland Limited Metal complexes, comprising carbene ligands having an o-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
US10370396B2 (en) 2014-03-31 2019-08-06 Udc Ireland Limited Metal complexes, comprising carbene ligands having an O-substituted non-cyclometallated aryl group and their use in organic light emitting diodes
US9862739B2 (en) 2014-03-31 2018-01-09 Udc Ireland Limited Metal complexes, comprising carbene ligands having an O-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
US9929353B2 (en) 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
JP2014170946A (en) * 2014-04-04 2014-09-18 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device and luminaire
JP2014158039A (en) * 2014-04-04 2014-08-28 Konica Minolta Inc Organic electroluminescent element material, organic electroluminescent element, display device and lighting system
US9691993B2 (en) 2014-04-09 2017-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US9905785B2 (en) 2014-04-14 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US10008679B2 (en) 2014-04-14 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US9847498B2 (en) 2014-04-14 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10256427B2 (en) 2014-04-15 2019-04-09 Universal Display Corporation Efficient organic electroluminescent devices
US9741941B2 (en) 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US10256419B2 (en) 2014-05-08 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10276805B2 (en) 2014-05-08 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10301338B2 (en) 2014-05-08 2019-05-28 Universal Display Corporation Organic electroluminescent materials and devices
US10263198B2 (en) 2014-05-08 2019-04-16 Universal Display Corporation Organic electroluminescent materials and devices
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US9911931B2 (en) 2014-06-26 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
WO2016016791A1 (en) 2014-07-28 2016-02-04 Idemitsu Kosan Co., Ltd (Ikc) 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds)
EP2982676A1 (en) 2014-08-07 2016-02-10 Idemitsu Kosan Co., Ltd. Benzimidazo[2,1-B]benzoxazoles for electronic applications
EP2993215A1 (en) 2014-09-04 2016-03-09 Idemitsu Kosan Co., Ltd. Azabenzimidazo[2,1-a]benzimidazoles for electronic applications
US10135007B2 (en) 2014-09-29 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10043987B2 (en) 2014-09-29 2018-08-07 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US9397302B2 (en) 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US9799838B2 (en) 2014-10-08 2017-10-24 Universal Display Corporation Fluorinated organic electroluminescent materials and devices
US9484541B2 (en) 2014-10-20 2016-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US20160118594A1 (en) * 2014-10-22 2016-04-28 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
JP2016082205A (en) * 2014-10-22 2016-05-16 三星ディスプレイ株式會社Samsung Display Co.,Ltd. Material for organic electroluminescent element and organic electroluminescent element including the same
US10084140B2 (en) * 2014-10-22 2018-09-25 Samsung Display Co., Ltd. Material for organic electroluminescent device and organic electroluminescent device using the same
JP2017533893A (en) * 2014-10-30 2017-11-16 エルジー・ケム・リミテッド Ring compounds and organic light emitting devices comprising the same
EP3015469A1 (en) 2014-10-30 2016-05-04 Idemitsu Kosan Co., Ltd. 5-((benz)imidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications
WO2016067261A1 (en) 2014-10-30 2016-05-06 Idemitsu Kosan Co., Ltd. 5-((benz)imidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications
US10038151B2 (en) 2014-11-12 2018-07-31 Universal Display Corporation Organic electroluminescent materials and devices
US9871212B2 (en) 2014-11-14 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
WO2016079667A1 (en) 2014-11-17 2016-05-26 Idemitsu Kosan Co., Ltd. Indole derivatives for electronic applications
US9761814B2 (en) 2014-11-18 2017-09-12 Universal Display Corporation Organic light-emitting materials and devices
WO2016079169A1 (en) 2014-11-18 2016-05-26 Basf Se Pt- or pd-carbene complexes for use in organic light emitting diodes
US9825260B2 (en) 2014-11-26 2017-11-21 Universal Display Corporation Emissive display with photo-switchable polarization
US9444075B2 (en) 2014-11-26 2016-09-13 Universal Display Corporation Emissive display with photo-switchable polarization
WO2016097983A1 (en) 2014-12-15 2016-06-23 Idemitsu Kosan Co., Ltd. 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (oleds)
EP3034506A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 4-functionalized carbazole derivatives for electronic applications
EP3034507A1 (en) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs)
US9680113B2 (en) 2014-12-17 2017-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US10000517B2 (en) 2014-12-17 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9450195B2 (en) 2014-12-17 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US10253252B2 (en) 2014-12-30 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US9312499B1 (en) 2015-01-05 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US9748500B2 (en) 2015-01-15 2017-08-29 Universal Display Corporation Organic light emitting materials
US9711730B2 (en) 2015-01-25 2017-07-18 Universal Display Corporation Organic electroluminescent materials and devices
WO2016125110A1 (en) 2015-02-06 2016-08-11 Idemitsu Kosan Co., Ltd. Bisimidazolodiazocines
EP3053918A1 (en) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd 2-carbazole substituted benzimidazoles for electronic applications
US10355222B2 (en) 2015-02-06 2019-07-16 Universal Display Corporation Organic electroluminescent materials and devices
EP3054498A1 (en) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd. Bisimidazodiazocines
US10177316B2 (en) 2015-02-09 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
EP3056498A1 (en) * 2015-02-13 2016-08-17 Samsung SDI Co., Ltd. Diazadibenzofurane and diazadibenzothiophene derivatives and their use in organic optoelectronic devices
CN105884803A (en) * 2015-02-13 2016-08-24 三星Sdi株式会社 Compound For Organic Optoelectronic Device And Application Thereof
KR101842584B1 (en) 2015-02-13 2018-03-27 삼성에스디아이 주식회사 Organic compound for optoelectric device and organic optoelectric device and display device
US10144867B2 (en) 2015-02-13 2018-12-04 Universal Display Corporation Organic electroluminescent materials and devices
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
EP3061759A1 (en) 2015-02-24 2016-08-31 Idemitsu Kosan Co., Ltd Nitrile substituted dibenzofurans
US10270046B2 (en) 2015-03-06 2019-04-23 Universal Display Corporation Organic electroluminescent materials and devices
US10388890B2 (en) 2015-03-11 2019-08-20 Universal Display Corporation Organic electroluminescent heterocyclic carbene metal complexes and devices containing the same
US9780316B2 (en) 2015-03-16 2017-10-03 Universal Display Corporation Organic electroluminescent materials and devices
EP3070144A1 (en) 2015-03-17 2016-09-21 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
US9911928B2 (en) 2015-03-19 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9871214B2 (en) 2015-03-23 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
EP3072943A1 (en) 2015-03-26 2016-09-28 Idemitsu Kosan Co., Ltd. Dibenzofuran/carbazole-substituted benzonitriles
US10297770B2 (en) 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
WO2016157113A1 (en) 2015-03-31 2016-10-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes
EP3075737A1 (en) 2015-03-31 2016-10-05 Idemitsu Kosan Co., Ltd Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes
US9478758B1 (en) 2015-05-08 2016-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US10109799B2 (en) 2015-05-21 2018-10-23 Universal Display Corporation Organic electroluminescent materials and devices
US10256411B2 (en) 2015-05-21 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10033004B2 (en) 2015-06-01 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
WO2016193243A1 (en) 2015-06-03 2016-12-08 Udc Ireland Limited Highly efficient oled devices with very short decay times
US9978956B2 (en) 2015-07-15 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US10181564B2 (en) 2015-08-26 2019-01-15 Universal Display Corporation Organic electroluminescent materials and devices
US10361381B2 (en) 2015-09-03 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
WO2017056055A1 (en) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes
EP3150604A1 (en) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes
EP3150606A1 (en) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes
WO2017056052A1 (en) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes
WO2017056053A1 (en) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes
US10177318B2 (en) 2015-10-29 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
WO2017078182A1 (en) 2015-11-04 2017-05-11 Idemitsu Kosan Co., Ltd. Benzimidazole fused heteroaryls
WO2017093958A1 (en) 2015-12-04 2017-06-08 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes
WO2017109727A1 (en) 2015-12-21 2017-06-29 Idemitsu Kosan Co., Ltd. Hetero-condensed phenylquinazolines and their use in electronic devices
WO2017109722A1 (en) 2015-12-21 2017-06-29 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic compounds and organic electroluminescence devices containing them
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
EP3200255A2 (en) 2016-01-06 2017-08-02 Konica Minolta, Inc. Organic electroluminescent element, method for producing organic electroluminescent element, display, and lighting device
US10388894B2 (en) 2016-03-11 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10276809B2 (en) 2016-04-05 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
WO2017178864A1 (en) 2016-04-12 2017-10-19 Idemitsu Kosan Co., Ltd. Seven-membered ring compounds
US9929360B2 (en) 2016-07-08 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US10153443B2 (en) 2016-07-19 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10205105B2 (en) 2016-08-15 2019-02-12 Universal Display Corporation Organic electroluminescent materials and devices
US10388892B2 (en) 2016-10-20 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10236458B2 (en) 2016-10-24 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10340464B2 (en) 2016-11-10 2019-07-02 Universal Display Corporation Organic electroluminescent materials and devices
US10153445B2 (en) 2016-11-21 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10388893B2 (en) 2017-02-24 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10381580B2 (en) 2018-01-03 2019-08-13 Universal Display Corporation Organic electroluminescent materials and devices

Also Published As

Publication number Publication date
JP5589251B2 (en) 2014-09-17

Similar Documents

Publication Publication Date Title
JP5983648B2 (en) The organic electroluminescence device, an organic electroluminescence element compound, the method of manufacturing the organic electroluminescence element, an illumination device and a display device
JP4697142B2 (en) The organic electroluminescent element, a display device and a lighting device
JP5493357B2 (en) The organic electroluminescent element, a display device and a lighting device
JP4858169B2 (en) The organic electroluminescence element
JP4862248B2 (en) The organic electroluminescence element, an illumination device and a display device
JP5181676B2 (en) The organic electroluminescent element, a display device and a lighting device
JP5573858B2 (en) The organic electroluminescent element, a display device and a lighting device
JP4626515B2 (en) The organic electroluminescent element and a display device
JP5125502B2 (en) The organic electroluminescence device material, an organic electroluminescence element
JP5493333B2 (en) The organic electroluminescent device, the white organic electroluminescence device, a display device and a lighting device
JP5011908B2 (en) The organic electroluminescent element, a display device and a lighting device
JP4894513B2 (en) The organic electroluminescence device material, an organic electroluminescence device, a display device and a lighting device
JP5194596B2 (en) The organic electroluminescent element, a display device and a lighting device
JP5683784B2 (en) The organic electroluminescent element, a display device and a lighting device
JP5321684B2 (en) The organic electroluminescent element, a display device, illumination device and condensed polycyclic heterocyclic compound
JP5516668B2 (en) The organic electroluminescent device material
JP4887731B2 (en) The organic electroluminescent element, a display device and a lighting device
JP4810669B2 (en) The organic electroluminescent element, a display device and a lighting device
JP5387563B2 (en) The organic electroluminescence device material, an organic electroluminescence device, a method of manufacturing the organic electroluminescence element, an illumination device and a display device
JP5076891B2 (en) The organic electroluminescence device material, an organic electroluminescence device, a display device and a lighting device
JP5653617B2 (en) The organic electroluminescence device, an organic electroluminescence device material, a display device and a lighting device
JP5672648B2 (en) The organic electroluminescent element, a display device and a lighting device
JP5099013B2 (en) The organic electroluminescence device material, an organic electroluminescence device, a display device and a lighting device
JP5522245B2 (en) The organic electroluminescence device material, an organic electroluminescence device, a display device and a lighting device
JP5304653B2 (en) The organic electroluminescent element, a display device and a lighting device

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20090914

RD02 Notification of acceptance of power of attorney

Free format text: JAPANESE INTERMEDIATE CODE: A7422

Effective date: 20110818

A977 Report on retrieval

Effective date: 20120330

Free format text: JAPANESE INTERMEDIATE CODE: A971007

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20120417

A521 Written amendment

Effective date: 20120605

Free format text: JAPANESE INTERMEDIATE CODE: A523

A131 Notification of reasons for refusal

Effective date: 20130305

Free format text: JAPANESE INTERMEDIATE CODE: A131

A521 Written amendment

Effective date: 20130501

Free format text: JAPANESE INTERMEDIATE CODE: A523

A02 Decision of refusal

Effective date: 20140114

Free format text: JAPANESE INTERMEDIATE CODE: A02

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20140404

A911 Transfer of reconsideration by examiner before appeal (zenchi)

Effective date: 20140411

Free format text: JAPANESE INTERMEDIATE CODE: A911

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20140701

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20140714

R150 Certificate of patent (=grant) or registration of utility model

Ref document number: 5589251

Free format text: JAPANESE INTERMEDIATE CODE: R150

Country of ref document: JP