KR20140020935A - Charge transport material, organic electroluminescent element, and illumination device, display device, or light-emitting device characterized by using said element - Google Patents

Abstract

The charge transporting material composed of the compound represented by the following formula has a high efficiency after storage at a high temperature and has a high maximum luminance (R ¹⁰¹ , R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI > does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ , R ¹⁰² (In which the ring is a six-membered ring in which the ring atoms are constituted by carbon atoms or nitrogen atoms) in a total number of 5 or more. n ₁₀₁ Is an integer of 0 to 11, n ₁₀₂ Represents an integer of 0 to 9, and a plurality of R ¹⁰¹ , R ¹⁰² May be the same or different. A ^A1 ~ A ^A9 Each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.

Description

TECHNICAL FIELD [0001] The present invention relates to a charge transport material, an organic electroluminescent device, and a light emitting device, a display device, or a lighting device using the same, ELEMENT}

The present invention relates to a charge transport material, an organic electroluminescent device, and a light emitting device, a display device, or a lighting device using 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 holes injected from the anode are recombined in the organic layer, and the generated exciton energy is used for light emission.

In recent years, the use of phosphorescent light-emitting materials such as iridium (Ir) complexes and platinum (Pt) complexes has led to higher efficiency of devices. In addition, a doped device using a light emitting layer doped with a light emitting material into a host material is widely used.

Development of a host material used for a light emitting layer or a charge transporting material contained in another organic layer has been actively developed.

For example, Patent Document 1 discloses an organic electroluminescent device using a compound having a triphenylene structure, and discloses an organic electroluminescent device using an organic electroluminescent device using a phenylene-bonded compound having a substituent (aryl or heteroaryl in the non-condensed ring) An electroluminescent device is disclosed.

On the other hand, in recent years, various types of display devices including organic electroluminescent devices have been widely used, and it is demanded to stably operate for a long time under various environments. For example, in the case of vehicle use in automobiles and the like, it is required that the characteristics of the vehicle do not change even after storage at a high temperature since the vehicle becomes considerably high temperature during daytime driving or during parking. 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.

Japanese Unexamined Patent Publication No. 2010-535806

On the other hand, the inventors of the present invention have studied the characteristics of an organic electroluminescent device using the compound described in Patent Document 1. As a result, the efficiency after storage at a high temperature has been lowered and insufficient in terms of heat resistance, Found.

A problem to be solved by the present invention is to provide a charge transporting material and an organic electroluminescent device having high efficiency after storage at a high temperature and having a high maximum luminance.

As a result of intensive studies by the present inventors, it has been found that a compound having a triphenylene structure and a monocyclic aromatic ring structure is linked in a specific linking manner to a compound specifically described in Patent Document 1, The present inventors have found that a charge transporting material and an organic electroluminescent device having high efficiency after storage at a high temperature and having a high maximum luminance can be provided by increasing the number of directional rings of the die.

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

[1] A charge transporting material comprising a compound represented by the following general formula (1).

[Chemical Formula 1]

(In the general formula (1), R ¹⁰¹ and R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI > does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ and R ¹⁰² The total number of aromatic rings of the monocyclic rings contained in the aromatic ring (the aromatic ring is a six-membered ring composed of carbon atoms or nitrogen atoms) is 5 or more. n ₁₀₁ Is an integer of 0 to 11, n ₁₀₂ Represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² May be the same or different. A ^A1 ~ A ^A9 Each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.

[2] The charge transporting material according to [1], wherein the compound represented by the general formula (1) is represented by the following general formula (2).

(2)

(In the general formula (2), R ¹¹¹ independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted by these groups or amino groups.) R ²³¹ to R ²³⁴ Each independently represent an alkyl group, a fluorine atom, a silyl group or an amino group. R ²³⁵ to R ²³⁸ Each independently represent an aryl group or a heteroaryl group. Provided that R ¹¹¹ and R ²³¹ to R ²³⁸ Lt; / RTI > does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹¹¹ and R ²³¹ to R ²³⁸ (The aromatic ring is a six-membered ring in which the ring atom is composed of a carbon atom or a nitrogen atom) in a total number of 3 to 6. ₁₁₁ n represents an integer of 0 to 11, and y35 y33 y31 ~ ~ y37 are each independently an integer of 0 to 4, y34, and y38 represents an integer of 0-5. A plurality of R ¹¹¹ and R ²³¹ to R ²³⁸ May be the same or different. A ^B1 to A ^B17 Each independently represent CH (the hydrogen atom of CH may be substituted by R ²³¹ to R ²³⁸ ) or a nitrogen atom, and is a ring atom constituting an aromatic ring of a six-membered ring.

[3] A ^{compound according} to any one of [1] to [3] Represents a CH, and the hydrogen atom of A ^B3 is the above-mentioned R ²³⁵ And the substituent is substituted with at least one of a halogen atom,

[4] The positive resist composition according to [1], wherein n ₁₀₁ The charge transporting material according to any one of < 1 > to < 3 >

[5] A compound represented by the formula (1) wherein R ¹⁰¹ or R ¹⁰² Is any one of [1] to [4], wherein the substituent is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group or a substituent comprising a cycloalkylene group or a silicon atom- A charge transport material as claimed in any one of the preceding claims.

[6] The charge transporting material according to any one of [1] to [5], wherein the aromatic ring of all the monocyclic rings included in the general formula (1) is a six-membered ring of a carbon atom skeleton.

[7] The charge transporting material according to any one of [1] to [6], wherein the compound represented by the general formula (1) comprises only carbon atoms and hydrogen atoms.

[8] The charge transporting material according to any one of [1] to [7], wherein the compound represented by the general formula (1) has a molecular weight of 1,200 or less.

[9] The compound represented by the above-mentioned general formula (1), wherein the aromatic ring of the monocyclic ring (the ring of the ring is a six-membered ring in which the ring atom is composed of carbon atoms or nitrogen atoms) 1] to [8], wherein the number of the directional rings of the monolithic continuously connected at the para position in the partial structure is at most 3 The charge transport material described.

[10] 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, An organic electroluminescent device comprising the charge transport material according to any one of claims 1 to 12.

[11] The organic electroluminescent device according to [10], wherein the phosphorescent material is represented by the following general formula (E-1).

(3)

Of (Formula (E-1), x1 and Z ² Each independently represent a carbon atom or a nitrogen atom. A ₁ is Z ¹ And a group of atoms forming a 5- or 6-membered heterocyclic ring together with the nitrogen atom. B ₁ is Z ² And a group of atoms forming a 5 or 6-membered ring together with the carbon atom. (XY) represents a monoanionic two-position ligand. n _E1 represents an integer of 1 to 3.)

[12] The organic electroluminescent device according to [10] or [11], wherein the phosphorescent material represented by the general formula (E-1) is represented by the following general formula (E-2).

[Chemical Formula 4]

(In the general formula (E-2), A ^E1 to A ^E8 Each independently represent a nitrogen atom or a carbon atom substituted with R < ^{E &} gt ;. R ^E Represents a hydrogen atom or a substituent. (XY) represents a monoanionic two-position ligand. n _E2 Represents an integer of 1 to 3.)

[13] The organic electroluminescent device according to any one of [10] to [12], wherein the phosphorescence emitting material represented by the general formula (E-1) has a maximum emission wavelength of 500 nm to 700 nm.

[14] The organic electroluminescent device described in any of [10] to [13], wherein the organic layer has a light emitting layer containing the phosphorescent material and another organic layer, and the light emitting layer contains the compound represented by the general formula (1) And the organic electroluminescent device described in the item (1).

[15] The organic light-emitting device according to any one of [1] to [6], wherein the organic layer has a light-emitting layer containing the phosphorescent material and another organic layer, and the other organic layer includes a hole- The organic electroluminescent device according to any one of [10] to [14], wherein the compound represented by the general formula (1) is contained.

[16] The organic electroluminescent device according to any one of [10] to [15], wherein the maximum light emission wavelength is 500 nm to 550 nm.

[17] A light emitting device, a display device, or a lighting device, comprising the organic electroluminescent device according to any one of [10] to [16].

[18] A compound represented by the following general formula (1).

[Chemical Formula 5]

(In the general formula (1), R ¹⁰¹ and R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI > does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ and R ¹⁰² (In which the ring is a six-membered ring in which the ring atoms are constituted by carbon atoms or nitrogen atoms) in a total number of 5 or more. n ₁₀₁ is an integer of 0 to 11, n ₁₀₂ Represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² May be the same or different. A ^A1 ~ A ^A9 Each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.

By using the compound represented by the general formula (1) in the present invention, it is possible to provide a charge transporting material and an organic electroluminescent device having high efficiency after storage at a high temperature and having the highest luminance achieved.

1 is a schematic view showing an example of the configuration of an organic electroluminescence 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.

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.

[Charge transporting material]

The charge transporting material of the present invention is characterized by comprising a compound represented by the following general formula (1).

[Chemical Formula 6]

(In the general formula (1), R ¹⁰¹ and R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI > does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ and R ¹⁰² (In which the ring is a six-membered ring in which the ring atoms are constituted by carbon atoms or nitrogen atoms) in a total number of 5 or more. n ₁₀₁ is an integer of 0 to 11, n ₁₀₂ Represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² May be the same or different. A ^A1 ~ A ^A9 Each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.

The charge transporting material of the present invention has such a structure that it can increase the glass transition temperature Tg without impairing the efficiency and drive durability, and can also increase the molecular excitation state, the radical cation state, the radical The excited state and the electric charge are diffused in the? -Conjugated system which is wide in the molecule when it is in the no-on state, so that the device characteristics after storage at high temperature are excellent and stable driving can be achieved also against the concentration of excitons . Therefore, the organic electroluminescent device using the charge transport material of the present invention has excellent efficiency after storage at a high temperature and excellent maximum luminance.

The charge transporting material of the present invention represented by the above general formula (1) can be preferably used for an organic electronic device such as an electrophotographic photoconductor, an organic transistor, an organic photoelectric conversion element (energy conversion use, sensor use, etc.) And it is particularly preferable to use it in an organic electroluminescent device.

The charge transporting material of the present invention can also be used as a thin film containing the compound represented by the above general formula (1). The thin film can be formed by a wet film-forming method such as a dry film forming method such as a vapor deposition method or a sputter method, a transfer method, a printing method, or the like using the above composition. The thickness of the thin film may be any thickness depending on the application, but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 탆, further preferably 1 nm to 200 nm, particularly preferably 1 nm nm to 100 nm.

Hereinafter, a preferable range of the charge transporting material composed of the compound represented by the general formula (1) will be described.

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

In the present invention, when a "substituent" is referred to, the substituent may be substituted. For example, the "alkyl group" in the present invention includes an alkyl group substituted with a fluorine atom (for example, a trifluoromethyl group) or an alkyl group substituted with an aryl group (for example, a triphenylmethyl group) An alkyl group having 1 to 6 carbon atoms ", all of the groups including a substituted group are those having 1 to 6 carbon atoms.

In the present invention, a substituent group containing a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, a cycloalkylene group or a silicon atom-linking group is also referred to as a "specific substituent". Also, the silyl substituted with an alkyl group and an aryl group is included in the above specific substituent group.

In the present specification, the term "cycloalkylene group" means a generic term such as 1,4-cyclohexanediyl, 1,3-cyclohexanediyl, 1,2-cyclohexanediyl, cyclopentane, etc., Does not mean a ring of one hydrogen atom.

<R ¹⁰¹ and R ^{102 in the} general formula (1)

In the general formula (1), R ¹⁰¹ and R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI &gt; does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ and R ¹⁰² (In which the ring is a six-membered ring in which the ring atoms are constituted by carbon atoms or nitrogen atoms) in a total number of 5 or more. The ring atoms of the monocyclic ring (the ring in the ring is a six-membered ring composed of a carbon atom or a nitrogen atom) of the monocyclic ring in the general formula (1) The number of valences is preferably 3 or less, more preferably 2 or less, particularly preferably 1 or less, and particularly preferably 0.

In the general formula (1), R ¹⁰¹ and R ¹⁰² (The aromatic ring is a six-membered ring in which the ring atom is composed of a carbon atom or a nitrogen atom) in the total number of 5 or more, whereby the effect of the present invention can be exhibited. R ¹⁰¹ and R ¹⁰² Is preferably from 5 to 8, more preferably from 5 to 7, and particularly preferably from 5 to 6, from the viewpoint of deposition suitability.

The R ¹⁰¹ and R ¹⁰² Is an alkyl group, the alkyl group may be a linear chain, a branched chain or a cyclic group, and generally has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, An alkyl group having 1 to 6 carbon atoms, and most preferably 1 to 4 carbon atoms. For example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- An ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isopropyl group, an isopropyl group, a n-butyl group, More preferably a methyl group, an ethyl group, a n-propyl group, a t-butyl group and a cyclohexyl group, particularly preferably a methyl group, an isopropyl group, , An isopropyl group and a t-butyl group, and still more preferably a methyl group or a t-butyl group.

The alkyl group as R ¹⁰¹ and R ¹⁰² may further have an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group as a substituent. Among them, an aryl group, a heteroaryl group or a group substituted with a fluorine atom is preferable.

When the alkyl group as R &lt; ¹⁰¹ &gt; and R &lt; ¹⁰² &gt; is substituted with a fluorine atom, it is more preferable that all the hydrogen atoms are substituted with fluorine atoms to form a perfluoroalkyl group, and -CF ₂ CF ₂ CF ₃ Or a trifluoromethyl group is particularly preferable, and it is more preferable that a trifluoromethyl group is formed.

On the other hand, when the alkyl group as R ¹⁰¹ and R ¹⁰² is substituted with an aryl group or a heteroaryl group, the aryl group or heteroaryl group may be substituted by a monocyclic aromatic ring (the aromatic ring may be a 6-membered ring in which the ring atom is a carbon atom or a nitrogen atom Ring). In this case, it is preferable that the alkyl group as R ¹⁰¹ and R ¹⁰² is substituted with a plurality of monocyclic rings (the ring is a six-membered ring in which the ring atoms are composed of carbon atoms or nitrogen atoms).

When the alkyl group as R &lt; ¹⁰¹ &gt; and R &lt; ¹⁰² &gt; is further substituted with an alkyl group, the alkyl group as the additional substituent is preferably a methyl group.

It is more preferable that the alkyl group as R ¹⁰¹ and R ¹⁰² is substituted to be a quaternary carbon.

The R ¹⁰¹ and R ¹⁰² Is a silyl group, the silyl group is preferably substituted, and the substituent is preferably an alkyl group or an aryl group. When the silyl group as R ¹⁰¹ and R ¹⁰² is substituted with an alkyl group or an aryl group, it is more preferable that all hydrogen atoms are substituted with an alkyl group or an aryl group to form a trialkylsilyl group or a triarylsilyl group, and a trimethylsilyl group or a triphenylsilyl group Group is particularly preferable. The aryl group portion of the triarylsilyl group may be further substituted, and in this case, it is preferably substituted with an aryl group, and more preferably substituted with a phenyl group.

The R ¹⁰¹ and R ¹⁰² Is a heteroaryl group, the heteroaryl group is preferably a 5- or 6-membered heterocyclic ring containing a nitrogen atom. Examples of the 5- or 6-membered heterocyclic ring containing the nitrogen atom include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, A thiazole ring, a thiadiazole ring and the like. When the charge-transporting material of the present invention is used in an organic electroluminescent device, it is preferable to use a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole ring in view of stability of a complex, control of an emission wavelength, Particularly 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. However, the R ¹⁰¹ and R ¹⁰² Is preferably an aryl group rather than a heteroaryl group.

The R ¹⁰¹ and R ¹⁰² Is an aryl group, it preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, naphthyl, anthryl and the like. The R ¹⁰¹ and R ¹⁰² Is preferably a monocyclic aryl group, and more preferably a phenyl group.

The aryl group or heteroaryl group as R ¹⁰¹ and R ^{102 may} further have an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group or an amino group as a substituent.

Wherein R ¹⁰¹ and R ¹⁰² groups, or an aryl group as a heteroaryl group, an alkyl group, when a fluorine atom or a silyl group is substituted, the preferred range of the alkyl group as the substituent, a heteroaryl group, a fluorine atom or a silyl group is, R ¹⁰¹ and R ¹⁰² Is an alkyl group, a heteroaryl group, a fluorine atom or a silyl group. Wherein R ¹⁰¹ and if R ¹⁰² an aryl group or groups heteroaryl as a group, a heteroaryl group, a fluorine atom, or is a silyl group is substituted, the number of these substituents is from 1 to 3 for the aryl group or heteroaryl as said R ¹⁰¹ and R ¹⁰² aryl More preferably 1 or 2, and particularly preferably 1.

When the amino group is substituted with an aryl group or a heteroaryl group as R ¹⁰¹ and R ¹⁰² , it is preferable that the amino group is further substituted with an alkyl group, an aryl group or a heteroaryl group, and the amino group is a tertiary amine More preferable. The preferable range of the alkyl group, aryl group or heteroaryl group further substituting the amino group in this case is the same as the preferable range of the alkyl group, aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² described above.

When the aryl group or the heteroaryl group as R ¹⁰¹ and R ¹⁰² is substituted with an aryl group or a heteroaryl group, the aryl group and the arylene group formed by substitution or the heteroaryl group and the heteroarylene group are both monocyclic And more preferably all of six-membered rings.

An aryl group or a heteroaryl group may be substituted for the aryl group or the heteroaryl group as R ¹⁰¹ and R ^{102 to form} an aryl group and an arylene group each having 6-membered rings or a heteroaryl group and a heteroarylene group, The number of monocyclic rings of six-membered rings connected by a single bond is preferably 2 to 6, more preferably 2 to 6, To 5, particularly preferably 2 to 4) are preferable. For example, a preferred structure when the aryl group and the arylene group of the six-membered ring form a linking substituent include biphenyl, terphenyl, quaterphenyl, and quinphenyl.

The monovalent substituent group of the 6-membered ring having plural monocyclic groups connected to each other through a plurality of monocyclic rings is a monocyclic ring in which monocyclic rings (the ring is a six-membered ring in which the ring atoms are composed of carbon atoms or nitrogen atoms) , And the number of directional rings of the monolith continuously connected at the para position in the partial structure is preferably 3 or less. That is, it is preferable that the monovalent substituent of the 6-membered ring, which is connected to a plurality of monocyclic rings by a single bond, does not contain more than three para-substituted phenyl rings.

Of these, the monovalent substituent of the 6-membered ring which is connected in plural to the monocyclic ring by a single bond is preferably a phenyl group, a biphenyl group, a terphenyl group (particularly a p-terphenyl group or a 3,5-diphenylphenyl group, , More preferably a biphenyl group or a terphenyl group, and most preferably a biphenyl group. The above examples also have the same structure when a heteroaryl group and a heteroarylene group are connected.

The R ¹⁰¹ Is an aryl group or a heteroaryl group, it is particularly preferable that R ¹⁰¹ is represented by the following general formula (3).

(7)

( ^Wherein A ^A11 to A ^A33 Each independently represents CH or a nitrogen atom, and is a ring atom constituting an aromatic ring of a six-membered ring. R ²⁰¹ to R ²⁰⁴ Y1 to y3 each independently represents an integer of 0 to 4, and y4 represents an integer of 0 to 5, and each of Y1 to Y3 independently represents an alkyl group, a fluorine atom or a silyl group. R ²⁰⁵ to R ²⁰⁸ Each independently represents an aryl group or a heteroaryl group, and y5 to y8 each independently represent an integer of 0 to 2. However, the sum of y1 and y5, the sum of y2 and y6, and the sum of y3 and y7 are at most four, and the sum of y4 and y8 is at most five. x1, x2 and x3 each independently represent 0 or 1, and x1 &lt; = x2 &lt; = x3.

In the general formula (3), the preferable range of R ²⁰¹ to R ²⁰⁴ is the same as the preferable range of the alkyl group, fluorine atom or silyl group as R ¹⁰¹ and R ^{102 in} the general formula (1). Among them, R ²⁰¹ to R ²⁰⁴ Is preferably an alkyl group or a fluorine atom, more preferably a methyl group, an n-propyl group or a fluorine atom.

In the general formula (3), the preferable range of R ²⁰⁵ to R ²⁰⁸ is the same as the preferable range of the aryl group or heteroaryl group as R ¹⁰¹ and R ^{102 in} the general formula (1). Among them, R ²⁰⁵ to R ²⁰⁸ Is preferably an aryl group, more preferably a phenyl group.

In the general formula (3), the sum of y5 to y8, that is, R ¹⁰¹ , The number of branches of the aromatic ring of the 6-membered ring is preferably 0 or 1, and particularly preferably 0.

In the general formula (3), when x1 to x3 are 1, y1 to y3 are preferably 0, y4 is preferably 0 to 2, and y5 to y8 are preferably 0. In this case, R ²⁰¹ is preferably an alkyl group, more preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group or an n-propyl group.

In the general formula (3), when x1 is 0, and x2 and x3 are 1, y1 is preferably 0 to 2, and y2 to y8 are preferably all 0. In this case, R &lt; ²⁰¹ &gt; is preferably an alkyl group, more preferably a methyl group.

In the general formula (3), when x1 and x2 are 0 and x3 is 1, it is preferable that y1 to y6 are 0, y7 is 1, and y8 is 0. At this time, R ²⁰⁷ Is preferably an aryl group, more preferably a phenyl group.

In the general formula (3), when x1 to x3 are 0, y1 to y3 are preferably 0, y4 is preferably 0 or 1, and y5 to y8 are preferably 0. In this case, R &lt; ²⁰¹ &gt; is preferably a fluorine atom.

Among the aromatic rings of the six-membered rings constituted by A ^A11 to A ^A33 in the general formula (3), one or more rings containing a nitrogen atom is preferable, and 0 is more preferable.

In the general formula (3), there is no limitation on the connection of the aromatic ring of each 6-membered ring, but it is preferably connected at the meta position or the para position, and at least the aromatic ring of the 6-membered ring represented by x1, It is particularly preferable that the aromatic ring of the 6-membered ring is connected at the meta position, and that the aromatic rings of all the 6-membered rings are connected at the meta position.

Next, the R ¹⁰² Is an aryl group or a heteroaryl group, the R ¹⁰² Is particularly preferably a substituent represented by the following general formula (4).

[Chemical Formula 8]

( ^Wherein A ^A41 to A ^A69 Each independently represents CH or a nitrogen atom, and is a ring atom constituting an aromatic ring of a six-membered ring. R ²¹¹ to R ²¹⁵ Each independently represent an alkyl group, a fluorine atom, a silyl group or an amino group, y11 to y14 each independently represent an integer of 0 to 4, and y15 represents an integer of 0 to 5. R ²¹⁶ to R ²²⁰ Each independently represents an aryl group or a heteroaryl group, and y16 to y20 each independently represent an integer of 0 to 2. However, the sum of y11 and y16, the sum of y12 and y17, the sum of y13 and y18, and the sum of y14 and y19 are maximum 4, and the sum of y15 and y20 is maximum 5. x11, x12, x13 and x14 each independently represent 0 or 1, and x11 &lt; = x12 &lt; = x13 &

In the general formula (4), the preferable range of R ²¹¹ to R ²¹⁵ is the same as the preferable range of the alkyl group, fluorine atom or silyl group as R ¹⁰¹ and R ^{102 in} the general formula (1). Provided that it may be a substituted or unsubstituted amino group. Among them, R ²¹¹ to R ²¹⁵ Is preferably an alkyl group, a fluorine atom, a silyl group or an amino group, more preferably an alkyl group, a fluorine atom or a silyl group.

In the general formula (4), the preferable range of R ²¹⁶ to R ²²⁰ is the same as the preferable range of the aryl group or the heteroaryl group as R ¹⁰¹ and R ^{102 in} the general formula (1). Among them, R ²¹⁶ to R ²²⁰ Is preferably an aryl group, more preferably a phenyl group.

In the general formula (4), the sum of y16 to y20, that is, R ¹⁰² Is preferably 0 to 2, more preferably 0 or 1, and particularly preferably 0. The number of branching rings in the 6-membered ring is preferably 0 to 2, more preferably 0 or 1,

In the general formula (4), when x11 to x14 are 1, y11 is preferably 0, y12 is preferably 0 or 1, and y13 to y20 are preferably 0. When y12 is 1, R ²¹² Is preferably an alkyl group, preferably an alkyl group substituted with a fluorine atom, more preferably a perfluoroalkyl group, and particularly preferably a perfluoroalkyl group having 3 carbon atoms.

In the general formula (4), when x11 is 0 and x12 to x14 are 1, y12 is preferably 0 or 1, y13 is preferably 0, y14 is 0 or 1, y15 And y17 is preferably 0, y18 is preferably 0 or 1, and y19 and y20 are preferably 0. At this time, R ²¹² and R ²¹⁴ Are preferably each independently an alkyl group, more preferably a t-butyl group. R ²¹⁸ Is preferably an aryl group, more preferably an aryl group substituted with a fluorine atom, more preferably a perfluoroaryl group, and particularly preferably a perfluoroaryl group having 6 carbon atoms.

In the general formula (4), when x11 and x12 are 0, and x13 and x14 are 1, y13 is preferably 0 or 1, y14 is preferably 0, y15 is preferably 0 or 1, , y18 and y19 are preferably 0 or 1, and y20 is preferably 0. At this time, R ²¹³ Is preferably an alkyl group, a fluorine atom or a silyl group, more preferably a silyl group substituted by an alkyl group substituted by a fluorine atom, a fluorine atom or an alkyl group, and particularly preferably a perfluoromethyl group, a fluorine atom, or a trimethylsilyl group. R ²¹⁵ Is preferably an alkyl group, more preferably an isopropyl group. R ²¹⁸ and R ²¹⁹ Is preferably an aryl group, and more preferably a phenyl group.

In the general formula (4), when x11 to X13 are 0 and x14 is 1, y14 is preferably 0 to 2, y15 is preferably 0 to 2, y19 is preferably 0 to 2, , and y &lt; 20 &gt; At this time, R ²¹⁴ Is preferably an alkyl group or a silyl group, more preferably a silyl group substituted with an alkyl group or an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group, an isopropyl group or a dimethylphenylsilyl group. R ²¹⁵ Is preferably an alkyl group, a silyl group or an amino group, more preferably a linear or branched alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, a silyl group substituted with an aryl group or an amino group substituted with an aryl group, more preferably a triphenylmethyl group, Particularly preferred are amino groups substituted by ethyl, isopropyl, n-propyl, t-butyl, cyclohexyl, triphenylsilyl or 3 ', 5'-dimethylbiphenylene. R ²¹⁵ Is preferably an aryl group, more preferably a phenyl group.

In the general formula (4), when x11 to X14 are 0, y15 is preferably 0 to 2, and y20 is preferably 0. At this time, R ²¹⁵ Is preferably an alkyl group, more preferably a methyl group or a t-butyl group.

Wherein the general formula (4) in the direction of the ring, A ~ ^A41 6-membered ring constituted by A ^A69, preferably a ring containing the nitrogen atom to not more than 1, more preferably 0 individual.

In the general formula (4), there is no limitation on the connection of the aromatic ring of each 6-membered ring, but it is preferably connected at the meta position or the para position, and at least the aromatic ring of the 6-membered ring represented by x11, It is more preferable that the aromatic ring of the 6-membered ring is connected at the para position. However, it is preferable that the number of the aromatic rings of the six-member rings is three or less at the para position.

R ¹⁰¹ in the general formula (1) represents a substituent group containing a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group or a cycloalkylene group or a silicon atom- ), But may be an embodiment in which one or more of the above specific substituents are not contained. In the present invention, R &lt; ¹⁰¹ &gt; in the above general formula (1) A fluoroalkyl group, or an alkylsilyl group, or an embodiment that does not contain any one of the above specific substituents is preferable, and an embodiment that does not include any one of the specific substituents is more preferable.

R ¹⁰¹ in the general formula (1) is preferably an aryl group which may have a substituent, and among the alkyl group, aryl group, heteroaryl group, fluorine atom or silyl group, the aryl group represented by the general formula (3) , And particularly preferably an aryl group in which X1 in the general formula (3) is 0 and X2 and X3 are 1 and an aryl group in which all of y1 to y8 in the general formula (3) are all 0 , Unsubstituted m-terphenylene.

The R ¹⁰² in the general formula (1) May be any of a group comprising any of a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, or a substituent group containing a cycloalkylene group or a silicon atom-linking group (the above specific substituent) In the present invention, R ¹⁰² in the general formula (1) Is an aryl group, a fluoroalkyl group, a cycloalkyl group, or an alkylsilyl group is preferable, and an embodiment wherein a cycloalkyl group, an alkylsilyl group, or an arylsilyl group is more preferable, and an embodiment wherein an alkylsilyl group or an arylsilyl group is included Particularly preferred.

The R ¹⁰² in the general formula (1) Is preferably a heteroaryl group which may have a substituent or an aryl group which may have a substituent, and particularly preferably an aryl group represented by the general formula (4), among the alkyl group, aryl group, heteroaryl group, fluorine atom or silyl group.

In the general formula (3) or (4), the number of the six-membered rings is preferably three or less at the para position. For example, when the terminal of the p-terphenylene group is further connected to the ring of the 6-membered ring, it is preferably connected at the meta position or the ortho position, and more preferably at the meta position.

&Lt; n101 and n102 in the general formula (1) &gt;

In the general formula (1), n ₁₀₁ represents an integer of 0 to 11, preferably an integer of 0 to 2, more preferably 0 or 1, and most preferably 0.

In the above general formula (1), n ₁₀₁ Is not 0, the R ¹⁰¹ The position to be substituted with the triphenylene ring structure is not particularly limited, but in the general formula (1), it is preferable to have a substituent R ¹⁰¹ in addition to the ring in which the triphenylene ring is connected to the biphenylene structure.

In the above general formula (1), n ₁₀₂ Represents an integer of 0 to 7, preferably an integer of 1 to 6, particularly preferably an integer of 1 to 5, more preferably an integer of 1 to 2.

In the above general formula (1), n ₁₀₂ Is not 0, the R ¹⁰² Is not particularly limited as long as it is substituted with a biphenylene structure. In the biphenylene structure of the general formula (1), at least one substituent R ¹⁰² is preferable, and at least one substituent R ¹⁰² is bonded to both the ring of the six-membered ring bonded to the triphenylene ring structure and the ring of the six-membered ring not bonded to the triphenylene structure .

Further, it is preferable that at least one of the hexagonal rings of the hexagonal ring side bonded to the triphenylene ring structure and the hexagonal ring side of the side not bonded to the triphenylene structure , And the ring atom is a six-membered ring composed of a carbon atom or a nitrogen atom).

In the charge transport material of the present invention, it is preferable that the compound represented by the above general formula (1) is represented by the following general formula (2).

[Chemical Formula 9]

In the general formula (2), R ¹¹¹ independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. R ²³¹ to R ²³⁴ Each independently represent an alkyl group, a fluorine atom, a silyl group or an amino group. R ²³⁵ to R ²³⁸ Each independently represent an aryl group or a heteroaryl group. Provided that R ¹¹¹ and R ²³¹ to R ²³⁸ Lt; / RTI &gt; does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹¹¹ and R ²³¹ to R ²³⁸ (The aromatic ring is a six-membered ring in which the ring atom is composed of a carbon atom or a nitrogen atom) in a total number of 3 to 6. ₁₁₁ n represents an integer of 0 to 11, and y35 y33 y31 ~ ~ y37 are each independently an integer of 0 to 4, y34, and y38 represents an integer of 0-5. A plurality of R ¹¹¹ and R ²³¹ to R ²³⁸ May be the same or different. A ^B1 to A ^B17 Each independently represent CH (the hydrogen atom of CH may be substituted by R ²³¹ to R ²³⁸ ) or a nitrogen atom, and is a ring atom constituting an aromatic ring of a six-membered ring.

The preferable range of R ¹¹¹ and n ₁₁₁ in the general formula (2) is the same as the preferable ranges of R ¹⁰¹ and n ₁₀₁ in the general formula (1).

In the general formula (2), A ^B1 to A ^B17 Is preferably the same as the preferable range of the aryl group or the heteroaryl group as R ¹⁰¹ and R ^{102 in} the general formula (1).

A preferable range of R ²³¹ to R ²³⁴ in the general formula (2) is a preferable range of an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, or a silyl group as R ¹⁰¹ and R ^{102 in} the general formula (1) . However, R ²³¹ to R ²³⁴ May be a substituted or unsubstituted amino group. Among them, R ²³¹ to R ²³⁴ Is preferably an alkyl group, an aryl group, a fluorine atom or a silyl group, more preferably a silyl group.

In the general formula (2), the preferable range of R ²³⁵ to R ²³⁸ is the same as the preferable range of the aryl group or heteroaryl group as R ¹⁰¹ and R ^{102 in} the general formula (1). Among them, R ²³⁵ to R ²³⁸ Is preferably an aryl group, more preferably a p-terphenylene group.

In the general formula (2), the sum of y35 to y38 is preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0 to 1.

In the general formula (2), y31 is preferably 0 or 1. In this case, R ²³¹ is preferably an alkyl group or a silyl group, more preferably a methyl group or an aryl group-substituted silyl group, particularly preferably a methyl group or a triphenylsilyl group, and a triphenylsilyl group Or a phenyl group of 2 is also preferable).

In the general formula (2), y32 is preferably 0 to 3, more preferably 0 or 1. At this time, R ²³² Is preferably an alkyl group, a fluorine atom, a silyl group or an amino group, more preferably an unsubstituted or fluorine-substituted alkyl group, a fluorine atom, an alkyl group or an aryl group-substituted silyl group or an amino group substituted with a phenyl group, It is particularly preferably a group in which an atom, a trifluoromethyl group, a trimethylsilyl group, a triphenylsilyl group or an amino group is substituted with two phenyls, more preferably a methyl group, a fluorine atom or a trimethylsilyl group.

In the general formula (2), y33 is preferably 0 or 1. At this time, R ²³³ Is preferably a silyl group, more preferably a silyl group substituted with at least one of an alkyl group and an aryl group, particularly preferably a silyl group substituted with an alkyl group and an aryl group, more preferably a silyl group substituted with a methyl group and a phenyl group .

In the general formula (2), y34 is preferably 0 or 1. At this time, R ²³⁴ Is preferably an alkyl group, a silyl group or an amino group, more preferably a silyl group substituted with an alkyl group, an aryl group or a phenyl group, more preferably an ethyl group (which may further have a substituent), an n-propyl group, More preferably a group substituted with a methyl group, a butyl group, a trimethylsilyl group, a triphenylsilyl group or an amino group with two biphenyls (which may further have a methyl group as a substituent).

In the general formula (2), y35 is preferably 0 or 1. At this time, R ²³⁵ Is preferably an aryl group, more preferably a phenyl group, a biphenyl group, an m-terphenyl group, a p-terphenyl group or a group in which these groups are further substituted. The additional substituent is preferably an alkyl group, a fluorine atom, a silyl group or an aryl group, and more preferably a trifluoromethyl group, a triphenylmethyl group, an isopropyl group, a t-butyl group, a trimethylsilyl group or a phenyl group.

In the general formula (2), y36 is preferably 0 or 1. At this time, R ²³⁶ Is preferably an aryl group, more preferably a phenyl group, a dimethylphenyl group, a group in which a biphenyl group is substituted with two phenyl groups, a p-terphenylene group, and particularly preferably a phenyl group or a p-terphenylene group.

In the general formula (2), y37 is preferably 0.

In the general formula (2), y38 is preferably 0 or 1. At this time, R ²³⁸ Is preferably an aryl group, more preferably a phenyl group, a biphenyl group, or a p-terphenylene group.

Among the aromatic rings of the six-membered rings constituted by A ^B1 to A ^B17 in the general formula (2), the number of rings containing a nitrogen atom is preferably 1 or less, more preferably 0.

In the general formula (2), there is no limitation on the linking of the aromatic ring of each 6-membered ring, but it is preferable that the ring is connected at the meta position or the para position.

In the present invention, in the above-mentioned formula (2), A ^B3 Represents a CH, and the hydrogen atom of A ^B3 is the above-mentioned R ²³⁵ , And the like.

The compound represented by the general formula (1) is preferably a six-membered ring of a carbon atom skeleton of all the monocyclic rings included in the general formula (1), more preferably a carbon atom and a hydrogen atom only .

The compound represented by the above general formula (1) is preferably a compound having four or more aromatic rings (whose ring is a six-membered ring in which the ring atoms are composed of carbon atoms or nitrogen atoms) It is preferable from the viewpoint of using a green phosphorescent material that at least one partial structure is present and the number of directional rings of said monolith continuously connected at the para position in said partial structure is 3 or less. In addition, this substrate does not exclude the embodiment in which the number of directional rings of the monolithically connected monolith continuously connected at the para position is 4, and the number of directional rings of the monolith continuously connected at the para position is 4 The individual compound is preferable from the viewpoint of using a red phosphorescent material.

More preferably, the compound represented by the general formula (1) includes a phenyl ring which is a partial structure of an axial ring constituting the triphenylene ring, and the number of directional rings continuously connected at the para position is preferably 3 or less Do.

In the film state of the compound represented by the general formula (1), T ₁ The energy is preferably 2.39 eV (55.0 kcal / mol) to 3.25 eV (75.0 kcal / mol), more preferably 2.47 eV (57.0 kcal / mol) to 3.04 eV (70.0 kcal / mol) (58.0 kcal / mol) to 2.82 eV (65.0 kcal / mol) or less. Particularly, when a phosphorescent material is used as the light emitting material, T ₁ It is preferable that the energy falls within the above range.

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

In the charge transport material of the present invention, the molecular weight of the compound represented by the general formula (1) is preferably 1200 or less, more preferably 1000 or less, still more preferably 750 or more and 1000 or less, particularly preferably 750 or more and 900 or less And most preferably not less than 750 and not more than 850. When the molecular weight is within this range, a material excellent in film quality and excellent in sublimation purification and deposition suitability can be obtained.

The glass transition temperature (Tg) of the compound represented by the general formula (1) is preferably 80 占 폚 or more and 400 占 폚 or less, more preferably 100 占 폚 or more and more preferably 100 占 폚 or more, from the viewpoints of stably operating the organic electroluminescent device against heat generation during high- More preferably 400 DEG C or lower, and still more preferably 120 DEG C or higher and 400 DEG C or lower.

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

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

The compounds represented by the above general formula (1) are disclosed in Japanese Laid-Open Patent Publication Nos. 2004-43349, 2004-83481, US2006 / 0280965, WO2009 / 021107, JP-A-2009-114068, 2010-535806 or the like, or by combining other known reactions.

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.

[Organic electroluminescent device]

The 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, , That is, a compound represented by the above general formula (1).

[Chemical Formula 14]

(In the general formula (1), R ¹⁰¹ and R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI &gt; does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ and R ¹⁰² (In which the ring is a six-membered ring in which the ring atoms are constituted by carbon atoms or nitrogen atoms) in a total number of 5 or more. n ₁₀₁ is an integer of 0 to 11, n ₁₀₂ Represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² May be the same or different. A ^A1 ~ A ^A9 Each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.

The structure of the organic electroluminescent device of the present invention is not particularly limited. Fig. 1 shows an example of the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device 10 of Fig. 1 has an organic layer between a pair of electrodes (an anode 3 and a 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 Application Laid-Open 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 substrate, electrode, organic layer, protective layer, encapsulation container, driving method, 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 which does not scatter or attenuate light generated 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, and the shape, structure, and size of the anode are suitably selected from known electrode materials according to the purpose and purpose of the light- . 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, and the shape, structure, and size of the anode are suitably selected from known electrode materials depending on the use and purpose of the light- .

<Organic layer>

The organic electroluminescent device of the present invention has an organic layer disposed between the electrodes, and the organic layer includes 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, the organic layer is formed on the entire surface or one surface of the transparent electrode or the translucent electrode.

The shape, size, thickness, etc. of the organic layer are not particularly limited and can 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 element 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 transporting 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 can be given. 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 with low cost and high efficiency.

In the organic electroluminescent device of the present invention, it is preferable that the organic electroluminescent device 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). Further, in the organic electroluminescent device of the present invention, it is more preferable that the organic layer has a light emitting layer including the phosphorescent material and other organic layers. However, even when the organic layer has the 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 includes 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 another organic layer, 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 material (hereinafter also referred to as a host compound) of the light emitting layer.

The compound represented by the above general formula (1) may be contained in any organic layer between the cathode and the anode of the organic electroluminescence device.

Examples of the organic layer that may contain the compound represented by the general formula (1) include a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, an exciton blocking layer, a charge blocking layer (a hole blocking layer, And it is preferably a light emitting layer, an exciton block layer, a charge blocking layer, an electron transporting layer, or an electron injecting layer, more preferably a light emitting layer, an exciton block layer, a charge blocking layer, or an electron transporting layer, Is a light emitting layer, a hole blocking layer, and an electron blocking layer, more preferably a light emitting layer or a hole blocking layer, and even more preferably a light emitting layer.

When 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 95 mass%, and more preferably 10 to 95 mass% % Is more preferable.

The maximum emission wavelength of the light emitting material using the compound represented by the general formula (1) is preferably 400 to 700 nm, more preferably 500 to 700 nm, particularly preferably 500 to 650 nm, and most preferably 500 More preferably from 550 nm to 550 nm, and most preferably from 520 to 550 nm.

In addition, the electron transport layer or the hole blocking layer (more preferably, the hole blocking layer) is provided between the pair of electrodes, and the electron transporting layer or the hole blocking layer contains the compound represented by the general formula (1) desirable.

When the compound represented by the general formula (1) is contained in an organic layer other than the light emitting layer, the compound represented by the general formula (1) is preferably contained in an amount of 70 to 100 mass%, more preferably 85 to 100 mass%, based on the total mass of the organic layer.

These organic layers may be formed in plural layers, respectively, or in the case of forming a plurality of layers, they may be formed of the same material, or they 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 one 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 Or the like.

In the organic electroluminescent device of the present invention, it is preferable that the organic layer disposed between the pair of electrodes includes a layer formed by vapor deposition of a composition containing at least one compound represented by the above general formula (1).

(Light emitting layer)

The light emitting layer is a layer having a function of accepting holes from the anode, the hole injecting layer or the hole transporting layer, receiving electrons from the cathode, the electron injecting layer or the electron transporting layer, and providing a field for recombination of holes and electrons to emit light upon application of an electric field . 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 phosphorescent material.

The light-emitting layer in the organic electroluminescent device of the present invention may be composed of only the light-emitting material, or may be a mixed layer of the host material and the light-emitting material. The kind of the light emitting material may be one kind or two kinds or more. The host material is preferably a charge transporting material. The host material may be one species or two or more species. For example, the host material may be a mixture of an electron transporting host material and a hole transporting host material. The light emitting layer may include 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 include a different material for each layer. In the case of 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 usually preferably from 2 nm to 500 nm, more preferably from 3 nm to 200 nm from the viewpoint of external quantum efficiency, and more preferably from 5 nm to 100 nm 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; Herein, 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. 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, and most preferably 1% or less of the total amount of light emitted from the entire device. % Or less.

Hereinafter, the light emitting material and other host materials other than the compound represented by the general formula (1) will be described as the material of the light emitting layer 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.

(Luminescent material)

As the light emitting material in the present invention, a phosphorescent light emitting material, a fluorescent light emitting material, or the like can be used.

The light emitting layer in the present invention may contain two or more kinds of light emitting materials in order to improve the color purity or to extend the light emitting wavelength region. At least one of the light emitting materials is preferably a phosphorescent material.

In the present invention, in addition to at least one phosphorescent material contained in the luminescent layer, a phosphorescent material that is different from the phosphorescent material contained in the luminescent layer or the luminescent material may be used as the luminescent material.

The fluorescent material and the phosphorescent material are described in, for example, paragraphs [0100] to [0164] of JP-A No. 2008-270736 and paragraphs [0088] to [0090] of JP- , And the description of these publications can be applied to the present invention.

Examples of the phosphorescent material that can be used in the present invention include those described in US 6303238B1, US6097147, WO00 / 57676, WO00 / 70655, WO01 / 08230, WO01 / 39234A2, WO01 / 41512A1, WO02 / 02714A2, WO02 / 15645A1 , 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 , Japanese Unexamined Patent Publication No. 2003-123982, Japanese Unexamined Patent Publication No. 2002-170684, Japanese Unexamined Patent Application Publication No. 121257, Japanese Unexamined Patent Publication No. 2002-226495, Japanese Unexamined Patent Publication No. 2002-234894, Japanese Unexamined Patent Application Publication No. 2001-247859, Japanese Unexamined Patent Application Publication No. 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, WO07 / 095118, WO10 / 11 (Ir) complex, a platinum (Pt) complex, a Cu complex, a Re complex (Re complex), and the like can be given as examples of the phosphorescent compound described in Patent Documents 1 to 1175, WO10 / 027583 and WO10 / 028151. , W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Dy complex, and Ce complex. Particularly preferred are iridium (Ir) complexes, platinum (Pt) complexes or Re complexes. Among them, at least one of metal-carbon bonds, metal-nitrogen bonds, metal-oxygen bonds 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.

As the phosphorescent material contained in the light emitting layer in the present invention, an iridium (Ir) complex represented by the following general formula (E-1) or a platinum (Pt) complex represented by the following general formula (C- Is preferably used.

The iridium (Ir) complex represented by the general formula (E-1) will be described.

[Chemical Formula 15]

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

A ₁ is Z ¹ And a group of atoms forming a 5- or 6-membered heterocyclic ring together with the nitrogen atom.

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

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

n _E1 represents an integer of 1 to 3; n _E1 In the case of 2 or 3, there are two or three ligands including Z ¹ , Z ² , A ₁ and B ₁ , but two or three such ligands may be the same or different from each other.

n _E1 represents an integer of 1 to 3, preferably 2 or 3, and more preferably 3.

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 is Z ¹ And a group of atoms forming a 5- or 6-membered heterocyclic ring together with the 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, an oxazole ring, Triazole ring, oxadiazole ring, thiadiazole ring 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 imidazole ring, and most preferably a pyridine ring.

The 5 or 6-membered heterocyclic ring formed by A ₁ , Z ¹ and a nitrogen atom may have a substituent. As the substituent on the carbon atom, the following substituent group A can be used, and as the substituent on the nitrogen atom, the following substituent group B can be applied . 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 A"

(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, t-butyl, n- , 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, propyl, isopropyl, (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 20 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl and 3-pentenyl) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably a carbon number &lt; RTI ID = 0.0 &gt; 6 to 12, for example, phenyl, p-methylphenyl, naphthyl, anthryl, etc. (Preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino , An alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, e.g., methoxy, ethoxy, (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 20 carbon atoms), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, (Preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and more preferably 1 to 20 carbon atoms), and examples thereof include a phenyloxy group, a 1-naphthyloxy group and a 2-naphthyloxy group. Particularly preferably 1 to 12 carbon atoms, such as, for example, (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms), an aryloxy group (e.g., (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 20 carbon atoms), which may be substituted, (Preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 carbon atoms, and most preferably 7 carbon atoms), and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and more preferably 2 to 10 carbon atoms), an acyloxy group (preferably having 1 to 12 carbon atoms such as phenyloxycarbonyl) For example, acetoxy, benzoyl And the like), an acylamino 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 acetylamino, benzoylamino, etc.) , An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino) ), An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, 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 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino) (Preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl A carbamoyl 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 carbamoyl, methylcarbamoyl and the like) (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms), an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include methylthio, ethylthio and the like), arylthio groups Phenylthio and the like), Het (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolyl (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as mesyl (for example, , Tosyl, etc.), a sulfinyl 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 methanesulfinyl, benzenesulfinyl (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as, for example, ureide, methylureide, phenyl And the like), a phosphoric acid amide group Preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, and examples thereof include diethylphosphoric acid amide and phenylphosphoric acid amide) A halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxyl group, a sulfino group, a hydrazino group, A heterocyclic group (including a heteroaryl group, preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, A selenium atom and a tellurium atom, and specific examples thereof include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl , Quinolyl, fu Thienyl, thienyl, selenophenyl, telulophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group , A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, such as trimethylsilyl , Triphenylsilyl and the like), a silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, and particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, Triphenylsilyloxy, and the like), and a phosphoryl group (e.g., a diphenylphosphoryl group, a dimethylphosphoryl group, etc.). These substituents may be further substituted, and examples of the additional substituent include groups selected from the substituent group A described above. The substituent group substituted with a substituent may be further substituted, and examples of the additional substituent include groups selected from the substituent group A described above. The substituent group substituted with a substituent group may be further substituted, and examples of the substituent group include groups selected from the substituent group A described above.

"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, t-butyl, n- , 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, propyl, isopropyl, (Preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 20 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl and 3-pentenyl) (Preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably a carbon number &lt; RTI ID = 0.0 &gt; 6 to 12, for example, phenyl, p-methylphenyl, naphthyl, anthryl, etc. (Preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a halogen atom, a cyano group, a heterocyclic group (including a heteroaryl group, And examples thereof include a phosphorus atom, a silicon atom, a selenium atom and a tellurium atom. Specific examples include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, iso Wherein R is selected from the group consisting of oxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, telulophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, These substituents may be further substituted. As the additional substituent, there may be mentioned a group selected from the above-mentioned substituent group A. Examples of the substituent include a halogen atom, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, The substituent group substituted with a substituent may be further substituted, and examples of the additional substituent include groups selected from the substituent group A described above. The substituent group substituted with a substituent group may be further substituted, and examples of the substituent group include groups selected from the substituent group A described above.

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 selected.

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

The substituents may be connected to each other to form a condensed ring. Examples of the ring to be formed include benzene ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, imidazole ring, oxazole ring, thiazole ring, , Thiophene ring, furan ring and the like. The ring 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 is Z ² And a 5 or 6-membered ring containing a carbon atom. Examples of the 5 or 6-membered ring formed by B ₁ , Z ² and a carbon atom include benzene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, A thiazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring and a furan ring.

As the 5 or 6-membered ring formed by B ₁ , Z ² and a carbon atom in view of the stability of the complex, the control of the emission wavelength and the quantum yield of light emission, a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, , A thiophene ring, 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. As the substituent on the carbon atom, the substituent group A can be applied. The substituent group B on the nitrogen atom can be applied. 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 is suitably selected for control of the emission wavelength or the electric potential, but when it is long wavelength, the electron donating group and the aromatic ring group are preferable, and for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, a heteroaryl group and the like are 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.

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

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

(XY), there are various known ligands used for conventionally known metal complexes. For example, the ligand represented by the formula (XY) can be prepared by the method described in &quot; Photochemistry and Photophysics of Coordination Compounds, &quot; Springer-Verlag, H. Yersin, Organometallic Chemistry-Fundamentals and Applications- &quot;, Shokabosa Yamamoto Akio Publishing, 1982, and the like (for example, a halogen ligand (preferably a chlorine ligand), a nitrogen nitrogen heteroaryl ligand (for example, bipyridyl, Troline, etc.) and diketone ligands (e.g., acetyl acetone).

* Represents the coordination position with respect to iridium (Ir).

(X-Y) is preferably the following general formulas (I-1) to (I-13), but the present invention is not limited thereto.

[Chemical Formula 16]

* Represents the coordination position with respect to iridium (Ir) in the general formula (E-1). Rx, Ry and Rz each independently represent a hydrogen atom or a substituent. G represents C-R or a nitrogen atom. R represents a hydrogen atom or a substituent.

When Rx, Ry and Rz represent a substituent, examples of the substituent include substituents selected from the above-mentioned substituent group A. [ Preferably, each of Rx and Rz independently represents an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, a fluorine atom , A phenyl group which may be substituted, and most preferably a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group which may be substituted, An atom, or a methyl group. Rx, Ry, and Rz are chemically stable substituents, and do not affect the effect of the present invention, since these ligands are considered to be regions where electrons are not transported or carried by charge in the device.

R ^I1 to R ^{I7 in the} general formula (I-13) Is preferably a substituent selected from Substituent Group A and may further have Substituent A.

G represents C-R or a nitrogen atom. When R represents a substituent, examples of the substituent include a substituent selected from the above-mentioned substituent group A.

R ^I1 to R ^I7 and R in the case where G represents CR may be bonded to any two of them to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring may be substituted by cycloalkyl, aryl or heteroaryl , And the condensed 4- to 7-membered ring may further have a substituent.

The preferable range of R ^I1 to R ^I7 is the same as the preferable range of R ^T1 to R ^T7 in the general formula (E-3) to be described later.

G is preferably CR, and R is preferably a hydrogen atom or an aryl group, more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (e.g., a phenyl group, a tolyl group, A t-butyl group, etc.), particularly preferably a hydrogen atom or a phenyl group.

(I-1), (I-4) and (I-13), and particularly preferably (I-1) and (I-13). The complexes having these ligands can be synthesized in the same manner as the known synthesis examples by using the corresponding ligand precursors. For example, it can be synthesized in the same manner as described in International Publication No. 2009-073245, page 46.

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

[Chemical Formula 17]

In the general formula (E-2), A ^E1 to A ^E8 Each independently represent a nitrogen atom or CR &lt; ^{E &} gt ;.

R ^E Represents a hydrogen atom or a substituent.

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

n _E2 Represents an integer of 1 to 3.

A ^E1 to A ^E8 Each independently represent a nitrogen atom or CR &lt; ^{E &} gt ;. R ^E Represents a hydrogen atom or a substituent, R ^E Or may be connected to each other to form a loop. 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 , those exemplified as the above substituent group A can be applied.

A ^E1 to A ^E4 are preferably CR ^E , And A ^E1 to A ^E4 The CR in case of ^E, 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 as R ^E of A ^E3, than preferably a hydrogen atom, an alkyl group, An alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group or a fluorine atom, particularly preferably a hydrogen atom or a fluorine atom, and R ^E of A ^E1 , A ^E2 and A ^E4 is preferably a hydrogen atom, 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.

A ^E5 to A ^E8 , preferably CR ^E , And A ^E5 to A ^E8 In the case where the CR ^E, preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, dialkylamino group, diarylamino group, alkyloxy group, cyano and the group, or a fluorine atom as R ^E, 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 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. When the emission wavelength is shifted to the short wavelength side, A ^E6 Is preferably a nitrogen atom.

(XY), and n _E2 (XY) in the general formula (E-1), and n _E1 And the preferred scope is 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).

[Chemical Formula 18]

In the formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 An alkyl 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. 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. 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 atomic ring may further have a substituent. Of these, R ^T1 And R ^T7 , or R ^T5 And R ^T6 to form a benzene ring, and R ^T5 And R ^T6 to form a benzene ring.

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

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group which may be substituted include the substituent A 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, such as methyl group, ethyl group, an i-propyl group, a cyclohexyl group, and a t-butyl group, and a methyl group is particularly preferable.

The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group which may be substituted include the substituent A 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. Is particularly preferable.

The heteroaryl group represented by R ^T1 to R ^T7 and R 'is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 or 6 atoms, For example, a pyridyl group, a pyrazinyl 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 thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, An isothiazolyl group, a benzisothiazolyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazole group, A thiazolyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group , Dibenzo-thienyl group, and the like based degrees turned 7 flutes. Preferable examples thereof include a pyridyl group, a pyrimidinyl group, an imidazolyl group and a thienyl group, and more preferably a pyridyl group and a pyrimidinyl group.

R ^T1 to R ^T7 and R 'are preferably 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.

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. 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 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 R , It is particularly preferable that 0 to 2 are alkyl groups and all others are hydrogen atoms, and it is most preferable that 0 to 2 out of R ^T1 to R ^T7 and R 'are methyl groups and all others are hydrogen atoms Do.

n _E3 Is preferably 2 or 3. The kind of the ligand in the complex is preferably one or two kinds, more preferably two kinds.

(X-Y) is in agreement with (X-Y) in the general 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 19]

R ^T1 to R ^T4 , A, (XY) and n _{E4 in the} general formula (E-4) R ^T1 to R ^T4 , A, (XY) and n _{E3 in the} formula (E-3) And the preferred range is the same. R ₁ 'to R ₅ ' each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, 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. 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 atomic ring may further have a substituent.

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

Another preferred form of the compound represented by the above formula (E-3) is a compound represented by the following formula (E-5).

[Chemical Formula 20]

R ^T2 to R ^T6 , A, (XY) and n _{E5 in the} general formula (E-5) R ^T2 to R ^T6 , A, (XY) and n _{E3 in the} general formula (E-3) And the preferred range is the same. R ₆ 'to R ₈ ' each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, 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. 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 ^T5 , R ^T6 and R ₆ 'to R ₈ ' may combine with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl , The condensed 4- to 7-membered ring may further have a substituent.

A preferable range of R ₆ 'to R ₈ ' is the same as R ^T1 to R ^T7 and R 'in the formula (E-3). Particularly preferably, A is CR ', 0-2 of R ^T2 to R ^T6 , R', and R ₆ 'to R ₈ ' are an alkyl group or a phenyl group and all others are hydrogen atoms. ^It is more preferable that 0 to 2 out of ^T2 to R ^T6 , R ', and R ₆ ' to R ₈ 'are alkyl groups and all others are hydrogen atoms.

When a phosphorescent material represented by the general formula (E-4) or (E-5) is used, the compound represented by the general formula (1) is preferably contained in the luminescent layer or the hole blocking layer, More preferable.

Another preferred form of the compound represented by formula (E-1) is a case represented by the following formula (E-6).

[Chemical Formula 21]

In the general formula (E-6), R _1a to R _1k A cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, 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. 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.

R _1a to R _1k May be bonded to each other to form a condensed 4- to 7-membered ring. The condensed 4- to 7-membered ring may be cycloalkyl, aryl or heteroaryl, and the condensed 4- to 7-membered ring may further have a substituent You can have it.

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

n _E6 Represents an integer of 1 to 3.

In the general formula (E-6), preferred ranges of R _1a to R _1k are the same as those in R ^T1 to R ^T7 and R 'in the general formula (E-3). It is particularly preferable that 0 to 2 of R _1a to R _1k are an alkyl group or a phenyl group and all others are hydrogen atoms. Of the groups represented by R _1a to R _1k , 0 to 2 are alkyl groups and all the others are hydrogen atoms. desirable.

R _1j And R _1k Are bonded together to form a single bond.

(XY) and n _E6 are the same as those in (XY) and n _{E3 in the} general formula (E-3).

A more preferable form of the compound represented by the formula (E-6) is a case represented by the following formula (E-7).

[Chemical Formula 22]

In the general formula (E-7), R _1a to R _1i A cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, 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. 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.

R _1a to R _1k , Any two of them may combine with each other to form a condensed 4- to 7-membered ring. The condensed 4- to 7-membered ring may be a cycloalkyl group, an aryl group or a heteroaryl group, and the condensed 4- to 7-membered ring may be further And may have a substituent.

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

n _E7 Represents an integer of 1 to 3.

General formula (E-7) wherein the definition of R _1a ~ R _1i or the preferred range in the formula _{(E-6) R 1a ~} R 1i . It is particularly preferable that 0 to 2 of R _1a to R _1i are an alkyl group or an aryl group, and all others are hydrogen atoms. (XY) and n _E7 are defined as (XY) in the formula (E-3), and n _E3 .

When a phosphorescence emitting material represented by the general formula (E-6) or (E-7) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the hole blocking layer.

One preferred form of the compound represented by the above general formula (E-3) is a compound represented by the following general formula (E-8).

(23)

R ^T1 to R ^{T7 in the} general formula (E-8) Are synonymous with those in the general formula (E-3), and the preferable range thereof is also the same. R ^I1 1 to R ^I7 and G are the same as those in the ligand (l-13), and the preferable range is also the same. R 'represents a hydrogen atom or a substituent selected from Substituent Group A. R 'is preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, an aryl group or a heteroaryl group, more preferably a hydrogen atom, A fluorine atom or an aryl group, more preferably a hydrogen atom. n _E8 Represents an integer of 1 to 3, preferably 2 or 1.

One preferred form of the compound represented by the above general formula (E-3) is a compound represented by the following general formula (E-9).

&Lt; EMI ID =

R ^T1 , R ^T3 to R ^{T7 in the} general formula (E-9) Are synonymous with those in the general formula (E-3), and the preferable range thereof is also the same. R ^I1 to R ^I7 and G are synonymous with those in the ligand (l-13), and the preferable range thereof is also the same. R 'represents a hydrogen atom or a substituent selected from Substituent Group A. R 'is preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, an aryl group or a heteroaryl group, more preferably a hydrogen atom, A fluorine atom or an aryl group, more preferably a hydrogen atom. n _E9 Represents an integer of 1 to 3, preferably 2 or 1. X represents an oxygen atom or a sulfur atom.

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

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The compound exemplified as the compound represented by the general formula (E-1) can be synthesized by the method described in JP-A-2009-99783, or by various methods described in U.S. Patent No. 7279232. [ 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 compound represented by the general formula (E-1) is preferably contained in the light-emitting layer, but its use is not limited, and may be contained in any layer in the organic layer.

The compound represented by the general formula (E-1) in the light-emitting layer is 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- More preferably 50% by mass, more preferably 2% by mass to 40% by mass, and still more preferably 5% by mass to 20% by mass.

It is particularly preferable in the present invention to use a compound represented by any one of formulas (1) and (2) and a compound represented by any one of formulas (E-1) to (E-9)

A platinum (Pt) complex which can be used as a phosphorescent material is preferably a platinum (Pt) complex represented by the following general formula (C-1).

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(Wherein Q ¹ , Q ² , Q ³ and Q ⁴ Each independently represent a ligand which is coordinated to platinum (Pt). L ¹ , L ² and L ³ Each independently represent a single bond or a divalent linking group.

The general formula (C-1) will be described. Q ¹ , Q ² , Q ³ and Q ⁴ Each independently represent a ligand which is coordinated to platinum (Pt). At this time, Q ¹ , Q ² , Q ³ and Q ⁴ And platinum (Pt) may be any of covalent bonding, ionic bonding, coordination bonding, and the like. Q ¹ , Q ² , Q ³ and Q ⁴ Q ¹ , Q ² , Q ^3, and Q ⁴ are preferably a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a phosphorus atom as the atom bonding to the platinum (Pt) At least one of the atoms bonding to the platinum (Pt) in the platinum (Pt) is preferably a carbon atom, more preferably two carbon atoms, and particularly preferably two carbon atoms and two nitrogen atoms.

Q ¹ , Q ² , Q ³ and Q ⁴ bonded to platinum (Pt) by a carbon atom may be an anionic ligand or a neutral ligand. As an anionic ligand, a vinyl ligand, an aromatic hydrocarbon ring ligand (for example, benzene A thiophene ligand, a pyridine ligand, a pyrazine ligand, a pyrimidine ligand, a pyridazine ligand, a triazine ligand, a thiazole ligand, a thiazole ligand, a thiophene ligand, Pyrrole ligands, imidazole ligands, pyrazole ligands, triazole ligands, and cyclic rings containing them (e.g., quinoline ligands, benzothiazole ligands, etc.)). The neutral ligand is a carbenic ligand.

Q^One, Q², Q³ And Q⁴May have a substituent. As the substituent, those exemplified as the above substituent group A can be appropriately applied. The substituents may be connected to each other (Q³ And Q⁴ (Pt) complex of the cyclic quadrivalent ligand.

The group represented by Q ¹ , Q ² , Q ³ and Q ⁴ is preferably an aromatic hydrocarbon ring ligand which binds to platinum (Pt) as a carbon atom, an aromatic heterocyclic ligand which binds to platinum (Pt) An alkoxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand, and a silyloxy ligand, more preferably an aromatic heteroaryl ligand bonded to platinum (Pt) by a carbon atom, An aromatic heterocyclic ligand which binds to platinum (Pt) by a carbon atom, a nitrogen-containing aromatic heterocyclic ligand which binds to platinum (Pt) by a nitrogen atom, an acyloxy ligand, and an aryloxy ligand, more preferably a platinum An aromatic hydrocarbon ring ligand which binds to platinum (Pt), an aromatic hetero ring which binds to platinum (Pt) Ligand, also bonded to the nitrogen atom of platinum (Pt) aromatic heterocyclic nitrogen ligand, an acyloxy ligand.

L ¹ , L ² and L ³ Represents a single bond or a divalent linking group. Examples of the divalent linking group represented by L ¹ , L ² and L ³ include an alkylene group (methylene, ethylene, propylene), an arylene group (phenylene, naphthalenediyl), a heteroarylene group (pyridinediyl, (-NR-) (phenylimino group, etc.), an oxy group (-O-), a thio group (-S-), a phosphinoid group (-PR-) (phenylphosphinylidene group etc.), a silylene group (-SiRR '-) (dimethyl silylene group, diphenyl silylene group, etc.), or a combination thereof. Here, examples of R and R 'include, independently of each other, an alkyl group, an aryl group and the like. These linking groups may further have a substituent.

As L ¹ , L ² and L ³ , a monovalent bond, an alkylene group, an arylene group, a heteroarylene group, an imino group, an oxy group, a thio group and a silylene group are preferable as L ¹ , L ² and L ³ from the viewpoints of the stability of the complex and the yield of light- More preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, more preferably a single bond, an alkylene group, an arylene group or an imino group, More preferably a single bond, a dimethylmethylene group, a diethylmethylene group, a diisobutylmethylene group, a dibenzylmethylene group, an ethylmethylmethylene group, a methylpropylmethylene group, a isobutylmethylmethylene group Group, a diphenylmethylene group, a methylphenylmethylene group, a cyclohexanediyl group, a cyclopentanediyl group, a fluorenediyl group, and a fluoromethylmethylene group.

L ¹ is particularly preferably a dimethylmethylene group, a diphenylmethylene group or a cyclohexanediyl group, and most preferably a dimethylmethylene group.

L ² and L ³ are most preferably a single bond.

Among the platinum (Pt) complexes represented by the general formula (C-1), platinum (Pt) complexes represented by the following general formula (C-2) are more preferable.

[Chemical Formula 29]

(In the formulas, L ²¹ represents a single bond or a divalent linking group. A ^21, A ²² represents a carbon or nitrogen atom independently. Z ^21, Z ²² Each independently represent a nitrogen-containing aromatic heterocyclic ring. Z ²³ , Z ²⁴ Each independently represent a benzene ring or an aromatic heterocyclic ring.

The general formula (C-2) will be described. L &lt; ²¹ &gt; represents L ^&lt; 1 &gt; in formula (C-1) And the preferred scope is the same.

A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. At least one of A ²¹ and A ²² is preferably a carbon atom, and all of A ²¹ and A ²² are carbon atoms from the viewpoints of the stability of the complex and the yield of light emission of the complex.

Z ²¹ , Z ²² Each independently represent a nitrogen-containing aromatic heterocyclic ring. Examples of the nitrogen-containing heteroaromatic ring represented by Z ²¹ and Z ²² include pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole A thiadiazole ring, and the like. The ring represented by Z ²¹ and Z ²² is preferably a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole ring in view of the stability of the complex, the control of the emission wavelength, and the quantum yield of light emission. More preferably, An imidazole ring and a pyrazole ring, more preferably a pyridine ring and a pyrazole ring, and particularly preferably a pyridine ring.

Z ²³ , Z ²⁴ Each independently represent a benzene ring or an aromatic heterocyclic ring. Examples of the nitrogen-containing heteroaromatic ring represented by Z ²³ and Z ²⁴ include a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, A ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, a furan ring, and the like. The ring represented by Z ²³ and Z ²⁴ is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, or a thiophene ring in view of stability of a complex, control of an emission wavelength, Preferably a benzene ring, a pyridine ring or a pyrazole ring, more preferably a benzene ring or a pyridine ring.

Among the platinum (Pt) complexes represented by the general formula (C-2), one more preferred embodiment is a platinum (Pt) complex represented by the following general formula (C-4).

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(In the formula (C-4), A ⁴⁰¹ to A ⁴¹⁴ each independently represent a CR or a nitrogen atom, R represents a hydrogen atom or a substituent, and L ⁴¹ represents a single bond or a divalent linking group.

The general formula (C-4) will be described.

A ⁴⁰¹ to A ⁴¹⁴ each independently represent a CR or a nitrogen atom. R represents a hydrogen atom or a substituent.

As the substituent represented by R, those exemplified as the substituent group A can be applied.

A ⁴⁰¹ to A ⁴⁰⁶ are preferably CR and R may be connected to each other to form a ring. When A ⁴⁰¹ to A ⁴⁰⁶ are CR, R of A ⁴⁰² and A ⁴⁰⁵ 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, An amino group, an alkoxy group, an aryloxy group or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. The R of A ⁴⁰¹ , A ⁴⁰³ , A ⁴⁰⁴ and A ⁴⁰⁶ 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 alkoxy group, an aryloxy group, a fluorine atom, and particularly preferably a hydrogen atom.

L ⁴¹ is a group represented by L ¹ And the preferred scope is the same.

As A ⁴⁰⁷ to A ⁴¹⁴ , the number of N (nitrogen atom) is preferably 0 to 2, more preferably 0 to 1, in each of A ⁴⁰⁷ to A ⁴¹⁰ and A ⁴¹¹ to A ⁴¹⁴ . When shifting the emission wavelength of the short wavelength side, A ⁴⁰⁸ and A ⁴¹² of which is preferably a nitrogen atom, the A ⁴⁰⁸ and A ⁴¹² are both more preferably a nitrogen atom.

Among the platinum (Pt) complexes represented by the general formula (C-2), one of the more preferable embodiments is a platinum (Pt) complex represented by the following general formula (C-5).

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(In the general formula (C-5), A ⁵⁰¹ to A ⁵¹² each independently represent a CR or a nitrogen atom, R represents a hydrogen atom or a substituent, and L ⁵¹ represents a single bond or a divalent linking group.

The general formula (C-5) will be described. A ⁵⁰¹ to A ⁵⁰⁶ and L ⁵¹ are A ⁴⁰¹ to A ⁴⁰⁶ and L ^{41 in the} above general formula (C-4) And the preferred range is the same.

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² , and each independently represent a CR or nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied.

Among other platinum (Pt) complexes represented by the general formula (C-1), another preferred embodiment is a platinum (Pt) complex represented by the following general formula (C-6).

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(Wherein L ⁶¹ represents a single bond or a divalent linking group, A ⁶¹ independently represents a carbon atom or a nitrogen atom, Z ⁶¹ and Z ⁶² Each independently represent a nitrogen-containing aromatic heterocyclic ring. Z ⁶³ Each independently represent a benzene ring or an aromatic heterocycle. Y is an anionic non-coordinative ligand which binds to platinum (Pt).)

The general formula (C-6) will be described. L &lt; ⁶¹ &gt; is a group represented by L &lt; ^{1 &gt;} And the preferred scope is the same.

A ⁶¹ represents a carbon atom or a nitrogen atom. From the viewpoints of the stability of the complex and the quantum yield of light emission of the complex, A ⁶¹ is preferably a carbon atom.

Z ⁶¹ , Z ⁶² Are respectively represented by Z ²¹ and Z ^{22 in the} above general formula (C-2) And the preferred scope is the same. Z ⁶³ (Z- ²³ ) in the above general formula (C-2) And the preferred scope is the same.

Y is an anionic non-coordinative ligand which binds to platinum (Pt). The non-recrystallized ligand means that the atom bonding to the platinum (Pt) does not form a ring in the ligand state. The atom bonded to platinum (Pt) in Y is preferably a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, more preferably a nitrogen atom or an oxygen atom, and most preferably an oxygen atom.

As Y bonded to platinum (Pt) by a carbon atom, a vinyl ligand can be mentioned. Examples of Y bonded to platinum (Pt) by a nitrogen atom include amino ligands and imino ligands. Examples of Y bonded to platinum (Pt) as an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, a phosphoric acid ligand, and a sulfonic acid ligand. Examples of Y bonded to platinum (Pt) by a sulfur atom include alkylmercapto ligands, arylmercapto ligands, heteroarylmercapto ligands, and thiocarboxylic acid ligands.

The ligand represented by Y may have a substituent. As the substituent, those exemplified as the above substituent group A can be appropriately applied. The substituents may be connected to each other.

The ligand represented by Y is preferably a ligand which binds to platinum (Pt) as an oxygen atom, more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy ligand, or a silyloxy ligand, Acyloxy ligand.

Among the platinum (Pt) complexes represented by the general formula (C-6), one of the more preferred embodiments is a platinum (Pt) complex represented by the following general formula (C-7).

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(In the formula, A ⁷⁰¹ ~ A ⁷¹⁰ is, each independently, represents a CR or the nitrogen atom. R represents a hydrogen atom or a substituent. L ⁷¹ represents a single bond or a divalent connecting group. Y is a platinum (Pt) It is an anionic non-coordinative ligand that binds.)

The general formula (C-7) will be described. L ⁶¹ L ⁷¹ in the above general formula (C-6) And the preferred scope is the same. A ⁷⁰¹ to A ⁷¹⁰ are synonymous with A ⁴⁰¹ to A ⁴¹⁰ in the general formula (C-4), and preferable ranges are also the same. Y agrees with Y in the formula (C-6), and the preferable range thereof is also the same.

Specific examples of the platinum (Pt) complex represented by the general formula (C-1) include the compounds represented by the formulas [0143] to [0152], [0157] to [0158], [0162] to [0168] of JP-A No. 2005-310733 , Compounds described in [0065] to [0083] of JP-A No. 2006-256999, compounds described in [0065] to [0090] of JP-A No. 2006-93542, compounds disclosed in JP-A No. 2007-73891 The compounds described in [0063] to [0071], the compounds described in JP-A 2007-324309 [0079] to [0083], the compounds described in JP-A No. 2006-93542 [0065] to [0090] Compounds described in [0055] to [0071] of JP-A No. 2007-96255 and compounds [0043] to [0046] of JP-A No. 2006-313796 can be exemplified. In addition, platinum (Pt) .

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Platinum (Pt) complex compounds represented by the general formula (C-1) can be prepared, for example, in Journal of Organic Chemistry 53, 786, (1988), G. R. Newkome et al. , Method 790, method described in left column, lines 18 to 38, method 790, method described in right column 19 to 30, and combinations thereof, Chemische Berichte 113, 2749 (1980), H. Lexy et al., Page 2752, lines 26 to 35, and the like.

For example, the ligand or its dissociation product and a metal compound are dissolved in a solvent (for example, a halogen-based solvent, an alcohol-based solvent, an ether-based solvent, an ester-based solvent, a ketone-based solvent, a nitrile- (Various inorganic and organic bases such as sodium methoxide, t-butoxy potassium and the like) in the presence of a base, in the presence of a solvent, in the presence of a solvent, in a solvent, , Triethylamine, potassium carbonate, etc.), or in the presence of a base, at room temperature or below, or by heating (a method of heating by microwave in addition to ordinary heating is also effective).

The content of the compound represented by the general formula (C-1) in the light emitting layer of the organic electroluminescence of the present invention is preferably from 1 to 30 mass%, more preferably from 3 to 25 mass% More preferably 20% by mass.

The kind of the fluorescent light-emitting material is not particularly limited, and examples thereof include benzooxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin , Pyran, pyranone, oxadiazole, aldazine, pyrazine, cyclopentadiene, bisstyryl anthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, condensed polycyclic aromatic Metal complexes of 8-quinolinol, various metal complexes represented by pyromethene complexes or rare earth complexes, metal complexes such as pyromethene complexes and rare earth complexes, Polymer compounds such as polythiophene, polyphenylene and polyphenylene vinylene, organic silanes, and derivatives thereof.

Specific examples of the fluorescent light-emitting material are shown below, but the present invention is not limited thereto.

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(38)

[Chemical Formula 39]

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(41)

(42)

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The content of the fluorescent light-emitting material in the light-emitting layer of the organic electroluminescence device of the present invention is preferably 1 to 30 mass%, more preferably 1 to 20 mass%, and more preferably 1 to 10 mass% desirable.

In the present invention, the maximum emission wavelength of the light-emitting material is preferably 400 to 700 nm, more preferably 500 to 700 nm, and most preferably 520 to 700 nm, in view of prevention of quenching with the compound represented by the general formula (1) More preferably 650 nm, and most preferably 520 to 550 nm.

The maximum emission wavelength of the phosphorescent material represented by the general formula (E-3) is in the range of about 500 to 550 nm when no ring is formed in a plurality of R ^T1 to R ^T7 and R ' -4) or (E-5) is in the range of approximately 550 to 650 nm.

The thickness of the light-emitting layer is not particularly limited, but is usually preferably from 2 nm to 500 nm, more preferably from 5 nm to 200 nm from the viewpoint of external quantum efficiency, and more preferably from 10 nm to 100 nm More preferable.

The light-emitting layer in the organic electroluminescence device of the present invention may be composed of only the light-emitting material, or may be a mixed layer of the host material and the light-emitting material. The kind of the light emitting material may be one kind or two kinds or more. The host material is preferably a charge transporting material. The host material may be one species or two or more species. For example, the host material may be a mixture of a host material of an electron transporting property and a host material of a hole transporting property. The light emitting layer may contain a material which 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 include 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.

(Host material)

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. 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, and most preferably 1% or less of the total amount of light emitted from the entire device. % Or less.

As the host material, a compound represented by the general formula (1) can be used.

Other host materials that can be used in the organic electroluminescence device of the present invention include, for example, the following compounds.

And examples include pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran , Polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, arylamine, amino substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compound, styrylamine compound (Anthracene, pyrene, fluorene, naphthalene, phenanthrene, triphenylene, etc.), polysilane compounds, poly (N-vinylcarbazole), aniline-based copolymers, thiophene oligomers , An electrically conductive polymer oligomer such as polythiophene, an organic silane, a carbon film, an organic solvent such as pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazole, fluorenone, anthraquinodimethane, , Diphenylquinone, thiophene A heterocyclic tetracarboxylic acid anhydride such as naphthalene perylene or the like, a metal complex of a phthalocyanine or an 8-quinolinol derivative or a metal phthalocyanine such as metal phthalocyanine, And various metal complexes and their derivatives (which may have a substituent or an axial ring) typified by metal complexes having benzooxazole or benzothiazole as a ligand.

Of these, carbazole, dibenzothiophene, dibenzofuran, arylamine, cyclic aromatic hydrocarbon compounds and metal complexes are particularly preferable.

In the light emitting layer in the organic electroluminescent device of the present invention, the host material that can be used in combination is a hole transporting host material or an electron transporting host material.

In the light emitting layer, the triplet minimum excitation energy (T ₁ Energy) of the phosphorescent material is lower than the T ₁ Is higher than energy in terms of color purity, luminous efficiency and drive durability. T ₁ of the host material Is preferably larger than T ₁ of the phosphorescent material by 0.1 eV or more, more preferably 0.2 eV or more, and more preferably 0.3 eV or more.

T ₁ in the film state of the host material The T ₁ of the phosphorescent material , The light emission is quenched, so that the host material has a larger T ₁ . The T ₁ of the host material Is smaller than that of the phosphorescent light emitting material, reverse transfer of energy from the phosphorescent material to the host material takes place in some cases when the T ₁ difference is small, which causes efficiency reduction and durability deterioration. Therefore, T ₁ A host material having a sufficiently large chemical stability and a high carrier injection / transportation property is required.

The content of the host compound in the light emitting layer of the organic electroluminescence device of the present invention is not particularly limited but is preferably 15% by mass or more to 95% by mass or more with respect to the total mass of the compound forming the light emitting layer, By mass or less. When the light emitting layer contains a plurality of kinds of host compounds including a compound represented by the general formula (1), the compound represented by the general formula (1) is preferably 50 mass% or more and 99 mass% or less in the total host compounds.

(Other layers)

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

Other organic layers 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 as follows, 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 injection layer, a hole transporting layer, and an electron blocking layer from the anode side.

The organic electroluminescent device of the present invention preferably comprises at least one organic layer (B) 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 electroluminescence device of the present invention is the mode described in Fig. 1, in which the hole injection layer 4, the hole transport layer 5, (6), a hole blocking layer (7) and an electron transport layer (8) are stacked 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 accepting holes from the anode or the anode side and transporting them to the cathode side.

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

The hole injection layer preferably contains an electron-accepting dopant. By including an electron-accepting dopant in the hole injecting 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 electrons can be extracted from the material to be doped to generate radical cation, and examples thereof include tetracyanoquinodimethane (TCNQ), tetrafluoro (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 relative to the total mass of the compound forming the hole-injecting layer, 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.

As examples of the organic compound constituting the electron blocking layer, those exemplified as the above-mentioned hole transporting materials can be applied.

The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and even more preferably 5 nm to 50 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.

The material used for the electronic block layer is preferably a material having a T ₁ Is higher than energy in terms of color purity, luminous efficiency and drive durability. In the film state of the material used for the electronic block layer, T ₁ The T ₁ of the phosphorescent material More preferably at least 0.1 eV, more preferably at least 0.2 eV, and even more preferably at least 0.3 eV.

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

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

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

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

As the electron transporting material, the 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, imidazole derivatives , A benzoimidazole derivative, an imidazopyridine derivative, a fluorenone derivative, an anthraquinodimethane derivative, an anthrone derivative, a diphenylquinone derivative, a thiopyran oxide derivative, a carbodiimide derivative, a fluorenylidene methane derivative, Quinolinol derivatives, metal complexes of 8-quinolinol derivatives, metal complexes of metal phthalocyanine, benzooxazole and benzothiazole as ligands, and derivatives thereof, Various metal complexes, organosilane derivatives represented by siloxane, naphthalene, anthracene, phenanthrene , Triphenylene, preferably selected from chukhwan hydrocarbon compounds such as pyrene, and more preferably from pyridine derivatives, benzimidazole derivatives, already one of the imidazo pyridine derivatives, metal complexes, chukhwan hydrocarbon compound.

The thickness of the electron injection layer and the electron transporting 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 transport 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 donating dopant may be any organic material or inorganic material as long as it is capable of imparting electrons to the material to be doped and generating radical anions. Examples of the electron donating dopant include tetrathiafulvalene (TTF), tetrathia Dihydroimidazole compounds such as naphthacene (TTT) and bis- [1,3diethyl-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, and 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.

T ₁ in the film state of the organic compound constituting the hole blocking layer Energy, in order not to prevent the energy transfer of excitons generated in the light-emitting layer and lowering the luminous efficiency, the light emitting material T ₁ Higher than energy.

As an example of 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.

The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and still more preferably 5 nm to 50 nm.

The hole blocking layer may be 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 compositions.

The material used for the hole blocking layer is preferably the same as T ₁ Is higher than energy in terms of color purity, luminous efficiency and drive durability. T ₁ in the film state of the material used for the hole blocking layer The T ₁ of the phosphorescent material More preferably at least 0.1 eV, more preferably at least 0.2 eV, and even more preferably at least 0.3 eV.

(B-3) A material which is 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 which is 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) P-1) and a compound represented by the following general formula (O-1).

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

The organic electroluminescent device of the present invention preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (O-1) In view of the efficiency and the driving voltage. Hereinafter, general formula (O-1) will be described.

(44)

(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 May be the same or different. L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring or a heteroaryl ring. and 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) And may have a substituent selected. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. As the preferable substituent in the case where the aryl group of R ^O1 has a substituent, an alkyl group, an aryl group or a cyano group can be exemplified, and an alkyl group or an aryl group is more preferable, and an aryl group is more preferable. 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 selected from Substituent Group A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, more preferably an unsubstituted phenyl group or 2-phenyl Phenyl group.

A ^O1 ~ 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. A ^O1 ~ A ^O4 both CR ^A Or A ^O1 Is a nitrogen atom, A ^O2 to A ^O4 are CR ^A , And A ^O1 Is a nitrogen atom, and A ^O2 to A ^O4 The CR ^A , More preferably A ^O1 Is a nitrogen atom, and A ^O2 to A ^O4 The CR ^A And, R ^A Are all hydrogen atoms.

R ^A Represents a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms) or a heteroaryl group (preferably having 4 to 12 carbon atoms) And may have a substituent selected. The plurality of 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 a substituent selected from the above-mentioned substituent group A, 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.

[Chemical Formula 45]

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 device efficiency and is most preferably 2 from the viewpoint of the durability of the device.

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

(46)

(In the general formula (O-2), R ^O1 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 ~ 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 May be the same or different.)

R ^O1 and A ^O1 to A ^O4 , R ^O1 and A ^O1 to A ^{O4 in} the general formula (O-1) And their preferred ranges are the same.

R ⁰² ~ 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 may have a substituent selected from Substituent Group A. 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 general formula (O-1) is preferably a compound having a glass transition temperature (Tg) of 100 ° C. to 300 ° C. from the viewpoints of stability at high temperature storage and stable operation against heat generation during driving at high temperature More preferably 120 deg. C to 300 deg. C, further preferably 120 deg. C to 300 deg. C, still more preferably 140 deg. C to 300 deg.

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

(47)

(48)

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.

The compound represented by formula (O-1) is preferably contained in an amount of 70 to 100 mass%, more preferably 85 to 100 mass%, with respect to the total mass of the organic layer to be added.

It is preferable that the organic electroluminescent device of the present invention includes at least one organic layer between the light emitting layer and the cathode and that the organic layer contains at least one compound represented by the following general formula (P) Or a driving voltage. Hereinafter, the general formula (P) will be described.

(49)

(Of the general formula (P), R ^P Represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms) And may have a substituent. nP represents an integer of 1 to 10, R ^P They may be the same or different. And R ^P is a substituent represented by the following general formulas (P-1) to (P-3).

(50)

(R ^P1 to R ^P3 , R ' ^P1 to R' ^{P3 in the} general formulas (P-1) to (P-3) Each represent 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 may have a substituent. n ^P1 and n ^P2 Represents an integer of 0 to 4, and R ^P1 to R ^P3 , R ' ^P1 to R' ^P3 In a plurality of cases, they may be the same or different. L ^P1 to L ^P3 each represent any of a divalent linking group consisting of a single bond, an aryl ring or a heteroaryl ring. * Represents the bonding position of the anthracene ring of the general formula (P).)

Preferred substituents other than the substituents represented by (P-1) to (P-3) as R ^P are aryl groups, more preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, more preferably a naphthyl group to be.

R ^P1 to R ^P3 and R ' ^P1 to R' ^P3 are preferably an aryl group or a heteroaryl group, more preferably an aryl group, still more preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group And most preferably a phenyl group.

Each of L ^P1 to L ^P3 is preferably a divalent linking group consisting of a single bond or an aryl ring, more preferably a single bond, phenylene, biphenylene, terphenylene or naphthylene, more preferably Is a single bond, phenylene, or naphthylene.

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

(51)

(52)

The compound represented by the formula (P) can be synthesized by a method described in WO2003 / 060956, WO2004 / 080975, and the like. 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 (P) is preferably contained in the organic layer between the light emitting layer and the cathode, but more preferably contained in the layer adjacent to the cathode.

The compound represented by formula (P) is preferably contained in an amount of 70 to 100 mass%, more preferably 85 to 100 mass%, based on the total mass of the organic layer to be added.

<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 Patent Laid-Open 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 include an alternating current component if necessary) (usually 2 volts 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, 8-241047, 2784615, 5828429 and 6023308 can be applied .

The external quantum efficiency of the organic electroluminescent device of the present invention is preferably 7% or more, more preferably 10% or more, and further preferably 12% 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, by studying 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 emission, green emission, or blue emission. Among them, the organic electroluminescent device of the present invention preferably has an emission wavelength of 500 to 700 nm from the viewpoint of 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 the host material of the light emitting layer, the light emitting wavelength is preferably 500 to 700 nm, more preferably 500 to 550 nm , More preferably from 520 to 550 nm.

On the other hand, in the organic electroluminescent device of the present invention, when the compound represented by the general formula (1) is used as the charge transporting material of the hole blocking layer, the light emitting wavelength is preferably 400 to 700 nm, more preferably 450 to 600 nm, more preferably from 450 to 550 nm.

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

The organic electroluminescent device of the present invention can be suitably used for a display device, a display, a backlight, an electronic photograph, an illumination light source, a recording light source, an exposure light source, a reading light source, a mark, 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.

The light emitting device of the present invention is formed using the organic electroluminescent device.

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 stacking 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 cellular 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, Is emitted 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. Examples of the display device of the present invention include a display device such as a television, a personal computer, a cellular phone, and an electronic paper.

Example

Hereinafter, the present invention will be described in more detail with reference to examples. The materials, the amounts to be used, the ratios, the contents of the treatments, the processing procedures, and the like shown in the following examples can be appropriately changed as long as they do not depart from the gist of the present invention. Therefore, the scope of the present invention is not limited to the following specific examples.

1. Synthetic Example

The compound represented by the above general formula (1) can be synthesized by the method described in JP-A-2010-535806, or a combination of known reactions.

(Synthesis Example 1) Synthesis of Compound 1

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Bis (diphenylphosphino) ferrocene] palladium dichloride A mixture of 10.0 g (32.3 mmol) of 3-bromo-p-terphenyl, 12.3 g (48.5 mmol) of bis (pinacolato) diboron, 1.32 g (1.62 mmol) of the complex (1: 1) (PdCl ₂ (dppf)), 9.51 g (96.9 mmol) of potassium acetate and 170 ml of dimethylsulfoxide (DMSO) Lt; / RTI &gt; After the reaction solution was returned to room temperature, toluene and water were added to extract the organic layer. The organic layer was concentrated and purified by column chromatography (developing solvent: toluene / hexane (1: 1)) and recrystallized from toluene / ethanol (1: 2) to obtain 7.35 g (yield 64% ).

2.13 g (5.20 mmol) of 1-bromo-3,5-diiodobenzene, 58 mg (0.26 mmol) of palladium acetate, 273 mg (1.04 mmol) of triphenylphosphine, 2.20 g (20.8 mmol) of sodium carbonate, 32 ml of 1,2-dimethoxyethane (DME) and 16 ml of water were mixed and stirred for 12 hours under a nitrogen atmosphere. The reaction solution was returned to room temperature, and the precipitated solid was filtered. This solid was completely dissolved by heating in toluene. The black component was separated by filtration through a Celite filter, and then the solid precipitated at room temperature was filtered to obtain 2.12 g (66%) of the synthesis intermediate 2.

1.17 g (3.30 mmol) of 4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane, 1.84 g (3.00 mmol) 83 mg (0.090 mmol) of tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) and 148 mg (0.36 mmol) of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl ), 1.28 g (6.00 mmol) of potassium phosphate, 25 ml of toluene and 12.5 ml of water were mixed and heated under reflux in a nitrogen atmosphere for 5 hours. The reaction solution was returned to room temperature, and the precipitated solid was filtered. This solid was completely dissolved by heating with toluene, and the origin component was removed by silica gel column chromatography (developing solvent: toluene), followed by recrystallization with toluene, whereby 1.95 g of Compound 1 was obtained (yield: 85%).

NMR data of Compound 1

(Synthesis Example 2) Synthesis of Compound 4

(54)

A mixture of 4.18 g (11.0 mmol) of 4- (triphenylsilyl) phenylboronic acid, 12.5 g (44.0 mmol) of p-bromoiodobenzene, 74 mg (0.33 mmol) of palladium acetate, 346 mg (1.32 mmol) 2.33 g (22.0 mmol) of sodium carbonate, 54 ml of 1,2-dimethoxyethane (DME) and 27 ml of water were mixed, and the mixture was refluxed under nitrogen atmosphere for 3 hours. After the reaction solution was returned to room temperature, the organic layer was extracted. The organic layer was concentrated, and then the origin component was removed by silica gel column chromatography (developing solvent: toluene), and the residue was washed with hexane to give 4.00 g of synthetic intermediate 3 (74%).

Synthesis of intermediate Intermediate 3 was carried out in the same manner as in Example 1 except that 4.00 g (8.14 mmol) of bis (pinacolato) diboron and 3.10 g (12.2 mmol) of 1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane complex 334 mg (0.41 mmol) of PdCl ₂ (dppf), 1.84 g (18.7 mmol) of potassium acetate and 65 ml of dimethylsulfoxide (DMSO) were mixed and stirred at 70 ° C for 5 hours under a nitrogen atmosphere. After the reaction solution was returned to room temperature, toluene and water were added to extract the organic layer. The organic layer was concentrated and purified by silica gel column chromatography (developing solvent: toluene / hexane (2: 3)) and further washed with methanol to obtain 2.90 g (yield: 66%) of synthetic intermediate 4.

A mixture of 2.69 g (5.00 mmol) of the synthetic intermediate 4, 4.68 g (15.0 mmol) of 3,3'-dibromo-1,1'-biphenyl, 34 mg (0.15 mmol) of palladium acetate, 157 mg 0.60 mmol), sodium carbonate (1.06 g, 10.0 mmol), toluene (32 mL) and water (16 mL) were mixed and heated under reflux in a nitrogen atmosphere for 12 hours. The reaction solution was returned to room temperature, and the organic layer was extracted. The organic layer was concentrated and then purified by silica gel column chromatography (developing solvent: toluene / hexane (1: 2)). Further, the mixture was washed by dropwise washing with ethanol to obtain 1.70 g (yield: 53%) of synthetic intermediate 5.

974 mg (2.75 mmol) of 4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane and 1.61 g (2.50 mmol) 69 mg (0.075 mmol) of tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) and 123 mg (0.30 mmol) of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl ), Potassium phosphate (1.06 g, 5.00 mmol), toluene (20 ml) and water (10 ml) were mixed and heated under reflux in a nitrogen atmosphere for 6.5 hours. After the reaction solution was returned to room temperature, the organic layer was extracted. The organic layer was concentrated, and the origin component was removed by silica gel column chromatography (developing solvent: toluene). The original component was recrystallized from toluene / hexane (1: 1) and dropped with acetone dropwise to obtain 1.61 g of Compound 4 %).

NMR data of Compound 4

Compound 2, compound 3 and compounds 5 to 12 were also synthesized in accordance with the synthesis method of Compound 1 and Compound 4.

2. Device manufacturing and evaluation

All of the materials used in the manufacture of the device were subjected to sublimation purification, and it was confirmed by purity (absorption intensity area ratio at 254 nm) of 99.9% or more by high performance liquid chromatography (Toso TSKgel ODS-100Z).

(Example 1)

A glass substrate (surface resistance: 10 Ω / □) having an ITO film of 0.5 mm in thickness and 2.5 cm in width and length was placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol and subjected to UV-ozone treatment for 30 minutes . The following organic compound layers were sequentially deposited on this transparent anode (ITO film) by vacuum deposition.

Layer 1: HAT-CN: Film thickness 10 nm

Second layer: NPD: film thickness 30 nm

Layer 3: host material and GD-1 (weight ratio 90:10) described in Table 1: film thickness 30 nm

Layer 4: HBL material described in Table 1: film thickness 5 nm

Layer 5: Alq: film thickness 45 nm

0.1 nm of lithium fluoride and 100 nm of metal aluminum were deposited in this order on this to form a negative electrode.

The resulting laminate was placed in a glove box substituted with nitrogen gas without being brought into contact with the atmosphere and encapsulated with a glass encapsulating can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagasechiba Co., Ltd.) To 1-8 and comparative devices 1-1 to 1-3 were obtained. The light emitting portion has a square of 2 mm x 2 mm. Table 1 shows the results of evaluating these devices from the viewpoint of the relative efficiency and the maximum attained luminance after high-temperature storage in the following manner.

(a) Relative efficiency after storage at high temperature

A direct current voltage was applied to each element to emit light using a source major unit 2400 manufactured by Toyotecnica, and the luminance was measured using a luminance system BM-8 manufactured by Topcon Corporation. The emission spectrum and the emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these, the external quantum efficiency (eta) near the luminance of 1000 cd / m &lt; 2 &gt; was calculated by the luminance conversion method.

Each device was stored in a thermostatic chamber at 100 DEG C for 100 hours, and the efficiency (? ') Was measured in the same manner as before. The ratio (? '/?) Of these is used as an index of heat resistance. The larger this value is, the better.

(b) maximum reaching luminance

The applied voltage is increased while the luminance of each element is measured, and the maximum luminance is expressed as the relative luminance.

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 the compounds 1, 2, 4, 8, 9, 11 and 12 as the host compound of the light emitting layer, And that the maximum luminance was also high. It has also been found that the devices 1-6 to 1-8 using the compound represented by the general formula (1) in the host material of the light emitting layer and the hole blocking layer also have the highest maximum luminance.

On the other hand, Comparative Devices 1-1 to 1-3 were Comparative Compounds 1, 2 and 4 as the host compounds in the light emitting layer, respectively, and found that the relative efficiency after storage at high temperature was poor and the maximum luminance was also low.

The emission wavelength of the organic electroluminescent device manufactured in Example 1 was 522 to 527 nm.

(Example 2)

The device was manufactured in the same manner as in Example 1 except that the layer structure was changed to the following, and the same evaluation as in Example 1 was carried out.

First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm

Second layer: NPD: film thickness 5 nm

Layer 3: HT-1: film thickness 3 nm

Layer 4: H-1 and GD-2 (mass ratio 85: 15): film thickness 30 nm

Fifth layer: HBL material described in Table 2: film thickness 10 nm

Layer 6: ET-2: film thickness 20 nm

It can be seen from Table 2 that the organic electroluminescent devices of the respective examples using the compounds represented by the general formula (1) of the compounds 2, 9 and 10 as the material of the hole blocking layer all had good relative efficiency after high temperature storage, Was also high.

On the other hand, the comparative devices 2-1 and 2-2 were comparative compounds 2 and 3 as the materials of the hole blocking layer, respectively, and it was found that the relative efficiency after storage at high temperature was low and the maximum reachable luminance was low.

The emission wavelength of the organic electroluminescent device prepared in Example 2 was 503 to 507 nm.

(Example 3)

The device was fabricated in the same manner as in Example 1 except that the layer structure was changed to that shown below, and the same evaluation as in Example 1 was carried out.

Layer 1: CuPc: film thickness 10 nm

Second layer: NPD: film thickness 30 nm

Third layer: host material and RD-1 (weight ratio 95: 5) described in Table 3: film thickness 30 nm

Layer 4: ET-2: film thickness 5 nm

Layer 5: ET-3: film thickness 50 nm

It can be seen from Table 3 that the organic EL devices of the respective examples using the compounds represented by the general formula (1) of the compounds 1, 6, 7 and 9 as the host compound in the light emitting layer all exhibited good relative efficiency after storage at high temperature, And the luminance was also high.

On the other hand, the comparative devices 3-1 and 3-2 were Comparative Compounds 2 and 5 as the host material of the light-emitting layer, and it was found that the relative efficiency after storage at high temperature was low and the maximum arrival luminance was low.

In addition, the emission wavelength of the organic electroluminescent device manufactured in Example 3 was 618 to 622 nm.

(Example 4)

A device was manufactured in the same manner as in Example 1 except that the layer configuration was changed to the following, and the same evaluation as in Example 1 was carried out.

Layer 1: TCTA: film thickness 35 nm

Second layer: HT-2: film thickness 5 nm

Layer 3: BAlq and RD-2 (weight ratio 90: 10): film thickness 30 nm

Layer 4: HBL material described in Table 4: film thickness 5 nm

Layer 5: ET-4: Film thickness 45 nm

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 the compounds 3, 6 and 11 as the material of the hole blocking layer all had good relative efficiency after high temperature storage, Was also high.

On the other hand, the comparative elements 4-1 and 4-2 were Comparative Compounds 1 and 2 used as the material of the hole blocking layer, and it was found that the relative efficiency after storage at high temperature was low and the maximum reachable luminance was low.

The emission wavelength of the organic electroluminescent device manufactured in Example 4 was 628 to 631 nm.

(Example 5)

A device was manufactured in the same manner as in Example 1 except that the layer structure was changed to the following, and the same evaluation as in Example 1 was carried out.

Layer 1: HAT-CN: Film thickness 10 nm

Second layer: NPD: film thickness 115 nm

Layer 3: HT-3: film thickness 5 nm

Layer 4: H-2 and Firpic (weight ratio 90:10): film thickness 30 nm

Fifth layer: HBL material described in Table 5: film thickness 5 nm

Layer 6: ET-5: film thickness 25 nm

It can be seen from Table 5 that the organic electroluminescent devices of the respective Examples using the compounds represented by the general formula (1) of the compounds 1, 8 and 10 as the material of the hole blocking layer all had good relative efficiency after storage at high temperature, Was also high.

On the other hand, Comparative Devices 5-1 and 5-2 used Comparative Compounds 2 and 3 as materials of the hole blocking layer, and found that the relative efficiency after storage at high temperature was poor and the maximum arrival luminance was low.

The emission wavelength of the organic electroluminescent device manufactured in Example 5 was 472 to 476 nm.

(Example 6)

The device was fabricated in the same manner as in Example 1 except that the layer configuration was changed to that shown below, and the same evaluation as in Example 1 was carried out.

First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 120 nm

Second layer: NPD: film thickness 7 nm

Layer 3: HT-3: film thickness 3 nm

Layer 4: H-3 and BD-1 (weight ratio 85: 15): film thickness 30 nm

Fifth layer: HBL material described in Table 6: film thickness 5 nm

Layer 6: BAlq: film thickness 25 nm

It can be seen from Table 6 that the organic electroluminescent devices of the respective Examples using the compounds represented by the general formula (1) of the compounds 5, 10 and 12 as the material of the hole blocking layer are all excellent in relative efficiency after storage at high temperature, Was also high.

On the other hand, the comparative devices 6-1 and 6-2 were Comparative Compounds 2 and 3 used as the material of the hole blocking layer, and it was found that the relative efficiency after storage at high temperature was poor and the maximum arrival luminance was low.

The emission wavelength of the organic electroluminescent device manufactured in Example 6 was 457 to 460 nm.

(Example 7)

A device was manufactured in the same manner as in Example 1 except that the layer configuration was changed to the following, and the same evaluation as in Example 1 was carried out.

First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm

Second layer: NPD: film thickness 5 nm

Layer 3: HT-1: film thickness 3 nm

Layer 4: H-1 and GD-3 (weight ratio 90:10): film thickness 30 nm

Fifth layer: HBL material described in Table 7: film thickness 10 nm

Layer 6: ET-2: film thickness 20 nm

(Example 8)

A device was manufactured in the same manner as in Example 1 except that the layer configuration was changed to the following, and the same evaluation as in Example 1 was carried out.

First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm

Second layer: NPD: film thickness 5 nm

Layer 3: HT-1: film thickness 3 nm

Layer 4: H-1 and GD-4 (weight ratio 90: 10): film thickness 30 nm

Fifth layer: HBL material described in Table 8: film thickness 10 nm

Layer 6: ET-2: film thickness 20 nm

(Example 9)

A device was fabricated in the same manner as in Example 1 except that the layer structure was changed to the following, and evaluation was carried out in the same manner as in Example 1,

First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm

Second layer: NPD: film thickness 5 nm

Layer 3: HT-1: film thickness 3 nm

Layer 4: H-1 and GD-5 (weight ratio 90: 10): film thickness 30 nm

Fifth layer: HBL material described in Table 9: film thickness 10 nm

Layer 6: ET-2: film thickness 20 nm

It can be seen from Tables 7 to 9 that the organic electroluminescent devices of the respective embodiments using the compound of the present invention as the host compound of the light emitting layer all exhibited good relative efficiency after storage at high temperature and high maximum luminance.

On the other hand, it was found that the device using the comparative compound as the host compound had a low relative efficiency after storage at high temperature and a small maximum luminance.

(55)

(56)

(57)

2: substrate
3: anode
4: Hole injection layer
5: hole transport layer
6: light emitting layer
7: Hole block layer
8: Electron transport layer
9: cathode
10: Organic electroluminescent device
11: Organic layer
12: Protective layer
14: Adhesive layer
16: Encapsulation container
20: Light emitting device
30: light scattering member
31: transparent substrate
30A: light incidence surface
30B: light emitting surface
32: particulate
40: Lighting device

Claims (18)

A charge-transporting material characterized by comprising a compound represented by the following general formula (1).
[Chemical Formula 1]

(In the general formula (1), R ¹⁰¹ and R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI &gt; does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ and R ¹⁰² (In which the ring is a six-membered ring in which the ring atoms are constituted by carbon atoms or nitrogen atoms) in a total number of 5 or more. n ₁₀₁ Is an integer of 0 to 11, n ₁₀₂ Represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² May be the same or different. A ^A1 ~ A ^A9 Each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom. The method according to claim 1,
A charge transporting material characterized in that the compound represented by the general formula (1) is represented by the following general formula (2).
(2)

(In the general formula (2), R ¹¹¹ independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted by these groups or amino groups.) R ²³¹ to R ²³⁴ Each independently represent an alkyl group, a fluorine atom, a silyl group or an amino group. R ²³⁵ to R ²³⁸ Each independently represent an aryl group or a heteroaryl group. Provided that R ¹¹¹ and R ²³¹ to R ²³⁸ Lt; / RTI &gt; does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹¹¹ and R ²³¹ to R ²³⁸ (The aromatic ring is a six-membered ring in which the ring atom is composed of a carbon atom or a nitrogen atom) in a total number of 3 to 6. ₁₁₁ n represents an integer of 0 to 11, and y35 y33 y31 ~ ~ y37 are each independently an integer of 0 to 4, y34, and y38 represents an integer of 0-5. A plurality of R ¹¹¹ and R ²³¹ to R ²³⁸ May be the same or different. A ^B1 to A ^B17 Each independently represent CH (the hydrogen atom of CH may be substituted by R ²³¹ to R ²³⁸ ) or a nitrogen atom, and is a ring atom constituting an aromatic ring of a six-membered ring. 3. The method of claim 2,
In the above formula (2), A ^B3 Represents a CH, and the hydrogen atom of A ^B3 is the above-mentioned R ²³⁵ Wherein the charge transporting material is substituted by at least one of the following groups: 4. The method according to any one of claims 1 to 3,
In the above general formula (1), n ₁₀₁ Lt; 0 &gt; 5. The method according to any one of claims 1 to 4,
R ¹⁰¹ or R ^{102 in} the general formula (1) Is a substituent group comprising a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, or a cycloalkylene group or a silicon atom-linking group. 6. The method according to any one of claims 1 to 5,
Wherein the ring of all the monocyclic rings included in the general formula (1) is a six-membered ring of a carbon atom skeleton. 7. The method according to any one of claims 1 to 6,
Wherein the compound represented by the general formula (1) comprises only carbon atoms and hydrogen atoms. 8. The method according to any one of claims 1 to 7,
Wherein the compound represented by the general formula (1) has a molecular weight of 1,200 or less. 9. The method according to any one of claims 1 to 8,
Wherein the compound represented by the above general formula (1) is a partial structure in which four or more aromatic rings (whose ring is a six-membered ring in which ring atoms are composed of carbon atoms or nitrogen atoms) At least one &lt; RTI ID = 0.0 &gt;
Wherein the number of directional rings of the monolith continuously connected at the para position in the partial structure is 3 or less. A substrate;
A pair of electrodes arranged on the substrate and including an anode and a cathode,
An organic layer disposed between the electrodes,
Wherein the organic layer contains a phosphorescent light-emitting material and the charge transporting material according to any one of claims 1 to 9. 11. The method of claim 10,
Wherein the phosphorescent material is represented by the following general formula (E-1).
(3)

(In the general formula (E-1), Z ¹ and Z ² Each independently represent a carbon atom or a nitrogen atom. A ₁ is Z ¹ And a group of atoms forming a 5- or 6-membered heterocyclic ring together with the nitrogen atom. B ₁ is Z ² And a group of atoms forming a 5 or 6-membered ring together with the carbon atom. (XY) represents a monoanionic two-position ligand. n _E1 represents an integer of 1 to 3.) The method according to claim 10 or 11,
Wherein the phosphorescent material represented by the general formula (E-1) is represented by the following general formula (E-2).
[Chemical Formula 4]

(In the general formula (E-2), A ^E1 to A ^E8 Each independently represent a nitrogen atom or a carbon atom substituted with R &lt; ^{E &} gt ;. R ^E Represents a hydrogen atom or a substituent. (XY) represents a monoanionic two-position ligand. n _E2 Represents an integer of 1 to 3.) 13. The method according to any one of claims 10 to 12,
Wherein the phosphorescence emitting material represented by the general formula (E-1) has a maximum emission wavelength of 500 nm to 700 nm. 14. The method according to any one of claims 10 to 13,
Wherein the organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
Wherein the light-emitting layer contains the compound represented by the general formula (1). 15. The method according to any one of claims 10 to 14,
Wherein the organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
Wherein the other organic layer includes a hole blocking layer disposed between the light emitting layer and the cathode, and the hole blocking layer contains the compound represented by the general formula (1). 16. The method according to any one of claims 10 to 15,
Wherein the maximum emission wavelength is from 500 nm to 550 nm. A light emitting device, a display device or a lighting device, characterized by comprising the organic electroluminescent device according to any one of claims 10 to 16. A compound represented by the following general formula (1).
[Chemical Formula 5]

(In the general formula (1), R ¹⁰¹ and R ¹⁰² Each independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² Lt; / RTI &gt; does not include a cyclic aryl structure and a cyclic heteroaryl structure. R ¹⁰¹ and R ¹⁰² (In which the ring is a six-membered ring in which the ring atoms are constituted by carbon atoms or nitrogen atoms) in a total number of 5 or more. n ₁₀₁ is an integer of 0 to 11, n ₁₀₂ Represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² may be the same or different. A ^A1 ~ A ^A9 Each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.

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