KR102034869B1 - Organic electroluminescent element, light-emitting device using organic electroluminescent element, display device using organic electroluminescent element, lighting device using organic electroluminescent element, and compound for organic electroluminescent element - Google Patents

Abstract

An organic electroluminescence having a substrate, a pair of electrodes disposed on the substrate and comprising an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer contains a phosphorescent material and a compound represented by the following formula: The device is excellent in durability and has a small difference in chromaticity during high temperature storage (X ¹⁰¹ represents an oxygen atom or a sulfur atom, and R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (except for an alkyl group and a cyano group). A plurality of R ¹⁰⁸ to R ¹¹⁰ may be the same as or different from each other (L ¹⁰¹ represents a single bond or an arylene group).

Description

Organic electroluminescent device, and light emitting device, display device, lighting device and compound for same device using the same device , AND COMPOUND FOR ORGANIC ELECTROLUMINESCENT ELEMENT}

The present invention relates to an organic electroluminescent device and a light emitting device, a display device, a lighting device and a compound for the device using the device.

Organic electroluminescent elements (hereinafter also referred to as "elements" and "organic EL elements") have been actively researched and developed in that high-luminescence emission is obtained by low voltage driving. An organic electroluminescent element has an organic layer between a pair of electrodes, and uses the energy of the excitons produced | generated by recombination of the electron injected from the cathode and the hole injected from the anode in an organic layer.

In recent years, the use of phosphorescent light emitting materials has increased the efficiency of organic electroluminescent devices. However, in practical use, improvement is required from the viewpoint of durability and the like. In order to improve the luminous efficiency of an additional element and the improvement of element durability, use of the dibenzothiophene type charge transport material is described in patent document 1. As shown in FIG. Moreover, patent document 2 has described the organic electroluminescent element using the compound which connected dibenzothiophene and triphenylene to the phenyl group. Moreover, the organic electroluminescent elements using the compound which connected dibenzothiophene to the phenyl group are described in patent documents 3 and 4.

On the other hand, in recent years, various display devices including organic electroluminescent elements have been widely used, and it is required to operate stably for a long time under various environments. For example, in the case of vehicle use for automobiles, the life expectancy is long (so-called durability), and the characteristics of the car do not change even after high temperature storage in that the vehicle becomes considerably high temperature during daily driving or parking. It is also required. In addition, it is important that the organic electroluminescent element does not change its characteristics after such high temperature storage in that it heats up at the time of driving at the same level or more as a conventional light emitting device.

International publication WO2007 / 069569 International publication WO2009 / 021126 International publication WO2009 / 085344 International publication WO2009 / 073245

On the other hand, the present inventors have studied the characteristics of the organic electroluminescent elements described in Patent Literatures 1 to 4, and as a result, in the conventional organic electroluminescent elements, there is still a problem in durability, and the chromaticity changes when stored at a high temperature. It turns out that there is.

Therefore, as a result of changing the compound used for an organic layer, it turned out that the difference in durability and chromaticity at the time of high temperature storage changes to some extent. Therefore, as a result of further studies on the compound used for the organic layer, it was found that even if the molecular weight of the compound used for the organic layer is simply increased, the durability and the color difference at the time of high temperature storage do not necessarily become good. For example, it was found that compound 9S described in Patent Literature 2 has a better chromaticity difference at high temperature storage than the compound 2S having a lower molecular weight and a glass transition temperature than the compound, but has poor durability. That is, it was found that by changing the compound used for the organic layer, it is difficult to improve the durability and chromaticity difference at the time of high temperature storage together.

The problem to be solved by the present invention is to provide an organic electroluminescent device which is excellent in durability and small in chromaticity difference during high temperature storage.

As a result of earnestly examining by the present inventors, by using the compound containing a dibenzothiophene structure or a dibenzofuran structure, and a p-terphenylene structure, it is excellent in durability, and the organic electroluminescence with little chromaticity difference at high temperature storage is obtained. The device was found to be provided.

That is, this invention can be achieved by the following means.

[1] A substrate, a pair of electrodes disposed on the substrate and including an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer is represented by a phosphorescent material and the following general formula (1) An organic electroluminescent device comprising a compound.

General formula (1)

[Formula 1]

(In General Formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (except for an alkyl group and a cyano group), and a plurality of R ¹⁰⁸ to R ^110. May be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group.)

[2] The organic electroluminescent device according to [1], wherein the compound represented by General Formula (1) has a molecular weight of 550 or more.

[3] a aryl group having 10 to 30 ring atoms in which at least one R ¹¹⁰ in General Formula (1) is a condensed ring, a heteroaryl group having 8 to 30 ring atoms as a condensed ring, and a carbon number having these as a substituent Characterized by being a monocyclic heteroaryl group having 5 to 25 ring atoms, having 6 to 25 aryl groups or heteroaryl groups having 5 to 25 ring atoms, or aryl groups having 6 to 25 carbon atoms as substituents [1] Or the organic electroluminescent device according to [2].

[4] The organic electroluminescent device according to any one of [1] to [3], wherein the compound represented by the general formula (1) is a compound represented by the following general formula (2) or (3).

General formula (2)

[Formula 2]

(In General Formula (2), X ²⁰¹ represents an oxygen atom or a sulfur atom. R ²⁰¹ to R ²¹² each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ²⁰⁸ and R ²⁰⁹ may be the same as each other. L ²⁰¹ represents a single bond or an arylene group, and is not a p-terphenylene group One of A ²⁰¹ and A ²⁰² is an aryl group having 10 to 30 ring atoms as the condensed ring and a ring atom as the condensed ring; A heteroaryl group having 8 to 30 carbon atoms, an aryl group having 6 to 25 carbon atoms having these as a substituent or a heteroaryl group having 5 to 25 ring atoms or a aryl group having 6 to 25 carbon atoms as a substituent, having 5 to 30 ring atoms 25 monocyclic heteroaryl groups, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.)

General formula (3)

[Formula 3]

(In General Formula (3), X ³⁰¹ represents an oxygen atom or a sulfur atom. R ³⁰¹ to R ³¹⁵ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ³⁰⁸ to R ³¹² may be the same as each other. L ³⁰¹ represents a single bond or an arylene group One of A ³⁰¹ and A ³⁰² is an aryl group having 10 to 30 ring atoms as a condensed ring or a heteroaryl group having 8 to 30 ring atoms as a condensed ring; And a C6-C25 aryl group having 5 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms, or a C6-C25 monocyclic aryl group having a substituent as a substituent. And the other represents a hydrogen atom, an aryl group, or a heteroaryl group.)

[5] The organic electroluminescent device according to any one of [1] to [4], wherein both R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1) are hydrogen atoms.

[6] The organic electroluminescent device according to any one of [1] to [5], wherein the compound represented by General Formula (1) is a compound having a glass transition temperature of 100 ° C or higher.

[7] The organic electroluminescent device according to any one of [1] to [6], wherein the compound represented by General Formula (1) is a compound represented by any of the following General Formulas (4) to (7).

[Formula 4]

(In General Formula (4), X ⁴⁰¹ and X ⁴⁰² each independently represent an oxygen atom or a sulfur atom. R ⁴⁰¹ to R ⁴¹⁷ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁴⁰⁸ ˜. R ⁴¹⁰ may be the same as or different from each other, n ₄₀₁ represents 0 or 1)

[Formula 5]

(In General Formula (5), X ⁵⁰¹ represents an oxygen atom or a sulfur atom. R ⁵⁰¹ to R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁵⁰⁸ to R ⁵¹³ may be the same as each other. and or different. n ₅₀₁ represents 0 or 1.)

[Formula 6]

(In General Formula (6), X ⁶⁰¹ and X ⁶⁰² each independently represent an oxygen atom or a sulfur atom. R ⁶⁰¹ to R ⁶²¹ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same as or different from each other.)

[Formula 7]

(In General Formula (7), X ⁷⁰¹ represents an oxygen atom or a sulfur atom. R ⁷⁰¹ to R ⁷¹⁶ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁷⁰⁸ to R ⁷¹⁶ may be the same as each other. May be different.)

[8] The organic electroluminescent device according to any one of [1] to [7], wherein the phosphorescent material is an iridium (Ir) complex represented by the following General Formula (E-1).

[Formula 8]

(The following formula (E-1) of, Z ¹ and Z ² is a group of atoms for forming a heterocyclic ring of 5 or 6 atoms with each independently represent a carbon atom or a nitrogen atom. A ₁ is Z ¹ and the nitrogen atom B ₁ represents an atomic group forming a 5 or 6 membered ring together with Z ² and a carbon atom (XY) represents a monoanionic bidentate ligand, n _E1 represents an integer of 1 to 3. )

[9] The organic electroluminescent device according to [8], wherein the iridium (Ir) complex represented by General Formula (E-1) is represented by the following General Formula (E-2).

[Formula 9]

(In the general formula ^{(E-2), A E1} ~ A E8 represent a substituted carbon atom by a nitrogen atom, or R ^E are each independently. R ^E represents a hydrogen atom or a substituent. (XY) is a mono anionic 2 shows a left ligand. _E2 n represents an integer of 1 to 3.)

[10] The organic layer has a light emitting layer containing the phosphorescent light emitting material and another organic layer, and the light emitting layer contains a compound represented by the general formula (1), any one of [1] to [9] The organic electroluminescent element of Claim.

[11] The organic layer has a light emitting layer containing the phosphorescent light emitting material and another organic layer, and another organic layer is disposed between the light emitting layer and the cathode, is adjacent to the light emitting layer, and is represented by the general formula (1). The organic electroluminescent element as described in any one of [1]-[10] containing the compound shown.

[12] The electron transport layer adjacent to the cathode is optionally provided between the pair of electrodes, and the hole transport layer adjacent to the opposite side of the cathode of the electron transport layer optionally has the electron transport layer or the hole block layer. The organic electroluminescent element as described in any one of [1]-[11] containing the compound represented by Formula (1).

[13] The organic layer disposed between the pair of electrodes includes a layer formed by deposition of a composition containing at least one compound represented by the general formula (1). [1] to [12 The organic electroluminescent element in any one of].

[14] The organic electroluminescent device according to any one of [1] to [13], wherein the peak emission wavelength is 490 to 580 nm.

[15] A light emitting device, lighting device or display device comprising the organic electroluminescent element according to any one of [1] to [14].

[16] A compound represented by any of the following General Formulas (8) to (11).

[Formula 10]

(In General Formulas (8) to (11), X ⁸⁰¹ to X ⁸⁰⁶ each independently represent an oxygen atom or a sulfur atom, and R ⁸⁰¹ to R ⁸⁰⁶ each independently represent a hydrogen atom or an aryl group having 6 to 13 carbon atoms. A ¹¹ to A ¹³ each independently represent CH or a nitrogen atom, and at least one is a nitrogen atom.)

According to the present invention, it is possible to provide an organic electroluminescent device which is excellent in durability and small in chromaticity difference during high temperature storage.

Moreover, according to this invention, the compound useful for an organic electroluminescent element can be provided as a charge transport material, a host material of a light emitting layer, etc., and also the light emitting device, display apparatus, and illumination device using this organic electroluminescent element can be provided. have.

BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic diagram which shows an example of a structure of the organic electroluminescent element which concerns on this invention.
2 is a schematic view showing an example of a light emitting device according to the present invention.
3 is a schematic view showing an example of a lighting apparatus according to the present invention.
4 is a ¹ H-NMR spectrum diagram of Compound 1B-2 of the present invention.
5 is a ¹ H-NMR spectrum diagram of Compound 1B-3 of the present invention.
6 is a ¹ H-NMR spectrum diagram of Compound 1B-4 of the present invention.
7 is a ¹ H-NMR spectrum diagram of Compound 1B-17 of the present invention.
8 is a ¹ H-NMR spectrum of the compound 1D-1 of the present invention.
9 is a ¹ H-NMR spectrum diagram of Compound 1D-3 of the present invention.

EMBODIMENT OF THE INVENTION Below, the content of this invention is demonstrated in detail. Although description of the element | module described below may be made | formed based on typical embodiment of this invention, this invention is not limited to such embodiment. In addition, it is used by the meaning which includes with "-" the numerical value described before and after that as a lower limit and an upper limit in this specification.

[Organic EL device]

The organic electroluminescent device of the present invention has a substrate, a pair of electrodes disposed on the substrate, including an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer is a phosphorescent material and the following general material. It is characterized by containing the compound represented by Formula (1).

General formula (1)

[Formula 11]

(In General Formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (except for an alkyl group and a cyano group), and a plurality of R ¹⁰⁸ to R ^110. May be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group.

In an organic electroluminescent element, electrons are injected from a cathode, holes are injected from an anode, and they recombine in an organic layer (functionally sometimes called a light emitting layer) as they move on an organic molecule. The light emitting material emits light using the excitation energy generated at that time. Therefore, when considering the lifetime (durability) of the organic EL device, the stability of the material is important. In particular, because the charge (electrons or holes) move through the material phase, stability to the charge of the material (= stability in the radical state) is very important. Although not bound by any theory, it has been found in the present invention that the spin density distribution in the radical state can be delocalized more widely than other phenyl groups or biphenyl groups by using a compound having a p-terphenyl structure. Here, as the spin density distribution is diffused, the radical species are thermodynamically stabilized. For this reason, it is thought that the dibenzothiophene or dibenzofuran derivative which has a p-terphenyl structure can ensure high stability in a radical state. As a result, it is thought that the durability of the organic electroluminescent element could be significantly improved. In addition, since the compound which introduce | transduced p-terphenyl structure has less movable site | parts than the case of m-terphenyl structure, for example, and can change the film | membrane quality change of an organic layer at high temperature, it is the high temperature of an organic electroluminescent element. It is thought that the color and the difference after storage were made small, too.

The structure of the organic electroluminescent element of the present invention is not particularly limited. An example of a structure of the organic electroluminescent element of this invention is shown in FIG. The organic electroluminescent element 10 of FIG. 1 has an organic layer on the board | substrate 2 between a pair of electrodes (anode 3 and cathode 9).

The element structure of the organic electroluminescent element, the board | substrate, a cathode, and an anode are described in detail in Unexamined-Japanese-Patent No. 2008-270736, for example, and the matter of the publication can be applied to this invention.

Hereinafter, the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board | substrate, an electrode, an organic layer, a protective layer, a sealing container, a drive method, a light emission wavelength, and a use.

<Substrate>

The organic electroluminescent device of the present invention has a substrate.

It is preferable that it is a board | substrate which does not scatter or attenuate the light emitted from an organic layer as a board | substrate used by this invention. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

<Electrode>

The organic electroluminescent element of this invention is arrange | positioned on the said board | substrate, and has a pair of electrode containing an anode and a cathode.

It is preferable that at least one of the anode and the cathode which are a pair of electrodes is transparent or translucent on the property of a light emitting element.

(anode)

The anode usually has a function as an electrode for supplying holes to the organic layer, and the shape, structure, size, and the like thereof are not particularly limited, and may be appropriately selected from known electrode materials depending on the use and purpose of the light emitting device. As mentioned above, the anode is usually formed as a transparent anode.

(cathode)

The cathode may have a function as an electrode which injects electrons into an organic layer normally, and there is no restriction | limiting in particular about the shape, structure, size, etc., According to the use and the objective of a light emitting element, it can select suitably from well-known electrode materials.

<Organic layer>

The organic electroluminescent element of this invention has an organic layer arrange | positioned between the said electrodes, The said organic layer contains a phosphorescence emitting material and the compound represented by the said General formula (1), It is characterized by the above-mentioned.

Although the said organic layer does not have a restriction | limiting in particular, Although it can select suitably according to the use and the objective of an organic electroluminescent element, it is preferable to form on the said transparent electrode or on the said semi-transparent electrode. In this case, the organic layer is formed on the entire surface or one surface on the transparent electrode or the translucent electrode.

There is no restriction | limiting in particular about the shape, size, thickness, etc. of an organic layer, According to the objective, it can select suitably.

Hereinafter, the structure of the organic layer in the organic electroluminescent element of this invention, the formation method of an organic layer, the preferable aspect of each layer which comprises an organic layer, and the material used for each layer are demonstrated in order.

(Configuration of Organic Layer)

In the organic electroluminescent element of this invention, it is preferable that the said organic layer contains a charge transport layer. The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent device. Specifically, a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, or an electron injection layer is mentioned. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer or a light emitting layer, it is possible to manufacture an organic electroluminescent device with low cost and high efficiency.

In the organic electroluminescent element of this invention, it is preferable to have a light emitting layer containing the said phosphorescence emitting material, and another organic layer, and the said light emitting layer contains the compound represented by the said General formula (1). Moreover, in the organic electroluminescent element of this invention, it is more preferable that the said organic layer has a light emitting layer and the other organic layer containing the said phosphorescence emitting material. However, in the organic electroluminescent element of this invention, even if the said organic layer has a light emitting layer and another organic layer, it does not necessarily need to distinguish between layers clearly.

The organic electroluminescent element of this invention contains the compound in which the said organic layer is represented by the phosphorescence emitting material and the said General formula (1). At this time, there is no restriction | limiting in particular in the place where the said phosphorescence emitting material and the compound represented by the said General formula (1) are contained. In this invention, it is more preferable that the said organic layer has the light emitting layer and the other organic layer containing the said phosphorescence emitting material, and the said light emitting layer contains the compound represented by the said General formula (1). At this time, it is preferable that the compound represented by the said General formula (1) is used as a host compound of a light emitting layer.

The electron transport layer adjacent to the cathode is optionally provided between the pair of electrodes, and the hole transport layer adjacent to the opposite side of the cathode of the electron transport layer is optionally provided, and the electron transport layer or the hole block layer is the general formula. It is also preferable to contain the compound represented by (1).

Two or more layers of these organic layers may be formed, respectively, and when forming two or more layers, they may be formed with the same material and may be formed with a different material for every layer.

(Formation method of organic layer)

In the organic electroluminescent device of the present invention, each organic layer may be formed by any of a wet film forming method (solution coating method) such as a dry film forming method such as a vapor deposition method or a sputtering method, a transfer method, a printing method, a spin coating method, a bar coating method, or the like. It can form preferably.

It is preferable that the organic electroluminescent element of this invention contains the layer formed by vapor deposition of the composition in which the organic layer arrange | positioned between the said pair of electrodes contains the compound represented by the said General formula (1) of at least 1 layer.

(Light emitting layer)

The light emitting layer has a function of receiving holes from an anode, a hole injection layer, or a hole transport layer upon application of an electric field, receiving electrons from a cathode, an electron injection layer or an electron transport layer, and providing a place for recombination of holes and electrons to emit light. It is a layer having. However, the said light emitting layer in this invention is not necessarily limited to light emission by such a mechanism. It is preferable that the light emitting layer in the organic electroluminescent element of this invention contains at least 1 sort (s) of said phosphorescence emitting material.

The said light emitting layer in the organic electroluminescent element of this invention may be comprised only by the said phosphorescence emitting material, and the structure made into the mixed layer of a host material and the said phosphorescence emitting material may be sufficient. The kind of the phosphorescent light emitting material may be one kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one type or two or more types, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. In addition, the light emitting layer does not have charge transport properties and may contain a material that does not emit light.

The light emitting layer may be one layer or a multilayer of two or more layers, each layer may contain the same light emitting material or host material, and may contain different materials for each layer. When there are multiple light emitting layers, each light emitting layer may emit light of a different light emission color.

Although the thickness of a light emitting layer is not specifically limited, Usually, it is preferable that it is 2 nm-500 nm, Especially, from a viewpoint of an external quantum efficiency, it is more preferable that it is 3 nm-200 nm, It is 5 nm-100 nm More preferred.

In the organic electroluminescent device of the present invention, it is preferable that the light emitting layer contains a compound represented by the general formula (1), and it is more preferable to use a compound represented by the general formula (1) as a host material of the light emitting layer. It is an aspect. Here, in this specification, a host material is a compound mainly responsible for injection and transport of an electric charge in a light emitting layer, and itself is a compound which does not emit light substantially. The term "not substantially emitting light" herein means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less of the total amount of light emitted from the entire device, more preferably 3% or less, and still more preferably 1 It means that it is% or less.

Hereinafter, as a material of the said light emitting layer, other host materials other than the compound represented by the said General formula (1), the said phosphorescence emitting material, and the compound represented by the said General formula (1) are demonstrated in order. In addition, the compound represented by the said General formula (1) may be used other than the said light emitting layer in the organic electroluminescent element of this invention.

(1) The compound represented by the said General formula (1)

Hereinafter, the compound represented by following General formula (1) is demonstrated.

General formula (1)

[Formula 12]

(In General Formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (except for an alkyl group and a cyano group), and a plurality of R ¹⁰⁸ to R ^110. May be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group.)

In addition, in this invention, the hydrogen atom in description of the said General formula (1) also contains an isotope (deuterium atom etc.), and also shows that the atom which comprises a substituent also contains the isotope.

When referring to "substituent" in the present invention, the substituent may be substituted. For example, in the present invention, the term "alkyl group" includes an alkyl group substituted with a fluorine atom (e.g., a trifluoromethyl group), an alkyl group substituted with an aryl group (e.g., a triphenylmethyl group), and the like. 1-6 alkyl group ", it shows the C1-C6 as all the groups including what was substituted.

In said general formula (1), X <^101> represents an oxygen atom or a sulfur atom. Sulfur atoms having a larger van der Waals radius are preferred from the viewpoint of improving electron mobility.

In said general formula (1), as a substituent represented by R <^101> -R <^{110>, it} is a substituent except an alkyl group and a cyano group, respectively, The following substituent group A can be mentioned independently, The substituent may further have a substituent. . As said additional substituent, group chosen from the said substituent group A is mentioned.

《Substituent Group A》

Alkenyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc. are mentioned. Alkynyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, a propargyl, 3-pentynyl, etc. are mentioned). And an aryl group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C14, For example, phenyl, p-methylphenyl, naphthyl, anthryl etc. are mentioned. ), An amino group (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, for example, amino, methylamino, dimethylamino, diethylamino, dibenzylamino, Diphenylamino, ditolylamino, etc.); Coxyl (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C10, For example, methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc. Aryloxy group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12, For example, phenyloxy, 1-naphthyloxy, 2- Naphthyloxy, etc.), heterocyclic oxy group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, pyridyloxy, pyra Genyloxy, pyrimidinyloxy, quinolyloxy, etc.), an acyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C12, For example, Acetyl, benzoyl, formyl, pivaloyl, etc.); Alkoxycarbonyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C12, For example, methoxycarbonyl, ethoxycarbonyl, etc. are mentioned), Aryl An oxycarbonyl group (preferably C7-30, More preferably, it is C7-20, Especially preferably, it is C7-12, For example, phenyloxycarbonyl etc. are mentioned), Acyloxy group (Preferably Is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, acetoxy, benzoyloxy, etc. are mentioned, Acylamino group (Preferably C2-C30) More preferably, they are C2-C20, Especially preferably, it is C2-C10, For example, acetylamino, benzoylamino, etc. are mentioned, The alkoxycarbonylamino group (Preferably C2-C2) -30, More preferably, it is C2-C20, Especially preferably, it is C2-C12, For example, a methoxycarbonylamino etc. are mentioned, An aryloxycarbonylamino group (Preferably C7-C30) More preferably, they are C7-20, Especially preferably, it is C7-12, For example, a phenyloxycarbonylamino etc. are mentioned, A sulfonylamino group (Preferably C1-C30, More preferably, Is C1-C20, Especially preferably, it is C1-C12, For example, methanesulfonylamino, benzenesulfonylamino, etc. are mentioned, A sulfamoyl group (preferably C0-C30, More preferably, Is 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, and examples thereof include sulfamoyl, methyl sulfamoyl, dimethyl sulfamoyl, and phenyl sulfamoyl; and carbamoyl groups (preferably having 1 to 20 carbon atoms). 3 0, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc. are mentioned), Alkylthio group (preferably C1-C30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, methylthio, ethylthio, etc. are mentioned), An arylthio group ( Preferably it is C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12, For example, a phenylthio etc. are mentioned, Heterocyclic thio group (Preferably C1-C1) 30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, pyridylthio, 2-benzimizolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc. The sulfonyl group (preferably carbon number) 1-30, More preferably, it is C1-C20, Especially preferably, it is C1-C12, For example, mesyl, tosyl, etc. are mentioned, A sulfinyl group (preferably C1-C30, More preferably Is C1-C20, Especially preferably, it is C1-C12, For example, methanesulfinyl, benzenesulfinyl, etc. are mentioned, A ureido group (preferably C1-C30, More preferably, it is C1-C1) 20, Especially preferably, it is C1-C12, For example, ureido, methylureido, phenylureido, etc. are mentioned, The phosphate amide group (preferably C1-C30, More preferably, it is carbon number) 1-20, Especially preferably, it is C1-C12, For example, diethyl phosphate amide, phenyl phosphate amide, etc. are mentioned, A hydroxyl group, a mercapto group, a halogen atom (For example, a fluorine atom, a chlorine) Atom, bromine atom, iodine Atom), a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a heterocyclic group (including a heteroaryl group, preferably 1 to 30 carbon atoms, more preferably carbon atoms 1-12, and a hetero atom is a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, a tellurium atom, specifically, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl , Pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperi Dino, morpholino, pyrrolidyl, pyrrolidino, benzooxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like), silyl group (preferably Is C3-C40, More preferably, it is C3-C30, Especially preferably, it is C3-C24, for example, trimethylsilyl, a triphenylsilyl, etc. are mentioned, a silyloxy group (preferably C3-C40, More preferably, it is C3-C30, Especially preferably, Is C3-C24, for example, trimethylsilyloxy, a triphenylsilyloxy, etc. are mentioned, a phosphoryl group (For example, a diphenylphosphoryl group, a dimethylphosphoryl group, etc. are mentioned). Can be. These substituents may further be substituted and group selected from the substituent group A demonstrated above as further substituent is mentioned.

As the R ¹⁰¹ ~ R ¹¹⁰ are each independently preferably a hydrogen atom, an aryl group or a heteroaryl group.

The aryl group represented by R ¹⁰¹ to R ¹¹⁰ is preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, for example, a phenyl group, xylyl group, biphenyl group, or terphenyl group. , Naphthyl group, anthryl group, triphenylenyl group and the like.

The heteroaryl group represented by R ¹⁰¹ to R ¹¹⁰ is preferably 5 to 30 ring atoms, more preferably 5 to 20 ring atoms, particularly preferably 5 to 15 ring atoms, for example, a pyridyl group, A pyrimidinyl group, a triazinyl group, a pyrazinyl group, a pyridazinyl group, a carbazolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, etc. are mentioned.

R ¹⁰¹ to R ¹⁰⁷ are more preferably each independently a hydrogen atom or an aryl group having 6 to 18 carbon atoms, particularly preferably a hydrogen atom or a phenyl group, and still more preferably a hydrogen atom. However, R ¹⁰¹ ~ R 1 is a phenyl group or aspect of a plurality of ¹⁰⁷ degree and more preferably also aspects of what is 1 or 2 phenyl groups.

As R ¹⁰⁸ and R ¹⁰⁹ , a hydrogen atom, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group is preferable. In the organic electroluminescent device of the present invention, both R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1) are hydrogen atoms. It is more preferable that is.

As a substituent in the case where R ¹⁰⁸ and R ¹⁰⁹ have additional substituents, a substituted or unsubstituted aryl group or heteroaryl group is preferable, and a phenyl group is preferable.

As said R <^110> , at least 1 R <^110> is an aryl group of 10-30 ring atoms which are condensed rings, a heteroaryl group of 8-30 ring atoms which is a condensed ring, and a C6-C25 aryl group which has these as a substituent Or a heteroaryl group having 5 to 25 ring atoms or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, and a monocyclic heteroaryl group having 5 to 25 ring atoms, and other R ¹¹⁰ is a hydrogen atom or 6 to 25 carbon atoms. It is preferable that it is a aryl group of 30 or a heteroaryl group having 5 to 25 ring atoms.

As the R ^110, at least one R ¹¹⁰ is a condensed ring of the aryl group of ring atoms 12 to 18, fused heteroaryl group ring a number 9-13 ring atoms, or those of carbon number 6 to 18 having as a substituent an aryl group Or a heteroaryl group having 6 to 13 ring atoms or a monocyclic aryl group having 6 to 18 carbon atoms as a substituent, and a monocyclic heteroaryl group having 6 to 13 ring atoms, and more preferably, R ¹¹⁰ is a hydrogen atom; Do. Moreover, the heterocyclic group of 6-13 ring atoms which has the said C6-C18 monocyclic aryl group as a substituent is the heterocyclic ring of 6-10 ring atoms which has a C6-C10 monocyclic aryl group as a substituent It is preferable that it is an aryl group, and the preferable number of the C6-C10 monocyclic aryl group is 1 or 2.

An aryl group having 10 to 30 ring atoms as the condensed ring, an aryl group having 6 to 25 ring atoms as the substituent, and an aryl group having 6 to 25 carbon atoms as having a substituent The position of the substituent of R ¹¹⁰ which is a heteroaryl group having 5 to 20 ring atoms having a heteroaryl group having 6 to 13 atoms or a aryl group having 6 to 20 carbon atoms as a substituent is a benzene ring substituted by R ^110. The substituent forming the p-terphenylene skeleton of may be any of ortho-position, meta-position, or para-position, and among these, meta-position or para-position suppresses the adsorption reaction between the R ¹¹⁰ and other substituents. It is preferable from the viewpoint of the point of view or the element drive voltage reduction. Moreover, when the emission color from an organic electroluminescent element is green (luminescence peak wavelength is 490-580 nm), it is more preferable that it is a meta position from a viewpoint of luminous efficiency.

L ¹⁰¹ represents a single bond or an arylene group. The arylene group may be a condensed ring (e.g., naphthyl group, anthryl group, etc.), but in the case where the emission color from the organic electroluminescent element is green (emission peak wavelength is 490 to 580 nm) from the viewpoint of luminous efficiency It is preferable that it is an arylene group which does not have a condensed ring, and it is more preferable that it has the structure formed by the phenylene group which may have a substituent, or its plurality connected by single bond. As an arylene group which said L <^101> represents, a phenylene group, a biphenylene group, a terphenylene group, etc. are mentioned preferably. Moreover, these connection patterns are not specifically limited.

L ¹⁰¹ is preferably a single bond, a phenylene group, a biphenylene group or a terphenylene group, and a single bond or a terphenylene group (among these, a p-terphenylene group or an m-terphenylene group is preferable, and p-terphenylene is preferred. Group is more preferable, an unsubstituted p-terphenylene group is especially preferable), and a single bond is more preferable.

In addition, in this invention, p-terphenylene and m-terphenylene show the following structures, respectively (* represents a bond).

[Formula 13]

L ²⁰¹ is preferably unsubstituted, but may optionally have a substituent. Substituent group A is mentioned as a substituent in the case where ^L201 has an additional substituent, A substituted or unsubstituted aryl group (phenyl group or biphenyl group) is preferable, and a phenyl group is preferable.

In the organic electroluminescent element of this invention, it is preferable that the compound represented by the said General formula (1) is a compound represented by following General formula (2) or (3).

General formula (2)

[Formula 14]

In General Formula (2), X ²⁰¹ represents an oxygen atom or a sulfur atom. R ²⁰¹ to R ²¹² each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ²⁰⁸ and R ²⁰⁹ may be the same as or different from each other. L ²⁰¹ represents a single bond or an arylene group, and is not a p-terphenylene group. One of A ²⁰¹ and A ²⁰² is an aryl group having 10 to 30 ring atoms as a condensed ring, a heteroaryl group having 8 to 30 ring atoms as a condensed ring, an aryl group having 6 to 25 carbon atoms or having a ring atom as a substituent The heteroaryl group of 5-25 monocyclic ring which has a heteroaryl group of 5-25 or a C6-C25 cyclic group as a substituent is shown, The other one shows a hydrogen atom, an aryl group, or heteroaryl group.

A preferred range of ²⁰¹ X in the general formula (2) is the same as the preferred range of ¹⁰¹ X in the general formula (1).

The preferable range of R ²⁰¹ to R ²⁰⁹ in General Formula (2) is the same as the preferred range of R ¹⁰¹ to R ¹⁰⁹ in General Formula (1).

Wherein in the formula (2) R ²¹⁰ ~ R ²¹² is preferably hydrogen atom or an aryl group having from 6 to 20 carbon atoms, more preferably a hydrogen atom.

An aryl group having 10 to 30 ring atoms which is a condensed ring represented by one of A ²⁰¹ and A ²⁰² in General Formula (2), a heteroaryl group having 8 to 30 ring atoms that is a condensed ring, and having carbon as a substituent The preferable range of the monocyclic heteroaryl group having 5 to 25 ring atoms having a 6 to 25 aryl group or a heteroaryl group having 5 to 25 ring atoms or a aryl group having 6 to 25 carbon atoms as a substituent is a dibenzo. A thiophenyl group, a dibenzofuranyl group, a triphenylenyl group, a carbazolyl group, a C6-C25 aryl group or a C5-C25 heteroaryl group which has these substituents, or a C6-C13 monocyclic aryl It is a monocyclic heteroaryl group of 5-25 ring atoms which has a group as a substituent. Especially, it is more preferable that it is a dibenzothiophenyl group, a dibenzofuranyl group, a triphenylenyl group, or a phenylene group which has these substituents, It is especially preferable that it is a dibenzothiophenyl group, a dibenzofuranyl group, or a triphenylenyl group, The benzothiophenyl group or the triphenylenyl group is more particularly preferable, and the triphenylenyl group is more preferable. Moreover, these condensed rings may use the said skeleton as a basic skeleton, and may further condensate substituents.

The other one of A ²⁰¹ and A ²⁰² in General Formula (2) is preferably a hydrogen atom or an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms, and more preferably a hydrogen atom. Do.

Wherein in the formula (2) L ²⁰¹ is, represents a single bond or an arylene, and not group p- terphenyl alkylene.

When groups arylene wherein L ²⁰¹ represents, but even condensed rings (e.g. naphthyl group, an anthryl group, etc.), a luminescent color from an organic EL device of green (emission peak wavelength of 490 ~ 580 ㎚), the light emitting It is preferable that it is an arylene group which does not have a condensed ring from a viewpoint of efficiency, It is more preferable that it is a phenylene group, a biphenylene group, and m-terphenylene group, It is a 1, 3- phenylene group or a 3,5'- biphenylene group Is particularly preferred.

It is preferable that L ²⁰¹ in the said General formula (2) is a single bond.

General formula (3)

[Formula 15]

In General Formula (3), X ³⁰¹ represents an oxygen atom or a sulfur atom. R ³⁰¹ to R ³¹⁵ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ³⁰⁸ to R ³¹² may be the same as or different from each other. L ³⁰¹ represents a single bond or an arylene group. One of A ³⁰¹ and A ³⁰² is an aryl group having 10 to 30 ring atoms as a condensed ring, a heteroaryl group having 8 to 30 ring atoms as a condensed ring, an aryl group having 6 to 25 carbon atoms or having a ring atom as a substituent The heteroaryl group of 5-25 monocyclic ring which has a 5-25 heteroaryl group or a C6-C25 monocyclic aryl group as a substituent is shown, and the other shows a hydrogen atom, an aryl group, or a heteroaryl group.

A preferred range of ³⁰¹ X in the general formula (3) is the same as the preferred range of ¹⁰¹ X in the general formula (1).

The preferable ranges of R ³⁰¹ to R ³¹² in General Formula (3) are the same as those of R ¹⁰¹ to R ¹⁰⁹ in General Formula (1).

The preferable range of R ³¹³ to R ³¹⁵ in General Formula (3) is the same as the preferable range of R ²¹⁰ to R ²¹² in General Formula (2).

Preferable ranges of A ³⁰¹ and A ³⁰² in the general formula (3) are the same as those of A ²⁰¹ and A ²⁰² in the general formula (2).

The condensed ring (for example, naphthyl group, anthryl group, etc.) may be sufficient as the arylene group which L ³⁰¹ in the said General formula (3) represents, but the light emission color from an organic electroluminescent element is green (emission peak wavelength is 490- 580 nm), it is preferable that it is an arylene group which does not have a condensed ring from a viewpoint of luminous efficiency, It is more preferable that it is a phenylene group, a biphenylene group, m-terphenylene group, A 1, 3- phenylene group or 3 It is especially preferable that it is a 5 'biphenylene group.

It is preferable that L ³⁰¹ in the said General formula (3) is a single bond.

As for the organic electroluminescent element of this invention, it is especially preferable that the compound represented by the said General formula (1) is a compound represented by either of following General formula (4)-(7) and General formula (11) mentioned later, The said general It is more preferable that the compound represented by Formula (1) is a compound represented by any of the following general formulas (4)-(7).

[Formula 16]

In General Formula (4), X ⁴⁰¹ and X ⁴⁰² each independently represent an oxygen atom or a sulfur atom. R ⁴⁰¹ to R ⁴¹⁷ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁴⁰⁸ to R ⁴¹⁰ may be the same as or different from each other. n ₄₀₁ represents 0 or 1.

A preferred range of X ⁴⁰¹ and X ⁴⁰² In the above formula (4) is the same as the preferred range of ¹⁰¹ X in the general formula (1).

The preferable ranges of R ⁴⁰¹ to R ⁴⁰⁷ and R ⁴¹¹ to R ⁴¹⁷ in the general formula (4) are the same as the preferred ranges of R ¹⁰¹ to R ¹⁰⁷ in the general formula (1).

The preferable range of R ⁴⁰⁸ to R ⁴¹⁰ in the general formula (4) is the same as the preferred range of R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1).

It is preferable that _n401 in the said General formula (4) is zero.

[Formula 17]

In General Formula (5), X ⁵⁰¹ represents an oxygen atom or a sulfur atom. R ⁵⁰¹ to R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁵⁰⁸ to R ⁵¹³ may be the same as or different from each other. n ₅₀₁ represents 0 or 1.

The preferable range of X ⁵⁰¹ in the general formula (5) is the same as the preferred range of X ¹⁰¹ in the general formula (1).

The preferable range of R ⁵⁰¹ to R ⁵⁰⁷ in the general formula (5) is the same as the preferred range of R ¹⁰¹ to R ¹⁰⁷ in the general formula (1).

The preferable ranges of R ⁵⁰⁸ to R ⁵¹⁰ in General Formula (5) are the same as the preferred ranges of R ¹⁰⁸ and R ¹⁰⁹ in General Formula (1).

In General Formula (5), R ⁵¹¹ to R ⁵¹³ are preferably a hydrogen atom, an aryl group having 6 to 25 carbon atoms, or a heteroaryl group having 5 to 25 ring atoms, and more preferably a hydrogen atom.

In the general formula (5), n ₅₀₁ is preferably 0.

[Formula 18]

In General Formula (6), X ⁶⁰¹ and X ⁶⁰² each independently represent an oxygen atom or a sulfur atom. R ⁶⁰¹ to R ⁶²¹ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same as or different from each other.

A preferred range of X ⁶⁰¹ and X ⁶⁰² In the above formula (6) is the same as the preferred range of ¹⁰¹ X in the general formula (1).

The preferable ranges of R ⁶⁰¹ to R ⁶⁰⁷ and R ⁶¹⁴ to R ⁶²⁰ in General Formula (6) are the same as the preferred ranges of R ¹⁰¹ to R ¹⁰⁷ in General Formula (1).

The preferable ranges of R ⁶⁰⁸ to R ⁶¹³ in General Formula (6) are the same as the preferred ranges of R ¹⁰⁸ and R ¹⁰⁹ in General Formula (1).

[Formula 19]

In General Formula (7), X ⁷⁰¹ represents an oxygen atom or a sulfur atom. R ⁷⁰¹ to R ⁷¹⁶ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁷⁰⁸ to R ⁷¹⁶ may be the same as or different from each other.

A preferred range of ⁷⁰¹ X in the general formula (7) is the same as the preferred range of ¹⁰¹ X in the general formula (1).

The preferable range of R ⁷⁰¹ to R ⁷⁰⁷ in the general formula (7) is the same as the preferred range of R ¹⁰¹ to R ¹⁰⁷ in the general formula (1).

The preferable range of R ⁷⁰⁸ to R ⁷¹³ in the general formula (7) is the same as the preferred range of R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1).

The preferable range of R ⁷¹⁴ to R ⁷¹⁶ in the general formula (7) is the same as the preferred range of R ⁵¹¹ to R ⁵¹³ in the general formula (5).

<< The compound of this invention-Especially preferable aspect- of the compound represented by the said General formula (1) >>

Among the compounds represented by the general formula (1), compounds represented by any of the following general formulas (8) to (11) are particularly preferable in the present invention. Compounds of the present invention represented by any of the following general formulas (8) to (11) include organic electronic devices such as electrophotographic, organic transistors, organic photoelectric conversion devices (energy conversion applications, sensor applications, and the like) and organic electroluminescent devices. It can use preferably, and it is especially preferable to use for organic electroluminescent elements.

[Formula 20]

In General Formulas (8) to (11), X ⁸⁰¹ to X ⁸⁰⁶ each independently represent an oxygen atom or a sulfur atom, and R ⁸⁰¹ to R ⁸⁰⁶ each independently represent a hydrogen atom or an aryl group having 6 to 13 carbon atoms. A ¹¹ to A ¹³ each independently represent CH or a nitrogen atom, and at least one is a nitrogen atom.

A preferred range of the above formulas (8) ~ (11), ⁸⁰¹ X ⁸⁰⁶ X ~ is the same as the preferred range of ¹⁰¹ X in said formula (1).

In the general formulas (8) to (11), each of R ⁸⁰¹ to R ⁸⁰⁶ is preferably a hydrogen atom or a phenyl group, and more preferably a hydrogen atom.

In said general formula (11), A <^11> -A <^13> respectively independently represents CH or a nitrogen atom, and at least 1 is a nitrogen atom. When there is one nitrogen atom contained in A ¹¹ to A ¹³ , it is preferable that A ¹¹ or A ¹² is a nitrogen atom. A ¹¹ ~ ¹³ A when 2 nitrogen atoms are contained in the individual, A ¹² and A ¹³ are preferably a nitrogen atom.

The formula compounds represented by 11, A ¹¹ ~ A ¹³ nitrogen atoms 1 to be contained in the numbered A ¹¹ or A ¹² is either a nitrogen atom, A ¹¹ ~ A ¹³ nitrogen atoms 2 numbered, A ¹² and A ¹³ which is contained in As for this nitrogen atom, it is more preferable that A <^11> -A <^13> are all nitrogen atoms. In addition, among them, A ¹¹ ~ A ¹³ is particularly preferred nitrogen atom 2 numbered, A ¹² and A ¹³ is a nitrogen atom is a compound containing a phosphorus compound and, A ¹¹ ~ A ¹³ 1 numbered, A ¹² is a nitrogen atom a nitrogen atom is contained in the Do.

Moreover, the compound represented by the said General formula (11) has the "nitrogen-containing hetero ring" which can deepen LUMO, and is preferable from a viewpoint of reducing element voltage. Moreover, it is preferable also from a viewpoint of the small difference in chromaticity at the time of high temperature storage.

The molecular weight of the compound represented by the said General formula (1) is 400 or more and 1500 or less normally, It is preferable that it is 450 or more and 1200 or less, It is more preferable that it is 500 or more and 1100 or less, It is further more preferable that it is 550 or more and 1000 or less. If the molecular weight is 450 or more, it is advantageous for forming a good amorphous thin film, and if the molecular weight is 1200 or less, solubility and sublimation properties are improved, which is advantageous for improving the purity of the compound. In the organic electroluminescent element of this invention, it is preferable that the molecular weight of the compound represented by the said General formula (1) is 550 or more from a viewpoint of reducing the chromaticity difference at the time of high temperature storage. On the other hand, it is preferable that the molecular weight of the compound represented by the said General formula (1) is 1200 or less from a viewpoint of laminating | stacking the composition containing the compound represented by the said General formula (1) by vapor deposition.

When using the compound represented by the said General formula (1) as a host material of the light emitting layer of an organic electroluminescent element, or a charge transport material of the layer adjacent to a light emitting layer, the energy gap in a thin film state rather than a light emitting material (the organic electroluminescence of this invention) In the case where the light emitting material is a phosphorescent light emitting material such as an element, when the lowest triplet excitation (T ₁ ) energy) in the thin film state is large, the light emission is prevented from being quenched, which is advantageous for improving the efficiency. On the other hand, from the viewpoint of chemical stability of the compound, the energy gap and the T ₁ energy are preferably not too large.

T ₁ energy of the film state of the represented by the above-mentioned formula (1) compounds, 1.77 eV (40 ㎉ / ㏖ ) more than 3.51 eV (81 ㎉ / ㏖) or less is preferred, and, 2.39 eV (55 ㎉ / ㏖ ) above It is more preferable that it is 3.25 eV (75 dl / mol) or less. In the organic electroluminescent device of the present invention, it is preferable that the T ₁ energy of the compound represented by the general formula (1) is higher than the T ₁ energy of the phosphorescent material described later from the viewpoint of the light emission efficiency. In particular, when the emission color from the organic electroluminescent element is green (the emission peak wavelength is 490 to 580 nm), the T ₁ energy is 2.39 eV (55 dl / mol) or more and 2.82 eV (65 dl / mol) from the viewpoint of the luminescence efficiency. It is more preferable that it is below.

T ₁ energy can be obtained from the short wavelength end by measuring the phosphorescence emission spectrum of the thin film of the material. For example, a material is formed into a film thickness of about 50 nm by vacuum vapor deposition on the cleaned quartz glass substrate, and the phosphorescence emission spectrum of the thin film is F-7000 Hitachi spectrophotometer (Hitachi High Technologies) under liquid nitrogen temperature. Measure using The T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

From the viewpoint of stably operating the organic electroluminescent element at high temperatures during driving at high temperatures, or from the viewpoint of reducing the chromaticity difference at high temperatures, the compound represented by the general formula (1) in the organic electroluminescent element of the present invention It is preferable that this glass transition temperature is a compound of 100 degreeC or more. It is more preferable that the glass transition temperature (Tg) of the compound represented by the said General formula (1) is 100 degreeC or more and 400 degrees C or less, It is especially preferable that they are 120 degreeC or more and 400 degrees C or less, It is still more preferable that they are 140 degreeC or more and 400 degrees C or less.

When the purity of the compound represented by the general formula (1) is low, the impurity acts as a trap for charge transport or promotes deterioration of the device. Therefore, the higher the purity of the compound represented by the general formula (1) is preferable. Purity can be measured, for example, by high performance liquid chromatography (HPLC), and the area ratio of the compound represented by the general formula (1) when detected with a light absorption intensity of 254 nm is preferably 95.0% or more, More preferably, it is 97.0% or more, Especially preferably, it is 99.0% or more, Most preferably, it is 99.9% or more. As a method of improving the purity of the compound represented by the said General formula (1), a sublimation tablet etc. are mentioned, for example.

Although the specific example of the compound represented by the said General formula (1) is listed below, this invention is not limited to these.

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

The compound exemplified as the compound represented by the above general formula (1) is, for example, a metal catalyst (for example, Pd or the like) between a corresponding boronic acid or boronic acid ester or boronic acid ester salt and the like or a halogen compound or triflate compound corresponding thereto. Ni) and a ligand (such as triphenylphosphine or Buchwald ligand) can be synthesized by a coupling reaction (for example, Suzuki-Miyaura coupling). For example, it can synthesize | combine by the method of patent document 1 mentioned above.

In this invention, the use of the compound represented by the said General formula (1) is not limited, You may contain in any layer in an organic layer. As an introduction layer of the compound represented by the said General formula (1), it is preferable to contain in the light emitting layer, the layer between the said light emitting layer and a cathode (especially the layer adjacent to a light emitting layer), and the layer between the said light emitting layer and an anode. More preferably, the light emitting layer, the electron transport layer, the electron injection layer, the exciton block layer, the hole block layer, the electron block layer is contained in any one or more of the layers, and the light emitting layer, the electron transport layer, or the hole block layer It is more preferable, and what is contained in a light emitting layer or an electron carrying layer is especially preferable. Moreover, you may use the compound represented by the said General formula (1) in said multiple layers. For example, you may use for both a light emitting layer and an electron carrying layer.

When including the compound represented by the said General formula (1) in a light emitting layer, it is preferable to contain the compound represented by the said General formula (1) 0.1-99 mass% with respect to the total mass of the said light emitting layer, and it contains 1-97 mass% It is more preferable to make it, and it is still more preferable to contain 10-96 mass%. When containing the compound represented by the said General formula (1) further in layers other than a light emitting layer, it is preferable to contain 70-100 mass% with respect to the total mass of layers other than the light emitting layer, and contains 85-100 mass% It is more preferable.

(Phosphorescent light emitting material)

In this invention, it is preferable to have at least 1 sort (s) of phosphorescent light emitting material in the said light emitting layer. In the present invention, in addition to the phosphorescent light emitting material, a phosphorescent light emitting material different from the phosphorescent light emitting material or the phosphorescent light emitting material contained in the light emitting layer can be used as the light emitting material.

For these fluorescent light emitting materials and phosphorescent light emitting materials, for example, paragraphs [0100] to [0164] of JP 2008-270736 A and paragraphs [0088] to [0090] of JP 2007-266458 The matters described in detail and described in these publications can be applied to the present invention.

Phosphorescent light emitting materials that can be used in the present invention include, for example, US6303238 B1, US6097147, WO00 / 57676, WO00 / 70655, WO01 / 08230, WO01 / 39234 A2, WO01 / 41512 A1, WO02 / 02714 A2, WO02 / 15645 A1, WO02 / 44189 A1, WO05 / 19373 A2, JP 2001-247859, JP 2002-302671, JP 2002-117978, JP 2003-133074, JP 2002 -235076, JP 2003-123982, JP 2002-170684, EP1211257, JP 2002-226495, JP 2002-234894, JP 2001-247859, JP 2001 -298470, JP 2002-173674, JP 2002-203678, JP 2002-203679, JP 2004-357791, JP 2006-256999, JP 2007-19462 , Japanese Unexamined Patent Publication No. 2007-84635, Japanese Unexamined Patent Publication No. 2007-96259, etc. The phosphorescence emitting compound described, and the like, among which, more preferable light emitting materials include iridium (Ir) complexes, platinum (Pt) complexes, Cu complexes, Re complexes, W complexes, Rh complexes, Ru complexes, Pd complexes, Phosphorescent metal complex compounds, such as Os complex, Eu complex, Tb complex, Gd complex, Dy complex, and Ce complex, are mentioned. Particularly preferred are iridium (Ir) complexes, platinum (Pt) complexes, or Re complexes, including at least one coordination mode among metal-carbon bonds, metal-nitrogen bonds, metal-oxygen bonds, metal-sulfur bonds Iridium (Ir) complexes, platinum (Pt) complexes, or Re complexes are preferred. Further, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, iridium (Ir) complexes and platinum (Pt) complexes are particularly preferable, and iridium (Ir) complexes are most preferred.

It is preferable to contain these phosphorescent metal complex compounds with the compound represented by the said General formula (1) in a light emitting layer.

As a phosphorescent light-emitting material contained in the said light emitting layer, it is preferable to use the iridium (Ir) complex represented by general formula (E-1) shown below. Hereinafter, the iridium (Ir) complex represented by general formula (E-1) is demonstrated.

[Formula 25]

In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.

A ₁ represents a group of atoms which together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms.

B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom.

(X-Y) represents a monoanionic bidentate ligand.

_nE1 represents the integer of 1-3.

_nE1 represents the integer of 1-3, Preferably it is 2 or 3. When n _E1 is 2 or 3, a plurality of ligands may be the same as or different from each other.

Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom. Z ¹ and Z ² are preferably carbon atoms.

A ₁ represents a group of atoms which together with Z ¹ and a nitrogen atom form a heterocyclic ring of 5 or 6 atoms. Examples of the 5 or 6 membered hetero ring containing A ₁ , Z ¹ and a nitrogen atom include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring and thiazole ring , Triazole ring, oxadiazole ring, thiadiazole ring and the like.

In view of stability of the complex, emission wavelength control and emission quantum yield, a 5 or 6 membered hetero ring formed of A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring More preferably a pyridine ring, an imidazole ring, a pyrazine ring, still more preferably a pyridine ring, an imidazole ring, and most preferably a pyridine ring.

Wherein A ^_1, Z ₁ and heterocyclic ring of 5 or 6 atoms which form the nitrogen atom is to have a substituent, substituents may be applied to the substituent group A. The substituent is appropriately selected for controlling the emission wavelength or potential, but in the case of shortening, an electron donating group, a fluorine atom, an aromatic ring group is preferable, and an alkyl group, dialkylamino group, alkoxy group, fluorine atom, aryl group, hetero An aryl group etc. are selected. Moreover, when making it long-wavelength, an electron withdrawing group is preferable, and a cyano group, a perfluoroalkyl group, etc. are preferable, for example. It is preferable that an alkyl group, a cycloalkyl group, an aryl group, etc. are selected for the purpose of adjusting intermolecular interaction.

As a substituent on carbon, Preferably, they are an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, and a fluorine atom.

As a substituent on nitrogen, Preferably, they are an alkyl group, an aryl group, and a heteroaryl group, and an alkyl group and an aryl group are preferable from a stability point of a complex.

The substituents may be linked to each other to form a condensed ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring and a pyrazole. A ring, a thiophene ring, a furan ring, etc. are mentioned. The ring formed may have a substituent and the substituent on the carbon atom mentioned above and the substituent on a nitrogen atom are mentioned as a substituent.

B ₁ represents a 5 or 6 membered ring containing Z ² and a carbon atom. Examples of the 5 or 6 membered ring formed of B ₁ , Z ² and carbon atoms include benzene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring and oxazole ring , Thiazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiophene ring, furan ring and the like.

In view of stability, the emission wavelength control and a light emission quantum yield of the complex, B _1, Z ^2, and is preferably a 5- or 6-membered ring formed of carbon atoms, a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole Ring, thiophene ring, More preferably, they are a benzene ring, a pyridine ring, a pyrazole ring, More preferably, they are a benzene ring and a pyridine ring.

The 5 or 6 membered ring formed of said B <_1> , Z <^2> and a carbon atom may have a substituent, As said substituent group A as a substituent on a carbon atom, the following substituent group B is applicable as a substituent on a nitrogen atom. .

As a substituent on carbon, Preferably, they are an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, and a fluorine atom.

《Substituent Group B》

Alkyl group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, for example methyl, ethyl, isopropyl, tert-butyl, n-octyl, n-decyl , n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl group (preferably C2-C30, more preferably C2-C20, Especially preferably, it is C2-C10 For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc. are mentioned, an alkynyl group (preferably C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2 It is -10, for example, propargyl, 3-pentynyl, etc., an aryl group (preferably C6-C30, More preferably, it is C6-C20, Especially preferably, it is C6-C12 For example, phenyl, p-methylphenyl, naphthyl, anthryl etc. are mentioned. ), A cyano group, a heterocyclic group (heteroaryl group is included, Preferably it is C1-C30, More preferably, it is C1-C12, As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, phosphorus, for example) Atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxa Zolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl , Benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like). These substituents may further be substituted and the group selected from the substituent group B demonstrated above as a further substituent is mentioned.

The substituent on the carbon is appropriately selected for the control of the emission wavelength or the potential, but in the case of making a long wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, a heteroaryl group, or the like. Is selected. Moreover, when shortening, an electron withdrawing group is preferable, for example, a fluorine atom, a cyano group, a perfluoroalkyl group, etc. are selected. For the purpose of adjusting the intermolecular interaction, an alkyl group, a cycloalkyl group, an aryl group or the like is preferably selected.

As a substituent on nitrogen, Preferably, they are an alkyl group, an aryl group, and a heteroaryl group, and an alkyl group and an aryl group are preferable from a stability point of a complex. The substituents may be linked to each other to form a condensed ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring and a pyrazole. A ring, a thiophene ring, a furan ring, etc. are mentioned. The ring formed may have a substituent and the substituent on the carbon atom mentioned above and the substituent on a nitrogen atom are mentioned as a substituent.

Moreover, the substituent of the 5 or 6-membered heterocyclic ring formed with said A <_1> , Z <^1> and a nitrogen atom, and the substituent of the 5 or 6-membered ring formed with said B <_1> , Z <^2> and a carbon atom are connected, and the same condensed ring as mentioned above May be formed.

(X-Y) represents a bidentate monoanionic ligand. Examples of bidentate monoanionic ligands are described on pages 89-90 of Lamansky International Publication No. 02/15645.

As a bidentate monoanionic ligand represented by (X-Y), Preferably, it is a bidentate monoanion ligand represented by following General formula (L-1).

[Formula 26]

In General Formula (L-1), R ^L1 and R ^L2 each independently represent an alkyl group, an aryl group, or a heteroaryl group.

R ^L3 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.

The alkyl group represented by R ^L1 to R ^L3 may have a substituent, or may be saturated or unsaturated. The following substituent Z 'is mentioned as a substituent in the case of having a substituent, A preferable substituent Z' is a group which consists of a phenyl group, heteroaryl group, a fluorine atom, a silyl group, an amino group, a cyano group, or a combination thereof, a phenyl group, A fluorine atom and a cyano group are more preferable. The alkyl group represented by R ^L1 to R ^L3 is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms.

<< substituent Z '>>

Alkyl group (preferably C1-C10, More preferably, it is C1-C6, More preferably, it is C1-C4, For example, methyl, ethyl, isopropyl, n-propyl, tert- butyl, isobutyl, n-butyl, neopentyl, n-pentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably C2-C8, More preferably, it is C2-C5) For example, vinyl etc.) and an aryl group (C6-C30, More preferably, it is C6-C20, For example, a phenyl group, a naphthyl group, anthracenyl group, tetrasenyl group, pyrenyl group, pe And a arylenyl group, a triphenylenyl group, and a chrysenyl group, and a heteroaryl group (preferably having 4 to 30 carbon atoms, more preferably 4 to 20 carbon atoms, for example, pyridine, pyrazine, pyrimidine, pyridazine , Triazine, thiophene, furan, oxazole, thiazole, imidazole , Pyrazole, triazole, oxadiazole, thiadiazole, etc.), an alkoxy group (preferably C1-C8, More preferably, it is C1-C5, For example, a methoxy group, an ethoxy group) , n-propyloxy group, iso-propyloxy group, etc.), phenoxy group, halogen atom (preferably fluorine atom), silyl group (preferably C4-C30, more preferably C4-C) 20, trimethylsilyl group, triethylsilyl group, triphenylsilyl group, etc.), amino group (preferably C2-C60, more preferably C2-C40, dimethylamino group, diethylamino group, A diphenylamino group, etc.), a cyano group, or a group formed by combining them, and a plurality of substituents Z 'may be bonded to each other to form an aryl ring. A phenyl ring, a pyridine ring, etc. are mentioned as an aryl ring which some substituent Z 'combines and forms, and a phenyl ring is preferable.

The aryl group represented by R <^L1> -R <^L3> may be condensed and may have a substituent. As a substituent in the case of having a substituent, the substituent Z 'mentioned above is mentioned, As a substituent Z', an alkyl group or an aryl group is preferable, and an alkyl group is more preferable. The aryl group represented by R ^L1 to R ^L3 is preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 18 carbon atoms.

The heteroaryl group represented by R ^L1 to R ^L3 may be condensed or may have a substituent. As a substituent in the case of having a substituent, the substituent Z 'mentioned above is mentioned, As a substituent Z', an alkyl group or an aryl group is preferable, and an alkyl group is more preferable. The heteroaryl group represented by R ^L1 to R ^L3 is preferably a heteroaryl group having 4 to 12 carbon atoms, and more preferably a heteroaryl group having 4 to 10 carbon atoms.

R ^L1 and R ^L2 are preferably alkyl groups or aryl groups, more preferably alkyl groups or phenyl groups, and particularly preferably alkyl groups.

As an alkyl group represented by R <^L1> and R <^L2> , Preferably it is an alkyl group of 1-8 carbon atoms, More preferably, it is an alkyl group of 1-5 carbon atoms, For example, a methyl group, an ethyl group, n-propyl group , iso-propyl group, iso-butyl group, t-butyl group, n-butyl group, cyclohexyl group, etc. are mentioned, and methyl group, ethyl group, iso-butyl group, or t-butyl group is preferable, and a methyl group is especially desirable.

R ^L3 is preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

A preferred embodiment of the iridium (Ir) complex represented by the general formula (E-1) is an iridium (Ir) complex material represented by the following general formula (E-2).

Next, general formula (E-2) is demonstrated.

[Formula 27]

In the general formula (E-2), A ~ ^{E1 E8} A represents a nitrogen atom or a CR ^E independently.

R ^E represents a hydrogen atom or a substituent.

(X-Y) represents a monoanionic bidentate ligand.

_nE2 represents the integer of 1-3.

A ^E1 to A ^E8 each independently represent a nitrogen atom or CR ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. As a ring formed, the thing similar to the condensed ring mentioned in general formula (E-1) mentioned above is mentioned. As the substituent represented by R ^E may be applied to, all the substituent groups as A.

When A ^E1 to A ^E4 are preferably CR ^E , and when A ^E1 to A ^E4 are CR ^E , R ^E of A ^E3 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, or an aryloxy group. , A fluorine atom or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom or a fluorine atom, A ^E1 , A ^E2 and R ^E of A ^E4 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, and more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group or an aryl octane. It is a time period or a fluorine atom, Especially preferably, it is a hydrogen atom.

When A ^E5 to A ^E8 is preferably CR ^E , and when A ^E5 to A ^E8 is CR ^E , preferably R ^E is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, or a dialkyl. It is an amino group, a diarylamino group, an alkyloxy group, a cyano group, or a fluorine atom, More preferably, it is a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, or a fluorine atom, More preferably, Is a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, substituents may be linked to each other to form a condensed ring structure. When shifting the emission wavelength toward the short wavelength side, it is preferable that A ^E6 is a nitrogen atom.

(XY) and n _E2 are synonymous with (XY) and n _E1 in general formula (E-1), and its preferable range is also the same.

The more preferable aspect of the compound represented by said general formula (E-2) is a compound represented with the following general formula (E-3).

[Formula 28]

In General Formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, A perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O) R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and further a substituent Z You may have it. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

A represents CR 'or a nitrogen atom, and R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -C (O ), R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Any two of R ^T1 to R ^T7 and R 'may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to The 7-membered ring may further have a substituent Z. Of these, the case in which the chukhwan R ^T1 and R ^{T7, T5,} or R and R ^T6 form a benzene ring are preferred, and is particularly preferable in the case of forming a benzene ring is chukhwan as R and R ^{T5 T6.}

Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) N _{(R ") 2, -CN,} -NO 2, -SO 2, -SOR", -SO 2 R represents a ", or -SO ₃ R", R "is a hydrogen atom, an alkyl group, a perhaloalkyl, each independently , Alkenyl group, alkynyl group, heteroalkyl group, aryl group or heteroaryl group.

(XY) represents a monoanionic ligand. _nE3 represents the integer of 1-3.

Examples of the alkyl group which may have a substituent, may be saturated or unsaturated, and may be substituted, the substituent Z described above. As an alkyl group represented by R <^T1> -R <^T7> and R ', Preferably it is an alkyl group of 1-8 carbon atoms, More preferably, it is an alkyl group of 1-6 carbon atoms, For example, a methyl group, an ethyl group, i-propyl group, a cyclohexyl group, t-butyl group etc. are mentioned.

The cycloalkyl group may have a substituent, may be saturated or unsaturated, or may be substituted with the substituent Z described above. As a cycloalkyl group represented by R <^T1> -R <^T7> and R ', Preferably it is a cycloalkyl group of 4-7 ring atoms, More preferably, it is a cycloalkyl group of 5-6 carbon atoms, for example cyclophene Tyl group, cyclohexyl group, etc. are mentioned.

As an alkenyl group represented by R <^T1> -R <^T7> and R ', Preferably it is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl, and the like.

As an alkynyl group represented by R <^T1> -R <^T7> and R ', Preferably it is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, ethynyl, Pro Pargyl, 1-propynyl, 3-pentynyl and the like.

Examples of the perfluoroalkyl group represented by R ^T1 to R ^T7 and R 'include those in which all hydrogen atoms of the aforementioned alkyl group are substituted with fluorine atoms.

As an aryl group represented by R <^T1> -R <^T7> and R ', Preferably a C6-C30 substituted or unsubstituted aryl group, for example, a phenyl group, a tolyl group, a naphthyl group, etc. are mentioned.

The heteroaryl group represented by R ^T1 to R ^T7 and R 'is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 or 6 atoms, for example Pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indole Aryl group, furyl group, benzofuryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothia Zolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isooxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, Thiazolinyl group, sulfolanyl group, carbazolyl group, dibenzofuryl group, Benzothienyl group, and the like based degrees turned 7 flutes. Preferable examples are pyridyl group, pyrimidinyl group, imidazolyl group and thienyl group, and more preferably pyridyl group and pyrimidinyl group.

R ^T1 to R ^T7 and R 'are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, and a heteroaryl group, more preferably Is a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, an aryl group, More preferably, they are a hydrogen atom, an alkyl group, and an aryl group. As the substituent Z, an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom is more preferable.

Any two of R ^T1 to R ^T7 and R 'may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 The atomic ring may further have a substituent Z. The definitions and preferred ranges of the cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined in R ^T1 to R ^T7 and R '.

In addition, A is a ', R ^T1 ~ R ^T7, and R together with represents a' of 0 to two are each an alkyl group or a phenyl group CR, is particularly preferred if the remainder is a hydrogen atom, R ^T1 ~ R ^T7, and It is especially preferable when 0-2 are alkyl groups in R ', and all remainder are hydrogen atoms.

It is preferable that n _E3 is 2 or 3. When n _E3 is 2 or 3, the plurality of ligands may be the same or different. It is preferable that the kind of ligand in a complex is comprised from 1-2 types.

(X-Y) is synonymous with (X-Y) in General formula (E-1), and its preferable range is also the same.

One of the preferable forms of the compound represented by said general formula (E-3) is a compound represented with the following general formula (E-4).

[Formula 29]

R ^T1 to R ^T4 , A, (XY) and n _E4 in General Formula (E-4) are R ^T1 to R ^T4 , A, (XY) and n _{E3 in} General Formula (E-3). It is synonymous with and a preferable range is also the same. R ₁ 'to R ₅ ' each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, and -C (O) R , -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

Any two of R ₁ ′ to R ₅ ′ may be bonded to each other to form a condensed 4 to 7 membered ring, and the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered The ring may further have a substituent Z.

Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) N _{(R ") 2, -CN,} -NO 2, -SO 2, -SOR", -SO 2 R represents a ", or -SO ₃ R", R "is a hydrogen atom, an alkyl group, a perhaloalkyl, each independently , Alkenyl group, alkynyl group, heteroalkyl group, aryl group or heteroaryl group.

Moreover, the preferable range in R <_1> -R <_5>'is the same as that of R <^T1> -R <^T7> , R' in general formula (E-3). Moreover, especially when A represents CR ', 0-2 of R <^T1> -R <^T4> , R', and R <_1> -R <_5>'are an alkyl group or a phenyl group, and all remainder are hydrogen atoms are especially preferable. It is more preferable that 0-2 are alkyl groups, and the remainder is a hydrogen atom among R <^T1> -R <^T4> , R ', and R <_1> -R <_5>'.

Although the specific example of the compound represented by the said general formula (E-1) is listed below, it is not limited to the following.

[Formula 30]

[Formula 31]

[Formula 32]

The compound illustrated as a compound represented by the said general formula (E-1) can be synthesize | combined by the method of Unexamined-Japanese-Patent No. 2009-99783, the various methods of US Pat. No. 7279232, etc. After synthesis, purification by column chromatography, recrystallization or the like is preferably followed by purification by sublimation purification. By sublimation purification, not only an organic impurity can be separated but an inorganic salt, a residual solvent, etc. can be removed effectively.

Although it is preferable to contain the said phosphorescence emitting material in a light emitting layer, the use is not limited and may be further contained in any layer in an organic layer.

It is preferable that the said phosphorescence emitting material in the said light emitting layer is contained 0.1 mass%-50 mass% with respect to the mass of the whole compound which forms a light emitting layer generally in the said light emitting layer, and it is 1 mass%-50 mass from a viewpoint of durability and external quantum efficiency. It is more preferable to contain%, and it is especially preferable to contain 2 mass%-40 mass%.

It is especially preferable in this invention to use the compound represented by either of general formula (1)-(7) and the compound represented by any of general formula (E-1)-(E-4) in a light emitting layer.

(3) other host materials

As a host material which can be used for the said light emitting layer other than the compound represented by the said General formula (1), the compound which has the following structures as a partial structure is mentioned, for example.

Aromatic hydrocarbons, pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, Arylamine, amino substituted chalcone, styrylanthracene, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, porphyrin compound, polysilane compound, poly (N-vinylcarbazole) Conductive polymer oligomers such as aniline copolymers, thiophene oligomers and polythiophenes, organosilanes, carbon films, pyridine, pyrimidines, triazines, imidazoles, pyrazoles, triazoles, oxazoles, oxadiazoles, fluorine Heterocyclic tetracarboxylic acids such as lennon, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compound, naphthaleneperylene Various metal complexes represented by metal complexes of anhydrides, phthalocyanines and 8-quinolinol derivatives, metal complexes containing metal phthalocyanine, benzoxazole or benzothiazole, and derivatives thereof (which may have a substituent or a condensation); Can be mentioned.

(Other layers)

The organic electroluminescent element of this invention may have other layers other than the said light emitting layer.

As other organic layers other than the said light emitting layer which the said organic layer may have, a hole injection layer, a hole transport layer, a block layer (hole block layer, an exciton block layer, etc.), an electron carrying layer, etc. are mentioned. Although the following is mentioned as said specific laminated constitution, This invention is not limited to these constitutions.

Anode / hole transport layer / light emitting layer / electron transport layer / cathode,

Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,

Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,

Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,

Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode,

Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,

Anode / hole injection layer / hole transport layer / block layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.

It is preferable that the organic electroluminescent element of this invention contains (A) at least 1 organic layer preferably arrange | positioned between the said anode and the said light emitting layer. Examples of the organic layer preferably disposed between the anode (A) and the light emitting layer include a hole injection layer, a hole transport layer, and an electron blocking layer from the anode side.

It is preferable that the organic electroluminescent element of this invention contains (B) at least 1 organic layer preferably arrange | positioned between the said cathode and the said light emitting layer. Examples of the organic layer preferably disposed between the cathode (B) and the light emitting layer include an electron injection layer, an electron transport layer, and a hole block layer from the cathode side.

Specifically, an example of a preferred embodiment of the organic electroluminescent device of the present invention is the embodiment described in FIG. 1, and the hole injection layer 4, the hole transport layer 5, and the light emitting layer 6 from the anode side 3 as the organic layer. ), The hole block layer 7 and the electron transport layer 8 are the embodiments in which they are laminated in this order.

Hereinafter, other layers other than the said light emitting layer which these organic electroluminescent elements of this invention may have are demonstrated.

(A) an organic layer preferably disposed between the anode and the light emitting layer

First, (A) The organic layer preferably arranged between the anode and the light emitting layer will be described.

(A-1) hole injection layer, hole transport layer

The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or anode side and transporting them to the cathode side.

Regarding the hole injection layer and the hole transport layer, the matters described in paragraphs [0165] to [0167] of JP2008-270736A can be applied to the present invention.

The hole injection layer preferably contains an electron accepting dopant. By incorporating the electron-accepting dopant in the hole injection layer, there are effects such as hole injection properties, a driving voltage, a efficiency, and the like. The electron-accepting dopant may be any of an organic material and an inorganic material, as long as it is capable of drawing electrons from the material to be doped to generate radical cations. For example, tetracyanoquinomimethane (TCNQ), tetrafluoro Tetracyanoquinomimethane (F ₄ -TCNQ), molybdenum oxide and the like.

It is preferable to contain 0.01 mass%-50 mass% with respect to the mass of the whole compound which forms a hole injection layer, and, as for the electron accepting dopant in a hole injection layer, it is more preferable that 0.1 mass%-40 mass% are contained, 0.2 mass% It is more preferable to contain-30 mass%.

(A-2) electron block layer

The electron block layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from escaping to the anode side. In the present invention, the electron blocking layer can be formed as the organic layer adjacent to the light emitting layer and the anode side.

The T ₁ energy in the film state of the organic compound constituting the electron block layer is preferably higher than the T ₁ energy of the luminescent material in order to prevent energy transfer of excitons generated in the light emitting layer and to reduce luminous efficiency.

As an example of the organic compound which comprises an electron block layer, what was mentioned as the above-mentioned hole transport material is applicable, for example.

As thickness of an electron blocking layer, it is preferable that it is 1 nm-500 nm, It is more preferable that it is 5 nm-200 nm, It is further more preferable that it is 10 nm-100 nm.

The electron blocking layer may be a single layer structure composed of one or two or more kinds of the above-described materials, or may be a multilayer structure composed of a plurality of layers of the same composition or different compositions.

(A-3) A material that is particularly preferably used for the organic layer preferably disposed between the anode and the light emitting layer.

[Compound represented by general formula (M-1)]

The organic electroluminescent element of this invention is a material used especially preferably for the organic layer arrange | positioned between the said (A) anode and the said light emitting layer, The compound represented by at least 1 sort (s) of following General formula (M-1) is mentioned. Can be.

Although the compound represented by the said General formula (M-1) is more preferable to be contained in the organic layer adjacent to the light emitting layer between a light emitting layer and an anode, the use is not limited and may be contained in any layer in an organic layer further. As an introduction layer of the compound represented by the said General formula (M-1), it can contain in the light emitting layer, a hole injection layer, a hole transport layer, an electron carrying layer, an electron injection layer, a charge block layer, or a plurality.

As for the organic layer adjacent to the light emitting layer between the light emitting layer and anode which the compound represented by the said General formula (M-1) contains, it is more preferable that it is an electron block layer or a hole transport layer.

[Formula 33]

In Formula (M-1), Ar ₁ and Ar ₂ are each independently selected from alkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino, thiomorpholino, N, O, and S 5 or 6 membered heterocycloalkyl or cycloalkyl containing one or more hetero atoms may be represented, and may further have a substituent Z. In addition, Ar ₁ and Ar ₂ may be bonded to each other by a single bond, alkylene, or alkenylene (with or without a condensed ring) to form a condensed 5- to 9-membered ring.

Ar <_3> represents P-valent alkyl, aryl, heteroaryl, arylamino, and may further have a substituent Z.

Z is independently a halogen atom, -R ", -OR", -N (R ") ₂ , -SR", -C (O) R ", -C (O) OR", -C (O) N _{(R ") 2, -CN,} -NO 2, -SO 2, -SOR", -SO 2 R represents a ", or -SO ₃ R", R "is a hydrogen atom, an alkyl group, a perhaloalkyl, each independently , Alkenyl group, alkynyl group, heteroalkyl group, aryl group or heteroaryl group.

p is an integer of _1-4 and when p is 2 or more, Ar <_1> and Ar <_2> may respectively be same or different.

Another preferable form of the compound represented by said general formula (M-1) is a case represented by the following general formula (M-2).

[Formula 34]

In said general formula (M-2), R <^M1> represents an alkyl group, an aryl group, or heteroaryl group.

R ^M2 to R ^M23 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, a cyano group, a nitro group, or a fluorine atom.

In said general formula (M-2), R <^M1> represents an alkyl group (preferably C1-C8), an aryl group (preferably C6-C30), or heteroaryl group (preferably C4-C12). These may have the substituent Z mentioned above. R ^M1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. As a preferable substituent in the case where the aryl group of R <^{M1> has} a substituent, an alkyl group, a halogen atom, a cyano group, an aryl group, an alkoxy group is mentioned, An alkyl group, a halogen atom, a cyano group, or an aryl group is more preferable, and an alkyl group and a cyan A no group or an aryl group is more preferable. The aryl group of R ^M1 is preferably a phenyl group which may have a substituent Z, and more preferably a phenyl group which may have an alkyl group or a cyano group.

R ^M2 to R ^M23 each independently represent a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), a heteroaryl group (preferably having 4 to 12 carbon atoms), and an alkoxy group (Preferably having 1 to 8 carbon atoms), aryloxy group (preferably having 6 to 30 carbon atoms), amino group (preferably having 0 to 24 carbon atoms), silyl group (preferably having 0 to 18 carbon atoms), cyano group, nitro Group or a fluorine atom, and they may have the substituent Z described above.

R ^M2 , R ^M7 , R ^M8 , R ^M15 , R ^M16 and R ^M23 are preferably an alkyl group or an aryl group which may have a hydrogen atom or a substituent Z, and more preferably a hydrogen atom.

R ^M4 , R ^M5 , R ^M11 , R ^M12 , R ^M19 and R ^M20 are preferably a hydrogen atom, an alkyl group or an aryl group which may have a substituent Z, or a fluorine atom, and more preferably a hydrogen atom.

R ^M3 , R ^M6 , R ^M9 , R ^M14 , R ^M17 and R ^M22 are preferably a hydrogen atom, an alkyl group which may have a substituent Z or an aryl group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, Or an alkyl group which may have a substituent Z, More preferably, it is a hydrogen atom.

R ^M10 , R ^M13 , R ^M18 and R ^M21 are preferably a hydrogen atom, an alkyl group which may have a substituent Z, an aryl group, a heteroaryl group or an amino group, a nitro group, a fluorine atom, or a cyano group, more preferably It is an alkyl group or an aryl group, a nitro group, a fluorine atom, or a cyano group which may have a hydrogen atom and a substituent Z, More preferably, it is a hydrogen atom or the alkyl group which may have a substituent Z. As a substituent in the case where an alkyl group has a substituent, a fluorine atom is preferable, Carbon number of the alkyl group which may have a substituent Z becomes like this. Preferably it is 1-6, More preferably, it is 1-4.

Another preferable form of the compound represented by said general formula (M-1) is a case represented by the following general formula (M-3).

[Formula 35]

In the general formula (M-3), R ^S1 to R ^S5 are each independently an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R,- C (O) R, -NR ₂ , -NO ₂ , -OR, a halogen atom, an aryl group or a heteroaryl group, and may further have a substituent Z. R each independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. When there exist some R <^S1> -R <^S5> , they may combine with each other, may form the ring, and may have a substituent Z further.

a represents the integer of 0-4, and when some R <^S1> exists, they may be same or different, and may mutually combine and form a ring. b-e respectively independently represent the integer of 0-5, and when some R <^S2> -R <^S5> respectively exists, they may be same or different, and arbitrary two may combine and form a ring.

q is an integer of 1-5, when q is 2 or more, some R <^S1> may be same or different, and may combine with each other and may form the ring.

Examples of the alkyl group which may have a substituent, may be saturated or unsaturated, and may be substituted, the substituent Z described above. The alkyl group represented by R ^S1 to R ^S5 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, or an i-propyl group. , Cyclohexyl group, t-butyl group and the like.

The cycloalkyl group may have a substituent, may be saturated or unsaturated, or may be substituted with the substituent Z described above. As a cycloalkyl group represented by R <^S1> -R <^S5> , Preferably it is a cycloalkyl group of 4-7 ring atoms, More preferably, it is a cycloalkyl group of 5-6 carbon atoms, For example, a cyclopentyl group, Cyclohex And practical skills.

R ^S1 ~ alkenyl group represented by R ^S5 is preferably a carbon number of 2 to 30, more preferably from 2 to 20 carbon atoms, particularly preferably a carbon number of 2-10, such as vinyl, allyl, 1-propenyl , 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl, and the like.

As an alkynyl group represented by R <^S1> -R <^S5> , Preferably it is C2-C30, More preferably, it is C2-C20, Especially preferably, it is C2-C10, For example, ethynyl, Propargyl, 1 -Propynyl, 3-pentynyl, and the like.

Examples of the perfluoroalkyl group represented by R ^S1 to R ^S5 include those in which all hydrogen atoms of the alkyl group described above are substituted with fluorine atoms.

As an aryl group represented by R <^S1> -R <^S5> , Preferably, a C6-C30 substituted or unsubstituted aryl group, for example, a phenyl group, a tolyl group, a biphenyl group, a terphenyl group, etc. are mentioned.

The heteroaryl group represented by R ^S1 to R ^S5 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 or 6 atoms, for example, a pyridyl group, Pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnaolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, fu Aryl group, benzofuryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, Isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isooxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, thiazolinyl group , Sulfolanyl group, carbazolyl group, dibenzofuryl group, dibenzo On it may be mentioned groups, such as group turn-pyrido [deg. Preferable examples are pyridyl group, pyrimidinyl group, imidazolyl group and thienyl group, and more preferably pyridyl group and pyrimidinyl group.

R ^S1 to R ^S5 are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, a heteroaryl group, more preferably a hydrogen atom, An alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group, More preferably, they are a hydrogen atom, an alkyl group, and an aryl group. As the substituent Z, an alkyl group, an alkoxy group, a fluoro group, a cyano group, and a dialkylamino group are preferable, and a hydrogen atom and an alkyl group are more preferable.

Any two of R ^S1 to R ^S5 may be bonded to each other to form a condensed 4 to 7 membered ring, the condensed 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered ring is Furthermore, you may have a substituent Z. The definitions and preferred ranges of the cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined in R ^S1 to R ^S5 .

When using the compound represented by the said General formula (M-1) in a positive hole transport layer, it is preferable that 50-100 mass% of compounds represented by the said General formula (M-1) are contained, and 80-100 mass% is contained It is preferable, and it is especially preferable that 95-100 mass% is contained.

Moreover, when using the compound represented by the said General formula (M-1) for several organic layers, it is preferable to contain in said range in each layer.

The compound represented by the said General formula (M-1) may contain only one type in any organic layer, and may contain the compound represented by several general formula (M-1) in combination at arbitrary ratios.

As thickness of the positive hole transport layer containing the compound represented by the said general formula (M-1), it is preferable that it is 1 nm-500 nm, It is more preferable that it is 3 nm-200 nm, It is still more preferable that it is 5 nm-100 nm. Do. In addition, the hole transport layer is preferably formed in contact with the light emitting layer.

The lowest triplet excitation triplet (T ₁ ) energy in the film state of the compound represented by the general formula (M-1) is preferably 1.77 eV (40 kV / mol) or more and 3.51 eV (81 kV / mol) or less, and 2.39 eV. It is more preferable that it is (55 dl / mol) or more and 3.25 eV (75 dl / mol) or less. In the organic electroluminescent device of the present invention, it is preferable that the T ₁ energy of the compound represented by the general formula (M-1) is higher than the T ₁ energy of the phosphorescent light emitting material described above from the viewpoint of the light emission efficiency. In particular, when the emission color from the organic electroluminescent element is green (the emission peak wavelength is 490 to 580 nm), the T ₁ energy is 2.39 eV (55 dl / mol) or more and 2.82 eV (65 dl / mol) from the viewpoint of the luminescence efficiency. More preferably).

The hydrogen atom which comprises the said general formula (M-1) also contains the isotope of hydrogen (deuterium atom etc.). In this case, all the hydrogen atoms in the compound may be substituted with a hydrogen isotope, or a mixture may be a compound in which a part contains a hydrogen isotope.

The compound represented by the said general formula (M-1) can be synthesize | combined combining various well-known synthesis methods. Most commonly, the carbazole compound is synthesized by dehydrogenation after aza-copper potential reaction of a condensate of arylhydrazine and cyclohexane derivatives (LF Tieze, Th. Eicher, Takano, Ogasawara Station, Precision Organics). Synthesis, p. 339 (Nankodo). Moreover, regarding the coupling reaction using the palladium catalyst of the obtained carbazole compound and the halogenated aryl compound, tetrahedron Letters No. 39, page 617 (1998), tetrahedron letter Nos. 39, 2367 page (1998), and Tetrahedron Letters 40, page 6393 (1999) etc. are mentioned. It does not specifically limit about reaction temperature and reaction time, The conditions described in the said document can be applied.

Although it is preferable to form a thin layer by the vacuum vapor deposition process, the compound represented by the said General formula (M-1) can also use suitably wet processes, such as solution coating. It is preferable that it is 2000 or less from a viewpoint of vapor deposition aptitude and solubility, It is more preferable that it is 1200 or less, It is especially preferable that it is 800 or less. In addition, from the viewpoint of vapor deposition aptitude, if the molecular weight is too small, the vapor pressure becomes small, and a change from the gaseous phase to a solid phase does not occur, and it becomes difficult to form an organic layer. Therefore, 250 or more is preferable, and 300 or more is particularly preferable.

Although the specific example of a compound represented by the said general formula (M-1) is shown below, this invention is not limited to these.

[Formula 36]

[Formula 37]

[Formula 38]

[Formula 39]

[Formula 40]

(B) an organic layer preferably disposed between the cathode and the light emitting layer

Next, an organic layer preferably disposed between the cathode (B) and the light emitting layer will be described.

(B-1) electron injection layer, electron transport layer

The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or cathode side and transporting them to the anode side. The electron injection material and electron transport material used for these layers may be a low molecular compound or a high molecular compound.

As an electron transport material, the compound represented by the said General formula (1) can be used. As other electron transport materials, pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives and imidazoles Aroma of derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidene methane derivatives, distyrylpyrazine derivatives, naphthalene, perylene, etc. Organic silane derivatives represented by various metal complexes represented by metal complexes of cyclic tetracarboxylic anhydrides, phthalocyanine derivatives and 8-quinolinol derivatives, metal complexes containing metal phthalocyanine, benzoxazole and benzothiazole as ligands It is preferable that it is a layer containing etc.

It is preferable that the thickness of an electron injection layer and an electron carrying layer is 500 nm or less from a viewpoint of lowering a drive voltage, respectively.

As thickness of an electron carrying layer, it is preferable that it is 1 nm-500 nm, It is more preferable that it is 5 nm-200 nm, It is further more preferable that it is 10 nm-100 nm. Moreover, as thickness of an electron injection layer, it is preferable that it is 0.1 nm-200 nm, It is more preferable that it is 0.2 nm-100 nm, It is still more preferable that it is 0.5 nm-50 nm.

The electron injection layer and the electron transport layer may have a single layer structure composed of one or two or more kinds of the above-described materials, or may have a multilayer structure composed of a plurality of layers of the same composition or different compositions.

It is preferable that an electron injection layer contains an electron donating dopant. By incorporating an electron donating dopant in the electron injection layer, there is an effect that the electron injection property is improved, the driving voltage is lowered, and the efficiency is improved. The electron donating dopant may be any of an organic material and an inorganic material as long as it can impart electrons to the material to be doped to generate radical anions. For example, tetrathiafullbarene (TTF) and tetrathianaphthacene And dihydroimidazole compounds such as (TTT) and bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

It is preferable to contain 0.01 mass%-50 mass% with respect to the total mass of the compound which forms an electron injection layer, and, as for the electron donating dopant in an electron injection layer, it is more preferable that 0.1 mass%-40 mass% are contained, and it is 0.5 mass It is more preferable to contain 30% by mass.

(B-2) hole block layer

The hole block layer is a layer having a function of preventing the holes transported from the anode side to the light emitting layer from escaping to the cathode side. In the present invention, the hole block layer can be formed as an organic layer adjacent to the light emitting layer and the cathode side.

The T ₁ energy in the film state of the organic compound constituting the hole block layer is preferably higher than the T ₁ energy of the luminescent material in order to prevent energy transfer of excitons generated in the light emitting layer and to reduce luminous efficiency.

As an example of the organic compound which comprises a hole block layer, the compound represented by the said General formula (1) can be used.

Examples of other organic compounds constituting the hole block layer other than the compound represented by the general formula (1) include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (Aluminum (III) aluminum complexes such as bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline And phenanthroline derivatives such as (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)). In the present invention, the hole block layer is not limited to the function of actually blocking holes, and may have a function of not diffusing excitons of the light emitting layer into the electron transport layer or blocking energy transfer quenching. The compound of the present invention can also be preferably applied as a hole block layer.

The thickness of the hole block layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, still more preferably 10 nm to 100 nm.

The hole block layer may be a single layer structure composed of one or two or more kinds of the above-described materials, or may be a multilayer structure composed of a plurality of layers of the same composition or different compositions.

(B-3) A material that is particularly preferably used for the organic layer preferably disposed between the cathode and the light emitting layer.

The organic electroluminescent device of the present invention is a material which is particularly preferably used for the material of the organic layer preferably disposed between the cathode (B) and the light emitting layer, and the compound represented by the general formula (1), an aromatic hydrocarbon compound (especially And the compound represented by the following general formula (Tp-1) and the following general formula (O-1).

Hereinafter, the said aromatic hydrocarbon compound and the compound represented by the said general formula (O-1) are demonstrated.

Aromatic Hydrocarbon Compounds

The aromatic hydrocarbon compound is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the cathode, but its use is not limited, and may be further contained in any layer in the organic layer. As an introduction layer of the said aromatic hydrocarbon compound, it can contain in a light emitting layer, a hole injection layer, a hole transport layer, an electron carrying layer, an electron injection layer, an exciton block layer, a charge block layer, or a plurality.

The organic layer adjacent to the light emitting layer between the light emitting layer and the cathode containing the aromatic hydrocarbon compound is preferably a charge block layer or an electron transporting layer, more preferably an electron transporting layer.

It is preferable that the said aromatic hydrocarbon compound consists only of a carbon atom and a hydrogen atom from a viewpoint of the ease of synthesis.

When containing the said aromatic hydrocarbon compound in layers other than a light emitting layer, it is preferable to contain 70-100 mass%, and it is more preferable to contain 85-100 mass%. When containing an aromatic hydrocarbon compound in a light emitting layer, it is preferable to contain 0.1-99 mass% with respect to the total mass of a light emitting layer, It is more preferable to contain 1-95 mass%, It is more preferable to contain 10-95 mass% Do.

As said aromatic hydrocarbon compound, it is preferable to use the hydrocarbon compound which consists only of a carbon atom and a hydrogen atom, has a molecular weight in the range of 400-1200, and has a condensed polycyclic skeleton of 13-22 total carbon atoms. Bullets with the condensed polycyclic skeleton of the small number of 13-22 is, fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, triphenylene, and preferably in any of the alkylene to, the point of view of T ₁ In the above, fluorene, triphenylene and phenanthrene are more preferable, triphenylene is more preferable from the viewpoint of stability of the compound, charge injection and transportability, and particularly preferably a compound represented by the following general formula (Tp-1). .

It is preferable that the hydrocarbon compound represented by the said general formula (Tp-1) is the range of the molecular weight 400-1200, More preferably, it is 400-1000, More preferably, it is 400-800. If the molecular weight is 400 or more, a good amorphous thin film can be formed, and if the molecular weight is 1200 or less, it is preferable in view of solubility in solvents, sublimation, and vapor deposition titration.

The use of the hydrocarbon compound represented by the general formula (Tp-1) is not limited, and may be further contained in any layer in the organic layer as well as the organic layer adjacent to the light emitting layer.

[Formula 41]

In General Formula (Tp-1), R ¹² to R ²³ are each independently a hydrogen atom, an alkyl group or an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a phenyl group or fluorenyl group which may be substituted with a triphenylenyl group. , Naphthyl group, or triphenylenyl group. However, all of R ¹² to R ²³ do not become hydrogen atoms.

As an alkyl group which R <^12> -R <^23> represents, a substituent or an unsubstituted methyl group, an ethyl group, isopropyl group, n-butyl group, tert- butyl group, n-octyl group, n-decyl group, n-hexade A real group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned, Preferably they are a methyl group, an ethyl group, an isopropyl group, a tert- butyl group, a cyclohexyl group, More preferably, a methyl group, an ethyl group, or tert -Butyl group.

R ¹² to R ²³ are preferably an alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorenyl group, a naphthyl group or a triphenylenyl group (these are also an alkyl group, a phenyl group, a fluorenyl group or a naphthyl group). Or a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, which may be substituted with a triphenylenyl group.

It is especially preferable that it is a benzene ring which may be substituted by the phenyl group, the fluorenyl group, the naphthyl group, or the triphenylenyl group (These may also be substituted by the alkyl group, the phenyl group, the fluorenyl group, the naphthyl group, or the triphenylenyl group.) .

It is preferable that the total number of the aryl rings in the said general formula (Tp-1) is 2-8, and it is preferable that it is 3-5. By setting it as this range, a high quality amorphous thin film can be formed and the solubility, sublimation, and vapor deposition titration to a solvent become favorable.

It is preferable that total carbon number is 20-50 respectively, and, as for R <^12> -R <^23> , each is more preferable that it is 20-36. By setting it as this range, a high quality amorphous thin film can be formed and the solubility, sublimation, and vapor deposition titration to a solvent become favorable.

It is preferable that the hydrocarbon compound represented by said general formula (Tp-1) is a hydrocarbon compound represented with the following general formula (Tp-2).

[Formula 42]

In General Formula (Tp-2), a plurality of Ar ¹ are the same and may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, a phenyl group, a fluorenyl group, a naphthyl group, or triphenylenyl Group.

Examples of the phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group which may be substituted with an alkyl group and an alkyl group represented by Ar ¹ , an phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group include those mentioned in R ¹² to R ²³ . The same meanings are also preferable.

It is also preferable that the hydrocarbon compound represented by said general formula (Tp-1) is a hydrocarbon compound represented with the following general formula (Tp-3).

[Formula 43]

In General Formula (Tp-3), L is a phenyl group, fluorenyl group, naphthyl group, triphenylenyl group or n formed by combining an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group. Shows a coupling group. n represents the integer of 1-6.

The alkyl group, phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group forming the n-valent linking group represented by L has the same meanings as those listed for R ¹² to R ²³ .

As L, Preferably, it is the benzene ring which may be substituted by the alkyl group or the benzene ring, the fluorene ring, or the n-valent coupling group which combines these.

Although the preferable specific example of L is given to the following, it is not limited to these. In addition, it bonds with a triphenylene ring in * in specific example.

[Formula 44]

It is preferable that it is 1-5, and, as for n, it is more preferable that it is 1-4.

When the hydrocarbon compound represented by the general formula (Tp-1) is used as the host material of the light emitting layer of the organic electroluminescent element or the charge transporting material of the layer adjacent to the light emitting layer, the energy gap in the thin film state (the light emitting material is In the case of the phosphorescent light emitting material, when the lowest triplet excitation (T ₁ ) energy) in the thin film state is large, the light emission is prevented from being quenched, which is advantageous for improving the efficiency. On the other hand, from the viewpoint of chemical stability of the compound, the energy gap and the T ₁ energy are preferably not too large. T ₁ energy of the film state of the hydrocarbon compound represented by formula (Tp-1) is, 1.77 eV (40 ㎉ / ㏖ ) more than 3.51 eV (81 ㎉ / ㏖) is preferably, 2.39 eV (55 ㎉ / ㏖ or less It is more preferable that it is more than or equal to 3.25 eV (75 dl / mol). In the organic electroluminescent device of the present invention, it is preferable that the T ₁ energy of the compound represented by the general formula (Tp-1) is higher than the T ₁ energy of the above-mentioned phosphorescent light emitting material from the viewpoint of luminous efficiency. In particular, when the emission color from the organic electroluminescent element is green (the emission peak wavelength is 490 to 580 nm), the T ₁ energy is 2.39 eV (55 dl / mol) or more and 2.82 eV (65 dl / mol) from the viewpoint of luminescence efficiency. More preferably).

The T ₁ energy of the hydrocarbon compound represented by the general formula (Tp-1) can be obtained by the same method as the method in the description of the general formula (1) described above.

From the viewpoint of operating the organic electroluminescent device stably with respect to heat generation during high temperature driving or driving the device, the glass transition temperature (Tg) of the hydrocarbon compound according to the present invention is preferably 80 ° C or more and 400 ° C or less, It is more preferable that it is below, and it is further more preferable that it is 120 degreeC or more and 400 degrees C or less.

Although the specific example of the said hydrocarbon compound characterized by the said general formula (Tp-1) below is illustrated, the said hydrocarbon compound used for this invention is not limited to these.

[Formula 45]

[Formula 46]

The compound illustrated as a hydrocarbon compound represented by the said general formula (Tp-1) is international publication 05/013388 pamphlet, international publication 06/130598 pamphlet, international publication 09/021107 pamphlet, US2009 / 0009065, international It can synthesize | combine by the method described in the publication 09/008311 pamphlet and international publication 04/018587 pamphlet.

After synthesis, purification by column chromatography, recrystallization or the like is preferably followed by purification by sublimation purification. By sublimation purification, not only an organic impurity can be separated but an inorganic salt, a residual solvent, etc. can be removed effectively.

[Compound represented by general formula (O-1)]

As a material which is particularly preferably used for the material of the organic layer preferably disposed between the cathode (B) and the light emitting layer, it is preferable to use a compound represented by the following general formula (O-1) for the efficiency and driving voltage of the organic electroluminescent element. It is preferable at the point of view. General formula (O-1) is demonstrated below.

[Formula 47]

In General Formula (O-1), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. A ^O1 to A ^O4 each independently represent CR ^A or a nitrogen atom. R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different. L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring or a heteroaryl ring. ^nO1 represents the integer of 2-6.

R <^O1> represents an alkyl group (preferably C1-C8), an aryl group (preferably C6-C30), or heteroaryl group (preferably C4-C12), These represent substituent group A mentioned above You may have it. R ⁰¹ is preferably an aryl group or a heteroaryl group, more preferably an aryl group. As a preferable substituent in the case where the aryl group of R <^O1> has a substituent, an alkyl group, an aryl group, or a cyano group is mentioned, An alkyl group or an aryl group is more preferable, An aryl group is still more preferable. When the aryl group of R ^{O1 has} a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5 or 6 membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent A, more preferably an phenyl group in which an alkyl group or an aryl group may be substituted, and still more preferably an unsubstituted phenyl group or 2-phenylphenyl group.

A ^O1 to A ^O4 each independently represent CR ^A or a nitrogen atom. ^O1 ~ ^O4 A of A, 0 ~ 2 dogs and more preferably it is preferred, and 0 or one is the nitrogen atom of the nitrogen atom. It is more preferred that all of A ^O1 to A ^O4 are CR ^A or A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are CR ^A , A ^O1 is a nitrogen atom, and A ^O2 to A ^O4 are CR ^A It is more preferable that A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are CR ^A , and R ^A is all a hydrogen atom.

R ^A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms), and these substituents Z You may have ' Moreover, some R ^<A> may be same or different. R ^A is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

L <^O1> represents the bivalent to hexavalent coupling group which consists of an aryl ring (preferably C6-C30) or a heteroaryl ring (preferably C4-C12). ^LO1 is preferably an arylene group, a heteroarylene group, an aryltriyl group, or a heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or a benzenetriyl group. L <^O1> may have the substituent Z 'mentioned above, and as a substituent in the case of having a substituent, an alkyl group, an aryl group, or a cyano group is preferable. The following are mentioned as a specific example of L <^O1> .

[Formula 48]

^nO1 represents the integer of 2-6, Preferably it is an integer of 2-4, More preferably, it is 2 or 3. n ^O1 is most preferably 3 from the viewpoint of the efficiency of the organic EL device, and most preferably 2 from the viewpoint of the durability of the organic EL device.

The compound represented by said general formula (O-1), More preferably, it is a compound represented with the following general formula (O-2).

[Formula 49]

In General Formula (O-2), each of R ^{O1 's} independently represents an alkyl group, an aryl group, or a heteroaryl group. R ^O2 to R ^O4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. A ^O1 to A ^O4 each independently represent CR ^A or a nitrogen atom. R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different.

R ^O1 and A ^O1 ~ ^O4 are A, and the general formula (O1) of the R ^O1 and A ^O1 ~ ^O4 same meanings as A, it is also the same from their preferred range.

R ⁰² to R ⁰⁴ each independently represent a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms) These may have a substituent group A mentioned above. R ⁰² to R ⁰⁴ are preferably hydrogen atoms, alkyl groups, or aryl groups, more preferably hydrogen atoms or aryl groups, and most preferably hydrogen atoms.

From the viewpoint of operating the compound represented by the general formula (O-1) stably with respect to stability during high temperature storage and high heat generation during driving at high temperature, the glass transition temperature (Tg) is from 100 ° C to 400 ° C. It is preferable that it is 120 degreeC-400 degreeC, and it is still more preferable that it is 140 degreeC-400 degreeC.

Although the specific example of a compound represented by the said general formula (O-1) is shown below, the compound used for this invention is not limited to these.

[Formula 50]

[Formula 51]

The compound represented by the said general formula (O-1) can be synthesize | combined by the method of Unexamined-Japanese-Patent No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation or the like is preferably followed by purification by sublimation purification. Not only organic impurities can be separated by sublimation purification, but also inorganic salts, residual solvents, water, and the like can be effectively removed.

In the organic electroluminescent element of the present invention, the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but more preferably contained in the layer on the cathode side adjacent to the light emitting layer.

<Protective layer>

In the present invention, the entire organic electroluminescent element may be protected by a protective layer.

About a protective layer, the matter of Paragraph No. [0169]-[0170] of Unexamined-Japanese-Patent No. 2008-270736 can be applied to this invention. In addition, an inorganic material may be sufficient as the material of a protective layer, and an organic material may be sufficient as it.

<Bag container>

The organic electroluminescent element of this invention may seal the whole element using a sealing container.

About the sealing container, the matter described in Paragraph No. [0171] of Unexamined-Japanese-Patent No. 2008-270736 can be applied to this invention.

<Drive method>

In the organic electroluminescent element of the present invention, light emission can be obtained by applying a direct current (may include an alternating current component) voltage (usually 2 volts to 15 volts) or a direct current between the anode and the cathode.

As for the driving method of the organic electroluminescent element of the present invention, JP-A-2-148687, JP-A-6-301355, JP-A 5-29080, JP-A-7- 134558, Japanese Patent Application Laid-Open No. Hei 8-234685, Japanese Patent Application Laid-Open No. Hei 8-241047, the driving method described in each specification of Japanese Patent No. 2784615, US Patent 5828429, US Patent 6023308, etc. can be applied. have.

As external quantum efficiency of the organic electroluminescent element of this invention, 7% or more is preferable and 10% or more is more preferable. As the numerical value of the external quantum efficiency, the maximum value of the external quantum efficiency when the device is driven at 20 ° C or the value of the external quantum efficiency at around 300 to 400 cd / m 2 when the device is driven at 20 ° C can be used.

It is preferable that the internal quantum efficiency of the organic electroluminescent element of this invention is 30% or more, 50% or more is more preferable, and 70% or more is more preferable. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. Although the light extraction efficiency is about 20% in a conventional organic EL device, the light extraction efficiency is considered by considering the shape of the substrate, the shape of the electrode, the film thickness of the organic layer, the film thickness of the inorganic layer, the refractive index of the organic layer, the refractive index of the inorganic layer, and the like. It is possible to make 20% or more.

<Light emission wavelength>

The organic electroluminescent element of the present invention is not limited in its emission wavelength. For example, the three primary colors of light may be used for emitting red light, may be used for emitting green light, or may be used for emitting blue light. Of these, the organic EL device of the present invention, it is preferable that the emission peak wavelength of 490 ~ 580 ㎚ preferable in terms of light emission efficiency in consideration of the above general formula (1) where the minimum of the compound represented by the triplet (T ₁₎ Energy .

Specifically, in the organic electroluminescent device of the present invention, when the compound represented by the general formula (1) is used as the host material of the light emitting layer, the electron transporting layer, or the electron transporting material of the hole block layer, the emission peak wavelength is 490. It is preferable that it is -580 nm, It is more preferable that it is 490-550 nm, It is especially preferable that it is 500-535 nm.

<Use of organic electroluminescent device of the present invention>

The organic electroluminescent element of this invention can be used suitably for a display element, a display, a backlight, an electrophotographic, an illumination light source, a recording light source, an exposure light source, a reading light source, a cover, a sign, interior, or optical communication. In particular, it is used suitably for the device driven in the area | region where light emission brightness is high, such as a light emitting device, a lighting device, and a display device.

[Light emitting device]

The light emitting device of the present invention includes the organic electroluminescent element of the present invention.

Next, the light emitting device of the present invention will be described with reference to FIG.

2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention. The light emitting device 20 of FIG. 2 is comprised by the transparent substrate (support substrate) 2, the organic electroluminescent element 10, the sealing container 16, etc. In FIG.

The organic electroluminescent element 10 is configured by sequentially stacking an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2. Moreover, the protective layer 12 is laminated | stacked on the cathode 9, and the sealing container 16 is formed on the protective layer 12 via the contact bonding layer 14. As shown in FIG. In addition, a part of each electrode 3, 9, a partition, an insulation layer, and the like are omitted.

Here, as the adhesive layer 14, photocurable adhesives, such as an epoxy resin, and a thermosetting adhesive can be used, for example, a thermosetting adhesive sheet can also be used.

The use of the light emitting device of the present invention is not particularly limited. For example, the light emitting device may be a display device such as a television, a personal computer, a mobile phone, or an electronic paper, in addition to a lighting device.

[Lighting device]

The illuminating device of this invention is characterized by including the organic electroluminescent element of this invention.

Next, the lighting apparatus of this invention is demonstrated with reference to FIG.

3 is a cross-sectional view schematically showing an example of the lighting apparatus of the present invention. As shown in FIG. 3, the lighting device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting apparatus 40 is comprised so that the board | substrate 2 of the organic electroluminescent element 10 and the light scattering member 30 may contact.

The light scattering member 30 is not particularly limited as long as it can scatter light, but in FIG. 3, the light scattering member 30 is a member in which the fine particles 32 are dispersed in the transparent substrate 31. As the transparent substrate 31, a glass substrate is mentioned preferably, for example. As the microparticles | fine-particles 32, transparent resin microparticles | fine-particles are mentioned preferably. As the glass substrate and the transparent resin fine particles, known ones can be used. When the light emission from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the lighting device 40 scatters the incident light by the light scattering member 30, and scatters the light. The light is emitted from the light exit surface 30B as illumination light.

[Display device]

The display device of the present invention includes the organic electroluminescent element of the present invention.

As a display apparatus of this invention, what is used as display apparatuses, such as a television, a personal computer, a mobile telephone, and electronic paper, etc. are mentioned, for example.

Example

An Example is given to the following and this invention is demonstrated to it further more concretely. The materials, usage amounts, ratios, treatment contents, treatment procedures, and the like shown in the following examples can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific example shown below.

[Examples 1-6]

1. Synthesis of Compound Represented by the General Formula (1) (Synthesis of Compound 1B-2)

[Formula 52]

According to the above scheme, compound 1B-2 was synthesized by repeating Suzuki-Miyaura coupling.

Compounds 1B-3, 1B-4, 1B-17, 1D-1, and 1D-3, which are compounds represented by the general formula (1), were synthesized by the same Suzuki-Miyaura coupling as that of the compound 1B-2. .

Embodiments shown in Examples 1 to 6 to a ¹ H-NMR data of the compound 1B-2, 1B-3, 1B-4, 1B-17, 1D-1, 1D-3 synthesized in the Figs. 4 to 9, respectively.

[Formula 53]

Details of the ¹ H-NMR data of the compounds 1B-2, 1B-3, 1B-4, 1B-17, 1D-1, and 1D-3 which are read from FIGS. 4 to 9 are shown below.

Compound 1b-2

¹ H-NMR (solvent): medium DMSO, reference: tetramethylsilane) δ (ppm)

Compound 1b-3

¹ H-NMR (solvent): medium CDCl ₃ , standard: tetramethylsilane) δ (ppm)

Compound 1b-4

¹ H-NMR (solvent): medium CDCl ₃ , standard: tetramethylsilane) δ (ppm)

Compound 1b-17

¹ H-NMR (solvent): medium CDCl ₃ , standard: tetramethylsilane) δ (ppm)

Compound 1d-1

¹ H-NMR (solvent): medium CDCl ₃ , standard: tetramethylsilane) δ (ppm)

Compound 1d-3

¹ H-NMR (solvent): medium CDCl ₃ , standard: tetramethylsilane) δ (ppm)

Then, the compound represented by the said General formula (1) used for manufacture of the organic electroluminescent element mentioned later and the comparative compound 1-4 in which some structures are similar to it are synthesize | combined similarly to the said compound 1B-2.

2. Fabrication and Evaluation of Organic Electroluminescent Devices

(2-A) Fabrication of an organic EL device of green phosphorescence-1

Sublimation purification was performed in advance with respect to the material used for organic electroluminescent element manufacture.

Comparative Example 1

(Manufacture of Anode)

A glass substrate having a thickness of 0.5 mm and a width of 2.5 cm in length and an ITO film (manufactured by Geotech Co., Ltd., surface resistance of 10 Ω / square) was placed in a washing container, ultrasonically cleaned in 2-propanol, and subjected to UV-ozone treatment for 30 minutes. .

This was used as an anode (ITO film, transparent anode).

(Lamination of Organic Layer)

The organic compound of the 1st-5th layers was sequentially deposited on the said anode using the following compounds by the vacuum vapor deposition method. In addition, the structure of the compound used for each layer was shown.

First layer: LG101: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

Third layer: Comparative compound 1 (host material) and green phosphorescent material GD-1 (guest material) (mass ratio 90:10): film thickness 30 nm

Fourth layer: TpH-17: film thickness 10 nm

5th layer: Alq: film thickness 40 nm

[Formula 54]

(Production of a cathode)

On this, 0.1 nm of lithium fluoride and 200 nm of metallic aluminum were deposited in this order to make a cathode.

(Production of Organic Electroluminescence)

A laminated body having five organic layers between the cathode and the anode was placed in a glove box substituted with nitrogen gas without being brought into contact with the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Chiba Co., Ltd.) were prepared. It sealed using and obtained the organic electroluminescent element of the comparative example 1.

(Evaluation of Organic Electroluminescent Element)

(a) durability

The organic electroluminescent element of Comparative Example 1 was continuously lighted by applying a direct current voltage such that the luminance became 5000 cd / m 2 at room temperature, and the time required until the luminance became 4000 cd / m 2 was measured. This time was used as an index of durability of the organic EL device.

In addition, in each Example and comparative example mentioned later, in Table 1 described below, durability when the organic electroluminescent element of Comparative Example 1 was used was 100, and the relative value of durability is less than 100 × 100 The thing below 150 was made into (circle) and the thing of 150 or more as ◎.

Here, durability is so preferable that a number is large.

(b) chromaticity difference after high temperature storage

A direct current voltage was applied to the organic electroluminescent device of Comparative Example 1 after high temperature storage (48 hours at 100 ° C.) and before storage, and the emission spectrum measuring system manufactured by Shimadzu Corporation The emission spectrum was measured by ELS 1500), and chromaticity (CIE chromaticity) was calculated.

The chromaticity after high temperature storage (48 hours at 100 ° C) differs by at least 0.01 from the x coordinate or the y coordinate before storage and at the CIE (x, y) coordinates. Was taken as ◎.

(c) glass transition temperature

The glass transition temperature of the comparative compound 1 used as a host material in the 3rd layer of the organic layer was measured by differential scanning calorimetry (DSC).

The result is shown in following Table 1 as a thing whose glass transition temperature Tg is less than 100 degreeC x and what is 100 degreeC or more and less than 120 degreeC as (circle) and 120 degreeC or more.

[Examples A1 to A9 and Comparative Examples 2 to 4]

As a material of the 3rd layer of the organic layer in the comparative example 1, it carried out similarly to the comparative example 1 except having used the compound represented by the said General formula (1) shown in following Table 1, or the comparative compounds 2-4 instead of the comparative compound 1. Thus, the organic electroluminescent elements of Examples A1 to A9 and Comparative Examples 2 to 4 were obtained.

In addition, Comparative Compound 1 is Compound compound 2S described in International Publication WO2009 / 073245, Comparative Compound 3 is Compound compound 2S described in International Publication WO2009 / 021126, and Comparative Compound 4 is Compound Compound described in International Publication WO2009 / 021126. 9S.

[Formula 55]

These organic electroluminescent elements were evaluated in the same manner as in Comparative Compound 1. The results are shown in Table 1 below.

From the said Table 1, it turned out that the organic electroluminescent element of each Example which used the compound represented by General formula (1) of Examples A1-A9 as a host compound of a light emitting layer has the favorable durability and chromaticity difference after high temperature storage. . Moreover, the compound represented by General formula (1) of these Examples A1-A9 was favorable for high glass transition temperature.

On the other hand, the organic electroluminescent elements of Comparative Examples 1, 2, and 4 used Comparative Compounds 1, 2, and 4 as host compounds of the light emitting layer, and it was found that durability was poor. As for the organic electroluminescent element of the comparative example 3, the comparative compound 3 was used as a host compound of a light emitting layer, and it turned out that the chromaticity difference after high temperature storage is bad. Moreover, the comparative compounds 1-3 used in Comparative Examples 1-3 were low in glass transition temperature.

In addition, the peak emission wavelength of the organic electroluminescent element manufactured in Examples A1-A9 was 515-535 nm.

(2-B) Fabrication of an organic EL device of green phosphorescence emission-2

[Comparative Example 5]

The organic layer of the organic electroluminescent device of Comparative Example 1 was prepared in the same manner as in Comparative Example 1 except that NPD used in the second layer was replaced by HTL-1, and GD-1 used in the third layer was replaced by GD-2. Thus, the organic electroluminescent device of Comparative Example 5 was obtained. The structure of the organic layer in the comparative example 5 is shown below.

First layer: LG101: film thickness 10 nm

Second layer: HTL-1: film thickness 30 nm

Third layer: comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90: 10): film thickness 30 nm

Fourth layer: TpH-17: film thickness 10 nm

5th layer: Alq: film thickness 40 nm

[Formula 56]

[Examples B1 to B4, Comparative Example 6]

Except having used the compound represented by General formula (1) and the comparative compound 3 instead of the comparative compound 1 as a material of the 3rd layer of the organic layer in the comparative example 5, it carried out similarly to the comparative example 5, and compares Examples B1-B4 and The organic electroluminescent element of Example 6 was obtained.

The organic electroluminescent elements of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability at the time of using the organic electroluminescent element of Comparative Example 5 as 100 as an evaluation criteria of durability, and the relative value of the durability of the organic electroluminescent element of each other Example and a comparative example is less than 100 × 100 or more The thing less than 150 was evaluated as (circle) and the thing more than 150 as (circle).

The results are shown in Table 2 below.

From the said Table 2, it turned out that the organic electroluminescent element of each Example which used the compound represented by General formula (1) of Examples B1-B6 as a host compound of a light emitting layer has the favorable durability and chromaticity difference after high temperature storage. .

On the other hand, the organic electroluminescent element of the comparative example 5 used the comparative compound 1 as a host compound of a light emitting layer, and it turned out that durability is bad. In the organic electroluminescent device of Comparative Example 6, Comparative Compound 3 was used as the host compound of the light emitting layer, and it was found that the chromaticity difference after high temperature storage was poor.

In addition, the light emission wavelength of the organic electroluminescent element manufactured in Examples B1-B6 was 510-525 nm.

(2-C) Fabrication of organic electroluminescent device of red phosphorescence

Comparative Example 7

For the organic layer of the organic electroluminescent device of Comparative Example 1, the LG101 used for the first layer was replaced with GD-1, and the GD-1 used for the third layer was replaced with the red phosphorescent light emitting material RD-1, and the fourth layer. An organic electroluminescent device of Comparative Example 7 was manufactured in the same manner as in Comparative Example 1 except that TpH-17 used for was replaced with Alq. The structure of the organic layer in the comparative example 7 is shown below.

First layer: GD-1: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

Third layer: Comparative compound 1 (host material) and red phosphorescent material RD-1 (guest material) (mass ratio 90: 10): film thickness 30 nm

Fourth layer: Alq: film thickness 10 nm

5th layer: Alq: film thickness 40 nm

[Formula 57]

[Examples C1 to C3, Comparative Example 8]

Except having used the compound represented by General formula (1) and the comparative compound 3 instead of the comparative compound 1 as a material of the 3rd layer of the organic layer in the comparative example 7, it carried out similarly to the comparative example 7, Example C1-C6, and An organic electroluminescent device of Comparative Example 8 was obtained.

The organic electroluminescent elements of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability at the time of using the organic electroluminescent element of Comparative Example 7 as 100 as an evaluation criteria of durability, and the relative value of the durability of the organic electroluminescent element of each other Example and a comparative example is less than 100 × 100 or more. The thing less than 150 was evaluated as (circle) and the thing more than 150 as (circle).

The results are shown in Table 3 below.

From the said Table 3, it turned out that the organic electroluminescent element of each Example which used the compound represented by General formula (1) of Examples C1-C3 as a host compound of a light emitting layer has the favorable durability and chromaticity difference after high temperature storage all. .

On the other hand, the organic electroluminescent element of the comparative example 7 used the comparative compound 1 as a host compound of a light emitting layer, and it turned out that durability is bad. In the organic electroluminescent device of Comparative Example 8, Comparative Compound 3 was used as the host compound of the light emitting layer, and it was found that the chromaticity difference after high temperature storage was poor.

In addition, the light emission wavelength of the organic electroluminescent element manufactured in Examples C1-C3 was 615-630 nm.

(2-D) Fabrication of an organic EL device of green phosphorescence emission-3

Comparative Example 9

A device of Comparative Example 9 was prepared in the same manner as in Comparative Example 5 except that TpH-17 used for the fourth layer of the device of Comparative Example 5 was replaced with OM-8 for OM-8 and Alq used for the fifth layer. . The structure of the organic layer in the comparative example 9 is shown below.

First layer: LG101: film thickness 10 nm

Second layer: HTL-1: film thickness 30 nm

Third layer: comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90: 10): film thickness 30 nm

Fourth layer: OM-8: film thickness 10 nm

Fifth layer: OM-8: film thickness 40 nm

[Formula 58]

[Examples D1 to D5, Comparative Example 10]

Except having used the compound represented by General formula (1) and the comparative compound 3 instead of the comparative compound 1 as a material of the 3rd layer of the organic layer in the comparative example 9, Example D1-D5 and The organic electroluminescent device of Comparative Example 10 was obtained.

These devices were evaluated in the same manner as in Comparative Example 1.

The organic electroluminescent elements of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability at the time of using the organic electroluminescent element of Comparative Example 9 as 100 as an evaluation criteria of durability, and the relative value of the durability of the organic electroluminescent element of each other Example and a comparative example is less than 100 × 100 or more. The thing less than 150 was evaluated as (circle) and the thing more than 150 as (circle).

The results are shown in Table 4 below.

From the said Table 4, it turned out that the organic electroluminescent element of each Example which used the compound represented by General formula (1) of Examples D1-D5 as a host compound of a light emitting layer has the favorable durability and chromaticity difference after high temperature storage. .

On the other hand, the organic electroluminescent element of Comparative Example 9 used Comparative Compound 1 as the host compound of the light emitting layer, and it was found that durability was poor. In the organic electroluminescent device of Comparative Example 10, Comparative Compound 3 was used as the host compound of the light emitting layer, and it was found that the chromaticity difference after high temperature storage was poor.

In addition, the light emission wavelength of the organic electroluminescent element manufactured in Examples D1-D5 was 510-525 nm.

(2-E) Fabrication of Green Phosphorescent Organic Electroluminescent Device-4

(Comparative Example 11)

The device of Comparative Example 11 was prepared in the same manner as in Comparative Example 4 except that TpH-17 used in the fourth layer of the device of Comparative Example 5 was replaced with OM-8 for Alq used in Comparative Compound 1 and the fifth layer. . The structure of the organic layer in the comparative example 11 is shown below.

First layer: LG101: film thickness 10 nm

Second layer: HTL-1: film thickness 30 nm

Third layer: comparative compound 1 (host material) and green phosphorescent material GD-2 (guest material) (mass ratio 90: 10): film thickness 30 nm

Fourth layer: comparative compound 1: film thickness 10 nm

Fifth layer: OM-8: film thickness 40 nm

[Formula 59]

[Examples E1 to E3, Comparative Example 12]

As a material of the third layer of the organic layer in Comparative Example 11, a compound represented by the general formula (1) or Comparative Compound 3 is used instead of Comparative Compound 1, and as a material of the fourth layer of the organic layer, Except having used the compound represented by Formula (1) or the comparative compound 3, it carried out similarly to the comparative example 11, and obtained the organic electroluminescent element of Examples E1-E3 and Comparative Example 12.

The organic electroluminescent elements of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability at the time of using the organic electroluminescent element of the comparative example 11 as 100 as an evaluation criteria of durability, and the relative value of the durability of the organic electroluminescent element of each other Example and a comparative example is less than 100 × 100 or more. The thing less than 150 was evaluated as (circle) and the thing more than 150 as (circle).

The results are shown in Table 5 below.

From the above Table 5, the organic electroluminescent elements of each Example using the compound represented by General formula (1) of Examples E1 to E3 as the host compound of the light emitting layer and the organic layer 4th layer are all excellent in durability and chromaticity difference after high temperature storage. I could see that.

On the other hand, the organic electroluminescent element of Comparative Example 11 used Comparative Compound 1 as the host compound and the organic layer fourth layer of the light emitting layer, and it was found that durability was poor. In the organic electroluminescent device of Comparative Example 12, Comparative Compound 3 was used as the host compound and the organic layer fourth layer of the light emitting layer, and it was found that the chromaticity difference after high temperature storage was poor.

In addition, the light emission wavelength of the organic electroluminescent element manufactured in Examples E1-E3 was 510-525 nm.

2 … Board
3…. anode
4 … Hole injection layer
5... Hole transport layer
6. Light emitting layer
7. Hole block layer
8 … Electron transport layer
9. cathode
10... Organic EL device (Organic EL device)
11. Organic layer
12... Protective layer
14. Adhesive layer
16. Bag containers
20... Light emitting device
30. Light scattering member
30A. Light incident surface
30B. Light exit surface
31. Transparent substrate
32. Particulate
40…. Lighting device

Claims (14)

Substrate,
A pair of electrodes disposed on the substrate and including an anode and a cathode;
Having an organic layer disposed between the electrodes,
The organic layer includes a phosphorescent material and a compound represented by the following general formula (1), as an organic electroluminescent device,
An organic electroluminescent device in which the compound of the following general formulas (2) to (11) is excluded from the compound represented by the general formula (1):
General formula (1)

In General Formula (1), X ¹⁰¹ represents a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (excluding an alkyl group, an amino group and a cyano group), and a plurality of R ¹⁰⁸ to R ¹¹⁰ represent each other. May be the same or different and L ¹⁰¹ represents a single bond or an arylene group;
General formula (2)

In General Formula (2), X ²⁰¹ represents a sulfur atom, R ²⁰¹ to R ²¹² each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ²⁰⁸ and R ²⁰⁹ may be the same as or different from each other. , L ²⁰¹ represents a single bond or an arylene group, and is not a p-terphenylene group, and one of A ²⁰¹ and A ²⁰² is an aryl group having 10 to 30 ring atoms as the condensed ring and 8 to 30 ring atoms as the condensed ring Heteroaryl group having 5 to 25 ring atoms having a aryl group having 6 to 25 carbon atoms as a substituent or a heteroaryl group having 5 to 25 ring atoms or a aryl group having 6 to 25 carbon atoms as a substituent Heteroaryl group; the other one represents a hydrogen atom, an aryl group, or a heteroaryl group;
General formula (3)

In General Formula (3), X ³⁰¹ represents a sulfur atom, R ³⁰¹ to R ³¹⁵ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ³⁰⁸ to R ³¹² may be the same as or different from each other. , L ³⁰¹ represents a single bond or an arylene group, one of A ³⁰¹ and A ³⁰² is an aryl group having 10 to 30 ring atoms as a condensed ring, a heteroaryl group having 8 to 30 ring atoms as a condensed ring, and these as substituents A aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms, or a aryl group having 6 to 25 carbon atoms as a substituent, and a 5 to 25 monocyclic heteroaryl group having 1 to 25 ring atoms, and the other A hydrogen atom, an aryl group or a heteroaryl group;

In General Formula (4), X ⁴⁰¹ and X ⁴⁰² each independently represent a sulfur atom, R ⁴⁰¹ to R ⁴¹⁷ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁴⁰⁸ to R ⁴¹⁰ are each other May be the same or different and n ₄₀₁ represents 0 or 1;

In General Formula (5), X ⁵⁰¹ represents a sulfur atom, R ⁵⁰¹ to R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁵⁰⁸ to R ⁵¹³ may be the same as or different from each other. , n ₅₀₁ represents 0 or 1;

In General Formula (6), X ⁶⁰¹ and X ⁶⁰² each independently represent a sulfur atom, R ⁶⁰¹ to R ⁶²⁰ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁶⁰⁸ to R ⁶¹³ are each other May be the same or different;

In General Formula (7), X ⁷⁰¹ represents a sulfur atom, R ⁷⁰¹ to R ⁷¹⁶ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁷⁰⁸ to R ⁷¹⁶ may be the same as or different from each other. ;

In General Formulas (8) to (11), X ⁸⁰¹ to X ⁸⁰⁶ each independently represent a sulfur atom, R ⁸⁰¹ to R ⁸⁰⁶ each independently represent a hydrogen atom or an aryl group having 6 to 13 carbon atoms, and A ¹¹ to A ¹³ each independently represents CH or a nitrogen atom, and at least one is a nitrogen atom. The method of claim 1,
An organic electroluminescent device, characterized in that the molecular weight of the compound is 550 or more. The method of claim 1,
An organic electroluminescent device, wherein the compound is a compound having a glass transition temperature of 100 ° C. or higher. The method of claim 1,
Wherein the phosphorescent material is an iridium (Ir) complex represented by the following general formula (E-1):

In General Formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom, and A ₁ represents an atomic group that forms a heterocyclic ring of 5 or 6 atoms with Z ¹ and a nitrogen atom; , B ₁ represents an atomic group which forms a 5 or 6 membered ring together with Z ² and a carbon atom, (XY) represents a monoanionic bidentate ligand, and n _E1 represents an integer of 1 to 3. The method of claim 4, wherein
The iridium (Ir) complex represented by said general formula (E-1) is represented by the following general formula (E-2), The organic electroluminescent element characterized by the above-mentioned:

In the general formula ^{(E-2), A E1} ~ A E8 each independently represents a substituted carbon atom by a nitrogen atom, or R ^E, R ^E represents a hydrogen atom or a substituent, (XY) is a mono anionic A 2 left ligand is represented and n _E2 represents the integer of 1-3. The method of claim 1,
The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The organic light emitting device according to claim 1, wherein the light emitting layer contains the compound. The method of claim 1,
The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
Another organic layer is disposed between the light emitting layer and the cathode, is adjacent to the light emitting layer, and contains the compound. The method of claim 1,
Having an electron transporting layer adjacent to the cathode between the pair of electrodes,
And optionally has a hole block layer adjacent to the opposite side of the cathode of the electron transport layer,
The electron transport layer or the hole block layer contains the compound. The method of claim 1,
And an organic layer disposed between the pair of electrodes comprises a layer formed by deposition of a composition containing at least one layer of the compound. The method of claim 1,
An emission peak wavelength is 490-580 nm, The organic electroluminescent element characterized by the above-mentioned. A light emitting device, lighting device or display device comprising the organic electroluminescent element according to any one of claims 1 to 10. As a compound represented by the following general formula (1), the compound of which the compound of the following general formula (2)-(11) was excluded from the compound represented by the said general formula (1):
General formula (1)

In General Formula (1), X ¹⁰¹ represents a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (excluding an alkyl group, an amino group and a cyano group), and a plurality of R ¹⁰⁸ to R ¹¹⁰ represent each other. May be the same or different and L ¹⁰¹ represents a single bond or an arylene group;
General formula (2)

In General Formula (2), X ²⁰¹ represents a sulfur atom, R ²⁰¹ to R ²¹² each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ²⁰⁸ and R ²⁰⁹ may be the same as or different from each other. , L ²⁰¹ represents a single bond or an arylene group, and is not a p-terphenylene group, and one of A ²⁰¹ and A ²⁰² is an aryl group having 10 to 30 ring atoms as the condensed ring and 8 to 30 ring atoms as the condensed ring Heteroaryl group having 5 to 25 ring atoms having a aryl group having 6 to 25 carbon atoms as a substituent or a heteroaryl group having 5 to 25 ring atoms or a aryl group having 6 to 25 carbon atoms as a substituent Heteroaryl group; the other one represents a hydrogen atom, an aryl group, or a heteroaryl group;
General formula (3)

In General Formula (3), X ³⁰¹ represents a sulfur atom, R ³⁰¹ to R ³¹⁵ each independently represent a hydrogen atom, an aryl group, or a heteroaryl group, and a plurality of R ³⁰⁸ to R ³¹² may be the same as or different from each other. , L ³⁰¹ represents a single bond or an arylene group, one of A ³⁰¹ and A ³⁰² is an aryl group having 10 to 30 ring atoms as a condensed ring, a heteroaryl group having 8 to 30 ring atoms as a condensed ring, and these as substituents A aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms, or a aryl group having 6 to 25 carbon atoms as a substituent, and a 5 to 25 monocyclic heteroaryl group having 1 to 25 ring atoms, and the other A hydrogen atom, an aryl group or a heteroaryl group;

In General Formula (4), X ⁴⁰¹ and X ⁴⁰² each independently represent a sulfur atom, R ⁴⁰¹ to R ⁴¹⁷ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁴⁰⁸ to R ⁴¹⁰ are each other May be the same or different and n ₄₀₁ represents 0 or 1;

In General Formula (5), X ⁵⁰¹ represents a sulfur atom, R ⁵⁰¹ to R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁵⁰⁸ to R ⁵¹³ may be the same as or different from each other. , n ₅₀₁ represents 0 or 1;

In General Formula (6), X ⁶⁰¹ and X ⁶⁰² each independently represent a sulfur atom, R ⁶⁰¹ to R ⁶²⁰ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁶⁰⁸ to R ⁶¹³ are each other May be the same or different;

In General Formula (7), X ⁷⁰¹ represents a sulfur atom, R ⁷⁰¹ to R ⁷¹⁶ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁷⁰⁸ to R ⁷¹⁶ may be the same as or different from each other. ;

In General Formulas (8) to (11), X ⁸⁰¹ to X ⁸⁰⁶ each independently represent a sulfur atom, R ⁸⁰¹ to R ⁸⁰⁶ each independently represent a hydrogen atom or an aryl group having 6 to 13 carbon atoms, and A ¹¹ to A ¹³ each independently represents CH or a nitrogen atom, and at least one is a nitrogen atom. The method of claim 12,
The compound has a molecular weight of 550 or more. The method of claim 12,
The compound is a compound, characterized in that the glass transition temperature is a compound of 100 ℃ or more.

Images