KR20200096506A - Arylamine compound and organic electroluminescence device - Google Patents

Abstract

Between the anode and the cathode, at least one of the layers disposed between the first hole transport layer and the electron transport layer, comprising at least a first hole transport layer, a second hole transport layer, a green light emitting layer, and an electron transport layer in this order from the anode side Silver is an organic EL device containing an arylamine compound represented by the following general formula (1).

Description

Arylamine compound and organic electroluminescence device

The present invention relates to a compound suitable for an organic electroluminescence device (hereinafter, abbreviated as an organic EL device), which is a self-luminous device suitable for various display devices, and to the device, and in particular, an arylamine compound and the compound It relates to the used organic EL device.

Since the organic EL device is a self-luminous device, it is brighter, has excellent visibility, and enables clear display compared to a liquid crystal device, and thus, active research has been conducted.

In 1987, Eastman-Kodak's CW Tangs developed a layered structure device in which various roles were assigned to each material, making organic EL devices using organic materials practical. They stack a phosphor capable of transporting electrons, tris(8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq ₃ ) and an aromatic amine compound capable of transporting holes, and inject both charges into the layer of the phosphor. By carrying out light emission, a high luminance of 1000 cc/m 2 or more was obtained at a voltage of 10 V or less (see, for example, Patent Document 1 and Patent Document 2).

To date, many improvements have been made for the practical use of organic EL devices, and various roles have been further subdivided to form an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode on the substrate sequentially. High efficiency and durability were achieved by one electroluminescent device (see, for example, Non-Patent Document 1).

In addition, for the purpose of further improving the luminous efficiency, the use of triplet excitons has been attempted, and the use of a phosphorescent light emitter has been studied (see, for example, Non-Patent Document 2).

The light-emitting layer can also be produced by doping a phosphor or a phosphorescent light-emitting body with a charge-transporting compound generally referred to as a host material. In recent years, a highly efficient organic EL device using an iridium complex as a phosphorescent light emitting material and a compound having a carbazole structure as a host material has been proposed (for example, Patent Document 3).

In addition, by using a compound having a nitrogen-containing heteroaromatic ring structure having a high electron transporting ability to a host and a compound having a carbazole structure having a hole-transporting function together, the transport of electrons and holes is higher and light emission compared to when used alone. The efficiency was remarkably improved (see, for example, Patent Document 4 and Patent Document 5).

As a hole-transporting material and a host material having hole-transporting ability that have been used in phosphorescent organic EL devices so far, carbazole derivatives (eg, HTM-1 below) shown in Patent Document 6 have been known. Carbazole derivatives have a high triplet energy level (hereinafter, abbreviated as T1) and are excellent in the ability to trap triplet excitons, but have low hole mobility and a problem in electrical reduction durability. Therefore, when combined with a light-emitting layer having improved electron transport ability, the supply of holes to the light-emitting layer is controlled at a rate, and the electrons are excessive in the light-emitting layer, and there is a concern of a decrease in luminous efficiency and a short lifespan in an organic EL device using these.

[Formula 1]

As an attempt to solve the above problems, Patent Document 7 proposes a monoamine compound represented by the following formula (for example, the following HTM-2) having excellent electrical durability and high hole transport ability. .

[Formula 2]

However, these monoamine compounds have a high hole mobility compared to the carbazole derivatives, but there is a problem with a low T1. For this reason, the triplet excitons are insufficiently confined, there is a concern that the luminous efficiency is lowered due to the inactivation of the excitons, and the life of the device is shortened. Therefore, a hole transport material and a host material having high hole mobility and excellent confinement of triplet excitons have been required.

Japanese Laid-Open Patent Publication No. Hei 8-048656 Japanese Laid-Open Patent Publication No. Hei 7-126615 Japanese Patent Application Publication No. 2006-151979 International Publication No. 2015/034125 International Publication No. 2016/013732 Japanese Laid-Open Patent Publication No. Hei 8-003547 Japanese Patent Application Publication No. 2006-352088 International Publication No. 2017/099155 Japanese Unexamined Patent Publication No. 2002-105055 International Publication No. 2014/007565 International Publication No. 2014/188947 International Publication No. 2015/190400 Japanese Unexamined Patent Publication No. 2010-83862 International Publication No. 2015/038503 Japanese Unexamined Patent Publication No. 2005-108804 International Publication No. 2008/62636 International Publication No. 2014/009310

Applied Physics Association 9th Class Preliminary Proceedings 55-61 pages (2001) Applied Physics Association 9th Class Preliminary Proceedings 23-31 pages (2001) Synth. Commun., 11, 513 (1981)

An object of the present invention is a material for an organic EL device with high efficiency and high durability, excellent in hole injection/transport performance, electron blocking ability, high stability in a thin film state, and excellent characteristics of high luminous efficiency. It is to provide an organic compound having and further use this compound to provide a highly efficient and highly durable organic EL device.

The physical properties of the organic compound to be provided by the present invention include (1) good hole injection characteristics, (2) high hole mobility, and (3) excellent electron blocking ability. , (4) the state of the thin film is stable, and (5) the durability against the former is excellent. In addition, physical characteristics that the organic EL device to be provided by the present invention must have include (1) high luminous efficiency and (2) long device life.

Therefore, in order to achieve the above object, the present inventors have anticipated that the aromatic tertiary amine structure has a high hole injection and transport ability, and the effect on electrical durability and thin film stability, the monoamine having a novel triarylamine structure Compounds were designed and chemically synthesized, and various organic EL devices were tested using the compounds, and the characteristics of the devices were intensively evaluated. As a result, the present invention was completed.

The organic EL device of the present invention capable of solving the above problems,

1) Between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a green light-emitting layer, and an electron transport layer are provided in this order from the anode side, and at least one of the layers disposed between the first hole transport layer and the electron transport layer One layer contains an arylamine compound represented by the following general formula (1).

[Chemical Formula 3]

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ may be the same or different, respectively, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation c Represents a cyclic aromatic group, and R ₁ , R ₂ , R ₃ may each be the same or different, and the number of carbon atoms from which each may have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a substituent is 1 to 6 linear or branched alkyl group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituent group A linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted A substituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

Another organic EL device of the present invention capable of solving the above problems,

2) Between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a green light emitting layer, and an electron transport layer are provided in this order from the anode side, and at least one of the layers disposed between the first hole transport layer and the electron transport layer One layer contains an arylamine compound represented by the following general formula (2).

[Formula 4]

(In the formula, Ar ₁ and Ar ₂ may be the same or different from each other, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and Ar ₅ and Ar ₆ may be the same or different from each other, and represent a phenyl group, a biphenylyl group, a naphthyl group, a phenanthrenyl group, or a fluorenyl group, and R ₄ is a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group , A nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, and 2 to carbon atoms which may have a substituent 6 linear or branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cycloalkyl oxy group having 5 to 10 carbon atoms which may have a substituent It represents a time period, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

Moreover, the arylamine compound of this invention which can solve the said subject is represented by following general formula (1).

[Formula 5]

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ may be the same or different, respectively, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation c Represents a cyclic aromatic group, and R ₁ , R ₂ , R ₃ may each be the same or different, and the number of carbon atoms from which each may have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a substituent is 1 to 6 linear or branched alkyl group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituent group A linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted A substituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

The arylamine compound of the present invention is useful as a light emitting layer of an organic EL device or a second hole transport layer adjacent to the light emitting layer, has excellent electron blocking ability, excellent durability against electrons, has good amorphous properties, and is in a thin film state. Is stable and excellent in heat resistance. The organic EL device of the present invention has high luminous efficiency and power efficiency, and can extend the life of the device by excellent durability against electrons.

1 is a diagram showing the configuration of EL elements in Examples 10 to 21 and Comparative Examples 1 to 6;

Hereinafter, an embodiment of the present invention will be described in detail. First, the arylamine compound and organic EL device of the present embodiment will be described by enumerating their aspects. In addition, in this application, the term "to" is a term indicating a range. For example, the description of "5-10" means "5 or more and 10 or less", and shows a range including the numerical value itself described before and after "to".

1) Between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a green light-emitting layer, and an electron transport layer are provided in this order from the anode side, and at least one of the layers disposed between the first hole transport layer and the electron transport layer One layer is an organic EL device containing an arylamine compound represented by the following general formula (1).

[Formula 6]

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ may be the same or different, respectively, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation c Represents a cyclic aromatic group, and R ₁ , R ₂ , R ₃ may each be the same or different, and the number of carbon atoms from which each may have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a substituent is 1 to 6 linear or branched alkyl group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituent group A linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted A substituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

2) Between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a green light emitting layer, and an electron transport layer are provided in this order from the anode side, and at least one of the layers disposed between the first hole transport layer and the electron transport layer One layer is an organic EL device containing an arylamine compound represented by the following general formula (2).

[Formula 7]

(In the formula, Ar ₁ and Ar ₂ may be the same or different from each other, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and Ar ₅ and Ar ₆ may be the same or different from each other, and represent a phenyl group, a biphenylyl group, a naphthyl group, a phenanthrenyl group, or a fluorenyl group, and R ₄ is a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group , A nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, and 2 to carbon atoms which may have a substituent 6 linear or branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cycloalkyl oxy group having 5 to 10 carbon atoms which may have a substituent It represents a time period, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

3) The green light-emitting layer includes a host and a phosphorescent dopant, and the host includes at least one type of first host compound represented by the following formula Host-A, and at least one type of the following formula Host-B. The organic EL device according to 1) or 2), comprising a second host compound.

[Formula 8]

(In the above Host-A, Z is each independently N or CRa, at least one of Z is N, and R ₅ to R ₁₄ and Ra are each independently a hydrogen atom, a deuterium atom, a fluorine atom, A chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms forming a ring, and a 6 atom substituted with a triphenylene group in Host-A The total number of rings is 6 or less, L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and n1 to n3 are each independently , 0 or 1, and n1 + n2 + n3 ≥ 1.)

[Formula 9]

(In Host-B, Y is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, and Ar ₇ is substituted Or an unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and R ₁₅ to R ₁₈ are each independently a hydrogen atom, a deuterium atom, or a fluorine atom , A chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 50 ring carbon atoms, At least one of R ₁₅ to R ₁₈ and Ar ₇ includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazolyl group.)

4) The organic EL device according to any one of 1) to 3) above, wherein the green light-emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex containing iridium.

5) The organic EL device according to any one of the above 1) to 3), wherein the green light-emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex represented by the following general formula (3).

[Formula 10]

(In the formula, R ₁₉ to R ₃₄ may each be the same or different, and a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent , A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a 1 to 6 carbon atom which may have a substituent A linear or branched alkyloxy group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a trimethylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group , A substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a disubstituted amino group substituted by a group selected from the group consisting of an aromatic hydrocarbon group, an aromatic heterocyclic group and a condensed polycyclic aromatic group n represents the integer of 1-3.)

6) The organic EL device according to any one of 1) to 5), wherein the electron transport layer contains a compound having a pyrimidine structure represented by the following general formula (4).

[Formula 11]

(In the formula, Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, and Ar ₉ and Ar ₁₀ may be the same as or different from each other, and a hydrogen atom, substituted or unsubstituted A substituted aromatic hydrocarbon group or a substituted or unsubstituted condensed polycyclic aromatic group is represented, and B represents a monovalent group represented by the following structural formula (5): Here, Ar ₉ and Ar ₁₀ do not simultaneously become hydrogen atoms. )

[Formula 12]

(In the formula, Ar ₁₁ represents a substituted or unsubstituted aromatic heterocyclic group, and R ₃₅ to R ₃₈ may be the same or different, respectively, and a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a tri A fluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group Show.)

7) The organic EL device according to any one of 1) to 5), wherein the electron transport layer contains a compound having a benzoazole structure represented by the following general formula (6).

[Formula 13]

(In the formula, Ar ₁₂ and Ar ₁₃ may be the same or different from each other, a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted Represents an aromatic heterocyclic group, V ₁ is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aromatic heterocyclic group, and the number of carbon atoms which may have 1 to 6 substituents Represents a linear or branched alkyl group of, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, X represents an oxygen atom or a sulfur atom, and W ₁ and W ₂ may be the same as or different from each other, and represent a carbon atom or a nitrogen atom.)

8) The organic EL device according to any one of the above 1) to 7), wherein the first hole transport layer contains a triphenylamine derivative represented by the following general formula (7) or (8).

[Formula 14]

(In the formula, R ₃₉ to R ₄₄ are each independently a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent. , A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a C 1 to 6 carbon atom which may have a substituent A linear or branched alkyloxy group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted Represents a substituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, r ₁ to r ₆ may be the same or different, respectively, r ₁ to r ₄ represents an integer of 0 to 5, r ₅ , r ₆ represents an integer of 0 to 4. When r ₁ to r ₆ are an integer of 2 or more, R ₃₉ to R ₄₄ bonded to a plurality of the same benzene ring may be the same or different, respectively. Substituents substituted with a ring are substituted with a plurality of substituents with the same benzene ring, and benzene rings adjacent to each other via a nitrogen atom are each attached to a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. K ₁ represents a divalent group represented by the following structural formulas (HTM-A) to (HTM-F) or a single bond.)

[Formula 15]

(In formula, j represents the integer of 1-3.)

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

(In the formula, R ₄₅ to R ₅₆ are each independently a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent. , A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a C 1 to 6 carbon atom which may have a substituent A linear or branched alkyloxy group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted Represents a substituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, r ₇ to r ₁₈ may be the same or different, respectively, r ₇ to r ₁₂ represent an integer of 0 to 5, and r ₁₃ to r ₁₈ represents an integer of 0 to 4. When r ₇ to r ₁₈ is an integer of 2 or more, a plurality of R ₄₅ to R ₅₆ bonded to the same benzene ring may be the same or different, respectively. Substituents substituted with a ring are substituted with a plurality of substituents with the same benzene ring, and benzene rings adjacent to each other via a nitrogen atom are each attached to a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. K ₂ to K ₄ may be the same or different, respectively, and a divalent group represented by (HTM-A) to (HTM-F) described in General Formula (7), or a single bond Represents.)

9) An arylamine compound represented by the following general formula (1).

[Formula 22]

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ may be the same or different, respectively, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation c Represents a cyclic aromatic group, and R ₁ , R ₂ , R ₃ may each be the same or different, and the number of carbon atoms from which each may have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a substituent is 1 to 6 linear or branched alkyl group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituent group A linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted A substituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

In "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in General Formula (1) As the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" of, specifically, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group , Indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, Benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, Naphthyridinyl group, phenanthrolinyl group, acridinyl group, and carbonyl group, etc. are mentioned.

As the "substituent" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1), specifically, a deuterium atom, Cyano group, nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; 1 carbon atom number such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, etc. A linear or branched alkyl group of to 6; A linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, and a propyloxy group; Alkenyl groups such as vinyl group and allyl group; Aryloxy groups such as phenyloxy group and tolyloxy group; Arylalkyloxy groups such as benzyloxy group and phenethyloxy group; Aromatic hydrocarbon groups such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, or Condensed polycyclic aromatic group; Pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, Aromatic heterocyclic groups such as benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, and carbolinyl group; Aryl vinyl groups such as a styryl group and a naphthyl vinyl group; Groups such as an acyl group such as an acetyl group and a benzoyl group may be mentioned, and these substituents may be further substituted with the above-described substituents. Moreover, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

"A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent" represented by R ₁ to R ₃ in general formula (1), and "a cyclo of 5 to 10 carbon atoms which may have a substituent""Alkylgroup" or "a linear or branched alkyl group having 1 to 6 carbon atoms" in the "linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent", and "carbon atom Specifically as a cycloalkyl group of 5 to 10" or a linear or branched alkenyl group of 2 to 6 carbon atoms", specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, Isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, An allyl group, an isopropenyl group, a 2-butenyl group, and the like, and these groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.

"A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "a cycloalkyl group having 5 to 10 carbon atoms having a substituent" or "a substituent represented by R ₁ to R ₃ in General Formula (1)" Specific examples of the "substituent" in "a linear or branched alkenyl group having 2 to 6 carbon atoms" having a substituent include a deuterium atom, a cyano group, and a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; A linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, and a propyloxy group; Alkenyl groups such as vinyl group and allyl group; Aryloxy groups such as phenyloxy group and tolyloxy group; Arylalkyloxy groups such as benzyloxy group and phenethyloxy group; Aromatic hydrocarbon groups such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, or Condensed polycyclic aromatic group; Pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, Groups such as aromatic heterocyclic groups such as benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, and carbolinyl group, and these substituents further, The substituents illustrated above may be substituted. Moreover, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent" or "5 to 10 carbon atoms which may have a substituent" represented by R ₁ to R ₃ in the general formula (1) As "a linear or branched alkyloxy group having 1 to 6 carbon atoms" or "a cycloalkyloxy group having 5 to 10 carbon atoms" in the "cycloalkyloxy group of", specifically, a methyloxy group , Ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group, cyclohexyloxy group, A cycloheptyloxy group, a cyclooctyloxy group, a 1-adamantyloxy group, a 2-adamantyloxy group, etc., and these groups represent a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. It may be interposed and bonded to each other to form a ring.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent" or "cycloalkyloxy group having 5 to 10 carbon atoms having a substituent" represented by R ₁ to R ₃ in the general formula (1) As the "substituent" in the above-described general formula (1), "a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent" and "carbon having a substituent group" represented by R ₁ to R ₃ The same as those shown for the ``substituent'' in the ``a cycloalkyl group having 5 to 10 atoms'' or the ``a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent group'' is mentioned. The same thing is mentioned also for an aspect.

In "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₁ to R ₃ in general formula (1) As "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" of the above, "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the general formula (1), and "substituted Or the same as those shown for ``aromatic hydrocarbon group'', ``aromatic heterocyclic group'' or ``condensed polycyclic aromatic group'' in the unsubstituted aromatic heterocyclic group" or the "substituted or unsubstituted condensed polycyclic aromatic group" These groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. In addition, these groups may have a substituent, and as a substituent, a "substituted aromatic hydrocarbon group", a "substituted aromatic heterocyclic group" or a "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1) The same thing as what was shown about the "substituent" in is mentioned, and the same thing can be mentioned as an aspect which can be taken.

As the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R ₁ to R ₃ in the general formula (1), specifically, a phenyloxy group, a biphenylyloxy group, a terphenylyloxy group, Naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc., and these groups are single bond, substituted or unsubstituted methylene A group, an oxygen atom, or a sulfur atom may be bonded to each other to form a ring. In addition, these groups may have a substituent, and as a substituent, a "substituted aromatic hydrocarbon group", a "substituted aromatic heterocyclic group" or a "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1) The same thing as what was shown about the "substituent" in is mentioned, and the same thing can be mentioned as an aspect which can be taken.

As Ar ₁ and Ar ₂ in the general formula (1), ``a substituted or unsubstituted aromatic hydrocarbon group'' or ``a substituted or unsubstituted condensed polycyclic aromatic group'' is preferable, and a phenyl group, a naphthyl group, a phenanthrenyl group, A fluorenyl group is more preferable, and a phenyl group having a substituent and a fluorenyl group having a substituent are particularly preferable. Here, as the substituent of the phenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthrenyl group, and a fluorenyl group are preferable, and as the substituent of the fluorenyl group, a methyl group and a phenyl group are preferable. As Ar ₃ and Ar ₄ in the general formula (1), a "substituted or unsubstituted aromatic hydrocarbon group" or a "substituted or unsubstituted condensed polycyclic aromatic group" is preferable, and a phenyl group, biphenylyl group, naphthyl group, phenane A renyl group and a fluorenyl group are more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group, and a fluorenyl group having a substituent are more preferable. Here, as the substituent for the fluorenyl group, a methyl group and a phenyl group are preferable.

As R ₁ and R ₃ in General Formula (1), a hydrogen atom and a deuterium atom are preferable, and a hydrogen atom is more preferable from a synthetic viewpoint.

As R ₂ in General Formula (1), ``a substituted or unsubstituted aromatic hydrocarbon group'' or a ``substituted or unsubstituted condensed polycyclic aromatic group'' is preferable, and a phenyl group, a biphenylyl group, a naphthyl group, a phenanthrenyl group, A fluorenyl group is more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group, and a fluorenyl group having a substituent are more preferable. Here, as the substituent for the fluorenyl group, a methyl group and a phenyl group are preferable.

Formula (2) "the number of carbon atoms which may have a substituent, an alkyl group of 1 to 6 linear or branched in the", "the number of carbon atoms which may have a substituent, an alkyl group of 5-10 cycloalkyl" represented by R ₄ in or ``Linear or branched alkyl group having 1 to 6 carbon atoms'' in ``a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent'', and ``5 to carbon atoms'' As 10 cycloalkyl group" or "linear or branched alkenyl group having 2 to 6 carbon atoms", specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group , tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, Isopropenyl group, 2-butenyl group, and the like.

``A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent'', ``a cycloalkyl group having 5 to 10 carbon atoms having a substituent'' or ``having a substituent group'' represented by R ₄ in the general formula (2) Specifically as a "substituent" in a C2-C6 linear or branched alkenyl group", it is a deuterium atom, a cyano group, a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; A linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, and a propyloxy group; Alkenyl groups such as vinyl group and allyl group; Aryloxy groups such as phenyloxy group and tolyloxy group; Arylalkyloxy groups such as benzyloxy group and phenethyloxy group; Aromatic hydrocarbon groups such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, or Condensed polycyclic aromatic group; Pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, Groups such as aromatic heterocyclic groups such as benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, and carbolinyl group are mentioned.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent" or "cycloalkyl having 5 to 10 carbon atoms which may have a substituent" represented by R ₄ in the general formula (2) Examples of "a linear or branched alkyloxy group having 1 to 6 carbon atoms" or a "cycloalkyloxy group having 5 to 10 carbon atoms" in the oxy group" are specifically methyloxy groups, ethyloxy groups Period, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy Period, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group, etc. are mentioned.

To ``a linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent'' or ``a cycloalkyloxy group having 5 to 10 carbon atoms having a substituent'' represented by R ₄ in the general formula (2) As the "substituent" in the above general formula (1), "a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent" and "5 carbon atoms having a substituent group" represented by R ₁ to R ₃ The same thing as those shown for the "substituent" in the "cycloalkyl group of to 10" or "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent" is mentioned. The same can be mentioned.

"Aromatic in a "substituted or unsubstituted aromatic hydrocarbon group" represented by R ₄ in the general formula (2), "a substituted or unsubstituted aromatic heterocyclic group", or "a substituted or unsubstituted condensed polycyclic aromatic group" As a "hydrocarbon group", a "aromatic heterocyclic group" or a "condensed polycyclic aromatic group", the "substituted or unsubstituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the general formula (1), and "substituted or unsubstituted The same as those shown for ``aromatic hydrocarbon group'', ``aromatic heterocyclic group'' or ``condensed polycyclic aromatic group'' in ``a substituted or unsubstituted condensed polycyclic aromatic group'' have. In addition, these groups may have a substituent, and as a substituent, a "substituted aromatic hydrocarbon group", a "substituted aromatic heterocyclic group" or a "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1) The same thing as what was shown about the "substituent" in is mentioned, and the same thing can be mentioned as an aspect which can be taken.

As the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R ₄ in the general formula (2), specifically, a phenyloxy group, a biphenylyloxy group, a terphenylyloxy group, and a naphthyloxy group , Anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, and the like. In addition, these groups may have a substituent, and as a substituent, a "substituted aromatic hydrocarbon group", a "substituted aromatic heterocyclic group" or a "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1) The same thing as what was shown about the "substituent" in is mentioned, and the same thing can be mentioned as an aspect which can be taken.

As R ₄ in the general formula (2), a hydrogen atom or a "substituted or unsubstituted aromatic hydrocarbon group" is preferable, a phenyl group and a naphthyl group are more preferable, and an unsubstituted phenyl group is more preferable.

Ar ₁ in the general formula (2), Ar ₂ is the same as Ar _1, Ar ₂ in the formula (1).

As Ar ₅ and Ar ₆ in the general formula (2), a phenyl group, biphenylyl group, naphthyl group, phenanthrenyl group, or fluorenyl group is more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, and an unsubstituted A naphthyl group and a fluorenyl group having a substituent are more preferable. Here, as the substituent for the fluorenyl group, a methyl group and a phenyl group are preferable.

As the "substituted or unsubstituted alkyl group having 1 to 15 carbon atoms" represented by R ₅ to R ₁₄ and Ra in the general formula (HOST-A), specifically, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group , s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group , 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydro Roxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group , 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-di Bromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group , 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triamino Propyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dishy Ano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3- Dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group , 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

As the "substituent" in the "substituted or unsubstituted alkyl group having 1 to 15 carbon atoms" represented by R ₅ to R ₁₄ and Ra in the general formula (HOST-A), R ₁ to R ₃ in the general formula (1) "A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "a cycloalkyl group having 5 to 10 carbon atoms having a substituent" or "a straight chain having 2 to 6 carbon atoms having a substituent" The same things as those shown for the "substituent group" in the "chain or branched alkenyl group" can be mentioned, and the same can be mentioned as the mode that can be taken.

As the "substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms" represented by R ₅ to R ₁₄ and Ra in the general formula (HOST-A), specifically, phenyl group, biphenylyl group, 1-naphthyl group, 2 -Naphthyl group, fluorophenyl group, difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group, pentafluorophenyl group, toluyl group, nitrophenyl group, cyanophenyl group, fluorobiphenylyl group, nitrobiphenylyl group, cyanobi And a phenyl group, a cyanonaphthyl group, a nitronaphthyl group, and a fluoronaphthyl group. Among the above, a phenyl group or a biphenylyl group is particularly preferable.

As a "substituent" in the "substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms" represented by R ₅ to R ₁₄ and Ra in the general formula (HOST-A), Ar ₁ in the general formula (1) The same as those shown for the "substituent group" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" represented by Ar ₄ can be exemplified. The same can be mentioned.

As the "substituted or unsubstituted phenylene group" represented by L ₁ in the general formula (HOST-A), the "substituted or unsubstituted biphenylene group", or the "substituent group" in the "substituted or unsubstituted terphenylene group" , "A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent" and "cycloalkyl group having 5 to 10 carbon atoms having a substituent" represented by R ₁ to R ₃ in the general formula (1). Or the same thing as what was shown about the "substituent" in "a C2-C6 linear or branched alkenyl group which has a substituent" is mentioned, and the same thing can be mentioned as an aspect which can be taken.

Specific examples of the "alkyl group having 1 to 15 carbon atoms" represented by R ₁₅ to R ₁₈ in the general formula (HOST-B) include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, iso Butyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl Group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3- Trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2 ,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodine Ethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2- Aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2 ,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group, etc. are mentioned.

As the "substituent" in the "alkyl group having 1 to 15 carbon atoms" represented by R ₁₅ to R ₁₈ in the general formula (HOST-B), the "carbon having a substituent group" represented by R ₁ to R ₃ in the general formula (1) A linear or branched alkyl group having 1 to 6 atoms", a "cycloalkyl group having 5 to 10 carbon atoms having a substituent" or "a linear or branched alkene having 2 to 6 carbon atoms having a substituent" The same thing as what was shown about the "substituent group" for "nyl group" is mentioned, and the same thing can be mentioned as an aspect which can be taken.

"Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms" or "substituted or unsubstituted heteroaryl group having 4 to 50 ring carbon atoms" represented by R ₁₅ to R ₁₈ in the general formula (HOST-B) Specific examples of "the aryl group having 6 to 50 ring carbon atoms" or the "heteroaryl group having 4 to 50 ring carbon atoms" specifically include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. , Fluorenyl group, indenyl group, pyrenyl group, acetonaftenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyranyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indole And a ril group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalyl group, a benzoimidazolyl group, a dibenzofuranyl group, and a dibenzothienyl group.

"Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms" or "substituted or unsubstituted heteroaryl group having 4 to 50 ring carbon atoms" represented by R ₁₅ to R ₁₈ in the general formula (HOST-B) As the "substituent" in the above general formula (1), the "substituent group" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ The same things as those shown for "" can be mentioned, and the same can be mentioned as a possible aspect.

"A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms" represented by Y in the general formula (HOST-B), or "a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms" Specific examples of the ``arylene group having 6 to 30 ring carbon atoms'' or the ``heteroarylene group having 5 to 30 ring carbon atoms'' include phenylene group, biphenylene group, terphenylene group, naphthylene group, anthrylene group, phenanthrylene group. , Fluorenylene group, indenylene group, pyrenylene group, acetonaphtenylene group, fluoranthenylene group, triphenylenylene group, pyridylene group, pyranylene group, quinolylene group, isoquinolylene group, benzofuranylene group , Benzothienylene group, indolylene group, carbazolylene group, benzooxazolylene group, benzothiazolylene group, quinoxalylene group, benzoimidazolylene group, pyrazolylene group, dibenzofuranylene group, and dibenzothienyl Rengi, etc. are mentioned.

"A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms" represented by Y in the general formula (HOST-B), or "a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms" As a "substituent", the "substituent group" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1) The same thing can be mentioned, and the same thing can be mentioned also the aspect which can be taken.

In ``a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms'' or ``a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms'' represented by Ar ₇ in the general formula (HOST-B) As ``aryl group having 6 to 30 ring carbon atoms'' or ``heteroaryl group having 5 to 30 ring carbon atoms'', specifically, phenyl group, naphthyl group, anthracenyl group, phenanthryl group, biphenyl group, p-terphenyl group, m-terphenyl group, quarter-phenyl group, fluorenyl group, triphenylene group, biphenylene group, pyrenyl group, benzofluoranthenyl group, chrysenyl group, phenylnaphthyl group, naphthylphenyl group, pyridyl group, quinolyl group, iso Quinolyl group, benzofuryl group, benzothienyl group, indolyl group, benzooxazolyl group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, etc. Can be mentioned.

In ``a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms'' or ``a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms'' represented by Ar ₇ in the general formula (HOST-B) Regarding the "substituent" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1) as a "substituent" The same thing as shown can be mentioned, and the same thing can be mentioned as an aspect which can be taken.

"A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent", and "a cyclo of 5 to 10 carbon atoms which may have a substituent" represented by R ₁₉ to R ₃₄ in the general formula (3) "Alkyl group" or "a linear or branched alkyl group having 1 to 6 carbon atoms" in the "linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent", and "carbon atom Specifically as a cycloalkyl group of 5 to 10" or a linear or branched alkenyl group of 2 to 6 carbon atoms", specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, Isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, Allyl group, isopropenyl group, 2-butenyl group, etc. are mentioned. Further, these groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.

"A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent", and "a cyclo of 5 to 10 carbon atoms which may have a substituent" represented by R ₁₉ to R ₃₄ in the general formula (3) As the "substituent" in the "alkyl group" or "a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent", "represented by R ₁ to R ₃ in the general formula (1)" A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent”, ``a cycloalkyl group having 5 to 10 carbon atoms having a substituent” or ``a linear linear or branched having 2 to 6 carbon atoms having a substituent The same things as those shown for the "substituent group" in the "branched alkenyl group" can be mentioned, and the same can be mentioned as a possible aspect.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent" or "5 to 10 carbon atoms which may have a substituent" represented by R ₁₉ to R ₃₄ in the general formula (3) As "a linear or branched alkyloxy group having 1 to 6 carbon atoms" or "a cycloalkyloxy group having 5 to 10 carbon atoms" in the "cycloalkyloxy group of", specifically, a methyloxy group , Ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group, cyclohexyloxy group, Cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group, etc. are mentioned.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent" or "cycloalkyloxy group having 5 to 10 carbon atoms having a substituent" represented by R ₁₉ to R ₃₄ in the general formula (3) As the "substituent" in the above-described general formula (1), "a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent" and "carbon having a substituent group" represented by R ₁ to R ₃ The same as those shown for the ``substituent'' in the ``a cycloalkyl group having 5 to 10 atoms'' or the ``a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent group'' is mentioned. The same thing is mentioned also for an aspect.

As the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R ₁₉ to R ₃₄ in the general formula (3), specifically, a phenyloxy group, a biphenylyloxy group, a terphenylyloxy group, Naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc., and these groups are single bond, substituted or unsubstituted methylene A group, an oxygen atom, or a sulfur atom may be bonded to each other to form a ring.

As the "substituent" in the "substituted or unsubstituted aryloxy group" represented by R ₁₉ to R ₃₄ in the general formula (3), the "substituted or unsubstituted group" represented by R ₁ to R ₃ in the general formula (1) The same things as those shown for the "substituent group" in "the aryloxy group of" are exemplified, and the same can be mentioned as a possible aspect.

To "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group", or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₁₉ to R ₃₄ in general formula (3) In the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group", specifically, a phenyl group, naphthyl group, anthracenyl group, phenanthryl group, naphthacenyl group, pyrenyl group, biphenylyl group , p-terphenyl group, m-terphenyl group, chrysenyl group, triphenylenyl group, perylenyl group, indenyl group, furanyl group, thiophenyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, oxa Zolyl group, thiazolyl group, oxadiazolyl group, thiadiazolyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, benzofuranyl group, benzothiophenyl group, benzimidazolyl group, indolyl group, qui Nolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, benzoxazinyl group, benzthiazinyl group, acridinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, or these It can be a combination, but is not limited to this.

To "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group", or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₁₉ to R ₃₄ in general formula (3) As the "substituent" in the above general formula (1), the "substituent group" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ The same thing as what was shown about is mentioned, and the same thing can be mentioned as an aspect which can be taken.

"Aromatic hydrocarbon group" in "a di-substituted amino group substituted by a group selected from the group consisting of an aromatic hydrocarbon group, an aromatic heterocyclic group, and a condensed polycyclic aromatic group" represented by R ₁₉ to R ₃₄ in the general formula (3). , As a "aromatic heterocyclic group" or a "condensed polycyclic aromatic group", specifically, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a naphthacenyl group, a pyrenyl group, a biphenylyl group, a p-terphenyl group, m -Terphenyl group, chrysenyl group, triphenylenyl group, perylenyl group, indenyl group, furanyl group, thiophenyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, oxazolyl group, thiazolyl group, Oxadiazolyl group, thiadiazolyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, benzofuranyl group, benzothiophenyl group, benzimidazolyl group, indolyl group, quinolinyl group, isoquinolinyl group , Quinazolinyl group, quinoxalinyl group, naphthyridinyl group, benzoxazinyl group, benzthiazinyl group, acridinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, or a combination thereof. Not limited. Moreover, these "aromatic hydrocarbon group", "aromatic heterocyclic group", or "condensed polycyclic aromatic group" may have a substituent, and as the said substituent, "Ar ₁ -Ar ₄ represented by the said general formula (1)" The same things as those shown for the "substituent group" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group", or the "substituted condensed polycyclic aromatic group" can be mentioned, and the same can be mentioned.

"Aromatic hydrocarbon group" or "condensed polycyclic aromatic group" in "substituted or unsubstituted aromatic hydrocarbon group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by Ar ₈ to Ar ₁₀ in general formula (4) As an aromatic group”, specifically, a phenyl group, a biphenylyl group, a terphenylyl group, a tetrakisphenyl group, a styryl group, a naphthyl group, an anthracenyl group, an acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl group , Groups such as perylenyl group, fluoranthenyl group, and triphenylenyl group.

As a "substituent" in the "substituted aromatic hydrocarbon group" or "substituted condensed polycyclic aromatic group" represented by Ar ₈ to Ar ₁₀ in the general formula (4), as Ar ₁ to Ar ₄ in the general formula (1) The same things as those shown for the "substituent group" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" can be mentioned, and the same can be mentioned. have.

As the "aromatic heterocyclic group" in the "substituted or unsubstituted aromatic heterocyclic group" represented by Ar ₁₁ in the structural formula (5), specifically, triazinyl group, pyridyl group, pyrimidinyl group, furyl group, pyrrole Ryl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, Groups such as pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, and carbonyl group are mentioned.

As the "substituent group" in the "substituted aromatic heterocyclic group" represented by Ar ₁₁ in the structural formula (5), the "substituted aromatic hydrocarbon group" and "substituted aromatic group" represented by Ar ₁ to Ar ₄ in the general formula (1) The same thing as those shown for the "substituent" in the "heterocyclic group" or the "substituted condensed polycyclic aromatic group" can be mentioned, and the same can be mentioned as a possible aspect.

As the "linear or branched alkyl group having 1 to 6 carbon atoms" represented by R ₃₅ to R ₃₈ in the structural formula (5), specifically, methyl group, ethyl group, n-propyl group, i-propyl group, n -Butyl group, 2-methylpropyl group, t-butyl group, n-pentyl group, 3-methylbutyl group, tert-pentyl group, n-hexyl group, iso-hexyl group, and tert-hexyl group.

In "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₃₅ to R ₃₈ in the structural formula (5) As the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" of, specifically, a phenyl group, a biphenylyl group, a terphenylyl group, a tetrakisphenyl group, a styryl group, a naphthyl group, an anthracenyl group, Acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazinyl group, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, Thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl Groups, such as a group, a dibenzofuranyl group, a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbonyl group are mentioned.

As a "substituent group" in the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" represented by R ₃₅ to R ₃₈ in the structural formula (5), the general formula (1) The same as those shown for the "substituent group" in the "substituted aromatic hydrocarbon group", the "substituted aromatic heterocyclic group" or the "substituted condensed polycyclic aromatic group" represented by Ar ₁ to Ar ₄ in The same thing is mentioned also in the aspect which exists.

Ar ₈ in the general formula (4) is a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, an acenaphtenyl group, a phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, and a fluoranthenyl group , A triphenylenyl group is preferable, and a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferable. Here, the phenyl group preferably has a substituted or unsubstituted condensed polycyclic aromatic group as a substituent, and a substituent selected from naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluoranthenyl group, and triphenylenyl group It is more preferable to have it.

Ar ₉ in the general formula (4) is preferably a phenyl group having a substituent, and as a substituent in this case, an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group, and a terphenyl group, a naphthyl group, an anthracenyl group, and an acenaphthenyl group , Phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, and other condensed polycyclic aromatic groups are preferred, and phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group , Pyrenyl group, fluoranthenyl group, and triphenylenyl group are more preferable.

Ar ₁₀ in the general formula (4) is preferably a phenyl group having a substituent, and as the substituent in this case, an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group, and a terphenyl group, a naphthyl group, an anthracenyl group, acenaphthe Condensed polycyclic aromatic groups such as phenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, and triphenylenyl group are preferable, and phenyl group, naphthyl group, anthracenyl group, phenanthre A nil group, a pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferable.

As Ar ₁₁ in the structural formula (5), triazinyl group, pyridyl group, pyrimidinyl group, pyrrolyl group, quinolyl group, isoquinolyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, Nitrogen-containing heterocyclic groups such as quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, and carbonyl group are preferable, and triazinyl group, pyridyl group, pyrimidinyl group, Quinolyl group, isoquinolyl group, indolyl group, quinoxalinyl group, benzoimidazolyl group, naphthyridinyl group, phenanthrolinyl group, and acridinyl group are more preferable, and pyridyl group, pyrimidinyl group, quinolyl group, iso A quinolyl group, an indolyl group, a quinoxalinyl group, a benzoimidazolyl group, a phenanthrolinyl group, and an acridinyl group are particularly preferable.

"Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by Ar ₁₂ , Ar ₁₃ and V ₁ in general formula (6) As the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in "", specifically, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, Fluorenyl group, spirobifluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, Quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, di And groups such as benzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, and carbonyl group.

"Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by Ar ₁₂ , Ar ₁₃ and V ₁ in the structural formula (6) As the "substituent group" in the above, "substituted aromatic hydrocarbon group" represented by Ar ₁ to Ar ₄ in the general formula (1), "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" The same thing as those shown for "substituent" is mentioned, and the same thing can be mentioned also the aspect which can be taken.

"A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent", "cycloalkyl group having 5 to 10 carbon atoms which may have a substituent", represented by V ₁ in the general formula (6), Or ``a linear or branched alkyl group having 1 to 6 carbon atoms'' in ``a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent'', and ``5 carbon atoms As a cycloalkyl group of to 10" or "a linear or branched alkenyl group having 2 to 6 carbon atoms", specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso Butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl Groups, such as a group, an isopropenyl group, and a 2-butenyl group, are mentioned.

"A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent", "cycloalkyl group having 5 to 10 carbon atoms which may have a substituent", represented by V ₁ in the general formula (6), Or as the "substituent" in "a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent", "having a substituent group" represented by R ₁ to R ₃ in the general formula (1) A linear or branched alkyl group having 1 to 6 carbon atoms, ``a cycloalkyl group having 5 to 10 carbon atoms having a substituent,'' or ``a linear or branched straight chain having 2 to 6 carbon atoms having a substituent The same thing as what was shown about the "substituent group" in the "alkenyl group" is mentioned, and the same thing can be mentioned as an aspect which can be taken.

"A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent" represented by R ₃₉ to R ₄₄ in the general formula (7), and "a cyclo of 5 to 10 carbon atoms which may have a substituent""Alkylgroup" or "a linear or branched alkyl group having 1 to 6 carbon atoms" in the "linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent", and "carbon atom Specifically as a cycloalkyl group of 5 to 10" or a linear or branched alkenyl group of 2 to 6 carbon atoms", specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, Isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, vinyl group, An allyl group, an isopropenyl group, a 2-butenyl group, and the like, and these groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.

"A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "a cycloalkyl group having 5 to 10 carbon atoms having a substituent" or "a substituent represented by R ₃₉ to R ₄₄ in the general formula (7)" Specific examples of the "substituent" in "a linear or branched alkenyl group having 2 to 6 carbon atoms" having a substituent include a deuterium atom, a cyano group, and a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; A linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, and a propyloxy group; Alkenyl groups such as vinyl group and allyl group; Aryloxy groups such as phenyloxy group and tolyloxy group; Arylalkyloxy groups such as benzyloxy group and phenethyloxy group; Aromatic hydrocarbon groups such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, or Condensed polycyclic aromatic group; Pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, Groups such as aromatic heterocyclic groups such as benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, and carbolinyl group, and these substituents further, The substituents illustrated above may be substituted. Moreover, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent" or "5 to 10 carbon atoms which may have a substituent" represented by R ₃₉ to R ₄₄ in the general formula (7) As "a linear or branched alkyloxy group having 1 to 6 carbon atoms" or "a cycloalkyloxy group having 5 to 10 carbon atoms" in the "cycloalkyloxy group of", specifically, a methyloxy group , Ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group, cyclohexyloxy group, A cycloheptyloxy group, a cyclooctyloxy group, a 1-adamantyloxy group, a 2-adamantyloxy group, etc., and these groups represent a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. It may be interposed and bonded to each other to form a ring.

In addition, these groups may have a substituent, and as a substituent, "a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent" represented by R ₃₉ to R ₄₄ in the general formula (7), and "substituent The same as those shown for the ``substituent group'' in the ``a cycloalkyl group having 5 to 10 carbon atoms having a'' or ``a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent'', The same can be mentioned as an aspect that can be taken.

In "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₃₉ to R ₄₄ in general formula (7) As the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" of, specifically, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group , Indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, Benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, Naphthyridinyl group, phenanthrolinyl group, acridinyl group, and carbonyl group, and the like, and these groups are bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. You may form.

In "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₃₉ to R ₄₄ in general formula (7) As the "substituent" of, specifically, a deuterium atom, a cyano group, a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom; 1 carbon atom number such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, etc. A linear or branched alkyl group of to 6; A linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, and a propyloxy group; Alkenyl groups such as vinyl group and allyl group; Aryloxy groups such as phenyloxy group and tolyloxy group; Arylalkyloxy groups such as benzyloxy group and phenethyloxy group; Aromatic hydrocarbon groups such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, or Condensed polycyclic aromatic group; Pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzooxazolyl group, Aromatic heterocyclic groups such as benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, and carbolinyl group; Aryl vinyl groups such as a styryl group and a naphthyl vinyl group; Acyl groups such as an acetyl group and a benzoyl group; Groups such as a silyl group such as a trimethylsilyl group and a triphenylsilyl group may be mentioned, and these substituents may further be substituted with the above-described substituents. Moreover, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

As the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R ₃₉ to R ₄₄ in the general formula (7), specifically, a phenyloxy group, a biphenylyloxy group, a terphenylyloxy group, Naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, etc., and these groups are single bond, substituted or unsubstituted methylene A group, an oxygen atom, or a sulfur atom may be bonded to each other to form a ring.

As the "substituent" in the "substituted or unsubstituted aryloxy group" represented by R ₃₉ to R ₄₄ in the general formula (7), the "substituted or unsubstituted group" represented by R ₁ to R ₃ in the general formula (1) The same things as those shown for the "substituent group" in "the aryloxy group of" are exemplified, and the same can be mentioned as a possible aspect.

In the formula _{(7), r 1 ~ r} 6 are may be the same or different and, r ₁ ~ r ₄ represents an integer of _{0 ~ 5, r 5, r} 6 represents an integer of 0-4. When r ₁ to r ₄ are integers of 2 to 5, or when r ₅ and r ₆ are integers of 2 to 4, R ₃₉ to R ₄₄ bonded to the same benzene ring may be the same or different, respectively, A single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom may be bonded to each other to form a ring.

As the "divalent linking group" represented by K ₁ in the general formula (7), a methylene group, ethylene group, n-propylylene group, isopropylylene group, n-butylylene group, isobutylylene group, tert-butylylene group "a linear or branched alkylene group having 1 to 6 carbon atoms" such as an n-pentylylene group, an isopentylylene group, a neopentylylene group, and an n-hexylylene group; "Cycloalkylene groups having 5 to 10 carbon atoms" such as a cyclopentylylene group, a cyclohexylylene group, and an adamantylylene group; "A linear or branched alkenylene group having 2 to 6 carbon atoms" such as a vinylene group, allylene group, isopropenylene group, and butenylene group; "A divalent group of an aromatic hydrocarbon" formed by removing two hydrogen atoms from an aromatic hydrocarbon such as benzene, biphenyl, terphenyl, and tetrakisphenyl; Divalent groups such as ``divalent groups of condensed polycyclic aromatics'' formed by removing two hydrogen atoms from condensed polycyclic aromatics such as naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene, indan, pyrene, and triphenylene Can be heard.

Moreover, these divalent groups may have a substituent. "Linear or branched alkylene group having 1 to 6 carbon atoms", "cycloalkylene group having 5 to 10 carbon atoms" or "linear or branched alkenylene group having 2 to 6 carbon atoms" As a substituent for "", "a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent" and "5 to 10 carbon atoms having a substituent" represented by R ₃₉ to R ₄₄ in the general formula (7). And the same as those shown for the "substituent" in the "cycloalkyl group of" or "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent". As a substituent for "a divalent group of an aromatic hydrocarbon" or a "divalent group of a condensed polycyclic aromatic", a "substituted or unsubstituted aromatic hydrocarbon group" represented by R ₃₉ to R ₄₄ in the general formula (7), and a "substituted Or the same thing as what was shown about the "substituent group" in an unsubstituted aromatic heterocyclic group" or "a substituted or unsubstituted condensed polycyclic aromatic group" can be mentioned, and the same can be mentioned as a possible aspect.

As a preferable aspect of the "divalent linking group" represented by K ₁ in General Formula (7), a divalent group represented by the structural formulas (HTM-A) to (HTM-F) can be mentioned.

"A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent" represented by R ₄₅ to R ₅₆ in the general formula (8), and "a cyclo of 5 to 10 carbon atoms which may have a substituent""Alkylgroup" or "a linear or branched alkyl group having 1 to 6 carbon atoms" in the "linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent", and "carbon atom As a "cycloalkyl group of 5 to 10" or "a linear or branched alkenyl group of 2 to 6 carbon atoms", "carbon which may have a substituent represented by R ₃₉ to R ₄₄ in the general formula (7) A linear or branched alkyl group having 1 to 6 atoms, ``a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent,'' or ``a linear or branched chain having 2 to 6 carbon atoms which may have a substituent, or "A linear or branched alkyl group having 1 to 6 carbon atoms" in a branched alkenyl group", a "cycloalkyl group having 5 to 10 carbon atoms" or a "linear linear group having 2 to 6 carbon atoms" Or the same thing as what was shown about "branched alkenyl group" is mentioned, and the same thing can be mentioned as an aspect which can be taken.

``A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent'', ``a cycloalkyl group having 5 to 10 carbon atoms having a substituent'' or ``represented by R ₄₅ to R ₅₆ in the general formula (8) As the "substituent" in "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent", "the number of carbon atoms having a substituent 1 represented by R ₃₉ to R ₄₄ in the general formula (7) To a linear or branched alkyl group of to 6", "a cycloalkyl group having 5 to 10 carbon atoms having a substituent" or "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent" The same things as those shown with respect to the "substituent" in the above can be mentioned, and the same can be mentioned as a possible aspect.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent" or "5 to 10 carbon atoms which may have a substituent" represented by R ₄₅ to R ₅₆ in the general formula (8) As "a linear or branched alkyloxy group having 1 to 6 carbon atoms" or "a cycloalkyloxy group having 5 to 10 carbon atoms" in the "cycloalkyloxy group of", the general formula (7) "A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent" or "cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent" represented by R ₃₉ to R ₄₄ in The same as those shown for ``a linear or branched alkyloxy group having 1 to 6 carbon atoms'' or ``a cycloalkyloxy group having 5 to 10 carbon atoms'' in ``. The same thing is mentioned also for an aspect.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent" or "cycloalkyloxy group having 5 to 10 carbon atoms having a substituent" represented by R ₄₅ to R ₅₆ in the general formula (8) As the "substituent" in the above-mentioned general formula (7), "a linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent" or "substituent group" represented by R ₃₉ to R ₄₄ The same thing as what was shown about the "substituent" in the C5-C10 cycloalkyloxy group" which it has, and the aspect which can be taken are also the same thing.

In "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₄₅ to R ₅₆ in general formula (8) As "aromatic hydrocarbon group", "aromatic heterocyclic group", or "condensed polycyclic aromatic group" of, "substituted or unsubstituted aromatic hydrocarbon group" represented by R ₃₉ to R ₄₄ in the general formula (7), and "substituted Or the same as those shown for ``aromatic hydrocarbon group'', ``aromatic heterocyclic group'' or ``condensed polycyclic aromatic group'' in the unsubstituted aromatic heterocyclic group" or the "substituted or unsubstituted condensed polycyclic aromatic group" These groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

In addition, these groups may have a substituent, and as a substituent, a "substituted aromatic hydrocarbon group" represented by R ₃₉ to R ₄₄ in the general formula (7), a "substituted aromatic heterocyclic group" or a "substituted condensed polycyclic aromatic group" The same thing as what was shown about the "substituent" in is mentioned, and the same thing can be mentioned as an aspect which can be taken.

As the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R ₄₅ to R ₅₆ in the general formula (8), the "substituted or unsubstituted aryloxy group" represented by R ₃₉ to R ₄₄ in the general formula (7) The same thing as those shown for the "aryloxy group" in the "unsubstituted aryloxy group" is mentioned, and the same thing can be mentioned as an aspect which can be taken.

As the "substituent" in the "aryloxy group having a substituent" represented by R ₄₅ to R ₅₆ in the general formula (8), the "aryloxy group having a substituent" represented by R ₃₉ to R ₄₄ in the general formula (7) The same thing as those shown for the "substituent" in "" can be mentioned, and the same thing can be mentioned as an aspect which can be taken.

In the formula (8), r is ₇ ~ r ₁₈ are may be the same or different, r ₇ ~ ₁₂ r is an integer of _{0 ~ 5, r 13 ~ r} 18 represents an integer of 0-4. When r ₇ to r ₁₂ is an integer of 2 to 5, or when r ₁₃ to r ₁₈ is an integer of 2 to 4, a plurality of R ₄₅ to R ₅₆ bonded to the same benzene ring may be the same or different, respectively, A single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom may be bonded to each other to form a ring.

Examples of the "divalent linking group" represented by K ₂ , K ₃ , and K ₄ in the general formula (8) include the same as those shown for the "divalent linking group" represented by K ₁ in the general formula (7). The same can be mentioned also for the possible aspect.

The arylamine compound represented by the general formula (1) of the present embodiment is a novel compound, has an ability to trap triplet excitons superior to conventional hole transport materials, has an excellent hole transport ability, and has excellent amorphous properties. And the thin film state is stable.

The arylamine compound represented by the general formula (1) of the present embodiment can be used as a host material for the second hole transport layer and/or the light emitting layer adjacent to the light emitting layer of the organic EL device. Compared with conventional materials, by using a material having high hole injection properties, high mobility, high electron blocking properties, and high stability against electrons, excitons generated in the light emitting layer can be trapped. Accordingly, the probability of recombination of holes and electrons is further improved, and high light emission efficiency can be obtained. At the same time, the driving voltage is lowered and the durability of the organic EL element is improved.

The arylamine compound represented by the general formula (1) of the present embodiment can also be used as a material for constituting the light emitting layer of the organic EL device. Compared with conventional materials, the compound has excellent hole transport properties, and particularly, when it contains a green phosphorescent light-emitting material, more preferably has an effect of improving the luminous efficiency of the organic EL device.

The organic EL device of the present embodiment uses an arylamine compound that has greater hole mobility, excellent electron blocking ability, excellent amorphous property, and excellent electrical reduction durability than conventional hole transport materials. Are doing. Therefore, it becomes possible to realize high efficiency and high durability.

Among the arylamine compounds represented by General Formula (1), specific examples of preferred compounds are shown below, but the present invention is not limited to these compounds.

[Formula 23]

[Formula 24]

[Formula 25]

[Formula 26]

[Formula 27]

[Formula 28]

In addition, the arylamine compound described above can be synthesized in accordance with a method known per se (see, for example, Patent Document 8). For example, as shown in the examples to be described later, by reacting a di-substituted amine with a halogenated substituted aromatic hydrocarbon by a coupling reaction, and further halogenating the obtained compound to react with a boronic acid of an aromatic hydrocarbon by a coupling reaction. , The arylamine compound described above can be synthesized.

Among the compounds represented by the general formula (Host-A), which are preferably used in the organic EL device of the present embodiment, specific examples of preferred compounds are shown below, but the present invention is not limited to these compounds.

[Chemical Formula 29]

[Chemical Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

In addition, the compound having the above-described nitrogen-containing heteroaromatic ring structure can be synthesized according to a method known per se (see, for example, Patent Documents 4 and 5).

Among the compounds represented by the general formula (Host-B), which are preferably used in the organic EL device of the present embodiment, specific examples of preferred compounds are shown below, but the present invention is not limited to these compounds.

[Formula 34]

[Formula 35]

[Formula 36]

[Chemical Formula 37]

[Formula 38]

In addition, the compound having the above-described hamcarbazole structure can be synthesized according to a method known per se (for example, see Patent Documents 4 and 5).

Among the compounds represented by the general formula (3), which are preferably used in the organic EL device of the present embodiment, specific examples of preferred compounds are shown below, but the present invention is not limited to these compounds.

[Formula 39]

[Formula 40]

In addition, the iridium complex described above can be synthesized according to a method known per se (see, for example, Patent Documents 9 and 10).

Among the compounds having a pyrimidine ring structure represented by the general formula (4), which are preferably used in the organic EL device of the present embodiment, specific examples of preferred compounds are shown below, but the present invention is limited to these compounds. It is not.

[Formula 41]

[Formula 42]

[Formula 43]

[Formula 44]

[Formula 45]

In addition, the compound having the above-described pyrimidine ring structure can be synthesized by a method known per se (see, for example, Patent Documents 10 and 11).

Among the compounds having a benzoazole ring structure represented by the general formula (6), which are preferably used in the organic EL device of the present embodiment, specific examples of preferred compounds are shown below, but the present invention is limited to these compounds. It is not.

[Formula 46]

[Chemical Formula 47]

[Formula 48]

[Chemical Formula 49]

In addition, the compound having the above-described benzoazole ring structure can be synthesized according to a method known per se (for example, Patent Documents 13 and 14).

Among the triphenylamine derivatives represented by the general formula (7), which are preferably used in the organic EL device of the present embodiment, specific examples of preferred compounds are shown below, but the present invention is not limited to these compounds.

[Formula 50]

[Formula 51]

Among the triphenylamine derivatives represented by the general formula (8), which are preferably used in the organic EL device of the present embodiment, specific examples of preferred compounds are shown below, but the present invention is not limited to these compounds.

[Formula 52]

[Formula 53]

In addition, the compound having the above-described triarylamine structure can be synthesized according to a method known per se (see, for example, Patent Documents 1 and 2 and Patent Document 15).

Purification of general formulas (1) to (8), (HOST-A) and (HOST-B) is purification by column chromatography, adsorption purification by silica gel, activated carbon, activated clay, etc., recrystallization or crystallization by a solvent. , Sublimation purification, or the like. Identification of a compound can be performed by NMR analysis. As the physical property values, the melting point, the glass transition point (Tg) and the work function are measured. The melting point is an index of evaporation property, the glass transition point (Tg) is an index of stability of the thin film state, and the work function is an index of hole transportability and hole blocking property.

In addition, as the compound used in the organic EL device of the present embodiment, after purification by column chromatography, adsorption purification by silica gel, activated carbon, activated clay, etc., recrystallization or crystallization using a solvent, or the like, Finally, the one purified by the sublimation purification method is used.

The melting point and the glass transition point (Tg) can be measured using a powder with a high sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100SA).

The work function can be obtained by forming a 100 nm thin film on an ITO substrate and using an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., PYS-202).

T1 of these compounds can be calculated from the measured phosphorescence spectrum. The phosphorescence spectrum can be measured using a commercially available spectrophotometer. As a general method of measuring the phosphorescence spectrum, it is dissolved in a solvent and measured by irradiating excitation light under low temperature (for example, see Non-Patent Document 3), or depositing on a silicon substrate to form a thin film and excitation under low temperature. There is a method of measuring a phosphorescence spectrum by irradiating light (see, for example, Patent Document 16). T1 can be calculated by reading the wavelength of the first peak on the short wavelength side of the phosphorescent spectrum or the wavelength of the rising position on the short wavelength side, and converting it to the energy value of light according to the following equation. T1 is an index of the trapping ability of the triplet excitons of the phosphorescent luminous body.

Here, E is the value of the light energy, h is the Planck's constant (6.63 × 10 ^-34 Js), c is the luminous flux (3.00 × 10 ⁸ m/s), and λ is the rising point of the short wavelength side of the phosphorescent spectrum. It represents the wavelength (nm). And, 1 eV becomes 1.60 × 10 ^-19 J.

As the structure of the organic EL device of this embodiment, an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode are sequentially stacked on a substrate, and , In addition to the structure, those having a hole blocking layer between the light emitting layer and the electron transport layer are mentioned. In such a multilayer structure, it is possible to omit or combine several organic layers, and for example, a configuration (layer) in which an electron injection layer and an electron transport layer are combined can also be used. Further, it is possible to have a configuration in which two or more layers of organic layers having the same function are stacked, a configuration in which two light emitting layers are stacked, a configuration in which two electron transport layers are stacked, etc. are possible.

As the anode of the organic EL device of this embodiment, an electrode material having a large work function such as ITO or gold is used. As the hole injection layer of the organic EL device of the present embodiment, in addition to the arylamine compounds represented by the general formulas (7) and (8), a porphyrin compound represented by copper phthalocyanine, a starburst triphenylamine derivative, and hexacyano It is possible to use an acceptor heterocyclic compound such as azatriphenylene or a coating polymer material. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method.

As the first hole transport layer of the organic EL device of the present embodiment, an arylamine compound represented by the general formulas (7) and (8) is more preferable. In addition, N,N'-diphenyl-N,N'- Di(m-tolyl)-benzidine (hereinafter abbreviated as TPD) or N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (hereinafter abbreviated as NPD), N, Benzidine derivatives such as N,N',N'-tetrabiphenylylbenzidine, 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (hereinafter abbreviated as TAPC), and the like can also be used. These may be formed alone, or may be used as a single layer formed by mixing together with other materials, layers formed by mixing the plurality of materials alone, layers formed by mixing the plurality of materials, or the plurality of A layered structure of a layer formed by mixing a material alone with a layer formed into a film may be obtained. In addition, as a hole injection/transport layer, a coating-type polymer material such as poly(3,4-ethylenedioxythiophene) (hereinafter, abbreviated as PEDOT)/poly(styrenesulfonate) (hereinafter, abbreviated as PSS), etc. You can use In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method.

In addition, in the hole injection layer or the hole transport layer, in addition to the material normally used for the layer, trisbromophenylamine hexachlorantimony, a radicalene derivative (e.g., a compound described later (Acceptor-1 (Acceptor -1)), and also P-doped (see Patent Document 17), or a polymer compound having a structure of a benzidine derivative such as TPD in its partial structure can be used.

As the second hole transport layer of the organic EL device of the present embodiment, in addition to the arylamine compound represented by the general formula (1) of the present embodiment, 4,4',4''-tri(N-carbazolyl)triphenylamine (Hereinafter, abbreviated as TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP) ), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (hereinafter, abbreviated as Ad-Cz), and other carbazole derivatives, 9-[4-(carbazole-9-yl) )Phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene and a compound having an electron blocking action such as a compound having a triphenylsilyl group and a triarylamine structure can be used. These may be formed as a single layer, but may be used as a single layer formed by mixing with other materials, layers formed by mixing alone, layers formed by mixing, or layering layers formed by mixing with a layer formed alone It may be structured. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method.

As the host of the light emitting layer of the organic EL device of the present embodiment, a host material having a hole transport property or a host material having an electron transport property can be used. As a hole-transporting host material, in addition to the compound having a carbazole ring structure represented by the general formula (HOST-B) or the arylamine compound represented by the general formula (1) of the present embodiment, 4,4'-di(N -Carbazolyl)biphenyl (CBP) or carbazole derivatives such as TCTA and mCP can be used. As the electron transporting host material, in addition to the compound having a nitrogen-containing heteroaromatic ring structure represented by the general formula (HOST-A), p-bis(triphenylsilyl)benzene (UGH2) or 2,2',2'' -(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBi) and the like can be used. These may be formed into a film alone, but may be used as a single layer formed by mixing a plurality of materials, or layers formed by mixing alone, layers formed by mixing, or layering layers formed by mixing with a layer formed alone It may be structured. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method.

In this embodiment, it is preferable to use two or more types of compounds, a first host compound having an electron transporting ability and a second host compound having a hole transporting ability. As for the said 2nd host compound, 1 type or 2 or more types may be used. The first host compound and the second host compound may be included in a weight ratio of 1:10 to 10:1, for example.

As the first host compound of the light emitting layer of the organic EL device of the present embodiment, a compound having a nitrogen-containing heteroaromatic ring structure represented by the general formula (HOST-A) is preferable, and as the second host compound, the A compound having a carbazole ring structure represented by General Formula (HOST-B) or an arylamine compound represented by General Formula (1) of the present embodiment is preferable.

In addition to the above-described first host compound and second host compound, one or more host compounds may be further included.

As the phosphorescent light emitting material of the organic EL device of the present embodiment, the iridium complex represented by the general formula (3) of the present embodiment is more preferable. In addition, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm , Fe, Co, Ni, Ru, Rh, Pd, or an organometallic compound containing a combination thereof may be used. The dopant may be a red, green, or blue dopant, and a high-performance organic EL device can be manufactured.

Doping of the phosphorescent light-emitting material to the host material is preferably doped by co-deposition in the range of 1 to 30 weight percent with respect to the entire light-emitting layer in order to avoid concentration quenching.

In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method.

As the hole blocking layer of the organic EL device of the present embodiment, the benzoazole compounds and pyrimidine compounds represented by the general formulas (4) and (6) are more preferable, but in addition, vasocuproin (hereinafter, abbreviated as BCP) In addition to metal complexes of phenanthroline derivatives such as) and quinolinol derivatives such as BAlq, various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and other compounds having a hole blocking function can be used. You may also serve as a material for the electron transport layer. These may be formed alone, or may be used as a single layer formed by mixing together with other materials, layers formed by mixing the plurality of materials alone, layers formed by mixing the plurality of materials, or the plurality of A layered structure of a layer formed by mixing a material alone with a layer formed into a film may be obtained. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method.

As the electron transport layer of the organic EL device of the present embodiment, the benzoazole compounds and pyrimidine compounds represented by the general formulas (4) and (6) are more preferable. In addition, Alq ₃ , BAlq, and the compounds described later (ETM- 1) In addition to metal complexes of quinolinol derivatives, including various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives , Quinoxaline derivatives, pyridindole derivatives, phenanthroline derivatives, silol derivatives, and the like can also be used. These may be formed alone, or may be used as a single layer formed by mixing together with other materials, layers formed by mixing the plurality of materials alone, layers formed by mixing the plurality of materials, or the plurality of A layered structure of a layer formed by mixing a material alone with a layer formed into a film may be obtained. In addition to the vapor deposition method, these materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method.

As the electron injection layer of the organic EL device of the present embodiment, alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, metal complexes of quinolinol derivatives such as lithium quinolinol, and metals such as aluminum oxide An oxide or the like can be used, but in a preferred selection of the electron transport layer and the cathode, this can be omitted.

In addition, in the electron injection layer or the electron transport layer, an organic compound normally used in the layer may be further N-doped with a metal such as cesium, lithium fluoride, and ytterbium.

As the cathode of the organic EL device of this embodiment, an electrode material having a low work function such as aluminum and ytterbium, or an alloy having a lower work function such as magnesium alloy, magnesium indium alloy, and aluminum magnesium alloy is used as the electrode material. .

Hereinafter, embodiments of the present invention will be specifically described with reference to Examples, but the present invention is not limited to the following Examples, unless departing from the gist of the present invention.

Example 1

<Synthesis of di(biphenyl-4-yl)-(2'-phenyl-1,1':3',1''-terphenyl-5'-yl)-amine (compound 1-1)>

In a nitrogen-substituted reaction vessel, di(biphenyl-4-yl)-amine: 50.0 g, 5'-bromo-1,1':3',1'' terphenyl: 57.7 g, t-butoxy sodium : 59.8 g, toluene: 1000 ml was added, and nitrogen gas was ventilated while irradiating ultrasonic waves for 30 minutes. Palladium acetate: 1.4 g, 50% (w/v) toluene solution of t-butylphosphine: 2.5 ml were added, followed by stirring under heating and refluxing for 4 hours. After standing to cool, EtOAc and H ₂ O were added, and the organic layer was extracted by a liquid separation operation, and concentrated under reduced pressure to obtain a crude product. Toluene/acetone mixed solvent was added to the preparation, and the precipitated solid was collected, and di(biphenyl-4-yl)-(1,1':3',1''-terphenyl-5'-yl)- White powder of amine: 73.9 g (yield 86%) was obtained.

Di(biphenyl-4-yl)-(1,1':3',1''-terphenyl-5'-yl)-amine: 62.3 g, dichloromethane: 1250 ml was added to a reaction vessel substituted with nitrogen And cooled in an ice bath. N-bromosuccinimide: 20.2 g was added, followed by stirring for 8 hours. After the reaction solution was concentrated under reduced pressure, methanol was added and the precipitated solid was collected, and (2'-bromo-1,1':3',1''-terphenyl-5'-yl)-di( The white solid of biphenyl-4-yl)-amine: 60.0 g (yield 84%) was obtained.

In a nitrogen-substituted reaction vessel, (2'-bromo-1,1':3',1''-terphenyl-5'-yl)-di(biphenyl-4-yl)-amine: 10.0 g, Toluene: 80 ml, ethanol: 40 ml, phenylboronic acid: 2.3 g, then an aqueous solution in which potassium carbonate: 6.6 g was previously dissolved in H ₂ O: 30 ml was added, and nitrogen gas was ventilated while irradiating ultrasonic waves for 30 minutes. I did. Tetrakistriphenylphosphine palladium: 0.4 g was added, followed by stirring under heating and refluxing for 24 hours. After standing to cool, EtOAc and H ₂ O were added, and the organic layer was extracted by liquid separation, and concentrated under reduced pressure to obtain a crude product. Toluene was added to the preparation, and the precipitated solid was collected, di(biphenyl-4-yl)-(2'-phenyl-1,1':3',1''-terphenyl-5'-yl) -White powder of amine (compound 1-1): 4.0 g (yield 40%) was obtained.

[Chemical Formula 54]

The structure of the obtained white powder was identified using NMR.

Signals of the following 35 hydrogens were detected by ¹ H-NMR (CDCl ₃ ).

Example 2

<(biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)-(2'-phenyl-1,1':3',1''-terphenyl-5' Synthesis of -yl)-amine (Compound 1-2)>

Synthesized by the same method as in Example 1, (biphenyl-4-yl)-(2'-bromo-1,1':3',1''-terphenyl-5'-yl)-(9, To 9-dimethyl-9H-fluoren-2-yl)-amine: 17.6 g, toluene: 170 ml, ethanol: 35 ml, phenylboronic acid: 3.7 g, and then potassium carbonate: 4.4 g in advance were added to H ₂ O : An aqueous solution dissolved in 30 ml was added, and nitrogen gas was ventilated while irradiating ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.6 g was added, followed by stirring under heating and refluxing for 24 hours. After standing to cool, an organic layer was collected by liquid separation operation. Washing was performed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. (Biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)- by purifying the prepared product by column chromatography using a toluene/n-heptane mixed solvent White powder of (2'-phenyl-1,1':3',1''-terphenyl-5'-yl)-amine (compound 1-2): 11.2 g (64% yield) was obtained.

[Formula 55]

The structure of the obtained white powder was identified using NMR.

Signals of the following 39 hydrogens were detected by ¹ H-NMR (CDCl ₃ ).

Example 3

<Di(9,9-dimethyl-9H-fluoren-2-yl)-(2'-phenyl-1,1':3',1''-terphenyl-5'-yl)-amine (compound 1 -3) Synthesis of>

Synthesized by the same method as in Example 1, (2'-bromo-1,1':3',1''-terphenyl-5'-yl)-di(9,9-dimethyl-9H-fluorene -2-yl)-amine: to 10.0 g, toluene: 80 ml, ethanol: 40 ml, phenylboronic acid: 2.1 g, and then potassium carbonate: 5.9 g in advance in H ₂ O: 30 ml After addition, nitrogen gas was ventilated while irradiating ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.3 g was added, followed by stirring under heating and refluxing for 5 hours. After standing to cool, EtOAc and H ₂ O were added, and the organic layer was extracted by liquid separation, and concentrated under reduced pressure to obtain a crude product. A THF/acetone mixed solvent was added to the preparation, and the precipitated solid was collected, and di(9,9-dimethyl-9H-fluoren-2-yl)-(2'-phenyl-1,1':3', White powder of 1''-terphenyl-5'-yl)-amine (compound 1-3): 7.7 g (yield 77%) was obtained.

[Formula 56]

The structure of the obtained white powder was identified using NMR.

Signals of the following 43 hydrogens were detected by ¹ H-NMR (DMSO-d ₆ ).

Example 4

<(biphenyl-4-yl)-(9,9-diphenyl-9H-fluoren-2-yl)-(2'-phenyl-1,1':3',1''-terphenyl-5 Synthesis of'-yl)-amine (compound 1-4)>

Synthesized by the same method as in Example 1, (biphenyl-4-yl)-(2'-bromo-1,1':3',1''-terphenyl-5'-yl)-(9, 9-diphenyl-9H-fluoren-2-yl)-amine: to 14.0 g, toluene: 140 ml, ethanol: 35 ml, phenylboronic acid: 3.2 g, and then potassium carbonate: 4.9 g beforehand, H ₂ O: An aqueous solution dissolved in 35 ml was added, and nitrogen gas was vented while irradiating ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.4 g was added, followed by stirring under heating and refluxing for 20 hours. After standing to cool, EtOAc and H ₂ O were added, and the organic layer was extracted by liquid separation, and concentrated under reduced pressure to obtain a crude product. Toluene/acetone mixed solvent was added to the preparation, and the precipitated solid was collected, and (biphenyl-4-yl)-(9,9-diphenyl-9H-fluoren-2-yl)-(2'-phenyl White powder of -1,1':3',1''-terphenyl-5'-yl)-amine (compound 1-4): 7.5 g (yield 54%) was obtained.

[Formula 57]

The structure of the obtained white powder was identified using NMR.

Signals of the following 43 hydrogens were detected by ¹ H-NMR (DMSO-d ₆ ).

Example 5

<(biphenyl-4-yl)-{4-(naphthyl-2-yl)-phenyl)}-(2'-phenyl-1,1':3',1''-terphenyl-5'- Synthesis of Il)-amine (Compound 1-58)>

Synthesized by the same method as in Example 1, (biphenyl-4-yl)-(2'-bromo-1,1':3',1''-terphenyl-5'-yl)-(4- (Naphthyl-2-yl)-phenyl)}-amine: To 10.0 g, toluene: 70 ml, ethanol: 30 ml, phenylboronic acid: 2.7 g, and then potassium carbonate: 6.1 g in advance, H ₂ O: An aqueous solution dissolved in 20 ml was added, and nitrogen gas was ventilated while irradiating ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.3 g was added, followed by stirring under heating and refluxing for 24 hours. After standing to cool, methanol was added and the precipitated solid was collected to obtain a crude product. A mixture of THF/acetone was added to the preparation, and the precipitated solid was collected, and (biphenyl-4-yl)-(2'-bromo-1,1':3',1''-terphenyl-5 White powder of'-yl)-{4-(naphthyl-2-yl)-phenyl)}-amine (compound 1-58): 6.5 g (yield 65%) was obtained.

[Formula 58]

The structure of the obtained white powder was identified using NMR.

Signals of the following 37 hydrogens were detected by ¹ H-NMR (DMSO-d ₆ ).

Example 6

<Di{4-(naphthyl-2-yl)-phenyl)}-(2'-phenyl-1,1':3',1''-terphenyl-5'-yl)-amine (compound 1- 62) Synthesis>

Synthesized by the same method as in Example 1, (2'-bromo-1,1':3',1''-terphenyl-5'-yl)-di(4-(naphthyl-2-yl) -Phenyl)}-amine: To 15.0 g, toluene: 160 ml, ethanol: 40 ml, phenylboronic acid: 3.0 g, and then potassium carbonate: 5.7 g previously dissolved in H ₂ O: 40 ml aqueous solution was added Then, nitrogen gas was vented while irradiating ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.5 g was added, followed by stirring under heating and refluxing for 21 hours. After standing to cool, an organic layer was collected by liquid separation operation. Washing was performed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. Toluene/n-heptane mixed solvent was added to the preparation, and the precipitated solid was collected, and di{4-(naphthyl-2-yl)-phenyl)}-(2'-phenyl-1,1':3' White powder of ,1''-terphenyl-5'-yl)-amine (compound 1-62): 8.2 g (yield 55%) was obtained.

[Formula 59]

The structure of the obtained white powder was identified using NMR.

Signals of the following 39 hydrogens were detected by ¹ H-NMR (DMSO-d ₆ ).

Example 7

About the arylamine compound represented by general formula (1), the glass transition point was calculated|required with the high sensitivity differential scanning calorimeter (made by Bruker AXS, DSC3100S).

Glass transition point

Compound of Example 1 110 ℃

Compound of Example 2 121 ℃

Compound of Example 3 135 ℃

Compound of Example 4 140 ℃

Compound of Example 5 115 ℃

Compound of Example 6 121 ℃

The arylamine compound represented by the general formula (1) has a glass transition point of 100°C or higher, and shows a stable thin film state.

Example 8

Using the compounds of Examples 1 to 6, a vapor deposition film having a film thickness of 100 nm was prepared on an ITO substrate, and the work function was measured with an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., PYS-202 type). .

Work function

Compound of Example 1 5.71 eV

Compound of Example 2 5.62 eV

Compound of Example 3 5.58 eV

Compound of Example 4 5.69 eV

Compound of Example 5 5.70 eV

Compound of Example 6 5.69 eV

As described above, it can be seen that the compounds of Examples 1 to 6 exhibit a preferable energy level and have good hole transport ability compared with the work function of 5.4 eV of general hole transport materials such as NPD and TPD.

Example 9

For the compounds of Examples 1 to 4, a 1.0 × 10 ^-5 mol/L 2-methyltetrahydrofuran solution was prepared. The prepared solution was put in a dedicated quartz tube, and pure nitrogen was vented to remove oxygen content, and a stopper with a septum rubber was applied so that no additional oxygen content was mixed. After cooling to 77 K, a fluorescence phosphorescence spectrophotometer (manufactured by Nippon Spectroscopy Co., Ltd., FP-8500 type) was used, and excitation light was irradiated to measure the phosphorescence spectrum. The wavelength of the first peak on the short wavelength side of the phosphorescence spectrum was read, and the wavelength value was converted into light energy to calculate T1. In addition, T1 of HTM-2 and compound (3-3) are also shown below as a reference.

T1

Compound (1-1) of Example 1 2.55 eV

Compound of Example 2 (1-2) 2.58 eV

Compound of Example 3 (1-3) 2.58 eV

Compound of Example 4 (1-4) 2.57 eV

HTM-2 2.40 eV

Compound 3-3 2.43 eV

[Chemical Formula 60]

[Formula 61]

[Formula 62]

[Formula 63]

[Formula 64]

[Formula 65]

As described above, the compound used in the present disclosure has a value greater than T1 of tri(m-terphenyl-4-yl)amine (HTM-2), which is a commonly used hole transport material. A large twist occurs in the skeleton around the amine by two phenyl groups substituted at the meta position with respect to the nitrogen atom of the triarylamine, and the phenyl group substituted at the position para with respect to the nitrogen atom acts as a large steric hindrance group. The compound used in the disclosure realizes a higher T1 compared to HTM-2. In addition, the compound used in the present disclosure has a value greater than T1 of tris(4-methyl-2,5-diphenylpyridine)iridium (III) (compound 3-3), which is a green phosphorescent light emitting material, It has the ability to sufficiently confine excited triplet excitons.

Example 10

As shown in FIG. 1, the organic EL element is formed on a glass substrate 1 with an ITO electrode as a transparent anode 2 in advance, a hole injection layer 3, a first hole transport layer 4, and 2 The hole transport layer 5, the light-emitting layer 6, the electron transport layer 7, the electron injection layer 8, and the cathode (aluminum electrode) 9 were deposited in this order to produce.

Specifically, after performing ultrasonic cleaning for 20 minutes in isopropyl alcohol, the glass substrate 1 on which the ITO film with a film thickness of 150 nm was formed was dried for 10 minutes on a hot plate heated to 200°C. Thereafter, after performing UV ozone treatment for 15 minutes, this glass substrate with ITO was mounted in a vacuum evaporator, and the pressure was reduced to 0.001 Pa or less. Subsequently, as the hole injection layer 3 so as to cover the transparent anode 2, the compound acceptor-1 (Acceptor-1) and compound (7-3) of the following structural formula were used, and the deposition rate ratio was the acceptor-1: compound (7-3) = 3: By binary vapor deposition on the transparent anode 2 at a deposition rate of 97, the hole injection layer 3 was formed so that the film thickness was 10 nm. On this hole injection layer 3, a compound (7-3) was deposited as the first hole transport layer 4 so that the film thickness was 70 nm. On this first hole transport layer 4, as the second hole transport layer 5, the compound (1-2) of Example 2 was vapor-deposited so that the film thickness became 10 nm. On the second hole transport layer 5, the first host compound (A-19) and the second host compound (B-22) are simultaneously used as hosts as the light emitting layer 6, and the iridium compound ( 3-3) was doped with 5 wt%, and the compound was vacuum deposited so that the film thickness was 40 nm. Here, the first host compound (A-19) and the second host compound (B-22) were used in a ratio of 1:1.

Next, on the light-emitting layer 6, as the electron transport layer (7), a compound (4-78) of the following structural formula and a compound ETM-1 of the following structural formula are used, and the deposition rate ratio is compound (4-78): ETM-1 = Binary vapor deposition was performed at a vapor deposition rate of 50:50, and the electron transport layer 6 was formed so that the film thickness was 30 nm. On the electron transport layer 7, lithium fluoride was vapor-deposited as the electron injection layer 8 so as to have a film thickness of 1 nm. Finally, aluminum was deposited on the electron injection layer 8 to a thickness of 100 nm to form the cathode 9. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Formula 66]

[Formula 67]

[Formula 68]

[Formula 69]

[Formula 70]

[Formula 71]

[Formula 72]

[Formula 73]

Example 11

In Example 10, an organic EL device was produced in the same manner as the material of the electron transport layer 7 except that the compound (6-1) was used instead of the compound (4-78). For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Formula 74]

Example 12

In Example 10, an organic EL device was fabricated in the same manner as in Example 3 except that the compound (1-3) of Example 3 was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer (5). I did. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Formula 75]

Example 13

In Example 12, an organic EL device was produced in the same manner as the material for the electron transport layer 7 except that the compound (6-1) was used instead of the compound (4-78). For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Example 14

In Example 10, an organic EL device was fabricated in the same manner as in Example 4 except that the compound (1-4) of Example 4 was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer (5). I did. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Formula 76]

Example 15

In Example 14, an organic EL device was produced in the same manner as the material of the electron transport layer 7 except that the compound (6-1) was used instead of the compound (4-78). For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Example 16

In Example 10, an organic EL device was produced in the same manner as the second host material, except that the compound (1-2) of Example 2 was used instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-2) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Example 17

In Example 11, an organic EL device was manufactured in the same manner as the second host material, except that the compound (1-2) of Example 2 was used instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-2) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Example 18

In Example 12, an organic EL device was fabricated in the same manner as the second host material, except that the compound (1-3) of Example 3 was used instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-3) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Example 19

In Example 13, an organic EL device was fabricated in the same manner as the second host material, except that the compound (1-3) of Example 3 was used instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-3) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Example 20

In Example 14, an organic EL device was fabricated in the same manner as the second host material, except that the compound (1-4) of Example 4 was used instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-4) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Example 21

In Example 15, an organic EL device was fabricated in the same manner as the second host material, except that the compound (1-4) of Example 4 was used instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-4) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Comparative Example 1]

For comparison, in Example 10, an organic EL device was fabricated in the same manner as in Example 10, except that the compound (HTM-2) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer (5). I did. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Formula 77]

[Comparative Example 2]

For comparison, in Example 11, an organic EL device was fabricated in the same manner as in Example 11 except that the compound (HTM-2) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer 5 I did. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Comparative Example 3]

For comparison, in Example 10, an organic EL was carried out in the same manner as in Example 10, except that the compound (B-22) of the following structural formula was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer (5). The device was fabricated. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Formula 78]

[Comparative Example 4]

For comparison, in Example 11, an organic EL device was fabricated in the same manner as in Example 11 except that the compound (B-22) was used instead of the compound (1-2) of Example 2 as the material of the second hole transport layer (5). I did. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Comparative Example 5]

For comparison, in Example 14, compound (HTM-2) was used instead of compound (1-2) of Example 2 as the material of the second hole transport layer 5, and Example 2 was used as the second host material. An organic EL device was fabricated in the same manner except for using the compound (HTM-2) in place of the compound (1-2) of. Here, the first host compound (A-19) and the second host compound (HTM-2) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

[Comparative Example 6]

For comparison, in Example 15, compound (HTM-2) was used instead of compound (1-2) of Example 2 as a material of the second hole transport layer 5, and Example 2 was used as the second host material. An organic EL device was fabricated in the same manner except for using the compound (HTM-2) in place of the compound (1-2) of. Here, the first host compound (A-19) and the second host compound (HTM-2) were used in a ratio of 1:1. For the prepared organic EL device, characteristics were measured in air and at room temperature. Table 1 shows the measurement results of the luminescence characteristics when a direct voltage is applied to the prepared organic EL device.

Using the organic EL devices produced in Examples 10 to 21 and Comparative Examples 1 to 6, the results of measuring the device life were put together in Table 1 and shown. The device life is equivalent to 95% when the luminance (initial luminance) at the start of light emission is 10000 ㏅/m2 and constant current driving is performed, and the luminance is 9500 ㏅/m2 (the initial luminance is 100%): 95% attenuation) was measured as the time until attenuation.

As shown in Table 1, Examples 10 to 15 each using the arylamine compound of the present disclosure as a second hole transport material, and the compound (HTM-2) and the compound (B-22) were used as a second hole transport material. In comparison with Comparative Examples 1 to 4 respectively used as examples, the luminous efficiency when a current having a current density of 10 mA/cm 2 was passed was compared to 72.06 to 73.03 ㏅/A of the organic EL elements of Comparative Examples 1 to 4 in Examples. In the organic EL devices of 10-15, it was high efficiency at 76.05-78.00 ㏅/A. In addition, in terms of power efficiency, it was high efficiency of 57.31 to 58.99 lm/W in the organic EL devices of Examples 10 to 15 compared to 52.00 to 53.27 lm/W of the organic EL devices of Comparative Examples 1 to 4. On the other hand, in terms of the device life (95% attenuation), in the organic EL devices of Comparative Examples 1 to 4, it was 341 to 400 hours, while the organic EL devices of Examples 10 to 15 were 461 to 585 hours. I can see that there is.

As shown in Table 1, Examples 16 to 21 in which the arylamine compound of the present disclosure was used as a second hole transport material and a second host material, and the compound (HTM-2) was used as a second hole transport material and a second host. In comparison with Comparative Examples 5 and 6 used as materials, and Comparative Examples 3 and 4 using the compound (B-22) as the second hole transport material and the second host material, a current having a current density of 10 mA/cm 2 was passed. The luminous efficiency at this time was high efficiency of 73.98 to 76.04 ㏅/A in the organic EL devices of Examples 16 to 21, compared to 63.74 to 73.03 ㏅/A of the organic EL devices of Comparative Examples 3 to 6. Moreover, in terms of power efficiency, it was high efficiency of 55.53 to 56.32 lm/W in the organic EL devices of Examples 16 to 21, compared to 45.93 to 53.27 lm/W of the organic EL devices of Comparative Examples 3 to 6. On the other hand, in terms of the device life (95% attenuation), the organic EL device of Comparative Examples 3 to 6 was 309 to 384 hours, whereas the organic EL device of Examples 16 to 21 was 408 to 480 hours. I can see that there is.

As is evident from the results of Table 1, as an organic EL device comprising a light emitting layer in which a first host material having a high electron transport ability and a second host material having a hole transport ability are used together, the arylamine compound of the present disclosure is used as a second hole. It has been found that the organic EL device used as the material for the transport layer can achieve improved power efficiency and longer life even when compared with the organic EL device using the compound (HTM-2) which is an arylamine compound similarly. This is due to the fact that the arylamine compound of the present disclosure has a value greater than T1 of HTM-2. The organic EL device using the arylamine compound of the present disclosure was able to sufficiently confine the triplet excitons excited in the light emitting layer as compared to the organic EL device using HTM-2. As a result, an organic EL device having improved efficiency characteristics and remarkably improved life characteristics has been realized. Further, even when compared with an organic EL device in which the compound (B-22), which is a carbazole derivative, was used as a material for the second hole transport layer, it was found that the improvement in power efficiency and long life could be achieved. By combining the arylamine compound having a specific structure, holes are efficiently supplied to the light-emitting layer, and electron excess in the light-emitting layer is improved. As a result, an organic EL device in which the carrier balance in the light emitting layer is further stabilized and the efficiency characteristics are improved and the life characteristics are significantly improved is realized.

In addition, in the organic EL device using the arylamine compound of the present disclosure as the second host material, even when compared with the organic EL device using the compound (HTM-2), which is an arylamine compound, it is possible to improve power efficiency and increase the lifespan. I could see what I could achieve. The arylamine compound of the present disclosure has a value greater than T1 of the compound (Compound 3-3), which is a green phosphorescent light-emitting material, and was able to sufficiently confine excited triplet excitons even when used as a second host material. On the other hand, in HTM-2, T1 was low, and the triplet excitons were insufficiently confined, and the excited triplet excitons were deactivated, so that the luminous efficiency and the device lifetime were greatly reduced. Further, it was found that even when compared with the compound (B-22), which is a carbazole derivative, an improvement in power efficiency and a longer life can be achieved. By combining a specific arylamine compound having excellent electrical durability and excellent hole transporting ability, holes are efficiently supplied to the light-emitting layer, and an excess of electrons in the light-emitting layer is improved. As a result, the carrier balance in the light emitting layer is further stabilized, and an organic EL device in which the efficiency characteristics are improved and the life characteristics are significantly improved is realized.

In addition, this application is based on the Japanese patent application (Japanese Patent Application No. 2017-233148) for which it applied on December 5, 2017, The whole is used by reference. Also, all references cited herein are taken as a whole.

Although the present invention has been described in detail with reference to specific aspects, it is clear to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present invention.

Industrial availability

The organic EL device of the present invention has improved luminous efficiency and significantly improved durability, and can be developed, for example, in home telephone products and lighting applications.

1: glass substrate
2: transparent anode
3: hole injection layer
4: first hole transport layer
5: second hole transport layer
6: light-emitting layer
7: electron transport layer
8: electron injection layer
9: cathode

Claims (9)

Between the anode and the cathode, at least one of the layers disposed between the first hole transport layer and the electron transport layer, comprising at least a first hole transport layer, a second hole transport layer, a green light emitting layer, and an electron transport layer in this order from the anode side Silver is an organic EL device containing an arylamine compound represented by the following general formula (1).

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ may be the same or different, respectively, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation c Represents a cyclic aromatic group, and R ₁ , R ₂ , R ₃ may each be the same or different, and the number of carbon atoms from which each may have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a substituent is 1 to 6 linear or branched alkyl group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituent group A linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted A substituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.) Between the anode and the cathode, at least one of the layers disposed between the first hole transport layer and the electron transport layer, comprising at least a first hole transport layer, a second hole transport layer, a green light emitting layer, and an electron transport layer in this order from the anode side Silver, an organic EL device containing an arylamine compound represented by the following general formula (2).

(In the formula, Ar ₁ and Ar ₂ may be the same or different from each other, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and Ar ₅ and Ar ₆ may be the same or different from each other, and represent a phenyl group, a biphenylyl group, a naphthyl group, a phenanthrenyl group, or a fluorenyl group, and R ₄ is a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group , A nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, and 2 to carbon atoms which may have a substituent 6 linear or branched alkenyl group, a linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent, and a cycloalkyl oxy group having 5 to 10 carbon atoms which may have a substituent It represents a time period, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.) The method according to claim 1 or 2,
The green emission layer includes a host and a phosphorescent dopant, and the host includes at least one first host compound represented by the following general formula Host-A and at least one second type represented by the following general formula Host-B. An organic EL device containing a host compound.

(In the above Host-A, Z is each independently N or CRa, at least one of Z is N, and R ₅ to R ₁₄ and Ra are each independently a hydrogen atom, a deuterium atom, a fluorine atom, A chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms forming a ring, and a 6 atom substituted with a triphenylene group in Host-A The total number of rings is 6 or less, L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and n1 to n3 are each independently , 0 or 1, and n1 + n2 + n3 ≥ 1.)

(In Host-B, Y is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, and Ar ₇ is substituted Or an unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, and R ₁₅ to R ₁₈ are each independently a hydrogen atom, a deuterium atom, or a fluorine atom , A chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 4 to 50 ring carbon atoms, At least one of R ₁₅ to R ₁₈ and Ar ₇ includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazolyl group.) The method according to any one of claims 1 to 3,
The green light-emitting layer includes a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex containing iridium. The method according to any one of claims 1 to 3,
The green light-emitting layer includes a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex represented by the following general formula (3).

(In the formula, R ₁₉ to R ₃₄ may each be the same or different, and a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent , A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a 1 to 6 carbon atom which may have a substituent A linear or branched alkyloxy group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a trimethylsilyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group , A substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, or a disubstituted amino group substituted by a group selected from the group consisting of an aromatic hydrocarbon group, an aromatic heterocyclic group and a condensed polycyclic aromatic group n represents the integer of 1-3.) The method according to any one of claims 1 to 5,
The organic EL device, wherein the electron transport layer contains a compound having a pyrimidine structure represented by the following general formula (4).

(In the formula, Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, and Ar ₉ and Ar ₁₀ may be the same as or different from each other, and a hydrogen atom, substituted or unsubstituted A substituted aromatic hydrocarbon group or a substituted or unsubstituted condensed polycyclic aromatic group is represented, and B represents a monovalent group represented by the following structural formula (5): Here, Ar ₉ and Ar ₁₀ do not simultaneously become hydrogen atoms. )

(In the formula, Ar ₁₁ represents a substituted or unsubstituted aromatic heterocyclic group, and R ₃₅ to R ₃₈ may be the same or different, respectively, and a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a tri A fluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group Show.) The method according to any one of claims 1 to 5,
The organic EL device, wherein the electron transport layer contains a compound having a benzoazole structure represented by the following general formula (6).

(In the formula, Ar ₁₂ and Ar ₁₃ may be the same or different from each other, a hydrogen atom, a deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted Represents an aromatic heterocyclic group, V ₁ is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aromatic heterocyclic group, and the number of carbon atoms which may have 1 to 6 substituents Represents a linear or branched alkyl group of, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, or a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, X represents an oxygen atom or a sulfur atom, and W ₁ and W ₂ may be the same as or different from each other, and represent a carbon atom or a nitrogen atom.) The method according to any one of claims 1 to 7,
The organic EL device, wherein the first hole transport layer contains a triphenylamine derivative represented by the following general formula (7) or (8).

(In the formula, R ₃₉ to R ₄₄ are each independently a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent. , A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a C 1 to 6 carbon atom which may have a substituent A linear or branched alkyloxy group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted Represents a substituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, r ₁ to r ₆ may be the same or different, respectively, r ₁ to r ₄ represents an integer of 0 to 5, r ₅ , r ₆ represents an integer of 0 to 4. When r ₁ to r ₆ are an integer of 2 or more, R ₃₉ to R ₄₄ bonded to a plurality of the same benzene ring may be the same or different, respectively. Substituents substituted with a ring are substituted with a plurality of substituents with the same benzene ring, and benzene rings adjacent to each other via a nitrogen atom are each attached to a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. K ₁ represents a divalent group represented by the following structural formulas (HTM-A) to (HTM-F) or a single bond.)

(In formula, j represents the integer of 1-3.)

(In the formula, R ₄₅ to R ₅₆ are each independently a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent. , A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a C 1 to 6 carbon atom which may have a substituent A linear or branched alkyloxy group, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted Represents a substituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group, r ₇ to r ₁₈ may be the same or different, respectively, r ₇ to r ₁₂ represent an integer of 0 to 5, and r ₁₃ to r ₁₈ represents an integer of 0 to 4. When r ₇ to r ₁₈ is an integer of 2 or more, a plurality of R ₄₅ to R ₅₆ bonded to the same benzene ring may be the same or different, respectively. Substituents substituted with a ring are substituted with a plurality of substituents with the same benzene ring, and benzene rings adjacent to each other via a nitrogen atom are each attached to a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. K ₂ to K ₄ may be the same or different, respectively, and a divalent group represented by (HTM-A) to (HTM-F) described in General Formula (7), or a single bond Represents.) The arylamine compound represented by the following general formula (1).

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ may be the same or different, respectively, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation c Represents a cyclic aromatic group, and R ₁ , R ₂ , R ₃ may each be the same or different, and the number of carbon atoms from which each may have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a substituent is 1 to 6 linear or branched alkyl group, a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituent group A linear or branched alkyloxy group having 1 to 6 carbon atoms, which may have a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted A substituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

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