KR20180118815A - Organic electroluminescent element, light-emitting device using organic electroluminescent element, display device using organic electroluminescent element, lighting device using organic electroluminescent element, and compound for organic electroluminescent element - Google Patents

Abstract

An organic electroluminescent device comprising a substrate, a pair of electrodes disposed on the substrate, the pair of electrodes including an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer comprises an organic electroluminescent material containing a phosphorescent material and a compound represented by the following formula (Wherein X ¹⁰¹ represents an oxygen atom or a sulfur atom, and R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (excluding an alkyl group and a cyano group) And a plurality of R ¹⁰⁸ to R ¹¹⁰ may be the same or different, and L ¹⁰¹ represents a single bond or an arylene group.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device, a light emitting device using the same, a display device, a lighting device, and a compound thereof. BACKGROUND OF THE INVENTION [0001] The present invention relates to an organic electroluminescent device and an organic electroluminescent device. , AND COMPOUND FOR ORGANIC ELECTROLUMINESCENT ELEMENT}

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

BACKGROUND ART [0002] Organic electroluminescent devices (hereinafter also referred to as " devices ", also referred to as " organic EL devices ") have been actively researched and developed in that high- The organic electroluminescent device has an organic layer between a pair of electrodes, and the electrons injected from the cathode and the excitons generated by recombination of holes injected from the anode in the organic layer are used for light emission.

In recent years, the use of a phosphorescent material has led to an increase in the efficiency of an organic electroluminescent device. However, improvement in durability and the like is required in practical use. The use of a dibenzothiophene charge-transporting material is described in Patent Document 1 in order to improve the luminous efficiency of an additional element and improve the durability of the element. An organic electroluminescent device using a compound in which dibenzothiophene and triphenylene are connected with a phenyl group is described in Patent Document 2. An organic electroluminescent device using a compound in which dibenzothiophene is linked with a phenyl group is described in Patent Documents 3 and 4.

On the other hand, various display devices including organic electroluminescent devices have been widely used in recent years, and it is demanded to stably operate for a long time under various environments. For example, it is required to have a long lifetime (so-called durability) in automobile use for automobiles and the like. In addition, since the interior temperature of the vehicle is considerably high at the time of driving or parking, Is also required. It is also important that the organic electroluminescent device does not change in characteristics after storage at such a high temperature, even when the organic electroluminescent device emits heat at the same level as that of the conventional light emitting device.

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

As a result of examining the characteristics of the organic electroluminescent device described in Patent Documents 1 to 4 by the inventors of the present invention, it has been found that the conventional organic electroluminescent device is still unsatisfactory in durability, .

Thus, as a result of changing the compound used in the organic layer, it was found that the durability and the chromaticity difference at the time of high-temperature storage change to some extent. Therefore, as a result of further studies on the compound used in the organic layer, it has been found that even if the molecular weight of the compound used in the organic layer is simply increased, the durability and the chromaticity difference during storage at high temperature are not improved. For example, the compound 9S described in Patent Document 2 has a lower chromaticity difference at the time of storage at high temperature than the compound 2S having a smaller molecular weight and a lower glass transition temperature than the compound, but the durability is lowered. That is, it has been found that it is difficult to improve the durability and the chromaticity difference at the time of high-temperature storage by changing the compound used in the organic layer.

An object of the present invention is to provide an organic electroluminescent device having excellent durability and having a small difference in chromaticity at high temperature storage.

As a result of extensive studies by the present inventors, it has been found that by using a compound containing a dibenzothiophene structure or a dibenzofuran structure and a p-terphenylene structure, it is possible to provide an organic electroluminescent device having excellent durability, Device is provided.

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

[1] A light-emitting device comprising a substrate, a pair of electrodes disposed on the substrate, the pair of electrodes including an anode and a cathode, and an organic layer disposed between the electrodes, And a compound represented by the following general formula (1).

In general formula (1)

[Chemical Formula 1]

(In the general formula (1), 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 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.

At least one R ^{110 in} the general formula (1) is a condensed ring aryl group having 10 to 30 ring atoms, a condensed ring heteroaryl group having 8 to 30 ring atoms, a carbon number A heteroaryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms 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, Or the organic electroluminescent element described in [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)

In general formula (2)

(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 and or different. L ²⁰¹ represents a single bond or an arylene group denotes, p- terphenyl alkylene group is not. a ²⁰¹ and a ²⁰² is one of the aryl groups can be ring atoms of 10 to 30 fused ring, fused rings of ring atoms An aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, And one of the other represents a hydrogen atom, an aryl group or a heteroaryl group.

In general formula (3)

(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 and or different. L ³⁰¹ represents a single bond or an arylene represents a group. a ³⁰¹ and one of a ³⁰² is fused an aryl group of ring of ring atoms, of 10 to 30, fused ring of the heteroaryl in the number ring atoms 8-30 group , An aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms or a monocyclic heteroaryl group having 5 to 25 ring atoms and having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent , And the other one 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 represented by any one of the following general formulas (4) to (7)

[Chemical Formula 4]

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

[Chemical Formula 5]

(In the general formula (5), X ⁵⁰¹ represents an oxygen atom or a sulfur atom, and R ⁵⁰¹ to R ⁵¹³ each independently represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁵⁰⁸ to R ⁵¹³ And n ₅₀₁ represents 0 or 1.)

[Chemical Formula 6]

(Formula (6) of the, X ⁶⁰¹ and X ⁶⁰² each independently represents an oxygen atom or a sulfur atom. R ⁶⁰¹ ~ R ⁶²¹ each independently represents a hydrogen atom, an aryl group or a heteroaryl group, a plurality of R ⁶⁰⁸ ~ R ⁶¹³ may be the same or different.)

(7)

(Compound 7 of, X ⁷⁰¹ represents an oxygen atom or a sulfur atom. R ⁷⁰¹ ~ R ⁷¹⁶ each independently represents a hydrogen atom, an aryl group or a heteroaryl group, a plurality of R ⁷⁰⁸ ~ R ⁷¹⁶ may be the same with 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 formula (E-1).

[Chemical 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 forming a 5 or 6-membered heterocyclic ring together with Z ¹ and a nitrogen atom (XY) represents a monoanionic two-dimensional ligand, and n _E1 represents an integer of 1 to 3, provided that at least _one of R ₁ , R ² , R ³ , R ⁴ , R 5, )

[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).

[Chemical Formula 9]

(E-2), each of A ^E1 to A ^E8 independently represents a nitrogen atom or a carbon atom substituted by R ^E , R ^E represents a hydrogen atom or a substituent, (XY) represents a monoanionic And n _E2 represents an integer of 1 to 3.)

[10] The organic electroluminescent device according to any one of [1] to [9], wherein the organic layer has the light emitting layer containing the phosphorescent material and the other organic layer, and the light emitting layer contains the compound represented by the general formula Lt; RTI ID = 0.0 > 1, < / RTI >

(11) The organic electroluminescent device according to any one of the above (1) to (11), wherein the organic layer has a light emitting layer containing the phosphorescent material and another organic layer and the other organic layer is disposed between the light emitting layer and the cathode, The organic electroluminescent device according to any one of [1] to [10], wherein the organic electroluminescent device comprises a compound represented by the formula [1].

[12] The organic electroluminescent device according to any one of [1] to [10], wherein the electron transport layer or the hole blocking layer has an electron transport layer adjacent to the cathode between the pair of electrodes and optionally has a hole blocking layer adjacent to the opposite side of the cathode, The organic electroluminescent device described in any one of [1] to [11], which contains a compound represented by the formula (1).

[13] The organic electroluminescent device according to any one of [1] to [12], wherein the organic layer disposed between the pair of electrodes comprises a layer formed by vapor deposition of a composition containing at least one compound represented by the general formula (1) The organic electroluminescent element according to any one of claims 1 to 5.

[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 one of the following general formulas (8) to (11).

[Chemical formula 10]

(In 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 represent a hydrogen atom or an aryl group having 6 to 13 carbon atoms. A ¹¹ to A ¹³ each independently represents CH or a nitrogen atom, and at least one of them is a nitrogen atom.)

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

Further, according to the present invention, it is possible to provide a compound useful as an organic electroluminescent device as a charge transport material and a host material of a light emitting layer, and to provide a light emitting device, a display device and a lighting device using the organic electroluminescent device have.

1 is a schematic diagram showing an example of the configuration of an organic electroluminescent device according to the present invention.
2 is a schematic view showing an example of a light emitting device related to the present invention.
3 is a schematic view showing an example of a lighting apparatus according to the present invention.
4 is a ¹ H-NMR spectrum diagram of Compound 1B-2 of the present invention.
5 is a ¹ H-NMR spectrum diagram of Compound 1B-3 of the present invention.
6 is a ¹ H-NMR spectrum 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 contents of the present invention will be described in detail. The description of constituent elements described below may be made based on a representative embodiment of the present invention, but the present invention is not limited to such embodiment. In the present specification, " " is used to mean that the numerical values described before and after the lower limit and the upper limit are included.

[Organic electroluminescent device]

An organic electroluminescent device of the present invention comprises a substrate, a pair of electrodes disposed on the substrate, the organic electroluminescent material comprising a pair of electrodes including an anode and a cathode, and an organic layer disposed between the electrodes, And contains a compound represented by the formula (1).

In general formula (1)

(11)

(In the general formula (1), 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 or different, and L ¹⁰¹ represents a single bond or an arylene group.

In the organic electroluminescent device, electrons are injected from a cathode, holes are injected from an anode, and they recombine in an organic layer (sometimes referred to as a light-emitting layer in terms of function) while moving on an organic molecule. The light emitting material emits light by using the excitation energy generated at that time. Therefore, in consideration of the lifetime (durability) of the organic electroluminescent device, the stability of the material is important. Particularly, since the charge (electron or hole) moves on the material phase, the stability of the material against electric charge (= stability in the radical state) is very important. Although not wishing to be bound by any theory, in the present invention, it has been found that by using a compound having a p-terphenyl structure introduced, the spin density distribution in a radical state can be more widely non-localized than other phenyl groups or biphenyl groups. Here, as the spin density distribution is diffused, the radical species is thermodynamically stabilized. Therefore, it is considered that dibenzothiophene or dibenzofuran derivatives having a p-terphenyl structure can secure high stability in a radical state. As a result, it is considered that the durability of the organic electroluminescent device can be remarkably improved. In addition, the compound having a p-terphenyl structure introduced therein has a smaller number of movable sites than the m-terphenyl structure, for example, and can prevent the change in film quality of the organic layer at high temperatures. Therefore, And the difference in chromaticity after storage could be reduced.

The structure of the organic electroluminescent device of the present invention is not particularly limited. Fig. 1 shows an example of the structure of the organic electroluminescence device of the present invention. The organic electroluminescent device 10 of Fig. 1 has an organic layer between a pair of electrodes (anode 3 and cathode 9) on a substrate 2. [

The structure of the organic electroluminescent device, the substrate, the cathode, and the anode are described in detail in, for example, Japanese Patent Laid-Open Publication No. 2008-270736, and the matters described in the publication can be applied to the present invention.

Hereinafter, preferred embodiments of the organic electroluminescent device of the present invention will be described in detail in the order of a substrate, an electrode, an organic layer, a protective layer, a sealing container, a driving method, an emission wavelength, and application.

<Substrate>

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

The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the 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 processability.

<Electrode>

The organic electroluminescent device of the present invention has a pair of electrodes disposed on the substrate and including an anode and a cathode.

It is preferable that at least one of the positive electrode and the negative electrode, which are a pair of electrodes, is transparent or semitransparent in nature of the light emitting element.

(anode)

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

(cathode)

The shape of the cathode is not particularly limited as long as it has a function as an electrode for injecting electrons into the organic layer. The shape, structure, size and the like of the cathode are not particularly limited and can be appropriately selected from known electrode materials according to the purpose and purpose of the light emitting element.

<Organic layer>

The organic electroluminescent device of the present invention has an organic layer disposed between the electrodes, and the organic layer contains a phosphorescent material and a compound represented by the general formula (1).

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

The shape, size, and thickness of the organic layer are not particularly limited and may be appropriately selected according to the purpose.

Hereinafter, the structure of the organic layer, the method of forming the organic layer, the preferred embodiment of each layer constituting the organic layer, and the material used for each layer in the organic electroluminescent device of the present invention will be described 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 injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, or an electron injecting layer may be mentioned. If the charge transporting layer is a hole injecting layer, a hole transporting layer, an electron blocking layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent device having a low cost and a high efficiency.

In the organic electroluminescent device of the present invention, it is preferable that the organic electroluminescent device has a luminescent layer containing the phosphorescent material and another organic layer, and the luminescent layer contains the compound represented by the general formula (1). Further, in the organic electroluminescent device of the present invention, it is more preferable that the organic layer has a luminescent layer containing the phosphorescent material and another organic layer. However, even when the organic layer has a light emitting layer and other organic layers, the organic electroluminescent device of the present invention does not necessarily have to be clearly distinguished between the layers.

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 particular limitation on the place where the phosphorescent material and the compound represented by the general formula (1) are contained. In the present invention, it is more preferable that the organic layer has a light-emitting layer containing the phosphorescent material and other organic layers, and the light-emitting layer contains the compound represented by the general formula (1). At this time, it is preferable that the compound represented by the general formula (1) is used as a host compound in the light emitting layer.

The electron transport layer or the hole blocking layer may optionally include a hole blocking layer adjacent to the negative electrode of the electron transporting layer between the pair of electrodes and having an electron transporting layer adjacent to the cathode, (1). &Lt; / RTI &gt;

These organic layers may be formed in plural layers or in the case of forming a plurality of layers, they may be formed of the same material or may be formed of different materials for each layer.

(Method of forming organic layer)

In the organic electroluminescent device of the present invention, each of the organic layers may be formed by any of a dry film forming method such as a vapor deposition method and a sputtering method, a wet film forming method such as a transfer method, a printing method, a spin coat method, and a bar coat method Can be preferably formed.

The organic electroluminescent device of the present invention preferably includes a layer formed by vapor deposition of a composition containing at least one compound represented by the above general formula (1) in an organic layer disposed between the pair of electrodes.

(Light emitting layer)

The light emitting layer has a function of receiving holes from an anode, a hole injecting layer, or a hole transporting layer when an electric field is applied, receiving electrons from a cathode, an electron injecting layer, or an electron transporting layer and providing a place for recombination of holes and electrons to emit light . However, the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism. The light emitting layer in the organic electroluminescent device of the present invention preferably contains at least one kind of the above phosphorescent material.

The light-emitting layer in the organic electroluminescent device of the present invention may be composed of only the phosphorescent material, or may be a mixed layer of the host material and the phosphorescent material. The phosphorescent material may be one kind or two or more kinds. The host material is preferably a charge transporting material. The host material may be one kind or two kinds or more, and may be, for example, a mixture of a host material of electron transporting property and a host material of hole transporting property. The light-emitting layer may contain a material that does not have charge transportability and does not emit light.

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

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

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 the compound represented by the general formula (1) is more preferably used as the host material of the light emitting layer Lt; / RTI &gt; Here, in the present specification, the host material is a compound which mainly takes charge of charge injection and transport in the light emitting layer, and is a compound which does not substantially emit light itself. Here, the phrase &quot; substantially does not emit light &quot; means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less, % Or less.

Hereinafter, as the material of the light emitting layer, other host materials other than the compound represented by the general formula (1), the phosphorescent light emitting material and the compound represented by the general formula (1) will be described in order. The compound represented by the above general formula (1) may be used in addition to the above-described light emitting layer in the organic electroluminescent device of the present invention.

(1) a compound represented by the above general formula (1)

Hereinafter, the compound represented by the following general formula (1) will be described.

In general formula (1)

[Chemical Formula 12]

(In the general formula (1), 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 L &lt; ¹⁰¹ &gt; represents a single bond or an arylene group.

In the present invention, the hydrogen atom in the description of the general formula (1) also includes a isotope (deuterium atom, etc.), and further, the atom constituting the substituent also includes the isotope.

In the present invention, when a "substituent" is mentioned, the substituent may be substituted. For example, the term &quot; alkyl group &quot; in the present invention includes an alkyl group substituted with a fluorine atom (e.g., trifluoromethyl group) or an alkyl group substituted with an aryl group (e.g., triphenylmethyl group) Quot; denotes an alkyl group having 1 to 6 carbon atoms &quot;, all groups including a substituted group indicate 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 large van der Waals radius is preferable in terms of improvement of electron mobility.

The substituent represented by R ¹⁰¹ to R ^{110 in} the general formula (1) is a substituent except for an alkyl group and a cyano group, and each independently includes the following substituent group A, and the substituent may further have a substituent . Examples of the additional substituent include groups selected from the substituent group A above.

"Substituent group A"

(Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl and the like) An alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as propargyl and 3-pentynyl) , An aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 14 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthryl and the like An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, Diphenylamino, ditolylamino, etc.), (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as phenyloxy, 1-naphthyloxy, 2- Naphthyloxy and the like), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as pyridyloxy, (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, For example, acetyl, benzoyl, formyl, pivaloyl and the like), An alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl and the like), aryl An oxycarbonyl group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl), an acyloxy group (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoyloxy and the like), an acylamino group , More preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino), an alkoxycarbonylamino group (preferably having 2 carbon atoms (Preferably having 7 to 30 carbon atoms, more preferably 7 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino), an aryloxycarbonylamino group , More preferably 7 to 20 carbon atoms, and particularly preferably 7 to 12 carbon atoms such as phenyloxycarbonylamino), a sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms, (Preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino), a sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably (Preferably having from 1 to 20 carbon atoms, more preferably from 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl and the like), a carbamoyl group 3 More preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl and phenylcarbamoyl) Alkylthio groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio and the like), arylthio groups (Preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, particularly preferably a carbon number of 6 to 12, such as phenylthio, etc.), a heterocyclic thio group Preferably 1 to 20 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2- , A sulfonyl group (preferably a carbon number &lt; RTI ID = 0.0 &gt; (Preferably having 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl) (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl) (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido and phenylureido) A halogen atom (e.g., a fluorine atom, a chlorine atom, a chlorine atom, a chlorine atom, a bromine atom, a chlorine atom, or a bromine atom), preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, Atoms, bromine atoms, iodine (Preferably having 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms, more preferably 1 to 30 carbon atoms), a sulfonyl group, a carboxyl group, a nitro group, a hydroxyl group, a sulfino group, a hydrazino group, 1 to 12, and the heteroatom includes, for example, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom and a tellurium atom and specifically includes pyridyl, pyrazinyl, pyrimidinyl, , Pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, telulophenyl, piperidyl, Benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, and silylyl group), a silyl group (preferably a silyl group), a heterocyclic group Preferably has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, (Preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl and triphenylsilyl), a silyloxy group (For example, a diphenylphosphoryl group, a dimethylphosphoryl group and the like) may be substituted with an alkyl group having 1 to 20 carbon atoms such as trimethylsilyloxy, triphenylsilyloxy and the like) . These substituents may be further substituted, and examples of the additional substituent include groups selected from Substituent Group A described above.

Each of R ¹⁰¹ to R ¹¹⁰ is independently 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, and particularly preferably 6 to 18 carbon atoms, and examples thereof include a phenyl group, a xylyl group, a biphenyl group, , Naphthyl group, anthryl group, 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, and examples thereof include a pyridyl group, A pyrimidinyl group, a triazinyl group, a pyrazinyl group, a pyridazinyl group, a carbazolyl group, a dibenzothiophenyl group, and a dibenzofuranyl group.

More preferably, R ¹⁰¹ to R ¹⁰⁷ are each independently a hydrogen atom or an aryl group having 6 to 18 carbon atoms, particularly preferably a hydrogen atom or a phenyl group, more preferably a hydrogen atom. However, an embodiment wherein one or more of R ¹⁰¹ to R ¹⁰⁷ is a phenyl group is also preferable, and the embodiment in which 1 or 2 is a phenyl group is also more preferable.

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

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

As R ¹¹⁰ , at least one R ¹¹⁰ is a condensed ring aryl group having 10 to 30 ring atoms, a condensed ring 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 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 and the other R ¹¹⁰ is a hydrogen atom, Or a heteroaryl group having 5 to 25 ring atoms.

As R ¹¹⁰ , at least one R ¹¹⁰ is a condensed ring aryl group having 12 to 18 ring atoms, a condensed ring heteroaryl group having 9 to 13 ring atoms, or an aryl group having 6 to 18 carbon atoms Or a heteroaryl group having 6 to 13 ring atoms or a monocyclic heteroaryl group having 6 to 13 ring atoms having an aryl group having 6 to 18 carbon atoms as a substituent and the other R ¹¹⁰ is a hydrogen atom Do. The monocyclic heteroaryl group having 6 to 13 ring atoms and having a monocyclic aryl group having 6 to 18 carbon atoms as the substituent is preferably a heteroaromatic group having 6 to 10 ring atoms having a monocyclic aryl group having 6 to 10 carbon atoms as a substituent It is preferably an aryl group, and the preferred number of monocyclic aryl groups having 6 to 10 carbon atoms is 1 or 2.

An aryl group having 6 to 25 carbon atoms having a condensed ring and an aryl group having 8 to 30 ring atoms as a substituent, an aryl group having 6 to 25 carbon atoms as a substituent, or an aryl group having a ring position of a substituent of the atomic number 6-13 heteroaryl group, or a 6 to 20 carbon atoms can ring atoms having a single ring aryl group as a substituent of 5-20 heteroaryl group of a single ring of the R ¹¹⁰ is a, R a benzene ring to ^110. the substituted Meta position or para position with respect to the substituent forming the p-terphenylene skeleton of the R ^110, and the meta position or the para position among them may inhibit the ad-rejuvenation reaction between the R ¹¹⁰ and another substituent Or from the viewpoint of reducing device driving voltage. Further, when the luminescent color from the organic electroluminescent device is green (luminescent peak wavelength is 490 to 580 nm), it is more preferable that it is in the meta position from the viewpoint of luminescent efficiency.

L ¹⁰¹ represents a single bond or an arylene group. The arylene group may be a condensed ring (e.g., a naphthyl group, an anthryl group, or the like), but when the luminescent color from the organic electroluminescent device is green (luminescent peak wavelength is 490 to 580 nm) It is preferably an arylene group having no condensation ring and more preferably a structure in which a phenylene group which may have a substituent or a plurality of such groups is connected by a single bond. Examples of the arylene group represented by L ^{101 include} a phenylene group, a biphenylene group and a terphenylene group. The connection style of these is not particularly limited.

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

In the present invention, p-terphenylene and m-terphenylene each have the following structure (* indicates a bonding hand).

[Chemical Formula 13]

L &lt; ²⁰¹ &gt; is preferably unsubstituted, but may further have a substituent. When L &lt; ²⁰¹ &gt; has an additional substituent, examples of the substituent group include the above substituent group A, and a substituted or unsubstituted aryl group (phenyl group or biphenyl group) is preferable.

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

In general formula (2)

[Chemical 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 or different. L &lt; ²⁰¹ &gt; 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, A heteroaryl group having 5 to 25 ring atoms or a monocyclic heteroaryl group having 5 to 25 ring atoms and having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent and the other is a hydrogen atom, an aryl group or a heteroaryl group.

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

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

R ²¹⁰ to R ²¹² in the general formula (2) are preferably a hydrogen atom or an aryl group having 6 to 20 carbon atoms, and 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, which is a condensed ring, The preferable range of the heteroaryl group having 6 to 25 aryl groups or the heteroaryl group having 5 to 25 ring atoms or the monocyclic heteroaryl group having 5 to 25 ring atoms having a substituted monocyclic aryl group having 6 to 25 carbon atoms, A thiophenyl group, a dibenzofuranyl group, a triphenylenyl group, a carbazolyl group, an aryl group having 6 to 25 carbon atoms having these substituents or a heteroaryl group having 5 to 25 ring atoms, or a monocyclic aryl group having 6 to 13 carbon atoms Is a monocyclic heteroaryl group having 5 to 25 ring atoms and having 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, and a di More preferably a benzothiophenyl group or a triphenylenyl group, and still more preferably a triphenylenyl group. These condensed rings may further have the above skeleton as a basic skeleton and may further be condensed to each other.

The other 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, or the like), but when the luminescent color from the organic electroluminescent device is green (luminescence peak wavelength is 490 to 580 nm) From the viewpoint of efficiency, it is preferably an arylene group having no condensation ring, more preferably a phenylene group, a biphenylene group, or an m-terphenylene group, and a 1,3-phenylene group or a 3,5'- Is particularly preferable.

It is preferable that L &lt; ²⁰¹ &gt; in the general formula (2) is a single bond.

In general formula (3)

[Chemical Formula 15]

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 or different. L ³⁰¹ represents a single bond or an arylene group. One of A ³⁰¹ and A ³⁰² is a condensed ring aryl group having 10 to 30 ring atoms, a condensed ring heteroaryl group having 8 to 30 ring atoms, an aryl group having 6 to 25 carbon atoms having these as a substituent group, A heteroaryl group having 5 to 25 ring atoms or a monocyclic heteroaryl group having 5 to 20 ring atoms having a monocyclic aryl group having 6 to 25 carbon atoms as a substituent and the other is a hydrogen atom, an aryl group or a heteroaryl group.

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

The preferable range of R ³⁰¹ to R ³¹² in the general formula (3) is the same as the preferable range of R ¹⁰¹ to R ¹⁰⁹ in the general formula (1).

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

A preferable range of A ³⁰¹ and A ³⁰² in the general formula (3) is the same as the preferable range of A ²⁰¹ and A ²⁰² in the general formula (2).

The arylene group represented by L ³⁰¹ in the general formula (3) may be a condensed ring (for example, a naphthyl group, an anthryl group, etc.), but the luminescent color from the organic electroluminescent device is green (luminescent peak wavelength is 490 - 580 nm), it is preferably an arylene group having no condensation 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 a 3-phenylene group , 5'-biphenylene group is particularly preferable.

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

The organic electroluminescent device of the present invention is particularly preferably a compound represented by the general formula (1) represented by any of the following general formulas (4) to (7) and the following general formula (11) More preferably, the compound represented by the formula (1) is represented by any of the following formulas (4) to (7).

[Chemical 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 or different. n ₄₀₁ represents 0 or 1;

The preferable range of X ⁴⁰¹ and X ⁴⁰² in the general formula (4) is the same as the preferable range of X ¹⁰¹ in the general formula (1).

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

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

It is preferable that n ₄₀₁ in the general formula (4) is 0.

[Chemical 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 ⁵¹³ may be the same or different. n ₅₀₁ represents 0 or 1.

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

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

The preferable range of R ⁵⁰⁸ to R ⁵¹⁰ in the general formula (5) is the same as the preferable range of 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, more preferably a hydrogen atom.

It is preferable that n ₅₀₁ in the general formula (5) is 0.

[Chemical 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 or different.

The preferable range of X ⁶⁰¹ and X ⁶⁰² in the general formula (6) is the same as the preferable range of X ¹⁰¹ in the general formula (1).

A preferable range of R ⁶⁰¹ to R ⁶⁰⁷ and R ⁶¹⁴ to R ⁶²⁰ in the general formula (6) is the same as the preferable range of R ¹⁰¹ to R ¹⁰⁷ in the general formula (1).

The preferable range of R ⁶⁰⁸ to R ⁶¹³ in the general formula (6) is the same as the preferable range of R ¹⁰⁸ and R ¹⁰⁹ in the general formula (1).

[Chemical 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 or different.

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

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

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

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

&Quot; Compound of the present invention - particularly preferred embodiment of the compound represented by the above general formula (1) &quot;

Among the compounds represented by the above general formula (1), in the present invention, a compound represented by any one of the following general formulas (8) to (11) is particularly preferable. The compounds of the present invention represented by any one of the following general formulas (8) to (11) can be used for organic electronic devices such as electrophotography, organic transistors, organic photoelectric conversion devices And is particularly preferably used for an organic electroluminescent device.

[Chemical Formula 20]

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

In the general formulas (8) to (11), the preferable range of X ⁸⁰¹ to X ⁸⁰⁶ is the same as the preferable range of X ¹⁰¹ in the general formula (1).

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

In the general formula (11), A ¹¹ to A ¹³ each independently represent CH or a nitrogen atom, and at least one of them is a nitrogen atom. When A ¹¹ to A ¹³ contain one nitrogen atom, A ¹¹ or A ¹² is preferably a nitrogen atom. When two nitrogen atoms contained in A ¹¹ to A ¹³ are two, it is preferable that A ¹² and A ¹³ are nitrogen atoms.

The compound represented by the general formula (11) is a compound wherein A ¹¹ to A ¹³ have 1 nitrogen atom and A ¹¹ or A ¹² is a nitrogen atom, A ¹¹ to A ¹³ contain 2 nitrogen atoms, A ¹² and A ¹³ Is more preferably a nitrogen atom, or more preferably all of A ¹¹ to A ¹³ is a nitrogen atom. Among them, a compound in which the nitrogen atom contained in A ¹¹ to A ¹³ is one and the other A ¹² is a nitrogen atom, and the compound in which A ^{12 to} A ¹³ are nitrogen atoms and two nitrogen atoms contained in A ¹¹ to A ¹³ are particularly preferable Do.

Further, the compound represented by the above general formula (11) has a "nitrogen heteroaromatic ring" capable of deepening LUMO, and is preferable from the viewpoint of reducing device voltage. It is also preferable from the viewpoint of a small chromaticity difference at high temperature storage.

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 1,200 or less, more preferably 500 or more and 1,100 or less, still more preferably 550 or more and 1,000 or less. When the molecular weight is 450 or more, it is advantageous for forming a high quality amorphous thin film. When the molecular weight is 1,200 or less, solubility and sublimation property are improved, which is advantageous for improving the purity of the compound. In the organic electroluminescent device of the present invention, it is preferable that the molecular weight of the compound represented by the general formula (1) is 550 or more from the viewpoint of decreasing the chromaticity difference at high temperature storage. On the other hand, from the viewpoint of laminating a composition containing the compound represented by the general formula (1) by vapor deposition, it is preferable that the molecular weight of the compound represented by the general formula (1) is 1200 or less.

When the compound represented by the above general formula (1) is used as a host material of the light emitting layer of the organic electroluminescence device or as a charge transport material of the layer adjacent to the light emitting layer, the energy gap in the thin film state In the case where the light emitting material is a phosphorescent material like a device, if the lowest excitation triplet term (T ₁ ) energy in the thin film state) is large, the emission is prevented from being quenched, which is advantageous for improving the efficiency. On the other hand, from the viewpoint of the 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 ㎉ / mol) to 3.51 eV (81 ㎉ / ㏖) or less and preferably 2.39 eV (55 ㎉ / And more preferably 3.25 eV (75 ㎉ / mol) or less. The organic electroluminescent device of the present invention, it is preferable in view of T ₁ energy than the phosphorescent light-emitting material to be described later shown by the general formula (1) compound T ₁ energy is high that the light emitting efficiency. In particular, when the emission color from the organic electroluminescent device is green (the peak emission wavelength is 490 to 580 nm), the T ₁ energy is 2.39 eV (55 ㎉ / mol) to 2.82 eV (65 ㎉ / Or less.

The T ₁ energy can be obtained from the short wavelength end by measuring the phosphorescence emission spectrum of the thin film of the material. For example, the material is deposited on a cleaned quartz glass substrate to a film thickness of about 50 nm by a vacuum evaporation method, and the phosphorescence emission spectrum of the thin film is measured with an F-7000 Hitachi spectrophotometer (Hitachi High Technologies) . The T ₁ energy can be obtained by converting the rising wavelength of the obtained luminescence spectrum on the short wavelength side into energy units.

From the viewpoints of stably operating the organic electroluminescent device against high-temperature driving or heat generation during driving of the device, or from the viewpoint of reducing the chromaticity difference during storage at high temperature, in the organic electroluminescent device of the present invention, the compound represented by the general formula (1) Is preferably a compound having a glass transition temperature of 100 DEG C or higher. The glass transition temperature (Tg) of the compound represented by the general formula (1) is more preferably 100 ° C to 400 ° C, particularly preferably 120 ° C to 400 ° C, and more preferably 140 ° C to 400 ° C.

When the purity of the compound represented by the general formula (1) is low, the impurity acts as a trap for charge transport or accelerates the deterioration of the device. Therefore, the higher the purity of the compound represented by the general formula (1), the better. The purity can be measured, for example, by high performance liquid chromatography (HPLC). 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% More preferably 97.0% or more, particularly preferably 99.0% or more, and most preferably 99.9% or more. As a method for increasing the purity of the compound represented by the general formula (1), for example, a sublimation purification may be mentioned.

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

[Chemical Formula 21]

[Chemical Formula 22]

(23)

&Lt; EMI ID =

The compound exemplified as the compound represented by the above general formula (1) can be obtained, for example, by reacting the corresponding boronic acid or a boronic acid ester or a boronic acid ester salt with a corresponding halogen compound or a triflate compound in the presence of a metal catalyst Ni), and a coupling reaction using a ligand (such as triphenylphosphine or Buchwald ligand) (for example, Suzuki-Miyaura coupling). For example, it can be synthesized by the method described in Patent Document 1 described above.

In the present invention, the compound represented by the general formula (1) is not limited in its use and may be contained in any layer in the organic layer. The introduction layer of the compound represented by the general formula (1) is preferably contained in any one of the light emitting layer, the layer between the light emitting layer and the cathode (particularly, 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 one or more of the light emitting layer, the electron transporting layer, the electron injecting layer, the exciton blocking layer, the hole blocking layer, and the electron blocking layer, and is preferably contained in any of the light emitting layer, electron transporting layer, And more preferably those contained in the light-emitting layer or the electron-transporting layer. The compound represented by the above general formula (1) may be used in the above-mentioned plural layers. For example, it may be used for both the light emitting layer and the electron transporting 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%, more preferably 1 to 97 mass% , More preferably from 10 to 96 mass%. When the compound represented by the above 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%, more preferably 85 to 100 mass% Is more preferable.

(Phosphorescent material)

In the present invention, it is preferable that the light emitting layer has at least one phosphorescent material. In the present invention, in addition to the above phosphorescent material, a phosphorescent material different from the phosphorescent material contained in the luminescent layer or the phosphorescent material contained in the luminescent layer can be used as the luminescent material.

These fluorescent light emitting materials and phosphorescent light emitting materials are described in, for example, paragraphs [0100] to [0164] of JP-A No. 2008-270736 and paragraphs [0088] to [0090] of JP-A No. 2007-266458 And the matters described in these publications can be applied to the present invention.

Examples of the phosphorescent material which can be used in the present invention include those described in US 6303238 B1, US 6097147, WO 00/57676, WO 00/70655, WO 01/08230, WO 01/39234 A2, WO 01/41512 A1, WO 02/02714 A2, 15645 A1, WO 02/44189 A1, WO 05/19373 A2, JP-A 2001-247859, JP-A 2002-302671, JP-A 2002-117978, JP-A 2003-133074, JP-A 2002 -235076, JP-A-2003-123982, JP-A-2002-170684, EP1211257, JP-A 2002-226495, JP-A 2002-234894, JP-A 2001-247859, JP-A 2001 -298470, JP-A-2002-173674, JP-A 2002-203678, JP-A 2002-203679, JP-A 2004-357791, JP-A 2006-256999, JP-A 2007-19462 , Japanese Patent Application Laid-Open No. 2007-84635, Japanese Patent Application Laid-Open No. 2007-96259, etc. A phosphorescent compound, a phosphorescent compound, a phosphorescent compound, a phosphorescent compound, a phosphorescent compound, and a phosphorescent compound described above. Among them, more preferable luminescent materials include iridium (Ir) complex, platinum (Pt) complex, Cu complex, Re complex, W complex, Rh complex, Os complexes, Eu complexes, Tb complexes, Gd complexes, Dy complexes, and Ce complexes. Particularly preferred is an iridium (Ir) complex, a platinum (Pt) complex or an Re complex, and at least one of the metal-carbon bond, metal-nitrogen bond, metal-oxygen bond and metal- Iridium (Ir) complex, platinum (Pt) complex, or Re complex is preferable. An iridium (Ir) complex or a platinum (Pt) complex is particularly preferable, and an iridium (Ir) complex is most preferable from the viewpoints of luminous efficiency, drive durability and chromaticity.

These phosphorescent metal complex compounds are preferably contained in the light emitting layer together with the compound represented by the above general formula (1).

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 the general formula (E-1) will be described.

(25)

In the general formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom.

A ₁ represents a group of atoms forming a heterocycle of 5 or 6 atoms together with Z ¹ and a nitrogen atom.

B ₁ represents a group of atoms forming a 5 or 6-membered ring together with Z ² and a carbon atom.

(X-Y) represents a monoanionic two-coordinate ligand.

n _E1 represents an integer of 1 to 3;

n _E1 represents an integer of 1 to 3, preferably 2 or 3; When n _E1 is 2 or 3, a plurality of ligands may be the same or different.

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

A ₁ represents a group of atoms forming a heterocycle of 5 or 6 atoms together with Z ¹ and a nitrogen atom. Examples of the 5 or 6-membered heterocyclic ring containing A ₁ , Z ¹ and a nitrogen atom include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, , Triazole rings, oxadiazole rings, thiadiazole rings and the like.

From the viewpoints of the stability of the complex, the control of the emission wavelength, and the quantum yield of light emission, the 5 or 6-membered heterocyclic ring formed by A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring, More preferably a pyridine ring, an imidazole ring, or a pyrazine ring, more preferably a pyridine ring or an imidazole ring, and most preferably a pyridine ring.

The above-mentioned A ₁ , Z ¹ and the 5 or 6-membered heterocyclic ring formed by the nitrogen atom may have a substituent, and the above substituent group A can be applied as the substituent. The substituent is suitably selected for control of the emission wavelength or the electric potential. In the case of shortening the wavelength, the electron donating group, the fluorine atom and the aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, a fluorine atom, An aryl group and the like are selected. When the long wavelength is used, an electron-attracting group is preferable, and for example, a cyano group, a perfluoroalkyl group and the like are preferably selected. For the purpose of adjusting the intermolecular interaction, an alkyl group, a cycloalkyl group, an aryl group and the like are preferably selected.

The substituent on the carbon atom 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 or a fluorine atom.

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

The substituents may be connected to each other to form a condensed ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, A thiophene ring, a furan ring, and the like. These rings to be formed may have a substituent. Examples of the substituent include a substituent on the above-mentioned carbon atom and a substituent on the nitrogen atom.

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

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

The 5 or 6-membered ring formed by B ₁ , Z ² and a carbon atom may have a substituent, the substituent group A on the carbon atom and the substituent group B on the nitrogen atom may be the following substituent group B .

The substituent on the carbon atom 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 or a fluorine atom.

"Substituent group B"

(Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, tert-butyl, n-octyl, , an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as methyl, ethyl, n-propyl, , An alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 carbon atoms, such as vinyl, allyl, 2-butenyl and 3-pentenyl) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms), an aryl group (preferably having 1 to 10 carbon atoms, such as propargyl and 3-pentynyl) For example, phenyl, p-methylphenyl, naphthyl, anthryl, and the like. ), A cyano group, a heterocyclic group (including a heteroaryl group, preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and the heteroatom includes, for example, a nitrogen atom, And examples thereof include an atom, a silicon atom, a selenium atom, and a tellurium atom. Specific examples thereof include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, Wherein the substituents are selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, heteroaryl, heteroaryl, , Benzothiazolyl, carbazolyl group, azepinyl group, and silylyl group). These substituents may be further substituted, and examples of the additional substituent include groups selected from Substituent Group B described above.

The substituent on the carbon is appropriately selected for control of the emission wavelength or the electric potential. In the case of long wavelengths, the electron donating group and the aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, Is selected. In the case of shortening the wavelength, an electron-attracting group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group and the like are selected. For the purpose of adjusting the intermolecular interaction, an alkyl group, a cycloalkyl group, an aryl group and the like are preferably selected.

The substituent on the nitrogen is preferably an alkyl group, an aryl group or a heteroaryl group, and from the viewpoint of stability of the complex, an alkyl group or an aryl group is preferable. The substituents may be connected to each other to form a condensed ring. Examples of the ring formed include a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, A thiophene ring, a furan ring, and the like. These rings to be formed may have a substituent. Examples of the substituent include a substituent on the above-mentioned carbon atom and a substituent on the nitrogen atom.

The substituent of the 5 or 6-membered heterocyclic ring formed by A ₁ , Z ¹ and the nitrogen atom and the substituent of the 5 or 6-membered ring formed by B ₁ , Z ² and the carbon atom are connected to form a condensed ring .

(X-Y) represents a monoanionic ligand of two residues. An example of a two-monoanionic ligand is described in Lamansky's International Publication No. 02/15645 on pages 89-90.

Is preferably a two-monoanionic ligand represented by the following general formula (L-1) as a two-monoanionic ligand represented by the general formula (X-Y).

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In the 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. As the substituent in the case of having a substituent, the following substituent Z 'can be exemplified, and preferable substituent Z' is a phenyl group, a heteroaryl group, a fluorine atom, a silyl group, an amino group, a cyano group, Fluorine atom and 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.

&Quot; Substituent Z &quot;

An alkyl group (preferably having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms such as methyl, ethyl, isopropyl, n-propyl, n-butyl, neopentyl, n-pentyl, n-hexyl, cyclopropyl, cyclopentyl and cyclohexyl), an alkenyl group (preferably having 2 to 8 carbon atoms, more preferably 2 to 5 carbon atoms , An aryl group (having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, such as a phenyl group, a naphthyl group, an anthracenyl group, a tetracenyl group, a pyrenyl group, a phenyl group, (Preferably having from 4 to 30 carbon atoms, more preferably from 4 to 20 carbon atoms, such as pyridine, pyrazine, pyrimidine, pyridazine, pyridazinyl, pyridazinyl, , Triazine, thiophene, furan, oxazole, thiazole, imidazole , An alkoxy group (preferably having 1 to 8 carbon atoms, more preferably 1 to 5 carbon atoms, such as a methoxy group, an ethoxy group, an isopropoxy group, an isopropoxy group, , a halogen atom (preferably a fluorine atom), a silyl group (preferably having 4 to 30 carbon atoms, more preferably 4 to 30 carbon atoms, (Preferably having 2 to 60 carbon atoms, more preferably 2 to 40 carbon atoms, such as dimethylamino group, diethylamino group, diethylamino group, diethylamino group, diethylamino group, Diphenylamino group, and the like), cyano group, or a group formed by combining these groups, and a plurality of substituents Z 'may be bonded to each other to form an aryl ring. 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 substituted or may have a substituent. As the substituent in the case of having a substituent, the above-mentioned substituent Z 'can be mentioned, 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 substituted or may have a substituent. As the substituent in the case of having a substituent, the above-mentioned substituent Z 'can be mentioned, 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 heteroaryl group having 4 to 12 carbon atoms, and more preferably a heteroaryl group having 4 to 10 carbon atoms.

R ^L1 and R ^L2 are preferably 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 in total, more preferably an alkyl group having 1 to 5 total carbon atoms, such as methyl group, ethyl group, n-propyl group an iso-propyl group, an iso-butyl group, a t-butyl group, an n-butyl group and a cyclohexyl group, and a methyl group, an ethyl group, an iso-butyl group or a t- desirable.

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

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

Next, the general formula (E-2) will be described.

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In the general formula (E-2), each of A ^E1 to A ^E8 independently represents a nitrogen atom or CR ^E.

R ^E represents a hydrogen atom or a substituent.

(X-Y) represents a monoanionic two-coordinate ligand.

n _E2 represents an integer of 1 to 3;

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

As A ^E1 to A ^E4 , preferably CR ^E and A ^E1 to A ^E4 are CR ^E , R ^E of A ^E3 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group , a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom, or a fluorine atom, a ^E1, a ^E2 and R ^E in A ^E4 is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, Or a fluorine atom, and particularly preferably a hydrogen atom.

As A ^E5 to A ^E8 , preferably CR ^E , and when A ^E5 to A ^E8 are CR ^E , R ^E is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkyl More preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a dialkylamino group, a cyano group, or a fluorine atom, and more preferably a fluorine atom, Is a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. When possible, substituents may be connected to each other to form a condensed ring structure. In the case of 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} formula (E-1), and their preferred ranges are also the same.

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

(28)

In formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a perfluoroalkyl group, a vinyl group, _{trifluoromethyl, -CO 2 R, -C (O} ) R, -NR 2, -NO 2, -OR, halogen atom, an aryl group or a heteroaryl group, a substituent in more Z . Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

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

Any two of R ^T1 to R ^T7 and R 'may combine with each other to form a condensed 4- to 7-membered ring, the condensed 4- to 7-membered ring is a cycloalkyl, aryl or heteroaryl, The 7-membered ring may further have a substituent Z. Among them, R ^T1 and R ^T7 , or R ^T5 and R ^T6 are preferably coordinated to form a benzene ring, and it is particularly preferable that a benzene ring is formed by being condensed with R ^T5 and R ^T6 .

Z is independently selected from the group consisting of halogen atoms, -R ", -OR", -N (R ") ₂ , -SR", -C (O) (R ") ₂ , -CN, -NO ₂ , -SO ₂ , -SOR", -SO ₂ R ", or -SO ₃ R", and R "each independently represents a hydrogen atom, an alkyl group, , An alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

(XY) represents a monoanionic two-coordinate ligand. n _E3 represents an integer of 1 to 3;

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

The cycloalkyl group may have a substituent, may be saturated or unsaturated, and the group which may be substituted includes the substituent Z described above. 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, and examples thereof include a cyclopentyl group, A t-butyl group, and a cyclohexyl group.

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, and particularly preferably 2 to 10 carbon atoms. Examples of the alkenyl group include vinyl, allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.

The alkynyl group represented by R ^T1 to R ^T7 and R 'preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. Examples of the alkynyl group include ethynyl, 1-propynyl, 3-pentynyl, and the like.

The perfluoroalkyl group represented by R ^T1 to R ^T7 and R 'includes those in which all the hydrogen atoms of the above-mentioned alkyl group are substituted with fluorine atoms.

The aryl group represented by R ^T1 to R ^T7 and R 'is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms such as 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 heteroaryl group having 5 to 8 carbon atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 or 6 atoms, A pyridyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a cinnolinyl group, a phthalazinyl group, a quinoxalinyl group, A thiazolyl group, a thiazolyl group, a benzothiazole group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, an isoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, an imidazolyl group, an imidazolyl group, A thiazolyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, Benzothienyl group, and the like based degrees turned 7 flutes. Preferable examples are a pyridyl group, a pyrimidinyl group, an imidazolyl group and a thienyl group, more preferably a pyridyl group and a pyrimidinyl group.

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

Any two of R ^T1 to R ^T7 and R 'may combine with each other to form a condensed 4- to 7-membered ring, the condensed 4- to 7-membered ring is a cycloalkyl, aryl or heteroaryl, The atomic ring may further have a substituent Z. The definition and preferable range of the cycloalkyl, aryl and heteroaryl to be formed are the same as those of the cycloalkyl group, aryl group and heteroaryl group defined in R ^T1 to R ^T7 and R '.

Particularly preferred are those wherein A represents CR ', 0 to 2 out of R ^T1 to R ^T7 and R' are an alkyl group or a phenyl group, and all others are hydrogen atoms, and R ^T1 to R ^T7 and Among R ', it is particularly preferable that 0 to 2 are alkyl groups, and all others are hydrogen atoms.

n _E3 is preferably 2 or 3. When n _E3 is 2 or 3, a plurality of ligands may be the same or different. The ligand in the complex is preferably one or two kinds.

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

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

[Chemical Formula 29]

R ^T1 to R ^T4 , A, (XY) and n _E4 in the general formula (E-4) are represented by R ^T1 to R ^T4 , A, (XY) and n _{E3 in the} general formula (E- And the preferred range is also the same. R ₁ 'to R ₅ ' each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, a trifluorovinyl group, -CO ₂ R, -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. Each R 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 a cycloalkyl, aryl or heteroaryl, The ring may further have a substituent Z.

Z is independently selected from the group consisting of halogen atoms, -R ", -OR", -N (R ") ₂ , -SR", -C (O) (R ") ₂ , -CN, -NO ₂ , -SO ₂ , -SOR", -SO ₂ R ", or -SO ₃ R", and R "each independently represents a hydrogen atom, an alkyl group, , An alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.

The preferable range for R ₁ 'to R ₅ ' is the same as R ^T1 to R ^T7 and R 'in formula (E-3). It is particularly preferable that A represents CR ', 0 to 2 out of R ^T1 to R ^T4 , R' and R ₁ 'to R ₅ ' represent an alkyl group or a phenyl group, and all others are hydrogen atoms , R ^T1 to R ^T4 , R ', and R ₁ ' to R ₅ 'are each an alkyl group and the rest are all hydrogen atoms.

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

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(31)

(32)

The compound exemplified as the compound represented by the above general formula (E-1) can be synthesized by various methods described in JP-A-2009-99783, US Pat. No. 7279232, and the like. After the synthesis, it is preferable to carry out purification by column chromatography, recrystallization and the like, and then purify by sublimation purification. By the sublimation purification, it is possible not only to separate organic impurities, but also to effectively remove inorganic salts and residual solvents.

The phosphorescent material is preferably contained in the light emitting layer, but its application is not limited, and may be further contained in any layer in the organic layer.

The phosphorescent material in the light-emitting layer is preferably contained in the light-emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the mass of the total compound forming the light-emitting layer, and 1% by mass to 50% by mass from the viewpoint of durability and external quantum efficiency By mass, more preferably 2% by mass to 40% by mass.

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

(3) Other host materials

Examples of the host material that can be used for the other light emitting layer other than the compound represented by the general formula (1) include a compound having the following structure as a partial structure.

And examples thereof include aromatic hydrocarbon, pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, (N-vinylcarbazole), poly (N-vinylcarbazole), and the like can be used as the aromatic amine compound, arylamine, amino substituted chalcone, styrylanthracene, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound, , An aniline-based copolymer, a conductive polymer oligomer such as a thiophene oligomer and a polythiophene, an organic silane, a carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, A heterocyclic tetracarboxylic acid such as lanthanum, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compound and naphthaleneperylene A metal complex of an anhydride, a phthalocyanine, an 8-quinolinol derivative, various metal complexes represented by a metal complex having metal phthalocyanine, benzoxazole or benzothiazole as a ligand, and derivatives thereof (may have a substituent or a ring) .

(Other layers)

The organic electroluminescent device of the present invention may have other layers than the above-mentioned light emitting layer.

Examples of the organic layer other than the light emitting layer that the organic layer may have include a hole injecting layer, a hole transporting layer, a blocking layer (hole blocking layer, exciton blocking layer, etc.), and an electron transporting layer. The above-mentioned specific layer configuration is exemplified below, but the present invention is not limited to these configurations.

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

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

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

Anode / hole injecting layer / hole transporting layer / light emitting layer / block layer / electron transporting layer / cathode,

Anode / hole injecting layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode,

Anode / hole injecting layer / hole transporting layer / light emitting layer / block layer / electron transporting layer / electron injecting layer / cathode,

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

The organic electroluminescent device of the present invention preferably comprises (A) at least one organic layer preferably disposed between the anode and the light emitting layer. Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injecting layer, a hole transporting layer, and an electron blocking layer from the anode side.

The organic electroluminescent device of the present invention preferably comprises (B) at least one organic layer preferably disposed between the cathode and the light emitting layer. Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injecting layer, an electron transporting layer, and a hole blocking layer from the cathode side.

More specifically, an example of a preferred embodiment of the organic electroluminescent device of the present invention is the embodiment described in Fig. 1, in which the hole injection layer 4, the hole transport layer 5, the light emitting layer 6 ), A hole blocking layer (7) and an electron transport layer (8) are laminated in this order.

Hereinafter, other layers other than the light emitting layer which the organic electroluminescence device of the present invention can have will be described.

(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) a hole injecting layer, a hole transporting 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.

For the hole injection layer and the hole transport layer, the matters described in paragraphs [0165] to [0167] of Japanese Patent Laid-Open No. 2008-270736 can be applied to the present invention.

The hole injection layer preferably contains an electron-accepting dopant. By including the electron-accepting dopant in the hole injection layer, the hole injecting property is improved, the driving voltage is lowered, and the efficiency is improved. The electron-accepting dopant may be any organic material or inorganic material as long as it is capable of generating radical cations by drawing electrons from the doped material. For example, tetracyanoquinodimethane (TCNQ), tetrafluoro Tetracyanoquinodimethane (F ₄ -TCNQ), molybdenum oxide, and the like.

The electron-accepting dopant in the hole-injecting 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, more preferably 0.2% By mass to 30% by mass.

(A-2) Electronic 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 and the anode side.

The T ₁ energy in the film state of the organic compound constituting the electronic block layer is preferably higher than the T ₁ energy of the light emitting material in order to prevent energy migration of the excitons generated in the light emitting layer and not to lower the light emitting efficiency.

As examples of the organic compound constituting the electron blocking layer, any of the above-described hole transporting materials can be applied.

The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.

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

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

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

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

The compound represented by the above 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 the use thereof is not limited and may be further contained in any layer in the organic layer. The introduction layer of the compound represented by the general formula (M-1) may be contained in any one or more of the light emitting layer, the hole injecting layer, the hole transporting layer, the electron transporting layer, the electron injecting layer and the charge blocking layer.

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

(33)

Wherein Ar ₁ and Ar ₂ are each independently selected from the group consisting of alkyl, aryl, heteroaryl, arylamino, alkylamino, morpholino, thiomorpholino, N, O, and S 5 or 6-membered heterocycloalkyl or cycloalkyl containing at least one hetero atom, and may further have a substituent Z. Ar ₁ and Ar ₂ may combine with each other to form a condensed 5- to 9-membered ring by a single bond, alkylene, or alkenylene (with or without condensed rings).

Ar ₃ represents P, alkyl, aryl, heteroaryl or arylamino, and may further have a substituent Z.

Z is independently selected from the group consisting of halogen atoms, -R ", -OR", -N (R ") ₂ , -SR", -C (O) (R ") ₂ , -CN, -NO ₂ , -SO ₂ , -SOR", -SO ₂ R ", or -SO ₃ R", and R "each independently represents a hydrogen atom, an alkyl 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.

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

(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 formula (M-2), R ^M1 is 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 may have substituent Z described above. R ^M1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. The preferable substituent when the aryl group of R ^{M1 has} a substituent is an alkyl group, a halogen atom, a cyano group, an aryl group or an alkoxy group, more preferably an alkyl group, a halogen atom, a cyano group or an aryl group, An anion group, or an aryl group is more preferable. The aryl group of R &lt; ^M1 &^gt; is preferably a phenyl group which may have a substituent Z, and more preferably a phenyl group which may have an alkyl group or cyano group.

Each of R ^M2 to R ^M23 independently represents 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) (Preferably having from 1 to 8 carbon atoms), an aryloxy group (preferably having from 6 to 30 carbon atoms), an amino group (preferably from 0 to 24 carbon atoms), a silyl group (preferably from 0 to 18 carbon atoms) Or a fluorine atom, and they may have the substituent Z described above.

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

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

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

R ^M10 , R ^M13 , R ^M18 and R ^M21 are preferably an alkyl group, an aryl group, a heteroaryl group or an amino group, a nitro group, a fluorine atom or a cyano group which may have a hydrogen atom or a substituent Z, 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 an alkyl group which may have a hydrogen atom or a substituent Z, When the alkyl group has a substituent, the substituent is preferably a fluorine atom, and the alkyl group which may have a substituent Z preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms.

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

(35)

Wherein the general formula (M-3), R ^S1 ~ ^S5 R is a vinyl group, -CO ₂ R a each independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, -CN, a perfluoroalkyl group, trifluoromethyl, - 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. Each R 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 are present, they may be bonded to each other to form a ring or may further have a substituent Z.

a represents an integer of 0 to 4, and when a plurality of R ^{S1 s} exist, they may be the same or different and may be bonded to each other to form a ring. b to e each independently represent an integer of 0 to 5, and when a plurality of R ^S2 to R ^{5 s} are present, they may be the same or different and arbitrary two may combine to form a ring.

q is an integer of 1 to 5, and when q is 2 or more, plural 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, may be saturated or unsaturated, and the group which may be substituted includes the substituent Z described above. The alkyl group represented by R ^S1 to R ^S5 is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl group, ethyl group, i-propyl group , A cyclohexyl group, and a t-butyl group.

The cycloalkyl group may have a substituent, may be saturated or unsaturated, and the group which may be substituted includes the substituent Z described above. The cycloalkyl group represented by R ^S1 to R ^S5 is preferably a cycloalkyl group having 4 to 7 ring atoms and more preferably a cycloalkyl group having 5 to 6 total carbon atoms and includes, for example, a cyclopentyl group, a cyclohexyl group And practical training.

The alkenyl group represented by R ^S1 to R ^S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms, such as 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, and particularly preferably 2 to 10 carbon atoms, such as ethynyl, propargyl, 1 -Propinyl, 3-pentynyl and the like.

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

The aryl group represented by R ^S1 to R ^S5 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms such as a phenyl group, a tolyl group, a biphenyl group, a terphenyl group, and the like.

The heteroaryl group represented by R ^S1 to R ^S5 is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 or 6 atoms, and examples thereof include a pyridyl group, A pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a cinnolinyl group, a phthalazinyl group, a quinoxalinyl group, a pyrrolyl group, A benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, An isothiazolyl group, a benzisothiazolyl group, a thiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group , A sulfonyl group, a carbazolyl group, a dibenzofuryl group, a dibenzo On it may be mentioned groups, such as group turn-pyrido [deg. Preferable examples are a pyridyl group, a pyrimidinyl group, an imidazolyl group and a thienyl group, more preferably a pyridyl group and a pyrimidinyl group.

R ^S1 to R ^S5 are preferably hydrogen, alkyl, cyano, trifluoromethyl, perfluoroalkyl, dialkylamino, fluoro, aryl or heteroaryl groups, more preferably hydrogen, An alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group, more preferably a hydrogen atom, an alkyl group or an aryl group. The substituent Z is preferably an alkyl group, an alkoxy group, a fluoro group, a cyano group or a dialkylamino group, more preferably a hydrogen atom or an alkyl group.

Any two of R ^S1 to R ^S5 may combine with each other to form a condensed 4- to 7-membered ring, the condensed 4- to 7-membered ring is a cycloalkyl, aryl or heteroaryl, and the condensed 4- to 7-membered ring is And may further have a substituent Z. The definition and preferable range of the cycloalkyl, aryl and heteroaryl to be formed are the same as those of the cycloalkyl group, aryl group and heteroaryl group defined in R ^S1 to R ^S5 .

When the compound represented by the general formula (M-1) is used in the hole transporting layer, the compound represented by the general formula (M-1) is preferably contained in an amount of 50 to 100 mass%, more preferably 80 to 100 mass% , More preferably from 95 to 100 mass%.

When a compound represented by the above general formula (M-1) is used for a plurality of organic layers, it is preferable that the compound is contained in the above range in each layer.

The compound represented by the above general formula (M-1) may contain only one kind in any organic layer, or may contain a plurality of compounds represented by the general formula (M-1) in an arbitrary ratio.

The thickness of the hole transporting layer containing the compound represented by the general formula (M-1) is preferably from 1 nm to 500 nm, more preferably from 3 nm to 200 nm, even more preferably from 5 nm to 100 nm Do. It is preferable that the hole transporting layer is formed in contact with the light emitting layer.

The energy of the lowest excitation triplet (T ₁ ) in the film state of the compound represented by the general formula (M-1) is preferably 1.77 eV (40 ㎉ / mol) to 3.51 eV (81 ㎉ / ㏖) (55 ㎉ / mol) to 3.25 eV (75 ㎉ / ㏖) or less. The organic electroluminescent device of the present invention, it is preferable in view of the above-mentioned general formula (M-1) Compound T ₁ energy efficiency is high is indicated by emission of energy than the T ₁ of the aforementioned phosphorescent materials. In particular, when the emission color from the organic electroluminescent device is green (the peak emission wavelength is 490 to 580 nm), the T ₁ energy is 2.39 eV (55 ㎉ / mol) to 2.82 eV (65 ㎉ / ) Or less.

The hydrogen atom constituting the above general formula (M-1) also includes isotopes of hydrogen (deuterium atoms, etc.). In this case, all of the hydrogen atoms in the compound may be substituted with hydrogen isotopes, or a mixture in which some of them are hydrogen isotopes.

The compound represented by the above general formula (M-1) can be synthesized by combining various known synthetic methods. Most commonly, as to the carbazole compound, the synthesis by dehydrogenation aromatization (LF Tieze, Th. Eicher, Takano, Ogasawara Station, Precise Organic Synthesis) after the azeotropic reaction of the condensate of arylhydrazine and cyclohexane derivative Synthesis, 339 pages (published by Nankodo)). The coupling reaction using the obtained carbazole compound and a halogenated aryl compound using a palladium catalyst is described in Tetrahedron Letters, vol. 39, p. 617 (1998), Tetrahedron Letters, vol. 39, p. 2367 (1998) Tetrahedron Letters, Vol. 40, p. 6393 (1999), and the like. The reaction temperature and the reaction time are not particularly limited, and the conditions described in the above documents can be applied.

The compound represented by the general formula (M-1) is preferably formed into a thin layer by a vacuum deposition process, but a wet process such as solution coating can also be preferably used. The molecular weight of the compound is preferably 2,000 or less, more preferably 1,200 or less, and particularly preferably 800 or less, from the viewpoints of suitability for deposition and solubility. Further, from the viewpoint of the deposition suitability, 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 the organic layer, and therefore 250 or more is preferable, and 300 or more is particularly preferable.

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

(36)

(37)

(38)

[Chemical Formula 39]

(40)

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

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

(B-1) an electron injection layer, an 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 electron transporting material used in these layers may be a low molecular compound or a high molecular compound.

As the electron transporting material, a compound represented by the above general formula (1) can be used. Examples of other electron transporting materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, Derivatives such as fluorene derivatives, fluorene derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene methane derivatives, distyrylpyrazine derivatives, naphthalene and perylene A metal complex of 8-quinolinol derivative, various metal complexes represented by metal phthalocyanine, a metal complex having benzooxazole or benzothiazole as a ligand, an organosilane derivative represented by siloxane And the like.

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

The thickness of the electron transporting layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm. The thickness of the electron injection layer is preferably 0.1 nm to 200 nm, more preferably 0.2 nm to 100 nm, and even more preferably 0.5 nm to 50 nm.

The electron injection layer and the electron transporting layer may have a single layer structure composed of one or more of the above-described materials, or a multi-layer structure composed of plural layers of the same composition or different composition.

The electron injecting layer preferably contains an electron donating dopant. Including an electron donating dopant in the electron injecting layer has the effect of improving the electron injecting property, lowering the driving voltage, and improving the efficiency. The electron donor dopant may be any of organic materials and inorganic materials as long as electrons can be given to the doped material to generate radical anions. Examples of the electron donating dopant include tetrathiafulvalene (TTF), tetrathianaphthacene (TTT) and bis- [1,3-diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

The electron donor dopant in the electron injecting 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 with respect to the total mass of the compound forming the electron injecting layer, more preferably 0.5% By mass to 30% by mass.

(B-2) a hole blocking layer

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

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

As the organic compound constituting the hole blocking layer, a compound represented by the above 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) ) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)), and the like. In the present invention, the hole blocking layer is not limited to the function of actually blocking holes, and may have a function of preventing the excitons of the light emitting layer from diffusing into the electron transporting layer, or blocking energy transfer extinction. The compound of the present invention is also preferably used as a hole blocking layer.

The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm.

The hole blocking layer may be a single layer structure composed of one or more of the above-described materials, or a multilayer structure composed of plural layers of the same composition or different composition.

(B-3) A material particularly preferably used for an organic layer which is 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 which is preferably disposed between the cathode (B) and the light emitting layer, wherein the compound represented by the general formula (1), the aromatic hydrocarbon compound , The following general formula (Tp-1)) and the compound represented by the following general formula (O-1).

Hereinafter, the aromatic hydrocarbon compound and the compound represented by the formula (O-1) will be described.

[Aromatic hydrocarbon compound]

The aromatic hydrocarbon compound is more preferably contained in the organic layer adjacent to the light emitting layer between the light emitting layer and the cathode, but the use thereof is not limited, and may be further contained in any layer in the organic layer. The introduction layer of the aromatic hydrocarbon compound may be contained in any one or plural of the light emitting layer, the hole injecting layer, the hole transporting layer, the electron transporting layer, the electron injecting layer, the exciton blocking layer and the charge blocking layer.

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 and more preferably an electron transporting layer.

The aromatic hydrocarbon compound is preferably composed only of carbon atoms and hydrogen atoms from the viewpoint of ease of synthesis.

When the aromatic hydrocarbon compound is contained in a layer other than the light emitting layer, the content is preferably 70 to 100 mass%, and more preferably 85 to 100 mass%. When the aromatic hydrocarbon compound is contained in the light emitting layer, it is preferably contained in an amount of 0.1 to 99 mass%, more preferably 1 to 95 mass%, and more preferably 10 to 95 mass%, relative to the total mass of the light emitting layer Do.

The aromatic hydrocarbon compound is preferably a hydrocarbon compound having only a carbon atom and a hydrogen atom and having a molecular weight in the range of 400 to 1200 and a condensed polycyclic skeleton having 13 to 22 carbon atoms in total. Bullets with the condensed polycyclic skeleton of the small number of 13-22 is, fluorene, anthracene, phenanthrene, tetracene, chrysene, pentacene, pyrene, perylene, triphenylene, and preferably in any of the alkylene to, the point of view of T ₁ Triphenylene and phenanthrene are more preferable, and triphenylene is more preferable from the viewpoints of stability of the compound and charge injecting and transporting property, and a compound represented by the following general formula (Tp-1) is particularly preferable .

The molecular weight of the hydrocarbon compound represented by the general formula (Tp-1) is preferably in the range of 400 to 1,200, more preferably 400 to 1,000, and still more preferably 400 to 800. When the molecular weight is 400 or more, a high quality amorphous thin film can be formed. When the molecular weight is 1,200 or less, it is preferable from the viewpoint of solubility in a solvent, sublimation and deposition suitability.

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

(41)

In the general formula (Tp-1), R ¹² to R ²³ each independently represent a phenyl group, a fluorenyl group, , A naphthyl group, or a triphenylenyl group. Provided that R ¹² to R ²³ do not all become hydrogen atoms.

Examples of the alkyl group represented by R ¹² to R ²³ include a substituent or an unsubstituted group such as a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-octyl group, An ethyl group, an isopropyl group, a tert-butyl group and a cyclohexyl group, more preferably a methyl group, an ethyl group, or a tert-butyl group, -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 triphenylrenyl group More preferably a phenyl group, a fluorenyl group, a naphthyl group, or a triphenylenyl group which may be substituted with a triphenylenyl group or a triphenylenyl group.

A benzene ring which may be substituted with a phenyl group, a fluorenyl group, a naphthyl group or a triphenylrenyl group (which may also be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group or a triphenylenyl group) .

The total number of aryl rings in the general formula (Tp-1) is preferably 2 to 8, more preferably 3 to 5. By setting the concentration within this range, a high-quality amorphous thin film can be formed, and solubility in solvents, sublimation, and deposition suitability are improved.

R ¹² to R ²³ each independently preferably have a total number of carbon atoms of 20 to 50, and more preferably 20 to 36 carbon atoms. By setting the concentration within this range, a high-quality amorphous thin film can be formed, and solubility in solvents, sublimation, and deposition suitability are improved.

The hydrocarbon compound represented by the formula (Tp-1) is preferably a hydrocarbon compound represented by the following formula (Tp-2).

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In the general formula (Tp-2), a plurality of Ar ^{1 s} are the same, and represent a phenyl group, a fluorenyl group, a naphthyl group or a triphenylenyl group which may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group or a triphenylenyl group Lt; / RTI &gt;

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

The hydrocarbon compound represented by the general formula (Tp-1) is also preferably a hydrocarbon compound represented by the following general formula (Tp-3).

(43)

In the general formula (Tp-3), L represents a phenyl group, a fluorenyl group, a naphthyl group, a triphenylenyl group or a combination thereof, which may be substituted with an alkyl group, a phenyl group, a fluorenyl group, a naphthyl group or a triphenylenyl group Lt; / RTI &gt; n represents an integer of 1 to 6;

The alkyl group, phenyl group, fluorenyl group, naphthyl group or triphenylenyl group forming an n-valent linking group represented by L has the same meaning as in R ¹² to R ²³ .

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

Specific preferred examples of L are given below, but the present invention is not limited thereto. Also, * in the specific examples is bonded to the triphenylene ring.

(44)

n is preferably 1 to 5, more preferably 1 to 4.

When the hydrocarbon compound represented by the general formula (Tp-1) is used as a host material of the light emitting layer of the organic electroluminescence device or a layer adjacent to the light emitting layer, the energy gap in the thin film state In the case of a phosphorescent material, the energy of the lowest excitation triplet (T ₁ ) in a thin film state is large), the emission is prevented from being quenched, which is advantageous for improving the efficiency. On the other hand, from the viewpoint of the 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 ㎉ / mol) to 3.51 eV (81 ㎉ / ㏖) or less and preferably 2.39 eV (55 ㎉ / ) Or more and 3.25 eV (75 ㎉ / mol) or less. The organic electroluminescent device of the present invention, it is preferable in view of the above-mentioned general formula (Tp-1) Compound T ₁ energy efficiency is high is indicated by emission of energy than the T ₁ of the aforementioned phosphorescent materials. In particular, when the emission color from the organic electroluminescent device is green (the peak emission wavelength is 490 to 580 nm), the T ₁ energy is 2.39 eV (55 ㎉ / mol) or more and 2.82 eV (65 ㎉ / ) Or less.

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

The glass transition temperature (Tg) of the hydrocarbon compound according to the present invention is preferably 80 deg. C or more and 400 deg. C or less, and more preferably 100 deg. C or more and 400 deg. C or more, from the viewpoint of stably operating the organic electroluminescent element at high- And more preferably 120 deg. C or higher and 400 deg. C or lower.

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

[Chemical Formula 45]

(46)

The compounds exemplified as the hydrocarbon compounds represented by the general formula (Tp-1) are described in WO 05/013388, WO 06/130598, WO 09/021107, US2009 / 0009065, Can be synthesized by the method described in the pamphlet of Publication No. 09/008311 and the pamphlet of International Patent Publication No. 04/018587.

After the synthesis, it is preferable to carry out purification by column chromatography, recrystallization and the like, and then purify by sublimation purification. By the sublimation purification, it is possible not only to separate organic impurities, but also to effectively remove inorganic salts and residual solvents.

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

As a material particularly preferably used for the material of the organic layer preferably disposed between the cathode (B) and the light emitting layer, it is preferable to use a compound represented by the following general formula (O-1) . Hereinafter, general formula (O-1) will be described.

(47)

In the 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 a 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's 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 an integer of 2 to 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) . R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. The preferred substituent when the aryl group of R ^O1 has a substituent is an alkyl group, an aryl group or a cyano group, more preferably an alkyl group or an aryl group, and more preferably an aryl group. When the aryl group of R ^O1 has plural substituents, the plural 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 a phenyl group which may be substituted with an alkyl group or an aryl group, still more preferably an unsubstituted phenyl group or a 2-phenylphenyl group.

A ^O1 to A ^O4 each independently represent a CR ^A or a nitrogen atom. Of A ^O1 to A ^O4 , 0 to 2 are preferably nitrogen atoms, and 0 or 1 is more preferably a nitrogen atom. It is preferable that all of A ^O1 to A ^O4 are CR ^A or that A ^O1 is a nitrogen atom and A ^O2 to A ^O4 are CR ^A , and that A ^O1 is a nitrogen atom and A ^O2 to A ^O4 are CR ^A It is more preferable that A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are CR ^A , and R ^A is a hydrogen atom.

R ^A represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably 6 to 30 carbon atoms), or a heteroaryl group (preferably 4 to 12 carbon atoms) '. The plural R ^A may be the same or different. R ^A is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). As L ⁰¹ , it 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, more preferably a biphenylene group, Or a benzenetriyl group. L ^O1 may have the above-mentioned substituent Z ', and as the substituent having a substituent, an alkyl group, an aryl group, or a cyano group is preferable. Specific examples of L ^O1 include the following.

(48)

n ^O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n ^O1 is most preferably 3 from the viewpoint of the efficiency of the organic electroluminescent device, and is most preferably 2 from the viewpoint of the durability of the organic electroluminescent device.

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

(49)

In the 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 a 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's 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) , And they may have substituent group A described above. R ⁰² to R ⁰⁴ is 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 above general formula (O-1) has a glass transition temperature (Tg) of 100 ° C to 400 ° C from the standpoint of stability at high temperature storage and stable operation at the time of driving at high temperature, More preferably from 120 ° C to 400 ° C, and even more preferably from 140 ° C to 400 ° C.

Specific examples of the compound represented by the formula (O-1) are shown below, but the compounds used in the present invention are not limited thereto.

(50)

(51)

The compound represented by the above general formula (O-1) can be synthesized by the method described in JP-A-2001-335776. After the synthesis, it is preferable to perform purification by column chromatography, recrystallization, reprecipitation or the like, and then purification by sublimation purification. It is possible not only to separate the organic impurities by the sublimation purification but also to effectively remove inorganic salts, residual solvents, water and the like.

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 more preferably contained in the layer on the cathode side adjacent to the light emitting layer.

<Protective layer>

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

As for the protective layer, the matters described in paragraphs [0169] to [0170] of Japanese Patent Application Laid-Open No. 2008-270736 can be applied to the present invention. The material of the protective layer may be an inorganic material or an organic material.

<Encapsulation container>

In the organic electroluminescent device of the present invention, the entire device may be sealed by using a sealing container.

As for the sealing container, the matters described in the paragraph [0171] of Japanese Laid-Open Patent Publication No. 2008-270736 can be applied to the present invention.

<Driving Method>

In the organic electroluminescent device of the present invention, light emission can be obtained by applying a direct current (which may contain an AC component if necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode.

The driving method of the organic electroluminescent device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP- The driving methods described in the specification of each of Japanese Patent Application Laid-Open No. 134558, Japanese Patent Application Laid-Open Nos. 8-234685 and 8-241047, Japanese Patent No. 2784615, USP 5828429 and USP 6023308 have.

The external quantum efficiency of the organic electroluminescent device of the present invention is preferably 7% or more, and more preferably 10% or more. The value of the external quantum efficiency can be the maximum value of the external quantum efficiency when the device is driven at 20 ° C or the value of the external quantum efficiency at 300 to 400 cd / m 2 when the device is driven at 20 ° C.

The internal quantum efficiency of the organic electroluminescent device of the present invention is preferably 30% or more, more preferably 50% or more, and still more preferably 70% or more. The internal quantum efficiency of the device 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%. However, considering the shape of the substrate, the shape of the electrode, the thickness of the organic layer, the thickness of the inorganic layer, the refractive index of the organic layer, To 20% or more.

&Lt; Light emission wavelength &

The light emitting wavelength of the organic electroluminescent device of the present invention is not limited. For example, among the three primary colors of light, it may be used for red light emission, green light emission, or blue light emission. Among them, the organic electroluminescent device of the present invention preferably has an emission peak wavelength of 490 to 580 nm in view of the luminous efficiency considering the lowest excitation triplet (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 an electron transporting material for a host material, an electron transporting layer, or a hole blocking layer of a luminescent layer, the luminescent peak wavelength is 490 To 580 nm, more preferably from 490 to 550 nm, and particularly preferably from 500 to 535 nm.

&Lt; Uses of Organic Electroluminescent Device of Present Invention >

The organic electroluminescent device of the present invention can be suitably used for a display device, a display, a backlight, an electrophotographic light, an illumination light source, a recording light source, an exposure light source, a reading light source, a cover, a signboard, an interior or an optical communication. Particularly, the light emitting device, the lighting device, the display device and the like are preferably used for a device driven in a high light emission luminance region.

[Light Emitting Device]

The light emitting device of the present invention is characterized by including the organic electroluminescent device of the present invention.

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

2 is a cross-sectional view schematically showing an example of a light emitting device of the present invention. 2 is constituted by a transparent substrate (support substrate) 2, an organic electroluminescence element 10, a sealing container 16, and the like.

The organic electroluminescent device 10 is constituted by sequentially laminating a positive electrode (first electrode) 3, an organic layer 11 and a negative electrode (second electrode) 9 on a substrate 2. An encapsulation container 16 is formed on the protective layer 12 with an adhesive layer 14 interposed therebetween. Further, a part of each of the electrodes 3 and 9, a partition wall, an insulating layer, and the like are omitted.

As the adhesive layer 14, a photo-curable adhesive such as an epoxy resin or a thermosetting adhesive may be used. For example, a thermosetting adhesive sheet may be used.

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

[Lighting Device]

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

Next, the lighting apparatus of the present invention will be described with reference to Fig.

3 is a cross-sectional view schematically showing an example of a lighting apparatus of the present invention. As shown in Fig. 3, the illumination device 40 of the present invention includes the above-described organic EL element 10 and a light scattering member 30. [ More specifically, the illumination device 40 is configured such that the substrate 2 of the organic EL element 10 and the light-scattering member 30 are in contact with 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 on the transparent substrate 31. [ As the transparent substrate 31, for example, a glass substrate is preferably used. As the fine particles 32, transparent resin fine particles are preferably used. As the glass substrate and transparent resin fine particles, all known ones can be used. When the 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 emits light from the light exit surface 30B as illumination light.

[Display device]

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

The display device of the present invention includes, for example, a display device such as a television, a personal computer, a cellular phone, or an electronic paper.

Example

Hereinafter, the present invention will be described in more detail with reference to examples. The materials, the amounts used, the ratios, the processing contents, the processing procedures, and the like shown in the following examples can be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention is not limited to the following specific examples.

[Examples 1 to 6]

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

(52)

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

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

¹ H-NMR data of the following compounds 1B-2, 1B-3, 1B-4, 1B-17, 1D-1 and 1D-3 synthesized in Examples 1 to 6 are shown in FIGS. 4 to 9, respectively.

(53)

Details of ¹ H-NMR data of the 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

¹ H-NMR (solvent): in DMSO, standard: tetramethylsilane)? (Ppm)

Compound 1B-3

¹ H-NMR (solvent): in CDCl ₃ , reference: tetramethylsilane)? (Ppm)

Compound 1B-4

¹ H-NMR (solvent): in CDCl ₃ , reference: tetramethylsilane)? (Ppm)

Compound 1B-17

¹ H-NMR (solvent): in CDCl ₃ , reference: tetramethylsilane)? (Ppm)

Compound 1D-1

¹ H-NMR (solvent): in CDCl ₃ , reference: tetramethylsilane)? (Ppm)

Compound 1D-3

¹ H-NMR (solvent): in CDCl ₃ , reference: tetramethylsilane)? (Ppm)

Thereafter, the compounds represented by the above-mentioned general formula (1) used in the production of an organic electroluminescent device to be described later and Comparative Compounds 1 to 4 having similar structures to each other were synthesized in the same manner as the compound 1B-2.

2. Fabrication and evaluation of organic electroluminescent devices

(2-A) Production of green electroluminescent organic electroluminescent device -1

Substantially all of the materials used for the production of the organic electroluminescent device were subjected to sublimation purification.

[Comparative Example 1]

(Preparation of positive electrode)

A glass substrate (surface resistance 10 Ω / □) having an ITO film with a thickness of 0.5 mm and a width of 2.5 cm was placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes .

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

(Lamination of organic layer)

Organic layers of the first to fifth layers were sequentially deposited on the above-described positive electrode by the vacuum deposition method using the following compounds. In addition, the structure of the compound used in each layer was shown.

Layer 1: LG101: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

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

Fourth layer: TpH-17: film thickness 10 nm

Layer 5: Alq: film thickness 40 nm

(54)

(Preparation of negative electrode)

On this, 0.1 nm of lithium fluoride and 200 nm of metallic aluminum were deposited in this order to form a negative electrode.

(Production of organic electroluminescence)

A laminate having five layers of organic layers between the cathode and the anode was placed in a glove box substituted with nitrogen gas without being brought into contact with the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, Nagaseichiba Co., Ltd.) To obtain an organic electroluminescent device of Comparative Example 1. [

(Evaluation of Organic Electroluminescent Device)

(a) Durability

The organic electroluminescent device of Comparative Example 1 was continuously lighted by applying a DC voltage at room temperature to a luminance of 5000 cd / m &lt; 2 &gt;, and the necessary time was measured until the luminance reached 4000 cd / m &lt; 2 &gt;. This time was regarded as an index of durability of the organic electroluminescent device.

In each of Examples and Comparative Examples described below, durability when using the organic electroluminescent device of Comparative Example 1 was set to 100 and durability relative values of less than 100 were evaluated as x, 100 Or more and less than 150 was rated as &amp; cir &amp;

Here, durability is preferable as the number increases.

(b) Color difference after storage at high temperature

The direct current voltage was applied to the organic EL device of Comparative Example 1 before storage (at 100 캜 for 48 hours) and after storage at a high temperature such that the luminance became 1000 cd / m 2, and the luminescence spectrum measurement system (manufactured by Shimadzu Corporation) ELS 1500), and the chromaticity (CIE chromaticity) was calculated.

The chromaticity after storage at high temperature (100 ° C for 48 hours) was found to differ by 0.01 or more from the x-coordinate or y-coordinate before storage and from the CIE (x, y) ◎.

(c) glass transition temperature

The glass transition temperature of Comparative Compound 1 used as the 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 those having a glass transition temperature Tg of less than 100 占 폚 as?, Those having a glass transition temperature of not less than 120 占 폚 as?

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

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

Also, the comparative compound 1 is the compound 2S described in International Publication WO2009 / 073245, the comparative compound 3 is the compound 2S described in International Publication WO2009 / 021126, and the comparative compound 4 is the compound compound 2 described in WO2009 / 02112 9S.

(55)

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

It can be seen from Table 1 that the organic electroluminescent devices of the respective Examples using the compounds represented by the general formula (1) of Examples A1 to A9 as the host compound in the light emitting layer are all excellent in durability and color difference after storage at high temperature . In addition, the compounds represented by the general formula (1) in Examples A1 to A9 had a good glass transition temperature.

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

The emission peak wavelengths of the organic electroluminescent devices prepared in Examples A1 to A9 were 515 to 535 nm.

(2-B) Production of green electroluminescent organic electroluminescent device-2

[Comparative Example 5]

The organic layer of the organic electroluminescent device of Comparative Example 1 was the same as Comparative Example 1 except that NPD used in the second layer was replaced with HTL-1 and GD-1 used in 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.

Layer 1: LG101: film thickness 10 nm

Second layer: HTL-1: film thickness 30 nm

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

Fourth layer: TpH-17: film thickness 10 nm

Layer 5: Alq: film thickness 40 nm

(56)

[Examples B1 to B4, Comparative Example 6]

In the same manner as in Comparative Example 5 except that the compound represented by the general formula (1) and the comparative compound 3 were used instead of the comparative compound 1 as the material for the third layer of the organic layer in Comparative Example 5, An organic electroluminescent device 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. [ Further, when the durability of the organic electroluminescent device of Comparative Example 5 was 100 and the relative value of the durability of the organic electroluminescent device of each of the other Examples and Comparative Examples was less than 100, A value of less than 150 was rated as?, And a value of 150 or more was evaluated as?.

The results are shown in Table 2 below.

From Table 2, it was found that the organic electroluminescent devices of the respective Examples using the compounds represented by the general formula (1) of Examples B1 to B6 as the host compound in the light emitting layer were all excellent in durability and color difference after storage at high temperature .

On the other hand, the organic electroluminescent device of Comparative Example 5 used Comparative Compound 1 as the host compound of the light emitting layer, and it was found that the durability was poor. The organic electroluminescent device of Comparative Example 6 used Comparative Compound 3 as the host compound of the light emitting layer and found that the chromaticity difference after storage at high temperature was poor.

The emission wavelength of the organic electroluminescent device manufactured in Examples B1 to B6 was 510 to 525 nm.

(2-C) Production of red electroluminescent organic electroluminescent device

[Comparative Example 7]

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

First layer: GD-1: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

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

Layer 4: Alq: film thickness 10 nm

Layer 5: Alq: film thickness 40 nm

(57)

[Examples C1 to C3 and Comparative Example 8]

The same procedure as in Comparative Example 7 was carried out except that the compound represented by the general formula (1) and the comparative compound 3 were used instead of the comparative compound 1 as the material for the third layer of the organic layer in Comparative Example 7, 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. [ The durability of the organic electroluminescent device of Comparative Example 7 was 100 and the relative value of the durability of the organic electroluminescent device of each of the other Examples and Comparative Examples was 100 or less, A value of less than 150 was rated as?, And a value of 150 or more was evaluated as?.

The results are shown in Table 3 below.

From Table 3, it was found that the organic electroluminescent devices of the respective Examples using the compounds represented by the general formula (1) of Examples C1 to C3 as the host compound of the light emitting layer were all excellent in durability and color difference after storage at high temperature .

On the other hand, the organic electroluminescent device of Comparative Example 7 used Comparative Compound 1 as the host compound of the light emitting layer, and it was found that the durability was poor. The organic electroluminescent device of Comparative Example 8 used Comparative Compound 3 as the host compound of the light emitting layer and found that the chromaticity difference after storage at high temperature was poor.

The emission wavelengths of the organic electroluminescent devices prepared in Examples C1 to C3 were 615 to 630 nm.

(2-D) Preparation of an organic electroluminescent device emitting green phosphorescence 3

[Comparative Example 9]

The device of Comparative Example 9 was fabricated in the same manner as in Comparative Example 5 except that TpH-17 used in the fourth layer of the device of Comparative Example 5 was changed to OM-8, and Alq used in the fifth layer was replaced by OM-8 . The structure of the organic layer in Comparative Example 9 is shown below.

Layer 1: LG101: film thickness 10 nm

Second layer: HTL-1: film thickness 30 nm

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

Layer 4: OM-8: film thickness 10 nm

Layer 5: OM-8: film thickness 40 nm

(58)

[Examples D1 to D5, Comparative Example 10]

In the same manner as in Comparative Example 9, except that the compound represented by the general formula (1) and the comparative compound 3 were used instead of the comparative compound 1 as the material for the third layer of the organic layer in Comparative Example 9, 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. [ Further, when the durability of the organic electroluminescent device of Comparative Example 9 was 100 and the relative value of the durability of the organic electroluminescent device of each of the other Examples and Comparative Examples was less than 100, A value of less than 150 was rated as?, And a value of 150 or more was evaluated as?.

The results are shown in Table 4 below.

It can be seen from Table 4 that the organic electroluminescent devices of the respective Examples using the compounds represented by the general formula (1) of Examples D1 to D5 as the host compound in the light emitting layer are all excellent in durability and color difference after storage at high temperature .

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

The emission wavelength of the organic electroluminescent device fabricated in Examples D1 to D5 was 510 to 525 nm.

(2-E) Preparation of an organic electroluminescent device with green phosphorescence-4

(Comparative Example 11)

The device of Comparative Example 11 was fabricated 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 used for the comparative compound 1 and Alq used for the fifth layer . The structure of the organic layer in Comparative Example 11 is shown below.

Layer 1: LG101: film thickness 10 nm

Second layer: HTL-1: film thickness 30 nm

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

Layer 4: Comparative Compound 1: Film thickness 10 nm

Layer 5: OM-8: film thickness 40 nm

[Chemical Formula 59]

[Examples E1 to E3, Comparative Example 12]

The compound represented by the general formula (1) or the comparative compound 3 was used instead of the comparative compound 1 as the material of the third layer of the organic layer in Comparative Example 11, and the compound The organic electroluminescent devices of Examples E1 to E3 and Comparative Example 12 were obtained in the same manner as in Comparative Example 11 except that the compound represented by Formula (1) or Comparative Compound 3 was used.

The organic electroluminescent devices of each of these Examples and Comparative Examples were evaluated in the same manner as in Comparative Example 1. [ The durability of the organic electroluminescent device of Comparative Example 11 was 100, the durability of the organic electroluminescent device of Comparative Examples 11 and 100 was 100, A value of less than 150 was rated as?, And a value of 150 or more was evaluated as?.

The results are shown in Table 5 below.

It can be seen from Table 5 that the organic electroluminescent devices of the respective examples 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 all exhibited good durability, I could see that.

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

In addition, the emission wavelength of the organic electroluminescent device manufactured in Examples E1 to E3 was 510 to 525 nm.

2 … Board
3 ... anode
4 … Hole injection layer
5 ... Hole transport layer
6 ... The light-
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 ... Sealing container
20 ... Light emitting device
30 ... Light scattering member
30A ... Light incidence plane
30B ... Light emitting surface
31 ... Transparent substrate
32 ... Particulate
40 ... Lighting device

Claims (14)

A substrate;
A pair of electrodes arranged 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 general formula (1)
An organic electroluminescent device in which compounds represented by the following general formulas (2) to (11) are excluded from the compound represented by the general formula (1)
In general formula (1)

In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (except for an alkyl group and a cyano group), and a plurality of R ¹⁰⁸ to R ¹¹⁰ represents L ¹⁰¹ may be the same or different and L ¹⁰¹ represents a single bond or an arylene group;
In general formula (2)

In the general formula (2), X ²⁰¹ represents an oxygen atom or a sulfur atom, each of R ²⁰¹ to R ²¹² independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ²⁰⁸ and R ²⁰⁹ may be the same It may be different, L ²⁰¹ represents a single bond or an arylene, p- terphenyl alkylene group not, a ²⁰¹ and a ²⁰² of one will be 10 to 30 of the aryl group, the condensed ring number of the ring atoms ring atoms in a condensed ring A heteroaryl group having 8 to 30 carbon atoms, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, And the other represents a hydrogen atom, an aryl group or a heteroaryl group;
In general 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 may be, L ³⁰¹ represents a single bond or arylene, a ³⁰¹ and a ³⁰² one has a condensed ring of ring atoms, of 10 to 30 aryl group, the number of fused rings of ring atoms 8-30 in the heteroaryl groups different from each other, An aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms or a monocyclic heteroaryl group having 5 to 25 ring atoms and having 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;

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 or different from each other, and 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 represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁵⁰⁸ to R ⁵¹³ may be the same And 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, and a plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same or different;

In 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 mutually the same Or may be different;

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 represent a hydrogen atom or an aryl group having 6 to 13 carbon atoms, A ¹¹ to ¹³ independently represent CH or a nitrogen atom, and at least one of them is a nitrogen atom. The method according to claim 1,
Wherein the compound has a molecular weight of 550 or more. The method according to claim 1,
Wherein the compound is a compound having a glass transition temperature of 100 DEG C or higher. The method according to claim 1,
Wherein the phosphorescent material is an iridium (Ir) complex represented by the following formula (E-1):

In formula (E-1), Z ¹ and Z ² each independently represent a carbon atom or a nitrogen atom, A ₁ represents an atom group forming a 5 or 6-membered heterocyclic ring together with Z ¹ and a nitrogen atom , 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, and n _E1 represents an integer of 1 to 3. 5. The method of claim 4,
An organic electroluminescent device characterized in that the iridium (Ir) complex represented by the general formula (E-1) is represented by the following general formula (E-2)

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

In the general formula (1), X ¹⁰¹ represents an oxygen atom or a sulfur atom, R ¹⁰¹ to R ¹¹⁰ represent a hydrogen atom or a substituent (except for an alkyl group and a cyano group), and a plurality of R ¹⁰⁸ to R ¹¹⁰ represents L ¹⁰¹ may be the same or different and L ¹⁰¹ represents a single bond or an arylene group;
In general formula (2)

In the general formula (2), X ²⁰¹ represents an oxygen atom or a sulfur atom, each of R ²⁰¹ to R ²¹² independently represents a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ²⁰⁸ and R ²⁰⁹ may be the same It may be different, L ²⁰¹ represents a single bond or an arylene, p- terphenyl alkylene group not, a ²⁰¹ and a ²⁰² of one will be 10 to 30 of the aryl group, the condensed ring number of the ring atoms ring atoms in a condensed ring A heteroaryl group having 8 to 30 carbon atoms, an aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms, or a monocyclic aryl group having 6 to 25 carbon atoms as a substituent, And the other represents a hydrogen atom, an aryl group or a heteroaryl group;
In general 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 may be, L ³⁰¹ represents a single bond or arylene, a ³⁰¹ and a ³⁰² one has a condensed ring of ring atoms, of 10 to 30 aryl group, the number of fused rings of ring atoms 8-30 in the heteroaryl groups different from each other, An aryl group having 6 to 25 carbon atoms or a heteroaryl group having 5 to 25 ring atoms or a monocyclic heteroaryl group having 5 to 25 ring atoms and having 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;

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 or different from each other, and 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 represent a hydrogen atom, an aryl group or a heteroaryl group, and a plurality of R ⁵⁰⁸ to R ⁵¹³ may be the same And 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, and a plurality of R ⁶⁰⁸ to R ⁶¹³ may be the same or different;

In 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 mutually the same Or may be different;

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 represent a hydrogen atom or an aryl group having 6 to 13 carbon atoms, A ¹¹ to ¹³ independently represent CH or a nitrogen atom, and at least one of them is a nitrogen atom. 13. The method of claim 12,
Wherein the compound has a molecular weight of 550 or more. 13. The method of claim 12,
Wherein said compound is a compound having a glass transition temperature of 100 DEG C or higher.

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