KR20210122322A - 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

Organic electroluminescence comprising 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 contains a phosphorescent material and a compound represented by the following formula The device has excellent durability and a small difference in chromaticity when stored at high temperatures (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). , and 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

An organic electroluminescent device, and a light emitting device, a display device, a lighting device, and a compound for the device using the device TECHNICAL FIELD , AND COMPOUND FOR ORGANIC ELECTROLUMINESCENT ELEMENT}

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

BACKGROUND ART An organic electroluminescent device (hereinafter, also referred to as “element” or “organic EL device”) is being actively researched and developed because high-luminance light emission is obtained by low-voltage driving. An organic electroluminescent device has an organic layer between a pair of electrodes, and the energy of excitons generated by recombination of electrons injected from a cathode and holes injected from an anode in the organic layer is used for light emission.

In recent years, efficiency improvement of organic electroluminescent elements is progressing by using a phosphorescent light emitting material. However, improvement is demanded from the viewpoint of durability and the like at the time of practical use. In order to further improve the luminous efficiency of the device and the device durability, the use of a dibenzothiophene-based charge transport material is described in Patent Document 1. Moreover, the organic electroluminescent element which used the compound which connected dibenzothiophene and triphenylene with the phenyl group is described in patent document 2. Moreover, the organic electroluminescent element which used the compound which connected dibenzothiophene with the phenyl group is described in patent documents 3 and 4.

On the other hand, in recent years, various display devices including organic electroluminescent devices have been widely used, and stable long-term operation under various environments is required. For example, in in-vehicle applications for automobiles, in addition to the requirement for a long service life (so-called durability), the inside of the vehicle becomes very hot during driving or parking during the day, so the characteristics do not change even after high-temperature storage. is also required. In addition, it is important that organic electroluminescent devices do not change their characteristics after storage at such a high temperature from the viewpoint of generating heat during driving to the same level or higher than that of conventional light emitting devices.

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

On the other hand, as a result of the present inventors examining the characteristics of the organic electroluminescent device described in Patent Documents 1 to 4, in addition to still dissatisfied with durability in the conventional organic electroluminescent device, the problem that the chromaticity changes when stored at a high temperature It turned out that there is

Therefore, as a result of changing the compound used for the organic layer, it was found that the durability and the chromaticity difference at the time of storage at a high temperature change to some extent. Therefore, as a result of further research on the compound used in the organic layer, it was found that simply increasing the molecular weight of the compound used in the organic layer does not necessarily improve durability or color difference during high temperature storage. For example, the compound 9S described in Patent Document 2 showed a better chromaticity difference when stored at a high temperature compared to compuond 2S having a smaller molecular weight and a smaller glass transition temperature than this compound, but had poor durability. That is, it was found that it is difficult to improve both durability and chromaticity difference during high temperature storage by changing the compound used in the organic layer.

The problem to be solved by the present invention is to provide an organic electroluminescent device having excellent durability and a small difference in chromaticity when stored at a high temperature.

As a result of intensive studies by the present inventors, by using a compound containing a dibenzothiophene structure or a dibenzofuran structure and a p-terphenylene structure, the organic electroluminescence has excellent durability and a small difference in chromaticity when stored at high temperatures. A device was found to be provided.

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

[1] having 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 a phosphorescent light emitting material and represented by the following general formula (1) An organic electroluminescent device comprising a compound.

General formula (1)

[Formula 1]

(In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (however, an alkyl group and a cyano group are excluded), and 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.)

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

[3] In the general formula (1), at least one R ¹¹⁰ is a condensed ring, an aryl group having 10 to 30 ring atoms, a condensed ring, a heteroaryl group having 8 to 30 ring atoms, and the number of carbon atoms having these as a substituent [1] characterized in that it is a monocyclic heteroaryl group having 5 to 25 ring atoms having as a substituent a 6 to 25 aryl group, a 5 to 25 heteroaryl group, or a monocyclic aryl group having 6 to 25 ring atoms as a substituent [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 the 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 a condensed ring, an aryl group having 10 to 30 ring atoms, or a condensed ring, a ring atom. A heteroaryl group having 8 to 30 atoms, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms having these as a substituent, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent has 5 to 5 ring atoms as a substituent 25 represents a monocyclic heteroaryl group, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.)

general formula (3)

[Formula 3]

(In the 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 a condensed ring, an aryl group having 10 to 30 ring atoms, or a condensed ring, a heteroaryl group having 8 to 30 ring atoms. , an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms having these as a substituent, or a monocyclic heteroaryl group having 5 to 25 ring atoms having as a substituent a monocyclic aryl group having 6 to 25 carbon atoms as a substituent; , 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 R 108} and R ¹⁰⁹ in the general formula (1) are both hydrogen atoms.

[6] The organic electroluminescent device according to any one of [1] to [5], wherein the compound represented by the 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 the general formula (1) is a compound represented by any of the following general formulas (4) to (7).

[Formula 4]

(In the 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.)

[Formula 5]

(In the 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 ⁴¹³ may be the same as each other. and may be different. n ₅₀₁ represents 0 or 1.)

[Formula 6]

(In the 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 the 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. and 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]

(In the general formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom. A ₁ represents an atom group that together with Z ¹ and a nitrogen atom forms a 5- or 6-membered heterocycle; B ₁ represents a group of atoms 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 the 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 represents a bidentate ligand of n _E2 represents an integer of 1 to 3.)

[10] Any one of [1] to [9], wherein the organic layer has a light-emitting layer containing the phosphorescent material and other organic layers, and the light-emitting layer contains a compound represented by the general formula (1). The organic electroluminescent device according to claim.

[11] The organic layer has a light-emitting layer containing the phosphorescent material and other organic layers, and the other organic layer is disposed between the light-emitting layer and the cathode, adjacent to the light-emitting layer, and is represented by the above general formula (1) The organic electroluminescent device according to any one of [1] to [10], characterized in that it contains the compound shown.

[12] an electron transport layer adjacent to the cathode between the pair of electrodes, and optionally a hole blocking layer adjacent to the opposite side of the cathode in the electron transport layer, wherein the electron transport layer or the hole blocking layer is the general The organic electroluminescent element in any one of [1]-[11] characterized by containing the compound represented by Formula (1).

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

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

[15] A light-emitting device, a lighting device, or a display device comprising the organic electroluminescent device 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 the general formulas (8) to (11), X ⁸⁰¹ to X ⁸⁰⁶ each independently represents an oxygen atom or a sulfur atom, and R ⁸⁰¹ to R ⁸⁰⁶ each independently represents 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.)

ADVANTAGE OF THE INVENTION According to this invention, it is excellent in durability and can provide the organic electroluminescent element with a small chromaticity difference at the time of high temperature storage.

Further, according to the present invention, a compound useful for an organic electroluminescent device can be provided as a charge transport material or a host material for a light emitting layer, and a light emitting device, a display device and a lighting device using the organic electroluminescent device can be provided. have.

BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic diagram which shows an example of the structure of the organic electroluminescent element which concerns on this invention.
Fig. 2 is a schematic diagram showing an example of a light emitting device according to the present invention.
3 is a schematic diagram showing an example of a lighting device 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 diagram of compound 1D-1 of the present invention.
^{9 is a 1} H-NMR spectrum diagram of compound 1D-3 of the present invention.

Hereinafter, the content of the present invention will be described in detail. Although the description of the components described below may be made based on the representative embodiment of this invention, this invention is not limited to such an embodiment. In addition, in this specification, "-" is used in the meaning including the numerical value described before and after that as a lower limit and an upper limit.

[Organic electroluminescent 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 comprises a phosphorescent material and the following general It is characterized by containing the compound represented by Formula (1).

General formula (1)

[Formula 11]

(In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (however, an alkyl group and a cyano group are excluded), and 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).

In the organic electroluminescent device, electrons are injected from the cathode and holes are injected from the anode, and they recombine in the organic layer (functionally, it is sometimes referred to as a light emitting layer) while moving on organic molecules. The light emitting material emits light using the excitation energy generated at that time. Then, when the lifetime (durability) of an organic electroluminescent element is considered, the stability of a material is important. In particular, since the electric charges (electrons or holes) move through the material phase, the stability of the material to the electric charge (= stability in the radical state) is very important. Without being bound by any theory, in the present invention, it was found that by using a compound having a p-terphenyl structure, the spin density distribution in a radical state can be delocalized more widely than other phenyl groups or biphenyl groups. Here, as the spin density distribution spreads, the radical species is thermodynamically stabilized. For this reason, it is thought that the dibenzothiophene or dibenzofuran derivative provided with a p-terphenyl structure can ensure high stability in a radical state. As a result, it is thought that the durability of an organic electroluminescent element was able to be improved remarkably. In addition, since the compound introduced with the p-terphenyl structure has fewer movable sites, for example, compared to the case of the m-terphenyl structure, it is possible to prevent a change in the film quality of the organic layer at high temperature, so the high temperature of the organic electroluminescent device It is thought that the color and the difference after storage were able to be made small.

The configuration of the organic electroluminescent device of the present invention is not particularly limited. An example of the 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).

About the element structure of an organic electroluminescent element, a board|substrate, a cathode, and an anode, it describes in detail in Unexamined-Japanese-Patent No. 2008-270736, for example, The matter described in the publication is applicable 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, light emission wavelength, and a use.

<substrate>

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

It is preferable that the board|substrate used by this invention is a board|substrate which does not scatter or attenuate the light emitted from an organic layer. 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 electrodes containing an anode and a cathode.

In view of the properties of the light emitting element, it is preferable that at least one of the anode and the cathode as a pair of electrodes is transparent or translucent.

(anode)

The anode should normally have a function as an electrode for supplying holes to the organic layer, and the shape, structure, size, etc. are not particularly limited, and may be appropriately selected from known electrode materials according to the use and purpose of the light emitting device. As mentioned above, the anode is typically formed as a transparent anode.

(cathode)

The cathode should normally have a function as an electrode for injecting electrons into the organic layer, and the shape, structure, size, etc. are not particularly limited, and may be appropriately selected from known electrode materials according to the use and purpose of the light emitting device.

<Organic layer>

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

The organic layer is not particularly limited and may be appropriately selected depending on the use and purpose of the organic electroluminescent device, but is preferably formed on the transparent electrode or the translucent electrode. In this case, the organic layer is formed on the entire surface or one surface of 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.

(Composition of organic layer)

In the organic electroluminescent device of the present invention, it is preferable that the organic layer includes 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. When the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, low-cost and high-efficiency organic electroluminescent device can be manufactured.

In the organic electroluminescent element of this invention, it has a light emitting layer containing the said phosphorescent material, and another organic layer, It is preferable that 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 the light emitting layer containing the said phosphorescent material, and another organic layer. However, in the organic electroluminescent element of this invention, even when the said organic layer has a light emitting layer and another organic layer, it does not necessarily need to distinguish between layers clearly.

In the organic electroluminescent device of the present invention, the organic layer contains a phosphorescent material and a compound represented by the general formula (1). At this time, there is no restriction|limiting in particular in the place where the said phosphorescent 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 a light emitting layer containing the said phosphorescent material, and another organic layer, and that 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.

In addition, an electron transport layer adjacent to the cathode is provided between the pair of electrodes, and a hole blocking 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 blocking layer is of the general formula It is also preferable to contain the compound represented by (1).

Multiple layers of these organic layers may be formed, respectively, and when multiple layers are formed, they may be formed from the same material, and may be formed from the material different for every layer.

(Method of Forming Organic Layer)

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

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

(light emitting layer)

The light emitting layer receives holes from the anode, hole injection layer or hole transport layer when an electric field is applied, receives electrons from the cathode, electron injection layer or electron transport layer, provides a place for recombination of holes and electrons, and emits light layer that has 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 type of said phosphorescent material.

The said light emitting layer in the organic electroluminescent element of this invention may be comprised only with the said phosphorescent material, and the structure used as the mixed layer of the host material and the said phosphorescent material may be sufficient as it. One type or two or more types may be sufficient as the kind of the said phosphorescence emitting material. The host material is preferably a charge transport material. The number of the said host material may be 1 type, or 2 or more types may be sufficient as it, For example, the structure which mixed the host material of electron-transport property and the host material of hole-transport property is mentioned. Moreover, the said light emitting layer does not have charge transport property and may contain the material which does not emit light.

Moreover, the number of a light emitting layer may be one, or a multilayer of two or more layers may be sufficient as it, and the same light emitting material or host material may be contained in each layer, and may contain different materials for every layer. When there are a plurality of light-emitting layers, each light-emitting layer may emit light in a different light-emitting color.

The thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 3 nm to 200 nm from the viewpoint of external quantum efficiency, and 5 nm to 100 nm more preferably.

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

Hereinafter, as a material of the said light emitting layer, the compound represented by the said General formula (1), the said phosphorescent light emitting material, and other host materials other than 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) a compound represented by the general formula (1)

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

General formula (1)

[Formula 12]

(In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (however, an alkyl group and a cyano group are excluded), and 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.)

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

In the present invention, when referred to as a "substituent," the substituent may be substituted. For example, when referring to an "alkyl group" in the present invention, an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) or an alkyl group substituted with an aryl group (for example, a triphenylmethyl group), etc. are also included, but "the number of carbon atoms" A 1-6 alkyl group" refers to all groups including substituted ones having 1 to 6 carbon atoms.

In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom. A sulfur atom having a larger van der Waals radius is preferable from the viewpoint of improving electron mobility.

In the general formula (1), the ^{substituent represented by R 101} to R ¹¹⁰ is a substituent excluding an alkyl group and a cyano group, and each independently includes the following substituent group A, and the substituent may further have a substituent. . As said additional substituent, the group selected from the said substituent group A is mentioned.

《Substituent group A》

An alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc. ), an alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, propargyl, 3-pentynyl, etc.) , an aryl group (preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and examples include phenyl, p-methylphenyl, naphthyl, and anthryl. ), an amino group (preferably having 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.), an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, for example, methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, For example, phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc. are mentioned), a heterocyclic oxy group (preferably C1-C30, More preferably, C1-C20, Especially preferably having 1 to 12 carbon atoms, for example, pyridyloxy, pyrazinyloxy, pyrimidinyloxy, quinolyloxy, etc.), an acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to carbon atoms) 20, particularly preferably having 2 to 12 carbon atoms, for example, acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to carbon atoms) 20, particularly preferably having 2 to 12 carbon atoms and, for example, methoxycarbonyl, ethoxycarbonyl, etc.), an aryloxycarbonyl group (preferably has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms). and, for example, phenyloxycarbonyl and the like), an acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example acetoxy and benzoyloxy), an acylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, acetylamino, benzoylamino and the like), an alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, for example, methoxycarbonylamino, etc.) ), an aryloxycarbonylamino group (preferably has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example, phenyloxycarbonylamino and the like. ), a sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfonylamino and benzenesulfonylamino. ), a sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, for example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl and the like), a carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, carbamoyl, methylcarbamoyl, diethylcarbamoyl and phenylcarbamoyl), an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms) and, for example, methylthio, ethylthio, etc.), an arylthio group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example For example, phenylthio etc.), heterocyclic thio group (preferably has 1 to 30 carbon atoms, more preferably has 1 to 20 carbon atoms, particularly preferably has 1 to 12 carbon atoms, for example, pyridylthio, 2 -benzimizolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio, etc. are mentioned), a sulfonyl group (preferably C1-C30, More preferably, C1-C20, Especially preferably having 1 to 12 carbon atoms, for example mesyl, tosyl, etc.), a sulfinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, e.g. For example, methanesulfinyl, benzenesulfinyl, etc. are mentioned), a ureido group (preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, urea do, methylureido, phenylureido, etc.), a phosphoric acid amide group (preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example diethyl phosphoric acid amide, phenyl phosphoric acid amide, etc.), a hydroxyl group, a mercapto group, a halogen atom (eg, a fluorine atom, a chlorine atom, a bromine atom, an 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 1 to 12 carbon atoms, and the hetero atom is, for example, For example, nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imi Dazolyl, oxazolyl, thiazolyl, isoox Saazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimida zolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group, etc. are mentioned), silyl group (preferably C3-C40, More preferably C3-C30, Especially preferably C3 to 24, for example, trimethylsilyl, triphenylsilyl, etc.), a silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms) , for example, trimethylsilyloxy, triphenylsilyloxy, etc.) and a phosphoryl group (for example, diphenylphosphoryl group, dimethylphosphoryl group, etc. are mentioned). These substituents may be further substituted, and as an additional substituent, the group chosen from the substituent group A demonstrated above is mentioned.

R ¹⁰¹ to 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 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, for example, a phenyl group, a xylyl group, a biphenyl group, and a terphenyl group. , a naphthyl group, an anthryl group, a triphenylenyl group, and the like.

The ^{heteroaryl group represented by R 101} to R ¹¹⁰ preferably has 5 to 30 ring atoms, more preferably 5 to 20 ring atoms, particularly preferably 5 to 15 ring atoms, for example, a pyridyl group; and a pyrimidinyl group, a triazinyl group, a pyrazinyl group, a pyridazinyl group, a carbazolyl group, a dibenzothiophenyl group, and a dibenzofuranyl group.

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, ^{an aspect in which one or more of R 101} to R ¹⁰⁷ is a phenyl group is also preferable, and an aspect in which one or more of R 101 to R 107 is a phenyl group is also more preferable.

R ¹⁰⁸ and R ¹⁰⁹ are preferably a hydrogen atom, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group, and 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

As ^{the substituent when R 108} and R ¹⁰⁹ have an additional substituent, a substituted or unsubstituted aryl group or heteroaryl group is preferable, and a phenyl group is preferable.

As the R ¹¹⁰ are, of at least one of R ¹¹⁰ is a condensed ring of ring atoms, of 10 to be the ring atoms of the aryl group, the condensed ring 30 8-30 heteroaryl group, having 6 to 25 having them as substituents of the aryl group or a heteroaryl group having 5 to 25 ring atoms, or a monocyclic heteroaryl group having 5 to 25 ring atoms having as a substituent a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, and other R ¹¹⁰ is a hydrogen atom or a carbon number 6 to It is preferably an aryl group of 30 or a heteroaryl group of 5 to 25 ring atoms.

As R ¹¹⁰ , at least one ^{aryl group having 12 to 18 ring atoms in which R 110} is a condensed ring, a heteroaryl group having 9 to 13 ring atoms in which at least one R 110 is a condensed ring, or an aryl group having 6 to 18 carbon atoms having these as a substituent group or a heteroaryl group having 6 to 13 ring atoms, or a monocyclic heteroaryl group having 6 to 13 ring atoms having as a substituent a monocyclic aryl group having 6 to 18 carbon atoms, more preferably ^{R 110 is a hydrogen atom} do. In addition, the monocyclic heteroaryl group having 6 to 13 ring atoms having as a substituent a monocyclic aryl group having 6 to 18 carbon atoms as a substituent is a monocyclic heteroaryl group having 6 to 10 ring atoms having a monocyclic aryl group having 6 to 10 carbon atoms 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 carbon atoms having as a substituent an aryl group having 8 to 30 ring atoms as a condensed ring, an aryl group having 6 to 25 carbon atoms or a ring having these as a substituent The position of the substituent of ^{R 110} which is a monocyclic heteroaryl group having 5 to 20 ring atoms having a heteroaryl group having 6 to 13 atoms or a monocyclic aryl group having 6 to 20 carbon atoms as a substituent is the benzene ring substituted by ^{R 110 . With respect to the substituent forming the p-terphenylene skeleton of R 110} , any position of the ortho position, the meta position, and the para position may be used, and among them, the meta position or the para position suppresses the adcyclization reaction between R 110 and other substituents It is preferable from the viewpoint of doing or reducing the element driving voltage. Moreover, when the emission color from an organic electroluminescent element is green (emission peak wavelength 490-580 nm), it is more preferable that it is 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 (for example, a naphthyl group, an anthryl group, etc.) 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 a single bond. Preferred examples of the arylene group represented by L ¹⁰¹ include a phenylene group, a biphenylene group, and a terphenylene group. In addition, these connection forms are not specifically limited.

L ¹⁰¹ is preferably a single bond, a phenylene group, a biphenylene group or a terphenylene group, a single bond or a terphenylene group (particularly, a p-terphenylene group or m-terphenylene group is preferable, and p-terphenylene group group is more preferable, and an unsubstituted p-terphenylene group is particularly preferable) is more preferable, and a single bond is still more preferable.

In the present invention, p-terphenylene and m-terphenylene each represent the following structures (* represents a bond).

[Formula 13]

L ²⁰¹ is preferably unsubstituted, but may further have a substituent in some cases. Examples of the substituent in the case where L ²⁰¹ has an additional substituent include the aforementioned substituent group A, and a substituted or unsubstituted aryl group (phenyl group or biphenyl group) is preferable, and a phenyl group is preferable.

In the organic electroluminescent device of the present invention, the compound represented by the general formula (1) is preferably a compound represented by the following general formula (2) or (3).

general formula (2)

[Formula 14]

In the 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 an aryl group having as a substituent the number of ring atoms A 5 to 25 heteroaryl group or a monocyclic heteroaryl group having 5 to 25 ring atoms having as a substituent a monocyclic aryl group having 6 to 25 carbon atoms is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.

The preferable range of X ^{201 in} the said General formula (2) is the same as the preferable range ^{of X 101 in the said General formula (1).}

The preferred range of the above in the formula (2) R ²⁰¹ ~ R ²⁰⁹ is the same as the preferable ranges of R ¹⁰¹ ~ R ¹⁰⁹ in the 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 the general formula (2), a heteroaryl group having 8 to 30 ring atoms as a condensed ring, and carbon atoms having these as a substituent A preferable range of the monocyclic heteroaryl group having 5 to 25 ring atoms having as a substituent a 6 to 25 aryl group, a 5 to 25 heteroaryl group, or a monocyclic aryl group having 6 to 25 ring atoms as a substituent is dibenzo A thiophenyl group, a dibenzofuranyl group, a triphenylenyl group, a carbazolyl group, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms having these substituents, or a monocyclic aryl group having 6 to 13 ring atoms It is a monocyclic heteroaryl group having 5 to 25 ring atoms and having a group as a substituent. Among them, a dibenzothiophenyl group, a dibenzofuranyl group, a triphenylenyl group, or a phenylene group having these substituents is more preferable, and a dibenzothiophenyl group, a dibenzofuranyl group or a triphenylenyl group is particularly preferable, A benzothiophenyl group or a triphenylenyl group is more particularly preferable, and a triphenylenyl group is still more preferable.) In these condensed rings, the above-mentioned skeleton is a basic skeleton, and substituents may be further condensed with each other.

^{The other one of A 201} and A ²⁰² in the general formula (2) is preferably a hydrogen atom, an aryl group having 6 to 25 carbon atoms, or a heteroaryl group having 5 to 25 ring atoms, more preferably a hydrogen atom do.

^{L 201} in the general formula (2) represents a single bond or an arylene group, and is not a p-terphenylene group.

The ^{arylene group represented by L 201} may be a condensed ring (for example, a naphthyl group, an anthryl group, etc.), but when the emission color from the organic electroluminescent element is green (the emission peak wavelength is 490 to 580 nm) It is preferably an arylene group having no condensed ring from the viewpoint of efficiency, more preferably a phenylene group, a biphenylene group, or an m-terphenylene group, and a 1,3-phenylene group or a 3,5'-biphenylene group It 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 an aryl group having as a substituent the number of ring atoms A 5 to 25 heteroaryl group or a monocyclic heteroaryl group having 5 to 20 ring atoms having as a substituent a monocyclic aryl group having 6 to 25 carbon atoms is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.

^{The preferable range of X 301 in} the said General formula (3) is the same as the preferable range ^{of X 101 in} the said General formula (1).

A preferable range for R ³⁰¹ to R ³¹² in the general formula (3) is the same as a preferable range for ^{R 101} to R ^{109 in the general formula (1).}

A preferable range for R ³¹³ to R ³¹⁵ in the general formula (3) is the same as a preferable range for ^{R 210} to R ^{212 in the general formula (2).}

The preferable ranges of A ³⁰¹ and A ^{302 in} the said General formula (3) are the same as the preferable ranges ^{of A 201} and A ^{202 in the said General formula (2).}

^{The arylene group represented by L 301} in the general formula (3) may be a condensed ring (eg, a naphthyl group, an anthryl group, etc.), but the emission color from the organic electroluminescent element is green (the emission peak wavelength is 490 to 580 nm), preferably an arylene group having no condensed ring from the viewpoint of luminous efficiency, more preferably a phenylene group, a biphenylene group, or an m-terphenylene group, and a 1,3-phenylene group or 3 A ,5'-biphenylene group is particularly preferred.

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

In the organic electroluminescent device of the present invention, the compound represented by the general formula (1) is particularly preferably a compound represented by any of the following general formulas (4) to (7) and the general formula (11) described later, It is more particularly preferable that the compound represented by the formula (1) is a compound represented by any of the following general formulas (4) to (7).

[Formula 16]

In the 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 preferred range of the above in the formula (4) R ⁴⁰¹ ~ R ⁴⁰⁷ and R ⁴¹¹ ~ R ⁴¹⁷ is the same as the preferable ranges of R ¹⁰¹ ~ 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 preferable range ^{of R 108} and R ^{109 in the general formula (1).}

It is preferable that _{n 401} in the said General formula (4) is 0.

[Formula 17]

In the 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 ⁴¹³ may be the same as or different from each other. n ₅₀₁ represents 0 or 1.

^{The preferable range of X 501 in} the said General formula (5) is the same as the preferable range ^{of X 101 in} the said General formula (1).

^{A preferable range for R 501} to R ⁵⁰⁷ in the general formula (5) is the same as a preferable range for ^{R 101} to R ¹⁰⁷ in the general formula (1).

^{A preferable range for R 508} to R ⁵¹⁰ in the general formula (5) is the same as a preferable range for ^{R 108} and R ¹⁰⁹ in the general formula (1).

^{R 511} to R ⁵¹³ in the general formula (5) 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.

It is preferable that _{n 501} in the said General formula (5) is 0.

[Formula 18]

In the 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 the general formula (6) are the same as the preferable ranges ^{of R 101} to R ^{107 in the general formula (1).}

^{A preferable range for R 608} to R ⁶¹³ in the general formula (6) is the same as a preferable range for ^{R 108} and R ¹⁰⁹ in the general formula (1).

[Formula 19]

In the 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.

^{The preferable range of X 701 in} the said General formula (7) is the same as the preferable range ^{of X 101 in} the said General formula (1).

^{The preferable range of R 701} -R ^{707 in} the said General formula (7) is the same as the preferable range ^{of R 101} -R ^{107 in} the said General formula (1).

^{The preferable ranges of R 708} to R ⁷¹³ in the general formula (7) are the same as the preferable ranges ^{of R 108} and R ¹⁰⁹ in the general formula (1).

A preferable range for R ⁷¹⁴ to R ⁷¹⁶ in the general formula (7) is the same as a preferable range for ^{R 511} to R ^{513 in the general formula (5).}

<The compound of the present invention - a particularly preferred aspect of the compound represented by the general formula (1)->

Among the compounds represented by the general formula (1), in the present invention, compounds represented by any of the following general formulas (8) to (11) are particularly preferred. The compound of the present invention represented by any of the following general formulas (8) to (11) can be used in organic electronic devices such as electrophotography, organic transistors, organic photoelectric conversion elements (energy conversion applications, sensor applications, etc.), and organic electroluminescent elements. It can be used preferably, and it is especially preferable to use it for an organic electroluminescent element.

[Formula 20]

In the general formulas (8) to (11), X ⁸⁰¹ to X ⁸⁰⁶ each independently represents an oxygen atom or a sulfur atom, and R ⁸⁰¹ to R ⁸⁰⁶ each independently represents 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 of them is a nitrogen atom.

In the general formulas (8) to (11), ^{a preferable range of X 801} to X ⁸⁰⁶ is the same as a preferable range ^{for X 101} in the general 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, more preferably a hydrogen atom.

In the general formula (11), A ¹¹ to A ¹³ each independently represents CH or a nitrogen atom, and at least one of them is a nitrogen atom. When the number of nitrogen atoms contained in ^{A 11} to A ^{13 is one, A 11} or A ¹² is preferably a nitrogen atom. When the number of nitrogen atoms contained in ^{A 11} to A ^{13 is two, A 12} and A ¹³ are preferably nitrogen atoms.

In the compound represented by the general formula (11), A ¹¹ to A ¹³ has one nitrogen atom and A ¹¹ or A ¹² is a nitrogen atom, or A ¹¹ to A ¹³ has two nitrogen atoms, A ¹² and A ¹³ or a nitrogen atom, a ¹¹ a ¹³ ~ this is both more preferably a nitrogen atom. Among them, a compound in which one nitrogen atom is contained in ^{A 11} to A ^{13 and A 12} is a nitrogen atom, and a compound in which A ¹¹ to A ¹³ contains two nitrogen atoms and A ¹² and A ¹³ are nitrogen atoms are particularly preferred. do.

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

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

When the compound represented by the general formula (1) is used as a host material of a light emitting layer of an organic electroluminescent element or a charge transport material of a layer adjacent to the light emitting layer, the energy gap in a thin film state (organic electroluminescence of the present invention) In the case where the light emitting material is a phosphorescent light emitting material as in the case of an element, if the minimum triplet excitation (T ₁ ) energy) in the thin film state is large, quenching of light emission is prevented, which is advantageous for improving efficiency. On the other hand, from the viewpoint of chemical stability of the compound, it _{is preferable that the energy gap and the T 1} energy are not too large.

_{The T 1} energy in the film state of the compound represented by the general formula (1) is preferably 1.77 eV (40 kHz/mol) or more and 3.51 eV (81 kHz/mol) or less, and 2.39 eV (55 kHz/mol) or more. It is more preferable that it is 3.25 eV (75 ㎉/mol) or less. In the organic electroluminescent device of the present invention, it is preferable from the viewpoint of luminous efficiency 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 to be described later.} In particular, when the emission color from the organic electroluminescent device is green (the emission peak wavelength is 490 to 580 nm), from the viewpoint of luminous efficiency, the T ₁ energy is 2.39 eV (55 kHz/mol) or more and 2.82 eV (65 kHz/mol) It is more preferable that it is the following.

T ₁ energy can be obtained from the short wavelength range by measuring the phosphorescence emission spectrum of the thin film of the material. For example, a material is deposited on a cleaned quartz glass substrate to a film thickness of about 50 nm by vacuum deposition, and the phosphorescence emission spectrum of the thin film is measured with an F-7000 Hitachi Spectrofluorescence Spectrophotometer (Hitachi Hi-Technologies) under liquid nitrogen temperature. is measured using By converting the wavelength of the short wavelength side increases the emission spectrum obtained in the energy unit can obtain the T ₁ energy.

From the viewpoint of stably operating the organic electroluminescent device against heat generation during high-temperature driving or driving the device, or from the viewpoint of reducing the chromaticity difference during high-temperature storage, in the organic electroluminescent device of the present invention, the compound represented by the general formula (1) It is preferable that this glass transition temperature is a compound 100 degreeC or more. The glass transition temperature (Tg) of the compound represented by the general formula (1) is more preferably 100°C or more and 400°C or less, particularly preferably 120°C or more and 400°C or less, and still more preferably 140°C or more and 400°C or less.

When the purity of the compound represented by the general formula (1) is low, impurities act as a charge transport trap or accelerate device deterioration, so the higher the purity of the compound represented by the general formula (1) is, the more preferable. The 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 such general formula (1), sublimation refinement|purification etc. are mentioned, for example.

Specific examples of the compound represented by the general formula (1) are listed below, but the present invention is not limited thereto.

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

The compound exemplified as the compound represented by the general formula (1) is, for example, a metal catalyst (for example, Pd or Ni etc.) and a ligand (triphenylphosphine, a Buchwald ligand, etc.) can be synthesize|combined by the 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. The introduction layer of the compound represented by the general formula (1) is preferably contained in any of the light emitting layer, the layer between the light emitting layer and the cathode (especially the layer adjacent to the light emitting layer), and the layer between the light emitting layer and the anode. and more preferably contained in any layer or a plurality of the light emitting layer, the electron transport layer, the electron injection layer, the exciton block layer, the hole block layer, and the hole block layer, It is more preferable, and it is especially preferable to contain it in a light emitting layer or an electron carrying layer. Moreover, you may use the compound represented by the said General formula (1) in said multiple layer. For example, you may use for both a light emitting layer and an electron carrying layer.

When the compound represented by the general formula (1) is contained in the light emitting layer, the compound represented by the general formula (1) is preferably contained in an amount of 0.1 to 99 mass%, and contains 1 to 97 mass%, based on the total mass of the light emitting layer. It is more preferable to make it do it, and it is still more preferable to make it contain 10-96 mass %. When the compound represented by the general formula (1) is further contained in a layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100 mass%, and contained in an amount of 85 to 100 mass% with respect to the total mass of the layer other than the light emitting layer. more preferably.

(phosphorescent material)

In the present invention, it is preferable to have at least one kind of phosphorescent light emitting material in the light emitting layer. In the present invention, in addition to the above-mentioned phosphorescent material, as the light-emitting material, a fluorescent light-emitting material or a phosphorescent light-emitting material different from the phosphorescent material contained in the light-emitting layer can be used.

For these fluorescent and phosphorescent materials, for example, in paragraphs [0100] to [0164] of Japanese Patent Application Laid-Open No. 2008-270736 and paragraphs [0088] to [0090] of Japanese Patent Application Laid-Open No. 2007-266458. It has been described in detail, and the matters described in these publications can be applied to the present invention.

As a phosphorescent light emitting material usable in the present invention, 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, Japanese Patent Application Laid-Open No. 2001-247859, Japanese Patent Application Laid-Open No. 2002-302671, Japanese Patent Application Laid-Open No. 2002-117978, Japanese Patent Application Laid-Open No. 2003-133074, Japanese Patent Application Laid-Open No. 2002 -235076, Japanese Patent Application Laid-Open No. 2003-123982, Japanese Patent Application Laid-Open No. 2002-170684, EP1211257, Japanese Patent Application Laid-Open No. 2002-226495, Japanese Patent Application Laid-Open No. 2002-234894, Japanese Patent Application Laid-Open No. 2001-247859, Japanese Patent Application Laid-Open No. 2001 -298470, Japanese Patent Application Laid-Open No. 2002-173674, Japanese Patent Application Laid-Open No. 2002-203678, Japanese Patent Application Laid-Open No. 2002-203679, Japanese Patent Application Laid-Open No. 2004-357791, Japanese Patent Application Laid-Open No. 2006-256999, Japanese Unexamined Patent Application Publication No. 2007-19462 , a phosphorescent light emitting compound described in patent documents such as JP 2007-84635 and JP 2007-96259 , etc. are mentioned, and among these, as a more preferable light emitting material, an iridium (Ir) complex, platinum (Pt) ) complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Dy complex, and phosphorescent metal complex compounds such as Ce complex. . Particularly preferred are iridium (Ir) complexes, platinum (Pt) complexes, or Re complexes, and among them, at least one of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond is included. An iridium (Ir) complex, a platinum (Pt) complex, or a Re complex is preferred. In addition, from the viewpoints of luminous efficiency, driving durability, chromaticity, etc., an iridium (Ir) complex, a platinum (Pt) complex are particularly preferable, and an iridium (Ir) complex is most preferable.

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

As the phosphorescent material contained in the light emitting layer, it is preferable to use an iridium (Ir) complex represented by the following general formula (E-1). 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 an atomic group forming a 5 or 6 membered hetero ring together with Z ^{1 and a nitrogen atom.}

B ₁ represents an atom group that forms a 5 or 6 membered ring together with Z ^{2 and a carbon atom.}

(X-Y) represents a monoanionic bidentate ligand.

n _E1 represents the integer of 1-3.

n _E1 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 an atomic group forming a 5 or 6 membered hetero ring together with Z ^{1 and a nitrogen atom.} A ₁ , Z ¹ and a 5 or 6 membered hetero ring containing a nitrogen atom include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring , a triazole ring, an oxadiazole ring, and a thiadiazole ring.

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

The 5- or 6-membered heterocyclic ring formed from the said A ₁ , Z ¹ and a nitrogen atom may have a substituent, and the said substituent group A is applicable as a substituent. Substituents are appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron-donating group, a fluorine atom, or an aromatic ring group is preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, a fluorine atom, an aryl group, a hetero an aryl group and the like are selected. Moreover, when making it long wavelength, an electron withdrawing group is preferable, for example, it is preferable that 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.

The substituent on carbon is preferably 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.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.

The substituents may be linked to each other to form a condensed ring, and the formed rings 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 ring. a ring, a thiophene ring, a furan ring, etc. are mentioned. These formed rings may have a substituent, and as a substituent, the substituent on the carbon atom mentioned above and the substituent on the nitrogen atom are mentioned.

B ₁ represents Z ² and a 5 or 6 membered ring containing carbon atoms. B ₁ , Z ² and a 5 or 6 membered ring formed of carbon atoms include, but are not limited to, a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring. , a thiazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, a furan ring, and the like.

From the viewpoints of complex stability, emission wavelength control and emission quantum yield, _{a 5- or 6-membered ring formed of B 1} , Z ² and carbon atoms is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, and a pyrazole ring. a ring or a thiophene ring, more preferably a benzene ring, a pyridine ring, or a pyrazole ring, and still more preferably a benzene ring or a pyridine ring.

The 5 or 6 membered ring formed from the above B ₁ , Z ² and carbon atoms may have a substituent, the above substituent group A as the substituent on the carbon atom, and the following substituent group B as the substituent on the nitrogen atom can be applied. .

The substituent on carbon is preferably 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》

An alkyl group (preferably having 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.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, , for example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), an alkynyl group (preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 carbon atoms) -10, for example, propargyl, 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms) and, for example, phenyl, p-methylphenyl, naphthyl, anthryl, etc.), a cyano group, a heterocyclic group (including a heteroaryl group, preferably 1 to 30 carbon atoms, more preferably 1 carbon atom) to 12, and the hetero atom is, for example, 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, piperidino , morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group, etc.) These substituents are further substituted may be sufficient, and as an additional substituent, the group selected from the substituent group B demonstrated above is mentioned.

The substituent on the carbon is appropriately selected for controlling the emission wavelength or potential, but in the case of making the wavelength longer, an electron-donating group or an aromatic cyclic group is preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, a heteroaryl group, etc. this is chosen Moreover, when making it short wavelength, 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.

The substituent on nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to each other to form a condensed ring, and the formed rings 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 ring. a ring, a thiophene ring, a furan ring, etc. are mentioned. These formed rings may have a substituent, and as a substituent, the substituent on the carbon atom mentioned above and the substituent on the nitrogen atom are mentioned.

In addition, the A ₁ , Z ¹ and a substituent of a 5 or 6 membered heterocyclic ring formed of a nitrogen atom, and a substituent of _{a 5 or 6 membered ring formed of the B 1} , Z ² and a carbon atom are connected to the same condensed ring as described above may be formed.

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

The bidentate monoanionic ligand represented by (X-Y) is preferably a bidentate monoanionic ligand represented by the 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, and may be saturated or unsaturated. Examples of the substituent in the case of having a substituent include the following substituent Z', and preferable examples of the substituent Z' include a phenyl group, a heteroaryl group, a fluorine atom, a silyl group, an amino group, a cyano group, or a group formed by combining them, 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, more preferably an alkyl group having 1 to 5 carbon atoms.

《Substituent Z'》

an alkyl group (preferably having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, 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 having 2 to 8 carbon atoms, more preferably 2 to 5 carbon atoms) , for example, vinyl, etc.), an aryl group (6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, for example, a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, a pyrenyl group, a phenyl group Relenyl group, triphenylenyl group and chrysenyl group are mentioned), heteroaryl group (preferably has 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.), alkoxy group (preferably having 1 to 8 carbon atoms, more It preferably has 1 to 5 carbon atoms, for example, methoxy group, ethoxy group, n-propyloxy group, iso-propyloxy group, etc.), phenoxy group, halogen atom (preferably fluorine atom), silyl group (preferably having 4 to 30 carbon atoms, more preferably having 4 to 20 carbon atoms, and trimethylsilyl group, triethylsilyl group, triphenylsilyl group, etc. are mentioned), amino group (preferably having 2 to 60 carbon atoms, More preferably, it has 2 to 40 carbon atoms and includes a dimethylamino group, a diethylamino group, and a diphenylamino group), a cyano group, or a group comprising a combination thereof, and a plurality of substituents Z' are bonded to each other to form an aryl ring, also be Examples of the aryl ring formed by bonding a plurality of substituents Z' to each other include a phenyl ring and a pyridine ring, and a phenyl ring is preferable.

The ^{aryl group represented by R L1} to R ^L3 may be condensed or may have a substituent. Examples of the substituent in the case of having a substituent include the aforementioned substituent Z', and as the 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. Examples of the substituent in the case of having a substituent include the aforementioned substituent Z', and as the 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 C 4 to C 12 heteroaryl group, more preferably a C 4 to C 10 heteroaryl group.

R ^L1 and R ^L2 are preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and particularly preferably an alkyl group.

The ^{alkyl group represented by R L1} and R ^L2 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, for example, a methyl group, an ethyl group, or an n-propyl group. , iso-propyl group, iso-butyl group, t-butyl group, n-butyl group, cyclohexyl group and the like, and methyl group, ethyl group, iso-butyl group, or t-butyl group is preferable, and methyl group is particularly 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 aspect 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 general formula (E-2), A ^E1 to A ^E8 each independently represent a nitrogen atom or ^{C R E} .

R ^E represents a hydrogen atom or a substituent.

(X-Y) represents a monoanionic bidentate ligand.

n _E2 represents the integer of 1-3.

A ^E1 to A ^E8 each independently represent a nitrogen atom or ^{C R E} . R ^E represents a hydrogen atom or a substituent, and R ^E may be linked to each other to form a ring. As a ring to be formed, the thing similar to the condensed ring described in the general formula (E-1) mentioned above is mentioned. As ^{a substituent represented by R E} , what was mentioned as said substituent group A is applicable.

A ^E1 to A ^E4 are preferably ^{C R} , and when A ^E1 to A ^E4 are ^C R , preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group or an aryloxy group as ^{R E} of A ^{E3 .} , 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 A R ^{E of 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 aryloxy group. , or a fluorine atom, particularly preferably a hydrogen atom.

And A ^E5 ~ A ^E8 preferably CR ^E a, A ^E5 ~ A ^E8 is CR in case of ^E, preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a di-alkyl as R ^E an amino group, a diarylamino group, an alkyloxy group, a cyano group, or a fluorine atom, more preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, or a fluorine atom, still more preferably is a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. Moreover, if possible, substituents may be connected to each other to form a condensed ring structure. When shifting the emission wavelength to the short wavelength side, it is preferable that ^{A E6 is a nitrogen atom.}

(XY) and n _{E2 have the same meanings as (XY) and n E1} in the general formula (E-1), and their preferred ranges are also the same.

A more preferable embodiment of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).

[Formula 28]

In the general formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 are each independently 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 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, 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.

R ^T1 to R ^T7 and R' may combine with 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 ring is cycloalkyl, aryl or heteroaryl. The 7-membered ring may further have a substituent Z. Among these, ^{the case of condensing with R T1} and R ^T7 or R ^T5 and R ^T6 to form a benzene ring is preferable, and the case ^{of condensing with R T5} and R ^T6 to form a benzene ring is particularly preferable.

each 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", or -SO ₃ R", R" is each independently 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.

(XY) represents a monoanionic bidentate ligand. n _E3 represents the integer of 1-3.

The alkyl group may have a substituent, and may be saturated or unsaturated, and the substituent Z mentioned above is mentioned as a group which may be substituted. The ^{alkyl group represented by R T1} to R ^T7 and R' is preferably an alkyl group having 1 to 8 total carbon atoms, more preferably an alkyl group having 1 to 6 total carbon atoms, for example, a methyl group, an ethyl group, i-propyl group, cyclohexyl group, t-butyl group, etc. are mentioned.

The cycloalkyl group may have a substituent, may be saturated or unsaturated may be sufficient, and the substituent Z mentioned above is mentioned as a group which may be substituted. The ^{cycloalkyl group represented by R T1} to R ^T7 and R' is preferably a cycloalkyl group having 4 to 7 ring atoms, more preferably a cycloalkyl group having 5 to 6 total carbon atoms, for example, cyclophene. A tyl group, a cyclohexyl group, etc. are mentioned.

The ^{alkenyl group represented by R T1} to R ^T7 and R' preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl, etc. are mentioned.

The ^{alkynyl group represented by R T1} to R ^T7 and R' is preferably from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, particularly preferably from 2 to 10 carbon atoms, 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.

The ^{aryl group represented by R T1} to R ^T7 and R' preferably includes a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, for example, a phenyl group, a tolyl group, and a naphthyl group.

The ^{heteroaryl group represented by R T1} to R ^T7 and R' is preferably a C 5 to C 8 heteroaryl group, more preferably a 5 or 6 membered substituted or unsubstituted heteroaryl group, for example, Pyridyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indole Lyl group, furyl group, benzofuryl group, thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothia Jolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isoxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, A thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothienyl group, 7 pyridoindolyl group, etc. are mentioned. Preferred examples are a pyridyl group, a pyrimidinyl group, an imidazolyl group, and a thienyl group, and more preferably a pyridyl group and a 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, or a heteroaryl group, and more preferably is a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, or an aryl group, more preferably a hydrogen atom, an alkyl group, or an aryl group. As 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.

R ^T1 to R ^T7 , and R' may combine with each other any two 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 ring 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 ^{for R T1} to R ^{T7 , and R'.}

In addition, while A represents CR' ^{, it is particularly preferable that 0 to 2 of R T1} to R ^T7 and R' are an alkyl group or a phenyl group, and the remainder are all hydrogen atoms, R ^T1 to R ^T7 , and Among R', the case where 0-2 are an alkyl group and all the remainder are hydrogen atoms is especially preferable.

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

(X-Y) has the same meaning as (X-Y) in the general formula (E-1), and the preferable range is also the same.

One preferred embodiment of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).

[Formula 29]

R ^T1 to R ^T4 , A, (XY) and n _E4 in the general formula (E-4) are R ^T1 to R ^T4 , A, (XY) and n _{E3 in the general formula (E-3)} and has the same meaning, and the preferred range is also the same. R ₁ ' to R ₅ ' are each independently 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 ₁ ' to R ₅ ' may combine with 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 The ring may further have a substituent Z.

each 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", or -SO ₃ R", R" is each independently 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.

Also, the preferable range of the R ₁ '~ R _5' is the same as R ~ ^{T1 T7} R, R 'in the formula (E-3). In addition, while A represents CR' ^{, it is particularly preferable that 0 to 2 of R T1} to R ^T4 , R', and R ₁ ' to R ₅ ' are an alkyl group or a phenyl group, and the remainder are all hydrogen atoms. , R ^T1 to R ^T4 , R', and R ₁ ' to R ₅ ', it is more preferable that 0 to 2 of them are alkyl groups and the rest are all hydrogen atoms.

Although preferable specific examples of the compound represented by the said general formula (E-1) are 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 described in Unexamined-Japanese-Patent No. 2009-99783, and various methods described in US Patent 7279232 etc. It is preferable to refine|purify by sublimation refinement|purification after performing refinement|purification by column chromatography, recrystallization, etc. after a synthesis|combination. By sublimation purification, not only organic impurities can be separated, but also inorganic salts, residual solvents, and the like can be effectively removed.

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

The phosphorescent material in the light-emitting layer is preferably contained in an amount of 0.1 mass% to 50 mass% with respect to the total mass of the compound that generally forms the light-emitting layer in the light-emitting layer, and from the viewpoint of durability and external quantum efficiency, 1 mass% to 50 mass% It is more preferable to contain %, and it is especially preferable to contain 2 mass % - 40 mass %.

In the present invention, it is particularly preferable to use a compound represented by any of the general formulas (1) to (7) and a compound represented by any of the general formulas (E-1) to (E-4) in a light emitting layer in combination.

(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-based compound, polysilane-based compound, poly(N-vinylcarbazole) , aniline-based copolymer, thiophene oligomer, conductive polymer oligomer such as polythiophene, organosilane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, fluorine Heterocyclic tetracarboxylic acid anhydrides such as renone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, and naphthaleneperylene; and various metal complexes represented by metal complexes of phthalocyanine and 8-quinolinol derivatives, metal complexes containing metal phthalocyanine, benzoxazole or benzothiazole as ligands, and derivatives thereof (which may have a substituent or a condensed ring), and the like. have.

(Other floors)

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 (a hole block layer, an exciton block layer, etc.), an electron transport layer, etc. are mentioned. Although the following can be mentioned as said specific layer structure, this invention is not limited to these structures.

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 one organic layer preferably arrange|positioned between the said anode and the said light emitting layer. (A) Examples of the organic layer preferably disposed between the anode 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 one organic layer preferably arrange|positioned between the said cathode and the said light emitting layer. (B) Examples of the organic layer preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.

Specifically, an example of a preferred aspect of the organic electroluminescent device of the present invention is the aspect described in FIG. 1 , and as the organic layer, from the anode side (3), the hole injection layer (4), the hole transport layer (5), the light emitting layer (6) ), the hole blocking layer 7 and the electron transporting layer 8 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) an organic layer preferably disposed 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 the 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 JP 2008-270736 A can be applied to the present invention.

The hole injection layer preferably contains an electron-accepting dopant. By containing the electron-accepting dopant in the hole injection layer, there are effects such as improving the hole injection property, lowering the driving voltage, and improving the efficiency. The electron-accepting dopant may be any of an organic material and an inorganic material as long as it is a material capable of generating radical cations by withdrawing electrons from the material to be doped. For example, tetracyanoquinodimethane (TCNQ), tetrafluoro tetracyanoquinodimethane (F ₄ -TCNQ), molybdenum oxide, and the like.

The electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01 mass% to 50 mass%, more preferably 0.1 mass% to 40 mass%, 0.2 mass% with respect to the total mass of the compound forming the hole injection layer. It is more preferable to contain -30 mass %.

(A-2) electron block layer

The electron blocking 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, an electron blocking layer can be formed as an organic layer adjacent to the light emitting layer on the anode side.

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

As an example of the organic compound which comprises an electron blocking layer, the thing mentioned as the hole transporting material mentioned above can be applied, for example.

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

The electron blocking layer may have a single-layer structure composed of one or two or more of the above-mentioned materials, or a multilayer structure composed of multiple layers of the same composition or different compositions.

(A-3) A material 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 device of the present invention includes at least one compound represented by the following general formula (M-1) as a material particularly preferably used for the organic layer preferably disposed between the (A) anode and the light emitting layer. can

The compound represented by the general formula (M-1) is more preferably contained in the organic layer adjacent to the light emitting layer between the light emitting layer and the anode, but its use is not limited and may be further contained in any layer in the organic layer. As the introduction layer of the compound represented by the general formula (M-1), any or multiple of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a charge blocking layer can be contained.

It is more preferable that the organic layer adjacent to the light emitting layer between the light emitting layer and the anode in which the compound represented by the general formula (M-1) is contained is an electron blocking layer or a hole transport layer.

[Formula 33]

In the general 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 heteroatoms is 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, or arylamino, and may further have a substituent Z.

each 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", or -SO ₃ R", R" is each independently 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.

p is an integer of 1 to 4, and when p is 2 or more, Ar ₁ and Ar ₂ may be the same or different, respectively.

Another preferred embodiment of the compound represented by the general formula (M-1) is a case represented by the following general formula (M-2).

[Formula 34]

In the general formula (M-2), R ^M1 represents an alkyl group, an aryl group, or a 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 the general formula (M-2), R ^M1 represents 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). shown, and these may have the substituent Z mentioned above. R ^M1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. Preferred substituents when the aryl group of R ^M1 has a substituent include an alkyl group, a halogen atom, a cyano group, an aryl group, and an alkoxy group, more preferably an alkyl group, a halogen atom, a cyano group, or an aryl group, an alkyl group, cyano group 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 an alkyl group or a phenyl group which may have a cyano group.

R ^M2 to R ^M23 are each independently 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), or an alkoxy group (preferably has 1 to 8 carbon atoms), aryloxy group (preferably has 6 to 30 carbon atoms), amino group (preferably has 0 to 24 carbon atoms), silyl group (preferably has 0 to 18 carbon atoms), cyano group, nitro A group or a fluorine atom is shown, and these may have the substituent Z mentioned above.

R ^M2 , R ^M7 , R ^M8 , R ^M15 , R ^M16 and R ^M23 are preferably a hydrogen atom or an alkyl or aryl group optionally having 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 optionally substituted alkyl or aryl group, 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 or aryl group optionally having a substituent Z, a fluorine atom, or a cyano group, more preferably a hydrogen atom; Or it is an alkyl group which may have the 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 optionally having 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 a hydrogen atom, an alkyl group or an aryl group which may have a substituent Z, a nitro group, a fluorine atom, or a cyano group, More preferably, it is a hydrogen atom or the alkyl group which may have the substituent Z. As a substituent in case an alkyl group has a substituent, a fluorine atom is preferable, The number of carbon atoms 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 preferred embodiment of the compound represented by the 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, represents a halogen atom, an aryl group or a heteroaryl group, Z may have a substituent further. 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 a plurality of R ^S1 to R ^S5 exist, they may combine with each other to form a ring, and may further have a substituent Z.

a represents the integer of 0-4, and ^{when several} R S1 exists, they may be same or different, and may combine with each other and may form a ring. b to e each independently represent an integer of 0 to 5, and when a plurality of R ^S2 to R ^S5 each exist, they may be the same or different, and any two may combine to form a ring.

q is an integer of 1 to 5, and when q is 2 or more, a plurality of R ^S1 may be the same or different, and may be bonded to each other to form a ring.

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

The cycloalkyl group may have a substituent, may be saturated or unsaturated may be sufficient, and the substituent Z mentioned above is mentioned as a group which may be substituted. The ^{cycloalkyl group represented by R S1} to R ^S5 is preferably a cycloalkyl group having 4 to 7 ring atoms, more preferably a cycloalkyl group having 5 to 6 total carbon atoms, for example, a cyclopentyl group or cyclohexyl group. and the like.

The ^{alkenyl group represented by R S1} to R ^S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, vinyl, allyl, 1-propenyl. , 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl, and the like.

The ^{alkynyl group represented by R S1} to R ^S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, ethynyl, propargyl, 1 -propynyl, 3-pentynyl, etc. are mentioned.

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

The ^{aryl group represented by R S1} to R ^S5 preferably includes a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, for example, a phenyl group, a tolyl group, a biphenyl group, and a terphenyl group.

The ^{heteroaryl group represented by R S1} to R ^S5 is preferably a C5 to C8 heteroaryl group, more preferably a 5 or 6 membered substituted or unsubstituted heteroaryl group, for example, a pyridyl group; Pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, cinnolinyl group, phthalazinyl group, quinoxalinyl group, pyrrolyl group, indolyl group, fu Lyl 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, isoxazolyl group, benzisooxazolyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, imidazolidinyl group, thiazolinyl group , a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothienyl group, and a pyridoindolyl group. Preferred examples are a pyridyl group, a pyrimidinyl group, an imidazolyl group, and a thienyl group, and more preferably a pyridyl group and a 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, or a heteroaryl group, more preferably a hydrogen atom; They are 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 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 combine with each other to form a condensed 4 to 7 membered ring, the fused 4 to 7 membered ring is cycloalkyl, aryl or heteroaryl, and the condensed 4 to 7 membered ring is Furthermore, you may have the 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 ^{for R S1} to R ^{S5 .}

When the compound represented by the general formula (M-1) is used in the hole transport layer, the compound represented by the general formula (M-1) is preferably contained in an amount of 50 to 100 mass%, and is contained in an amount of 80 to 100 mass%. It is preferable, and it is especially preferable to contain 95-100 mass %.

Moreover, when using the compound represented by the said general formula (M-1) for a some organic layer, it is preferable to contain in the 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 it combining several compounds represented by general formula (M-1) in arbitrary ratios.

The thickness of the hole transport layer containing the compound represented by the general formula (M-1) is preferably 1 nm to 500 nm, more preferably 3 nm to 200 nm, still more preferably 5 nm to 100 nm. do. Moreover, it is preferable that the positive hole transport layer is formed in contact with the light emitting layer.

_{The minimum triplet excitation (T 1} ) energy in the film state of the compound represented by the general formula (M-1) is preferably 1.77 eV (40 kHz/mol) or more and 3.51 eV (81 kHz/mol) or less, and 2.39 eV (55 kHz/mol) or more and 3.25 eV (75 kHz/mol) or less are more preferable. In the organic electroluminescent device of the present invention, it is preferable from the viewpoint of luminous efficiency 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 material described above.} In particular, when the emission color from the organic electroluminescent device is green (the emission peak wavelength is 490 to 580 nm), from the viewpoint of luminous efficiency, the T ₁ energy is 2.39 eV (55 kHz/mol) or more and 2.82 eV (65 kHz/mol) or more. ) or less is more preferable.

The hydrogen atom constituting the general formula (M-1) also includes an isotope of hydrogen (deuterium atom, etc.). In this case, all the hydrogen atoms in the compound may be substituted with a hydrogen isotope, and a mixture may be used in which a part of the hydrogen atom is a compound containing a hydrogen isotope.

The compound represented by the said general formula (M-1) can be synthesize|combined combining various well-known synthesis methods. Most generally, with respect to carbazole compounds, synthesis by dehydrogenation aromatization after aza-Koff rearrangement reaction of a condensate of arylhydrazine and cyclohexane derivative (by LF Tieze, Th. Eicher, Takano, Ogasawara Station, Precision Organics) synthesis, p. 339 (Nankodo Publishing)). In addition, regarding the coupling reaction using the palladium catalyst of the obtained carbazole compound and an aryl halide compound, Tetrahedron Letters 39 vol. 617 (1998), Tetrahedron Letters 39 vol. The method described in Tetrahedron Letters 40 vol. 6393 (1999) etc. is mentioned. It does not specifically limit about reaction temperature and reaction time, The conditions described in the said document are applicable.

It is preferable that the compound represented by the said general formula (M-1) forms a thin layer by a vacuum vapor deposition process, However, wet processes, such as solution application|coating, can also be used suitably. It is preferable that it is 2000 or less from a viewpoint of vapor deposition aptitude or solubility, as for the molecular weight of a compound, it is more preferable that it is 1200 or less, It is especially preferable that it is 800 or less. Further, from the viewpoint of vapor deposition aptitude, when the molecular weight is too small, the vapor pressure becomes small, the change from the gas phase to the solid phase does not occur, and it becomes difficult to form an organic layer. Therefore, 250 or more are preferable, and 300 or more are particularly preferable.

Although the specific example of the 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 (B) cathode 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 the cathode side and transporting them to the anode side. The electron injecting material and the electron transporting material used for these layers may be either a low molecular weight compound or a high molecular compound.

As an electron transport material, the compound represented by the said General formula (1) can be used. Examples of other electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazoles. Aromatics of derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalene, perylene, etc. Various metal complexes represented by metal complexes of cyclic tetracarboxylic acid anhydride, phthalocyanine derivatives, 8-quinolinol derivatives, metal complexes using metal phthalocyanine, benzoxazole or benzothiazole as ligands, and organosilane derivatives represented by silol It is preferable that it is a layer containing a etc.

The thickness of the electron injection layer and the electron transport layer is preferably 500 nm or less, respectively, from the viewpoint of lowering the driving voltage.

As thickness of an electron transport layer, it is preferable that they are 1 nm - 500 nm, It is more preferable that they are 5 nm - 200 nm, It is still more preferable that they are 10 nm - 100 nm. Moreover, as thickness of an electron injection layer, it is preferable that they are 0.1 nm - 200 nm, It is more preferable that they are 0.2 nm - 100 nm, It is still more preferable that they are 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 of the above-mentioned materials, or a multilayer structure composed of multiple layers of the same composition or different compositions.

The electron injection layer preferably contains an electron-donating dopant. By containing an electron-donating dopant in an electron injection layer, there exists an effect, such as an electron injection property improving, a drive voltage falling, and an efficiency improving. The electron-donating dopant may be any of an organic material and an inorganic material as long as it is a material capable of generating radical anions by imparting electrons to the material to be doped. For example, tetrathiafulvarene (TTF), tetratianaphthacene (TTT) and dihydroimidazole compounds such as bis-[1,3-diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, and cesium.

The electron-donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, more preferably 0.1% by mass to 40% by mass, and 0.5% by mass relative to the total mass of the compound forming the electron injection layer. It is more preferable to contain % - 30 mass %.

(B-2) hole block layer

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

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

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

Examples of other organic compounds constituting the hole blocking 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 blocking 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 transporting layer or blocking energy transfer quenching. The compound of the present invention can be preferably applied also as a hole blocking layer.

As thickness of a hole blocking layer, it is preferable that they are 1 nm - 500 nm, It is more preferable that they are 5 nm - 200 nm, It is still more preferable that they are 10 nm - 100 nm.

The hole blocking layer may have a single-layered structure composed of one or two or more of the above-mentioned materials, or a multilayered structure composed of multiple layers of the same composition or different compositions.

(B-3) A material 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 particularly preferably used for the material of the organic layer preferably disposed between the (B) cathode and the light emitting layer, and is a compound represented by the general formula (1), an aromatic hydrocarbon compound (especially , 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 compound]

Although it is more preferable that the said aromatic hydrocarbon compound is contained in the organic layer adjacent to the light emitting layer between a light emitting layer and a cathode, the use is not limited, You may contain further in any layer in an organic layer. As the introduction layer of the aromatic hydrocarbon compound, any or multiple of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton blocking layer, and a charge blocking layer can be included.

The organic layer adjacent to the light emitting layer between the light emitting layer containing the aromatic hydrocarbon compound and the cathode is preferably a charge blocking 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 synthetic|combination easiness.

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. The condensed polycyclic skeleton having 13 to 22 total carbon atoms is preferably any one of fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, and triphenylene, from the viewpoint of _{T 1} fluorene, triphenylene, and phenanthrene are more preferable, and triphenylene is more preferable from the viewpoint of compound stability and charge injection/transportability, and a compound represented by the following general formula (Tp-1) is particularly preferable. .

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

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

[Formula 41]

In the 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 optionally substituted with a triphenylenyl group, a fluorenyl group , a naphthyl group, or a triphenylenyl group. However, ^{none of R 12} to R ²³ becomes a hydrogen atom.

The ^{alkyl group represented by R 12} to R ²³ is a substituted or unsubstituted, for example, methyl group, ethyl group, isopropyl group, n-butyl group, tert-butyl group, n-octyl group, n-decyl group, n-hexade Sil group, cyclopropyl group, cyclopentyl group, cyclohexyl group, etc. are mentioned, Preferably they are a methyl group, an ethyl group, an isopropyl group, tert- butyl group, a cyclohexyl group, More preferably, they are a methyl group, an ethyl group, or tert. -It is a 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, a naphthyl group , or may be substituted with a triphenylenyl group), which may be substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group is more preferable.

It is particularly preferably a benzene ring optionally substituted with a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group (these may also be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group). .

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

R ¹² ~ R ²³ are each independently a small number of bullets is preferred that from 20 to 50, more preferably a small number of bullets of 20 to 36. By setting it as this range, a good quality amorphous thin film can be formed and the solubility with respect to a solvent, sublimation, and vapor deposition titration become favorable.

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

[Formula 42]

In the general formula (Tp-2), a plurality of Ar ¹ are the same and optionally substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group represents the group.

Examples ^{of the alkyl group represented by Ar 1} and the phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group optionally substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group include those listed in R ¹² to R ²³ . The meaning is the same, and the preferable thing is also the same.

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

[Formula 43]

In the general formula (Tp-3), L is a phenyl group optionally substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group, or a combination thereof. represents a linking group. n represents the integer of 1-6.

The alkyl group, phenyl group, fluorenyl group, naphthyl group, or triphenylenyl group forming the n-valent coupling group represented by L has the same meaning as those described for ^{R 12} to R ^{23 .}

L is preferably a benzene ring optionally substituted with an alkyl group or a benzene ring, a fluorene ring, or an n-valent linking group formed by combining them.

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

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

_{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).

From the viewpoint of stably operating the organic electroluminescent device against heat generation during high-temperature driving or device driving, 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, and 100° C. or more and 400° C. It is more preferable that it is below, and it is still more preferable that it is 120 degreeC or more and 400 degrees C or less.

Specific examples of the hydrocarbon compound represented by the general formula (Tp-1)) are exemplified below, but the hydrocarbon compound used in the present invention is not limited thereto.

[Formula 45]

[Formula 46]

The compound exemplified as the hydrocarbon compound represented by the general formula (Tp-1) is, International Publication No. 05/013388 pamphlet, International Publication No. 06/130598 pamphlet, International Publication No. 09/021107 pamphlet, US2009/0009065, International Publication No. It can synthesize|combine by the method of Unexamined-Japanese-Patent No. 09/008311 pamphlet and International Publication No. 04/018587 pamphlet.

It is preferable to refine|purify by sublimation refinement|purification after performing refinement|purification by column chromatography, recrystallization, etc. after a synthesis|combination. By sublimation purification, not only organic impurities can be separated, but also inorganic salts, residual solvents, and the like can be effectively removed.

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

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

[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. n ^O1 represents the integer of 2-6.

R ^O1 represents 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 represent the aforementioned substituent group A you may have R ^O1 is preferably an aryl group or a heteroaryl group, and more preferably an aryl group. When ^{the aryl group of R O1} has a substituent, as a preferable substituent, an alkyl group, an aryl group, or a cyano group is mentioned, An alkyl group or an aryl group is more preferable, and 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 alkyl group or a phenyl group optionally substituted with an aryl group, still more preferably an unsubstituted phenyl group or a 2-phenylphenyl group.

A ^O1 to A ^O4 each independently represent CR ^A or a nitrogen atom. Among A ^O1 -A ^O4 , it is preferable that 0-2 pieces are a nitrogen atom, and it is more preferable that 0 or 1 piece is a nitrogen atom. It is preferable that all of A ^O1 to A ^{O4 are C R A} , or A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are ^{preferably C R A} , it is more preferable that A ^O1 is a nitrogen atom, and A ^O2 to A ^O4 are ^{C R A} More preferably, A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are ^{C R 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), these are the aforementioned 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 a divalent to hexavalent linking group comprising an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). L ^O1 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 above-mentioned substituent Z', and as a substituent in the case of having a substituent, an alkyl group, an aryl group, or a cyano group is preferable. Specific examples of L ^O1 include the following.

[Formula 48]

n ^O1 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 electroluminescent device, and most preferably 2 from the viewpoint of the durability of the organic electroluminescent device.

The compound represented by the general formula (O-1) is more preferably a compound represented by the following general formula (O-2).

[Formula 49]

In general formula (O-2), R ^O1 each 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 the aforementioned substituent group A. R ⁰² to R ⁰⁴ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.

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

Although the specific example of the 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 performed, and then purification by sublimation purification is preferred. By sublimation purification, not only organic impurities can be separated, but also inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the organic electroluminescent device 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 is more preferably contained in the layer on the cathode side adjacent to the light emitting layer.

<protective layer>

In this invention, the whole organic electroluminescent element may be protected by the protective layer.

Regarding the protective layer, the matters described in Paragraph Nos. [0169] to [0170] of Japanese Patent Application Laid-Open No. 2008-270736 are applicable to the present invention. In addition, an inorganic substance may be sufficient as the material of a protective layer, and an organic substance may be sufficient as it.

<Envelope container>

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

Regarding the sealed container, the matter described in Paragraph No. [0171] of JP 2008-270736 A can be applied to the present invention.

<How to drive>

The organic electroluminescent device of the present invention can emit light by applying a direct current (which may contain an alternating current component if necessary) voltage (usually 2 volts to 15 volts) or a direct current between the anode and the cathode.

Regarding the driving method of the organic electroluminescent device 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, Japanese Patent No. 2784615, U.S. Patent No. 5828429, and each specification of U.S. Patent No. 6023308 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 in the vicinity of 300 to 400 cd/m 2 when the device is driven at 20°C can be used.

It is preferable that it is 30 % or more, and, as for the internal quantum efficiency of the organic electroluminescent element of this invention, 50 % or more is more preferable, and 70 % or more is still more preferable. The internal quantum efficiency of the element is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a typical organic EL device, the light extraction efficiency is about 20%, but 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, the light extraction efficiency It is possible to make it into 20% or more.

<Emission wavelength>

In the organic electroluminescent device of the present invention, the emission wavelength is not limited. For example, among the three primary colors of light, it may be used for light emission of red, may be used for light emission of green, and may be used for light emission of blue. Among them, the organic electroluminescent device of the present invention preferably has an emission peak wavelength of 490 to 580 nm from the viewpoint of luminous efficiency in consideration _{of the lowest triplet excitation (T 1 ) energy of the compound represented by the general formula (1).} .

Specifically, in the organic electroluminescent device of the present invention, when the compound represented by the general formula (1) is used as a host material for a light emitting layer, an electron transport layer or an electron transport material for a hole blocking 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 the organic electroluminescent device of the present invention>

The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a read light source, a sign, a signboard, an interior, or optical communication. In particular, it is preferably used for devices driven in a region with high emission luminance, such as a light emitting device, a lighting device, and a display device.

[Light-emitting device]

The light emitting device of the present invention comprises 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 .

Fig. 2 is a cross-sectional view schematically showing an example of a 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.

The organic electroluminescent element 10 is constituted 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 negative electrode 9, and the sealing container 16 is formed on the protective layer 12 through the contact bonding layer 14 interposing. In addition, a part of each electrode 3, 9, a partition, an insulating layer, etc. are abbreviate|omitted.

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

The use in particular of the light emitting device of this invention is not restrict|limited, For example, it can be set as display apparatuses, such as a television, a personal computer, a mobile phone, and electronic paper, in addition to a lighting device.

[Lighting Device]

The lighting device of the present invention is characterized by including the organic electroluminescent element of the present invention.

Next, a lighting device of the present invention will be described with reference to FIG. 3 .

Fig. 3 is a cross-sectional view schematically showing an example of the lighting device 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 device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 contact each other.

The light scattering member 30 is not particularly limited as long as it can scatter light. 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. Any well-known thing can be used as a glass substrate and transparent resin microparticles|fine-particles. In such a lighting device 40 , when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30 , the incident light is scattered by the light scattering member 30 and scattered Light is emitted as illumination light from the light exit surface 30B.

[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 sets it as display apparatuses, such as a television, a personal computer, a mobile phone, and electronic paper, etc. are mentioned, for example.

Example

Hereinafter, the present invention will be described in more detail with reference to Examples. Materials, amounts used, ratios, processing contents, processing 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 examples shown below.

[Examples 1 to 6]

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

compound 1B-2

1H-NMR (solvent): heavy DMSO, standard: tetramethylsilane) δ (ppm)

Compound 1B-3

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

Compound 1B-4

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

Compound 1B-17

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

compound 1D-1

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

compound 1D-3

1H-NMR (solvent): heavy 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 Comparative Compounds 1-4 in which some structures are similar were carried out similarly to the said compound 1B-2, and were synthesize|combined.

2. Fabrication and evaluation of organic electroluminescent devices

(2-A) Preparation of green phosphorescent organic electroluminescent device-1

All materials used for organic electroluminescent device manufacture were previously subjected to sublimation purification.

[Comparative Example 1]

(Manufacture of anode)

A glass substrate having an ITO film having a thickness of 0.5 mm and an ITO film of 2.5 cm in width (manufactured by Geomatech Co., Ltd., surface resistance of 10 Ω/□) was placed in a cleaning container, and after ultrasonic cleaning in 2-propanol, UV-ozone treatment was performed for 30 minutes. .

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

(Lamination of organic layers)

The organic layers of the first to fifth layers were sequentially deposited on the anode by vacuum evaporation using the following compounds. In addition, the structure of the compound used for each layer was shown.

1st layer: LG101: film thickness 10 nm

2nd 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

4th layer: TpH-17: film thickness 10 nm

5th layer: Alq: film thickness 40 nm

[Formula 54]

(Production of cathode)

On this, 0.1 nm of lithium fluoride and 200 nm of metallic aluminum were vapor-deposited in this order, and it was set as the cathode.

(Production of organic electroluminescence)

The laminate having five organic layers between the cathode and the anode was placed in a glove box substituted with nitrogen gas without contact with the atmosphere, and a glass encapsulation can and UV-curable adhesive (XNR5516HV, manufactured by Nagase Chiba Co., Ltd.) It was used and sealed, and the organic electroluminescent element of Comparative Example 1 was obtained.

(Evaluation of organic electroluminescent device)

(a) Durability

The organic electroluminescent device of Comparative Example 1 was continuously emitting light by applying a DC voltage so that the luminance became 5000 cd/m 2 at room temperature, and the time required until the luminance reached 4000 cd/m 2 was measured. This time was used as an index of durability of the organic electroluminescent device.

In addition, in each Example and Comparative Example to be described later, in Table 1 described below, durability when the organic electroluminescent device of Comparative Example 1 is used is 100, and the relative value of durability is less than 100 ×, 100 The thing of 150 or more was made into (circle) and the thing 150 or more was made into (double-circle).

Here, the durability is more preferable as the number increases.

(b) Chromaticity difference after high temperature storage

After high-temperature storage (48 hours at 100°C) and before storage, a DC voltage was applied to the organic electroluminescent device of Comparative Example 1 so that the luminance was 1000 cd/m 2 , and an emission spectrum measurement system manufactured by Shimadzu Corporation (Co., Ltd.) ELS1500) was used to measure the emission spectrum, and the chromaticity (CIE chromaticity) was calculated.

When the chromaticity after storage at high temperature (48 hours at 100°C) differs by 0.01 or more in either the x or y coordinates from before storage and the CIE (x, y) coordinates ×, all 0.005 or more and less than 0.01 ○, all less than 0.005 The thing was marked with (double-circle).

(c) glass transition temperature

The glass transition temperature of Comparative Compound 1 used as a host material in the third layer of the organic layer was measured by differential scanning calorimetry (DSC).

The results are shown in Table 1 below with a glass transition temperature Tg of less than 100°C as ×, 100°C or more and less than 120°C as ○, and 120°C or more as (double-circle).

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

As a material for the third layer of the organic layer in Comparative Example 1, in the same manner as in Comparative Example 1, except that the compound represented by the general formula (1) shown in Table 1 below or Comparative Compounds 2 to 4 was used instead of the comparative compound 1. Thus, the organic electroluminescent devices of Examples A1 to A9 and Comparative Examples 2 to 4 were obtained.

In addition, Comparative Compound 1 is a compound compound 2S described in International Publication No. WO2009/073245, Comparative Compound 3 is a compound compound 2S described in International Publication No. WO2009/021126, Comparative Compound 4 is a compound compound described in International Publication No. WO2009/021126 It is 9S.

[Formula 55]

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

From Table 1 above, the organic electroluminescent devices of each Example using the compound represented by the general formula (1) of Examples A1 to A9 as the host compound of the light emitting layer all had good durability and chromaticity difference after high temperature storage. . Moreover, the compound represented by General formula (1) of these Examples A1-A9 had high glass transition temperature and was favorable.

On the other hand, in the organic electroluminescent devices of Comparative Examples 1, 2 and 4, Comparative Compounds 1, 2 and 4 were used as host compounds of the light emitting layer, and it was found that the durability was poor. In the organic electroluminescent device of Comparative Example 3, Comparative Compound 3 was used as the host compound of the light emitting layer, and it was found that the difference in chromaticity after storage at a high temperature was bad. Moreover, Comparative Compounds 1 to 3 used in Comparative Examples 1 to 3 had a low glass transition temperature.

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

(2-B) Preparation of green phosphorescent organic electroluminescent device-2

[Comparative Example 5]

With respect to the organic layer of the organic electroluminescent device of Comparative Example 1, in the same manner as in Comparative Example 1, except that NPD used for the second layer was replaced with HTL-1, and GD-1 used for the third layer was replaced with GD-2. Thus, an organic electroluminescent device of Comparative Example 5 was obtained. The structure of the organic layer in Comparative Example 5 is shown below.

1st layer: LG101: film thickness 10 nm

2nd 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

4th layer: TpH-17: film thickness 10 nm

5th layer: Alq: film thickness 40 nm

[Formula 56]

[Examples B1 to B4, Comparative Example 6]

Examples B1 to B4 and Comparative Example 5 were carried out in the same manner as in Comparative Example 5 except that the compound represented by the general formula (1) and Comparative Compound 3 were used instead of Comparative Compound 1 as a material for the third layer of the organic layer in Comparative Example 5. The organic electroluminescent element of Example 6 was obtained.

The organic electroluminescent devices of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability when the organic electroluminescent element of Comparative Example 5 is used as a criterion for evaluation of durability is 100, and the relative value of the durability of the organic electroluminescent element of each other Example and Comparative Example is less than 100 ×, 100 or more Those less than 150 were evaluated as (circle), and those of 150 or more were evaluated as (double-circle).

The results are shown in Table 2 below.

From Table 2, the organic electroluminescent device of each Example using the compound represented by the general formula (1) of Examples B1 to B6 as the host compound of the light emitting layer all had good durability and chromaticity difference after high temperature storage. .

On the other hand, in the organic electroluminescent device of Comparative Example 5, Comparative Compound 1 was used as the host compound of the light emitting layer, and it was found that the durability was poor. 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 difference in chromaticity after storage at a high temperature was poor.

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

(2-C) Preparation of organic electroluminescent device of red phosphorescence emission

[Comparative Example 7]

With respect to the organic layer of the organic electroluminescent device of Comparative Example 1, LG101 used for the first layer was replaced with GD-1, GD-1 used for the third layer was replaced with red phosphorescent 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 in Alq was replaced with Alq. The structure of the organic layer in Comparative Example 7 is shown below.

1st layer: GD-1: film thickness 10 nm

2nd 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

4th layer: Alq: film thickness 10 nm

5th layer: Alq: film thickness 40 nm

[Formula 57]

[Examples C1 to C3, Comparative Example 8]

Examples C1 to C6 and Examples C1 to C6 and An organic electroluminescent device of Comparative Example 8 was obtained.

The organic electroluminescent devices of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability when the organic electroluminescent device of Comparative Example 7 is used as a criterion for evaluation of durability is 100, and the relative value of the durability of the organic electroluminescent devices of other Examples and Comparative Examples is less than 100 ×, 100 or more Those less than 150 were evaluated as (circle), and those of 150 or more were evaluated as (double-circle).

The results are shown in Table 3 below.

From Table 3 above, it was found that the organic electroluminescent devices of each Example using the compound represented by the general formula (1) of Examples C1 to C3 as the host compound of the light emitting layer had good durability and chromaticity difference after high temperature storage. .

On the other hand, in the organic electroluminescent device of Comparative Example 7, Comparative Compound 1 was used as the host compound of the light emitting layer, and it was found that the durability was poor. 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 difference in chromaticity after storage at a high temperature was bad.

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

(2-D) Preparation of green phosphorescent organic electroluminescent device-3

[Comparative Example 9]

A device of Comparative Example 9 was manufactured 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, and Alq used for the fifth layer was replaced with OM-8. . The structure of the organic layer in Comparative Example 9 is shown below.

1st layer: LG101: film thickness 10 nm

2nd 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

4th layer: OM-8: film thickness 10 nm

5th layer: OM-8: film thickness 40 nm

[Formula 58]

[Examples D1 to D5, Comparative Example 10]

Examples D1 to D5 and Examples D1 to D5 and An 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 devices of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability when the organic electroluminescent device of Comparative Example 9 is used as a criterion for evaluation of durability is 100, and the relative value of the durability of the organic electroluminescent devices of other Examples and Comparative Examples is less than 100 ×, 100 or more Those less than 150 were evaluated as (circle), and those of 150 or more were evaluated as (double-circle).

The results are shown in Table 4 below.

From Table 4, the organic electroluminescent device of each Example using the compound represented by the general formula (1) of Examples D1 to D5 as the host compound of the light emitting layer all had good durability and chromaticity difference after high temperature storage. .

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

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

(2-E) Preparation of green phosphorescent organic electroluminescent device-4

(Comparative Example 11)

A device of Comparative Example 11 was manufactured in the same manner as in Comparative Example 4 except that TpH-17 used for 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 Comparative Example 11 is shown below.

1st layer: LG101: film thickness 10 nm

2nd 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 of 10 nm

5th layer: OM-8: film thickness 40 nm

[Formula 59]

[Examples E1 to E3, Comparative Example 12]

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

The organic electroluminescent devices of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. In addition, the durability when the organic electroluminescent device of Comparative Example 11 is used as a criterion for evaluation of durability is 100, and the relative value of the durability of the organic electroluminescent devices of other Examples and Comparative Examples is less than 100 ×, 100 or more Those less than 150 were evaluated as (circle), and those of 150 or more were evaluated as (double-circle).

The results are shown in Table 5 below.

From Table 5, the organic electroluminescent device of each Example using the compound represented by the general formula (1) of Examples E1 to E3 as the host compound of the light emitting layer and the fourth layer of the organic layer has good durability and chromaticity difference after high temperature storage could see that

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

In addition, the 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 electroluminescent device (organic EL device)
11 … organic layer
12 … protective layer
14 … adhesive layer
16 … bag container
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 (9)

A compound represented by the general formula (1) is included;
disposed adjacent to the cathode between a pair of electrodes included in the organic electroluminescent device
electron transport layer.
General formula (1)

In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (however, an alkyl group and a cyano group are excluded), and a plurality of R ¹⁰⁸ to R ¹¹⁰ are They may be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group. According to claim 1,
The electron transport layer characterized in that the compound represented by the general formula (1) is a compound represented by the following general formula (2) or (3).
general formula (2)

In general formula (2),
X ²⁰¹ represents an oxygen atom or a sulfur atom,
R ²⁰¹ to R ²¹² each independently represents a hydrogen atom, an aryl group or a heteroaryl group,
A plurality of R ²⁰⁸ and R ²⁰⁹ may be the same or different from each other,
L ²⁰¹ represents an arylene group other than a single bond or a p-terphenylene group,
One of A ²⁰¹ and A ²⁰² is a condensed aryl group having 10 to 30 ring atoms, a condensed heteroaryl group having 8 to 30 ring atoms, an aryl group having 6 to 25 carbon atoms having these as a substituent, or an aryl group having 5 to 25 ring atoms A heteroaryl group or a monocyclic heteroaryl group having 5 to 25 ring atoms having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.
general 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,
A plurality of R ³⁰⁸ to R ³¹² may be the same or different from each other,
L ³⁰¹ represents a single bond or an arylene group,
One of A ³⁰¹ and A ³⁰² is a condensed aryl group having 10 to 30 ring atoms, a condensed heteroaryl group having 8 to 30 ring atoms, an aryl group having 6 to 25 carbon atoms having these as a substituent, or an aryl group having 5 to 25 ring atoms A heteroaryl group or a monocyclic heteroaryl group having 5 to 25 ring atoms having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group. According to claim 1,
The electron transport layer characterized in that the compound represented by the general formula (1) is a compound represented by one of the following general formulas (4) to (7).

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

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

In general formula (6),
X ⁶⁰¹ and X ⁶⁰² each independently represents 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,
A plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same as or different from each other.

In general formula (7),
X ⁷⁰¹ represents an oxygen atom or a sulfur atom,
R ⁷⁰¹ to R ⁷¹⁶ each independently represents a hydrogen atom, an aryl group or a heteroaryl group,
A plurality of R ⁷⁰⁸ to R ⁷¹⁶ may be the same as or different from each other. According to claim 1,
The electron transport layer characterized in that the compound represented by the general formula (1) is a compound represented by one of the following general formulas (8) to (11).

In general formulas (8) to (11),
X ⁸⁰¹ to X ⁸⁰⁶ each independently represents an oxygen atom or a sulfur atom,
R ⁸⁰¹ to R ⁸⁰⁶ each independently represents 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 of them is a nitrogen atom. A compound represented by the general formula (1) is included;
disposed adjacent to the opposite side of the cathode of the electron transport layer disposed adjacent to the cathode between a pair of electrodes included in the organic electroluminescent device
hole block layer.
General formula (1)

In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represents a hydrogen atom or a substituent (however, an alkyl group and a cyano group are excluded), and a plurality of R ¹⁰⁸ to R ¹¹⁰ are They may be the same as or different from each other, and L ¹⁰¹ represents a single bond or an arylene group. 6. The method of claim 5,
The compound represented by general formula (1) is a compound represented by following general formula (2) or (3), The hole blocking layer characterized by the above-mentioned.
general formula (2)

In general formula (2),
X ²⁰¹ represents an oxygen atom or a sulfur atom,
R ²⁰¹ to R ²¹² each independently represents a hydrogen atom, an aryl group or a heteroaryl group,
A plurality of R ²⁰⁸ and R ²⁰⁹ may be the same or different from each other,
L ²⁰¹ represents an arylene group other than a single bond or a p-terphenylene group,
One of A ²⁰¹ and A ²⁰² is a condensed aryl group having 10 to 30 ring atoms, a condensed heteroaryl group having 8 to 30 ring atoms, an aryl group having 6 to 25 carbon atoms having these as a substituent, or an aryl group having 5 to 25 ring atoms A heteroaryl group or a monocyclic heteroaryl group having 5 to 25 ring atoms having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group.
general 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,
A plurality of R ³⁰⁸ to R ³¹² may be the same or different from each other,
L ³⁰¹ represents a single bond or an arylene group,
One of A ³⁰¹ and A ³⁰² is a condensed aryl group having 10 to 30 ring atoms, a condensed heteroaryl group having 8 to 30 ring atoms, an aryl group having 6 to 25 carbon atoms having these as a substituent, or an aryl group having 5 to 25 ring atoms A heteroaryl group or a monocyclic heteroaryl group having 5 to 25 ring atoms having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent is represented, and the other represents a hydrogen atom, an aryl group or a heteroaryl group. 6. The method of claim 5,
The hole blocking layer characterized in that the compound represented by the general formula (1) is a compound represented by one of the following general formulas (4) to (7).

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

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

In general formula (6),
X ⁶⁰¹ and X ⁶⁰² each independently represents 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,
A plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same as or different from each other.

In general formula (7),
X ⁷⁰¹ represents an oxygen atom or a sulfur atom,
R ⁷⁰¹ to R ⁷¹⁶ each independently represents a hydrogen atom, an aryl group or a heteroaryl group,
A plurality of R ⁷⁰⁸ to R ⁷¹⁶ may be the same as or different from each other. 6. The method of claim 5,
The compound represented by the general formula (1) is a compound represented by one of the following general formulas (8) to (11).

In general formulas (8) to (11),
X ⁸⁰¹ to X ⁸⁰⁶ each independently represents an oxygen atom or a sulfur atom,
R ⁸⁰¹ to R ⁸⁰⁶ each independently represents 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 of them is a nitrogen atom. The electron transport layer of any one of claims 1 to 4, the hole blocking layer of any one of claims 5 to 8, or the electron transport layer of any one of claims 1 to 4, and claims 5 to 8 Including an organic electroluminescent device having a hole blocking layer of any one of claims
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