JP2013080898A - Organic light-emitting element and display device using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic light-emitting element which is further improved in luminous efficiency and is capable of achieving higher efficiency and a longer service life.SOLUTION: The organic light-emitting element including a light-emitting layer (50) formed of an organic layer between a pair of electrodes (20, 70) is characterized in that: a host material of the light-emitting layer is an organic metal complex containing beryllium; and a guest material of the light-emitting layer is a phosphorescent platinum complex.

Description

  The present invention relates to an organic light emitting element and a display device using the same, and more particularly to an organic light emitting element including an organic light emitting layer between a pair of electrodes and a display device using the same.

  Conventionally, in an organic light emitting device having a light emitting layer composed of a material having two or more components between opposed electrodes, the main constituent material of the light emitting layer is a zinc complex and the sub constituent material is a phosphorescent platinum complex. A light emitting element is known (see, for example, Patent Document 1).

  In the light emitting device described in Patent Document 1, a highly efficient and long-life red light emitting device is realized by using a Zn complex or a guest Pt complex as a host of the light emitting layer.

JP 2008-103535 A

H. Kanno et al., APPLIED PHYSICS LETTERS 90, 123509 (2007). F. Lindla et al., APPLIED PHYSICS LETTERS 98, 173304 (2011). S. Tokito et al., APPLIED PHYSICS LETTERS 83, 569 (2003). Y. Zheng et al., APPLIED PHYSICS LETTERS 92, 223301 (2008).

  However, there is a demand for higher efficiency and longer life for the organic light emitting device, and an organic light emitting device having higher light emission efficiency than the light emitting device described in Patent Document 1 is required.

  Therefore, an object of the present invention is to provide an organic light emitting device that can further improve the light emission efficiency and realize higher efficiency and longer life.

In order to achieve the above object, one aspect of the organic light emitting device according to the present invention is an organic light emitting device including a light emitting layer composed of an organic layer between a pair of electrodes.
The host material of the light emitting layer is an organometallic complex containing beryllium, and the guest material is a phosphorescent platinum complex.

  The host material is preferably a beryllium complex represented by the following general formula (1).

（式中、環Ｅ、環Ｆ及び環Ｇは、夫々独立して置換基を有していてもよい芳香環又は芳香族複素環を示す。ｎは０又は１を表す。）
また、前記ホスト材料が、下記一般式（２）で表されるベリリウム錯体であることが好ましい。

(In the formula, ring E, ring F and ring G each independently represent an aromatic ring or an aromatic heterocyclic ring which may have a substituent. N represents 0 or 1.)
The host material is preferably a beryllium complex represented by the following general formula (2).

（式中、環Ｈ及び環Ｊは、夫々独立して置換基を有していてもよい芳香環又は芳香族複素環を示す。ｎは０又は１を表す。）
また、前記ゲスト材料が、下記一般式（３）で表される燐光発光性白金錯体であることが好ましい。

(In the formula, each of ring H and ring J independently represents an aromatic ring or an aromatic heterocyclic ring which may have a substituent. N represents 0 or 1.)
The guest material is preferably a phosphorescent platinum complex represented by the following general formula (3).

（式中、Ｗ^１、Ｗ^２、Ｗ^３及びＷ^４は、夫々白金原子に配位又は結合する部位を表す。Ｖ^１、Ｖ^２及びＶ^３は夫々二価の原子（団）、単結合又は二重結合を表す。破線で表される結合は単結合又は二重結合を、実線で表される結合は配位結合又は共有結合を表す。）
また、前記ゲスト材料が、下記一般式（４）で表される燐光発光性白金錯体であることがより好ましい。

(W ¹ , W ² , W ^3, and W ⁴ each represent a site that is coordinated or bonded to a platinum atom. V ¹ , V ^2, and V ³ are each a divalent atom (group), a single bond. (The bond represented by a broken line represents a single bond or a double bond, and the bond represented by a solid line represents a coordination bond or a covalent bond.)
The guest material is more preferably a phosphorescent platinum complex represented by the following general formula (4).

（式中、環Ａ、環Ｂ、環Ｃ及び環Ｄは、この中の何れか２つの環が置換基を有していてもよい含窒素複素環を示し、残りの２つの環が置換基を有していてもよい芳香環又は芳香族複素環を示す。環Ａ、環Ｂ、環Ｃ、環Ｄは夫々が置換基を介して縮合して環を形成してもよい。環Ａ、環Ｂ、環Ｃ、環Ｄは該環において複数の置換基同士が縮合してさらに環を形成してもよい。Ｘ^１、Ｘ^２、Ｘ^３及びＸ^４は、この中の何れか２つが白金原子に配位結合する窒素原子を示し、残りの２つは炭素原子又は窒素原子を表す。Ｙ^１、Ｙ^２、Ｙ^３、Ｙ^４、Ｙ^５及びＹ^６は夫々独立して炭素又は窒素原子を示す。Ｑ^１、Ｑ^２及びＱ^３は、夫々独立して二価の原子（団）又は結合手を示す。Ｑ^１と環Ａ及び環Ｂ、Ｑ^２と環Ａ及び環Ｃ、Ｑ^３と環Ｂ及び環Ｄは夫々が置換基を介して縮合して環を形成してもよい。Ｚ^１、Ｚ^２、Ｚ^３及びＺ^４は、いずれか２つが配位結合手を示し、残りの２つが共有結合手、酸素原子又は硫黄原子を示す。）
また、前記ホスト材料は、ベリリウム錯体以外の金属錯体を含んでもよい。

(In the formula, ring A, ring B, ring C and ring D are nitrogen-containing heterocycles in which any two of the rings may have a substituent, and the remaining two rings are substituents. The ring A, ring B, ring C, and ring D may each be condensed via a substituent to form a ring. Ring B, Ring C, and Ring D may further form a ring by condensing a plurality of substituents in the ring, and X ¹ , X ² , X ³ and X ⁴ are any two of them 2 represents a nitrogen atom coordinated to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom, and Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ and Y ⁶ are each independently carbon or nitrogen. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (group) or bond, Q ¹ and ring A and ring B, Q ² and ring A and ring C, Q ³ and ring And ring D may form a ring condensed via the respective substituents .Z ^{1, Z 2,} Z ³ and Z ^4, any two of indicates coordination bond, but the remaining two (Indicates a covalent bond, oxygen atom or sulfur atom.)
The host material may include a metal complex other than the beryllium complex.

The pair of electrodes includes an anode provided on a substrate, and a cathode disposed with a gap from the anode,
A hole transport layer between the light emitting layer and the anode;
You may have an electron carrying layer between the said light emitting layer and the said cathode.

A display device according to another aspect of the present invention includes a display element including the organic light-emitting element as a pixel;
Drive means for driving the display element.

  According to the present invention, highly efficient light emission and a long life can be realized.

It is the cross-sectional block diagram which showed an example of the organic light emitting element which concerns on Embodiment 1 of this invention. FIG. 6 is a graph showing luminance attenuation characteristics of the organic light emitting device according to Example 1 and the organic light emitting device according to Comparative Example 3. It is the figure which showed the measurement result of Example 3. It is the figure which showed the applied voltage-luminance characteristic of the organic light emitting element which concerns on Example 6 and Comparative Example 7. FIG. It is the figure which showed the applied voltage-current density characteristic of the organic light emitting element which concerns on Example 6 and Comparative Example 7. FIG. 6 is a graph showing current density-external quantum efficiency characteristics of organic light emitting devices according to Example 6 and Comparative Example 7. FIG. It is the figure which showed the spectral characteristic of the organic light emitting element which concerns on Example 6 and Comparative Example 7. It is the figure which showed the display apparatus which concerns on Embodiment 2 of this invention.

  DESCRIPTION OF EMBODIMENTS Hereinafter, embodiments for carrying out the present invention will be described with reference to the drawings.

  [Embodiment 1]

  FIG. 1 is a cross-sectional configuration diagram illustrating an example of an organic light-emitting device according to Embodiment 1 of the present invention. 1, the organic light emitting device according to Embodiment 1 includes a substrate 10, an ITO (Indium Tin Oxide) electrode 20, a hole injection layer 30, a hole transport layer 40, and a light emitting layer 50. The electron transport layer 60 and the electrode layer 70 are included.

  In the organic light emitting device according to the first embodiment, the ITO electrode 20, the hole injection layer 30, the hole transport layer 40, the light emitting layer 50, the electron transport layer 60, and the electrode layer 70 are sequentially stacked on the surface of the substrate 10. It has a configuration. Since the hole injection layer 30, the hole transport layer 40, the light emitting layer 50, and the electron transport layer 60 are all configured as an organic layer made of an organic material, the hole injection layer 30 is formed as the first organic layer 30, The hole transport layer 40 may be called the second organic layer 40, the light emitting layer 50 may be called the third organic layer 50, and the electron transport layer 60 may be called the fourth organic layer 60. Further, the ITO electrode 20 and the electrode layer 70 are arranged to face each other with a predetermined interval, and a hole injection layer 30, a hole transport layer 40, a light emitting layer 50, and an electron transport layer 60 are provided therebetween. It becomes the composition. That is, the organic EL element according to this embodiment has a configuration in which the first to fourth organic layers 30 to 60 are sandwiched between the pair of ITO electrodes 20 and the electrode layer 70.

  The substrate 10 is a transparent substrate that transmits light, and for example, a glass substrate or a plastic substrate may be used. If the board | substrate 10 is a transparent material, it can be comprised from various materials according to a use.

  The ITO electrode 20 is made of a transparent metal thin film that transmits light, and is configured as a transparent electrode. The ITO electrode 20 functions as an anode, and a positive voltage is applied during driving to inject holes. In the present embodiment, an example in which the ITO electrode 20 is used as an anode is given. However, other materials may be used as long as a transparent electrode can be formed.

  The substrate 10 and the ITO electrode 20 may be provided as an ITO substrate in a state where a thin film of the ITO electrode 20 is formed on the substrate 10 from the beginning.

  The hole injection layer 30 has a work function intermediate between the ITO electrode 20 and the hole transport layer 40, and is a buffer layer that bridges the holes injected into the ITO electrode 20 into the hole transport layer 40. . As described above, the hole injection layer 30 is made of an organic material. The hole injection layer 30 may be composed of various organic materials having a function of bridging the holes injected by the ITO electrode 20 to the hole transport layer 40. For example, the hole injection layer 30 is represented by the following general formula (5). The compound shown below (hereinafter referred to as “PEDOT: PSS”) may be used.

正孔輸送層４０は、正孔注入層３０から注入された正孔を発光層５０へと輸送する層である。正孔輸送層４０も、有機材料で構成される。正孔輸送層４０は、正孔を輸送する機能を有すれば、種々の有機材料を用いることができるが、例えば、下記の化学式（６）に示す化合物（以下、「α−ＮＰＤ」と呼ぶ。）を用いるようにしてもよい。

The hole transport layer 40 is a layer that transports holes injected from the hole injection layer 30 to the light emitting layer 50. The hole transport layer 40 is also made of an organic material. As the hole transport layer 40, various organic materials can be used as long as they have a function of transporting holes. For example, a compound represented by the following chemical formula (6) (hereinafter referred to as “α-NPD”). .) May be used.

また、例えば、正孔輸送層４０には、下記の化学式（７）に示す化合物（以下、「ＴＡＰＣ」と呼ぶ。）を用いるようにしてもよい。

Further, for example, a compound represented by the following chemical formula (7) (hereinafter referred to as “TAPC”) may be used for the hole transport layer 40.

電極層７０は、駆動時に陰極として機能し、負電圧が印加される。電極層７０は、金属薄膜で構成されてよく、例えば、アルミニウム、銀−マグネシウム合金、カルシウム等の金属薄膜として構成されてよい。

The electrode layer 70 functions as a cathode during driving, and a negative voltage is applied. The electrode layer 70 may be formed of a metal thin film, for example, a metal thin film of aluminum, silver-magnesium alloy, calcium, or the like.

  The electron transport layer 60 is a layer for transporting electrons injected from the electrode layer 70 to the light emitting layer 50. The electron transport layer 60 may be composed of an organic material. As the organic material, various organic materials can be used as long as they can function to transport electrons. For example, 2,2 ′, 2 ″-(1,3,5-benzenetriyl) -tris ( 1-phenyl-1-H-benzimidazole) (or 2, 2 ', 2 "-(1, 3, 5-benzenetriyl) -tris (1-phenyl-1-H-benzimidazole)) (hereinafter referred to as" TPBI May also be used. The chemical formula of TPBI is shown in the following chemical formula (8).

発光層５０は、電子と正孔の結合により発光する層である。発光層５０は、電子と正孔の結合により励起され、励起状態から基底状態に戻る際に光を発光する。発光層５０は、主成分となるホスト材料と、少量成分（副成分）となるゲスト材料とから構成される。本実施形態に係る有機発光素子の発光層５０は、ホスト材料にはベリリウムを含む金属錯体（ベリリウム錯体、Ｂｅ錯体）が用いられ、ゲスト材料には白金を含む燐光発光性材料（白金錯体、Ｐｔ錯体）が用いられる。ホスト材料とゲスト材料は、混合した状態で発光層５０中に存在し、主成分となるホスト材料中に、小量成分のゲスト材料が混合した状態で発光層５０は構成される。発光層５０において、発光の役割を担うのは、ゲスト材料である。よって、本実施形態に係る有機発光素子の発光層５０においては、Ｂｅ錯体が主成分となり、Ｐｔ錯体が少量成分となるが、発光の役割を担うのはＰｔ錯体ということになる。

The light emitting layer 50 is a layer that emits light by the combination of electrons and holes. The light emitting layer 50 is excited by the combination of electrons and holes, and emits light when returning from the excited state to the ground state. The light emitting layer 50 includes a host material that is a main component and a guest material that is a minor component (subcomponent). In the light emitting layer 50 of the organic light emitting device according to the present embodiment, a metal complex containing beryllium (beryllium complex, Be complex) is used as a host material, and a phosphorescent material containing platinum as a guest material (platinum complex, Pt). Complex). The host material and the guest material exist in the light emitting layer 50 in a mixed state, and the light emitting layer 50 is configured in a state where a small amount of guest material is mixed in the host material as the main component. In the light emitting layer 50, the guest material plays a role of light emission. Therefore, in the light emitting layer 50 of the organic light emitting device according to this embodiment, the Be complex is a main component and the Pt complex is a small amount component, but it is the Pt complex that plays a role of light emission.

  In addition, as a beryllium complex used for host material, Be complex represented by following General formula (1) is mentioned. The beryllium complex represented by the following general formula (1) is suitably used as a host material for a red light emitting platinum complex guest material, and can constitute the light emitting layer 50 that emits red light.

（式中、環Ｅ、環Ｆ及び環Ｇは、夫々独立して置換基を有していてもよい芳香環又は芳香族複素環を示す。ｎは０又は１を表す。）
より詳細には、赤色発光白金錯体ゲスト材料用のホスト材料に用いられるベリリウム錯体は、下記一般式（９）で表される。

(In the formula, ring E, ring F and ring G each independently represent an aromatic ring or an aromatic heterocyclic ring which may have a substituent. N represents 0 or 1.)
More specifically, the beryllium complex used for the host material for the red light emitting platinum complex guest material is represented by the following general formula (9).

ここで、一般式（９）において、置換基Ｒ^２ａ、Ｒ^２ｂ及びＲ^２ｃは、夫々独立して、アルキル基、ハロゲン化アルキル基、アラルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基、アミノ基、モノ又はジアルキルアミノ基、モノ又はジアリールアミノ基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルコキシカルボニル基、アシルオキシ基、アシルアミノ基、カルバモイル基、ヒドロキシル基、メルカプト基、ハロゲン原子、シアノ基、カルボキシル基、ニトロ基、ヘテロ環基、トリアルキルシリル基、トリアリールシリル基を表す。また、Ｒ^２ａ基同士、Ｒ^２ｂ基同士、Ｒ^２ｃ基同士、Ｒ^２ａとＲ^２ｂ、Ｒ^２ａとＲ^２ｃ、Ｒ^２ｃとＲ^２ｂが一緒になって縮合環構造を形成してもよい。ｍ^４及びｍ^６は０〜３の整数を表す。ｍ^５は０〜２の整数を表す。また、ｍ^４及びｍ^６が２以上の整数の場合は、複数のＲ^２ａ及びＲ^２ｃは異なっていてもよい。

Here, in the general formula (9), the substituents R ^2a , R ^2b and R ^2c are each independently an alkyl group, a halogenated alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group. Amino group, mono- or dialkylamino group, mono- or diarylamino group, alkoxy group, aryloxy group, heteroaryloxy group, alkoxycarbonyl group, acyloxy group, acylamino group, carbamoyl group, hydroxyl group, mercapto group, halogen atom, A cyano group, a carboxyl group, a nitro group, a heterocyclic group, a trialkylsilyl group, or a triarylsilyl group is represented. R ^2a groups, R ^2b groups, R ^2c groups, R ^2a and R ^2b , R ^2a and R ^2c , R ^2c and R ^2b may be combined to form a condensed ring structure. m ⁴ and ^{m 6} is an integer of 0 to 3. m ⁵ represents an integer of 0 to 2. When m ⁴ and m ⁶ are integers of 2 or more, the plurality of R ^2a and R ^2c may be different.

  Here, as an alkyl group, C1-C30, Preferably it is C1-C20, More preferably, a C1-C10 linear, branched or cyclic alkyl group is mentioned, for example. Specific examples include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, 2-ethylhexyl group, n-octyl group, and n-decyl group. , N-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group and the like.

  In addition, examples of the halogenated alkyl group include groups in which one or more hydrogen atoms of the above-described alkyl group are substituted with a halogen atom such as a fluorine atom or a chlorine atom. Specifically, for example, trifluoromethyl And perfluoroalkyl groups such as a pentafluoroethyl group.

  As the aralkyl group, one or more hydrogen atoms of an alkyl group may have a carbocyclic aryl group (the aryl group may have a substituent such as the above-described alkyl group, an alkoxy group described later, or a halogen atom). ). Preferable aralkyl groups include arylated alkyl groups having 7 to 30 carbon atoms, preferably 7 to 20 carbon atoms, more preferably 7 to 15 carbon atoms which may have a substituent. Specific examples include, for example, Examples include benzyl group, 4-methylbenzyl group, 4-methoxybenzyl group, 1-phenethyl group and the like.

  Examples of the alkenyl group include those having one or more double bonds in a linear or branched alkyl group having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Specific examples include a vinyl group, an aryl group, a 2-butenyl group, and a 3-pentenyl group.

  Examples of the alkynyl group include those having one or more triple bonds in a linear or branched alkyl group having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. It is done. Specific examples include ethynyl group, 1-propynyl group, 2-propynyl group and the like.

  Examples of the aryl group include aryl groups having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. Specific examples include a phenyl group, a tolyl group, a naphthyl group, and an anthranyl group. The aryl group may have a substituent such as the above-described alkyl group, an alkoxy group described later, and a halogen atom.

  The heteroaryl group has 2 to 15 carbon atoms and contains at least one hetero atom, preferably 1 to 3 hetero atoms such as nitrogen atom, oxygen atom, sulfur atom, etc. Preferably, a 5- or 6-membered monocyclic, polycyclic or fused-ring heteroaryl group is used. Specifically, furyl group, thienyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, pyrazolyl group, imidazolyl group, oxazolyl group, thiazolyl group, benzofuryl group, benzothienyl group, quinolyl group, isoquinolyl group, quinoxalinyl group Phthalazinyl group, quinazolinyl group, naphthyridinyl group, cinnolinyl group, benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, and the like. In addition, the heteroaryl group may have a substituent such as the above-described alkyl group, an alkoxy group described later, or a halogen atom.

  Examples of the mono- or dialkylamino group include amino groups in which one or two hydrogen atoms have been substituted with an alkyl group as described above. Specific examples include a methylamino group, a dimethylamino group, a diethylamino group, and the like.

  Examples of the mono- or diarylamino group include amino groups in which one or two hydrogen atoms are substituted with the aryl group as described above. Specific examples include a phenylamino group, a diphenylamino group, a ditolylamino group, and a phenylnaphthylamino group.

  Examples of the alkoxy group include groups in which an oxygen atom is bonded to the alkyl group as described above. Specific examples include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, tert-butoxy group, 2-ethylhexyloxy group and the like.

  Examples of the aryloxy group include groups in which an oxygen atom is bonded to the aryl group as described above. Specific examples include a phenoxy group, a tolyloxy group, and a naphthyloxy group.

  Examples of the heteroaryloxy group include groups in which an oxygen atom is bonded to the heteroaryl group as described above. Specific examples include 2-pyridyloxy group, 2-pyrazinyloxy group, 2-pyrimidinyloxy group, 2-quinolyloxy group and the like.

  The alkoxycarbonyl group may be linear, branched or cyclic, and examples thereof include an alkoxycarbonyl group having 2 to 19 carbon atoms. Specific examples include, for example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, 2-propoxycarbonyl group, n-butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, 2 -Ethylhexyloxycarbonyl group, lauryloxycarbonyl group, stearyloxycarbonyl group, cyclohexyloxycarbonyl group and the like can be mentioned.

  Examples of the acyloxy group include an acyloxy group derived from a carboxylic acid, for example, having 2 to 18 carbon atoms. Specific examples include an acetoxy group, a propionyloxy group, a butyryloxy group, a pivaloyloxy group, a pentanoyloxy group, a hexanoyloxy group, a lauroyloxy group, a stearoyloxy group, a benzoyloxy group, and an acryloyloxy group.

  Examples of the acylamino group include amino groups in which one hydrogen atom of the amino group is substituted with the acyl group as described above. Specific examples include formylamino group, acetylamino group, propionylamino group, pivaloylamino group, pentanoylamino group, hexanoylamino group, benzoylamino group and the like.

  Examples of the carbamoyl group include an unsubstituted carbamoyl group or a mono- or di-substituted carbamoyl group in which at least one hydrogen atom on a nitrogen atom is substituted with an alkyl group, an aryl group, an aralkyl group or the like as described above. Examples thereof include a carbamoyl group, a methylcarbamoyl group, a diethylcarbamoyl group, and a phenylcarbamoyl group.

  Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  The heterocyclic group is a heteroaryl group as described above, for example, imidazolyl group, pyridyl group, quinolyl group, furyl group, thienyl group, piperidyl group, morpholino group, benzoxazolyl group, benzimidazolyl group, benzthiazolyl group Etc.

  Examples of the trialkylsilyl group include a silyl group trisubstituted with an alkyl group as described above, and specific examples include a trimethylsilyl group and a tert-butyldimethylsilyl group.

  Examples of the triarylsilyl group include a silyl group trisubstituted with the above-mentioned aryl group, and specific examples include a triphenylsilyl group.

  Hereinafter, examples of specific structural formulas of the beryllium complexes represented by the general formulas (1) and (9) used for the host material for the red light emitting guest material of the light emitting layer 50 of the organic light emitting device according to this embodiment. Are shown as H-1 to H-25. However, the following structural formulas are merely representative examples, and the beryllium complexes represented by the general formulas (1) and (9) used in the present embodiment are not limited to these.

次に、緑色に発光する発光層５０のホスト材料に用いられるベリリウム錯体について説明する。緑色発光する発光層５０のホスト材料としては、下記一般式（２）で表されるＢｅ錯体が挙げられる。下記一般式（２）で表されるベリリウム錯体は、緑色発光白金錯体ゲスト材料用のホスト材料として好適に用いられ、緑色発光する発光層５０を構成することができる。

Next, the beryllium complex used for the host material of the light emitting layer 50 that emits green light will be described. Examples of the host material of the light emitting layer 50 that emits green light include a Be complex represented by the following general formula (2). The beryllium complex represented by the following general formula (2) is suitably used as a host material for a green light emitting platinum complex guest material, and can constitute the light emitting layer 50 that emits green light.

式中、環Ｈ及び環Ｊは、夫々独立して置換基を有していてもよい芳香環又は芳香族複素環を示す。ｎは０又は１を表す。

In the formula, each of the ring H and the ring J independently represents an aromatic ring or an aromatic heterocyclic ring which may have a substituent. n represents 0 or 1.

  More specifically, the beryllium complex used for the host material for the green light emitting platinum complex guest material is represented by the following general formula (10).

ここで、一般式（１０）において、置換基Ｒ^２ａ、Ｒ^２ｂは、夫々独立して、アルキル基、ハロゲン化アルキル基、アラルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基、アミノ基、モノ又はジアルキルアミノ基、モノ又はジアリールアミノ基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルコキシカルボニル基、アシルオキシ基、アシルアミノ基、カルバモイル基、ヒドロキシル基、メルカプト基、ハロゲン原子、シアノ基、カルボキシル基、ニトロ基、ヘテロ環基、トリアルキルシリル基、トリアリールシリル基を表し、Ｒ^２ａ基同士、Ｒ^２ｂ基同士、Ｒ^２ａとＲ^２ｂ、が一緒になって縮合環構造を形成してもよい。ｍ^５及びｍ^６は０〜４の整数を表す。また、ｍ^５及びｍ^６が２以上の整数の場合は、複数のＲ^２ａ及びＲ^２ｂは異なっていてもよい。

Here, in the general formula (10), each of the substituents R ^2a and R ^2b independently represents an alkyl group, a halogenated alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or an amino group. Mono- or dialkylamino group, mono- or diarylamino group, alkoxy group, aryloxy group, heteroaryloxy group, alkoxycarbonyl group, acyloxy group, acylamino group, carbamoyl group, hydroxyl group, mercapto group, halogen atom, cyano group, Represents a carboxyl group, a nitro group, a heterocyclic group, a trialkylsilyl group, a triarylsilyl group, and R ^2a groups, R ^2b groups, R ^2a and R ^2b together form a condensed ring structure Also good. m ⁵ and ^{m 6} is an integer of 0-4. Further, when m ⁵ and m ⁶ are integers of 2 or more, the plurality of R ^2a and R ^2b may be different.

  In addition, about description of each substituent, since it is the same as that of the description performed when showing General formula (9), the description is abbreviate | omitted.

  Hereinafter, examples of specific structural formulas of the beryllium complexes represented by the general formulas (2) and (10) used for the host material for the green light emitting guest material of the light emitting layer 50 of the organic light emitting device according to the present embodiment. Are shown as H-26 to H-50. However, the following structural formulas are merely representative examples, and the beryllium complexes represented by the general formulas (2) and (10) used in the present embodiment are not limited thereto.

次に、発光層５０のゲスト材料について説明する。ゲスト材料に用いられる燐光発光性白金錯体としては、下記一般式（３）で表される白金錯体が挙げられる。

Next, the guest material of the light emitting layer 50 will be described. Examples of the phosphorescent platinum complex used for the guest material include platinum complexes represented by the following general formula (3).

式（３）中、Ｗ^１、Ｗ^２、Ｗ^３及びＷ^４は、夫々白金原子に配位又は結合する部位を表す。Ｖ^１、Ｖ^２及びＶ^３は夫々二価の原子（団）、単結合又は二重結合を表す。破線で表される結合は単結合又は二重結合を、実線で表される結合は配位結合又は共有結合を表す。

In formula (3), W ¹ , W ² , W ³ and W ⁴ each represent a site that coordinates or bonds to a platinum atom. V ¹ , V ² and V ³ each represent a divalent atom (group), a single bond or a double bond. A bond represented by a broken line represents a single bond or a double bond, and a bond represented by a solid line represents a coordination bond or a covalent bond.

Here, in the general formula (2), W ¹ , W ² , W ³ and W ⁴ covalently bonded to the platinum atom by a carbon bond are not particularly limited, but an aromatic carbocyclic ligand (for example, a benzene ring, naphthalene) Ring), aromatic heterocyclic ligands (eg, pyridine ring, triazine ring, pyrrole ring, triazole ring, thiazole ring, thiadiazole ring, oxazole ring, oxadiazole ring, benzopyrrole ring, benzothiophene ring, benzofuran Ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, phthalazine ring, quinazoline ring, naphthyridine ring, cinnoline ring, pyrazole ring, pyrrole ring and the like. These ring ligands may be substituted with the above-described alkyl group, alkoxy group, halogenated alkyl group, aryl group, heteroaryl group, substituted amino group or the like.

W ¹ , W ² , W ³ and W ⁴ coordinated or bonded to the platinum atom with a nitrogen atom are not particularly limited, but include a pyridine ring, a triazine ring, a pyrrole ring, a triazole ring, a thiazole ring, a thiadiazole ring, an oxazole ring, an oxazole ring, Diazole ring, benzopyrrole ring, benzothiophene ring, benzofuran ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, phthalazine ring, quinazoline ring, naphthyridine ring, cinnoline ring, pyrazole ring, pyrrole ring And nitrogen-containing heterocycles such as Imino group (—C (R) ═N—) and the like. The nitrogen-containing heterocycle may be substituted with the above-mentioned alkyl group, alkoxy group, halogenated alkyl group, aryl group, heteroaryl group, substituted amino group, or the like.

W ¹ , W ² , W ³ and W ⁴ bonded to the platinum atom with an oxygen atom are aryloxy (preferably having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms). , For example, phenyloxy, tolyloxy, naphthyloxy, anthryloxy group, etc., heteroaryloxy (2-20 carbon atoms, preferably 3-15 carbon atoms, more preferably 3-10 carbon atoms, for example pyridyloxy , Triazolyloxy, thiazolyloxy, thiadiazolyloxy, oxazolyloxy, oxadiazolyloxy, indolyloxy, benzothienyloxy, benzofuryloxy, pyrimidinyloxy, pyrazinyloxy, pyridazinyloxy, quinolyloxy, isoquino Ryloxy, quinoxalinyloxy, phthalazinyloxy, Zoriniruokishi, naphthyridone Gini oxy, thin glue oxy, pyrazolyloxy, pyrrolyloxy, etc.). These aryloxy and heteroaryloxy may be substituted with the above-mentioned alkyl group, alkoxy group, halogenated alkyl group, aryl group, heteroaryl group, substituted amino group or the like.

W ¹ , W ² , W ³ and W ⁴ bonded to the platinum atom with a sulfur atom are arylthio (preferably having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, For example, phenylthio, tolylthio, naphthylthio, anthrylthio group, etc., heteroarylthio (2-20 carbon atoms, preferably 3-15 carbon atoms, more preferably 3-10 carbon atoms, for example, pyridylthio, triazolylthio, thiazolylthio, Asiazolylthio, oxazolylthio, oxadiazolylthio, indolylthio, benzothienylthio, benzofurylthio, pyrimidinylthio, pyrazinylthio, pyridazinylthio, quinolylthio, isoquinolylthio, quinoxalinylthio, phthalazinylthio, quinazolinylthio, naphthyridinylthio, cinnori Lucio, pyrazolyl thio, Piroriruchio etc.). These arylthio and heteroarylthio may be substituted with an alkyl group, an alkoxy group, a halogenated alkyl group, an aryl group, a heteroaryl group, a substituted amino group or the like which will be described later.
V ¹ , V ² and V ³ each represent a linking group, a single bond or a double bond. The linking group is not particularly limited, and examples thereof include a nitrogen atom linking group, an oxygen atom linking group, a carbonyl linking group, a (poly) methylene group, an arylene group, a heteroarylene group, and a silicon atom linking group.

  Moreover, as a preferable phosphorescent platinum complex used as the guest material, a platinum complex represented by the following general formula (4) can be given.

式（４）中、環Ａ、環Ｂ、環Ｃ及び環Ｄは、この中の何れか２つの環が置換基を有していてもよい含窒素複素環を示し、残りの２つの環が置換基を有していてもよい芳香環又は芳香族複素環を示す。環Ａ、環Ｂ、環Ｃ、環Ｄは夫々が置換基を介して縮合して環を形成してもよい。環Ａ、環Ｂ、環Ｃ、環Ｄは該環において複数の置換基同士が縮合してさらに環を形成してもよい。Ｘ^１、Ｘ^２、Ｘ^３及びＸ^４は、この中の何れか２つが白金原子に配位結合する窒素原子を示し、残りの２つは炭素原子又は窒素原子を表す。Ｙ^１、Ｙ^２、Ｙ^３、Ｙ^４、Ｙ^５及びＹ^６は夫々独立して炭素又は窒素原子を示す。Ｑ^１、Ｑ^２及びＱ^３は、夫々独立して二価の原子（団）又は結合手を示す。Ｑ^１と環Ａ及び環Ｂ、Ｑ^２と環Ａ及び環Ｃ、Ｑ^３と環Ｂ及び環Ｄは夫々が置換基を介して縮合して環を形成してもよい。Ｚ^１、Ｚ^２、Ｚ^３及びＺ^４は、いずれか２つが配位結合手を示し、残りの２つが共有結合手、酸素原子又は硫黄原子を示す。

In formula (4), ring A, ring B, ring C and ring D represent a nitrogen-containing heterocycle in which any two of the rings may have a substituent, and the remaining two rings are An aromatic ring or an aromatic heterocyclic ring which may have a substituent is shown. Ring A, ring B, ring C, and ring D may each be condensed via a substituent to form a ring. Ring A, ring B, ring C, and ring D may be further formed by condensing a plurality of substituents in the ring. X ¹ , X ² , X ³ and X ⁴ each represent a nitrogen atom in which any two of them coordinate to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom. Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ and Y ⁶ each independently represent a carbon or nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (group) or a bond. Q ¹ and ring A and ring B, Q ² and ring A and ring C, Q ³ and ring B and ring D may be condensed via a substituent to form a ring. Any one of Z ¹ , Z ² , Z ³ and Z ⁴ represents a coordination bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

  In the platinum complex represented by the general formula (4) of the present embodiment, the nitrogen-containing heterocycle optionally having a substituent in ring A, ring B, ring C, or ring D is at least one nitrogen. It is a heterocycle having an atom as a heteroatom, and may further contain 1 to 3 hetero atoms consisting of, for example, a nitrogen atom, an oxygen atom or a sulfur atom, preferably 5 or 6 members. Monocyclic, polycyclic, or condensed heterocyclic rings may be mentioned. The nitrogen atom of the nitrogen-containing heterocyclic ring can be coordinated to a platinum atom. Examples of the other ring forming the polycyclic group or the condensed cyclic group include the above-described heterocyclic group and carbocyclic group. Preferred nitrogen-containing heterocycles include, for example, pyridine ring, triazine ring, pyrrole ring, diazole ring, triazole ring, thiazole ring, thiadiazole ring, oxazole ring, oxadiazole ring, benzopyrrole ring, pyrimidine ring, pyrazine ring, pyridazine. Ring, quinoline ring, isoquinoline ring, quinoxaline ring, phthalazine ring, quinazoline ring, naphthyridine ring, cinnoline ring, pyrazole ring, 2H-pyrrole ring and the like.

One or more hydrogen atoms on the nitrogen-containing heterocycle in the ring A, ring B, ring C, and ring D of the platinum complex represented by the general formula (4) may be substituted with a substituent. Such a substituent is not particularly limited as long as it does not adversely affect the light emission characteristics, but preferably R ^1a , R ^1b , R ^1c and a platinum complex represented by the following general formula (8) Mention may be made of the groups described for R ^1d .

  In the platinum complex represented by the general formula (4) of the present embodiment, the aryl in the case where the ring A, ring B, ring C, and ring D are an aryl ring or a heteroaryl ring which may have a substituent. Examples of the ring include monocyclic, polycyclic or condensed cyclic carbocyclic groups having 6 to 40 carbon atoms, preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. The heteroaryl ring is a monocyclic or polycyclic 5- to 8-membered, preferably 5- or 6-membered, containing 1 to 3 hetero atoms including, for example, a nitrogen atom, an oxygen atom or a sulfur atom. And a heterocyclic group of formula or condensed cyclic. Examples of the other ring forming the polycyclic or condensed ring of the heterocyclic group include the above-described heterocyclic group and carbocyclic group.

  Preferred aryl rings or heteroaryl rings include, for example, benzene ring, pyridine ring, triazine ring, pyrrole ring, diazole ring, furan ring, thiophene ring, naphthalene ring, pyrimidine ring, pyridazine ring, quinoline ring, quinoxaline ring, quinazoline ring. Cinnoline ring, pyrazole ring, benzofuran ring, benzothiophene ring and the like.

One or more hydrogen atoms on the aryl ring or heteroaryl ring in the ring A, ring B, ring C, and ring D of the platinum complex represented by the general formula (4) may be substituted with a substituent. Such a substituent is not particularly limited as long as it does not adversely affect the light emission characteristics, but preferably R ^1a , R ^1b , R ^1c and a platinum complex represented by the following general formula (11) Mention may be made of the groups described for R ^1d .

Next, the divalent atom (group) represented by Q ¹ , Q ² , and Q ³ in the general formula (4) will be described.

In the present embodiment, divalent atoms (groups) represented by Q ¹ , Q ² , and Q ³ exist as spacers that connect four ring groups. Specific examples _{^{include, - (CR 1 R 2)}} n12 -, - O (CR 1 R 2) n12 O -, - (O) n13 C (= O) (O) n14 -, oxygen atom, sulfur atom ^{, -NR 3 -, - BR 4} -, - S (= O) -, - SO 2 -, - O (SO 2) O -, - Si (R 5 R 6) -, - OSi (R 5 R 6 ) O -, - C (= CR 7 R 8) - , and the like. n12 represents an integer of 1 to 3, and n13 and n14 each represents 0 or 1.

_{^{- (CR 1 R 2) n12}} - The and _{^{-O (CR 1 R 2) n12}} R 1 and ^{R 2} in O-, are independently a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, NR R ³ in ³ includes a hydrogen atom, an alkyl group, an aralkyl group, or an aryl group. R ⁴ in BR ⁴ includes an alkyl group, an aralkyl group, and an aryl group, and SiR ⁵ R ⁶ and —O ( R ⁵ and R ⁶ in SiR ⁵ R ⁶ ) O— each independently include an alkyl group, an aralkyl group, or an aryl group, and R ⁷ and R ⁸ in —C (═CR ⁷ R ⁸ ) — It represents a hydrogen atom, an alkyl group, an aralkyl group, and an aryl group, or a cyano group, these ^{R 1, R 2, R 3} , R 4, R 5, R 6, R 7 and ^{R 8} Alkyl represented, specific examples and the like of the aralkyl group and aryl group are the same as that in the alkyl group, aralkyl group and aryl group in the platinum complex represented by the general formula (8) described later. In addition, the ring formed together with the atoms in which R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ are bonded to each other and each is substituted is a 5- or 6-membered ring that may contain a hetero atom A ring is mentioned.

  Specific examples of the ring include a cyclopentane ring, a cyclohexane ring, a tetrahydrofuran ring, a tetrahydropyran ring, a dioxolane ring, a dioxane ring, a furan ring, a pyran ring, a thiophene ring, a benzene ring, a tetrahydrosilole ring, and a silole ring. These rings also include a divalent spiro ring from the same atom, a divalent saturated ring from a different atom, an aromatic ring, and the like.

  Furthermore, as a preferable phosphorescent material used for the guest material of the light emitting layer 50 of the organic light emitting device according to this embodiment, a platinum complex represented by the following general formula (11) can be given.

式（１１）中、置換基Ｒ^１ａ、Ｒ^１ｂ、Ｒ^１ｃ及びＲ^１ｄは、夫々独立して、アルキル基、ハロゲン化アルキル基、アラルキル基、アルケニル基、アルキニル基、アリール基、ヘテロアリール基、アミノ基、モノ又はジアルキルアミノ基、モノ又はジアリールアミノ基、アルコキシ基、アリールオキシ基、ヘテロアリールオキシ基、アルコキシカルボニル基、アシルオキシ基、アシルアミノ基、カルバモイル基、ヒドロキシル基、メルカプト基、ハロゲン原子、シアノ基、カルボキシル基、ニトロ基、ヘテロ環基、トリアルキルシリル基、トリアリールシリル基を表し、Ｒ^１ａ基同士、Ｒ^１ｂ基同士、Ｒ^１ｃ基同士、Ｒ^１ｄ基同士、Ｒ^１ａとＲ^１ｂ、Ｒ^１ａとＲ^１ｃ、Ｒ^１ｂとＲ^１ｄとが一緒になって縮合環構造を形成してもよい。又は夫々の基とＱ^１、Ｑ^２、Ｑ^３におけるＲ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、又はＲ^６とで縮合環を形成してもよい。ｍ^１、ｍ^２、ｍ^３及びｍ^４は０〜３の整数を表す。また、ｍ^１、ｍ^２、ｍ^３及びｍ^４が２以上の整数の場合は、複数のＲ^１ａ、Ｒ^１ｂ、Ｒ^１ｃ及びＲ^１ｄは異なっていてもよい。Ｘ^１、Ｘ^２、Ｘ^３、Ｘ^４、Ｑ^１、Ｑ^２、Ｑ^３、Ｚ^１、Ｚ^２、Ｚ^３及びＺ^４は上記と同じ意味を表す。

In the formula (11), the substituents R ^1a , R ^1b , R ^1c and R ^1d are each independently an alkyl group, a halogenated alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, Amino group, mono- or dialkylamino group, mono- or diarylamino group, alkoxy group, aryloxy group, heteroaryloxy group, alkoxycarbonyl group, acyloxy group, acylamino group, carbamoyl group, hydroxyl group, mercapto group, halogen atom, cyano Group, carboxyl group, nitro group, heterocyclic group, trialkylsilyl group, triarylsilyl group, R ^1a groups, R ^1b groups, R ^1c groups, R ^1d groups, R ^1a and R ^1b , R ^1a and ^{R 1c,} even when the ^{R 1b} and ^{R 1d} to form a fused ring structure together . Alternatively, each group and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , or R ^{6 in} Q ¹ , Q ² , and Q ³ may form a condensed ring. m ^{1, m} 2, ^{m 3} and ^{m 4} represents an integer of 0 to 3. When m ¹ , m ² , m ³ and m ⁴ are integers of 2 or more, the plurality of R ^1a , R ^1b , R ^1c and R ^1d may be different. X ¹ , X ² , X ³ , X ⁴ , Q ¹ , Q ² , Q ³ , Z ¹ , Z ² , Z ³ and Z ⁴ represent the same meaning as described above.

In the general formula (11), examples of the alkyl group represented by R ^1a , R ^1b , R ^1c , and R ^1d include, for example, 1 to 30 carbon atoms as described above, preferably 1 to 20 carbon atoms, more preferably carbon atoms. Examples thereof include linear, branched or cyclic alkyl groups of 1 to 10. Specific examples include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, n-hexyl group, 2-ethylhexyl group, n-octyl group, and n-decyl group. , N-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group and the like.

  Similarly, in the general formula (11), a halogenated alkyl group, aralkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, amino group, mono- or dialkylamino group, mono- or diarylamino group, alkoxy group, aryl The oxy group, heteroaryloxy group, alkoxycarbonyl group, acyloxy group, acylamino group, carbamoyl group, halogen atom, heterocyclic group, trialkylsilyl group, and triarylsilyl group are as described in the general formula (1). The same thing is mentioned.

These substituents may be further substituted. Further, R ^1a groups, R ^1b groups, R ^1c groups, and R ^1d groups may be combined to form a condensed ring structure. Furthermore, R ^1a and R ^1b , R ^1c and R ^1c Or / and R ^1b and R ^1d may be combined to form a condensed ring structure. Specific examples of the condensed ring include a phenanthrene ring, a fluoren-9-one ring, a 1,10-phenanthroline ring, and a 4,5-diazafluoren-9-one ring. m ¹ , m ² , m ³ and m ⁴ represent the numbers of R ^1a , R ^1b , R ^1c and R ^1d , respectively, and independently represent an integer of 0 to 3; When m ¹ , m ² , m ³ and m ⁴ are integers of 2 or more, a plurality of R ^1a , R ^1b , R ^1c and R ^1d may be the same or different from each other.

  As a more preferable form of the platinum complex represented by the general formula (11), for example, a platinum complex represented by the following general formula (12) may be mentioned.

式（１２）中、Ｒ^１ａ、Ｒ^１ｂ、Ｒ^１ｃ及びＲ^１ｄは、夫々独立して、アルキル基、ハロゲン化アルキル基、アラルキル基、アルケニル基、アルキニル基、アリール基、アミノ基、モノ又はジアルキルアミノ基、モノ又はジアラルキルアミノ基、モノ又はジアリールアミノ基、アルコキシ基、アリールオキシ基、アラルキルオキシ基、アリールオキシ基、ヘテロアリールオキシ基、アシル基、アルコキシカルボニル基、アシルオキシ基、アシルアミノ基、カルバモイル基、ヒドロキシル基、メルカプト基、ハロゲン原子、シアノ基、カルボキシル基、ニトロ基、ヘテロ環基、トリアルキルシリル基、トリアリールシリル基、を表し、Ｒ^１ａ基同士、Ｒ^１ｂ基同士、Ｒ^１ｃ基同士、Ｒ^１ｄ基同士、Ｒ^１ａとＲ^１ｂ、Ｒ^１ａとＲ^１ｃ、Ｒ^１ｂとＲ^１ｄとが一緒になって縮合環構造を形成してもよい。又はＲ^１ａとＲ^１ｂはＲ^１ａｂと一緒になって縮合環構造を形成してもよい。Ｒ^１ａｂは水素原子、アルキル基、アラルキル基、アリール基、ヘテロ環基を表す。白金原子とＸ^１、Ｘ^２、Ｘ^３及びＸ^４との結合は、そのうちの二つが配位結合を残りの二つが共有結合を表す。Ｘ^１、Ｘ^２、Ｘ^３、Ｘ^４、ｍ^１、ｍ^２、ｍ^３及びｍ^４は上記と同じ意味を表す。

In the formula (12), R ^1a , R ^1b , R ^1c and R ^1d each independently represents an alkyl group, a halogenated alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, a mono group or a dialkyl group. Amino group, mono- or diaralkylamino group, mono- or diarylamino group, alkoxy group, aryloxy group, aralkyloxy group, aryloxy group, heteroaryloxy group, acyl group, alkoxycarbonyl group, acyloxy group, acylamino group, carbamoyl Group, hydroxyl group, mercapto group, halogen atom, cyano group, carboxyl group, nitro group, heterocyclic group, trialkylsilyl group, triarylsilyl group, R ^1a groups, R ^1b groups, R ^1c group R ^1d groups, R ^1a and R ^1b , R ^1a and R ^1c , R ^1b and R ^1d may be combined to form a condensed ring structure. Alternatively, R ^1a and R ^1b may ^combine with R ^1ab to form a condensed ring structure. R ^1ab represents a hydrogen atom, an alkyl group, an aralkyl group, an aryl group, or a heterocyclic group. Of the bonds between the platinum atom and X ¹ , X ² , X ³ and X ⁴ , two of them represent a coordination bond and the remaining two represent a covalent bond. X ¹ , X ² , X ³ , X ⁴ , m ¹ , m ² , m ³ and m ⁴ represent the same meaning as described above.

The explanation of the substituents R ^1a , R ^1b , R ^1c , R ^1d and R ^{1ab in} the general formula (12) is the same as that listed as the explanation of the substituents in the general formula (11).

Further, R ^1a groups, R ^1b groups, R ^1c groups, and R ^1d groups may be combined to form a condensed ring structure. Furthermore, R ^1a and R ^1b , R ^1a and R ^1c Or / and R ^1b and R ^1d may be combined to form a condensed ring structure. Alternatively, R ^1a and R ^1b may be combined with R ^1ab to form a condensed ring structure. Specific examples of the condensed ring include a phenanthrene ring, a fluoren-9-one ring, a 1,10-phenanthroline ring, and a 4,5-diazafluoren-9-one ring.

  Hereinafter, specific structural formulas of platinum metal complexes that are used in the organic light-emitting device according to the present embodiment and emit phosphorescent light that is the guest material represented by the general formula (3) are denoted by G-1 to G-67. It is shown below. However, these are merely representative examples, and the platinum metal complex represented by the general formula (3) used in the present invention is not limited thereto.

また、本実施形態に係る有機発光素子の発光層５０のゲスト材料として用いられる一般式（３）で示される燐光発光子白金錯体の他の具体的な化合物群を以下に示す。

Further, other specific compound groups of the phosphorescent platinum complex represented by the general formula (3) used as the guest material of the light emitting layer 50 of the organic light emitting device according to this embodiment are shown below.

［実施例］

[Example]

  Next, organic light emitting devices according to examples of the present invention will be described. In the organic light emitting device according to this example, the organic light emitting device as shown in FIG. 1 was produced by changing various combinations of the host material and guest material of the light emitting layer 50. And the characteristic of the obtained organic light emitting element was measured and evaluated with the comparative example.

First, parts common to the first to fifth embodiments will be described. The organic light-emitting elements according to Examples 1 to 5 have the element configuration shown in FIG. 1, and an element having four organic layers was manufactured as shown in FIG. As a manufacturing method, first, PEDOT: TSS represented by the general formula (4) is formed as a hole injection layer 30 on an ITO substrate in which a thin film of ITO 20 is formed on a glass substrate 10 by spin coating. did. Thereafter, the hole transport layer 40, the light emitting layer 50, the electron transport layer 60, and the electrode layer 70 were vacuum-deposited by resistance heating in a vacuum chamber of 10 ⁻⁴ Pa, and continuously formed. As the organic material, the hole transport layer 40 is α-NPD represented by the general formula (5), the light emitting layer 50 is a predetermined organic material used according to each of the examples and comparative examples, and the electron transport layer 60 is As a specific example of TPBI represented by the general formula (6) or the general formula (1), a beryllium complex represented by H-1 was used. Further, LiF / Al was used for the electrode layer 70. The entire material structure including the film thickness is as follows.

Organic layer 1 (hole injection layer) (35 nm): PEDOT: PSS or ND-1506 (manufactured by Nissan Chemical Co., Ltd.)
Organic layer 2 (hole transport layer) (40 nm): α-NPD
Organic layer 3 (light emitting layer) (35 nm): predetermined host / predetermined guest Organic layer 4 (electron transport layer) (40 or 20 nm): TPBI or H-1
Electrode layer (0.5 nm / 100 nm): LiF / Al
A voltage was applied with the ITO 20 side of the obtained organic light-emitting device as an anode and the Al electrode layer 70 side as a cathode, and current, luminance, and emission spectrum were measured. In the measurement, oxygen and water become a cause of element deterioration, so in order to remove such a factor, take out from the vacuum chamber without contacting the line box with air and perform measurement after sealing with a glass cap. went.

  [Example 1]

In order to confirm the superiority of the beryllium complex over the zinc complex and other host materials, the guest material is a phosphorescent platinum complex compound indicated by G-4, and the host material is H shown as a beryllium complex. -1, Zn (BTP) ₂ which is a zinc complex, and BAlq and CBP which are general host materials were used, respectively. In each host material, 3% by weight of the guest material was doped by co-evaporation to form the light emitting layer 50. In addition, Zn (BTP) ₂ of the zinc complex is represented by the following general formula (13). As described above, PEDOT: PSS was used for the hole injection layer 30, H-1 was used for the electron transport layer 60, and the thickness was 20 nm.

表１は、実施例１及び比較例１〜３に係る有機発光素子の測定結果を示す。表１において、各種のホスト材料に対し、外部量子効率（％）、駆動電圧（Ｖ）、色度（１００ｃｄ／ｍ^２）の項目の測定結果が示されている。外部量子効率は、発光効率を示し、数値が高い程効率が高い。一方、駆動電圧は、低いほど低電圧駆動が可能となるので、値は低い方がよい。色度は、色を示した指標であり、大きく外れた値をとっていなければ問題無い。

Table 1 shows the measurement results of the organic light emitting devices according to Example 1 and Comparative Examples 1 to 3. In Table 1, the measurement results of the items of external quantum efficiency (%), drive voltage (V), and chromaticity (100 cd / m ² ) are shown for various host materials. The external quantum efficiency indicates the luminous efficiency, and the higher the numerical value, the higher the efficiency. On the other hand, the lower the drive voltage is, the lower the voltage is possible, so the lower the value, the better. The chromaticity is an index indicating the color, and there is no problem as long as the value is not greatly deviated.

表１に示すように、比較例３に係る特許文献１に記載された亜鉛錯体のホスト材料と白金錯体のゲスト材料の組み合わせは、比較例１、２に係る一般的なホスト材料と白金錯体のゲスト材料の組み合わせよりも。外部量子効率が高くなっており、高い発光効率を示している。そして、実施例１に係るベリリウム錯体のホスト材料と白金錯体のゲスト材料の組み合わせは、更に比較例３よりも高い外部量子効率を示している。このことから、ベリリウム錯体のホスト材料と白金錯体のゲスト材料の組み合わせは、亜鉛錯体のホスト材料と白金錯体のゲスト材料の組み合わせよりも発光効率が高いことが分かる。

As shown in Table 1, the combination of the host material of the zinc complex and the guest material of the platinum complex described in Patent Document 1 according to Comparative Example 3 is the same as that of the general host material and the platinum complex according to Comparative Examples 1 and 2. Than a combination of guest materials. External quantum efficiency is high, indicating high luminous efficiency. The combination of the beryllium complex host material and the platinum complex guest material according to Example 1 further exhibits higher external quantum efficiency than Comparative Example 3. This indicates that the combination of the beryllium complex host material and the platinum complex guest material has higher luminous efficiency than the combination of the zinc complex host material and the platinum complex guest material.

FIG. 2 is a graph showing luminance attenuation characteristics of the organic light emitting device according to Example 1 and the organic light emitting device according to Comparative Example 3. In FIG. 2, the horizontal axis represents elapsed time (hr), and the vertical axis represents luminance (cd / m ² ). Since it is a characteristic showing luminance attenuation from 1000 cd / m ² , it means that the longer the state where attenuation is less, the longer the life is. As shown in FIG. 2, the organic light emitting device using the H-1 host material (Be complex) according to Example 1 is the organic light emitting device using the Zn (BTP) ₂ host material according to Comparative Example 3. It can be seen that there is less attenuation than that and a long life.

  As described above, according to the organic light emitting device according to Example 1 using the beryllium complex as the host material, not only the organic light emitting devices according to Comparative Examples 1 and 2 using a general host material but also a zinc complex as the host material. It is possible to provide an organic light emitting device having higher luminous efficiency and longer life than the organic light emitting device according to Comparative Example 3 described above.

  [Example 2]

In Example 2, in order to show the advantage that the guest material is a platinum complex in combination with the host material of the beryllium complex, an element structure other than the guest material was fixed to produce an organic light emitting element. As a guest material of the light emitting layer 50, Ir (piq) ₃ which is a typical red iridium complex is used as a comparative example, and platinum complexes G-4, G-5 and G-7 are shown as examples. What was being used was used. Ir (piq) ₃ is represented by the following general formula (14).

赤色Ｉｒ錯体をゲスト材料とした有機発光素子を比較例４とし、白金錯体Ｇ−４をゲスト材料とした有機発光素子を実施例２Ａ、白金錯体Ｇ−５をゲスト材料とした有機発光素子を実施例２Ｂ、白金錯体Ｇ−７をゲスト材料とした有機発光素子を実施例２Ｃとする。また、発光層５０のホスト材料には、ベリリウム錯体であるＨ−１を共通に用い、ゲスト濃度は３重量％、正孔注入層３０にはＰＥＤＯＴ：ＰＳＳを用い、電子輸送層にはＨ−１（膜厚２０ｎｍ）を用いた。

An organic light-emitting device using a red Ir complex as a guest material is set as Comparative Example 4, an organic light-emitting device using a platinum complex G-4 as a guest material is Example 2A, and an organic light-emitting device using a platinum complex G-5 as a guest material is executed. Example 2B An organic light emitting device using platinum complex G-7 as a guest material is referred to as Example 2C. Further, H-1 which is a beryllium complex is commonly used as the host material of the light emitting layer 50, the guest concentration is 3% by weight, PEDOT: PSS is used for the hole injection layer 30, and H- is used for the electron transport layer. 1 (film thickness 20 nm) was used.

  Table 2 shows the measurement results of the organic light emitting devices according to Examples 2A to 2C and Comparative Example 4. The measurement items are the same as in Table 1.

表２において、実施例２Ａ乃至２Ｃに係る有機発光素子は、いずれも比較例４に係る有機発光素子よりも高い外部量子効率を示している。よって、ホスト材料をベリリウム錯体とした場合において、ゲスト材料は白金錯体とする組み合わせが、燐光発光性材料として一般的なイリジウム錯体のゲスト材料との組み合わせより高い発光効率が得られることが分かる。

In Table 2, the organic light emitting devices according to Examples 2A to 2C all have higher external quantum efficiencies than the organic light emitting device according to Comparative Example 4. Therefore, it can be seen that when the host material is a beryllium complex, a combination of a guest material and a platinum complex can achieve higher luminous efficiency than a combination of a guest material of a general iridium complex as a phosphorescent material.

  [Example 3]

In Example 3, the combination of the beryllium complex with the host material was evaluated for the device lifetime when the guest material was a platinum complex and when it was an iridium complex. Therefore, the organic light emitting device according to Example 3 using G-4 which is a platinum complex as a guest material and the comparative example 5 using Ir (piq) ₃ which is a typical phosphorescent material as a guest An organic light emitting device was produced. Further, beryllium complex H-1 was used as a host material, the guest concentration was 6 wt%, PEDOT: PSS was used for the hole transport layer 30, and the electron transport layer 60 was TPBI (film thickness 40 nm). The state of luminance attenuation from 1000 cd / m ² during low voltage driving was measured.

FIG. 3 is a diagram showing the measurement results of Example 3. In FIG. 3, the organic light emitting device according to Example 3 using G-1 which is a platinum complex as a guest material is the organic light emitting device according to Comparative Example 5 using Ir (piq) ₃ which is an iridium complex as a guest material. It has been shown to be less damped and have a longer life.

Thus, as shown in FIG. 3, the result was obtained that the device using G-4 as the guest material had a longer lifetime than the device using Ir (piq) ₃ as the guest material.

  [Example 4]

  In Example 4, it is shown that the element configuration of the light emitting layer 50 using beryllium complex as the host material and platinum complex as the guest material is effective for the light emitting layer configurations of various guest ratios. In Example 4, the structure of the light emitting layer was such that H-1 was used as a host material, G-4 was used as a guest material, and the concentration of the guest material was 1% by weight, 6% by weight, and 10% by weight. And it comprised as an organic light emitting element which concerns on Example 4A, 4B, 4C, respectively. At that time, PEDOT: PSS was used for the hole injection layer 30 and the electron transport layer 60 was TPBI (film thickness 40 nm).

  Table 3 shows the measurement results of the organic light emitting devices according to Examples 4A to 4C.

表３に示されるように、ゲスト濃度を上げると駆動電圧の上昇がみられるものの、いずれの素子においても高い発光効率が得られた。このように、実施例４Ａ乃至４Ｃに係る有機発光素子は、ゲスト濃度を変化させても優れた発光効率を得ることができ、種々のゲスト濃度とすることが可能であることが分かる。

As shown in Table 3, although the drive voltage was increased when the guest concentration was increased, high luminous efficiency was obtained in any of the elements. Thus, it can be seen that the organic light emitting devices according to Examples 4A to 4C can obtain excellent light emission efficiency even when the guest concentration is changed, and can have various guest concentrations.

  [Example 5]

  In Example 5, in an organic light emitting device having a light emitting layer 50 using a beryllium complex as a host material and a platinum complex as a guest material, even when another component is further added to the host material, high luminous efficiency and long life are obtained. Show what can be done. In Example 5, in particular, the case where the light emitting layer is composed of three or more kinds of materials including a Be complex and a Pt complex will be verified. In recent years, it has been reported that a high-efficiency and long-life device can be obtained by configuring a light-emitting layer with three components (two types of host + guest) (for example, see Non-Patent Documents 1 and 2).

In the organic light-emitting device according to Example 5, the configuration of the light-emitting layer 50 includes platinum complex G-4 as a guest material, beryllium complex H-1 as two types of host materials, and iridium as a green light-emitting material. The complex Ir (ppy) ₂ acac was used. Ir (ppy) ₂ acac is represented by the following general formula (15).

なお、各成分の構成比は、Ｈ−１：Ｉｒ（ｐｐｙ）_２ａｃａｃ：Ｇ−４＝７７：２０：３とした。比較例６に係る有機発光素子として、発光層がＨ−１：Ｇ−４＝９７：３の構成比の素子も作製した。正孔注入層３０にはＮＤ１５０６を用い、電子輸送層６０にはＴＰＢＩ（膜厚４０ｎｍ）を用いた。

The component ratio of each component was H-1: Ir (ppy) ₂ acac: G-4 = 77: 20: 3. As an organic light emitting device according to Comparative Example 6, a device having a light emitting layer with a composition ratio of H-1: G-4 = 97: 3 was also produced. ND1506 was used for the hole injection layer 30, and TPBI (film thickness 40 nm) was used for the electron transport layer 60.

  Table 4 shows the measurement results of the organic light emitting devices according to Example 5 and Comparative Example 6.

表４より、ベリリウム錯体を単体のホスト材料とした場合以上の特性は得られなかったものの、同程度の特性を得ることができた。したがって、発光層がベリリウム錯体と白金錯体を含む３種類以上の材料から構成される場合についても、本発明が適用可能であることがわかった。これにより、例えば、ホスト材料にベリリウム錯体よりも安価な材料を合わせて用いることにより、有機発光素子のコストを低減させることが可能となる。

From Table 4, although the above characteristics were not obtained when the beryllium complex was used as a single host material, similar characteristics could be obtained. Therefore, it has been found that the present invention can also be applied to a case where the light emitting layer is composed of three or more kinds of materials including a beryllium complex and a platinum complex. Thereby, for example, it is possible to reduce the cost of the organic light emitting device by using a host material that is less expensive than the beryllium complex.

  Here, the materials other than the Be complex and the Pt complex constituting the light emitting layer may be a charge transport material as in the case of α-NPD described in Non-Patent Document 1, and Non-Patent Document 2 and the present example. Similarly, a light emitting material such as an iridium complex may be used.

  In Examples 1 to 5, a guest material that emits red light is selected, a light emitting layer 50 that emits red light is formed, an organic light emitting element is configured, and the results of the implementation are measured.

[Example 6]
In Example 6, an example in which an organic light-emitting element is implemented by forming a light-emitting layer 50 that emits green light using a platinum complex guest material that emits green light and a beryllium complex that is used in a platinum complex guest material that emits green light will be described. .

  First, the common part of the element manufacturing process used in Example 6 and Comparative Example 7 will be described. The element shown in FIG. 1 was used as the element configuration. PEDOT: PSS as the hole injection layer 30 is formed on the ITO substrate 20 by spin coating, and then the hole transport layer 40, the light emitting layer 50 and the electron transport layer 60 as the organic layer 2-4, and the electrode layer 70 were sequentially vacuum-deposited by resistance heating in a 10-4 Pa vacuum chamber to form a continuous film.

Organic layer 1 (hole injection layer) (35 nm): PEDOT: PSS
Organic layer 2 (hole transport layer) (40 nm): TAPC
Organic layer 3 (light emitting layer) (35 nm): H-26 or CBP / G-2
Organic layer 4 (electron transport layer) (40 nm): TPBI
Electrode layer (0.5 nm / 100 nm): LiF / Al
A voltage was applied with the ITO 20 side of the obtained device as the anode and the Al side as the electrode layer 70 as the cathode, and current, luminance, and emission spectrum were measured. In the above measurement, oxygen and water are problems as the cause of element deterioration. To remove the cause, the dry box was taken out of the vacuum chamber without touching the air and sealed with a glass cap.

  In order to confirm the superiority of the Be complex over other host materials, the exemplary compound G-2 of a platinum complex was used as a guest material, and 6% by weight in various host materials (H-26, CBP) was doped by co-evaporation. Thus, a light emitting layer was formed. The light emitting layer 50 using the compound H-26 as the host material constitutes the organic light emitting device according to Example 6, and the light emitting layer using the conventionally used compound CBP as the host material relates to Comparative Example 7. An organic light emitting element is constituted.

  FIG. 4 is a graph showing applied voltage-luminance characteristics of the organic light emitting devices according to Example 6 and Comparative Example 7. This also applies to the following drawings. In FIG. 4, the characteristic indicated as H-26 is the characteristic of the organic light emitting element according to Example 6, and the characteristic indicated as CBP is the characteristic of the organic light emitting element according to Comparative Example 7. As shown in FIG. 4, the organic light emitting device according to Example 6 requires a higher voltage in the low luminance region than the organic light emitting device according to Comparative Example 7 to output the same luminance, but in the high luminance region. It can be seen that it can operate with a low driving voltage.

  FIG. 5 is a graph showing applied voltage-current density characteristics of the organic light emitting devices according to Example 6 and Comparative Example 7. In FIG. 5, the organic light emitting device according to Example 6 requires a higher voltage in the low luminance region than the organic light emitting device according to Comparative Example 7 to output the same current density, but is almost the same in the high luminance region. It turns out that it has a characteristic of a grade.

  FIG. 6 is a graph showing current density-external quantum efficiency characteristics of the organic light emitting devices according to Example 6 and Comparative Example 7. FIG. 6 shows that the organic light emitting device according to Example 6 has significantly higher external quantum efficiency characteristics than the organic light emitting device according to Comparative Example 7. Thus, according to the organic light emitting device according to Example 6, the external quantum efficiency can be greatly improved as compared with the conventional organic light emitting device.

  FIG. 7 is a graph showing the spectral characteristics of the organic light emitting devices according to Example 6 and Comparative Example 7. In FIG. 7, it can be seen that the organic light-emitting device according to Example 6 and the organic light-emitting device according to Comparative Example 7 show substantially the same spectral characteristics having a peak near 510 nm, and show green light-emitting characteristics. Therefore, according to the organic light emitting device according to Example 6, high luminous efficiency can be realized in the organic light emitting device that emits green light.

  As described above, by using the Be complex as a host material, an organic light-emitting element having higher luminous efficiency than CBP which is a conventional host material can be obtained.

  Note that Compound H-1, BAlq, Zn (BTP) 2 cannot be used as a host material when Compound G-2 is used as a guest material. This is because the triplet energy of the compound H-1, BAlq, Zn (BTP) 2 is smaller than the triplet energy (2.4 eV) of the compound G-2, so that high light emission efficiency cannot be obtained (non-native). (See Patent Document 3).

  On the other hand, the triplet energy of compound CBP is 2.6 eV, and the triplet energy of compound H-26 is 2.5 eV. Further, since it is preferable to use a material having a triplet energy larger than that of the guest material as the hole transport material, TAPC (2.8 eV) is used (a-NPD: 2.3 eV) (see Non-Patent Document 4). .

  [Embodiment 2]

  FIG. 8 is a view showing a display device according to Embodiment 2 of the present invention. The display device according to the second embodiment includes display means 90 and a drive circuit 100. The display unit 90 is a display panel that displays an image, and includes a plurality of pixels 80. Each of the pixels 80 is configured as the organic light emitting element according to the first embodiment, and is configured to display an image by self-emission.

  The driving circuit 100 is a driving unit that drives the display unit 90. The drive circuit 100 may include, for example, a vertical selection circuit 101 that performs vertical selection, and a horizontal readout circuit 102 that reads data of a selected scanning line. The configuration of the driving circuit 100 may be various configurations as long as the display unit 90 can be driven.

  As described above, the organic light emitting device according to the first embodiment can be used as a pixel of the display unit 90 to constitute a display device. According to the display device according to the second embodiment, since the organic light emitting elements constituting the pixels are configured with high efficiency and long life, a display device with high light emission efficiency and long life can be obtained.

  As described above, according to the organic light emitting device and the display device according to the present embodiment, a Zn complex is used as a host by using a Pt complex as a metal complex (Be complex) / guest including beryllium as a host of a light emitting layer. Luminous efficiency and device lifetime higher than that of the green device using the used red device and general materials as a host can be obtained. In addition, an organic light emitting device that combines a Be complex host and a Pt complex guest can obtain better performance than a device that combines a Be complex host and another metal complex guest (for example, an Ir complex).

  The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the above-described embodiments, and various modifications and substitutions can be made to the above-described embodiments without departing from the scope of the present invention. Can be added.

  The present invention can be used for a light-emitting element, a display element, a light-emitting device using the same, and an image display apparatus.

10 Substrate 20 ITO
30 hole injection layer (organic layer 1)
40 hole transport layer (organic layer 2)
50 Light emitting layer (organic layer 3)
60 Electron transport layer (organic layer 4)
70 Electrode layer 80 Pixel 90 Display means 100 Drive circuit 101 Vertical selection circuit 102 Horizontal readout circuit

Claims (8)

In an organic light emitting device including a light emitting layer composed of an organic layer between a pair of electrodes,
An organic light-emitting element, wherein the host material of the light-emitting layer is an organometallic complex containing beryllium, and the guest material is a phosphorescent platinum complex. The organic light-emitting device according to claim 1, wherein the host material contains a beryllium complex represented by the following general formula (1).

(In the formula, ring E, ring F and ring G each independently represent an aromatic ring or an aromatic heterocyclic ring which may have a substituent. N represents 0 or 1.) The organic light-emitting element according to claim 1, wherein the host material contains a beryllium complex represented by the following general formula (2).

(In the formula, each of ring H and ring J independently represents an aromatic ring or an aromatic heterocyclic ring which may have a substituent. N represents 0 or 1.) The organic light-emitting device according to any one of claims 1 to 3, wherein the guest material is a phosphorescent platinum complex represented by the following general formula (3).

(W ¹ , W ² , W ^3, and W ⁴ each represent a site that is coordinated or bonded to a platinum atom. V ¹ , V ^2, and V ³ are each a divalent atom (group), a single bond. (The bond represented by a broken line represents a single bond or a double bond, and the bond represented by a solid line represents a coordination bond or a covalent bond.) The organic light-emitting device according to claim 1, wherein the guest material is a phosphorescent platinum complex represented by the following general formula (4).

(In the formula, ring A, ring B, ring C and ring D are nitrogen-containing heterocycles in which any two of the rings may have a substituent, and the remaining two rings are substituents. The ring A, ring B, ring C, and ring D may each be condensed via a substituent to form a ring. Ring B, Ring C, and Ring D may further form a ring by condensing a plurality of substituents in the ring, and X ¹ , X ² , X ³ and X ⁴ are any two of them 2 represents a nitrogen atom coordinated to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom, and Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ and Y ⁶ are each independently carbon or nitrogen. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (group) or bond, Q ¹ and ring A and ring B, Q ² and ring A and ring C, Q ³ and ring And ring D may form a ring condensed via the respective substituents .Z ^{1, Z 2,} Z ³ and Z ^4, any two of indicates coordination bond, but the remaining two (Indicates a covalent bond, oxygen atom or sulfur atom.)   The organic light-emitting device according to claim 1, wherein the host material includes a metal complex other than a beryllium complex. The pair of electrodes includes an anode provided on a substrate, and a cathode disposed with a gap from the anode,
A hole transport layer between the light emitting layer and the anode;
The organic light-emitting device according to claim 1, further comprising an electron transport layer between the light-emitting layer and the cathode. A display element comprising the organic light-emitting element according to claim 1 as a pixel;
And a driving means for driving the display element.

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