JP2007001879A - 1, 9, 10-anthridine compound and organic light emitting device using the same - Google Patents
1, 9, 10-anthridine compound and organic light emitting device using the same Download PDFInfo
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- JP2007001879A JP2007001879A JP2005180392A JP2005180392A JP2007001879A JP 2007001879 A JP2007001879 A JP 2007001879A JP 2005180392 A JP2005180392 A JP 2005180392A JP 2005180392 A JP2005180392 A JP 2005180392A JP 2007001879 A JP2007001879 A JP 2007001879A
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- anthridine
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
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- 150000002894 organic compounds Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
本発明は、新規な有機化合物およびそれを用いた有機発光素子に関する。 The present invention relates to a novel organic compound and an organic light-emitting device using the same.
有機発光素子は、陽極と陰極間に蛍光性有機化合物または燐光性有機化合物を含む薄膜を挟持した素子である。各電極から電子およびホール（正孔）を注入することにより、蛍光性化合物または燐光性化合物の励起子を生成させ、この励起子が基底状態にもどる際に放射される光を利用する素子である。 An organic light emitting element is an element in which a thin film containing a fluorescent organic compound or a phosphorescent organic compound is sandwiched between an anode and a cathode. It is an element that uses light emitted when excitons of fluorescent compounds or phosphorescent compounds are generated by injecting electrons and holes (holes) from each electrode, and these excitons return to the ground state. .
有機発光素子における最近の進歩は著しく、低印加電圧で高輝度、発光波長の多様性、高速応答性、薄型、軽量の発光デバイス化が可能であることから、広汎な用途への可能性を示唆している。しかしながら、現状では発光効率などの初期特性や長時間の発光による輝度劣化などの耐久特性の更なる向上が必要である。これらの初期特性や耐久特性は、素子を構成するホール注入層、ホール輸送層、発光層、ホールブロック層、電子輸送層や電子注入層などのすべての層が起因している。 Recent progress in organic light-emitting devices is remarkable, suggesting the possibility of a wide range of applications because it is possible to make light-emitting devices with high brightness, variety of emission wavelengths, high-speed response, thin and light weight at low applied voltage. is doing. However, at present, it is necessary to further improve the initial characteristics such as light emission efficiency and the durability characteristics such as luminance deterioration due to long-time light emission. These initial characteristics and durability characteristics are attributed to all layers such as a hole injection layer, a hole transport layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer constituting the device.
これまで知られているホールブロック層、電子輸送層、電子注入層に用いる材料としては、フェナントロリン化合物、アルミニウムキノリノール錯体、オキサジアゾール化合物やトリアゾール化合物などが挙げられる。これらの材料を発光層または電子輸送層に用いた例としては、特許文献１〜９が挙げられるが、これらのＥＬ素子の初期特性および耐久特性は十分ではない。
Examples of materials used for the hole block layer, the electron transport layer, and the electron injection layer that have been known so far include phenanthroline compounds, aluminum quinolinol complexes, oxadiazole compounds, and triazole compounds. Examples of using these materials for the light-emitting layer or the electron transport layer include
本発明の目的は、新規な１，９，１０−アンスリジン化合物を提供することにある。
An object of the present invention is to provide a
また本発明の目的は、新規な１，９，１０−アンスリジン化合物を用い、高発光輝度で高発光効率な有機発光素子を提供することにある。さらに耐久性が高く、長時間の発光による輝度劣化が小さい有機発光素子を提供することにある。
Another object of the present invention is to provide an organic light-emitting device that uses a
また本発明の目的は、製造が容易でかつ比較的安価に作成可能な有機発光素子を提供することにある。 Another object of the present invention is to provide an organic light emitting device that can be easily manufactured and can be produced at a relatively low cost.
すなわち、本発明の１，９，１０−アンスリジン化合物は、下記一般式［Ｉ］〜［ＩＩＩ］で示されることを特徴とする。 That is, the 1,9,10-anthridine compound of the present invention is represented by the following general formulas [I] to [III].
（式中、Ｒ1〜Ｒ7は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基、置換あるいは無置換の縮合多環複素環基、置換あるいは無置換のアリールオキシ基、置換アミノ基、ハロゲン原子、トリフルオロメチル基、シアノ基から選ばれる基を表わし、同じであっても異なっていてもよい。但し、Ｒ1〜Ｒ7の少なくとも１つは、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基、置換あるいは無置換の縮合多環複素環基から選ばれる。） Wherein R 1 to R 7 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted Represents a group selected from a substituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted amino group, a halogen atom, a trifluoromethyl group, and a cyano group. These may be the same or different, provided that at least one of R 1 to R 7 is a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycycle. (Selected from an aromatic group, a substituted or unsubstituted condensed polycyclic heterocyclic group)
（式中、Ｒ13、Ｒ14は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基、置換あるいは無置換の縮合多環複素環基、置換あるいは無置換のアリールオキシ基、置換アミノ基、ハロゲン原子、トリフルオロメチル基、シアノ基から選ばれる基を表わし、同じであっても異なっていてもよい。 (Wherein R 13 and R 14 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted Represents a group selected from a substituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted amino group, a halogen atom, a trifluoromethyl group, and a cyano group. , May be the same or different.
Ａｒ3は、２価の置換あるいは無置換の芳香環基，２価の置換あるいは無置換の複素環基、２価の置換あるいは無置換の縮合多環芳香族基、２価の置換あるいは無置換の縮合多環複素環基から選ばれる基を表わす。） Ar 3 is a divalent substituted or unsubstituted aromatic ring group, a divalent substituted or unsubstituted heterocyclic group, a divalent substituted or unsubstituted condensed polycyclic aromatic group, a divalent substituted or unsubstituted Represents a group selected from the group consisting of condensed polycyclic heterocyclic groups. )
（式中、Ｒ15〜Ｒ17は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基、置換あるいは無置換の縮合多環複素環基、置換あるいは無置換のアリールオキシ基、置換アミノ基、ハロゲン原子、トリフルオロメチル基、シアノ基から選ばれる基を表わし、同じであっても異なっていてもよい。 Wherein R 15 to R 17 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted Represents a group selected from a substituted fused polycyclic aromatic group, a substituted or unsubstituted fused polycyclic heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted amino group, a halogen atom, a trifluoromethyl group, and a cyano group. , May be the same or different.
Ａｒ4は、３価の置換あるいは無置換の芳香環基，３価の置換あるいは無置換の複素環基、３価の置換あるいは無置換の縮合多環芳香族基、３価の置換あるいは無置換の縮合多環複素環基から選ばれる基を表わす。） Ar 4 is a trivalent substituted or unsubstituted aromatic ring group, a trivalent substituted or unsubstituted heterocyclic group, a trivalent substituted or unsubstituted condensed polycyclic aromatic group, a trivalent substituted or unsubstituted group Represents a group selected from the group consisting of condensed polycyclic heterocyclic groups. )
また、本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が上記１，９，１０−アンスリジン化合物の少なくとも一種を含有することを特徴とする。 The organic light-emitting device of the present invention is an organic light-emitting device having at least a layer containing a pair of electrodes composed of an anode and a cathode, and one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one of the containing layers contains at least one of the 1,9,10-anthridine compounds.
本発明の１，９，１０−アンスリジン化合物を用いた有機発光素子は、低い印加電圧で高輝度な発光が得られ、耐久性にも優れている。特に、本発明の１，９，１０−アンスリジン化合物を含有する有機層は、電子輸送層として優れ、かつ発光層としても優れている。 The organic light-emitting device using the 1,9,10-anthridine compound of the present invention can emit light with high luminance at a low applied voltage and has excellent durability. In particular, the organic layer containing the 1,9,10-anthridine compound of the present invention is excellent as an electron transport layer and also as a light emitting layer.
さらに、素子の作成も真空蒸着あるいはキャステイング法等を用いて作成可能であり、比較的安価で大面積の素子を容易に作成できる。 Furthermore, the device can be formed using vacuum deposition, casting method, or the like, and a device with a large area can be easily manufactured at a relatively low cost.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
まず、本発明の１，９，１０−アンスリジン化合物について説明する。 First, the 1,9,10-anthridine compound of the present invention will be described.
本発明の１，９，１０−アンスリジン化合物は、上記一般式［Ｉ］〜［ＩＩＩ］で示される。 The 1,9,10-anthridine compound of the present invention is represented by the above general formulas [I] to [III].
一般式［Ｉ］で示される１，９，１０−アンスリジン化合物としては、Ｒ2〜Ｒ6が、水素原子、置換あるいは無置換のアルキル基、ハロゲン原子、トリフルオロメチル基、シアノ基から選ばれる基を表わし、Ｒ1、Ｒ7が、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基、置換あるいは無置換の縮合多環複素環基、置換あるいは無置換のアリールオキシ基、置換アミノ基から選ばれる基を表わす化合物が好ましい。 In the 1,9,10-anthridine compound represented by the general formula [I], R 2 to R 6 are selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a halogen atom, a trifluoromethyl group, and a cyano group. R 1 and R 7 are a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, substituted or A compound representing a group selected from an unsubstituted condensed polycyclic heterocyclic group, a substituted or unsubstituted aryloxy group, and a substituted amino group is preferred.
上記一般式［Ｉ］〜［ＩＩＩ］における置換基の具体例を以下に示す。 Specific examples of the substituents in the general formulas [I] to [III] are shown below.
アルキル基としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｔｅｒ−ブチル基、オクチル基などが挙げられる。 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a ter-butyl group, and an octyl group.
アラルキル基としては、ベンジル基、フェネチル基などが挙げられる。 Examples of the aralkyl group include a benzyl group and a phenethyl group.
アリール基としては、フェニル基、ビフェニル基、ターフェニル基などが挙げられる。 Examples of the aryl group include a phenyl group, a biphenyl group, and a terphenyl group.
複素環基としては、チエニル基、ピロリル基、ピリジル基、ビピリジル基、ターピリジル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基などが挙げられる。 Examples of the heterocyclic group include thienyl group, pyrrolyl group, pyridyl group, bipyridyl group, terpyridyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, and thiadiazolyl group.
縮合多環芳香族基としては、フルオレニル基、ナフチル基、フルオランテニル基、アンスリル基、フェナンスリル基、ピレニル基、テトラセニル基、ペンタセニル基、ペリレニル基、トリフェニレニル基などが挙げられる。 Examples of the condensed polycyclic aromatic group include a fluorenyl group, a naphthyl group, a fluoranthenyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a perylenyl group, and a triphenylenyl group.
縮合多環複素環基としては、キノリル基、カルバゾリル基、アクリジニル基、フェナジル基、フェナントロリル基などが挙げられる。 Examples of the condensed polycyclic heterocyclic group include a quinolyl group, a carbazolyl group, an acridinyl group, a phenazyl group, and a phenanthroyl group.
アリールオキシ基としては、フェノキシル基、フルオレノキシル基、ナフトキシル基などが挙げられる。 Examples of the aryloxy group include a phenoxyl group, a fluorenoxyl group, and a naphthoxyl group.
置換アミノ基としては、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基、フルオレニルフェニルアミノ基、ジフルオレニル基、ナフチルフェニルアミノ基、ジナフチルアミノ基などが挙げられる。 Examples of substituted amino groups include dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, dianisolylamino group, fluorenylphenylamino group, difluorenyl group, naphthylphenylamino group, dinaphthylamino group. Etc.
ハロゲン原子としては、フッ素、塩素、臭素、ヨウ素などが挙げられる。 Examples of the halogen atom include fluorine, chlorine, bromine and iodine.
２価または３価の芳香環基、複素環基、縮合多環芳香族基、縮合多環複素環基としては、上記アリール基、複素環基、縮合多環芳香族基、縮合多環複素環基を２価または３価としたものなどが挙げられる。 Examples of the divalent or trivalent aromatic ring group, heterocyclic group, condensed polycyclic aromatic group, and condensed polycyclic heterocyclic group include the aryl group, heterocyclic group, condensed polycyclic aromatic group, and condensed polycyclic heterocyclic ring. Examples thereof include those in which the group is divalent or trivalent.
上記置換基が有してもよい置換基としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｔｅｒ−ブチル基、オクチル基などのアルキル基、ベンジル基、フェネチル基などのアラルキル基、フェニル基、ビフェニル基、ターフェニル基などのアリール基、チエニル基、ピロリル基、ピリジル基、ビピリジル基、ターピリジル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基などの複素環基、フルオレニル基、ナフチル基、フルオランテニル基、アンスリル基、フェナンスリル基、ピレニル基、テトラセニル基、ペンタセニル基、ペリレニル基、トリフェニレニル基などの縮合多環芳香族基、キノリル基、カルバゾリル基、アクリジニル基、フェナジル基、フェナントロリル基などの縮合多環複素環基、フェノキシル基、フルオレノキシル基、ナフトキシル基などのアリールオキシ基、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基、フルオレニルフェニルアミノ基、ジフルオレニル基、ナフチルフェニルアミノ基、ジナフチルアミノ基などの置換アミノ基、フッ素、塩素、臭素、ヨウ素などのハロゲン原子、トリフルオロメチル基、シアノ基などが挙げられる。 Examples of the substituent that the substituent may have include an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a ter-butyl group, and an octyl group, a benzyl group, Aralkyl groups such as phenethyl groups, aryl groups such as phenyl groups, biphenyl groups, and terphenyl groups, thienyl groups, pyrrolyl groups, pyridyl groups, bipyridyl groups, terpyridyl groups, oxazolyl groups, oxadiazolyl groups, thiazolyl groups, and thiadiazolyl groups Ring group, fluorenyl group, naphthyl group, fluoranthenyl group, anthryl group, phenanthryl group, pyrenyl group, tetracenyl group, pentacenyl group, perylenyl group, triphenylenyl group and other condensed polycyclic aromatic groups, quinolyl group, carbazolyl group, acridinyl Group, phenazyl group, phenanthryl group, etc. Fused polycyclic heterocyclic group, aryloxy group such as phenoxyl group, fluorenoxyl group, naphthoxyl group, dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, dianisolylamino group, full Examples thereof include substituted amino groups such as oleenylphenylamino group, difluorenyl group, naphthylphenylamino group and dinaphthylamino group, halogen atoms such as fluorine, chlorine, bromine and iodine, trifluoromethyl group and cyano group.
次に、本発明の１，９，１０−アンスリジン化合物の代表例を以下に挙げるが、本発明はこれらに限定されるものではない。 Next, typical examples of the 1,9,10-anthridine compound of the present invention are listed below, but the present invention is not limited thereto.
本発明の１，９，１０−アンスリジン化合物は、一般的に知られている方法で合成できる。例えば、Ｊ．Ｏｒｇ．Ｃｈｅｍ．，４６，８３３（１９８１）、Ｊ．Ｈｅｔｅｒｏｃｙｃｌ．Ｃｈｅｍ．，１３，９６１（１９７６）、Ｚ．Ｃｈｅｍ．１８，３８２（１９７８）などに記載の方法である。１，９，１０−アンスリジン化合物中間体を得て、さらにパラジウム触媒を用いたＳｕｚｕｋｉ Ｃｏｕｐｌｉｎｇ法（例えばＣｈｅｍ．Ｒｅｖ．，９５，２４５７，（１９９５）などの合成法で得ることができる。 The 1,9,10-anthridine compound of the present invention can be synthesized by a generally known method. For example, J. et al. Org. Chem. 46, 833 (1981); Heterocycl. Chem. , 13, 961 (1976), Z. Chem. 18, 382 (1978). A 1,9,10-anthridine compound intermediate can be obtained, and further obtained by a synthesis method such as Suzuki Coupling using a palladium catalyst (for example, Chem. Rev., 95, 2457, (1995)).
本発明の１，９，１０−アンスリジン化合物は、従来の化合物に比べ電子輸送性、発光性および耐久性の優れた化合物である。これは有機発光素子の有機化合物を含む層、特に、電子輸送層、発光層として有用である。また真空蒸着法や溶液塗布法などによって形成した層は結晶化などが起こりにくく経時安定性に優れている。特に、本発明の１，９，１０−アンスリジン化合物の中で、比較的ＨＯＭＯが低いものはホールブロック性が高く、ホールブロック層や電子輸送層として特に好ましい。 The 1,9,10-anthridine compound of the present invention is a compound having excellent electron transport properties, light emitting properties and durability compared to conventional compounds. This is useful as a layer containing an organic compound of an organic light emitting device, particularly as an electron transport layer and a light emitting layer. In addition, a layer formed by a vacuum deposition method or a solution coating method is hardly crystallized and has excellent stability over time. In particular, among the 1,9,10-anthridine compounds of the present invention, those having a relatively low HOMO have a high hole blocking property and are particularly preferable as a hole blocking layer and an electron transporting layer.
次に、本発明の有機発光素子について詳細に説明する。 Next, the organic light emitting device of the present invention will be described in detail.
本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に狭持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子である。そして、前記有機化合物を含む層の少なくとも一層が上記本発明の１，９，１０−アンスリジン化合物の少なくとも一種を含有する。 The organic light-emitting device of the present invention is an organic light-emitting device having at least a layer containing a pair of electrodes composed of an anode and a cathode and one or more organic compounds sandwiched between the pair of electrodes. At least one of the layers containing the organic compound contains at least one of the 1,9,10-anthridine compounds of the present invention.
本発明の有機発光素子は、１，９，１０−アンスリジン化合物の少なくとも一種を含有する層が、ホールブロック層、電子輸送層、発光層または電子注入層であることが好ましい。 In the organic light-emitting device of the present invention, the layer containing at least one 1,9,10-anthridine compound is preferably a hole block layer, an electron transport layer, a light-emitting layer, or an electron injection layer.
本発明の有機発光素子においては、本発明の１，９，１０−アンスリジン化合物を真空蒸着法や溶液塗布法により陽極及び陰極の間に形成することができる。その有機層の厚みは１０μｍより薄く、好ましくは０．５μｍ以下、より好ましくは０．０１〜０．５μｍの厚みに薄膜化することが好ましい。 In the organic light emitting device of the present invention, the 1,9,10-anthridine compound of the present invention can be formed between the anode and the cathode by a vacuum deposition method or a solution coating method. The thickness of the organic layer is less than 10 μm, preferably 0.5 μm or less, more preferably 0.01 to 0.5 μm.
図１〜図６に本発明の有機発光素子の好ましい例を示す。 1 to 6 show preferred examples of the organic light emitting device of the present invention.
図１は本発明の有機発光素子の一例を示す断面図である。図１は基板１上に陽極２、発光層３及び陰極４を順次設けた構成のものである。ここで使用する発光素子はそれ自体でホール輸送能、エレクトロン輸送能及び発光性の性能を単一で有している場合や、それぞれの特性を有する化合物を混ぜて使う場合に有用である。
FIG. 1 is a cross-sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an
図２は本発明の有機発光素子における他の例を示す断面図である。図２は基板１上に陽極２、ホール輸送層５、電子輸送層６及び陰極４を順次設けた構成のものである。この場合は発光物質はホール輸送性かあるいは電子輸送性のいづれかあるいは両方の機能を有している材料をそれぞれの層に用いる。そしてこの場合は発光性の無い単なるホール輸送物質あるいは電子輸送物質と組み合わせて用いる場合に有用である。また、この場合、発光層はホール輸送層５あるいは電子輸送層６のいずれかから成る。
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an
図３は本発明の有機発光素子における他の例を示す断面図である。図３は基板１上に陽極２、ホール輸送層５、発光層３，電子輸送層６及び陰極４を順次設けた構成のものである。これはキャリヤ輸送と発光の機能を分離したものである。そしてこれはホール輸送性、電子輸送性、発光性の各特性を有した化合物と適時組み合わせて用いられ極めて材料選択の自由度が増すとともに、発光波長を異にする種々の化合物が使用できる。そのため発光色相の多様化が可能になる。さらに、中央の発光層３に各キャリヤあるいは励起子を有効に閉じこめて発光効率の向上を図ることも可能になる。
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an
図４は本発明の有機発光素子における他の例を示す断面図である。図４は図３に対してホール注入層７を陽極２側に挿入した構成であり、陽極２とホール輸送層５の密着性改善あるいはホールの注入性改善に効果があり、低電圧化に効果的である。
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 4 shows a structure in which a
図５および図６は本発明の有機発光素子における他の例を示す断面図である。図５および図６は、図３および図４に対してホールあるいは励起子（エキシトン）を陰極側に抜けることを阻害する層（ホール／エキシトンブロッキング層８）がある。そしてこれらの図はこの層を発光層３、電子輸送層６間に挿入した構成である。イオン化ポテンシャルの非常に高い化合物をホール／エキシトンブロッキング層８として用いる事により、発光効率の向上に効果的な構成である。
5 and 6 are cross-sectional views showing other examples of the organic light-emitting device of the present invention. 5 and 6 have a layer (hole / exciton blocking layer 8) that blocks holes or excitons (excitons) from passing to the cathode side as compared to FIGS. In these figures, this layer is inserted between the light emitting
ただし、図１〜図６はあくまでごく基本的な素子構成であり、本発明の化合物を用いた有機発光素子の構成はこれらに限定されるものではない。例えば、電極と有機層界面に絶縁性層を設ける、接着層あるいは干渉層を設ける、ホール輸送層がイオン化ポテンシャルの異なる２層から構成される、など多様な層構成をとることができる。 However, FIGS. 1 to 6 are very basic device configurations, and the configuration of the organic light-emitting device using the compound of the present invention is not limited thereto. For example, various layer configurations such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or an interference layer, and the hole transport layer including two layers having different ionization potentials can be employed.
本発明の１，９，１０−アンスリジン化合物は、従来の化合物に比べ電子輸送性、発光性および耐久性の優れた化合物であり、図１〜図６のいずれの形態でも使用することができる。 The 1,9,10-anthridine compound of the present invention is a compound excellent in electron transporting property, light emitting property and durability as compared with conventional compounds, and can be used in any form of FIGS.
本発明の有機発光素子は、好ましくは電子輸送層、発光層の構成成分として本発明の１，９，１０−アンスリジン化合物を用いるものである。そしてこれまで知られているホール輸送性化合物、発光性化合物あるいは電子輸送性化合物などを必要に応じて一緒に使用することもできる。 The organic light emitting device of the present invention preferably uses the 1,9,10-anthridine compound of the present invention as a constituent component of the electron transport layer and the light emitting layer. In addition, a hole transporting compound, a light emitting compound, an electron transporting compound or the like known so far can be used together as necessary.
以下にこれらの化合物例を挙げる。 Examples of these compounds are given below.
本発明の有機発光素子において、本発明の１，９，１０−アンスリジン化合物を含有する層および他の有機化合物を含有する層は、一般には真空蒸着法あるいは、適当な溶媒に溶解させて塗布法により薄膜を形成する。特に塗布法で成膜する場合は、適当な結着樹脂と組み合わせて膜を形成することもできる。 In the organic light-emitting device of the present invention, the layer containing the 1,9,10-anthridine compound of the present invention and the layer containing another organic compound are generally applied by vacuum deposition or coating by dissolving in an appropriate solvent. To form a thin film. In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.
上記結着樹脂としては広範囲な結着性樹脂より選択でき、たとえばポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリアリレート樹脂、ポリスチレン樹脂、アクリル樹脂、メタクリル樹脂、ブチラール樹脂、ポリビニルアセタール樹脂、ジアリルフタレート樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、ポリスルホン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。また、これらは単独または共重合体ポリマーとして１種または２種以上混合してもよい。 The binder resin can be selected from a wide range of binder resins such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, diallyl phthalate resin. , Phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin and the like, but are not limited thereto. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer.
陽極材料としては仕事関数がなるべく大きなものがよく、例えば、金、銀、白金、ニッケル、パラジウム、コバルト、セレン、バナジウム等の金属単体あるいはこれらの合金、酸化錫、酸化亜鉛、酸化錫インジウム（ＩＴＯ），酸化亜鉛インジウム等の金属酸化物が使用できる。また、ポリアニリン、ポリピロール、ポリチオフェン、ポリフェニレンスルフィド等の導電性ポリマーも使用できる。これらの電極物質は単独で用いてもよく、複数併用することもできる。 As the anode material, a material having a work function as large as possible is preferable. For example, simple metals such as gold, silver, platinum, nickel, palladium, cobalt, selenium, vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide (ITO) ), Metal oxides such as indium zinc oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination.
一方、陰極材料としては仕事関数の小さなものがよく、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウム、アルミニウム、インジウム、銀、鉛、錫、クロム等の金属単体あるいは複数の合金またはこれらの塩などを用いることができる。酸化錫インジウム（ＩＴＯ）等の金属酸化物の利用も可能である。また、陰極は一層構成でもよく、多層構成をとることもできる。 On the other hand, the cathode material preferably has a small work function, such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver, lead, tin, chromium, or a simple metal or a plurality of alloys or salts thereof. Can be used. A metal oxide such as indium tin oxide (ITO) can also be used. Further, the cathode may have a single layer structure or a multilayer structure.
本発明で用いる基板としては、特に限定するものではないが、金属製基板、セラミックス製基板等の不透明性基板、ガラス、石英、プラスチックシート等の透明性基板が用いられる。また、基板にカラーフィルター膜、蛍光色変換フィルター膜、誘電体反射膜などを用いて発色光をコントロールする事も可能である。 Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.
なお、作成した素子に対して、酸素や水分等との接触を防止する目的で保護層あるいは封止層を設けることもできる。保護層としては、ダイヤモンド薄膜、金属酸化物、金属窒化物等の無機材料膜、フッソ樹脂、ポリパラキシレン、ポリエチレン、シリコーン樹脂、ポリスチレン樹脂等の高分子膜、さらには、光硬化性樹脂等が挙げられる。また、ガラス、気体不透過性フィルム、金属などをカバーし、適当な封止樹脂により素子自体をパッケージングすることもできる。 Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of protective layers include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluorine resins, polyparaxylene, polyethylene, silicone resins, and polystyrene resins, and photocurable resins. Can be mentioned. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.
以下、実施例により本発明をさらに具体的に説明していくが、本発明はこれらに限定されるものではない。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
＜合成例１［例示化合物Ｎｏ．５の合成］＞ <Synthesis Example 1 [Exemplary Compound No. Synthesis of 5] >>
Ｊ．Ｏｒｇ．Ｃｈｅｍ．，４６，８３３（１９８１）に記載の合成法に準じ、２，８−ジクロロ−１，９，１０−アンスリジン［４］（白色結晶）を［１］からのトータル収率１１％で得た。 J. et al. Org. Chem. 46,833 (1981), 2,8-dichloro-1,9,10-anthridine [4] (white crystals) was obtained in a total yield of 11% from [1].
５００ｍｌ三ツ口フラスコに、２，８−ジクロロ−１，９，１０−アンスリジン［４］１．０ｇ（４．００ｍｍｏｌ）、９，９−ジメチルフルオレン−２−ボロン酸［５］２．９ｇ（１２．０ｍｍｏｌ）、トルエン１６０ｍｌおよびエタノール８０ｍｌを入れ、窒素雰囲気中、室温で攪拌下、炭酸ナトリウム１６ｇ／水８０ｍｌの水溶液を滴下した。次いでテトラキス（トリフェニルホスフィン）パラジウム（０）０．２３ｇ（０．２０ｍｍｏｌ）を添加した。室温で３０分攪拌した後７７度に昇温し４時間攪拌した。反応後、有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（クロロホルム展開溶媒）で精製し、例示化合物Ｎｏ．５（白色結晶）１．８ｇ（収率８０％）を得た。 In a 500 ml three-necked flask, 1.0 g (4.00 mmol) of 2,8-dichloro-1,9,10-anthridine [4] and 2.9 g of 9,9-dimethylfluorene-2-boronic acid [5] (12. 0 mmol), 160 ml of toluene and 80 ml of ethanol were added, and an aqueous solution of 16 g of sodium carbonate / 80 ml of water was added dropwise with stirring at room temperature in a nitrogen atmosphere. Next, 0.23 g (0.20 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. After stirring at room temperature for 30 minutes, the temperature was raised to 77 degrees and stirred for 4 hours. After the reaction, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (chloroform developing solvent). Thus, 1.8 g (yield 80%) of 5 (white crystals) was obtained.
＜合成例２［例示化合物Ｎｏ．９の合成］＞ <Synthesis Example 2 [Exemplary Compound No. Synthesis of 9] >>
５００ｍｌ三ツ口フラスコに、２，８−ジクロロ−１，９，１０−アンスリジン［４］１．０ｇ（４．００ｍｍｏｌ）、フェナンスレン−９−ボロン酸［６］２．７ｇ（１２．２ｍｍｏｌ）、トルエン１６０ｍｌおよびエタノール８０ｍｌを入れた。窒素雰囲気中、室温で攪拌下、炭酸ナトリウム１６ｇ／水８０ｍｌの水溶液を滴下し、次いでテトラキス（トリフェニルホスフィン）パラジウム（０）０．２３ｇ（０．２０ｍｍｏｌ）を添加した。室温で３０分攪拌した後７７度に昇温し４時間攪拌した。反応後有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（クロロホルム展開溶媒）で精製し、例示化合物Ｎｏ．９（白色結晶）１．６ｇ（収率７３％）を得た。 In a 500 ml three-necked flask, 1.0 g (4.00 mmol) of 2,8-dichloro-1,9,10-anthridine [4], 2.7 g (12.2 mmol) of phenanthrene-9-boronic acid [6], 160 ml of toluene. And 80 ml of ethanol. While stirring at room temperature in a nitrogen atmosphere, an aqueous solution of 16 g of sodium carbonate / 80 ml of water was added dropwise, and then 0.23 g (0.20 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. After stirring at room temperature for 30 minutes, the temperature was raised to 77 degrees and stirred for 4 hours. After the reaction, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (chloroform developing solvent). 1.6 g (yield 73%) of 9 (white crystals) was obtained.
＜合成例３［例示化合物Ｎｏ．２２の合成］＞ <Synthesis Example 3 [Exemplary Compound No. Synthesis of 22] >>
５００ｍｌ三ツ口フラスコに、２，８−ジクロロ−１，９，１０−アンスリジン［４］５．０ｇ（２０．０ｍｍｏｌ）、フェニルボロン酸２．０ｇ（１６．０ｍｍｏｌ）、トルエン２００ｍｌおよびエタノール１００ｍｌを入れた。窒素雰囲気中、室温で攪拌下、炭酸ナトリウム３０ｇ／水１５０ｍｌの水溶液を滴下し、次いでテトラキス（トリフェニルホスフィン）パラジウム（０）１．１６ｇ（１．００ｍｍｏｌ）を添加した。室温で３０分攪拌した後７７度に昇温し１時間攪拌した。反応後有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（クロロホルム展開溶媒）で精製し、２−クロロ−８−フェニル−１，９，１０−アンスリジン［７］（白色結晶）１．８ｇ（収率３１％）を得た。 A 500 ml three-necked flask was charged with 5.0 g (20.0 mmol) of 2,8-dichloro-1,9,10-anthridine [4], 2.0 g (16.0 mmol) of phenylboronic acid, 200 ml of toluene and 100 ml of ethanol. . An aqueous solution of 30 g of sodium carbonate / 150 ml of water was added dropwise with stirring at room temperature in a nitrogen atmosphere, and then 1.16 g (1.00 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. After stirring at room temperature for 30 minutes, the temperature was raised to 77 degrees and stirred for 1 hour. After the reaction, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (chloroform developing solvent) to give 2-chloro-8-phenyl-1,9,10-anthridine [7] (white crystals) 1 0.8 g (yield 31%) was obtained.
２００ｍｌ三ツ口フラスコに、２−クロロ−８−フェニル−１，９，１０−アンスリジン［７］１．０ｇ（３．４４ｍｍｏｌ）、４，４‘−ビフェニルジボロニックアシッド［８］０．３３ｇ（１．３７ｍｍｏｌ）、トルエン６０ｍｌおよびエタノール３０ｍｌを入れた。窒素雰囲気中、室温で攪拌下、炭酸ナトリウム６ｇ／水３０ｍｌの水溶液を滴下し、次いでテトラキス（トリフェニルホスフィン）パラジウム（０）０．０８ｇ（０．０７ｍｍｏｌ）を添加した。室温で３０分攪拌した後７７度に昇温し４時間攪拌した。反応後有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（クロロホルム展開溶媒）で精製し、例示化合物Ｎｏ．２２（黄色結晶）０．６８ｇ（収率７５％）を得た。 In a 200 ml three-necked flask, 1.0 g (3.44 mmol) of 2-chloro-8-phenyl-1,9,10-anthridine [7] and 0.33 g of 4,4′-biphenyldiboronic acid [8] (1 37 mmol), 60 ml of toluene and 30 ml of ethanol. While stirring at room temperature in a nitrogen atmosphere, an aqueous solution of 6 g of sodium carbonate / 30 ml of water was added dropwise, and then 0.08 g (0.07 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. After stirring at room temperature for 30 minutes, the temperature was raised to 77 degrees and stirred for 4 hours. After the reaction, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (chloroform developing solvent). Thus, 0.68 g (yield 75%) of 22 (yellow crystals) was obtained.
＜実施例１＞
図３に示す構造の素子を作成した。
<Example 1>
An element having the structure shown in FIG. 3 was prepared.
基板１としてのガラス基板上に、陽極２としての酸化錫インジウム（ＩＴＯ）をスパッタ法にて１２０ｎｍの膜厚で成膜したものを透明導電性支持基板として用いた。これをアセトン、イソプロピルアルコール（ＩＰＡ）で順次超音波洗浄し、次いでＩＰＡで煮沸洗浄後乾燥した。さらに、ＵＶ／オゾン洗浄したものを透明導電性支持基板として使用した。
What formed indium tin oxide (ITO) as an
透明導電性支持基板上に下記構造式で示される化合物のクロロホルム溶液をスピンコート法により２０ｎｍの膜厚で成膜しホール輸送層５を形成した。
A
さらに下記構造式で示されるＩｒ錯体およびＣＢＰ（重量比８：１００）を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Further, an Ir complex represented by the following structural formula and CBP (weight ratio 8: 100) were formed into a film with a thickness of 20 nm by a vacuum deposition method to form the
さらに、例示化合物Ｎｏ．１を真空蒸着法により３０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Furthermore, Exemplified Compound No. 1 was formed into a film with a thickness of 30 nm by a vacuum vapor deposition method to form an
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に真空蒸着法により厚さ５０ｎｍの金属層膜を形成し、さらに真空蒸着法により厚さ１５０ｎｍのアルミニウム層を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
Next, a metal layer film having a thickness of 50 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%) as the
さらに、窒素雰囲気中で保護用ガラス板をかぶせ、アクリル樹脂系接着材で封止した。 Further, a protective glass plate was placed in a nitrogen atmosphere and sealed with an acrylic resin adhesive.
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、１０Ｖの直流電圧を印加すると２２ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、５１００ｃｄ／ｍ2の輝度で緑色の発光が観測された。 When a 10V DC voltage was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, the current flowed at a current density of 22 mA / cm 2. A green light emission was observed at a luminance of 5100 cd / m 2 .
さらに、電流密度を６．０ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度９１０ｃｄ／ｍ2から１００時間後８７０ｃｄ／ｍ2と輝度劣化は小さかった。 Further, when a voltage was applied for 100 hours while maintaining the current density at 6.0 mA / cm 2 , the luminance deterioration was small, that is, 870 cd / m 2 after 100 hours from the initial luminance of 910 cd / m 2 .
＜実施例２〜１２＞
例示化合物Ｎｏ．１に代えて、表１に示す化合物を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。結果を表１に示す。
<Examples 2 to 12>
Exemplified Compound No. A device was prepared in the same manner as in Example 1 except that the compounds shown in Table 1 were used in place of 1, and the same evaluation was performed. The results are shown in Table 1.
＜比較例１〜３＞
例示化合物Ｎｏ．１に代えて、下記構造式で示される化合物を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。結果を表１に示す。
<Comparative Examples 1-3>
Exemplified Compound No. A device was prepared in the same manner as in Example 1 except that a compound represented by the following structural formula was used instead of 1, and the same evaluation was performed. The results are shown in Table 1.
＜実施例１３＞
図３に示す構造の素子を作成した。
<Example 13>
An element having the structure shown in FIG. 3 was prepared.
実施例１と同様に、透明導電性支持基板上にホール輸送層５を形成した。
In the same manner as in Example 1, a
さらに下記構造式で示されるフルオレン化合物を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Further, a fluorene compound represented by the following structural formula was formed into a film with a thickness of 20 nm by a vacuum vapor deposition method to form the
さらに例示化合物Ｎｏ．５を真空蒸着法により２０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Furthermore, Exemplified Compound No. 5 was formed into a film with a thickness of 20 nm by a vacuum evaporation method, and an
次に、実施例１と同様にして、陰極４を形成後、封止した。
Next, in the same manner as in Example 1, the
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、５Ｖの直流電圧を印加すると７５ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、３５００ｃｄ／ｍ2の輝度で青色の発光が観測された。 When a 5V DC voltage was applied to the device obtained in this manner, with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, the current flowed at a current density of 75 mA / cm 2. A blue emission was observed at a luminance of 3500 cd / m 2 .
さらに、電流密度を３０ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度１８００ｃｄ／ｍ2から１００時間後１２００ｃｄ／ｍ2と輝度劣化は小さかった。 Further, when a voltage was applied for 100 hours while maintaining the current density at 30 mA / cm 2 , the luminance deterioration was small, from the initial luminance of 1800 cd / m 2 to 1200 cd / m 2 after 100 hours.
＜実施例１４〜２２＞
例示化合物Ｎｏ．５に代えて、表２に示す化合物を用いた他は実施例１３と同様に素子を作成し、同様な評価を行った。結果を表２に示す。
<Examples 14 to 22>
Exemplified Compound No. A device was prepared in the same manner as in Example 13 except that the compounds shown in Table 2 were used in place of 5, and the same evaluation was performed. The results are shown in Table 2.
＜比較例４〜６＞
例示化合物Ｎｏ．５に代えて、比較化合物Ｎｏ．１、２、３を用いた他は実施例１３と同様に素子を作成し、同様な評価を行った。結果を表２に示す。
<Comparative Examples 4-6>
Exemplified Compound No. In place of Comparative compound No. 5 A device was prepared in the same manner as in Example 13 except that 1, 2, and 3 were used, and the same evaluation was performed. The results are shown in Table 2.
＜実施例２３＞
図２に示す構造の素子を作成した。
<Example 23>
An element having the structure shown in FIG. 2 was produced.
実施例１と同様に、透明導電性支持基板上にホール輸送層５を形成した。
In the same manner as in Example 1, a
さらに例示化合物Ｎｏ．３を真空蒸着法により４０ｎｍの膜厚で成膜し発光層兼電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Furthermore, Exemplified Compound No. 3 was formed into a film having a thickness of 40 nm by a vacuum evaporation method to form a light emitting layer /
次に、実施例１と同様にして、陰極４を形成後、封止した。
Next, in the same manner as in Example 1, the
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、５Ｖの直流電圧を印加すると４０ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、１６００ｃｄ／ｍ2の輝度で青色の発光が観測された。 When a 5V DC voltage was applied to the device thus obtained with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, the current was applied at a current density of 40 mA / cm 2. A blue light emission was observed at a luminance of 1600 cd / m 2 .
さらに、電流密度を３０ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度１０００ｃｄ／ｍ2から１００時間後７５０ｃｄ／ｍ2と輝度劣化は小さかった。 Further, when a voltage was applied for 100 hours while a current density was kept to 30 mA / cm 2, after the initial luminance 1000 cd / m 2 100 hours 750 cd / m 2 and luminance degradation was small.
＜実施例２４〜２７＞
例示化合物Ｎｏ．３に代えて、表３に示す化合物を用いた他は実施例２３と同様に素子を作成し、同様な評価を行った。結果を表３に示す。
<Examples 24-27>
Exemplified Compound No. A device was prepared in the same manner as in Example 23 except that the compounds shown in Table 3 were used in place of 3, and the same evaluation was performed. The results are shown in Table 3.
＜比較例７〜９＞
例示化合物Ｎｏ．３に代えて、比較化合物Ｎｏ．１、２、３を用いた他は実施例２３と同様に素子を作成し、同様な評価を行った。結果を表３に示す。
<Comparative Examples 7-9>
Exemplified Compound No. In place of Comparative compound No. 3 A device was prepared in the same manner as in Example 23 except that 1, 2, and 3 were used, and the same evaluation was performed. The results are shown in Table 3.
１ 基板
２ 陽極
３ 発光層
４ 陰極
５ ホール輸送層
６ 電子輸送層
７ ホール注入層
８ ホール／エキシトンブロッキング層
DESCRIPTION OF
Claims (6)
Ａｒ3は、２価の置換あるいは無置換の芳香環基，２価の置換あるいは無置換の複素環基、２価の置換あるいは無置換の縮合多環芳香族基、２価の置換あるいは無置換の縮合多環複素環基から選ばれる基を表わす。） A 1,9,10-anthridine compound represented by the following general formula [II]:
Ar 3 is a divalent substituted or unsubstituted aromatic ring group, a divalent substituted or unsubstituted heterocyclic group, a divalent substituted or unsubstituted condensed polycyclic aromatic group, a divalent substituted or unsubstituted Represents a group selected from the group consisting of condensed polycyclic heterocyclic groups. )
Ａｒ4は、３価の置換あるいは無置換の芳香環基，３価の置換あるいは無置換の複素環基、３価の置換あるいは無置換の縮合多環芳香族基、３価の置換あるいは無置換の縮合多環複素環基から選ばれる基を表わす。） A 1,9,10-anthridine compound represented by the following general formula [III]:
Ar 4 is a trivalent substituted or unsubstituted aromatic ring group, a trivalent substituted or unsubstituted heterocyclic group, a trivalent substituted or unsubstituted condensed polycyclic aromatic group, a trivalent substituted or unsubstituted group Represents a group selected from the group consisting of condensed polycyclic heterocyclic groups. )
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8277957B2 (en) | 2009-08-28 | 2012-10-02 | Industrial Technology Research Institute | Quinoxaline derivatives and organic light-emitting diodes comprising the same |
| US8486544B2 (en) | 2009-08-28 | 2013-07-16 | Industrial Technology Research Institute | Quinoxaline derivatives and organic light-emitting diodes comprising the same |
| US11326096B2 (en) * | 2018-12-17 | 2022-05-10 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Red light thermally activated delayed fluorescence material, method for preparing the same, and organic light emitting diode device |
-
2005
- 2005-06-21 JP JP2005180392A patent/JP2007001879A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8277957B2 (en) | 2009-08-28 | 2012-10-02 | Industrial Technology Research Institute | Quinoxaline derivatives and organic light-emitting diodes comprising the same |
| US8486544B2 (en) | 2009-08-28 | 2013-07-16 | Industrial Technology Research Institute | Quinoxaline derivatives and organic light-emitting diodes comprising the same |
| US11326096B2 (en) * | 2018-12-17 | 2022-05-10 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Red light thermally activated delayed fluorescence material, method for preparing the same, and organic light emitting diode device |
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