JP2018200999A - Film, manufacturing method of film, organic light emitting element, lighting apparatus, and compound - Google Patents

Abstract

To provide an organic light emitting element which emits light in a long wavelength region with high luminous efficiency and has long driving lifetime.SOLUTION: There is provided an organic light emitting element including a compound represented by the general formula (1) and a compound represented by the general formula (2).SELECTED DRAWING: None

Description

  The present invention relates to a film using a combination of a compound in which two or more cyano groups and one or more carbazolyl groups are substituted on a benzene ring and a rubrene compound, and a method for producing the film. In addition, the present invention relates to an organic light-emitting element using a combination of these two types of compounds and a lighting device using the same. Further, it relates to a novel dicyanobenzene compound and a synthetic intermediate thereof.

Researches for increasing the light emission efficiency of organic light emitting devices such as organic electroluminescence devices (organic EL devices) are being actively conducted. In particular, various efforts have been made to increase the light emission efficiency by newly developing and combining electron transport materials, hole transport materials, light emitting materials, and the like constituting the organic electroluminescence element. Some of these studies focus on compounds that emit delayed fluorescence.
Delayed fluorescence is emitted when a compound that has been excited by energy donation undergoes reverse intersystem crossing from the excited triplet state to the excited singlet state and then returns to the ground state from the excited singlet state. This is fluorescence, which is observed after the fluorescence from the directly excited singlet state (normal fluorescence). When such a compound capable of emitting delayed fluorescence is used as a light-emitting material of an organic electroluminescence device, the energy of the excited triplet state, which has a high formation probability, is converted into fluorescence and can be effectively used for light emission, so that high light emission efficiency can be expected. become. For this reason, the development of compounds that emit delayed fluorescence has been actively promoted, and some proposals have been made for using such compounds as light emitting materials.
For example, in Patent Document 1, a compound in which two or more cyano groups and one or more carbazolyl groups are substituted on the benzene ring is a compound that can emit delayed fluorescence, such as 4CzIPN having the following structure. It is described. And when such a compound is used as light emitting materials, such as an organic electroluminescent element, it is described that luminous efficiency can be improved.

Japanese Patent No. 5366106

However, many organic light-emitting devices that use a co-evaporated film composed of the above compound and a host material as a light-emitting layer emit light in a relatively short wavelength region, although exhibiting high luminous efficiency. Therefore, there is a need for a technique for providing an organic light emitting device that emits light in a longer wavelength region while exhibiting high luminous efficiency.
Under these circumstances, the present inventors emitted light in a longer wavelength region and had high emission efficiency while using a compound in which two or more cyano groups and one or more carbazolyl groups were substituted on the benzene ring. In order to provide an organic light-emitting device having a longer driving life, an extensive study was conducted.

  As a result of diligent investigation, the present inventors have used a compound in which two or more cyano groups and one or more carbazolyl groups or the like are substituted on the benzene ring in combination with a specific rubrene compound in a longer wavelength region. It has been found that an organic light-emitting device that emits light, has high emission efficiency, and has a long driving life can be realized. The present invention has been proposed based on such knowledge and has the following configuration.

［一般式（１）において、Ｒ¹〜Ｒ⁵の少なくとも１つはシアノ基を表し、Ｒ¹〜Ｒ⁵の少なくとも１つは下記一般式（１１）で表される基を表し、残りのＲ¹〜Ｒ⁵は水素原子または置換基（ただしシアノ基と一般式（１１）で表される基は除く）を表す。］

［一般式（１１）において、Ｒ²¹〜Ｒ²⁸は、各々独立に水素原子または置換基を表す。ただし、下記＜Ａ＞か＜Ｂ＞の少なくとも一方を満たす。
＜Ａ＞ Ｒ²⁵およびＲ²⁶は一緒になって単結合を形成する。
＜Ｂ＞ Ｒ²⁷およびＲ²⁸は一緒になって置換もしくは無置換のベンゼン環を形成するのに必要な原子団を表す。］

［一般式（２）において、Ｒ¹'〜Ｒ²⁸'は各々独立に、水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロアリール基、またはーＳｉ（Ｒ²⁹'）（Ｒ³⁰'）（Ｒ³¹'）で表される基を表す。Ｒ²⁹'〜Ｒ³¹'は各々独立に、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基、または置換もしくは無置換のヘテロアリール基を表す。］
［２］ 前記一般式（１）で表される化合物と前記一般式（２）で表される化合物で表される化合物を有機溶媒に溶解した溶液を塗布する工程を含む膜の製造方法。
［３］ 前記塗布をインクジェット方式で行う、［２］に記載の膜の製造方法。
［４］ 前記一般式（１）で表される化合物と前記一般式（２）で表される化合物を含む有機発光素子。
［５］ 前記一般式（１）で表される化合物と前記一般式（２）で表される化合物を同じ層に含む、［４］に記載の有機発光素子。
［６］ 前記一般式（１）で表される化合物が下記一般式（１’）で表される化合物である、［４］または［５］に記載の有機発光素子。

［一般式（１’）におけるＲ^A1〜Ｒ^A5の少なくとも１つはシアノ基を表し、Ｒ^A1〜Ｒ^A5の少なくとも１つは分枝アルキル置換カルバゾリル基を表し、残りのＲ^A1〜Ｒ^A5は水素原子または置換基（ただしシアノ基と分枝アルキル置換カルバゾリル基は除く）を表す。］
［７］ 前記一般式（２）のＲ²'、Ｒ⁶'、Ｒ¹⁶'、Ｒ²¹'の少なくとも１つが、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロアリール基、またはーＳｉ（Ｒ²⁹'）（Ｒ³⁰'）（Ｒ³¹'）で表される基である、［４］〜［６］のいずれか１項に記載の有機発光素子。
［８］ 前記一般式（２）のＲ²'、Ｒ⁶'、Ｒ¹⁶'、Ｒ²¹'のすべてが、各々独立に、置換もしくは無置換のアルキル基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロアリール基、またはーＳｉ（Ｒ²⁹'）（Ｒ³⁰'）（Ｒ³¹'）で表される基である、［４］〜［６］のいずれか１項に記載の有機発光素子。
［９］ 量子ドットを含む発光層を有する、［４］〜［８］のいずれか１項に記載の有機発光素子。
［１０］ 有機エレクトロルミネッセンス素子である、［４］〜［９］のいずれか１項に記載の有機発光素子。
［１１］ 遅延蛍光を放射する、［４］〜［１０］のいずれか１項に記載の有機発光素子。
［１２］ ［４］〜［１１］のいずれか１項に記載の有機発光素子を備えた照明装置。
［１３］ 白色光を発する、［１２］に記載の照明装置。
［１４］ バックライトである、［１２］または［１３］に記載の照明装置。
［１５］ 下記一般式（１２’）で表される化合物。

［一般式（１２’）において、Ｒ^A31〜Ｒ^A38の少なくとも１つがアシル基または分枝アルキル基を表し、その他のＲ^A31〜Ｒ^A38は水素原子または置換基（ただしアシル基および分枝アルキル基は除く）を表す。］
［１６］ 下記一般式（１’）で表される化合物。

［一般式（１’）におけるＲ^A1〜Ｒ ^A5の少なくとも１つはシアノ基を表し、Ｒ^A1〜Ｒ ^A5の少なくとも１つは分枝アルキル置換カルバゾリル基を表し、残りのＲ^A1〜Ｒ ^A5は水素原子または置換基（ただしシアノ基と分枝アルキル置換カルバゾリル基は除く）を表す。］ [1] A film containing a compound represented by the following general formula (1) and a compound represented by the following general formula (2).

[In the general formula (1), at least one of R ¹ to R ⁵ represents a cyano group, at least one of R ¹ to R ⁵ represents a group represented by the following general formula (11), the remaining R ^{1 to} R ^{5 each} represents a hydrogen atom or a substituent (excluding a cyano group and a group represented by the general formula (11)). ]

[In General Formula (11), R ^{21 to} R ²⁸ each independently represents a hydrogen atom or a substituent. However, at least one of the following <A> or <B> is satisfied.
<A> R ²⁵ and R ²⁶ together form a single bond.
<B> R ²⁷ and R ²⁸ together represent an atomic group necessary for forming a substituted or unsubstituted benzene ring. ]

[In General Formula (2), R ¹ ′ to R ²⁸ ′ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or — It represents a group represented by Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′). R ²⁹ ′ to R ³¹ ′ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ]
[2] A method for producing a film comprising a step of applying a solution obtained by dissolving a compound represented by the general formula (1) and a compound represented by the general formula (2) in an organic solvent.
[3] The method for producing a film according to [2], wherein the coating is performed by an inkjet method.
[4] An organic light-emitting device comprising the compound represented by the general formula (1) and the compound represented by the general formula (2).
[5] The organic light-emitting device according to [4], including the compound represented by the general formula (1) and the compound represented by the general formula (2) in the same layer.
[6] The organic light-emitting device according to [4] or [5], wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1 ′).

[In the general formula (1 ') at least one of R ^A1 to R ^A5 represents a cyano group, at least one of R ^A1 to R ^A5 represents a branched alkyl substituent carbazolyl group, the remaining R ^A1 to R ^A5 Represents a hydrogen atom or a substituent (excluding a cyano group and a branched alkyl-substituted carbazolyl group). ]
[7] At least one of R ² ′, R ⁶ ′, R ¹⁶ ′, and R ²¹ ′ in the general formula (2) is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted group heteroaryl group, a group represented by Matawa ^{Si (R 29 ') (R} 30') (R 31 '), [4] the organic light-emitting device according to any one of to [6].
[8] R ² ′, R ⁶ ′, R ¹⁶ ′, and R ²¹ ′ in the general formula (2) are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted group. or unsubstituted heteroaryl group, a group represented by Matawa ^{Si (R 29 ') (R} 30') (R 31 '), the organic according to any one of [4] to [6] Light emitting element.
[9] The organic light-emitting device according to any one of [4] to [8], which includes a light-emitting layer including quantum dots.
[10] The organic light-emitting device according to any one of [4] to [9], which is an organic electroluminescence device.
[11] The organic light-emitting element according to any one of [4] to [10], which emits delayed fluorescence.
[12] An illumination device including the organic light-emitting element according to any one of [4] to [11].
[13] The illumination device according to [12], which emits white light.
[14] The illumination device according to [12] or [13], which is a backlight.
[15] A compound represented by the following general formula (12 ′).

In General formula (12 '), at least one of an acyl group or a branched alkyl group, the other R ^A31 to R ^A38 is a hydrogen atom or a substituent (wherein the acyl group and a branched alkyl group of R ^A31 to R ^A38 Is excluded). ]
[16] A compound represented by the following general formula (1 ′).

[In the general formula (1 ') at least one of R ^A1 to R ^A5 represents a cyano group, at least one of R ^A1 to R ^A5 represents a branched alkyl substituent carbazolyl group, the remaining R ^A1 to R ^A5 Represents a hydrogen atom or a substituent (excluding a cyano group and a branched alkyl-substituted carbazolyl group). ]

  According to the present invention, an organic light emitting device that emits light in a long wavelength region with high luminous efficiency and has a long driving life while using a compound in which two or more cyano groups and one or more carbazolyl groups are substituted on the benzene ring. Can be realized.

It is a schematic sectional drawing which shows the layer structural example of an organic electroluminescent element.

Hereinafter, the contents of the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In the present specification, a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value. The isotope species of the hydrogen atom present in the molecule of the compound used in the present invention is not particularly limited. For example, all the hydrogen atoms in the molecule may be ¹ H, or a part or all of them are ² H (deuterium Rium D) may be used.

[Compound represented by general formula (1)]
In the present invention, a compound represented by the following general formula (1) is used.

一般式（１１）において、Ｒ²¹〜Ｒ²⁸は、各々独立に水素原子または置換基を表す。ただし、下記＜Ａ＞か＜Ｂ＞の少なくとも一方を満たす。両方とも満たしていてもよい。
＜Ａ＞ Ｒ²⁵およびＲ²⁶は一緒になって単結合を形成する。
＜Ｂ＞ Ｒ²⁷およびＲ²⁸は一緒になって置換もしくは無置換のベンゼン環を形成するのに必要な原子団を表す。 In the general formula (1), at least one of R ¹ to R ⁵ represents a cyano group, at least one of R ¹ to R ⁵ represents a group represented by the following general formula (11), the remaining R ¹ to R ⁵ represents a hydrogen atom or a substituent (provided that a group represented by the cyano group and the general formula (11) is excluded).

In the general formula (11), R ^{21 to} R ²⁸ each independently represent a hydrogen atom or a substituent. However, at least one of the following <A> or <B> is satisfied. Both may be satisfied.
<A> R ²⁵ and R ²⁶ together form a single bond.
<B> R ²⁷ and R ²⁸ together represent an atomic group necessary for forming a substituted or unsubstituted benzene ring.

In the general formula (1), at least one of R ^{1 to} R ⁵ represents a cyano group. When any one is a cyano group, the cyano group may be any of R ^{1 to} R ³ . When any two are cyano groups, a combination of R ¹ and R ^{3 or} a combination of R ² and R ⁴ can be exemplified. When any three are cyano groups, combinations of R ¹ , R ³ and R ⁴ can be exemplified.

In the general formula (1), at least one of R ^{1 to} R ⁵ represents a group represented by the general formula (11). When two or more represent groups represented by the general formula (11), they may be the same or different, but are more preferably the same.
The group represented by the general formula (11) preferably has, for example, a structure represented by any of the following general formulas (12) to (15). In particular, it is preferable to have a structure represented by the following general formula (12).

In the general formulas (12) to (15), R ^{31 to} R ³⁸ , R ^{41 to} R ⁴⁶ , R ^{51 to} R ⁶² and R ^{71 to} R ⁸⁰ each independently represent a hydrogen atom or a substituent. The substitution position and the number of substitutions when the groups represented by the general formulas (12) to (15) have a substituent are not particularly limited. The number of substitution of each group is preferably 0 to 6, more preferably 0 to 4, and for example, preferably 0 to 2. When having a plurality of substituents, they may be the same or different from each other, but are preferably the same.
When the group represented by the general formula (12) has a substituent, any of R ^{32 to} R ³⁷ is preferably a substituent. For example, the case where R ³² and R ³⁷ are substituents, the case where R ³³ and R ³⁶ are substituents, and the case where R ³⁴ and R ³⁵ are substituents can be preferably exemplified.
When the group represented by the general formula (13) has a substituent, any of R ^{42 to} R ⁴⁶ is preferably a substituent. For example, a case where R ⁴² is a substituent and a case where R ⁴³ is a substituent can be preferably exemplified.
When the group represented by the general formula (14) has a substituent, any of R ^{52 to} R ⁶⁰ is preferably a substituent. For example, when any of R ^{52 to} R ⁵⁴ is a substituent, a case where any of R ^{55 to} R ⁶⁰ is a substituent can be preferably exemplified.
When the group represented by the general formula (15) has a substituent, any of R ^{72 to} R ⁷⁴ and R ^{77 to} R ⁷⁹ is preferably a substituent. For example, when R ⁷² and R ⁷⁹ are substituents, R ⁷³ and R ⁷⁸ are substituents, R ⁷⁴ and R ⁷⁷ are substituents, R ⁷² , R ⁷⁴ , R ⁷⁷ and R ⁷⁹ are The case where it is a substituent can be illustrated preferably. In particular, when R ⁷⁴ and R ⁷⁷ are substituents, the case where R ⁷² , R ⁷⁴ , R ⁷⁷ and R ⁷⁹ are substituents can be exemplified more preferably. The substituents at this time are particularly preferably each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms. And more preferably an unsubstituted alkyl group, an unsubstituted aryl group having 6 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms substituted with an aryl group having 6 to 10 carbon atoms.

Formula (11) R ²¹ to R ²⁸ in the general formula (12) R ³¹ to R ^38, and R ⁵¹ to R ⁶² and R ⁴¹ to R ⁴⁶ in the general formula (13), the general formula (14), generally Examples of the substituent that R ^{71 to} R ^{80 in} formula (15) can take include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and 1 to 20 carbon atoms. An alkylthio group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, and a diaryl having 12 to 40 carbon atoms Amino group, substituted or unsubstituted carbazolyl group having 12 to 40 carbon atoms, alkenyl group having 2 to 10 carbon atoms, alkynyl group having 2 to 10 carbon atoms, alkoxycarbonyl group having 2 to 10 carbon atoms, 1 to 10 carbon atoms Alkylsulfonyl group of charcoal An alkylamide group having 2 to 10 carbon atoms, an arylamide group having 7 to 41 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a trialkylsilylalkyl group having 4 to 20 carbon atoms, and a trialkyl having 5 to 20 carbon atoms A silylalkenyl group, a C5-C20 trialkylsilylalkynyl group, a nitro group, etc. are mentioned. Among these specific examples, those that can be substituted with a substituent may be further substituted. More preferred substituents are a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, carbon A substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, a substituted or unsubstituted diarylamino group having 12 to 40 carbon atoms, and a substituted or unsubstituted carbazolyl group having 12 to 40 carbon atoms. More preferable substituents are a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, and a substituted group having 1 to 10 carbon atoms. Or an unsubstituted dialkylamino group, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

  As used herein, the alkyl group may be linear, branched, or cyclic. Also, two or more of the straight chain portion, the cyclic portion and the branched portion may be mixed. Carbon number of an alkyl group can be 1 or more, 2 or more, 4 or more, 6 or more, for example. Moreover, carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group it can.

  The aryl group referred to in this specification may be a group composed of only one aromatic hydrocarbon ring, or may be a group obtained by condensing one or more rings to an aromatic hydrocarbon ring. When the aromatic hydrocarbon ring is a group in which one or more rings are condensed, at least one of the aromatic hydrocarbon ring, the aliphatic hydrocarbon ring, and the non-aromatic heterocyclic ring is condensed to the aromatic hydrocarbon ring. The selected group can be employed. Carbon number of an aryl group can be 6 or more, 10 or more, 14 or more, 18 or more, for example. Moreover, carbon number can be 30 or less, 18 or less, 14 or less, and 10 or less. Specific examples of the aryl group include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, A 4-carbazolyl group can be mentioned.

  The heteroaryl group referred to in this specification may be a group composed of only one heteroaromatic ring, or may be a group obtained by condensing one or more rings to a heteroaromatic ring. When the heteroaromatic ring is a group in which one or more rings are condensed, at least one of the aromatic hydrocarbon ring, heteroaromatic ring, aliphatic hydrocarbon ring and non-aromatic heterocyclic ring is an aromatic hydrocarbon ring. A group condensed to can be employed. The number of atoms constituting the ring skeleton of the heteroaryl group can be, for example, 5 or more, 6 or more, 10 or more, 14 or more, or 18 or more. Moreover, carbon number can be 30 or less, 18 or less, 14 or less, and 10 or less. The heteroaryl group may be a group bonded through a hetero atom or a group bonded through a carbon atom constituting a heteroaromatic ring. Examples of the hetero atom constituting the ring skeleton of the heteroaromatic ring of the heteroaryl group include a nitrogen atom, an oxygen atom, and a sulfur atom. Specific examples of the heteroaryl group include 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, triazinyl group, 9-carbazolyl group, 10-phenoxazyl group. A 10-phenothiazyl group can be mentioned.

  Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  The alkenyl group as used herein may be linear, branched, or cyclic. Also, two or more of the straight chain portion, the cyclic portion and the branched portion may be mixed. The carbon number of the alkenyl group can be, for example, 2 or more, 4 or more, or 6 or more. Moreover, carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less. Specific examples of the alkenyl group include ethenyl group, n-propenyl group, isopropenyl group, n-butenyl group, isobutenyl group, tert-butenyl group, n-pentenyl group, isopentenyl group, n-hexenyl group, isohexenyl group, List 2-ethylhexenyl group, n-heptenyl group, isoheptenyl group, n-octenyl group, isooctenyl group, n-nonel group, isononel group, n-decenyl group, isodecenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group be able to.

  The alkynyl group referred to in this specification may be linear, branched or cyclic. Also, two or more of the straight chain portion, the cyclic portion and the branched portion may be mixed. The number of carbon atoms of the alkynyl group can be, for example, 2 or more, 4 or more, or 6 or more. Moreover, carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, and 4 or less. Specific examples of the alkenyl group include ethynyl group, n-propynyl group, isopropynyl group, n-butynyl group, isobutynyl group, tert-butynyl group, n-pentynyl group, isopentynyl group, n-hexynyl group, isohexynyl group, 2- Examples include ethylhexynyl group, n-heptynyl group, isoheptynyl group, n-octynyl group, isooctynyl group, n-nonyl group, isononyl group, n-decynyl group, isodecynyl group, cyclohexynyl group, and cycloheptynyl group.

  Description and specific examples of the alkyl part of the alkoxy group referred to in the present specification, description and specific example of the alkyl part of the alkylthio group, description and specific example of the alkyl part of the alkyl-substituted amino group referred to in the present specification, and the present specification Description and specific examples of the alkyl part of the acyl group (the part obtained by removing the carbonyl group from the acyl group), description and specific examples of the alkyl part of the alkoxycarbonyl group as used herein, and alkyl part of the alkylsulfonyl group as used herein Description and specific examples, description and specific examples of the alkyl portion of the alkylamide group referred to in the present specification, description and specific examples of the alkyl portion of the trialkylsilyl group referred to in the present specification, and trialkylsilylalkyl referred to in the present specification. Description and specific examples of each alkyl part of the group, description and specific examples of the alkyl part of the trialkylsilylalkenyl group referred to in this specification, Description and specific examples of the alkyl moiety of the trialkylsilyl alkynyl groups referred, reference can be made to the descriptions and specific examples of the above-described alkyl group.

For the description and specific examples of the aryl moiety of the diarylamino group referred to in this specification, and the description and specific examples of the aryl moiety of the arylamide group referred to in this specification, refer to the description and specific examples of the aryl group described above. it can.
For the description and specific examples of the alkenyl part of the trialkylsilylalkenyl group referred to in this specification, the description and specific examples of the alkenyl group can be referred to.
For the description and specific examples of the alkynyl part of the trialkylsilylalkynyl group referred to in the present specification, the description and specific examples of the above alkynyl group can be referred to.

Illustrating a preferred embodiment of the present invention, the group represented by the general formula (11) is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 1,2,3,4-tetrahydro-9-carbazolyl. It is preferably a group, a substituted or unsubstituted 1-indolyl group, or a substituted or unsubstituted diarylamino group. That is, any ^one of R ^{1 to} R ^{5 in} the general formula (1) is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, It is preferably a substituted or unsubstituted 1-indolyl group or a substituted or unsubstituted diarylamino group. Any two or more of R ^{1 to} R ^{5 in} the general formula (1) are substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted 1,2,3,4-tetrahydro-9-carbazolyl group, substituted Or it is more preferably an unsubstituted 1-indolyl group or a substituted or unsubstituted diarylamino group.

In General Formula (1), when any one of R ^{1 to} R ⁵ is a group represented by General Formula (11), it may be any of R ^{1 to} R ³ . When any two are groups represented by the general formula (11), a combination of R ¹ and R ^{3 or} a combination of R ² and R ⁴ can be exemplified. When any three are groups represented by the general formula (11), combinations of R ¹ , R ³ and R ⁴ can be exemplified.

  One of the two ortho positions of the benzene ring to which the group represented by the general formula (11) is bonded is preferably a cyano group. Both of the two ortho positions may be a cyano group. When two or more groups represented by the general formula (11) are bonded to the benzene ring, at least two of them are bonded to the group represented by the general formula (11). It is preferable to satisfy the condition that any one of the two ortho positions of the ring is a cyano group.

In the general formula (1), at least one of R ¹ to R ⁵ represents a cyano group, at least one of R ¹ to R ⁵ represents a group represented by the general formula (11), the remaining R ^{1 to} R ^{5 each} represents a hydrogen atom or a substituent (excluding a cyano group and a group represented by the general formula (11)).

Preferable substituents that R ^{1 to} R ⁵ can take include, for example, a hydroxy group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, and 1 carbon atom. -20 alkyl-substituted amino group, C2-C20 acyl group, C6-C40 aryl group, C3-C40 heteroaryl group, C2-C10 alkenyl group, C2-C10 Alkynyl group, C2-C10 alkoxycarbonyl group, C1-C10 alkylsulfonyl group, amide group, C2-C10 alkylamide group, C3-C20 trialkylsilyl group, carbon number 4 to 20 trialkylsilylalkyl group, 5 to 20 trialkylsilylalkenyl group, 5 to 20 trialkylsilylalkynyl group and nitro group And the like. Among these specific examples, those that can be substituted with a substituent may be further substituted. More preferred substituents are a hydroxy group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and a substituted or unsubstituted group having 1 to 20 carbon atoms. A dialkylamino group, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms. More preferred substituents are a hydroxy group, a fluorine atom, a chlorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, and a substituted group having 1 to 10 carbon atoms. Or an unsubstituted dialkylamino group, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Still more preferably, they are a hydroxy group, a fluorine atom, and a chlorine atom.

In the general formula (1), among R ^{1 to} R ⁵ , the number of hydrogen atoms is preferably 3 or less, more preferably 2 or less, still more preferably 1 or less, 0 It is also preferable.

As a preferable combination, for example, ¹ to 4 of R ^{1 to} R ^{5 in} the general formula (1) are cyano groups, and at least one of R ^{1 to} R ⁵ is a substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted. 1, 2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted 1-indolyl group, or a substituted or unsubstituted diarylamino group, and the remaining R ^{1 to} R ⁵ are A case where each is independently a hydroxy group or a halogen atom can be exemplified. As another preferred combination, ¹ to 4 of R ^{1 to} R ⁵ are cyano groups, and the remaining R ^{1 to} R ⁵ are each independently a substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted 1, Examples include a 2,3,4-tetrahydro-9-carbazolyl group, a substituted or unsubstituted 1-indolyl group, or a substituted or unsubstituted diarylamino group. As another preferred combination, ¹ to 4 of R ^{1 to} R ^{5 in} the general formula (1) are cyano groups, at least one of R ^{1 to} R ⁵ is a substituted or unsubstituted 9-carbazolyl group, and the rest The case where R < ¹ > -R < ⁵ > is a hydroxyl group or a halogen atom each independently can also be mentioned. As another preferred combination, mention may be made of the case where 1 to 4 of R ^{1 to} R ^{5 in} the general formula (1) are cyano groups and the remaining R ^{1 to} R ⁵ are substituted or unsubstituted 9-carbazolyl groups. You can also. As another preferred combination, ¹ to 3 of R ^{1 to} R ^{5 in} the general formula (1) are cyano groups, at least one of R ^{1 to} R ⁵ is a substituted or unsubstituted 9-carbazolyl group, and the rest The case where R < ¹ > -R < ⁵ > is a hydroxy group (however, at least 1 of R < ¹ > -R < ⁵ > is a hydroxyl group) can also be mentioned. As another preferred combination, at least 1 to 3 of R ^{1 to} R ^{5 in} the general formula (1) are cyano groups, at least one of R ^{1 to} R ⁵ is a substituted or unsubstituted 9-carbazolyl group, and the rest The case where R ^{1 to} R ⁵ are halogen atoms (however, at least one of R ^{1 to} R ⁵ is a halogen atom) can also be mentioned.

Hereinafter, specific examples of the compound represented by the general formula (1) will be exemplified, but the compound represented by the general formula (1) that can be used in the present invention is limitedly interpreted by these specific examples. It shouldn't be. In addition, in the following exemplary compounds, when two or more groups represented by any one of the general formulas (12) to (15) are present in the molecule, these groups all have the same structure. For example, in the compound 1 of Table 1, R ¹ , R ² , R ⁴ and R ⁵ in the general formula (1) are groups represented by the general formula (12), and these groups are all unsubstituted. 9-carbazolyl group. Moreover, what is described as the formulas (21) to (24) in the following table is the formulas (21) to (24) described later in this specification. In the case of performing solution casting, for example, compounds 1101 to 1112 can be preferably employed.

Hereinafter, still another specific example of the compound represented by the general formula (1) will be exemplified. The general formula (12a) and general formula (12b) in the following table are as follows. Further, “* 1” in Tables 8 and 9 represents a position bonded to the benzene ring of the general formula (1).

The structures of D1 to D60 and A1 to A13 in Tables 8 to 10 are shown below.

[Synthesis Method of Compound Represented by General Formula (1)]
The compound represented by the general formula (1) can be synthesized by applying a known synthesis method. For example, it can be synthesized by reacting a compound represented by the following general formula (3) with a compound represented by the following general formula (11 ′).

At least one of R ^B1 to R ^B5 in the general formula (3) represents a cyano group, at least one of R ^B1 to R ^B5 represents a halogen atom, the remaining R ^B1 to R ^B5 hydrogen atom or a substituent ( However, a cyano group and a halogen atom are excluded). Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. For the explanation and specific examples of R ^{21 to} R ²⁸ in the general formula (11 ′), the corresponding explanation and specific examples in the general formula (11) can be referred to.
By reacting the compound represented by the general formula (3) with the compound represented by the general formula (11 ′), the halogen atom of the general formula (3) is bonded to the position of the general formula (11 ′). The partial structure is substituted, and as a result, a compound represented by the general formula (1) is obtained. By appropriately selecting the bonding position of the halogen atom in the compound represented by the general formula (3), a compound in which the partial structure of the general formula (11 ′) is substituted at a desired position can be obtained.
For specific reaction conditions and reaction steps, the following synthesis examples can be referred to.

The compound represented by the general formula (11 ′) used for the reaction includes a compound represented by the following general formula (12 ′). For the description and specific examples of R ^{A31 to} R ^{A38 in} the general formula (12 ′), the corresponding description and specific examples in the general formula (12) can be referred to.

In the general formula (12 ′), a compound in which at least one of R ^{A31 to} R ^A38 is an alkyl group introduces an acyl group by reacting carbazole with an acyl chloride, and reduces the acyl group to convert it to an alkyl group. Can be obtained. The acyl group introduction reaction can be carried out, for example, in a methylene chloride solvent in the presence of aluminum chloride. In addition, the conversion reaction to an alkyl group can be performed, for example, by allowing LiAlH ₄ to act in tetrahydrofuran in the presence of aluminum chloride. For specific reaction conditions and reaction steps of these reactions, the following synthesis examples can be referred to.

Examples of the acyl-substituted carbazole and alkyl-substituted carbazole obtained as the reaction intermediate include compounds belonging to the following groups. R ^A31 are described below to R ^A38 is R ^A31 to R ^A38 in the general formula (12 ').
(1) A compound in which at least one of R ^{A31 to} R ^A38 is an acyl group.
For example, at least one compound is an acyl group having at least 2 carbon atoms R ^A31 to R ^A38, at least one of R ^A31 to R ^A38 is a acyl group having 3 or more carbon atoms compound, at least one of R ^A31 to R ^A38 A compound in which one is an acyl group having 4 or more carbon atoms, a compound in which at least one of R ^{A31 to} R ^A38 is an acyl group having 5 or more carbon atoms, or at least one of R ^{A31 to} R ^A38 is an acyl group having 6 or more carbon atoms A compound, a compound in which at least one of R ^{A31 to} R ^A38 is an acyl group having 7 or more carbon atoms, a compound in which R ^A33 is an acyl group, a compound in which at least two of R ^{A31 to} R ^A38 are acyl groups, R ^A33 and R A ^A compound in which ^A36 is each independently an acyl group, a compound in which R ^A33 and R ^A36 are the same acyl group, a compound in which at least one of R ^{A31 to} R ^A38 is a branched acyl group, and at least one of R ^{A31 to} R ^A38 is 2 or more carbon atoms Compound alkyl moiety of which is 2 or more include an acyl group, a compound having a symmetrical structure and at least two of the acyl group R ^A31 to R ^A38, at least one of R ^A31 to R ^A38 although other an acyl group Mention may be made of compounds wherein R is a hydrogen atom.
(2) A compound in which at least one of R ^{A31 to} R ^A38 is a branched alkyl group.
For example, at least one compound is of 4 or more branched alkyl group having a carbon of R ^A31 to R ^A38, at least one compound is a branched alkyl group having 5 or more carbon atoms of R ^A31 ~R ^A38, R ^A31 ~R ^A compound in which at least one of ^A38 is a branched alkyl group having 6 or more carbon atoms, a compound in which at least one of R ^{A31 to} R ^{A38 is} a branched alkyl group having 7 or more carbon atoms, or at least one of R ^{A31 to} R ^A38 is carbon A compound having a branched alkyl group having a number of 8 or more, a compound in which R ^A33 is a branched alkyl group, a compound in which at least two of R ^{A31 to} R ^A38 are branched alkyl groups, R ^A33 and R ^A36 are each independently A compound having a branched alkyl group, a compound in which R ^A33 and R ^A36 are the same branched alkyl group, a compound having a symmetric structure in which at least two of R ^{A31 to} R ^A38 are branched alkyl groups, and R ^{A31 to} R ^A38 At least one is two Compounds are ethylhexyl group, the other R and at least one is a branched alkyl group of R ^A31 to R ^A38 can be mentioned a compound having a hydrogen atom.

A compound represented by the following general formula (1 ′) can be synthesized by reacting the alkyl-substituted carbazole represented by the general formula (12 ′) according to the above reaction formula.

At least one of R ^A1 to R ^A5 in Formula (1 ') represents a cyano group, at least one of R ^A1 to R ^A5 represents a branched alkyl substituent carbazolyl group, the remaining R ^A1 to R ^A5 hydrogen Represents an atom or a substituent (excluding a cyano group and a branched alkyl-substituted carbazolyl group).

The number of cyano groups may be 1 to 3 of R ^{A1 to} R ^A5 , 1 to 2 or 1. For example, at least R ^A2 can be a cyano group. The branched alkyl-substituted carbazolyl group can be 1 to 4 of R ^{A1 to} R ^A5 , 2 to 4, 3 to 4, or 4. For example, at least R ^A1 can be a branched alkyl-substituted carbazolyl group, at least R ^A2 can be a branched alkyl-substituted carbazolyl group, or at least R ^A3 can be a branched alkyl-substituted carbazolyl group. Further, at least R ^A1 and R ^A3 are branched alkyl-substituted carbazolyl groups, at least R ^A1 and R ^A4 are branched alkyl-substituted carbazolyl groups, at least R ^A1 and R ^A5 are branched alkyl-substituted carbazolyl groups, At least R ^A3 and R ^A4 can be a branched alkyl-substituted carbazolyl group, and at least R ^A3 and R ^A5 can be a branched alkyl-substituted carbazolyl group.
For the description and specific examples of the branched alkyl group in the branched alkyl-substituted carbazolyl group, the description and specific examples of the branched alkyl group of the general formula (12 ′) can be referred to. Examples of the branched alkyl-substituted carbazolyl group include a group in which the 9-position hydrogen atom in General Formula (12 ′) has been removed.

[Compound represented by formula (2)]
In the present invention, a compound represented by the following general formula (2) is used.

In the general formula (2), R ¹ ′ to R ²⁸ ′ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or —Si It represents a group represented by (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′).

For the description and specific examples of the alkyl group that R ¹ ′ to R ²⁸ ′ can take, the description and specific examples of the alkyl group in the general formula (1) can be referred to.
Of R ¹ ′ to R ²⁸ ′ in the general formula (2), the number of alkyl groups can be, for example, 0 or more, 1 or more, 2 or more, 4 or more, 6 or more, or 8 or more. The number of alkyl groups of R ¹ 'to R ^28' in formula (2), for example 28 or less, 18 or less, 12 or less, 8 or less, 4 or less, can be 2 or less.

For the description and specific examples of the aryl group that R ¹ ′ to R ²⁸ ′ can take, the description and specific examples of the alkyl group in the general formula (1) can be referred to.
Among R ¹ ′ to R ²⁸ ′ in the general formula (2), the number of aryl groups can be, for example, 0 or more, 1 or more, 2 or more, 4 or more, 6 or more, or 8 or more. The number of the aryl group of R ¹ 'to R ^28' in formula (2), for example 28 or less, 18 or less, 12 or less, 8 or less, 4 or less, can be 2 or less.

For the description and specific examples of the heteroaryl group which R ¹ ′ to R ²⁸ ′ can take, the description and specific examples of the alkyl group in the general formula (1) can be referred to.
Of R ¹ ′ to R ²⁸ ′ in the general formula (2), the number of heteroaryl groups can be, for example, 0 or more, 1 or more, 2 or more, 4 or more, 6 or more, or 8 or more. The number of the heteroaryl group of R ¹ 'to R ^28' in formula (2), for example 28 or less, 18 or less, 12 or less, 8 or less, 4 or less, can be 2 or less.

  The above alkyl group, aryl group, and heteroaryl group each may have a substituent. Examples of such substituents include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, and a dialkyl having 1 to 20 carbon atoms. An amino group, a diarylamino group having 12 to 30 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, C2-C10 alkynyl group, C2-C10 alkoxycarbonyl group, C1-C10 alkylsulfonyl group, amide group, C2-C10 alkylamide group, C3-C20 trialkyl Silyl group, trialkylsilylalkyl group having 4 to 20 carbon atoms, trialkylsilylalkenyl group having 5 to 20 carbon atoms, trialkylsilylal group having 5 to 20 carbon atoms Alkenyl group and a nitro group and the like. Among these specific examples, those that can be further substituted with a substituent may be substituted with, for example, the substituents of these specific examples.

R ¹ '~R ^28' over can take ^{Si (R 29 ') (R} 30') 'R 29 in the group represented by (R ^31)' ~R ³¹ 'are each independently a substituted or unsubstituted An alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. For the substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group herein, refer to the corresponding descriptions and ranges in the description of R ¹ ′ to R ²⁸ ′. Can do.
R ²⁹ ′ to R ³¹ ′ may be the same as or different from each other. Also, two of the three may be the same and one may be different, or all three may be different from each other. R ²⁹ ′ to R ³¹ ′ may be each independently a substituted or unsubstituted alkyl group (trialkylsilyl group), or each independently a substituted or unsubstituted aryl group (triarylsilyl group). Furthermore, each may be independently a substituted or unsubstituted heteroaryl group (triheteroarylsilyl group). At least one of R ²⁹ ′ to R ³¹ ′ may be a substituted or unsubstituted alkyl group, at least one may be a substituted or unsubstituted aryl group, and at least one of R ²⁹ ′ to R ³¹ ′ may be substituted. Alternatively, it may be an unsubstituted alkyl group, at least one of which may be a substituted or unsubstituted heteroaryl group, and at least one of R ²⁹ ′ to R ³¹ ′ may be a substituted or unsubstituted aryl group, and at least one of them may be a substituted or unsubstituted heteroaryl group. It may be a substituted or unsubstituted heteroaryl group. Further, one of R ²⁹ ′ to R ³¹ ′ may be a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
As the group represented by —Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′), for example, trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, tert-butyldimethyl Examples thereof include a silyl group, a dimethylphenylsilyl group, a tert-butyldiphenylsilyl group, a dimethyl (pentafluorophenyl) silyl group, and a tribenzylsilyl group.
Of R ¹ ′ to R ²⁸ ′ in the general formula (2), the number of groups represented by —Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′) is, for example, 0 or more, 1 or more, 2 or more 4 or more, 6 or more, 8 or more. The number of groups represented by —Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′) in R ¹ ′ to R ²⁸ ′ of the general formula (2) is, for example, 28 or less, 18 or less, It can be 12 or less, 8 or less, 4 or less, 2 or less.

At least one of R ¹ ′ to R ²⁸ ′ in the general formula (2) is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or —Si ( R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′) [In the following, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or — The group represented by Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′) is preferably referred to as “specific substituent”. The number of specific substituents among R ¹ ′ to R ²⁸ ′ can be, for example, 2 or more, 4 or more, 6 or more, or 8 or more. Moreover, the number of the specific substituents among R ¹ ′ to R ²⁸ ′ can be, for example, 28 or less, 18 or less, 12 or less, 8 or less, and 4 or less.
The position at which the specific substituent is substituted is not particularly limited. For example, the number of specific substituents per benzene ring can be 0 to 3, 0 to 2, 0, or 1. For example, the specific substituent can be present at any position selected from the following first group, and the number thereof is 1 or more, 2 or more, 3 or more, 4 or more, 12 or less, 8 Below, it can be 4 or less, or 2 or less. The specific substituent may be present at any position selected from the following second group, and the number thereof is 1 or more, 2 or more, 3 or more, 4 or more, 8 or less, 6 or less, 4 or less, or 2 or less. The specific substituent can also be present at any position selected from the following third group, and the number thereof is 1 or more, 2 or more, 3 or more, 4 or more, 8 or less, 6 or less, 4 or less, or 2 or less. The number of specific substituents in the first group may be 0, the number of specific substituents in the second group may be 0, and the number of specific substituents in the third group may be 0.
(First group) R ¹ ′, R ⁴ ′, R ⁵ ′, R ⁸ ′, R ⁹ ′, R ¹³ ′, R ¹⁴ ′, R ¹⁸ ′, R ¹⁹ ′, R ²³ ′, R ²⁴ ′, R ²⁸ '
(Group ^{2) R 10 ', R 12'} , R 15 ', R 17', R 20 ', R 22', R 25 ', R 27'
(Group 3) R ² ′, R ³ ′, R ⁶ ′, R ⁷ ′, R ¹¹ ′, R ¹⁶ ′, R ²¹ ′, R ²⁶ ′

Specific examples of the substitution position of the specific substituent include ^{six of} R ² ′, R ⁶ ′, R ¹¹ ′, R ¹⁶ ′, R ²¹ ′, R ²⁶ ′; R ² ′, R ⁶ ′, R ⁹ ′, 4 of R ²⁴ ′; 4 of R ² ′, R ⁶ ′, R ¹⁰ ′, R ²⁵ ′; 4 of R ² ′, R ⁶ ′, R ¹⁴ ′, R ¹⁹ ′; R ² ′, R ^{6 ', R 15', R} 20 ' ^{four; R 2', R 6 '} , R 16', R 21 ' ^{four; R 11', R 16 '} , R 21', 4 of R ²⁶ 'one; R ² ', R ^6' two; R ² ', R ^11' two; R ² ', R ^16' two; R ² ', R ^21' two; R ² ', Two of R ²⁶ ′; Two of R ¹¹ ′ and R ²¹ ′; Two of R ¹⁴ ′ and R ¹⁹ ′; Two of R ¹⁵ ′ and R ²⁰ ′; Two of R ¹⁶ ′ and R ²¹ ′ One of R ² ′; one of R ¹⁰ ′; one of R ¹¹ ′.
As a preferred example, when four of R ² ′, R ⁶ ′, R ¹⁶ ′ and R ²¹ ′ are specific substituents, further four of R ² ′, R ⁶ ′, R ¹⁶ ′ and R ²¹ ′ The case where it is a specific substituent and other R is a hydrogen atom can be mentioned. As another preferred example, when four of R ² ′, R ⁶ ′, R ¹⁶ ′, and R ²¹ ′ are substituted or unsubstituted alkyl groups, R ² ′, R ⁶ ′, R ¹⁶ ′, Examples include the case where four of R ²¹ ′ are unsubstituted alkyl groups and the other R is a hydrogen atom. As another preferred example, when four of R ² ′, R ⁶ ′, R ¹⁶ ′, and R ²¹ ′ are alkyl groups having 1 to 12 carbon atoms, R ² ′, R ⁶ ′, R ¹⁶ ′ , R ²¹ ′ is an alkyl group having 1 to 12 carbon atoms, and the other R is a hydrogen atom. As another preferred example, when four of R ² ′, R ⁶ ′, R ¹⁶ ′, and R ²¹ ′ are alkyl groups having 4 to 12 carbon atoms, R ² ′, R ⁶ ′, R ¹⁶ ′ , R ²¹ ′ is an alkyl group having 4 to 12 carbon atoms, and the other R is a hydrogen atom. When the compound represented by the general formula (2) is formed by vapor deposition, the alkyl group preferably has 1 to 4 carbon atoms, and when the compound represented by the general formula (2) is formed by solution deposition, the alkyl group is alkyl. The group preferably has 4 to 12 carbon atoms. As another preferred example, when four of R ² ′, R ⁶ ′, R ¹⁶ ′, and R ²¹ ′ are tert-butyl groups, R ² ′, R ⁶ ′, R ¹⁶ ′, R ²¹ ′ 4 is a tert-butyl group, and the other R is a hydrogen atom. As another preferred example, when four of R ² ′, R ⁶ ′, R ¹⁶ ′ and R ²¹ ′ are 2-ethylhexyl groups, R ² ′, R ⁶ ′, R ¹⁶ ′ and R ²¹ ′ 4 are 2-ethylhexyl groups and the other R is a hydrogen atom.
Note that two adjacent Rs or three Rs out of R ¹ ′ to R ²⁸ ′ in the general formula (2) are not connected to each other to form a ring structure.

The following table | surface shows the specific example of a compound represented by General formula (2).

The molecular weight of the compound represented by the general formula (1) or the compound represented by the general formula (2) is, for example, when it is intended to use an organic layer containing these compounds by forming a film by a vapor deposition method. It is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 800 or less. The lower limit value of the molecular weight is the molecular weight of the minimum compound represented by the general formula (1) and the molecular weight of the minimum compound represented by the general formula (2).
The compound represented by the general formula (1) and the compound represented by the general formula (2) may be formed by a coating method regardless of the molecular weight. If a coating method is used, a film can be formed even with a compound having a relatively large molecular weight.

By applying the present invention, a compound containing a plurality of structures represented by the general formula (1) in the molecule, a compound containing a plurality of structures represented by the general formula (2) in the molecule, It is also conceivable to use a compound including a structure represented by one or more general formulas (1) and a structure represented by one or more general formulas (2).
For example, a polymer obtained by polymerizing the polymerizable group in advance in the presence of a polymerizable group in the structure represented by the general formula (1) or the structure represented by the general formula (2) It is possible to use it. Specifically, a monomer containing a polymerizable functional group in any of R ^{1 to} R ^{5 in} the general formula (1) or a polymerizable functional group in any of R ¹ ′ to R ²⁸ ′ in the general formula (2). It is conceivable to prepare a monomer containing and polymerize it alone or copolymerize with other monomers to obtain a polymer having a repeating unit and use the polymer as a charge transport material. Alternatively, the compounds having the structure represented by the general formula (1) are coupled to each other, the compounds having the structure represented by the general formula (2) are coupled to each other, or represented by the general formula (1). It is also conceivable to obtain a dimer or trimer by coupling a compound having a structure with a compound having a structure represented by the general formula (2).

As an example of the polymer having a repeating unit including the structure represented by the general formula (1), a polymer including a structure represented by the following general formula (4) or (5) can be given.

In the general formula (4) or (5), Q represents a group represented by the structure represented by the general formula (1) or a structure represented by the general formula (2), and L ¹ and L ² represent a linking group. . Carbon number of a coupling group becomes like this. Preferably it is 0-20, More preferably, it is 1-15, More preferably, it is 2-10. And preferably has a structure represented by - linking group -X ¹¹ -L ^11. Here, X ¹¹ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. L ¹¹ represents a linking group, preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted group A phenylene group is more preferable.
In the general formula (4) or (5), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ and R ¹⁰⁴ each independently represent a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms. An unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, and a chlorine atom, and more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms and an unsubstituted alkoxy group having 1 to 3 carbon atoms.
The linking group represented by L ¹ and L ² is any ^one of R ^{1 to} R ^{5 in} the structure of the general formula (1) constituting Q and any of R ¹ ′ to R ²⁸ ′ in the general formula (2). Can be combined. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.

Specific examples of the structure of the repeating unit include structures represented by the following formulas (21) to (24).

The polymer having a repeating unit containing these formulas (21) to (24) is any ^one of R ^{1 to} R ⁵ having the structure of the general formula (1), R ¹ ′ to R ²⁸ ′ of the general formula (2). It can be synthesized by introducing a hydroxy group into any of the above, reacting the following compound as a linker to introduce a polymerizable group, and polymerizing the polymerizable group.

  The polymer containing a structure represented by general formula (1) or general formula (2) in the molecule is a polymer composed only of repeating units having a structure represented by general formula (1) or general formula (2). It may be a polymer containing a repeating unit having other structure. In addition, the repeating unit having a structure represented by the general formula (1) or the general formula (2) included in the polymer may be a single type or two or more types. Examples of the repeating unit not having the structure represented by the general formula (1) or the general formula (2) include those derived from monomers used in ordinary copolymerization. Examples thereof include a repeating unit derived from a monomer having an ethylenically unsaturated bond such as ethylene and styrene.

[Membrane and membrane production method]
The present invention provides a film containing a compound represented by the general formula (1) and a compound represented by the general formula (2).
The combination of the compound represented by the general formula (1) and the compound represented by the general formula (2) can be arbitrarily selected. Preferable combinations include, for example, compounds 1, 4, 6, 301, 302, 304, 501, 504, and 523 represented by general formula (1) and compounds 2045 to 2291 represented by general formula (2). Any combination can be mentioned. Further, any combination of the compounds 1, 4, 6, 301, 302, 304, 501, 504, and 523 represented by the general formula (1) and the compounds 2045 to 2131 represented by the general formula (2) Can be mentioned. Further, any combination of the compounds 1, 4, 6, 301, 302, 304, 501, 504, and 523 represented by the general formula (1) and the compounds 2085 to 2131 represented by the general formula (2) Can be mentioned. Moreover, arbitrary combinations of the compounds 301, 302, and 304 represented by the general formula (1) and the compounds 2088, 2089, and 2097 represented by the general formula (2) can be given. Moreover, the arbitrary combinations of the compounds 302 and 304 represented by General formula (1) and the compound 2097 represented by General formula (2) can be mentioned.
The films containing the compound 1 and the compounds 2045 to 2291 in combination in order are specifically disclosed here as films 1 to 2045 to 1-2291, respectively. The films including the compound 4 and the compounds 2045 to 2291 in combination in order are specifically disclosed herein as films 4 to 2045 to 42921, respectively. The films including the compound 6 and the compounds 2045 to 2291 in combination in order are specifically disclosed herein as films 6 to 2045 to 62-2291, respectively. The films containing the compound 301 and the compounds 2045 to 2291 in combination in this order are specifically disclosed here as films 301 to 2045 to 301-2291, respectively. The films each including the compound 302 and the compounds 2045 to 2291 in order are specifically disclosed as films 302 to 2045 to 302-2291, respectively. The films containing the compound 304 and the compounds 2045 to 2291 in combination in order are specifically disclosed herein as films 304 to 2045 to 304-2291, respectively. The films each including the compound 501 and the compounds 2045 to 2291 in combination in order are specifically disclosed herein as films 501 to 2045 to 501 to 2291, respectively. The films containing the compound 504 and the compounds 2045 to 2291 in order are specifically disclosed here as films 504 to 2045 to 504 to 2291, respectively. The films including the compound 523 and the compounds 2045 to 2291 in combination in this order are specifically disclosed as films 523 to 2045 to 523 to 2291, respectively.

  The content of the compound represented by the general formula (1) in the film is, for example, 1 or more times the content of the compound represented by the general formula (2), 2 times or more, 5 times or more, For example, it can be 200 times or less, 100 times or less, 50 times or less, or 30 times or less.

The film may contain a compound other than the compound represented by the general formula (1) and the compound represented by the general formula (2). For example, the compound used as a host material in the light emitting layer of an organic light emitting element may be contained. As specific material examples, reference can be made to compound examples that can be used as a host material described later. The content in the film of a compound other than the compound represented by the general formula (1) and the compound represented by the general formula (2) and used as the host material is represented by the general formula (1). The total weight of the compound and the compound represented by the general formula (2) can be, for example, 1 or more times, 2 or more times, or 3 or more times, for example, 100 times or less, or 10 times It can be made below or 5 times or less.
The film of the present invention can emit light from the film by being irradiated with appropriate excitation light or energized by being sandwiched between a pair of electrodes. The light emission may be mainly light emission from the compound represented by the general formula (2), or may be light emission from another light emitting material that can be present in the film. As used herein, “mainly” means light emission from a light-emitting component that accounts for more than 50% of the total light emission from the film. Light emission from the light-emitting component that mainly emits light can be more than 70%, 90%, or 99% of the total light emission. Examples of the light emitting material other than the compounds represented by the general formula (1) and the general formula (2) include quantum dots, other inorganic light emitting materials, and organic light emitting materials. When a light emitting material other than the compound represented by the general formula (1) or the general formula (2) is contained in the film, the content of the light emitting material is a compound represented by the general formula (2). For example, it can be set to 0.00001 times or more, 0.0001 times or more, 0.001 times or more, 0.01 times or more, or 2 times or less, or 1 time or less. Or 0.5 times or less, or 0.1 times or less.

When light is emitted mainly from the compound represented by the general formula (2), the emission peak wavelength is the emission peak wavelength from the film excluding the compound represented by the general formula (2) [that is, represented by the general formula (1). Longer than the emission peak wavelength from the compound obtained. The difference between the emission peak wavelengths can be, for example, 30 nm or more, 60 nm or more, 90 nm or more, 250 nm or less, 200 nm or less, or 150 nm or less. The emission peak wavelength can be, for example, 480 nm or more, 510 nm or more, 530 nm or more, 700 nm or less, 650 nm or less, or 600 nm or less.
When other light emitting materials are contained in the film and light is emitted mainly from the light emitting material, the light emission peak wavelength is the light emission peak wavelength from the film excluding the light emitting material [that is, represented by the general formula (2) Longer than the peak emission wavelength from the compound]. The difference in emission peak wavelength can be, for example, 10 nm or more, 30 nm or more, 60 nm or more, 250 nm or less, 200 nm or less, or 150 nm or less. The emission peak wavelength can be, for example, 500 nm or more, 600 nm or more, 650 nm or more, 800 nm or less, 750 nm or less, or 700 nm or less.

  The thickness of the film of the present invention can be, for example, 0.1 nm or more, 1 nm or more, 5 nm or more, 10 nm or more, 100 nm or less, 50 nm or less, or 30 nm or less. Can be.

  The method for producing the film of the present invention is not particularly limited. For example, the film may be formed by co-evaporating each component constituting the film from different vapor deposition sources, or the film may be formed by drying after applying a solution in which each component constituting the film is dissolved in a solvent. May be formed. As the solvent, for example, toluene, hexane, a halogen solvent, an alcohol solvent, water, or the like can be used. In order to make it easy to dissolve in a solvent, for example, as a compound represented by the general formula (2), an alkyl group having 4 or more carbon atoms, an alkyl group having 6 or more carbon atoms, or an alkyl group having 8 or more carbon atoms is used. The compound which has is preferably employable. Coating methods include inkjet method, spin coating method, casting method, spray coating method, blade coating method, air knife coating method, wire bar coating method, gravure coating method, flexo coating method, reverse coating method, reverse roll coating method Further, an extrusion coating method, a screen method, a microcontact method, a dip coating method, a SAM (Self-assembled Monolayer) method, and the like can be appropriately selected and employed.

[Organic light emitting device]
The present invention provides an organic light emitting device comprising a compound represented by the general formula (1) and a compound represented by the general formula (2). The compound represented by general formula (1) and the compound represented by general formula (2) may be contained in the same layer or in different layers (for example, adjacent layers). The case where the compound represented by the general formula (1) and the compound represented by the general formula (2) are contained in the same layer is preferable. The organic light-emitting device of the present invention can be employed as a layer and a method for forming the layer. The layer containing the compound represented by the general formula (1) and the compound represented by the general formula (2) can be, for example, a light emitting layer. Alternatively, the layer containing the compound represented by the general formula (1) and the compound represented by the general formula (2) can be a layer adjacent to the light emitting layer (for example, a layer containing quantum dots). .
The organic light emitting device of the present invention may emit light mainly from a compound represented by the general formula (2), or a light emitting material other than the compound represented by the general formula (1) or the general formula (2). It may be one that mainly emits light. Examples of the light emitting material other than the compounds represented by the general formula (1) and the general formula (2) include quantum dots, other inorganic light emitting materials, and organic light emitting materials. The compound represented by the general formula (1) can transfer energy to the general formula (2) and other light-emitting materials, but for light emission from the organic light-emitting device of the present invention, the general formula (1) Luminescence from the represented compound may be included. The light emission from the compound represented by the general formula (1) is, for example, less than 20%, less than 10%, less than 5%, less than 1%, or less than 1% of the total light emission from the organic light emitting device. Or less than 1%. Further, even when light is emitted mainly from a light emitting material other than the compound represented by the general formula (1) or (2), light emission from the compound represented by the general formula (2) is included. Also good. The light emission from the compound represented by the general formula (2) is, for example, less than 20%, less than 10%, less than 5%, less than 1%, or less than 1% of the total light emission from the organic light emitting device. Or less than 1%.
Among the compounds represented by the general formula (1), there are compounds that can emit delayed fluorescence. For this reason, the organic light emitting device of the present invention can be configured to emit delayed fluorescence. Delayed fluorescence has a slower decay and longer emission lifetime than normal fluorescence. The emission lifetime of delayed fluorescence may be, for example, 0.05 μs or longer, 0.2 μs or longer, or 0.5 μs or longer.

The organic light-emitting device of the present invention can be provided as an organic photoluminescence device (organic PL device) or an organic electroluminescence device (organic EL device). The organic photoluminescence element has a structure in which at least a light emitting layer is formed on a substrate. The organic electroluminescence element has a structure in which an organic layer is formed at least between an anode, a cathode, and an anode and a cathode. The organic layer includes at least a light emitting layer, and may consist of only the light emitting layer, or may have one or more organic layers in addition to the light emitting layer. Examples of such other organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. The hole transport layer may be a hole injection / transport layer having a hole injection function, and the electron transport layer may be an electron injection / transport layer having an electron injection function. A specific example of the structure of an organic electroluminescence element is shown in FIG. In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, 6 is an electron transport layer, and 7 is a cathode.
Below, each member and each layer of an organic electroluminescent element are demonstrated. In addition, description of a board | substrate and a light emitting layer corresponds also to the board | substrate and light emitting layer of an organic photoluminescent element.

(substrate)
The organic electroluminescence device of the present invention is preferably supported on a substrate. The substrate is not particularly limited and may be any substrate conventionally used for organic electroluminescence elements. For example, a substrate made of glass, transparent plastic, quartz, silicon, or the like can be used.

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

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

(Light emitting layer)
The light emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons injected from each of the anode and the cathode, and the light emitting material may be used alone for the light emitting layer. , Preferably including a luminescent material and a host material. In the present invention, for example, a compound represented by the general formula (1) can be used as a host material, and a compound represented by the general formula (2) can be used as a light emitting material (dopant). Further, a host material other than the compound represented by the general formula (1) or the general formula (2) is used, and the compound represented by the general formula (1) is used as the first dopant (assist dopant). A compound represented by the formula (2) can also be used as the second dopant (light emitting material). Further, the compound represented by the general formula (1) is used as a host material, the compound represented by the general formula (2) is used as a first dopant (assist dopant), and another compound is second. It can also be used as a dopant (light emitting material). Alternatively, quantum dots or other inorganic materials or organic materials are employed as the light emitting material in the light emitting layer, and the compound represented by the general formula (1) or the general formula (2) is present in a layer adjacent to the light emitting layer. You can also.
When a host material is used in addition to the compound represented by the general formula (1) or the general formula (2), such a host material has at least one of excited singlet energy and excited triplet energy represented by the general formula ( It is preferable to use an organic compound having a higher value than the compound represented by 1) or general formula (2). As a result, singlet and triplet excitons generated in the compounds represented by general formula (1) and general formula (2) can be confined in the molecule, and the light emission efficiency can be sufficiently extracted. Is possible. However, even if singlet excitons and triplet excitons cannot be sufficiently confined, there are cases where high luminous efficiency can be obtained, so that host materials that can achieve high luminous efficiency are particularly limited. And can be used in the present invention. The light emission from the organic light emitting device of the present invention may include light emission from the host material.
For the content of the compound represented by the general formula (1), the compound represented by the general formula (2), and other materials in the light emitting layer, refer to the description of the content of each compound or material in the above film. can do.
As the host material in the light-emitting layer, it is preferable to use an organic compound that has a hole-transporting ability and an electron-transporting ability, prevents the emission of light from becoming longer, and has a high glass transition temperature.

(Injection layer)
The injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission. There are a hole injection layer and an electron injection layer, and between the anode and the light emitting layer or the hole transport layer. Further, it may be present between the cathode and the light emitting layer or the electron transport layer. The injection layer can be provided as necessary.

(Blocking layer)
The blocking layer is a layer that can prevent diffusion of charges (electrons or holes) and / or excitons existing in the light emitting layer to the outside of the light emitting layer. The electron blocking layer can be disposed between the light emitting layer and the hole transport layer and blocks electrons from passing through the light emitting layer toward the hole transport layer. Similarly, a hole blocking layer can be disposed between the light emitting layer and the electron transporting layer to prevent holes from passing through the light emitting layer toward the electron transporting layer. The blocking layer can also be used to block excitons from diffusing outside the light emitting layer. That is, each of the electron blocking layer and the hole blocking layer can also function as an exciton blocking layer. The term “electron blocking layer” or “exciton blocking layer” as used herein is used in the sense of including a layer having the functions of an electron blocking layer and an exciton blocking layer in one layer.

(Hole blocking layer)
The hole blocking layer has a function of an electron transport layer in a broad sense. The hole blocking layer has a role of blocking holes from reaching the electron transport layer while transporting electrons, thereby improving the recombination probability of electrons and holes in the light emitting layer. As the material for the hole blocking layer, the material for the electron transport layer described later can be used as necessary.

(Electron blocking layer)
The electron blocking layer has a function of transporting holes in a broad sense. The electron blocking layer has a role to block electrons from reaching the hole transport layer while transporting holes, thereby improving the probability of recombination of electrons and holes in the light emitting layer. .

(Exciton blocking layer)
The exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. It becomes possible to efficiently confine in the light emitting layer, and the light emission efficiency of the device can be improved. The exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously. That is, when the exciton blocking layer is provided on the anode side, the layer can be inserted adjacent to the light emitting layer between the hole transport layer and the light emitting layer, and when inserted on the cathode side, the light emitting layer and the cathode Between the luminescent layer and the light-emitting layer. Further, a hole injection layer, an electron blocking layer, or the like can be provided between the anode and the exciton blocking layer adjacent to the anode side of the light emitting layer, and the excitation adjacent to the cathode and the cathode side of the light emitting layer can be provided. Between the child blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, and the like can be provided. When the blocking layer is disposed, at least one of the excited singlet energy and the excited triplet energy of the material used as the blocking layer is preferably higher than the excited singlet energy and the excited triplet energy of the light emitting material.

(Hole transport layer)
The hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
The hole transport material has any one of hole injection or transport and electron barrier properties, and may be either organic or inorganic. Known hole transport materials that can be used include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, Examples include amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers. An aromatic tertiary amine compound and an styrylamine compound are preferably used, and an aromatic tertiary amine compound is more preferably used.

(Electron transport layer)
The electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
The electron transport material (which may also serve as a hole blocking material) may have a function of transmitting electrons injected from the cathode to the light emitting layer. Examples of the electron transport layer that can be used include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide oxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like. Furthermore, in the above oxadiazole derivative, a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material. Furthermore, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.

  When producing an organic electroluminescence element, the compound represented by the general formula (1) or the general formula (2) may be used not only for one organic layer but also for a plurality of organic layers. In that case, the compounds represented by the general formula (1) and the general formula (2) used for each organic layer may be the same or different from each other.

  Below, the preferable material which can be used for an organic electroluminescent element is illustrated concretely. However, the material that can be used in the present invention is not limited to the following exemplary compounds. Moreover, even if it is a compound illustrated as a material which has a specific function, it can also be diverted as a material which has another function.

First, preferred compounds that can also be used as a host material for the light emitting layer are listed.

A quantum dot that can be employed in the light emitting layer will be described. Quantum dots are nano-sized semiconductor particles having a quantum confinement effect. The band gap value of the quantum dot can be controlled by adjusting the constituent material type and particle diameter of the quantum dot. For this reason, there is an advantage that it is easy to prepare quantum dots that emit light in a desired wavelength region. As a result, the target emission chromaticity can be realized without using a color filter, so that high efficiency can be realized. The diameter of the quantum dots that can be used in the present invention is preferably 2 to 10 nm, more preferably 4 to 8 nm, and even more preferably 5 to 6 nm.
The constituent material type of the quantum dot is not particularly limited. Usually, quantum dots composed of one or more elements selected from Groups 14 to 16 of the periodic table can be preferably used. For example, it may be a simple substance composed of a single element such as C, Si, Ge, Sn, P, Se, or Te, or may be a compound composed of two or more elements. The quantum dots composed of two or more _{elements, SiC, SnO 2, Sn (} II) Sn (IV) S 3, SnS 2, SnS, SnSe, SnTe, PbS, PbSe, PbTe, BN, BP, BAs, AlN , AlP, AlAs, AlSb, GaN , GaP, GaAs, GaSb, InN, InP, InAs, InSb, Al 2 S 3, Al 2 Se 3, Ga 2 S 3, Ga 2 Se 3, Ga 2 Te 3, In 2 O ₃ , In ₂ S ₃ , In ₂ Se ₃ , In ₂ Te ₃ , TlCl, TlBr, TlI, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS), CdSe, CdTe, HgS, HgSe, HgTe, As ₂ S ₃ , As ₂ Se ₃ , As ₂ Te ₃ , Sb ₂ S ₃ , Sb ₂ Se ₃ , Sb ₂ Te ₃ , Bi ₂ S ₃ , Bi ₂ Se ₃ , Bi ₂ Te ₃ , Cu ₂ O, Cu ₂ Se , CuCl, CuBr, CuI, AgCl, AgBr, NiO, CoO, CoS, Fe ₃ O ₄ , FeS, MnO, MoS ₂ , WO ₂ , VO, VO ₂ , Ta ₂ O ₅ , TiO ₂ , Ti ₂ O ₅ , _{Ti 2 O 3, Ti 5 O} 9, MgS, MgSe, mention may be made of _{CdCr 2 O 4, CdCr 2 Se} 4, CuCr 2 S 4, HgCr 2 Se 4, BaTiO 3. Moreover, these can also be mixed and used. Among the above examples, CdSe, ZnSe, CdS, and CdSeS / ZnS can be preferably used. In the present invention, commercially available quantum dots can also be used. For example, model numbers 753785 and 753742 manufactured by Aldorich can be preferably used.
The quantum dot used in the present invention may have a surface coated.
The quantum dots can be formed by a method such as spin coating using a solution dissolved in an appropriate solvent. As the solvent, for example, toluene, hexane, a halogen solvent, an alcohol solvent, water, or the like can be used.

  Next, examples of preferable compounds that can be used as the hole injection material will be given.

  Next, examples of preferred compounds that can be used as a hole transport material are listed.

  Next, examples of preferable compounds that can be used as an electron blocking material are given.

  Next, preferred compound examples that can be used as a hole blocking material are listed.

  Next, examples of preferable compounds that can be used as an electron transporting material will be given.

  Next, examples of preferable compounds that can be used as the electron injection material are given.

  Furthermore, preferable compound examples are given as materials that can be added. For example, adding as a stabilizing material can be considered.

The organic light emitting device of the present invention can be a white light emitting device. By using a white light emitting element, it can be used as, for example, a lighting device or a backlight. In order to obtain a white light emitting element, it is preferable that two or more kinds of light emitting materials are used to simultaneously emit two or more kinds of light emitting colors to achieve white light emission by color mixing. As a combination of two or more kinds of luminescent colors, for example, three primary colors of blue, green, and red, and a combination of two colors that are complementary to each other can be exemplified. Examples of complementary colors include blue and yellow, blue green and orange, and the like. By using two or more kinds of light emitting materials that emit two or more kinds of luminescent colors in the organic light emitting element of the present invention, a white light emitting element can be obtained.
Two or more kinds of light emitting materials may coexist in a single light emitting layer, or may exist individually in different light emitting layers. For example, in the case of using three types of light emitting materials of a blue light emitting material, a green light emitting material, and a red light emitting material, a blue light emitting material layer, a green light emitting material layer, and a red light emitting material layer may be provided. At this time, each light emitting layer may be laminated | stacked, and may be arrange | positioned in parallel in the same plane. For example, in the case of a blue light emitting material layer, a green light emitting material layer, and a red light emitting material layer, these layers may be laminated, or a blue light emitting material layer region, a green light emitting material layer region, and a red light emitting material in the same plane. The material layer regions may be arranged in parallel in an array. In the case of being laminated, the blue light emitting material layer, the green light emitting material layer, and the red light emitting material layer may be laminated so as to contact each other in any order, or may be laminated with another layer interposed therebetween. Good.
As a specific configuration example of the white light emitting element, for example, the configuration example described in FIG. 1 and FIG. 8 of JP-A-2006-149368, or the specific configuration example described in each embodiment (paragraph 0044). To 0079 and paragraphs 0129 to 0133); configuration examples described in FIG. 1 of JP2015-32582A, specific configuration examples described in each embodiment; The structural example described in FIG. 1 of the gazette and the specific structural example described in each Example can be given. In the light-emitting layer such as the yellow-green light-emitting layer in these specific examples, by constituting as a layer containing the compound represented by the general formula (1) and the compound represented by the general formula (2) of the present invention, It can be set as a white light emitting element.

  The organic electroluminescence device produced by the above-described method emits light by applying an electric field between the anode and the cathode of the obtained device. At this time, if the light is emitted by excited singlet energy, light having a wavelength corresponding to the energy level is confirmed as fluorescence emission and delayed fluorescence emission. In addition, in the case of light emission by excited triplet energy, a wavelength corresponding to the energy level is confirmed as phosphorescence. Since normal fluorescence has a shorter fluorescence lifetime than delayed fluorescence, the emission lifetime can be distinguished from fluorescence and delayed fluorescence.

  On the other hand, with regard to phosphorescence, in ordinary organic compounds such as the compounds of the present invention, the excited triplet energy is unstable, the thermal deactivation rate constant is large, and the luminescence rate constant is small. Therefore, it is hardly observable at room temperature. In order to measure the excited triplet energy of a normal organic compound, it can be measured by observing light emission under extremely low temperature conditions.

  The organic electroluminescence element of the present invention can be applied to any of a single element, an element having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix. According to the present invention, by using the compound represented by the general formula (1) and the compound represented by the general formula (2), an organic light emitting device with improved luminous efficiency and driving life can be obtained. The organic light emitting device such as the organic electroluminescence device of the present invention can be further applied to various uses. For example, it is possible to produce an organic electroluminescence display device using the organic electroluminescence element of the present invention. For details, see “Organic EL Display” (Ohm Co., Ltd.) written by Shizushi Tokito, Chiba Adachi and Hideyuki Murata. ) Can be referred to. In particular, the organic electroluminescence device of the present invention can be applied to organic electroluminescence illumination and backlights that are in great demand.

  The features of the present invention will be described more specifically with reference to synthesis examples and examples. The following materials, processing details, processing procedures, and the like can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. Note that the evaluation of the light emission characteristics is as follows: source meter (manufactured by Keithley: 2400 series), semiconductor parameter analyzer (manufactured by Agilent Technologies: E5273A), optical power meter measuring device (manufactured by Newport: 1930C), optical spectrometer (Ocean Optics Co., Ltd .: USB2000), spectroradiometer (Topcon Co., Ltd .: SR-3), and streak camera (Hamamatsu Photonics Co., Ltd. model C4334) were used.

(Synthesis Example) Synthesis of Compound 1108 (1) Synthesis of Intermediate 1

Under a nitrogen stream, a dichloromethane solution (150 mL) of aluminum chloride (18.6 g, 139.4 mmol) was cooled to 0 ° C., and 2-ethylhexanoyl chloride (22.67 g, 139.4 mmol) was added dropwise. After stirring at 0 ° C. for 20 minutes, 9H-carbazole (10.0 g, 59.8 mmol) was added at the same temperature. The cooling bath was removed, and the mixture was stirred for 20 hours while gradually returning to room temperature. The reaction mixture was quenched with ice water, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting crude product was washed with hexane to obtain a white solid intermediate 1 (yield 22.36 g, 53.29 mmol, yield 89.4%).
¹ H-NMR (500 MHz, CDCl ₃ , δ): 8.81 (d, J = 1.5 Hz, 2H), 8.54 (s, 1H), 8.16 (dd, J = 8.5 Hz, 1 .5Hz, 2H) 7.51 (d, J = 8.5 Hz, 2H), 3.58-3.53 (m, 2H), 1.92-1.82 (m, 4H), 1.69- 1.58 (m, 4H), 1.35 to 1.27 (m, 8H), 0.94 (t, J = 7.5 Hz, 6H), 0.88-0.85 (m, 6H)
ASAP mass spectral analysis: theoretical value 419.2, observed value 419.2

(2) Synthesis of intermediate 2

Under a nitrogen stream, a tetrahydrofuran solution (250 mL) of aluminum chloride (3.18 g, 23.82 mmol) was cooled to 0 ° C., and lithium aluminum hydride (1.81 g, 47.6 mmol) was added. Under the same temperature, a tetrahydrofuran solution (25 mL) of intermediate 1 (5.0 g, 11.91 mmol) was added dropwise and stirred for 10 minutes. The cooling bath was removed, and the mixture was stirred for 72 hours while gradually returning to room temperature. This reaction mixture was quenched by adding ice water, extracted with ethyl acetate, the organic layer was washed with 10% hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting mixture was purified by silica gel column chromatography (toluene: hexane = 1: 2) to give a white liquid intermediate 2 (4.52 g, 11.54 mmol, yield 97.0%). Got.
¹ H-NMR (500 MHz, CDCl ₃ , δ): 7.84 (s, 1H), 7.81 (d, J = 1.5 Hz, 2H), 7.30 (d, J = 8.5 Hz, 2H) ), 7.18 (dd, J = 8.5 Hz, 1.5 Hz, 2H), 2.73-2.65 (m, 4H), 1.68-1.61 (m, 2H), 1.39 -1.25 (m, 16H), 0.92-0.87 (m, 12
H)
ASAP mass spectral analysis: theoretical value 391.3, observed value 391.3

(3) Synthesis of Compound 1108

Under a nitrogen stream, a tetrahydrofuran solution (5 mL) of intermediate 2 (1.8 g, 4.60 mmol) was added dropwise to a tetrahydrofuran solution (20 mL) of sodium hydride (60% in oil, 0.22 g, 5.52 mmol). . After stirring at room temperature for 30 minutes, tetrafluoroisophthalonitrile (0.184 g, 0.92 mmol) was added and stirred for 18 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride, extracted from ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting mixture was purified by silica gel column chromatography (toluene: hexane = 1: 10) to give pale yellow liquid compound 1108 (1.45 g, 0.86 mmol, yield 93.5%). Got.
¹ H-NMR (500 MHz, CDCl ₃ , δ): 7.94 (d, J = 1.5 Hz, 2H), 7.59 (d, J = 8.5 Hz, 2H) 7.47 (dd, J = 8.5 Hz, 1.5 Hz, 2H), 7.39-7.34 (m, 4H), 7.27-7.24 (m, 4H), 7.18-7.16 (m, 4H) 6 .96 (s, 2H), 6.48 (d, J = 8.5 Hz, 2H), 6.25 (d, J = 8.5 Hz, 2H), 2.82-2.74 (m, 4H) 2.57-2.37 (m, 10H), 2.27-2.22 (m, 2H), 1.77-1.72 (m, 2H), 1.50-1.07 (m, 70H), 0.97-0.81 (m, 48H)
ASAP mass spectral analysis: theoretical value 1685.3, observed value 1685.7

Example 1 Formation of Film by Inkjet Method 79 mg of mCBP, 20 mg of compound 304 (4CzIPN-Me) and 1 mg of compound 2097 (TBRb) were prepared, and these were dissolved in 10 mL of toluene to prepare a solution. Each compound was completely dissolved in the solvent. A film is formed by spraying the solution onto a glass substrate by an inkjet method and drying.

(Example 2) Formation of film by spin coating method The solution prepared in Example 1 is spin-coated on a glass substrate and dried to form a film.

(Example 3) Production 1 of an organic electroluminescence element by an inkjet method
Instead of the light emitting layer in Example 1 of Japanese Patent No. 4203470, a light emitting layer is formed by the ink jet method using the solution prepared in Example 1, and the other procedures are the same as in Example 1 of the same publication. An electroluminescence element is manufactured. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

(Example 4) Preparation 2 of an organic electroluminescence element by an ink jet method
Instead of the light emitting layer in Example 2 of Japanese Patent No. 4203470, a light emitting layer is formed by the ink jet method using the solution prepared in Example 1, and the other procedures are the same as in Example 2 of the same publication. An electroluminescence element is manufactured. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

(Example 5) Production 3 of organic electroluminescence element by ink jet method
Instead of the light emitting layer in Example 3 of Japanese Patent No. 4203470, a light emitting layer is formed by the ink jet method using the solution prepared in Example 1, and the other procedures are the same as in Example 3 of the same publication. An electroluminescence element is manufactured. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

(Example 6) Production and evaluation of organic electroluminescence device Each thin film was vacuum-deposited on a glass substrate on which an anode made of indium tin oxide (ITO) having a film thickness of 100 nm was formed by a vacuum deposition method. Lamination was performed at 4 × 10 ⁻⁴ Pa. First, HATCN was formed on ITO with a thickness of 10 nm, and TrisPCz was formed thereon with a thickness of 20 nm, and further mCBP was formed thereon with a thickness of 10 nm. Subsequently, mCBP, compound 304 (4CzIPN-Me), and compound 2097 (TBRb) were co-evaporated from different deposition sources to form a light-emitting layer having a thickness of 30 nm. At this time, the concentration of compound 304 (4CzIPN-Me) was 25 wt%, and the concentration of compound 2097 (TBRb) was 0.5 wt%. Next, T2T was formed to a thickness of 10 nm, and BPyTP2 was formed thereon to a thickness of 55 nm. Furthermore, Liq was formed to a thickness of 1 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, whereby an organic electroluminescence element was obtained.
The manufactured organic electroluminescence device had a luminance of 1000 cd / m ² at 5.42 V and 2.59 mA / cm ² . The maximum external quantum efficiency was as high as 12.2%, the peak wavelength was 563 nm, the chromaticity coordinate x in the CIE-XYZ color system was 0.46, and y was 0.53. Further, when a life test was performed, the time until the luminance became 95% was 1060 hours.

Example 7 Production 1 of White Light Emitting Element
In place of Alq3 and dopant (C545T) in the light emitting layer described in paragraph 0054 of JP-T-2007-533073, mCBP (74.5% by weight), compound 304 (4CzIPN-Me) (25% by weight) and compound 2097 A light emitting layer is formed using (TBRb) (0.5% by weight), and other procedures are performed in the same manner as in the example including paragraph 0054 of the same publication, and an organic electroluminescence device is manufactured. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

Example 8 Production 2 of White Light Emitting Element
Instead of Alq3 and dopant (C545T) in the light-emitting layer described in paragraph 0054 of JP2012-18931A, mCBP (74.5 wt%), compound 304 (4CzIPN-Me) (25 wt%), and compound 2097 A light emitting layer is formed using (TBRb) (0.5% by weight), and other procedures are performed in the same manner as in the example including paragraph 0054 of the publication, and an organic electroluminescent device is manufactured. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

Example 9 Production 3 of White Light Emitting Element
In place of Alq3 and dopant (C545T) in the light emitting layer described in paragraph 0054 of JP-A-2014-179344, mCBP (74.5% by weight), Compound 304 (4CzIPN-Me) (25% by weight) and Compound 2097 A light emitting layer is formed using (TBRb) (0.5% by weight), and other procedures are performed in the same manner as in the example including paragraph 0054 of the same publication, and an organic electroluminescence device is manufactured. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

Example 10 Production of White Light Emitting Element 4
Chemical formula (7) using mCBP (74.5% by weight) instead of the material of chemical formula (6) used as the host of the light emitting layer described in paragraph 0077 of JP-A-2015-130335 and using as the dopant The light emitting layer is formed using Compound 304 (4CzIPN-Me) (25 wt%) and Compound 2097 (TBRb) (0.5 wt%) in place of the above materials, and other procedures include paragraph 0077 of the same publication. An organic electroluminescence element is produced in the same manner as in the example. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

Example 11 Production 5 of White Light Emitting Element
Instead of the constituent material of the yellow-green light emitting layer described in paragraph 0068 of JP-A-2015-32582, mCBP (74.5% by weight), Compound 304 (4CzIPN-Me) (25% by weight) and Compound 2097 (TBRb ) (0.5 wt%) is used to form a layer, and other procedures are performed in the same manner as in Example 1-1 to produce an organic electroluminescent device. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

Example 12 Production of White Light Emitting Element 6
Instead of the constituent material of the yellow-green light emitting layer described in paragraph 0106 of JP-A-2015-32582, mCBP (74.5% by weight), compound 304 (4CzIPN-Me) (25% by weight) and compound 2097 (TBRb ) (0.5 wt%) is used to form a layer, and other procedures are performed in the same manner as in Example 8-1 of the same publication to produce an organic electroluminescent element. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

Example 13 Production of White Light Emitting Element 7
The light emitting layer 145 shown in FIG. 1 referred to in paragraphs [0047] to [0048] of JP-A-2016-149368 includes mCBP (74.5% by weight), compound 304 (4CzIPN-Me) (25% by weight), and a compound. A layer is formed using 2097 (TBRb) (0.5% by weight), and the others are prepared according to the description in the publication. This organic electroluminescence device has a high maximum external quantum efficiency and a long lifetime.

The compounds 304 (4CzIPN-Me) used in Example 1 above were used in the same manner as in Example 1 except that Compounds 1 to 303 and 305 to 1367 represented by the above general formula (1) were used. The membranes are disclosed herein as membranes 1a-303a, 305a-1367a.
The compounds 304 (4CzIPN-Me) used in Example 2 above were used in the same manner as in Example 2 except that Compounds 1 to 303 and 305 to 1367 represented by the above general formula (1) were used. The membranes are disclosed herein as membranes 1b-303b, 305b-1367b.
The compound 304 (4CzIPN-Me) used in Example 3 was prepared in the same manner as in Example 3, except that the compounds 1 to 303 and 305 to 1367 represented by the general formula (1) were used. Organic electroluminescent elements are disclosed herein as elements 1c-303c, 305c-1367c.
It manufactured by the same method as Example 4 using the compounds 1-303 and 305-1367 represented by the said General formula (1) instead of the compound 304 (4CzIPN-Me) used in the said Example 4, respectively. Organic electroluminescent elements are disclosed herein as elements 1d-303d, 305d-1367d.
The compounds 304 (4CzIPN-Me) used in Example 5 above were used in the same manner as in Example 5 except that compounds 1 to 303 and 305 to 1367 represented by the above general formula (1) were used. Organic electroluminescent elements are disclosed herein as elements 1e-303e, 305e-1367e.
Prepared by the same method as in Example 6, using compounds 1 to 303 and 305 to 1367 represented by general formula (1) instead of compound 304 (4CzIPN-Me) used in Example 6 above. Organic electroluminescent elements are disclosed herein as elements 1f-303f, 305f-1367f.
Prepared by the same method as in Example 7, using compounds 1 to 303 and 305 to 1367 represented by general formula (1) instead of compound 304 (4CzIPN-Me) used in Example 7 above. White light emitting elements are disclosed herein as elements 1g-303g, 305g-1367g.
Prepared by the same method as in Example 8, using compounds 1 to 303 and 305 to 1367 represented by the above general formula (1) instead of the compound 304 (4CzIPN-Me) used in Example 8 above. White light emitting elements are disclosed herein as elements 1h-303h, 305h-1367h.
Prepared by the same method as in Example 9, using compounds 1 to 303 and 305 to 1367 represented by general formula (1) instead of compound 304 (4CzIPN-Me) used in Example 9 above. White light emitting elements are disclosed herein as elements 1i-303i, 305i-1367i.
The compound 304 (4CzIPN-Me) used in Example 10 was prepared in the same manner as in Example 10 except that the compounds 1 to 303 and 305 to 1367 represented by the general formula (1) were used. White light emitting elements are disclosed herein as elements 1j-303j, 305j-1367j.
Prepared by the same method as in Example 11 using compounds 1 to 303 and 305 to 1367 represented by the general formula (1) instead of the compound 304 (4CzIPN-Me) used in Example 11 above. White light emitting elements are disclosed herein as elements 1k-303k, 305k-1367k.
Prepared by the same method as in Example 12 except that compounds 1 to 303 and 305 to 1367 represented by the above general formula (1) were used instead of the compound 304 (4CzIPN-Me) used in Example 12 above. White light emitting elements are disclosed herein as elements 1l-303l, 305l-1367l.
Prepared by the same method as in Example 13, except that compounds 1 to 303 and 305 to 1367 represented by the above general formula (1) were used instead of the compound 304 (4CzIPN-Me) used in Example 13 above. White light emitting elements are disclosed herein as elements 1m-303m, 305m-1367m.

A film produced by the same method as in Example 1, except that the compounds 2001 to 2096 and 2098 to 2442 represented by the general formula (2) are used instead of the compound 2097 (TBRb) used in the above Example 1. , Membranes 2001a-2096a, 2098a-2442a.
A film produced by the same method as in Example 2 using compounds 2001 to 2096 and 2098 to 2442 represented by the general formula (2) instead of the compound 2097 (TBRb) used in Example 2 above. , Membranes 2001b-2096b, 2098b-2442b.
Instead of the compound 2097 (TBRb) used in Example 3 above, the compounds 2001 to 2096 and 2098 to 2442 represented by the general formula (2) were used, respectively, and the organic electroluminescence produced by the same method as Example 3 was used. Luminescent elements are disclosed herein as elements 2001c-2096c, 2098c-2442c.
Instead of the compound 2097 (TBRb) used in Example 4 above, the compounds 2001 to 2096 and 2098 to 2442 represented by the above general formula (2) were used, respectively, and the organic electroluminescence produced by the same method as Example 4 was used. Luminescent elements are disclosed herein as elements 2001d-2096d, 2098d-2442d.
Instead of the compound 2097 (TBRb) used in the above Example 5, the compounds 2001 to 2096 and 2098 to 2442 represented by the general formula (2) were used, respectively, and the organic electroluminescence produced by the same method as Example 5 was used. Luminescent elements are disclosed herein as elements 2001e-2096e, 2098e-2442e.
Instead of the compound 2097 (TBRb) used in Example 6 above, the compounds 2001 to 2096 and 2098 to 2442 represented by the general formula (2) were used, respectively, and the organic electroluminescence produced by the same method as Example 6 was used. Luminescent elements are disclosed herein as elements 2001f-2096f, 2098f-2442f.
White light emission produced by the same method as in Example 7 using compounds 2001 to 2096 and 2098 to 2442 represented by general formula (2) instead of compound 2097 (TBRb) used in Example 7 above. The elements are disclosed herein as elements 2001g-2096g, 2098g-2442g.
White light emission produced by the same method as in Example 8 using compounds 2001 to 2096 and 2098 to 2442 represented by general formula (2) instead of compound 2097 (TBRb) used in Example 8 above. The elements are disclosed herein as elements 2001h-2096h, 2098h-2442h.
White light emission produced by the same method as in Example 9 using compounds 2001 to 2096 and 2098 to 2442 represented by general formula (2) instead of compound 2097 (TBRb) used in Example 9 above. The elements are disclosed herein as elements 2001i-2096i, 2098i-2442i.
White light emission produced by the same method as in Example 10 using compounds 2001 to 2096 and 2098 to 2442 represented by general formula (2) instead of compound 2097 (TBRb) used in Example 10 above. The elements are disclosed herein as elements 2001j-2096j, 2098j-2442j.
White light emission produced by the same method as in Example 11 using compounds 2001 to 2096 and 2098 to 2442 represented by general formula (2) instead of compound 2097 (TBRb) used in Example 11 above. The elements are disclosed herein as elements 2001k-2096k, 2098k-2442k.
White light emission produced by the same method as in Example 12 using compounds 2001 to 2096 and 2098 to 2442 represented by general formula (2) instead of compound 2097 (TBRb) used in Example 12 above. The elements are disclosed herein as elements 2001l-2096l, 2098l-2442l.
White light emission produced by the same method as in Example 13 using compounds 2001 to 2096 and 2098 to 2442 represented by general formula (2) instead of compound 2097 (TBRb) used in Example 13 above. The elements are disclosed herein as elements 2001m-2096m, 2098m-2442m.

Instead of HATCN used in Example 6 above, an organic electroluminescence device manufactured by the same method as in Example 6 using 8 compounds other than HATCN described above as those that can be used as a hole injection material Are disclosed herein as elements 1n-8n.
Instead of TrisPCz used in Example 6 above, 36 compounds except for TrisPCz described above that can be used as a hole transport material were used, respectively, and an organic electroluminescence device manufactured by the same method as in Example 6 Are disclosed herein as elements 1o-36o.
Instead of mCBP used in Example 6 above, 41 compounds other than the above-described mCBP that can be used as a host material were used, respectively, and an organic electroluminescence device produced by the same method as in Example 6 was used. It is disclosed here as elements 1p-41p.
An organic electroluminescence device manufactured by the same method as in Example 6 except that 10 compounds except T2T described above can be used as a hole blocking material instead of T2T used in Example 6 above. Are disclosed herein as elements 1q to 10q.
In place of BPyTP2 used in Example 6 above, 33 compounds except for BPyTP2 described above which can be used as an electron transport material, and LiF and CsF described above as those which can be used as an electron injection material 4 The organic electroluminescent element manufactured by the same method as Example 6 using each compound is disclosed here as element 1r-37r.

  The organic light-emitting device of the present invention can achieve high luminous efficiency and a long driving life. The compound of the present invention is useful as a light emitting material for such an organic light emitting device. For this reason, this invention has high industrial applicability.

DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Hole injection layer 4 Hole transport layer 5 Electron blocking layer 6 Light emitting layer 7 Electron transport layer 8 Cathode

Claims (16)

A film containing a compound represented by the following general formula (1) and a compound represented by the following general formula (2).

[In the general formula (1), at least one of R ¹ to R ⁵ represents a cyano group, at least one of R ¹ to R ⁵ represents a group represented by the following general formula (11), the remaining R ^{1 to} R ^{5 each} represents a hydrogen atom or a substituent (excluding a cyano group and a group represented by the general formula (11)). ]

[In General Formula (11), R ^{21 to} R ²⁸ each independently represents a hydrogen atom or a substituent. However, at least one of the following <A> or <B> is satisfied.
<A> R ²⁵ and R ²⁶ together form a single bond.
<B> R ²⁷ and R ²⁸ together represent an atomic group necessary for forming a substituted or unsubstituted benzene ring. ]

[In General Formula (2), R ¹ ′ to R ²⁸ ′ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or — It represents a group represented by Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′). R ²⁹ ′ to R ³¹ ′ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ] The manufacturing method of the film | membrane including the process of apply | coating the solution which melt | dissolved the compound represented by the following general formula (1), and the compound represented by the following general formula (2) in the organic solvent.

[In the general formula (1), at least one of R ¹ to R ⁵ represents a cyano group, at least one of R ¹ to R ⁵ represents a group represented by the following general formula (11), the remaining R ^{1 to} R ^{5 each} represents a hydrogen atom or a substituent (excluding a cyano group and a group represented by the general formula (11)). ]

[In General Formula (11), R ^{21 to} R ²⁸ each independently represents a hydrogen atom or a substituent. However, at least one of the following <A> or <B> is satisfied.
<A> R ²⁵ and R ²⁶ together form a single bond.
<B> R ²⁷ and R ²⁸ together represent an atomic group necessary for forming a substituted or unsubstituted benzene ring. ]

[In General Formula (2), R ¹ ′ to R ²⁸ ′ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or — It represents a group represented by Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′). R ²⁹ ′ to R ³¹ ′ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ]   The manufacturing method of the film | membrane of Claim 2 which performs the said application | coating by an inkjet system. An organic light emitting device comprising a compound represented by the following general formula (1) and a compound represented by the following general formula (2).

[In the general formula (1), at least one of R ¹ to R ⁵ represents a cyano group, at least one of R ¹ to R ⁵ represents a group represented by the following general formula (11), the remaining R ^{1 to} R ^{5 each} represents a hydrogen atom or a substituent (excluding a cyano group and a group represented by the general formula (11)). ]

[In General Formula (11), R ^{21 to} R ²⁸ each independently represents a hydrogen atom or a substituent. However, at least one of the following <A> or <B> is satisfied.
<A> R ²⁵ and R ²⁶ together form a single bond.
<B> R ²⁷ and R ²⁸ together represent an atomic group necessary for forming a substituted or unsubstituted benzene ring. ]

[In General Formula (2), R ¹ ′ to R ²⁸ ′ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or — It represents a group represented by Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′). R ²⁹ ′ to R ³¹ ′ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ]   The organic light emitting element of Claim 4 which contains the compound represented by the said General formula (1), and the compound represented by the said General formula (2) in the same layer. The organic light-emitting device according to claim 4 or 5, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1 ').

[In the general formula (1 ') at least one of R ^A1 to R ^A5 represents a cyano group, at least one of R ^A1 to R ^A5 represents a branched alkyl substituent carbazolyl group, the remaining R ^A1 to R ^A5 Represents a hydrogen atom or a substituent (excluding a cyano group and a branched alkyl-substituted carbazolyl group). ] In the general formula (2), at least one of R ² ′, R ⁶ ′, R ¹⁶ ′ and R ²¹ ′ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl The organic light-emitting device according to claim 4, which is a group or a group represented by —Si (R ²⁹ ′) (R ³⁰ ′) (R ³¹ ′). R ² ′, R ⁶ ′, R ¹⁶ ′ and R ²¹ ′ in the general formula (2) are all independently substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl group, a group represented by Matawa ^{Si (R 29 ') (R} 30') (R 31 '), an organic light-emitting device according to any one of claims 4-6.   The organic light emitting element of any one of Claims 4-8 which has a light emitting layer containing a quantum dot.   The organic light-emitting device according to any one of claims 4 to 9, which is an organic electroluminescence device.   The organic light-emitting device according to claim 4, which emits delayed fluorescence.   The illuminating device provided with the organic light emitting element of any one of Claims 4-11.   The lighting device according to claim 12, which emits white light.   The lighting device according to claim 12 or 13, which is a backlight. The compound represented by the following general formula (12 ').

In General formula (12 '), at least one of an acyl group or a branched alkyl group, the other R ^A31 to R ^A38 is a hydrogen atom or a substituent (wherein the acyl group and a branched alkyl group of R ^A31 to R ^A38 Is excluded). ] A compound represented by the following general formula (1 ′).

[In the general formula (1 ') at least one of R ^A1 to R ^A5 represents a cyano group, at least one of R ^A1 to R ^A5 represents a branched alkyl substituent carbazolyl group, the remaining R ^A1 to R ^A5 Represents a hydrogen atom or a substituent (excluding a cyano group and a branched alkyl-substituted carbazolyl group). ]

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