JP2012049518A - Material for organic electroluminescent element, compound, organic electroluminescent element, display device, and luminaire - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a material for an organic electroluminescent element that has a high luminous efficiency, a low drive voltage, a high durability, and a small voltage rise at the time of driving, and to provide a compound composing constituting the material for the organic electroluminescent element, an organic electroluminescent element using the material for the organic electroluminescent element, a display device, and a luminaire.SOLUTION: There is provided a material for an organic electroluminescent element, which is a compound represented by general formula (1).

Description

  The present invention relates to an organic electroluminescent element material, a compound constituting the organic electroluminescent element material, an organic electroluminescent element using the organic electroluminescent element material, a display device, and an illumination device.

  Conventionally, as a light-emitting electronic display device, there is an electroluminescence display (hereinafter referred to as ELD). Examples of the constituent elements of ELD include inorganic electroluminescent elements and organic electroluminescent elements (hereinafter also referred to as organic EL elements).

  Inorganic electroluminescent elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements. On the other hand, an organic EL device has a structure in which a light-emitting layer containing a light-emitting compound is sandwiched between a cathode and an anode, and excitons (excitons) are generated by injecting electrons and holes into the light-emitting layer and recombining them. The device emits light by utilizing light emission (fluorescence / phosphorescence) when the exciton is deactivated. Organic EL elements can emit light at a voltage of several volts to several tens of volts, and are self-luminous, so they have a wide viewing angle, high visibility, and are thin-film, completely solid-state devices. It attracts attention from the viewpoint of space and portability.

However, for the future practical application of organic EL elements, it is desired to develop organic EL elements that can emit light efficiently and with high luminance with low power consumption, and that can reduce the voltage rise during driving. Yes.
Specifically, such a device is known in which a small amount of phosphor is doped into a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative to improve emission luminance and extend the lifetime of the device. . Moreover, the element which has an organic light emitting layer which doped 8-hydroxyquinoline aluminum complex as a host compound and a trace amount fluorescent substance to this, and the organic light emission which doped 8-quinoquinoline aluminum complex as a host compound and this to the quinacridone series pigment | dye Devices having layers are known.

  However, when light emission from excited singlet is used as described above, the generation ratio of singlet excitons and triplet excitons is 1: 3, so the generation probability of luminescent excited species is 25%. Since the extraction efficiency is about 20%, the limit of the external extraction quantum efficiency (η) is set to 5%. On the other hand, when the triplet is used, the upper limit of the internal quantum efficiency is 100%, so in principle the emission efficiency (external extraction quantum efficiency) is four times that of the excited singlet, which is almost equivalent to a cold cathode tube. It is attracting attention as a lighting application because there is a possibility that the above performance can be obtained.

For example, many heavy metal complexes, such as an iridium complex system, have been studied as dopants using excited triplets, and tris (2-phenylpyridine) iridium, L ₂ Ir (acac), (ppy) ₂ Ir (acac) are used as dopants. ), Tris (2- (p-tolyl) pyridine) iridium (Ir (ptpy) ₃ ), tris (benzo [h] quinoline) iridium (Ir (bzq) ₃ ), and the like have been studied (these) This metal complex is generally called an orthometalated iridium complex).

  In any of these cases, the light emission luminance and light emission efficiency of the light emitting device are greatly improved as compared with the conventional device because the emitted light is derived from phosphorescence. And as host compounds of these phosphorescent dopants, typified by 4,4′-bis (9-carbazolyl) biphenyl (CBP) and 1,3-bis (carbazol-9-yl) benzene (m-CP) The carbazole derivatives are well known. Further, m-CP and derivatives thereof are known as blue light emitting host compounds. However, even when these carbazole derivatives are used, the light emission efficiency and the lifetime have not been sufficiently satisfied (for example, see Patent Documents 1 and 2).

In addition, a host compound is disclosed in which a plurality of carbazole skeletons are bonded to a linking group at different positions (see, for example, Patent Document 3).
A compound in which a plurality of carbazole skeletons are bonded to a dibenzofuran skeleton is known (for example, see Patent Document 4). However, in these known documents, there is no description that the performance of the organic EL device is improved by introducing a substituent into the 4-position of the carbazole skeleton or the 1-position of the dibenzofuran skeleton. On the other hand, compounds having a substituent at the 4-position of fluorene are disclosed (see, for example, Patent Documents 5 and 6). The use of these has improved efficiency and lifetime to some extent, but further improvements have been demanded.
Furthermore, there has been a demand for an organic EL element with a low driving voltage and a small voltage increase during driving.

International Publication No. 03/80760 International Publication No. 04/74399 JP 2004-217557 A International Publication No. 06/128800 JP 2003-261471 A International Publication No. 07/072952

  As described above, various compounds relating to the organic EL element material have been disclosed in the past, and the light emission efficiency is high at a low driving voltage, the durability (life) is excellent, and the voltage increase during driving can be reduced. An attempt has been made to develop an organic EL element that can be used. However, it is desired to develop an organic EL device that further improves these performances compared to the conventional one.

  The present invention has been made in view of the above circumstances, and has high luminous efficiency, low driving voltage, high durability, and small increase in voltage during driving, and an organic electroluminescent element material constituting the same It is another object of the present invention to provide an organic electroluminescence element, a display device, and a lighting device using an organic electroluminescence element material.

The said subject of this invention can be achieved by the following structures.
1. An organic electroluminescence device material, which is a compound represented by the following general formula (1).

［式中、ＸはＯ、Ｓ、Ｓｅ、Ｎ−Ｒ、ＳＯ、ＳＯ_２のいずれかを表し、Ｒはアルキル基、シクロアルキル基、芳香族炭化水素基、非芳香族複素環基、芳香族複素環基、アルコキシカルボニル基、アリールオキシカルボニル基、アシル基から選ばれる何れかの基を表す。
Ｙは炭素数３以上のアルキル基、シクロアルキル基、アルケニル基、アルキニル基、芳香族炭化水素基、非芳香族複素環基、芳香族複素環基、アルコキシル基、シクロアルコキシル基、アリールオキシ基、アルキルチオ基、シクロアルキルチオ基、アリールチオ基、アルコキシカルボニル基、アリールオキシカルボニル基、スルファモイル基、ウレイド基、アシル基、アシルオキシ基、アミド基、カルバモイル基、スルフィニル基、アルキルスルホニル基、アリールスルホニル基、ＮＲ′Ｒ^〃（Ｒ′およびＲ^〃は各々水素原子、シクロアルキル基、芳香族炭化水素基、または、芳香族複素環基を表す。）、ニトロ基、シアノ基、ヒドロキシル基、アルキルシリル基、アリールシリル基、アルキルホスフィノ基、アリールホスフィノ基、アルキルホスホリル基、アリールホスホリル基、アルキルチオホスホリル基、アリールチオホスホリル基から選ばれる何れかの基を表す。
Ｒ_１〜Ｒ_７は、各々独立に水素原子、アルキル基、シクロアルキル基、アルケニル基、アルキニル基、芳香族炭化水素基、非芳香族複素環基、芳香族複素環基、ハロゲン原子、アルコキシル基、シクロアルコキシル基、アリールオキシ基、アルキルチオ基、シクロアルキルチオ基、アリールチオ基、アルコキシカルボニル基、アリールオキシカルボニル基、スルファモイル基、ウレイド基、アシル基、アシルオキシ基、アミド基、カルバモイル基、スルフィニル基、アルキルスルホニル基、アリールスルホニル基、アミノ基、ニトロ基、シアノ基、ヒドロキシル基、アルキルシリル基、アリールシリル基、アルキルホスフィノ基、アリールホスフィノ基、アルキルホスホリル基、アリールホスホリル基、アルキルチオホスホリル基、アリールチオホスホリル基から選ばれる何れかの基を表す。］

[Wherein, X represents any of O, S, Se, N—R, SO, SO ₂ , and R represents an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, a non-aromatic heterocyclic group, an aromatic group. It represents any group selected from a heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, and an acyl group.
Y is an alkyl group having 3 or more carbon atoms, cycloalkyl group, alkenyl group, alkynyl group, aromatic hydrocarbon group, non-aromatic heterocyclic group, aromatic heterocyclic group, alkoxyl group, cycloalkoxyl group, aryloxy group, Alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, NR ' R ^〃 (R ′ and R ^{各 々} each represent a hydrogen atom, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group), a nitro group, a cyano group, a hydroxyl group, an alkylsilyl group, an arylsilyl group Group, alkylphosphino group, arylphosphino group, al Ruhosuhoriru represents group, an aryl phosphoryl group, an alkyl thio phosphoryl group, one group selected from arylthio phosphoryl group.
R _{1 to} R ₇ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aromatic hydrocarbon group, non-aromatic heterocyclic group, aromatic heterocyclic group, halogen atom, alkoxyl group , Cycloalkoxyl group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkyl Sulfonyl, arylsulfonyl, amino, nitro, cyano, hydroxyl, alkylsilyl, arylsilyl, alkylphosphino, arylphosphino, alkylphosphoryl, arylphosphoryl, alkylthiophosphoryl, aryl It represents any group selected from the thiophosphoryl group. ]

2. Wherein Y in the general formula (1) The organic electroluminescent device material according to above, wherein the aromatic hydrocarbon group, a ^〃 aromatic heterocyclic group, or NR'R.

  3. 2. The organic electroluminescence element material according to 1, wherein Y in the general formula (1) is a group represented by the following general formula (2) or general formula (3).

［式中、Ｙ_１〜Ｙ_８は各々ＣまたはＮを表す。Ｒ_８〜Ｒ_１５は各々独立に前記一般式（１）におけるＲ_１〜Ｒ_７と同義の基を表し、Ｙ_１〜Ｙ_８のいずれかがＮである場合、該Ｎ原子に結合しているＲ_８〜Ｒ_１５は各々非共有電子対を表す。］

[Wherein Y _{1 to} Y ₈ each represent C or N. R _{8 to} R ₁₅ each independently represent a group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{1 to} Y ₈ is N, they are bonded to the N atom. R _{8 to} R ₁₅ each represent an unshared electron pair. ]

［式中、Ｙ_９〜Ｙ_１６は各々ＣまたはＮを表す。Ｒ_１６〜Ｒ_２３は各々独立に前記一般式（１）におけるＲ_１〜Ｒ_７と同義の基または連結基を表し、Ｙ_９〜Ｙ_１６のいずれかがＮである場合、該Ｎ原子に結合しているＲ_１６〜Ｒ_２３は各々非共有電子対を表す。Ｒ^〃′は水素原子、アルキル基、シクロアルキル基、芳香族炭化水素基、非芳香族複素環基、芳香族複素環基、アルコキシカルボニル基、アリールオキシカルボニル基、アシル基から選ばれる何れかの基を表す。］

[Wherein Y _{9 to} Y ₁₆ each represent C or N. R _{16 to} R ₂₃ each independently represents a group or a linking group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{9 to} Y ₁₆ is N, it is bonded to the N atom. R _{16 to} R ₂₃ each represent an unshared electron pair. R ^〃 'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, any of which is selected from acyl groups Represents a group. ]

  4). 4. The organic electroluminescent element material according to any one of 1 to 3, wherein X in the general formula (1) is O or N—R.

5). R ₁ at least one the following general formula of to R ₇ (4) or any one of the 1 to 4, wherein a group represented by the general formula (5) in the general formula (1) The organic electroluminescent element material described in 1.

［式中、Ｙ_１７〜Ｙ_２４は各々ＣまたはＮを表す。Ｒ_２４〜Ｒ_３１は各々独立に前記一般式（１）におけるＲ_１〜Ｒ_７と同義の基を表し、Ｙ_１７〜Ｙ_２４のいずれかがＮである場合、該Ｎ原子に結合しているＲ_２４〜Ｒ_３１は各々非共有電子対を表す。］

[Wherein Y _{17 to} Y ₂₄ each represent C or N. R _{24 to} R ₃₁ each independently represent a group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{17 to} Y ₂₄ is N, they are bonded to the N atom. R _{24 to} R ₃₁ each represent an unshared electron pair. ]

［式中、Ｙ_２５〜Ｙ_３２は各々ＣまたはＮを表す。Ｒ_３２〜Ｒ_３９は各々独立に前記一般式（１）におけるＲ_１〜Ｒ_７と同義の基または連結基を表し、Ｙ_２５〜Ｙ_３２のいずれかがＮである場合、該Ｎ原子に結合しているＲ_３２〜Ｒ_３９は各々非共有電子対を表す。Ｒ^〃′は水素原子、アルキル基、シクロアルキル基、芳香族炭化水素基、非芳香族複素環基、芳香族複素環基、アルコキシカルボニル基、アリールオキシカルボニル基、アシル基から選ばれる何れかの基を表す。］

[Wherein Y _{25 to} Y ₃₂ each represent C or N. R _{32 to} R ₃₉ each independently represent a group or a linking group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{25 to} Y ₃₂ is N, it is bonded to the N atom. R _{32 to} R ₃₉ each represent an unshared electron pair. R ^〃 'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, any of which is selected from acyl groups Represents a group. ]

  6). A compound represented by the following general formula (1):

［式中、ＸはＯを表す。Ｙは下記一般式（２）または一般式（３）の基を表す。Ｒ_１〜Ｒ_７は、各々独立に水素原子、アルキル基、シクロアルキル基、アルケニル基、アルキニル基、芳香族炭化水素基、非芳香族複素環基、芳香族複素環基、ハロゲン原子、アルコキシル基、シクロアルコキシル基、アリールオキシ基、アルキルチオ基、シクロアルキルチオ基、アリールチオ基、アルコキシカルボニル基、アリールオキシカルボニル基、スルファモイル基、ウレイド基、アシル基、アシルオキシ基、アミド基、カルバモイル基、スルフィニル基、アルキルスルホニル基、アリールスルホニル基、アミノ基、ニトロ基、シアノ基、ヒドロキシル基、アルキルシリル基、アリールシリル基、アルキルホスフィノ基、アリールホスフィノ基、アルキルホスホリル基、アリールホスホリル基、アルキルチオホスホリル基、アリールチオホスホリル基から選ばれる何れかの基を表す。］

[Wherein X represents O. Y represents a group of the following general formula (2) or general formula (3). R _{1 to} R ₇ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aromatic hydrocarbon group, non-aromatic heterocyclic group, aromatic heterocyclic group, halogen atom, alkoxyl group , Cycloalkoxyl group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkyl Sulfonyl, arylsulfonyl, amino, nitro, cyano, hydroxyl, alkylsilyl, arylsilyl, alkylphosphino, arylphosphino, alkylphosphoryl, arylphosphoryl, alkylthiophosphoryl, aryl It represents any group selected from the thiophosphoryl group. ]

［式中、Ｙ_１〜Ｙ_８は各々ＣまたはＮを表す。Ｒ_８〜Ｒ_１５は各々独立に前記一般式（１）におけるＲ_１〜Ｒ_７と同義の基を表し、Ｙ_１〜Ｙ_８のいずれかがＮである場合、該Ｎ原子に結合しているＲ_８〜Ｒ_１５は各々非共有電子対を表す。］

[Wherein Y _{1 to} Y ₈ each represent C or N. R _{8 to} R ₁₅ each independently represent a group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{1 to} Y ₈ is N, they are bonded to the N atom. R _{8 to} R ₁₅ each represent an unshared electron pair. ]

［式中、Ｙ_９〜Ｙ_１６は各々ＣまたはＮを表す。Ｒ_１６〜Ｒ_２３は各々独立に前記一般式（１）におけるＲ_１〜Ｒ_７と同義の基または連結基を表し、Ｙ_９〜Ｙ_１６のいずれかがＮである場合、該Ｎ原子に結合しているＲ_１６〜Ｒ_２３は各々非共有電子対を表す。Ｒ^〃′は水素原子、アルキル基、シクロアルキル基、芳香族炭化水素基、非芳香族複素環基、芳香族複素環基、アルコキシカルボニル基、アリールオキシカルボニル基、アシル基から選ばれる何れかの基を表す。］

[Wherein Y _{9 to} Y ₁₆ each represent C or N. R _{16 to} R ₂₃ each independently represents a group or a linking group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{9 to} Y ₁₆ is N, it is bonded to the N atom. R _{16 to} R ₂₃ each represent an unshared electron pair. R ^〃 'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, any of which is selected from acyl groups Represents a group. ]

  7). An organic electroluminescence device comprising an organic layer sandwiched between at least a pair of an anode and a cathode, wherein the organic layer comprises at least one layer including a light emitting layer, and at least one of the organic layers is the above-mentioned 1 to 1 6. An organic electroluminescence element comprising the organic electroluminescence element material according to any one of 5 above.

  8). 8. The organic electroluminescent device according to 7, wherein the light emitting layer contains the organic electroluminescent device material according to any one of 1 to 5.

  9. 8. The organic electroluminescence device as described in 7 above, wherein the layer containing the organic electroluminescence device material is a hole transport layer.

  10. 8. The organic electroluminescence device as described in 7 above, wherein the layer containing the organic electroluminescence device material is an electron transport layer.

  11. 11. The organic electroluminescence device according to any one of 7 to 10, wherein the light emitting layer contains a phosphorescent dopant.

  12 12. The organic electroluminescence device as described in 11 above, wherein the phosphorescent dopant is an Ir complex.

  13. The organic electroluminescence device according to any one of 7 to 12, wherein the organic electroluminescence device is manufactured by a wet process.

  14 A display device comprising the organic electroluminescence element according to any one of 7 to 12 above.

  15. It has an organic electroluminescent element of any one of said 7-12, The illuminating device characterized by the above-mentioned.

  According to the present invention, it is possible to provide an organic electroluminescence element material having high luminous efficiency, low driving voltage, high durability, and small voltage increase during driving. Moreover, the compound which comprises this organic EL element material can be provided. Moreover, the organic electroluminescent element using this organic EL element material, an illuminating device, and a display apparatus can be provided.

It is the schematic diagram which showed an example of the display apparatus comprised from an organic EL element used in an Example. It is a schematic diagram of the display part of the display apparatus in FIG.

  DESCRIPTION OF EMBODIMENTS Hereinafter, embodiments for carrying out the present invention will be described in detail, but the present invention is not limited thereto.

<< Organic EL element material (Organic electroluminescence element material) >>
The organic EL element material of the present invention will be described.
The organic EL device material of the present invention is a compound represented by the following general formula (1).

[Wherein, X represents O, S, Se, N—R, SO, or SO ₂ , and R represents a predetermined substituent. Y represents a predetermined substituent. R _{1 to} R ₇ each independently represent a hydrogen atom or a predetermined substituent. ]

  The organic EL device material of the present invention, which is a compound represented by the general formula (1), is preferably used for the light emitting layer of the organic EL device of the present invention, and particularly preferably used as a host compound in the light emitting layer. It is. The constituent layers and host compounds of the organic EL device of the present invention will be described in detail later.

  First, after explaining the background and characteristics of the invention of the organic EL device material, the compound represented by the general formula (1) will be described in detail.

Many compounds have been proposed for the skeleton represented by the general formula (1) including a carbazole skeleton and a dibenzofuran skeleton as host compounds and electron transport materials, but most of them are easy to introduce substituents. It was a compound in which a substituent was introduced at the 1st or 3rd position of the carbazole skeleton or the 2nd or 4th position of the dibenzofuran skeleton.
According to the present invention, as in the general formula (1), by introducing a substituent at the 1-position of the dibenzofuran skeleton or the 4-position of the carbazole skeleton, both high luminous efficiency and long life can be achieved. It was found that the driving voltage can be greatly reduced as compared with conventional compounds.
Such an effect is expressed because the organic EL material of the present invention has a substituent at a position having a large steric hindrance as shown in the general formula (1). When a substituent is introduced at the 1-position of the dibenzofuran skeleton or the 4-position of the carbazole skeleton, the planarity of the whole molecule is lowered and the compound has a larger steric hindrance, so that the interaction between the compounds is suppressed. Aggregation is suppressed. This facilitates interaction with a light emitting material such as a phosphorescent compound contained in the light emitting layer, and energy transfer to the light emitting material is further improved. As a result, the luminous efficiency can be further improved, the organic EL material can be prevented from being deteriorated, and the voltage can be lowered. Furthermore, the voltage rise during driving could be reduced.

<< Compound Represented by Formula (1) >>
The compound represented by the general formula (1) will be described.
First, after describing R _{1 to} R ₇ , X and Y will be described.
R _{1 to} R ₇ in the general formula (1) are each independently a hydrogen atom or a substituent, and examples of the substituent represented by each include an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, (T) butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group etc.), alkenyl group (eg, vinyl group) , Allyl group, etc.), alkynyl group (eg, propargyl group, etc.), aromatic hydrocarbon group (also called aryl group, eg, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, xylyl group, naphthyl group, anthryl group) Group, azulenyl group, acenaphthenyl group, fluorenyl group, phenanthryl group, indenyl group, pyrenyl , Biphenylyl group, etc.), non-aromatic heterocyclic group (for example, epoxy ring, aziridine ring, thiirane ring, oxetane ring, azetidine ring, thietane ring, tetrahydrofuran ring, dioxolane ring, pyrrolidine ring, pyrazolidine ring, imidazolidine ring, oxazolidine Ring, tetrahydrothiophene ring, sulfolane ring, thiazolidine ring, ε-caprolactone ring, ε-caprolactam ring, piperidine ring, hexahydropyridazine ring, hexahydropyrimidine ring, piperazine ring, morpholine ring, tetrahydropyran ring, 1,3-dioxane Ring, 1,4-dioxane ring, trioxane ring, tetrahydrothiopyran ring, thiomorpholine ring, thiomorpholine-1,1-dioxide ring, pyranose ring, diazabicyclo [2,2,2] -octane ring), aromatic Heterocyclic groups (pi Zyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, pyrazinyl group, triazolyl group (for example, 1,2,4-triazol-1-yl group, 1,2,3-triazole- 1-yl group, etc.), oxazolyl group, benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, furazanyl group, thienyl group, quinolyl group, benzofuryl group, dibenzofuryl group, benzothienyl group, dibenzothienyl group, indolyl Group, carbazolyl group, carbolinyl group, diazacarbazolyl group (in which one of the carbon atoms constituting the carboline ring of the carbolinyl group is replaced by a nitrogen atom), quinoxalinyl group, pyridazinyl group, triazinyl group, quinazolinyl group , Phthalazinyl group, etc.) Logen atom (for example, chlorine atom, bromine atom, iodine atom, fluorine atom), alkoxyl group (for example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, octyloxy group, dodecyloxy group, etc.) ), Cycloalkoxyl group (for example, cyclopentyloxy group, cyclohexyloxy group, etc.), aryloxy group (for example, phenoxy group, naphthyloxy group, etc.), alkylthio group (for example, methylthio group, ethylthio group, propylthio group, pentylthio group, Hexylthio group, octylthio group, dodecylthio group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.), alkoxycarbonyl group (eg, methyl Oxycarbonyl group, ethyloxycarbonyl group, butyloxycarbonyl group, octyloxycarbonyl group, dodecyloxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenyloxycarbonyl group, naphthyloxycarbonyl group, etc.), sulfamoyl group (eg, Aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2 -Pyridylaminosulfonyl group etc.), ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, Octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pyridylaminoureido group, etc.), acyl group (for example, acetyl group, ethylcarbonyl group, propylcarbonyl group, pentylcarbonyl group, cyclohexylcarbonyl group, octylcarbonyl group) 2-ethylhexylcarbonyl group, dodecylcarbonyl group, phenylcarbonyl group, naphthylcarbonyl group, pyridylcarbonyl group, etc.), acyloxy group (for example, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecyl) Carbonyloxy group, phenylcarbonyloxy group, etc.), amide group (for example, methylcarbonylamino group, ethylcarbonylamino group, dimethylcarbonylamino group, pro Rucarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonylamino group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc.), carbamoyl group (for example, amino Carbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylaminocarbonyl group, pentylaminocarbonyl group, cyclohexylaminocarbonyl group, octylaminocarbonyl group, 2-ethylhexylaminocarbonyl group, dodecylaminocarbonyl group, phenylaminocarbonyl group, Naphthylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), sulfinyl group (for example, methylsulfinyl group, ethyls Rufinyl group, butylsulfinyl group, cyclohexylsulfinyl group, 2-ethylhexylsulfinyl group, dodecylsulfinyl group, phenylsulfinyl group, naphthylsulfinyl group, 2-pyridylsulfinyl group, etc.), alkylsulfonyl group or arylsulfonyl group (for example, methylsulfonyl group) , Ethylsulfonyl group, butylsulfonyl group, cyclohexylsulfonyl group, 2-ethylhexylsulfonyl group, dodecylsulfonyl group, phenylsulfonyl group, naphthylsulfonyl group, 2-pyridylsulfonyl group, etc.), amino group (for example, amino group, ethylamino group) , Dimethylamino group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, anilino group, diarylamino group (for example, diphenylamino group) Nylamino group, dinaphthylamino group, phenylnaphthylamino group, etc.), naphthylamino group, 2-pyridylamino group, etc.), nitro group, cyano group, hydroxyl group, alkylsilyl group or arylsilyl group (for example, trimethylsilyl group, triethylsilyl group) Group, (t) butyldimethylsilyl group, triisopropylsilyl group, (t) butyldiphenylsilyl group, triphenylsilyl group, trinaphthylsilyl group, 2-pyridylsilyl group), alkylphosphino group or arylphosphino group (Dimethylphosphino group, diethylphosphino group, dicyclohexylphosphino group, methylphenylphosphino group, diphenylphosphino group, dinaphthylphosphino group, di (2-pyridyl) phosphosphino group), alkylphosphoryl group or arylphosphoryl (Dimethyl phosphoryl group, diethyl phosphoryl group, dicyclohexyl phosphoryl group, methylphenyl phosphoryl group, diphenyl phosphoryl group, dinaphthyl phosphoryl group, di (2-pyridyl) phosphoryl group), alkylthiophosphoryl group or arylthiophosphoryl group (dimethylthiophosphoryl group) , Diethylthiophosphoryl group, dicyclohexylthiophosphoryl group, methylphenylthiophosphoryl group, diphenylthiophosphoryl group, dinaphthylthiophosphoryl group, di (2-pyridyl) thiophosphoryl group) and the like. These groups may be further substituted with the above substituents, or they may be condensed with each other to form a ring.

At least one of R _{1 to} R ₇ is preferably a substituent, and more preferably any one or two of R _{1 to} R ₇ is a substituent. Of R _{1 to} R ₇ , any of R _{4 to} R ₇ is preferably a substituent, and more preferably, either R ₄ or R ₆ is a substituent. In the case where R ₄ is a substituent, the periphery of the heteroatom is shielded to increase the stability against charge, leading to improvement in durability, which is preferable. On the other hand, when R ₆ is a substituent, the durability is improved by blocking the active site, which is preferable.

When R _{1 to} R ₇ are substituents, preferred substituents are aromatic hydrocarbon groups, aromatic heterocyclic groups, amino groups, arylsilyl groups, and arylphosphoryl groups, among which aromatic hydrocarbons Is preferably any of a group, an aromatic heterocyclic group, and an amino group, and particularly preferably an aromatic heterocyclic group. In the case where R _{1 to} R ₇ are aromatic hydrocarbon groups, the stability to charge is high and the durability is improved.

  Further, when it is an amino group, it is mentioned as a more preferable form because it exhibits a high hole transport ability due to the electron donor property of the nitrogen atom of the amino group, and a diarylamino group is particularly preferable. Furthermore, when it is an aromatic heterocyclic group, it has the high charge transport ability and not only high durability against charges, but also has high thermal stability, so it is listed as the most preferable form. In particular, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, a carbolinyl group, a diazacarbazolyl group, and the like are more preferable forms. Can be mentioned.

In the most preferable form of R _{1 to} R ₇ in the general formula (1), more specifically, at least one of R _{1 to} R ₇ is represented by the general formula (4) or (5).

In the general formula (4), Y _{17 to} Y ₂₄ each represent C or N. When any one or more of Y _{17 to} Y ₂₄ is N, the charge transport property is improved, and a voltage increase during driving can be suppressed to a low level with a low voltage. Preferably Y ₁₇ to Y one or two either ₂₄ is a N, but still one of _Y 17 _{to Y 24} are mentioned as more preferred form to be N. On the other hand, when Y _{17 to} Y ₂₄ are all C, the durability can be further improved, so that it is mentioned as a preferable form. In general formula (4), it is preferable that all of Y _{17 to} Y ₂₄ are C.

R _{24 to} R ₃₁ each independently represents a group having the same meaning as R _{1 to} R ₇ in the general formula (1). When any of Y _{17 to} Y ₂₄ is N, R _{24 to} R ₃₁ bonded to the N atom each represent an unshared electron pair. R ₂₄ to R ₃₁ is preferably any one or more is a substituent, preferably a further one or two substituents among _R 24 _{to R 31,} in particular of the _R 24 _{to R 31} Most preferred is that only one is a substituent. Furthermore, it is preferable that R ₂₅ or R ₂₇ is a substituent, and it is particularly preferable that R ₂₅ is a substituent.

Preferable groups represented by R _{24 to} R ₃₁ include an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group, and an aromatic hydrocarbon group and an aromatic heterocyclic ring. A group and an amino group are more preferred substituents. Further, an aromatic hydrocarbon group or an aromatic heterocyclic group is particularly preferable. Therefore, in General Formula (4), R _{24 to} R ₃₁ are preferably such that R ₂₅ is an aromatic hydrocarbon group or an aromatic heterocyclic group, and R ₂₄ and R _{26 to} R ₃₁ are hydrogen atoms. Further preferred form. When any of R _{1 to} R ₇ in the general formula (1) is a group represented by the general formula (4), the compound represented by the general formula (1) has high charge transporting properties, thereby improving efficiency. Since it improves and durability also improves, it is mentioned as a preferable form.

In General Formula (5), Y _{25 to} Y ₃₂ each represent C or N. When any one or more of Y _{25 to} Y ₃₂ is N, the charge transporting property is improved, and the voltage rise during driving can be suppressed to a low voltage. Preferably Y ₂₅ to Y ₃₂ any one or two of an N, but still one of _Y 25 _{to Y 32} are mentioned as particularly preferred form to be N. In particular, it is preferable that any one of Y _{25 to} Y ₂₈ is N. On the other hand, when all of Y _{25 to} Y ₃₂ are C, the durability can be further improved, so that it is mentioned as a preferable form. In general formula (5), it is preferable that all of Y _{25 to} Y ₃₂ are C. For the atom bonded to the general formula _(1), attached at any atom of Y 29 _{to Y 32,} particularly preferably be combined in _{Y 31} or _{Y 32,} and most preferably bonded in _{Y 32.}

R _{32 to} R ₃₉ each independently represent a group or linking group having the same meaning as R _{1 to} R ₇ in the general formula (1). When any of Y _{25 to} Y ₃₂ is N, R _{32 to} R ₃₉ bonded to the N atom each represent an unshared electron pair. It is preferable that any one or more of R _{32 to} R ₃₉ is a substituent, and it is particularly preferable that only one of R _{32 to} R ₃₉ is a substituent. Furthermore, any of R _{32 to} R ₃₅ is preferably a substituent, more preferably R ₃₃ or R ₃₅ is a substituent, and most preferably R ₃₃ is a substituent. .

Preferable groups represented by R _{32 to} R ₃₉ include an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group, and an aromatic hydrocarbon group and an aromatic heterocyclic ring. A group and an amino group are more preferred substituents. Further, an aromatic hydrocarbon group or an aromatic heterocyclic group is particularly preferable. Therefore, in the general formula (5), R _{32 to} R ₃₉ are preferably bonded to the general formula (1) at R ₃₉ , and R ₃₃ is an aromatic hydrocarbon group or an aromatic heterocyclic group. It is more preferable that R ₃₂ and R _{34 to} R ₃₉ are hydrogen atoms.

R ^〃 'represents a hydrogen atom or a substituent, the alkyl group as a substituent, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group Represents any group selected from acyl groups, and most preferably an aromatic hydrocarbon group. When any _one of R _{1 to} R ₇ in the general formula (1) is a group represented by the general formula (5), the compound represented by the general formula (1) has high durability against electric charge, and is a nitrogen atom. As a result, the charge transportability is improved, and both the life and efficiency are improved.

X in the general formula (1) represents any of O, S, Se, N—R, SO, and SO ₂ , and is preferably O, S, or N—R, more preferably O or N—R. is there. R represents any group selected from an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, a non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, and an acyl group, preferably Is an aromatic hydrocarbon group or an aromatic heterocyclic group, and most preferably an aromatic hydrocarbon group.

In the general formula (1), Y represents an alkyl group having 3 or more carbon atoms, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, a non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxyl group, Cycloalkoxyl group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkylsulfonyl Group, arylsulfonyl group, NR′R ^〃 (R ′ and R ^{各 々} each represents a hydrogen atom, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group), a nitro group, a cyano group, a hydroxyl group Group, alkylsilyl group, arylsilyl group, alkylphosphino group, Ruhosufino group, an alkyl phosphoryl group, an aryl phosphoryl group, an alkyl thio phosphoryl group, or substituents selected from arylthio phosphoryl group.

  In the general formula (1), the alkyl group having 3 or more carbon atoms represented by Y is a linear or branched alkyl group such as propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group. Group, 2-ethylhexyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group and the like.

In the general formula (1), as NR′R ^〃 represented by Y, R ′ and R ^〃 each represent a hydrogen atom, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; ′ And R ^〃 may be bonded. Examples of the alkyl group, cycloalkyl group, aromatic hydrocarbon group, or aromatic heterocyclic group include the same compounds as those exemplified as the substituents represented by R _{1 to} R ₇ in the general formula (1). . As R 'and R ^〃 are given as it is desirable that the form is especially an aromatic hydrocarbon group or an aromatic heterocyclic group.

In general formula (1), an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, a non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxyl group, a cycloalkoxyl represented by Y Group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkylsulfonyl group, As arylsulfonyl group, nitro group, cyano group, hydroxyl group, alkylsilyl group, arylsilyl group, alkylphosphino group, arylphosphino group, alkylphosphoryl group, arylphosphoryl group, alkylthiophosphoryl group, arylthiophosphoryl group , And each compound exemplified as the substituents represented by R ₁ to R ₇ in the general formula (1) Example similar compounds.
In general formula (1), the group represented by Y may further have groups represented by R _{1 to} R ₇ in general formula (1).

  In the present invention, substitution of the above-mentioned substituent to Y in the general formula (1) strongly exerts the steric hindrance of the substituent, thereby suppressing aggregation of the compounds and achieving the object. . Surprisingly, in the general formula (1), this effect is remarkably exhibited particularly when a substituent is substituted at the Y position. The reason for this is unknown, but it is currently under intensive investigation.

In the general formula (1), Y is preferably an aromatic hydrocarbon group, an aromatic heterocyclic group, NR′R ^、, an arylsilyl group or an arylphosphoryl group, and particularly an aromatic hydrocarbon group or an aromatic heterocyclic ring. group, more preferably NR'R ^〃, further mentioned as the most preferred form is an aromatic heterocyclic group.

As the aromatic hydrocarbon group represented by Y, a phenyl group or a biphenyl group is preferable, and these groups preferably have a substituent. In particular, the atom bonded to the skeleton represented by the general formula (1) preferably has a substituent at the ortho-position or para-position, and more preferably has a substituent at the para-position. In the case of having a substituent at the ortho-position, the steric hindrance increases, resulting in a larger twist and an improvement in film quality. Moreover, when it has a substituent in a para position, since it leads to the durability improvement with respect to an electric charge by spreading electric charge distribution, it is mentioned as a preferable form. As the aromatic hydrocarbon group having a substituent, Y in the general formula (1) is more preferably represented by a group represented by the following general formula (A).
*-(Ar) n-LZ General formula (A)

In general formula (A), n represents an integer of 1 to 10, and * represents a bonding position. Ar represents an aromatic hydrocarbon group, and preferably has a substituent. Examples of the substituent substituted with Ar include a group having the same meaning as the substituent represented by R _{1 to} R ₇ in the general formula (1), and an aromatic hydrocarbon group or an aromatic heterocyclic group is preferable. . L represents a single bond or a linking group, and examples of the linking group represented by L include an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, a non-aromatic heterocyclic group, and an aromatic heterocyclic ring. Group, alkoxyl group, cycloalkoxyl group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, Sulfinyl group, alkylsulfonyl group, arylsulfonyl group, amino group, alkylsilyl group, arylsilyl group, alkylphosphino group, arylphosphino group, alkylphosphoryl group, arylphosphoryl group, alkylthiophosphoryl group, arylthiophosphoryl group, etc. All It is.

L is preferably a linking group, and is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group. Z includes a group having the same meaning as the group represented by R _{1 to} R ₇ in the general formula (1), and includes an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group. It is preferably an aromatic hydrocarbon group, an aromatic heterocyclic group or an amino group, more preferably an amino group or an aromatic heterocyclic group. Furthermore, it is preferable that Z contains one or more of a nitrogen atom, an oxygen atom, and a sulfur atom. In the case of containing a nitrogen atom, it is preferable because efficiency is improved by increasing the charge transport property, and more preferably an aromatic heterocyclic ring for improving thermal stability, such as a carbazolyl group, carbolinyl group, diazacarbazolyl. Groups are preferred. In particular, a carbazolyl group is one of the most preferred forms because it is thermally and electronically stable, leading to improved durability. Further, when it contains a substituent containing an oxygen atom or a sulfur atom, the charge state is stable and leads to improvement in durability, more preferably an aromatic heterocycle for improvement in thermal stability, A dibenzothienyl group or a dibenzofuryl group is particularly preferred. In particular, when it contains a dibenzofuryl group, it has a charge transport property, which leads to an improvement in efficiency and is one of the preferred forms.

Specifically, Y in the general formula (1) is a group represented by the following general formulas (6) to (31).

In General Formula (6) to General Formula (10), R _{40 to} R ₇₉ are each independently a hydrogen atom or a substituent, and the substituent represented by R _{40 to} R ₇₉ is, in General Formula (1), Examples thereof include the same substituents as the substituents represented by R _{1 to} R ₇ . Ar _{1 to} Ar ₁₀ represent an aromatic hydrocarbon group, and L1 to L5 represent a single bond or a linking group. Examples of the linking group represented by L1 to L5 include an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, a non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxyl group, and a cycloalkoxyl group. , Aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkylsulfonyl group, aryl Examples include sulfonyl group, amino group, alkylsilyl group, arylsilyl group, alkylphosphino group, arylphosphino group, alkylphosphoryl group, arylphosphoryl group, alkylthiophosphoryl group, arylthiophosphoryl group and the like. * Represents a bonding position.

In General Formula (11) to General Formula (14), R _{80 to} R ₁₀₇ are each independently a hydrogen atom or a substituent, and the substituent represented by R _{80 to} R ₁₀₇ is, in General Formula (1), Examples thereof include the same substituents as the substituents represented by R _{1 to} R ₇ . Ar _{11 to} Ar ₁₈ represent an aromatic hydrocarbon group, and L6 to L9 represent a single bond or a linking group. Examples of the linking group represented by L6 to L9 include the same linking groups as the linking groups represented by L1 to L5 in General Formula (6) to General Formula (10). * Represents a bonding position.

In General Formula (15) to General Formula (18), R _{108 to} R ₁₃₅ are each independently a hydrogen atom or a substituent, and the substituent represented by R _{108 to} R ₁₃₅ is, in General Formula (1), Examples thereof include the same substituents as the substituents represented by R _{1 to} R ₇ . Ar _{19 to} Ar ₂₆ represent an aromatic hydrocarbon group, and L10 to L13 represent a single bond or a linking group. Examples of the linking group represented by L10 to L13 include the same linking groups as the linking groups represented by L1 to L5 in General Formula (6) to General Formula (10). * Represents a bonding position.

In General Formula (19) to General Formula (23), R _{136 to} R ₁₇₅ are each independently a hydrogen atom or a substituent, and the substituent represented by R _{136 to} R ₁₇₅ is, in General Formula (1), Examples thereof include the same substituents as the substituents represented by R _{1 to} R ₇ . Ar _{27 to} Ar ₃₁ represent an aromatic hydrocarbon group, and * represents a bonding position. Ar ₂₇ to Ar ₃₁ may have a substituent, a case preferably has a substituent. In particular, it preferably has any one of an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group as a substituent, and further substitutes an aromatic hydrocarbon group or an aromatic heterocyclic group. More preferably, it has as a group.

Among the general formulas (19) to (23), the general formula (19), the general formula (20), or the general formula (22) is more preferable, and the general formula (22) is particularly preferable. It is more preferable. In the case of bonding at the 1-position of the carbazolyl group as represented by the general formula (19), it is preferable because the durability against electric charges is improved by shielding the periphery of the nitrogen atom, which is represented by the general formula (20). Thus, in the case of bonding at the 2-position of the carbazolyl group, since the distribution of the electric charge spreads to Ar ₂₈ , the durability is improved and it is mentioned as a preferable form. Moreover, when it couple | bonds with 4-position of a carbazolyl group so that it may represent with General formula (22), since a film quality improves because twist becomes large, it is preferable.

On the other hand, when it is bonded at the 3-position of the carbazolyl group as represented by the general formula (21), it is preferable that Ar ₂₉ further has a substituent. In this case, the electron donor property of the nitrogen atom is exhibited, so that the hole transport property is improved, and the durability is improved by spreading the charge distribution, which is preferable. Further, at least one of R _{152 to} R ₁₅₈ is preferably substituted, and more preferably R ₁₅₆ is substituted.

The substituent represented by R _{152 to} R ₁₅₈ is preferably an aromatic hydrocarbon group, an aromatic heterocyclic group, or a diarylamino group, and more preferably an aromatic hydrocarbon group. One. In addition, as represented by the general formula (23), when bonded with a nitrogen atom of a carbazolyl group, the light emission efficiency is improved, and particularly when bonded with an ortho position of an aromatic hydrocarbon group, It is preferable because the film quality is improved by twisting, and bonding to the para position of the aromatic hydrocarbon group is preferable because durability against charges is improved by spreading the distribution of charges. In particular, the case where it is bonded to the para position of the aromatic hydrocarbon group is mentioned as the most preferable form.

In General Formula (24) to General Formula (27), R _{176 to} R ₂₀₃ are each independently a hydrogen atom or a substituent, and the substituent represented by R _{176 to} R ₂₀₃ is, in General Formula (1), Examples thereof include the same substituents as the substituents represented by R _{1 to} R ₇ . In general formula (24), it is preferable that only one of R _{176 to} R ₁₈₂ is a substituent, and in general formula (26), only one of R _{190 to} R ₁₉₆ is substituted. It is preferably a group. Ar _{32 to} Ar ₃₅ represent an aromatic hydrocarbon group, and * represents a bonding position. Ar _{32 to} Ar ₃₅ may have a substituent, and preferably have a substituent. In particular, it preferably has any one of an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group as a substituent, and further substitutes an aromatic hydrocarbon group or an aromatic heterocyclic group. More preferably, it has as a group.

Among the general formulas (24) to (27), the general formula (24), the general formula (25), or the general formula (27) is more preferable, and the general formula (25) or It is preferable that it is General formula (27). In the case of bonding at the 1-position of the dibenzofuryl group as represented by the general formula (27), it is preferable because the film quality is improved by increasing the twist, and the 4-position as represented by the general formula (24). In this case, it is preferable that the periphery of the oxygen atom is shielded by twisting, thereby improving the stability of the charge and improving the durability. In particular, when Ar ₃₂ is substituted, it is durable due to the spread of the charge. It is more preferable because of improved properties. In the case of bonding at the 3-position of the dibenzofuryl group as represented by the general formula (25), since the distribution of the electric charge spreads to Ar ₃₃ , the durability is improved and it is mentioned as a preferable form. On the other hand, when it is bonded at the 2-position of the dibenzofuryl group as represented by the general formula (26), it is preferable that Ar ₃₄ is further substituted. In this case, it is preferable to improve the durability by blocking the active site of the oxygen atom and to improve the durability by spreading the charge distribution.

In General Formula (28) to General Formula (31), R _{204 to} R ₂₃₁ are each independently a hydrogen atom or a substituent, and the substituent represented by R _{204 to} R ₂₃₁ is, in General Formula (1), Examples thereof include the same substituents as the substituents represented by R _{1 to} R ₇ . However, in general formula (28), it is preferable that only one of R _{204 to} R ₂₁₀ is a substituent. In general formula (30), only one of R _{218 to} R ₂₂₄ is used. Is preferably a substituent. Ar _{36 to} Ar ₃₉ represent an aromatic hydrocarbon group, and * represents a bonding position. Ar _{36 to} Ar ₃₉ may have a substituent, and preferably have a substituent. In particular, it preferably has any one of an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group as a substituent, and further substitutes an aromatic hydrocarbon group or an aromatic heterocyclic group. More preferably, it has as a group.

Among the general formulas (28) to (31), the general formula (28), the general formula (29), or the general formula (31) is more preferable, and the general formula (29) or It is preferable that it is General formula (31). In the case of bonding at the 1-position of the dibenzothienyl group as represented by the general formula (31), the film quality is improved by increasing the twist, and the 4-position as represented by the general formula (28). In the case of bonding with, it is preferable because the periphery of the sulfur atom is shielded by twisting to increase the stability of the charge, leading to the improvement of the durability. In particular, when Ar ₃₆ is substituted, it is durable due to the spread of the charge. It is more preferable because of improved properties. In the case of bonding at the 3-position of the dibenzothienyl group as represented by the general formula (29), since the distribution of electric charge spreads to Ar ₃₇ , the durability is improved and it can be mentioned as a preferred form. On the other hand, Ar ₃₈ is preferably further substituted when bonded at the 2-position of the dibenzofuryl group as represented by the general formula (30). In this case, it is preferable because the durability can be improved by blocking the active site of the sulfur atom, and the durability can be improved by spreading the charge distribution.

As NR′R ^〃 represented by Y, R ′ or R ^〃 is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and more preferably an aromatic hydrocarbon group.
Examples of the aromatic heterocyclic group represented by Y include a pyrimidinyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, a carbolinyl group, a diazacarbazolyl group, and the like, and further an oxygen atom or nitrogen More preferred is a substituent containing an atom, and most preferred is a substituent containing a nitrogen atom. In the case of a substituent containing an oxygen atom, the charge state is stable and leads to improvement in durability, and a dibenzofuryl group is more preferable because it is particularly stable against charges. In particular, when bonded at the 1-position of the dibenzofuryl group, the twist becomes larger, leading to an improvement in film quality, and is cited as one of the particularly preferred forms, and further when bonded at the 3-position of the dibenzofuryl group, Since the spread of the charge distribution occurs, the durability is improved, and it is particularly preferable.

  In the case of bonding at the 2-position or 4-position of the dibenzofuryl group or dibenzothienyl group, Y in the general formula (1) preferably further has one substituent. In particular, the substituent preferably contains an aromatic hydrocarbon group or an aromatic heterocyclic group, and particularly preferably contains an aromatic hydrocarbon group as a substituent. When Y in the general formula (1) is a dibenzofuryl group or a dibenzothienyl group and further bonded to the general formula (1) at the 2-position or 4-position, Y in the general formula (1) further represents a substituent. By having more than one, durability, efficiency, etc. are significantly reduced. Although the cause of this is unknown, the present inventor added Y to a position having a large steric hindrance, and further substituted two or more substituents to further increase the steric hindrance so that an oxygen atom or a sulfur atom It was considered that the bonds located at the ortho-position and para-position of the destabilized with respect to the charge, and easily decomposed. On the other hand, a substituent containing a nitrogen atom is preferable because it improves efficiency by increasing the charge transport property, and particularly a carbazolyl group or carbolinyl group has high thermal and electronic stability and is durable. Since the improvement of property is seen, it is mentioned as the most preferable form.

  More specifically, Y in the general formula (1) is particularly preferably represented by the general formula (2) or (3).

In General Formula (2), Y _{1 to} Y ₈ each represent C or N. When any one or more of Y _{1 to} Y ₈ is N, the charge transport property is improved, and a voltage increase during driving can be suppressed to a low voltage. Preferably Y ₁ to Y ₈ either one or two of an N, but still one of _Y 1 to Y ₈ are mentioned as particularly preferred form to be N. On the other hand, when all of Y _{1 to} Y ₈ are C, the durability can be further improved, so that it is mentioned as a preferable form. In general formula (2), it is preferable that all of Y _{1 to} Y ₈ are C.

R _{8 to} R ₁₅ are each independently a group having the same meaning as R _{1 to} R ₇ in Formula (1). When any of Y _{1 to} Y ₈ is N, R _{8 to} R ₁₅ bonded to the N atom each represent an unshared electron pair. R ₈ to R ₁₅ is preferably any one or more is a substituent, preferably further is one or two substituents of _R 8 _{to R 15,} in particular of _R 8 _{to R 15} Most preferred is that only one is a substituent. Further, R ₉ or R ₁₁ is preferably a substituent, and R ₉ is particularly preferably a substituent. Preferable groups represented by R _{8 to} R ₁₅ include an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group, and an aromatic hydrocarbon group and an aromatic heterocyclic ring. A group and an amino group are more preferred substituents. Further, an aromatic hydrocarbon group or an aromatic heterocyclic group is particularly preferable. Therefore, in the general formula (2), R _{8 to} R ₁₅ are preferably such that R ₉ is an aromatic hydrocarbon group or an aromatic heterocyclic group, and R ₈ and R _{10 to} R ₁₅ are hydrogen atoms. This is the most preferred form.

In the general formula (3), Y _{9 to} Y ₁₆ each represent C or N. When any one or more of Y _{9 to} Y ₁₆ is N, the charge transport property is improved, and a voltage increase during driving can be suppressed to a low voltage. Preferably Y ₉ to Y ₁₆ any one or two of an N, but still one of _Y 9 _{to Y 16} are mentioned as particularly preferred form to be N. In particular, any of Y _{9 to} Y ₁₂ is preferably N. On the other hand, when all of Y _{9 to} Y ₁₆ are C, the durability can be further improved, so that it is mentioned as a preferable form. For the atom bonded to the general formula _(1), attached at any atom of Y 13 _{to Y 16,} particularly preferably be combined in _{Y 15} or _{Y 16,} and most preferably bonded in _{Y 16.} Particularly in the general formula (3), Y _{9 to} Y ₁₆ are each preferably C, and more preferably bonded to the general formula (1) at Y ₁₆ .

R _{16 to} R ₂₃ are each independently a group or linking group having the same meaning as R _{1 to} R ₇ in formula (1). When any of Y _{9 to} Y ₁₆ is N, R _{16 to} R ₂₃ bonded to the N atom each represent an unshared electron pair. It is preferable that any one or more of R _{16 to} R ₂₃ is a substituent, and it is particularly preferable that only one of R _{16 to} R ₂₃ is a substituent. Further, any one of R _{16 to} R ₁₉ is preferably a substituent, more preferably R ₁₇ or R ₁₉ is a substituent, and most preferably R ₁₇ is a substituent. . Preferable groups represented by R _{16 to} R ₂₃ include an aromatic hydrocarbon group, an aromatic heterocyclic group, an amino group, an arylsilyl group, and an arylphosphoryl group, and an aromatic hydrocarbon group and an aromatic heterocyclic ring. A group and an amino group are more preferred substituents. Further, an aromatic hydrocarbon group or an aromatic heterocyclic group is particularly preferable. Therefore, R _{16 to} R ₂₃ in General Formula (3) are preferably bonded to General Formula (1) at R ₂₃ , and R ₁₇ is more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group. Further, R ₁₆ and R _{18 to} R ₂₂ are particularly preferably a hydrogen atom.

R ^〃 'represents a hydrogen atom or a substituent, the alkyl group as a substituent, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group Represents any group selected from acyl groups, and most preferably an aromatic hydrocarbon group.
In a case where the compound of the general formula (1) is used as a host compound, preferred embodiments include that X is represented by O or N—R, and Y is represented by the general formula (2) or (3). In addition, high luminous efficiency and durability can be achieved. In order to achieve particularly high efficiency and durability, X is preferably represented by O, and most preferably Y ₁ to Y _{16 in the} general formula (2) or (3) are all C. It is mentioned as a preferable form. In addition, it is preferable that any one or more of R _{4 to} R _{7 in} the general formula (1) is represented by the general formula (4) or the general formula (5). Furthermore, it is most preferable that Y ₁₇ to Y ₃₂ in the general formula (4) or the general formula (5) are all C. That is, when used as a host compound, X is O, and Y is the general formula (2) or general formula (3) in which Y ₁ to Y ₁₆ are all C, and R ₆ is Y ₁₇ to Y. It is the most preferred form that the general formula (4) or the general formula (5) in which all ₃₂ are C.

Further, when used for the hole transport layer, high emission efficiency can be achieved when X is N and Y is represented by the general formula (2) or (3). It is mentioned as a more preferable form that Y is General formula (3). The case where Y ₉ to Y _{16 in} the general formula (3) are all C is particularly preferred.
When used for the electron transport layer, high emission efficiency can be achieved when X is N and Y is represented by the general formula (2) or (3). Furthermore, X is N and Y. It is mentioned as a more preferable form that is General formula (3). The case where any one of Y ₉ to Y _{16 in} the general formula (2) is N is particularly preferable.
Specific examples of the compound according to the present invention are shown below, but the present invention is not limited thereto.

  Hereinafter, although an example of the synthesis | combination of the compound represented by General formula (1) based on this invention is shown, this invention is not limited to these. Here, in particular, the synthesis of a compound in which X═O will be described in detail, but it can be similarly synthesized in other cases.

<< Synthesis Example; Synthesis of Exemplary Compound 1-35 >>
Exemplified compound 1-35 was synthesized by the following method.

(Synthesis of Intermediate 1)
8.0 g 2-bromo-3-methoxyaniline (39.6 mmol), 9.38 g 2,3-difluorophenylboronic acid (59.4 mmol), palladium acetate 0.89 g, 2- (dicyclohexylphosphino)- 130 ml of toluene was added to 6.50 g of 2 ′, 6′-dimethoxybiphenyl (S-Phos) and 25.2 g (119 mmol) of tripotassium phosphate, and the mixture was heated to reflux for 11 hours under a nitrogen stream. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The resulting oily crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 9) to obtain 3.26 g of intermediate 1 (yield 35%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

(Synthesis of Intermediate 2)
Under a nitrogen stream, 0.707 g of palladium acetate and 5 mL of a 50% xylene solution of tributylphosphine were added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 40 mL of dehydrated xylene, 3.2 g of intermediate 1 (12.6 mmol), 2,2′-dibromo-1,1′biphenyl 4.14 g (13.3 mmol), sodium t-butyrate 3.63 g (37 .8 mmol) was added and heated to reflux for 8 hours. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained oily crude product was purified by silica gel column chromatography (toluene: heptane = 1: 10) to obtain 3.2 g of intermediate 2 (yield 66%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

(Synthesis of Intermediate 3)
After cooling 83 mL of a methylene chloride solution of 3.2 g of Intermediate 2 (8.3 mmol) to −78 ° C., 25 mL of a methylene chloride solution of boron tribromide (1.0 mol / L) was slowly added dropwise. The reaction solution was returned to room temperature and stirred for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The resulting oily crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 4) to obtain 1.9 g of intermediate 3 (yield 62%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

(Synthesis of Intermediate 4)
To 50 mL of N, N-dimethylformamide, 1.9 g of Intermediate 3 (5.1 mmol) and 558 mg (7.7 mmol) of sodium hydride were added, and the mixture was stirred at 100 ° C. for 1 hour under a nitrogen stream. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (toluene: heptane = 1: 2) to obtain 1.6 g of intermediate 4 (yield 89%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
6.19 (d, J = 7.8 Hz, 1H), 6.78-6.84 (m, 1H), 7.07-7.12 (m, 3H), 7.28-7.35 (m 4H), 7.52 (d, J = 7.8 Hz, 1H), 7.70 (t, J = 8.1 Hz, 1H), 7.80 (d, J = 8.3 Hz, 1H), 8 .22 (dd, J = 6.1, 2.7 Hz, 2H).
MS (ES ⁺ ): m / z = 352 (M + 1) ⁺

(Synthesis of Exemplified Compound 1-35)
To 14 mL of N, N-dimethylformamide, 0.5 g (4.7 mmol) of carbazole, 1.5 g of intermediate 4 (4.3 mmol) and 465 mg (6.4 mmol) of sodium hydride were added, and heated for 8 hours under a nitrogen stream. Reflux was performed. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (toluene: heptane = 1: 4) to obtain 1.6 g (yield 78%) of Exemplary Compound 1-35. The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum. In addition, what further sublimated and refined this compound was used for preparation of the organic EL element mentioned later.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
6.57 (d, J = 7.8 Hz, 1H), 7.10 (t, J = 8.1 Hz, 1H), 7.21 (d, J = 7.8 Hz, 2H), 7.25 (d , J = 6.3 Hz, 2H), 7.31-7.43 (m, 8H), 7.53-7.56 (m, 2H), 7.59-7.67 (m, 2H), 8 20 (d, J = 7.8 Hz, 2H), 8.28 (d, J = 6.3 Hz, 2H).
MS (ES ^<+> ): m / z = 499 (M + 1) ^<+>

<< Synthesis Example; Synthesis of Exemplary Compound 1-31 >>
Exemplified Compound 1-31 was synthesized by the following method.

(Synthesis of Intermediate 5)
To 12 mL of an aqueous solution of 24.0 g (155.7 mmol) of 2-amino-3-nitrophenol, 40 mL (237.3 mmol) of 48% hydrobromic acid was added, and 11.2 g (162.3 mmol) of sodium nitrite was added under ice cooling. ) Was slowly added dropwise. After stirring for 15 minutes under ice cooling, a solution prepared by dissolving 24.6 g (171.5 mmol) of copper (I) bromide in 80 mL of 48% hydrobromic acid was slowly added dropwise. The mixture was further stirred for 15 minutes under ice cooling, then returned to room temperature, and further heated under reflux for 1 hour. The reaction solution was allowed to cool and then filtered, and the obtained brown solid was purified by silica gel column chromatography (toluene) to obtain 29.3 g of Intermediate 5 (yield 86%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

(Synthesis of Intermediate 6)
Under a nitrogen stream, 30.0 g (138 mmol) of Intermediate 5 and 9.9 g (207 mmol) of sodium hydride were added to 460 mL of a dimethylsulfoxide solution of 19.4 g (138 mmol) of 4-fluoronitrobenzene. The reaction solution was heated at 130 ° C. for 3 hours, allowed to cool, poured into water, and extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 4) to obtain 18.9 g of intermediate 6 (yield 41%). The structure was confirmed by nuclear magnetic resonance spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
7.03 (d, J = 9.3 Hz, 2H), 7.33 (dd, J = 8.1, 1.2 Hz, 1H), 7.54 (t, J = 8.1 Hz, 1H), 7 .71 (dd, J = 8.1, 1.2 Hz, 1H), 8.27 (d, J = 9.3 Hz, 2H).

(Synthesis of Intermediate 7)
Under a nitrogen stream, 12.9 g (93.3 mmol) of potassium carbonate and 1.25 g (5.55 mmol) of palladium acetate were added to 560 mL of a dimethylformamide solution of 18.9 g (55.7 mmol) of Intermediate 6. The reaction solution was heated at 150 ° C. for 4 hours and then allowed to cool. The insoluble material was filtered through Celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 4) to obtain 2.35 g of intermediate 6 (yield 16%). The structure was confirmed by nuclear magnetic resonance spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): Attribution of spectrum manufactured by JEOL Ltd. (chemical shift δ, peak shape, proton number)
7.74-7.79 (m, 2H), 8.02 (d, J = 8.3 Hz, 1H), 8.36 (d, J = 8.8 Hz, 1H), 8.56 (dd, J = 8.8, 2.4 Hz, 1 H), 9.67 (d, J = 2.4 Hz, 1 H).

(Synthesis of Intermediate 8)
2.35 g of Intermediate 7 was dissolved in 70 mL of tetrahydrofuran, 20 mL of ethanol and 0.24 g of 10% palladium / carbon were added, and the mixture was stirred for 10 hours under a hydrogen stream. After removing palladium by Celite filtration, the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 1) to obtain 0.8 g of intermediate 8 (yield 44%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): Attribution of spectrum manufactured by JEOL Ltd. (chemical shift δ, peak shape, proton number)
3.69 (s, 2H), 4.19 (s, 2H), 6.57 (d, J = 7.8 Hz, 1H), 6.78 (dd, J = 8.5, 2.2 Hz, 1H) ), 6.96 (d, J = 8.3 Hz, 1H), 7.14 (d, J = 2.0 Hz, 1H), 7.21 (t, J = 8.1 Hz, 1H), 7, 34 (D, J = 8.2 Hz, 1H).
MS (ES ⁺ ): m / z = 199 (M + 1) ⁺

(Synthesis of Exemplified Compound 1-31)
Under a nitrogen stream, 181 mg of palladium acetate was added to 1.3 mL of a 50% xylene solution of tributylphosphine, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 14 mL of dehydrated xylene, 0.8 g (4.04 mmol) of Intermediate 8, 2,2′-dibromo-1,1′-biphenyl 2.58 g (8.28 mmol), 1.16 g of sodium t-butylate ( 12.1 mmol) was added and heated to reflux for 6 hours. The reaction solution was allowed to cool, then filtered through Celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained oily crude product was purified by silica gel column chromatography (toluene: heptane = 1: 9) to obtain 0.55 g (yield 28%) of Exemplary Compound 1-31. The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum. In addition, what further sublimated and refined this compound was used for preparation of the organic EL element mentioned later.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
6.68 (d, J = 2.4 Hz, 1H), 6.89 (d, J = 7.3 Hz, 2H), 7.15-7.24 (m, 6H), 7.29 (t, J = 7.7 Hz, 2H), 7.41 (td, J = 7.7, 1.1 Hz, 2H), 7.53-7.56 (m, 2H), 7.71-7.77 (m, 2H), 7.82 (dd, J = 8.3, 1.1 Hz, 1H), 8.00 (dd, J = 7.8, 1.5 Hz, 2H), 8.04 (d, J = 7 .8Hz, 2H).
MS (ES ^<+> ): m / z = 499 (M + 1) ^<+>

<< Synthesis Example; Synthesis of Exemplified Compound 1-291 >>
Exemplified compound 1-291 was synthesized by the following method.

Exemplified Compound 1-291 can be synthesized in the same manner as Exemplified Compound 1-35 as briefly described below.
Intermediate 9 was synthesized by Suzuki coupling of 2-bromo-3-methylthioaniline and 3-difluorophenylboronic acid in the presence of palladium acetate and S-Phos. The amino group of Intermediate 9 and 2,2′-dibromo-1,1′biphenyl were reacted in the presence of palladium acetate and tributylphosphine to obtain Intermediate 10. The resulting intermediate 10 was treated with boron tribromide and converted to intermediate 11. Intermediate 12 was obtained by treating intermediate 11 with sodium hydride and cyclizing. Exemplified compound 1-291 was synthesized by reacting the obtained intermediate 12 with carbazole in the presence of sodium hydride.

<< Synthesis Example; Synthesis of Exemplary Compound 1-67 >>
Exemplary compound 1-67 was synthesized by the following method.

Exemplified Compound 1-67 can be synthesized in the same manner as Exemplified Compound 1-31 as briefly described below.
The amino group of 2-amino-3-nitrobenzenethiol was converted to Br by the Sandmeyer reaction to obtain Intermediate 13. Intermediate 14 was reacted with 3-fluoronitrobenzene in the presence of sodium hydride to synthesize intermediate 14. The intermediate 14 was treated with palladium acetate to be converted into the intermediate 15 and the nitro group of the obtained intermediate 15 was converted into an amino group by hydrogenation to obtain an intermediate 16. Intermediate 16 and 2,2′-dibromo-1,1′biphenyl were reacted in the presence of palladium acetate and tributylphosphine to synthesize Exemplified Compound 1-67.

<< Synthesis Example; Synthesis of Exemplary Compound 1-66 >>
Exemplary compound 1-66 was synthesized by the following method.

Exemplified Compound 1-66 can be synthesized in the same manner as Exemplified Compound 1-31 as briefly described below.
The primary amino group of 2-nitro-N-phenylbenzene-1,2-diamine was converted to Br by the Sandmeyer reaction to obtain Intermediate 17. Intermediate 18 was reacted with 3-fluoronitrobenzene in the presence of sodium hydride to synthesize intermediate 18. By treating the intermediate 18 with palladium acetate, the intermediate 18 was converted to the intermediate 19, and the nitro group of the obtained intermediate 19 was converted to an amino group by hydrogenation to obtain an intermediate 20. Intermediate 20 and 2,2′-dibromo-1,1′biphenyl were reacted in the presence of palladium acetate and tributylphosphine to synthesize Exemplified Compound 1-66.

<< Synthesis Example; Synthesis of Exemplary Compound 1-71 >>
Exemplary compound 1-71 was synthesized by the following method.

(Synthesis of Intermediate 22)
After dissolving 5.0 g of intermediate 21 (16.0 mmol) in 80 mL of ethylene glycol dimethyl ether, 20 mL of water was added, and 5.9 g of 3- (4,4,5,5-tetramethyl-1,3 was added thereto. , 2-Dioxaborolan-2-yl) -9-phenylcarbazole (16.0 mmol), 0.56 g of dichlorobistriphenylphosphine palladium, and 5.45 g (40.0 mmol) of potassium carbonate were added and heated under reflux for 5 hours under a nitrogen stream. did. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained oily crude product was purified by silica gel column chromatography (toluene: heptane = 1: 4) to obtain 5.0 g of intermediate 22 (yield 73%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
3.97 (s, 3H), 6.93 (dd, J = 8.3, 1.5 Hz, 1H) 7.08 (dd, J = 7.6, 1.2 Hz, 1H), 7.27− 7.31 (m, 1H), 7.34 (t, J = 7.8 Hz, 1H), 7.40-7.42 (m, 2H), 7.45-7.50 (m, 3H), 7.61 (t, J = 2.9 Hz, 4H), 8.12-8.16 (m, 2H).

(Synthesis of Intermediate 23)
After cooling 77 mL of methylene chloride solution of 3.3 g of intermediate 22 (7.7 mmol) to −78 ° C., 23 mL of methylene chloride solution of boron tribromide (1.0 mol / L) was slowly added dropwise. The reaction solution was returned to room temperature and stirred for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The resulting oily crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 5) to obtain 2.9 g of intermediate 23 (yield 91%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
5.80 (s, 1H), 7.02-7.07 (m, 2H), 7.27-7.32 (m, 2H), 7.51-7.42 (m, 5H), 7. 56-7.65 (m, 4H), 8.13-8.16 (m, 2H).

(Synthesis of Intermediate 24)
Under a nitrogen stream, 0.8 g (1.93 mmol) of Intermediate 23 and 1.26 g (3.86 mmol) of cesium carbonate were added to 4 mL of a dimethylformamide solution of 0.27 g (1.93 mmol) of 4-fluoronitrobenzene for 2 hours. Heated to reflux. After allowing to cool, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 9) to obtain 0.9 g of intermediate 24 (yield 87%). The structure was confirmed by nuclear magnetic resonance spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
7.06 (d, J = 8.8 Hz, 2H), 7.16 (dd, J = 7.8, 2.2 Hz, 1H), 7.33-7.29 (m, 1H), 7.40 -7.44 (m, 3H), 7.47-7.51 (m, 4H), 7.60-7.65 (m, 4H), 8.16 (d, J = 7.8 Hz, 1H) , 8.20 (s, 1H), 8.25 (d, J = 9.3 Hz, 2H).

(Synthesis of Intermediate 25)
Under a nitrogen stream, 0.9 g (1.68 mmol) of the intermediate 24 in 24 mL of a dimethylacetamide solution was added to potassium carbonate 460 mg (3.36 mmol), palladium acetate 38 mg (0.168 mmol), tricyclohexylphosphonium tetrafluoroborate 125 mg (0 .336 mmol) was added. The reaction solution was heated at 140 ° C. for 3 hours and then allowed to cool. Insoluble material was filtered through Celite, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 2) to obtain 0.6 g of intermediate 25 (yield 79%). The structure was confirmed by nuclear magnetic resonance spectrum.

The measurement conditions, chemical shift of each peak of the obtained spectrum, proton number, etc. are shown below.
¹ H-NMR (400 MHz, CDCl 3)
Measuring apparatus: JEOL JNM-AL400 (400 MHz): manufactured by JEOL Ltd. Spectrum attribution (chemical shift δ, peak shape, proton number)
7.32 (td, J = 7.1, 2.4 Hz, 1H), 7.45-7.54 (m, 4H), 7.60-7.66 (m, 4H), 7.67-7 .70 (m, 5H), 8.16 (d, J = 7.8 Hz, 1H), 8.34 (dd, J = 9.0, 2.2 Hz, 1H), 8.38 (d, J = 1.5 Hz, 1H), 8.56 (d, J = 2.4 Hz, 1H).

(Synthesis of Intermediate 26)
2.35 g of the intermediate 25 was dissolved in 40 mL of tetrahydrofuran, 40 mL of ethanol and 0.6 g of 5% palladium / carbon were further added, and the mixture was stirred for 2 hours under a hydrogen stream. After removing palladium by Celite filtration, the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate: heptane = 1: 4) to obtain 0.45 g of intermediate 26 (yield 80%). The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

(Synthesis of Intermediate 27)
To 5 mL of a hydrochloric acid solution of 0.45 g (1.06 mmol) of the intermediate 26, 1 mL of an aqueous solution of 88 mg (1.27 mmol) of sodium nitrite was added dropwise under ice cooling. After stirring for 15 minutes under ice cooling, a solution of 530 mg (3.18 mmol) of potassium (I) iodide dissolved in 3 mL of hydrochloric acid was slowly added dropwise. The mixture was further stirred for 15 minutes under ice cooling, then returned to room temperature, and further heated under reflux for 2 hours. The reaction solution was allowed to cool and then poured into 30% aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 426 mg (yield 75%) of intermediate 27. The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum.

(Synthesis of Exemplary Compound 1-71)
426 mg of intermediate 27 (0.80 mmol) was dissolved in 4 mL of ethylene glycol dimethyl ether, and then 1 mL of water was added, and 235 mg of 2- (dibenzofuran-2-yl) -4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (0.8 mmol), dichlorobistriphenylphosphine palladium 56 mg (0.08 mmol) and potassium carbonate 272 mg (2.0 mmol) were added, and the mixture was heated to reflux for 4 hours under a nitrogen stream. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was repeatedly washed with water and concentrated under reduced pressure. The resulting oily crude product was purified by silica gel column chromatography to obtain 408 mg (yield 89%) of Exemplary Compound 1-71. The structure was confirmed by nuclear magnetic resonance spectrum and mass spectrum. In addition, what further sublimated and refined this compound was used for preparation of the organic EL element mentioned later.

<< Organic EL element (Organic electroluminescence element) >>
Next, the organic EL element of the present invention will be described.
The organic EL element of the present invention is an element containing an organic layer sandwiched between at least a pair of an anode and a cathode. And the said organic layer consists of at least 1 layer containing a light emitting layer, and at least 1 layer contains the organic EL element material of this invention demonstrated above among this organic layer.

  Note that “at least one layer including a light emitting layer” essentially includes a light emitting layer and may be one light emitting layer, or together with this light emitting layer, for example, a hole injection layer or a hole transport described below. It means that an organic layer such as a layer, a hole blocking layer, an electron transport layer, and an electron injection layer may be included. That is, it means an organic layer composed of one light emitting layer or a light emitting layer and one or more other organic layers.

<Structure layers of organic EL elements>
The constituent layers of the organic EL element of the present invention will be described. In the present invention, preferred specific examples of the layer structure of the organic EL element are shown below, but the present invention is not limited thereto.
(I) Anode / light emitting layer / electron transport layer / cathode (ii) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (iii) Anode / hole transport layer / light emitting layer / hole blocking layer / electron Transport layer / cathode (iv) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (v) anode / hole transport layer / light emitting layer / electron transport layer / electron injection Layer / cathode (vi) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (vii) anode / hole injection layer / hole transport layer / light emitting layer / hole Blocking layer / electron transport layer / electron injection layer / cathode In addition to the hole blocking layer, an electron blocking layer can also be used as the blocking layer.

  In the present invention, each layer of the organic EL element may contain the compound represented by the general formula (1), and among them, any one or more of a hole transport layer, a light emitting layer, and an electron transport layer are included. It is preferable to contain in a layer, and it is more preferable to contain in a light emitting layer or an electron carrying layer. Furthermore, it is more preferable to contain the compound represented by the general formula (1) in the light emitting layer, and it is particularly preferable to contain the compound as a host compound.

  In the organic EL device of the present invention, the blue light emitting layer preferably has an emission maximum wavelength of 430 to 480 nm, the green light emitting layer has an emission maximum wavelength of 510 to 550 nm, and the red light emitting layer has an emission maximum wavelength of 600 to 640 nm. A monochromatic light emitting layer in the range is preferable, and a display device using these is preferable. Alternatively, a white light emitting layer may be formed by laminating at least three light emitting layers. Further, a non-light emitting intermediate layer may be provided between the light emitting layers. The organic EL element of the present invention preferably emits white light and is preferably a lighting device using these.

Next, each layer which comprises the organic EL element of this invention is demonstrated.
[Light emitting layer]
The light emitting layer is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer. The portion that emits light may be within the layer of the light emitting layer or at the interface between the light emitting layer and the adjacent layer.
The total thickness of the light emitting layer is not particularly limited, but it is 2 nm from the viewpoint of film uniformity, preventing application of an unnecessary high voltage during light emission, and improving the stability of the emission color with respect to the drive current. It is preferable to adjust to the range of -5 micrometers, More preferably, it is the range of 2-200 nm, Most preferably, it is the range of 10-20 nm.
For the production of the light-emitting layer, a light-emitting dopant or a host compound, which will be described later, is formed and formed by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink-jet method. it can.

  The light emitting layer of the organic EL device of the present invention preferably contains a light emitting host compound and at least one kind of light emitting dopant (such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant).

(Host compound (also called luminescent host))
The host compound used in the present invention is not particularly limited in terms of structure, but is typically a carbazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing heterocyclic compound, a thiophene derivative, a furan derivative, an oligo Those having a basic skeleton such as an arylene compound, or a carboline derivative or a diazacarbazole derivative (here, a diazacarbazole derivative is a nitrogen atom in which at least one carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative is a nitrogen atom) And the like.) And the like.

As the host compound, the above host compounds may be used alone or in combination of two or more. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient. Moreover, it becomes possible to mix different light emission by using multiple types of the compound containing the partial structure represented by the said General formula (1), and the light emission dopant mentioned later, and can obtain arbitrary luminescent colors by this. it can.
The host compound used in the present invention may be a conventionally known low molecular compound or a high molecular compound having a repeating unit, and a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (deposition polymerization property). Light emitting host).

As the known host compound that may be used in combination, a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
Specific examples of known host compounds include compounds described in the following documents.
JP-A-2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357777, 2002-334786, 2002-8860, 2002-334787, 2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002-75645, 2002-338579, 2002-105445 gazette, 2002-343568 gazette, 2002-141173 gazette, 2002-352957 gazette, 2002-203683 gazette, 2002-363227 gazette, 2002-231453 gazette, No. 003-3165, No. 2002-234888, No. 2003-27048, No. 2002-255934, No. 2002-286061, No. 2002-280183, No. 2002-299060, No. 2002. -302516, 2002-305083, 2002-305084, 2002-308837, and the like.

(Luminescent dopant)
As the light-emitting dopant, a fluorescent dopant (also referred to as a fluorescent compound) or a phosphorescent dopant (also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like) can be used. Here, it is preferable that the light emitting layer which comprises the organic EL element of this invention contains a phosphorescence dopant. However, from the viewpoint of obtaining an organic EL device with higher luminous efficiency, the light emitting dopant (sometimes simply referred to as a light emitting material) used in the light emitting layer or the light emitting unit of the organic EL device of the present invention is the above general formula. It is preferable to contain the compound containing the partial structure represented by (1) as a phosphorescent dopant.

(Phosphorescent dopant)
A phosphorescent dopant is a compound in which light emission from an excited triplet is observed. Specifically, it is a compound that emits phosphorescence at room temperature (25 ° C.) and is defined as a compound having a phosphorescence quantum yield of 0.01 or more at 25 ° C., but a preferable phosphorescence quantum yield is 0. .1 or more.
The phosphorescence quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. Although the phosphorescence quantum yield in a solution can be measured using various solvent, the phosphorescence dopant should just achieve the said phosphorescence quantum yield (0.01 or more) in any solvent.

  There are two types of light emission of phosphorescent dopants in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the host compound, and this energy is transferred to the phosphorescent dopant. It is an energy transfer type to obtain light emission from a phosphorescent dopant. The other is a carrier trap type in which a phosphorescent dopant serves as a carrier trap, and carrier recombination occurs on the phosphorescent dopant to emit light from the phosphorescent dopant. In any case, it is a condition that the excited state energy of the phosphorescent dopant is lower than the excited state energy of the host compound.

The phosphorescent dopant is preferably a complex compound containing a group 8-10 metal in the periodic table, more preferably an iridium compound, an osmium compound, a platinum compound (platinum complex compound), or a rare earth complex. Among them, the most preferable is an iridium compound (that is, an Ir complex).
In this invention, a well-known phosphorescence dopant can be used as a phosphorescence dopant used for the light emitting layer of an organic EL element.
Although the specific example of the well-known compound used as a phosphorescence dopant below is shown, as a phosphorescence dopant, it is not limited to these. These compounds are described, for example, in Inorg. Chem. 40, 1704-1711, and the like.

(Fluorescent dopant (also called fluorescent compound))
Fluorescent dopants (fluorescent compounds) include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes Examples thereof include dyes, stilbene dyes, polythiophene dyes, and rare earth complex phosphors.

[Electron transport layer]
The electron transport layer is a layer made of a material having a function of transporting electrons. The electron transport layer can be provided as a single layer or a plurality of layers.
In the case of a single-layer electron transport layer and a plurality of layers, as an electron transport material used for an electron transport layer adjacent to the cathode side with respect to the light emitting layer, a function of transmitting electrons injected from the cathode to the light emitting layer Use what has. As the material, the organic EL element material according to the present invention can be used as an electron transporting material to achieve the effects of the present invention. However, in addition, any one of conventionally known compounds can be selected and used in combination as long as the effect of the organic EL element material (that is, the electron transport material) according to the present invention is not impaired. Examples include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like. Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be exemplified. Furthermore, the polymeric material which introduce | transduced these materials into the polymer chain, or made these materials into the polymeric principal chain can also be mentioned.

Also, metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc., and the central metals of these metal complexes are In, Mg, Cu , Ca, Sn, Ga or Pb can also be mentioned as metal complexes. In addition, metal-free or metal phthalocyanine, or those having a terminal substituted with an alkyl group or a sulfonic acid group can also be used. Moreover, inorganic semiconductors, such as a distyrylpyrazine derivative and n-type-Si and n-type-SiC, can also be mentioned.
The electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Although there is no restriction | limiting in particular about the film thickness of an electron carrying layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. The electron transport layer may have a single layer structure composed of one or more of the above materials.

It can also be used as an electron transport layer having a high n property doped with impurities. Examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
It is preferable to use such an n-type electron transport layer because an element with lower power consumption can be manufactured.

[Injection layer: electron injection layer, hole injection layer]
The injection layer is a layer provided as necessary, and includes an electron injection layer and a hole injection layer. The injection layer may be present between the anode and the hole transport layer or between the cathode and the electron transport layer as shown in the above layer configuration. Alternatively, it may exist between the anode and the light emitting layer or between the cathode and the light emitting layer.
An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance. “Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).

The details of the anode buffer layer (hole injection layer) are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069 and the like. As a specific example, copper phthalocyanine is used. Examples thereof include a phthalocyanine buffer layer represented by an oxide, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc. Metal buffer layer typified by lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc. . The buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 μm although it depends on the material.

[Blocking layer: hole blocking layer, electron blocking layer]
The blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film. For example, it is described in JP-A Nos. 11-204258, 11-204359, and “Organic EL elements and their forefront of industrialization” (issued by NTT, Inc. on November 30, 1998). There is a hole blocking (hole blocking) layer.
The hole blocking layer has a function of an electron transporting layer in a broad sense, and is made of a hole blocking material having a function of transporting electrons and an extremely small ability to transport holes. By blocking holes while transporting electrons, the recombination probability of electrons and holes can be improved. Moreover, the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer as needed.
In addition, it is preferable that the hole-blocking layer of the organic EL element of this invention is provided adjacent to the light emitting layer.

The hole blocking layer preferably contains the carbazole derivative, carboline derivative or diazacarbazole derivative mentioned as the host compound.
Further, in the present invention, when a plurality of light emitting layers having different emission colors are provided, the light emitting layer having the shortest wavelength of the light emission maximum wavelength (shortest wave layer) is closest to the anode among all the light emitting layers. preferable. In such a case, it is preferable to additionally provide a hole blocking layer between the shortest wave layer and the light emitting layer next to the anode next to the shortest wave layer. Furthermore, it is preferable that 50% by mass or more of the compound contained in the hole blocking layer provided at this position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave layer.

The ionization potential is defined by the energy required to emit an electron at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and can be obtained by the following method, for example.
(1) Using Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.), a molecular orbital calculation software manufactured by Gaussian, USA The ionization potential can be obtained as a value obtained by rounding off the second decimal place of the value (eV unit converted value) calculated by performing structural optimization using B3LYP / 6-31G *. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
(2) The ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy. For example, a method known as ultraviolet photoelectron spectroscopy can be suitably used by using a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd.

  On the other hand, the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed. The film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 to 100 nm, and more preferably 5 to 30 nm.

[Hole transport layer]
The hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. The hole transport layer can be provided as a single layer or a plurality of layers.
The hole transport material has any of hole injection or transport and electron barrier properties, and may be either organic or inorganic. For example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
The above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.

  Representative examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N'-tetraphenyl-4,4'-diaminophenyl; N, N'-diphenyl-N, N'- Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminophenyl) phenylmethane; N, N'-diphenyl-N, N ' − (4-methoxyphenyl) -4,4'-diaminobiphenyl; N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether; 4,4'-bis (diphenylamino) quadriphenyl; N, N, N-tri (p-tolyl) amine; 4- (di-p-tolylamino) -4 '-[4- (di-p-tolylamino) styryl] stilbene; 4-N, N-diphenylamino- (2-diphenylvinyl) benzene; 3-methoxy-4'-N, N-diphenylaminostilbenzene; N-phenylcarbazole, as well as two of those described in US Pat. No. 5,061,569 Having a condensed aromatic ring in the molecule, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-308 4,4 ', 4 "-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the like.

Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used. In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
JP-A-11-251067, J. Org. Huang et al. A so-called p-type hole transport material as described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used. In the present invention, these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
The hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can. Although there is no restriction | limiting in particular about the film thickness of a positive hole transport layer, Usually, 5 nm-about 5 micrometers, Preferably it is 5-200 nm. This hole transport layer may have a single layer structure composed of one or more of the above materials.

Alternatively, a hole transport layer having a high p property doped with impurities can be used. Examples thereof include JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
In the present invention, it is preferable to use a hole transport layer having such a high p property because a device with lower power consumption can be produced.

[anode]
As the anode in the organic EL element, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ , and ZnO. Alternatively, an amorphous material such as IDIXO (In ₂ O ₃ —ZnO) capable of forming a transparent conductive film may be used. For the anode, these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 μm or more) A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material. Or when using the substance which can be apply | coated like an organic electroconductivity compound, wet film-forming methods, such as a printing system and a coating system, can also be used. When light emission is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually in the range of 10 to 1000 nm, preferably in the range of 10 to 200 nm.

[cathode]
On the other hand, as the cathode, a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O ₃ ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like. Among these, from the point of durability against electron injection and oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this, for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al ₂ O ₃ ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually selected in the range of 10 nm to 5 μm, preferably 50 to 200 nm. In order to transmit the emitted light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the emission luminance is advantageously improved.
Moreover, after producing the metal with a film thickness of 1 to 20 nm on the cathode, a transparent or translucent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode, By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.

Next, matters other than the constituent layers related to the organic EL element will be described.
[Support substrate]
The support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.

  Examples of the resin film include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones, Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or Appel (trade name, manufactured by Mitsui Chemicals) Can be mentioned.

An inorganic film, an organic film, or a hybrid film of both may be formed on the surface of the resin film, and the water vapor permeability (25 ± 0.5 ° C.) measured by a method according to JIS K 7129-1992. , Relative humidity (90 ± 2)% RH) is preferably 0.01 g / (m ² · 24 h) or less, and further, oxygen measured by a method according to JIS K 7126-1987. Permeability is 10 ⁻³ cm ³ / (m ² · 24 h · atm) or less (1 atm is 1.01325 × 105 Pa) Water vapor permeability is 10 ⁻³ g / (m ² · 24 h) or less A barrier film is preferred, and the water vapor permeability is more preferably 10 ⁻⁵ g / (m ² · 24 h) or less.
As a material for forming the barrier film, any material may be used as long as it has a function of suppressing entry of elements that cause deterioration of elements such as moisture and oxygen. For example, silicon oxide, silicon dioxide, silicon nitride, or the like can be used. Further, in order to improve the brittleness of the film, it is more preferable to have a laminated structure of these inorganic layers and organic material layers. Although there is no restriction | limiting in particular about the lamination | stacking order of an inorganic layer and an organic layer, It is preferable to laminate | stack both alternately several times.

  The method for forming the barrier film is not particularly limited. For example, the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used. However, an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.

Examples of the opaque support substrate include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
The external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more. Here, the external extraction quantum efficiency (%) = the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element × 100.
In addition, a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor. In the case of using a color conversion filter, the λmax of light emission of the organic EL element is preferably 480 nm or less.

[Sealing]
As a sealing means used for this invention, the method of adhere | attaching a sealing member, an electrode, and a support substrate with an adhesive agent can be mentioned, for example.
The sealing member should just be arrange | positioned so that the display area | region of an organic EL element may be covered, and concave plate shape or flat plate shape may be sufficient as it. Further, transparency and electrical insulation are not particularly limited.
Specifically, a glass plate, a polymer plate (film), a metal plate (film), etc. are mentioned. Examples of the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz. Examples of the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone. Examples of the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.

In the present invention, a polymer film and a metal film can be preferably used because the element can be thinned. Furthermore, the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 × 10 ⁻³ cm ³ / (m ² · 24 h · atm) or less, and conforms to JIS K 7129-1992. The water vapor permeability (25 ± 0.5 ° C., relative humidity (90 ± 2)% RH) measured by the above method is preferably 1 × 10 ⁻³ g / (m ² · 24 h) or less.
For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.

Specific examples of the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups such as acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to. Moreover, heat | fever and chemical curing types (two-component mixing), such as an epoxy type, can be mentioned. Moreover, hot-melt type polyamide, polyester, and polyolefin can be mentioned. Moreover, a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
In addition, since an organic EL element may deteriorate by heat processing, what can be adhesive-hardened from room temperature to 80 degreeC is preferable. A desiccant may be dispersed in the adhesive. Application | coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.

  In addition, it is also preferable that the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film. . In this case, the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen. For example, silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can. Further, in order to improve the brittleness of the film, it is preferable to have a laminated structure of these inorganic layers and layers made of organic materials. The method for forming these films is not particularly limited. For example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster-ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma A polymerization method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.

In the gap between the sealing member and the display area of the organic EL element, an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase. preferable. A vacuum is also possible. Moreover, a hygroscopic compound can also be enclosed inside.
Examples of the hygroscopic compound include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate). Etc.), metal halides (eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.), perchloric acids (eg perchloric acid) Barium, magnesium perchlorate, and the like), and anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.

[Protective film, protective plate]
In order to increase the mechanical strength of the element, a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film. In particular, when the sealing is performed by the sealing film, the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate. As a material that can be used for this, the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used, but the polymer film is light and thin. Is preferably used.

[Light extraction]
The organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle θ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the element side surface.
As a method for improving the light extraction efficiency, for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the interface between the transparent substrate and the air (US Pat. No. 4,774,435), A method of improving efficiency by providing a light collecting property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on a side surface of an element (Japanese Patent Laid-Open No. 1-220394), and light emission from a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No. 62-172691), a flat having a lower refractive index between the substrate and the light emitter than the substrate A method of introducing a layer (Japanese Patent Laid-Open No. 2001-202827), a method of forming a diffraction grating between any one of a substrate, a transparent electrode layer and a light emitting layer (including between the substrate and the outside) (Japanese Patent Laid-Open No. 11-283951) Gazette).

In the present invention, these methods can be used in combination with the organic EL device of the present invention. However, a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
In the present invention, by combining these means, it is possible to obtain an element having higher luminance or durability.
When a medium having a low refractive index is formed between the transparent electrode and the transparent substrate with a thickness longer than the wavelength of light, the light extracted from the transparent electrode has a higher extraction efficiency to the outside as the refractive index of the medium is lower.
Examples of the low refractive index layer include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.

The thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
The method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency. This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction. Light that cannot be emitted due to total internal reflection, etc. is diffracted by introducing a diffraction grating in any layer or medium (in the transparent substrate or transparent electrode), and the light is emitted outside. I want to take it out.

The introduced diffraction grating desirably has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much. However, by making the refractive index distribution a two-dimensional distribution, light traveling in all directions is diffracted, and light extraction efficiency is increased.
As described above, the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or in the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated. At this time, the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium. The arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.

[Condenser sheet]
The organic EL device of the present invention is processed on the light extraction side of the substrate so as to provide, for example, a microlens array structure, or combined with a so-called condensing sheet, for example, with respect to a specific direction, for example, the device light emitting surface. By condensing in the front direction, the luminance in a specific direction can be increased.
As an example of the microlens array, quadrangular pyramids having a side of 30 μm and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate. One side is preferably 10 μm to 100 μm. If it becomes smaller than this, the effect of diffraction will generate | occur | produce and color, and if too large, thickness will become thick and is not preferable.

As the condensing sheet, for example, a sheet that is put into practical use in an LED backlight of a liquid crystal display device can be used. As such a sheet, for example, a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used. As the shape of the prism sheet, for example, a substrate may be formed by forming a triangle (triangular) stripe with a vertex angle of 90 degrees and a pitch of 50 μm, a shape with a rounded vertex, and a pitch. The shape may be changed at random, or other shapes.
Moreover, in order to control the light emission angle from a light emitting element, you may use together a light diffusing plate and a film with a condensing sheet. For example, a diffusion film (light-up) manufactured by Kimoto Co. can be used.

<< Method for producing organic EL element >>
As an example of the method for producing the organic EL device of the present invention, a method for producing an organic EL device comprising an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode will be described.
First, a desired electrode material, for example, a thin film made of an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably 10 to 200 nm, thereby producing an anode.
Next, an organic compound thin film of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which are organic EL element materials, is formed thereon.
As a method for forming each of these layers, there are a vapor deposition method, a wet process (spin coating method, casting method, ink jet method, printing method) and the like. However, in the present invention, it is preferable to produce an organic EL element by a wet process. By producing it by a wet process, it is possible to obtain an effect such that a homogeneous film can be easily obtained and pinholes are hardly generated. Among these, film formation by a coating method such as a spin coating method, an ink jet method, or a printing method is preferable. These coating methods have the advantage that they are highly efficient, simple and easy to increase in area, and according to the ink jet method, they have the advantage that they can be applied in units of pixels.

Examples of the liquid medium for dissolving or dispersing the organic EL device material according to the present invention include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, Aromatic hydrocarbons such as mesitylene and cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as DMF and DMSO can be used. Moreover, as a dispersion method, it can disperse | distribute by dispersion methods, such as an ultrasonic wave, high shear force dispersion | distribution, and media dispersion | distribution.
After these layers are formed, a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a thickness of 1 μm or less, preferably in the range of 50 to 200 nm. By providing, a desired organic EL element can be obtained.
In addition, it is also possible to reverse the production order and produce the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode in this order. When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode. An alternating voltage may be applied. The alternating current waveform to be applied may be arbitrary.

《Display device, lighting device》
The display device or illumination device of the present invention comprises the above-described organic EL element of the present invention (specific examples of the display device and illumination device will be described in “Usage” described later). That is, an organic EL element material that is a compound represented by the general formula (1) is used.
Since the display device or lighting device of the present invention uses the organic EL element of the present invention, it can be driven at a low voltage, and the voltage rise during driving is small. In addition, since the light emission efficiency is high and the durability is excellent, the device can have a long lifetime.

<Application>
The organic EL element of the present invention can be used as a display device, a display, and various light emission sources. For example, lighting devices (home lighting, interior lighting), clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light Examples include, but are not limited to, the light source of the sensor. However, it can be effectively used particularly as a backlight of a liquid crystal display device and an illumination light source.

  In the organic EL element of the present invention, patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation. In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned. In the fabrication of the element, a conventionally known method is used. Can do.

The light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with the total CS-1000 (manufactured by Konica Minolta Sensing) is applied to the CIE chromaticity coordinates.
When the organic EL element of the present invention is a white element, white means that the chromaticity in the CIE1931 color system at 1000 cd / m ² is X when the 2 ° viewing angle front luminance is measured by the above method. = 0.33 ± 0.07 and Y = 0.33 ± 0.1.

  Hereinafter, the present invention will be specifically described with reference to Examples 1 to 10, but the scope of the present invention is not limited thereto.

[Example 1]
<< Production of Organic EL Element 1-1 >>
An organic EL element was produced as follows.
Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass) made of ITO (indium tin oxide) with a thickness of 100 nm on a glass substrate of 100 mm × 100 mm × 1.1 mm as an anode The substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes. This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus. Meanwhile, 200 mg of α-NPD is put into a molybdenum resistance heating boat, 200 mg of CBP is put into another resistance heating boat made of molybdenum, and another resistance made of molybdenum. 200 mg of bathocuproin (BCP) is put in a heating boat, 100 mg of phosphorescent compound tris (2-phenylviridinate) iridium (III) (Ir (ppy) ₃ ) is put in another molybdenum resistance heating boat, and another molybdenum 200 mg of tris (8-quinolinolato) aluminum (Alq ₃ ) was put in a resistance heating boat and attached to a vacuum deposition apparatus.

Next, after reducing the vacuum chamber to 4 × 10 −4 Pa, the heating boat containing α-NPD was energized and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec. A hole transport layer was provided. Further, the heating boat containing CBP and the phosphorescent compound Ir (ppy) ₃ was energized and heated, and co-deposited on the hole transport layer at a deposition rate of 0.2 nm / sec and 0.012 nm / sec, respectively. A light emitting layer having a thickness of 35 nm was provided. In addition, the substrate temperature at the time of vapor deposition was room temperature. Further, an electron transport layer that also serves as a hole blocking function with a film thickness of 10 nm is provided by energizing and heating the heating boat containing BCP and depositing on the light emitting layer at a deposition rate of 0.1 nm / sec. It was. On top of that, the heating boat containing Alq ₃ was further energized and heated, and was deposited on the electron transport layer at a deposition rate of 0.1 nm / sec to provide an electron injection layer having a thickness of 40 nm. . In addition, the substrate temperature at the time of vapor deposition was room temperature.
Then, 0.5 nm of lithium fluoride and 110 nm of aluminum were vapor-deposited, the cathode was formed, and the organic EL element 1-1 was produced.

<< Production of Organic EL Elements 1-2 to 1-22 >>
In the production of the organic EL element 1-1, organic EL elements 1-2 to 1-22 were produced in the same manner except that the CBP of the light emitting layer as shown in Table 1 was replaced with the compounds shown in Table 1.

The structural formulas of BCP, Alq ₃ , Ir (ppy) ₃ , α-NPD, and CBP used in this example are shown below.

また、比較化合物としては下記のものを用いた。

The following compounds were used as comparative compounds.

<< Evaluation of organic EL elements >>
The produced organic EL element was evaluated as follows, and the results are shown in Table 1.
(Luminescence efficiency)
In the organic EL element 1-1, current started to flow at an initial driving voltage of 3 V, and green light was emitted from the phosphorescent compound that was the dopant of the light emitting layer. About the produced organic EL element, luminous efficiency (lm / W) when a 10 V DC voltage was applied under a dry nitrogen gas atmosphere at room temperature (about 23 to 25 ° C.) was measured. The luminous efficiency was expressed as a relative value when the organic EL element 1-1 was 100.

(durability)
The half-life time, which is the time required for the initial luminance to drop to half of the original luminance when driven at a constant current of ^2.5 mA / cm ² at room temperature, was expressed as an index. The half-life time was expressed as a relative value when the organic EL element 1-1 was taken as 100.

(Drive voltage)
Each voltage was measured when the organic EL element was driven at room temperature and under a constant current condition of ^2.5 mA / cm ² , and the measurement results are as follows. Indicated by value.
Drive voltage = (initial drive voltage of each element / initial drive voltage of the organic EL element 1-1) × 100
In addition, it shows that a drive voltage is small with respect to a comparison, so that a value is small.

(Change in drive voltage over time)
The organic EL device was continuously lit under a constant current condition of ^2.5 mA / cm ² at room temperature, and the driving voltage when the luminance reached 70% of the initial luminance was measured. The measurement results are shown as relative values so that the organic EL element 1-1 (comparison) becomes 100 as shown below.
Drive voltage change 1 = (drive voltage when the luminance of the organic EL element 1-1 is 70%) / (initial drive voltage of the organic EL element 1-1)
Change in drive voltage of each element = (drive voltage at 70% luminance of each element) / (initial drive voltage of each element)
Drive voltage change (τ ^1/7 ) = (Drive voltage change of each element) / (Drive voltage change 1) × 100

  From Table 1, it can be seen that the organic EL device of the present invention is excellent in luminous efficiency, high in durability and long in life, and is an excellent organic EL device. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 2]
<< Production of Organic EL Elements 2-1 to 2-22 >>
Preparation of the organic EL device 1-1 was completely performed except that the phosphorescent compound Ir (ppy) ₃ of the organic EL device 1-1 of Example 1 was replaced with the compound Ir-15 described above and CBP was replaced with the compounds shown in Table 2. Organic EL elements 2-1 to 2-22 were produced by the same method. About these elements which show blue light emission, the light emission efficiency, durability, and drive voltage were measured by the same method as Example 1. The obtained results are shown in Table 2.

  From Table 2, it can be seen that the blue light-emitting organic EL device of the present invention is an excellent blue light-emitting organic EL device having excellent luminous efficiency, high durability and long life. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 3]
<< Production of Organic EL Elements 3-1 to 3-22 >>
The organic EL device 1-1 was completely the same as the organic EL device 1-1 except that the phosphorescent compound Ir (ppy) ₃ of the organic EL device 1-1 of Example 1 was replaced with the compound Ir-9 described above, and CBP was replaced with the compounds shown in Table 2. Organic EL elements 3-1 to 3-22 were produced by the same method. With respect to these elements exhibiting red light emission, light emission efficiency, durability, and driving voltage were measured in the same manner as in Example 1. The obtained results are shown in Table 3.

  From Table 3, it can be seen that the red light-emitting organic EL device of the present invention is excellent in luminous efficiency, high in durability and long in life, and is an excellent red light-emitting organic EL device. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 4]
<< Production of Organic EL Elements 4-1 to 4-40 >>
The organic EL device 1-1 was completely the same as the organic EL device 1-1 except that the phosphorescent compound Ir (ppy) ₃ of the organic EL device 1-1 of Example 1 was replaced with the compound Ir-17 described above and CBP was replaced with the compounds shown in Table 4. Organic EL elements 4-1 to 4-40 were produced by the same method. About these elements which show blue light emission, the light emission efficiency, durability, and drive voltage were measured by the same method as Example 1. Table 4 shows the obtained results.

  From Table 4, it can be seen that the blue light-emitting organic EL device of the present invention is an excellent blue light-emitting organic EL device having excellent luminous efficiency, high durability and long life. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 5]
<< Production of Organic EL Elements 5-1 to 5-18 >>
Organic EL elements 5-1 to 5-18 were produced in exactly the same manner except that the hole transport layer of the organic EL element 1-1 of Example 1 was replaced with the compounds shown in Table 5. About these elements which show green light emission, the light emission efficiency, durability, and the drive voltage were measured by the method similar to Example 1. FIG. The results obtained are shown in Table 5.

  From Table 5, it can be seen that the green light-emitting organic EL device of the present invention is excellent in luminous efficiency, high in durability and long in life, and is an excellent green light-emitting organic EL device. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 6]
<< Production of Organic EL Elements 6-1 to 6-18 >>
Organic EL elements 6-1 to 6-18 were prepared in exactly the same manner except that α-NPD of the organic EL element 1-1 of Example 1 was replaced with TPD and the electron transport layer was replaced with the compounds shown in Table 6.
The structural formula of TPD used in this example is shown below.

  About these elements which show green light emission, the light emission efficiency, durability, and the drive voltage were measured by the method similar to Example 1. FIG. The results obtained are shown in Table 6.

  From Table 6, it can be seen that the green light-emitting organic EL device of the present invention is excellent in luminous efficiency, has high durability and has achieved a long life, and is an excellent green light-emitting organic EL device. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 7]
<< Production of Organic EL Element 7-1 >>
After patterning on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) on a 100 mm × 100 mm × 1.1 mm glass substrate as an anode, this ITO transparent electrode was provided. The transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.

On this transparent support substrate, a solution obtained by diluting poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) to 70% with pure water at 3000 rpm for 30 seconds. After forming the film by spin coating, the film was dried at 200 ° C. for 1 hour to provide a hole transport layer having a thickness of 30 nm.
This substrate was transferred to a nitrogen atmosphere, and on the hole transport layer, a solution of 3 mg of the hole transport material 1 and 40 mg of the hole transport material 2 dissolved in 10 ml of toluene was added at 1500 rpm for 30 seconds. A thin film was formed by spin coating on the transport layer.

Further, ultraviolet light was irradiated for 180 seconds to carry out photopolymerization and crosslinking, thereby forming a second hole transport layer having a thickness of about 20 nm.
On this second hole transport layer, a thin film was formed by spin coating using a solution of 100 mg CBP and 10 mg Ir-15 dissolved in 10 ml toluene at 600 rpm for 30 seconds. It vacuum-dried at 60 degreeC for 1 hour, and was set as the light emitting layer with a film thickness of about 70 nm.
Next, a thin film was formed on the light emitting layer by a spin coating method using a solution of 50 mg of ET-40 dissolved in 10 ml of hexafluoroisopropanol (HFIP) at 1000 rpm for 30 seconds.

Furthermore, it vacuum-dried at 60 degreeC for 1 hour, and was set as the electron carrying layer with a film thickness of about 30 nm.
Subsequently, this substrate is fixed to a substrate holder of a vacuum deposition apparatus, and the vacuum chamber is depressurized to 4 × 10 −4 Pa. Then, lithium fluoride is deposited to 0.4 nm and aluminum is further deposited to 110 nm as a cathode buffer layer. And an organic EL element 7-1 was produced.

<< Production of Organic EL Elements 7-2 to 7-40 >>
Organic EL elements 7-2 to 7-40 were prepared in the same manner as in the preparation of the organic EL element 7-1 except that CBP of the light emitting layer was replaced with the compounds shown in Table 7.
The structural formulas of the hole transport material 1, the hole transport material 2, and ET-40 used in this example are shown below.

  About these elements which show blue light emission, the light emission efficiency, durability, and drive voltage were measured by the same method as Example 1. The results obtained are shown in Table 7.

  From Table 7, it can be seen that the blue light-emitting organic EL device of the present invention is an excellent blue light-emitting organic EL device having excellent luminous efficiency, high durability and long life. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 8]
<< Production of Organic EL Elements 8-1 to 8-18 >>
In the organic EL element 7-1 of Example 7, Ir-15 was replaced with Ir (ppy) ₃ and CBP was replaced with the compound shown in Table 8. 8-1 to 8-18 were produced. About these elements which show green light emission, the light emission efficiency, durability, and the drive voltage were measured by the method similar to Example 1. FIG. Table 8 shows the obtained results.

  From Table 8, it can be seen that the green light-emitting organic EL device of the present invention is excellent in luminous efficiency, high in durability and long in life, and is an excellent green light-emitting organic EL device. Further, it can be seen that the drive voltage is lowered and the voltage rise during driving is suppressed. Moreover, it turns out that higher luminous efficiency and lifetime can be made compatible by making the organic EL element material which concerns on this invention into a more preferable aspect (for example, a preferable substituent, the number of this substituent, etc.). It can also be seen that the drive voltage can be lowered and the voltage rise during driving can be reduced.

[Example 9]
Organic EL element 1-5 (green light emitting organic EL element), organic EL element 2-5 (blue light emitting organic EL element), and organic EL element 3-5 (red light emitting organic EL element) prepared in Examples 1 to 3 The active matrix type full-color display device (display) 1 shown in FIG. 1 was manufactured. FIG. 2 shows only a schematic diagram of the display unit A of the produced full-color display device 1 (reference numeral B is a control unit). That is, a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) on the same substrate. Each of the scanning lines 5 and the plurality of data lines 6 in the wiring portion is made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a lattice shape and are connected to the pixels 3 at the orthogonal positions (details). Is not shown).

The plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. Then, an image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, full-color display is possible by appropriately juxtaposing the red, green, and blue pixels.
By driving the full-color display device 1, a clear full-color moving image display with low voltage, high brightness and good durability was obtained.

  In addition, organic EL elements 1-6 to 1-22 as green light emitting organic EL elements, 2-6 to 2-22 as blue light emitting organic EL elements, and organic EL elements 3-6 to 3 as red light emitting organic EL elements. Even when 22 was randomly combined, full-color display was possible.

[Example 10]
<< Preparation of white organic EL element >>
After patterning on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) on a 100 mm × 100 mm × 1.1 mm glass substrate as an anode, this ITO transparent electrode was provided. The transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.

On this transparent support substrate, a solution obtained by diluting poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) to 70% with pure water at 3000 rpm for 30 seconds. After forming the film by spin coating, the film was dried at 200 ° C. for 1 hour to provide a hole transport layer having a thickness of 30 nm.
The substrate was transferred to a nitrogen atmosphere, and on the hole transport layer, Exemplified Compound 1-320 (60 mg), Compound Ir-9 (3.0 mg) and Ir-12 (3.0 mg) were dissolved in 6 ml of toluene. Was formed by spin coating under the conditions of 1000 rpm and 30 seconds. Heating was performed in vacuum at 150 ° C. for 1 hour to obtain a light emitting layer.

Furthermore, using a solution obtained by dissolving BCP (20 mg) in 6 ml of cyclohexane, a film was formed by spin coating under conditions of 1000 rpm and 30 seconds. Heating was performed in vacuum at 80 ° C. for 1 hour to form a first electron transport layer.
Subsequently, this substrate was fixed to a substrate holder of a vacuum vapor deposition apparatus, and 200 mg of Alq ₃ was put into a molybdenum resistance heating boat and attached to the vacuum vapor deposition apparatus. After depressurizing the vacuum chamber to 4 × 10 ⁻⁴ Pa, energize and heat the heating boat containing Alq ₃ , and deposit on the first electron transport layer at a deposition rate of 0.1 nm / second, Further, a second electron transport layer having a thickness of 40 nm was provided.
In addition, the substrate temperature at the time of vapor deposition was room temperature.

Then, 0.5 nm of lithium fluoride and 110 nm of aluminum were vapor-deposited, the cathode was formed, and the white light emitting organic EL element was produced.
When this element was energized, almost white light was obtained, and it was found that it could be used as a lighting device. In addition, it turned out that white light emission is obtained similarly even if it replaces with the other compound of illustration.

1. Display device (display)
3 pixels 5 scanning lines 6 data lines A display unit B control unit

Claims (15)

An organic electroluminescence device material, which is a compound represented by the following general formula (1).

[Wherein, X represents any of O, S, Se, N—R, SO, SO ₂ , and R represents an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, a non-aromatic heterocyclic group, an aromatic group. It represents any group selected from a heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, and an acyl group.
Y is an alkyl group having 3 or more carbon atoms, cycloalkyl group, alkenyl group, alkynyl group, aromatic hydrocarbon group, non-aromatic heterocyclic group, aromatic heterocyclic group, alkoxyl group, cycloalkoxyl group, aryloxy group, Alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkylsulfonyl group, arylsulfonyl group, NR ' R ^〃 (R ′ and R ^{各 々} each represent a hydrogen atom, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group), a nitro group, a cyano group, a hydroxyl group, an alkylsilyl group, an arylsilyl group Group, alkylphosphino group, arylphosphino group, al Ruhosuhoriru represents group, an aryl phosphoryl group, an alkyl thio phosphoryl group, one group selected from arylthio phosphoryl group.
R _{1 to} R ₇ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aromatic hydrocarbon group, non-aromatic heterocyclic group, aromatic heterocyclic group, halogen atom, alkoxyl group , Cycloalkoxyl group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkyl Sulfonyl, arylsulfonyl, amino, nitro, cyano, hydroxyl, alkylsilyl, arylsilyl, alkylphosphino, arylphosphino, alkylphosphoryl, arylphosphoryl, alkylthiophosphoryl, aryl It represents any group selected from the thiophosphoryl group. ] Wherein Y in the general formula (1) The organic electroluminescent device material according to claim 1, wherein the aromatic hydrocarbon group, a ^〃 aromatic heterocyclic group, or NR'R. 2. The organic electroluminescent element material according to claim 1, wherein Y in the general formula (1) is a group represented by the following general formula (2) or general formula (3).

[Wherein Y _{1 to} Y ₈ each represent C or N. R _{8 to} R ₁₅ each independently represent a group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{1 to} Y ₈ is N, they are bonded to the N atom. R _{8 to} R ₁₅ each represent an unshared electron pair. ]

[Wherein Y _{9 to} Y ₁₆ each represent C or N. R _{16 to} R ₂₃ each independently represents a group or a linking group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{9 to} Y ₁₆ is N, it is bonded to the N atom. R _{16 to} R ₂₃ each represent an unshared electron pair. R ^〃 'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, any of which is selected from acyl groups Represents a group. ]   X of the said General formula (1) is O or N-R, The organic electroluminescent element material of any one of Claims 1-3 characterized by the above-mentioned. At least one of R _{1 to} R _{7 in} the general formula (1) is a group represented by the following general formula (4) or general formula (5). The organic electroluminescent element material according to item.

[Wherein Y _{17 to} Y ₂₄ each represent C or N. R _{24 to} R ₃₁ each independently represent a group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{17 to} Y ₂₄ is N, they are bonded to the N atom. R _{24 to} R ₃₁ each represent an unshared electron pair. ]

[Wherein Y _{25 to} Y ₃₂ each represent C or N. R _{32 to} R ₃₉ each independently represent a group or a linking group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{25 to} Y ₃₂ is N, it is bonded to the N atom. R _{32 to} R ₃₉ each represent an unshared electron pair. R ^〃 'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, any of which is selected from acyl groups Represents a group. ] A compound represented by the following general formula (1):

[Wherein X represents O. Y represents a group of the following general formula (2) or general formula (3). R _{1 to} R ₇ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aromatic hydrocarbon group, non-aromatic heterocyclic group, aromatic heterocyclic group, halogen atom, alkoxyl group , Cycloalkoxyl group, aryloxy group, alkylthio group, cycloalkylthio group, arylthio group, alkoxycarbonyl group, aryloxycarbonyl group, sulfamoyl group, ureido group, acyl group, acyloxy group, amide group, carbamoyl group, sulfinyl group, alkyl Sulfonyl, arylsulfonyl, amino, nitro, cyano, hydroxyl, alkylsilyl, arylsilyl, alkylphosphino, arylphosphino, alkylphosphoryl, arylphosphoryl, alkylthiophosphoryl, aryl It represents any group selected from the thiophosphoryl group. ]

[Wherein Y _{1 to} Y ₈ each represent C or N. R _{8 to} R ₁₅ each independently represent a group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{1 to} Y ₈ is N, they are bonded to the N atom. R _{8 to} R ₁₅ each represent an unshared electron pair. ]

[Wherein Y _{9 to} Y ₁₆ each represent C or N. R _{16 to} R ₂₃ each independently represents a group or a linking group having the same meaning as R _{1 to} R ₇ in the general formula (1), and when any of Y _{9 to} Y ₁₆ is N, it is bonded to the N atom. R _{16 to} R ₂₃ each represent an unshared electron pair. R ^〃 'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, non-aromatic heterocyclic group, an aromatic heterocyclic group, an alkoxycarbonyl group, an aryloxycarbonyl group, any of which is selected from acyl groups Represents a group. ]   2. An organic electroluminescence device comprising an organic layer sandwiched between at least a pair of an anode and a cathode, wherein the organic layer comprises at least one layer including a light emitting layer, and at least one of the organic layers is claim 1. The organic electroluminescent element material containing the organic electroluminescent element material of any one of -5.   The said light emitting layer contains the organic electroluminescent element material of any one of Claims 1-5, The organic electroluminescent element of Claim 7 characterized by the above-mentioned.   8. The organic electroluminescence device according to claim 7, wherein the layer containing the organic electroluminescence device material is a hole transport layer.   The organic electroluminescent element according to claim 7, wherein the layer containing the organic electroluminescent element material is an electron transport layer.   The said electroluminescent layer contains a phosphorescence dopant, The organic electroluminescent element of any one of Claims 7-10 characterized by the above-mentioned.   The organic electroluminescence device according to claim 11, wherein the phosphorescent dopant is an Ir complex.   The organic electroluminescence device according to claim 7, wherein the organic electroluminescence device is manufactured by a wet process.   A display device comprising the organic electroluminescence element according to claim 7.   It has an organic electroluminescent element of any one of Claims 7-12, The illuminating device characterized by the above-mentioned.

Images