JP7163311B2 - organic electroluminescence element - Google Patents

Description

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 the device. The present invention relates to an organic EL device using the compound.

Since the organic EL element is a self-luminous element, it is brighter than a liquid crystal element, has excellent visibility, and can display a clear image.

In 1987, Eastman Kodak Company's C.I. W. Tang et al. have made practical an organic EL element using organic materials by developing a layered structure element in which each material plays a role. They layered a phosphor, tris(8-hydroxyquinoline)aluminum (hereafter abbreviated as Alq3) _, which can transport electrons, and an aromatic amine compound, which can transport holes, and both charge was injected into the phosphor layer to emit light, a high luminance of 1000 cd/m ² or more was obtained at a voltage of 10 V or less (see, for example, Patent Documents 1 and 2).

Until now, many improvements have been made for the practical use of organic EL devices. High efficiency and durability have been achieved by electroluminescent devices provided with a layer, an electron injection layer, and a cathode (see, for example, Non-Patent Document 1).

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

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

Furthermore, by using both a compound having a nitrogen-containing heteroaromatic ring structure with high electron-transporting ability and a compound having a carbazole structure with hole-transporting ability as a host, electrons and The hole transportability is enhanced and the luminous efficiency is remarkably improved (see, for example, Patent Documents 4 and 5).

As a hole-transporting material and a host material having a hole-transporting ability that have been used in phosphorescent organic EL devices, carbazole derivatives (for example, HTM-1 below) disclosed in Patent Document 6 are known. was Carbazole derivatives have a high triplet energy level (hereinafter abbreviated as T1) and are excellent in the ability to confine triplet excitons, but have problems of low hole mobility and resistance to electrical reduction. Therefore, when combined with a light-emitting layer having improved electron-transporting ability, the supply of holes to the light-emitting layer becomes rate-determining, resulting in an excess of electrons in the light-emitting layer. There is concern about shortening the service life.

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

However, although these monoamine compounds have higher hole mobility than carbazole derivatives, they have a problem of low T1. As a result, the confinement of triplet excitons becomes insufficient, and there are concerns about a decrease in luminous efficiency due to exciton deactivation and a shortened life of the device. Therefore, there has been a demand for a hole-transporting material and a host material that have high hole mobility and excellent confinement of triplet excitons.

Japanese Patent Laid-Open No. 8-048656 Japanese Patent Laid-Open No. 7-126615 Japanese Patent Application Laid-Open No. 2006-151979 WO2015/034125 WO2016/013732 Japanese Patent Laid-Open No. 8-003547 Japanese Patent Application Laid-Open No. 2006-352088 International Publication No. 2017/099155 Japanese Patent Application Laid-Open No. 2002-105055 WO2014/007565 WO2014/188947 WO2015/190400 Japanese Patent Application Publication No. 2010-83862 WO2015/038503 Japanese Patent Application Laid-Open No. 2005-108804 International Publication No. 2008/62636 WO2014/009310

Proceedings of the 9th seminar of the Japan Society of Applied Physics, pp.55-61 (2001) Proceedings of the 9th seminar of the Japan Society of Applied Physics, pp.23-31 (2001) Synth. Commun. , 11, 513 (1981)

An object of the present invention is to provide a material for highly efficient and highly durable organic EL devices that has excellent hole injection and transport performance, electron blocking capability, high stability in a thin film state, and high luminous efficiency. An object of the present invention is to provide an organic compound having excellent properties, and to provide an organic EL device with high efficiency and high durability using this compound.

The physical properties that the organic compound to be provided by the present invention should have are (1) good hole injection properties, (2) high hole mobility, and (3) electron blocking ability. (4) a stable thin film state; and (5) excellent durability against electrons. Further, the physical properties that the organic EL device to be provided by the present invention should have include (1) high luminous efficiency and (2) long device life.

Therefore, in order to achieve the above object, the present inventors have expected that the aromatic tertiary amine structure has high hole injection and transport ability, and that it is effective for electrical durability and thin film stability. Then, a monoamine compound having a novel triarylamine structure was designed and chemically synthesized, various organic EL devices were fabricated using the compound, and the characteristics of the devices were thoroughly evaluated. As a result, the present invention was completed. reached.

The organic EL device of the present invention, which can solve 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 the first hole transport layer and the At least one layer among the layers arranged between the electron transport layer contains an arylamine compound represented by the following general formula (1).

(wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted represents a condensed polycyclic aromatic group, R ₁ , R ₂ and R ₃ may be the same or different and have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group and a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, 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 be optionally substituted, 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, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or represents a substituted or unsubstituted aryloxy group.)

Another organic EL device of the present invention that can solve the above problems is
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 the first hole-transport layer and the At least one layer among the layers arranged between the electron transport layer contains an arylamine compound represented by the following general formula (2).

(In the formula, Ar ₁ and Ar ₂ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted condensed polycyclic aromatic Ar ₅ and Ar ₆ , which may be the same or different, represent a phenyl group, biphenylyl group, naphthyl group, phenanthrenyl group, or fluorenyl group; R ₄ represents a hydrogen atom, a deuterium atom, a fluorine atom; , a chlorine atom, a cyano group, a nitro group, an optionally substituted C 1 to 6 linear or branched alkyl group, an optionally substituted C 5 to 10 cycloalkyl group, optionally substituted C2-C6 linear or branched alkenyl group, optionally substituted C1-C6 linear straight or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic ring group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

Further, the arylamine compound of the present invention, which can solve the above problems, is represented by the following general formula (1).

(wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted represents a condensed polycyclic aromatic group, R ₁ , R ₂ and R ₃ may be the same or different and have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group and a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, 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 be optionally substituted, 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, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or represents a substituted or unsubstituted aryloxy group.)

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

FIG. 10 is a diagram showing EL element configurations of Examples 10 to 21 and Comparative Examples 1 to 6;

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, embodiments of the present invention will be described in detail. First, the arylamine compound and the organic EL device of the present embodiment will be described by enumerating aspects thereof. In the present application, the term "not" is a term indicating a range. For example, the description "5 to 10" means "5 or more and 10 or less", and represents a range including the numerical values 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 the first hole-transport layer and the An organic EL device, wherein at least one of the layers disposed between the electron-transporting layer contains an arylamine compound represented by the following general formula (1).

(wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted represents a condensed polycyclic aromatic group, wherein R ₁ , R ₂ and R ₃ may be the same or different and have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group and a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, 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 be substituted, 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, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or represents 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 the first hole-transport layer and the An organic EL device, wherein at least one of the layers disposed between the electron-transporting layer contains an arylamine compound represented by the following general formula (2).

(In the formula, Ar ₁ and Ar ₂ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted condensed polycyclic aromatic Ar ₅ and Ar ₆ , which may be the same or different, each represent a phenyl group, biphenylyl group, naphthyl group, phenanthrenyl group, or fluorenyl group; R ₄ represents a hydrogen atom, a deuterium atom, a fluorine atom; , a chlorine atom, a cyano group, a nitro group, an optionally substituted C 1 to 6 linear or branched alkyl group, an optionally substituted C 5 to 10 cycloalkyl group, optionally substituted C2-C6 linear or branched alkenyl group, optionally substituted C1-C6 linear straight or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic ring group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

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

(In Host-A, Z is each independently N or CRa, at least one of Z is N, R ₅ to R ₁₄ and Ra are each independently hydrogen atoms , 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 ring-forming carbon atoms, The total number of 6-membered rings substituted by triphenylene groups in Host-A is 6 or less, and L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted tertiary a phenylene group, 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 a substituted or 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 hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted ring It is a heteroaryl group having 4 to 50 carbon atoms, and 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 emitting layer contains a host and a phosphorescent dopant, and the phosphorescent dopant is a metal complex containing iridium.

5) 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 represented by the following general formula (3): The described organic EL device.

(Wherein, R ₁₉ to R ₃₄ may be the same or different, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, or an optionally substituted linear chain having 1 to 6 carbon atoms. Alternatively, a branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, or an optionally substituted linear or branched C 2 to 6 alkenyl group, optionally substituted C1-C6 linear or branched alkyloxy group, optionally substituted C5-C10 cycloalkyloxy group , 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 an aromatic represents a disubstituted amino group substituted with a group selected from the group consisting of a hydrocarbon group, an aromatic heterocyclic group and a condensed polycyclic aromatic group, n represents an integer of 1 to 3.)

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

(wherein Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted condensed polycyclic aromatic group; Ar ₉ and Ar ₁₀ may be the same or different; represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, and B represents a monovalent group represented by the following structural formula (5), wherein Ar ₉ and Ar ₁₀ cannot be hydrogen atoms at the same time.)

(wherein Ar ₁₁ represents a substituted or unsubstituted aromatic heterocyclic group, R ₃₅ to R ₃₈ may be the same or different, hydrogen atom, deuterium atom, fluorine atom, chlorine atom, a cyano group, a trifluoromethyl 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 represents an unsubstituted condensed polycyclic aromatic group.)

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

(In the formula, Ar ₁₂ and Ar ₁₃ may be the same or different, and are hydrogen atom, deuterium atom, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted condensed polycyclic aromatic group, or represents a substituted or unsubstituted aromatic heterocyclic group, and 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 , an optionally substituted C 1-6 linear or branched alkyl group, an optionally substituted C 5-10 cycloalkyl group, or a substituent represents a _linear or branched alkenyl group having ₂ to 6 carbon atoms optionally having It often represents a carbon atom or a nitrogen atom.)

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

(In the formula, R ₃₉ to R ₄₄ each independently deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, optionally substituted linear chain having 1 to 6 carbon atoms linear or branched alkyl group, optionally substituted cycloalkyl group having 5 to 10 carbon atoms, linear or branched chain having 2 to 6 carbon atoms optionally having substituent(s) alkenyl group, optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy having 5 to 10 carbon atoms r ₁ represents a group, 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. to r ₆ may be the same or different, r ₁ to r ₄ represent integers of 0 to 5, r ₅ and r ₆ represent integers of 0 to 4. r ₁ to r ₆ are 2 or more; When it is an integer, the plurality of R ₃₉ to R ₄₄ bonded to the same benzene ring may be the same or different, and the benzene ring and the substituents substituted on the benzene ring are Multiple substituted substituents and benzene rings adjacent to each other via a nitrogen atom may be bonded to each other by a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. K ₁ represents a divalent group represented by the following structural formulas (HTM-A) to (HTM-F), or a single bond.)

(Wherein, j represents an integer of 1 to 3.)

(In the formula, R ₄₅ to R ₅₆ each independently deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, optionally substituted linear chain having 1 to 6 carbon atoms linear or branched alkyl group, optionally substituted cycloalkyl group having 5 to 10 carbon atoms, linear or branched chain having 2 to 6 carbon atoms optionally having substituent(s) alkenyl group, optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy having 5 to 10 carbon atoms r ₇ represents a group, 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. to r ₁₈ may be the same or different, r ₇ to r ₁₂ each represent an integer of 0 to 5, and r ₁₃ to r ₁₈ each represent an integer of 0 to 4. r ₇ to r ₁₈ are 2 or more; When it is an integer, the plurality of R ₄₅ to R ₅₆ bonded to the same benzene ring may be the same or different, and the benzene ring and the substituents substituted on the benzene ring are Multiple substituted substituents and benzene rings adjacent to each other via a nitrogen atom may be bonded to each other by a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. K ₂ to K ₄ may be the same or different, and each represents a divalent group represented by (HTM-A) to (HTM-F) in general formula (7), or a single bond.)

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

(wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted represents a condensed polycyclic aromatic group, wherein R ₁ , R ₂ and R ₃ may be the same or different and have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group and a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, 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 be substituted, 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, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or represents a substituted or unsubstituted aryloxy group.)

A “substituted or unsubstituted aromatic hydrocarbon group”, a “substituted or unsubstituted aromatic heterocyclic group” or a “substituted or unsubstituted condensed polycyclic group” represented by Ar ₁ to Ar ₄ in the general formula (1) Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the ring aromatic group include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, anthracenyl group, phenanthrenyl group, 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, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group , and carbonyl groups.

As the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar ₁ to Ar ₄ in general formula (1), , specifically, deuterium atom, cyano group, nitro group; fluorine atom, chlorine atom, bromine atom, halogen atom such as iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, Linear or branched alkyl groups having 1 to 6 carbon atoms such as isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl; methyloxy, ethyloxy, propyl linear or branched alkyloxy group having 1 to 6 carbon atoms such as oxy group; alkenyl group such as vinyl group and allyl group; aryloxy group such as phenyloxy group and tolyloxy group; benzyloxy group and phenethyloxy group Arylalkyloxy groups such as phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, and triphenylenyl groups. Hydrogen 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, benzoxazolyl aromatic heterocyclic groups such as aryl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl and carbonyl groups; arylvinyl groups such as styryl and naphthyvinyl; acetyl and benzoyl A group such as an acyl group such as a group may be mentioned, and these substituents may be further substituted with the substituents exemplified above. Further, these substituents may be bonded to each other through 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", "having a substituent "Optionally substituted C5-C10 cycloalkyl group" or "C2-C6 linear or branched alkenyl group optionally having 6 straight-chain or branched alkyl group", "C5-C10 cycloalkyl group" or "C2-C6 straight-chain or branched alkenyl group" are 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., and these groups are single bonds, substituted or unsubstituted methylene groups, oxygen atoms or They may be bonded to each other through a sulfur atom to form a ring.

"A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "a linear or branched alkyl group having 5 to 10 carbon atoms having a substituent" represented by R ₁ to R ₃ in the general formula (1) The "substituent" in "a cycloalkyl group of" or "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent" specifically includes a deuterium atom, a cyano group, a nitro group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group and allyl aryloxy groups such as phenyloxy group and tolyloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl 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, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group These substituents may be further substituted with the substituents exemplified above. Further, these substituents may be bonded to each other through 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 optionally having a substituent” or “having a substituent” represented by R ₁ to R ₃ in the general formula (1) "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 having 5 to 10 carbon atoms which may be ” specifically includes 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., and these groups are single bonds, substituted or unsubstituted methylene groups, oxygen They may also be attached to each other via an atom or a sulfur atom to form a ring.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent" or "C5 to 5 having a substituent" represented by R ₁ to R ₃ in the general formula (1) The “substituent” in the cycloalkyloxy group of 10” includes the “substituted linear or branched C 1 to 6 substituent represented by R ₁ to R ₃ in the general formula (1). with respect to the "substituent" in "alkyl group of", "substituted C5-C10 cycloalkyl group" or "substituted C2-C6 linear or branched alkenyl group" The same ones as those shown can be given, and the same possible modes can be given.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic group” represented by R ₁ to R ₃ in general formula (1) The "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "aromatic ring group" are represented by Ar ₁ to Ar ₄ in the above general formula (1). "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" The same groups as those shown for "heterocyclic group" or "condensed polycyclic aromatic group" can be mentioned, and these groups have a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. may be bonded to each other via to form a ring. In addition, these groups may have a substituent, and examples of the substituent include the “substituted aromatic hydrocarbon group” and the “substituted aromatic heterohydrocarbon group” represented by Ar ₁ to Ar ₄ in the general formula (1). The same examples as those shown for the "substituent" in the "cyclic group" or the "substituted condensed polycyclic aromatic group" can be given, and the same examples can be given as possible embodiments.

Specific examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R ₁ to R ₃ in general formula (1) include a phenyloxy group, a biphenylyloxy group, a terphenyloxy lyloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group and the like. They may be bonded to each other via a 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 examples of the substituent include the “substituted aromatic hydrocarbon group” and the “substituted aromatic heterohydrocarbon group” represented by Ar ₁ to Ar ₄ in the general formula (1). The same examples as those shown for the "substituent" in the "cyclic group" or the "substituted condensed polycyclic aromatic group" can be given, and the same examples can be given as possible embodiments.

Ar ₁ and Ar ₂ in the general formula (1) are preferably a "substituted or unsubstituted aromatic hydrocarbon group" or a "substituted or unsubstituted condensed polycyclic aromatic group", such as a phenyl group and a naphthyl group. , a phenanthrenyl group and a fluorenyl group are more preferable, and a phenyl group having a substituent and a fluorenyl group having a substituent are particularly preferable. Preferred substituents for the phenyl group are phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl and fluorenyl groups, and preferred substituents for the fluorenyl group are methyl and phenyl. Ar ₃ and Ar ₄ in the general formula (1) are preferably a "substituted or unsubstituted aromatic hydrocarbon group" or a "substituted or unsubstituted condensed polycyclic aromatic group", a phenyl group, a biphenylyl group, A naphthyl group, a phenanthrenyl group and a fluorenyl group are more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group and a substituted fluorenyl group are more preferable. Here, as a substituent of the fluorenyl group, a methyl group and a phenyl group are preferable.

R ₁ and R ₃ in general formula (1) are preferably a hydrogen atom or a deuterium atom, and more preferably a hydrogen atom from the viewpoint of synthesis.
R ₂ in the general formula (1) is preferably a "substituted or unsubstituted aromatic hydrocarbon group" or a "substituted or unsubstituted condensed polycyclic aromatic group", a phenyl group, a biphenylyl group, a naphthyl group, A phenanthrenyl group and a fluorenyl group are more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group, and a substituted fluorenyl group are more preferable. Here, as a substituent of the fluorenyl group, a methyl group and a phenyl group are preferable.

"A linear or branched alkyl group having 1 to 6 carbon atoms optionally having a substituent" represented by R ₄ in the general formula (2), "Even if it has a substituent "Good C5-C10 cycloalkyl group" or "C2-C6 linear or branched alkenyl group optionally having substituent(s)" A chain or branched alkyl group", a "C5-C10 cycloalkyl group" or a "C2-C6 linear or branched alkenyl group" specifically includes a 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" and "cycloalkyl having 5 to 10 carbon atoms having a substituent" represented by R ₄ in the general formula (2) The "substituent" in the "group" or "substituted linear or branched alkenyl group having 2 to 6 carbon atoms" specifically includes a deuterium atom, a cyano group, a nitro group; a fluorine atom, halogen atoms such as chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group, allyl group and the like alkenyl groups; aryloxy groups such as phenyloxy and tolyloxy; arylalkyloxy groups such as benzyloxy and phenethyloxy; phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl aromatic groups such as radicals, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbolinyl Groups such as heterocyclic groups can be mentioned.

An “optionally substituted C 1 to 6 linear or branched alkyloxy group” represented by R ₄ in the general formula (2) or “having a substituent As the "linear or branched alkyloxy group having 1 to 6 carbon atoms" or the "cycloalkyloxy group having 5 to 10 carbon atoms" in "a cycloalkyloxy group having 5 to 10 carbon atoms" , specifically, 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 and the like.

"A linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent" or "a cyclo having ₅ to 10 carbon atoms having a The “substituent” in the “alkyloxy group” includes “a linear or branched alkyl group having 1 to 6 carbon atoms and having a substituent represented by R ₁ to R ₃ in the above general formula (1). ", "substituted C5-C10 cycloalkyl group" or "substituted C2-C6 linear or branched alkenyl group" The same can be given as examples, and the same possible modes can be given.

"Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" represented by R ₄ in general formula (2) The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the above general formula _{( 1} ) includes the “substituted or "Unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group""aromatic hydrocarbon group", "aromatic heterocyclic ring The same examples as those shown with respect to "group" or "condensed polycyclic aromatic group" can be mentioned. In addition, these groups may have a substituent, and examples of the substituent include the “substituted aromatic hydrocarbon group” and the “substituted aromatic heterohydrocarbon group” represented by Ar ₁ to Ar ₄ in the general formula (1). The same examples as those shown for the "substituent" in the "cyclic group" or the "substituted condensed polycyclic aromatic group" can be given, and the same examples can be given as possible embodiments.

Specific examples of the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R ₄ in general formula (2) include a phenyloxy group, a biphenylyloxy group, and a terphenylyloxy group. , naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group and perylenyloxy group. In addition, these groups may have a substituent, and examples of the substituent include the “substituted aromatic hydrocarbon group” and the “substituted aromatic heterohydrocarbon group” represented by Ar ₁ to Ar ₄ in the general formula (1). The same examples as those shown for the "substituent" in the "cyclic group" or the "substituted condensed polycyclic aromatic group" can be given, and the same examples can be given as possible embodiments.

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

Ar ₁ and Ar ₂ in general formula (2) are the same as Ar ₁ and Ar ₂ in general formula (1) above.

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

Specific examples of 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) include methyl group, ethyl group and 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-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-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-diamino ethyl 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 and the like.

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 general formula (HOST-A) includes "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 The same ones as those shown with respect to the "substituent" in the "substituted C2-C6 linear or branched alkenyl group" can be mentioned, and the same examples can be taken. I can give

Specific examples of the "substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms" represented by R ₅ to R ₁₄ and Ra in the general formula (HOST-A) include a phenyl group, a 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, nitro biphenylyl group, cyanobiphenyl group, cyanonaphthyl group, nitronaphthyl group, fluoronaphthyl group and the like. Among the above, a phenyl group or a biphenylyl group is particularly preferred.

As the “substituent” in the “substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms” represented by R ₅ to R ₁₄ and Ra in the general formula (HOST-A), the general formula (1) The same as the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar ₁ to Ar ₄ in Things can be given, and possible modes can be given as well.

"Substituent" in "substituted or unsubstituted phenylene group", "substituted or unsubstituted biphenylene group" or "substituted or unsubstituted terphenylene group" represented by L ₁ in general formula (HOST-A) Examples of the above-mentioned general formula (1) represented by R ₁ to R ₃ are "a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "a carbon atom having a substituent Examples are the same as those shown with respect to the "substituent" in "a cycloalkyl group having 5 to 10 carbon atoms" or "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent". , and possible modes are the same.

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, 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-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-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-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-di cyanoethyl 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 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 and the like.

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) is 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 "the number of carbon atoms having a substituent The same ones as those shown with respect to the "substituent" in "2 to 6 linear or branched alkenyl groups" can be mentioned, and the same examples can be given as possible embodiments.

"Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms" or "substituted or unsubstituted 4 to 50 ring carbon atoms" represented by R ₁₅ to R ₁₈ in general formula (HOST-B) The "aryl group having 6 to 50 ring carbon atoms" or "heteroaryl group having 4 to 50 ring carbon atoms" in the "heteroaryl group of" specifically includes a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthryl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, acetonaphthenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyranyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, Examples include carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalyl, benzimidazolyl, dibenzofuranyl, and dibenzothienyl groups.

"Substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms" or "substituted or unsubstituted 4 to 50 ring carbon atoms" represented by R ₁₅ to R ₁₈ in general formula (HOST-B) As the “substituent” in the “heteroaryl group of”, the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed group” represented by Ar ₁ to Ar ₄ in the general formula (1) The same ones as those shown with respect to the "substituent" in the "polycyclic aromatic group" can be mentioned, and the same examples can be mentioned as possible embodiments.

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" represented by Y in the general formula (HOST-B) Specific examples of the "arylene group having 6 to 30 ring carbon atoms" or "heteroarylene group having 5 to 30 ring carbon atoms" in " , phenanthrylene group, fluorenylene group, indenylene group, pyrenylene group, acetonaphthenylene group, fluoranthenylene group, triphenylenylene group, pyridylene group, pyranylene group, quinolylene group, isoquinolylene group, benzofuranylene group, benzothienylene group, indolylene group, carbazolylene groups, benzoxazolylene groups, benzothiazolylene groups, quinoxalylen groups, benzimidazolylene groups, pyrazolylene groups, dibenzofuranylene groups, and dibenzothienylene groups.

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" represented by Y in the general formula (HOST-B) ", the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted _{condensed polycyclic} aromatic The same ones as those shown for the "substituent" in the "group" can be mentioned, and the same examples can be mentioned as possible modes.

"Substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" or "substituted or unsubstituted heteroaryl having 5 to 30 ring carbon atoms" represented by Ar ₇ in general formula (HOST-B) Specific examples of the "aryl group having 6 to 30 ring carbon atoms" or "heteroaryl group having 5 to 30 ring carbon atoms" in "group" include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, and a biphenyl group. , p-terphenyl group, m-terphenyl group, quaterphenyl group, fluorenyl group, triphenylene group, biphenylene group, pyrenyl group, benzofluoranthenyl group, chrysenyl group, phenylnaphthyl group, naphthylphenyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuryl group, benzothienyl group, indolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group and the like.

"Substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" or "substituted or unsubstituted heteroaryl having 5 to 30 ring carbon atoms" represented by Ar ₇ in general formula (HOST-B) As the "substituent" in the "group", the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted _{condensed polycyclic} aromatic The same ones as those shown with respect to the "substituent" in the "group group" can be mentioned, and the same examples can be mentioned as possible modes.

"A linear or branched alkyl group having ₁ to 6 carbon _atoms which may have a substituent", "having a substituent "Optionally substituted cycloalkyl group having 5 to 10 carbon atoms" or "linear or branched alkenyl group having 2 to 6 carbon atoms which may be substituted", "1 to 1 6 straight-chain or branched alkyl group", "C5-C10 cycloalkyl group" or "C2-C6 straight-chain or branched alkenyl group" are 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, Examples include 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, isopropenyl group and 2-butenyl group. Also, 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", "having a substituent as a "substituent" in "optionally substituted C5-C10 cycloalkyl group" or "optionally substituted C2-C6 linear or branched alkenyl group" is "a linear or branched alkyl group having ₁ to ₆ carbon atoms having a substituent", "a linear or branched alkyl group having 1 to 6 carbon atoms having a 10 to 10 cycloalkyl groups" or "substituted linear or branched C 2 to 6 alkenyl groups". The same thing can be mentioned as the aspect of the device.

“A linear or branched _alkyloxy group having ₁ to 6 carbon atoms which may have a substituent” or “a "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 having 5 to 10 carbon atoms which may be ” specifically includes 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 and the like.

"A linear or branched _alkyloxy group having ₁ to 6 carbon atoms having a substituent" or "a substituted C 5 to The “substituent” in the cycloalkyloxy group of 10” includes the “substituted linear or branched C 1 to 6 substituent represented by R ₁ to R ₃ in the general formula (1). with respect to the "substituent" in "alkyl group of", "substituted C5-C10 cycloalkyl group" or "substituted C2-C6 linear or branched alkenyl group" The same ones as those shown can be given, and the same possible modes can be given.

Specific examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R ₁₉ to R ₃₄ in general formula (3) include a phenyloxy group, a biphenylyloxy group, a terphenyloxy lyloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group and the like. They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

The “substituent” in the “substituted or unsubstituted aryloxy group” represented by R ₁₉ to R ₃₄ in general formula (3) is represented by R ₁ to R ₃ in general formula (1). The same ones as those shown for the "substituent" in the "substituted or unsubstituted aryloxy group" can be mentioned, and the same examples can be mentioned as possible embodiments.

" _Substituted or _{unsubstituted} aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group", or "substituted or unsubstituted condensed Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "polycyclic aromatic group" include a phenyl group, a naphthyl group, an anthracenyl group, a 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 , oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, benzimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl but not limited to, a naphthyridinyl group, a benzoxazinyl group, a benzthiazinyl group, an acridinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, or a combination thereof.

" _Substituted or _{unsubstituted} aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group", or "substituted or unsubstituted condensed As the "substituent" in the " _{polycyclic aromatic} group", the "substituted aromatic hydrocarbon group", "substituted aromatic heterocyclic group" or "substituted The same ones as those shown for the "substituent" in the "condensed polycyclic aromatic group" can be mentioned, and the same examples can be mentioned as possible embodiments.

"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) , specifically, 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, 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 , a benzoxazinyl group, a benzthiazinyl group, an acridinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, or combinations thereof, but are not limited thereto. In addition, these "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" may have a substituent. ) for the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar ₁ to Ar ₄ in can be given, and possible modes can be given in the same way.

"Aromatic hydrocarbon 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) ” or “condensed polycyclic aromatic group” specifically includes 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, and an indenyl group. , pyrenyl, perylenyl, fluoranthenyl and triphenylenyl.

As the “substituent” in the “substituted aromatic hydrocarbon group” or “substituted condensed polycyclic aromatic group” represented by Ar ₈ to Ar ₁₀ in general formula (4), The same as the “substituent” 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 can be given as possible modes.

Specific examples of the "aromatic heterocyclic group" in the "substituted or unsubstituted aromatic heterocyclic group" represented by Ar ₁₁ in the structural formula (5) include a triazinyl group, a pyridyl group, a pyrimidinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group , dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl, carbolinyl.

As the “substituent” in the “substituted aromatic heterocyclic group” represented by Ar ₁₁ in the structural formula _{( 5} ), the “substituted aromatic The same as those shown with respect to the "substituent" in the "substituted aromatic heterocyclic group" or "substituted condensed polycyclic aromatic group" can be mentioned, and the possible embodiments are also the same. I can give you something.

Specific examples of the "linear or branched alkyl group having 1 to 6 carbon atoms" represented by R ₃₅ to R ₃₈ in the structural formula (5) include 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.

“ _Substituted or unsubstituted _aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "polycyclic aromatic group" include a phenyl group, a biphenylyl group, a terphenylyl group and a tetrakisphenyl group. , styryl group, naphthyl group, 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, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, Groups such as naphthyridinyl, phenanthrolinyl, acridinyl and carbolinyl groups may be mentioned.

as a “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by R ₃₅ to R ₃₈ in structural formula (5); , 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). ” can be mentioned, and the same possible modes can be mentioned.

Ar ₈ in general formula (4) includes a phenyl group, biphenylyl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group and triphenylenyl group. Phenyl group, biphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluoranthenyl group and triphenylenyl group are more preferred. Here, the phenyl group preferably has a substituted or unsubstituted condensed polycyclic aromatic group as a substituent selected from naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluoranthenyl and triphenylenyl groups. It is more preferable to have a substituent that is
Ar ₉ in the general formula (4) is preferably a phenyl group having a substituent, and the substituent in this case includes an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group and a terphenyl group, a naphthyl group, anthracenyl condensed polycyclic aromatic groups such as group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group are preferred, and phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, A pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferred.
Ar ₁₀ in the general formula (4) is preferably a phenyl group having a substituent, and the substituent in this case includes an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group and a terphenyl group, a naphthyl group, anthracenyl condensed polycyclic aromatic groups such as group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group are preferred, and phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, A pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferred.

Ar ₁₁ in structural formula (5) includes a triazinyl group, a pyridyl group, a pyrimidinyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, and a benzimidazolyl group. , a pyrazolyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbolinyl group are preferred, and a triazinyl group, a pyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a quinoxalinyl group, and a benzimidazolyl group. group, naphthyridinyl group, phenanthrolinyl group and acridinyl group are more preferred, and pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, indolyl group, quinoxalinyl group, benzimidazolyl group, phenanthrolinyl group and acridinyl group are particularly preferred.

_A "substituted or _{unsubstituted aromatic} hydrocarbon group", a "substituted or unsubstituted aromatic heterocyclic group" or a "substituted or unsubstituted The "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "condensed polycyclic aromatic group" specifically includes a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl anthracenyl group, 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, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl groups such as phenanthrolinyl, acridinyl, carbolinyl, and the like.

_A “substituted or _{unsubstituted aromatic} hydrocarbon group”, a “substituted or unsubstituted aromatic heterocyclic group” or a “substituted or unsubstituted As the “substituent” in the “condensed polycyclic aromatic group of”, the “substituted aromatic hydrocarbon group” and “substituted aromatic heterocyclic group” represented by Ar ₁ to Ar ₄ in the general formula (1) Alternatively, the same ones as those shown in relation to the "substituent" in the "substituted condensed polycyclic aromatic group" can be mentioned, and the same possible modes can be mentioned.

"Optionally substituted C 1 to C 6 linear or branched alkyl group" represented by V ₁ in the general formula (6), "Even if having a substituent "Good C5-C10 cycloalkyl group" or "C1-C6 linear or branched alkenyl group optionally having 2-6 carbon atoms" Specific examples of the linear or branched alkyl group, the "cycloalkyl group having 5 to 10 carbon atoms", or the "linear or branched alkenyl group having 2 to 6 carbon atoms" include: 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, 2-adamantyl, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

"Optionally substituted C 1 to C 6 linear or branched alkyl group" represented by V ₁ in the general formula (6), "Even if having a substituent The ``substituent'' in the ``optionally substituted cycloalkyl group having 5 to 10 carbon atoms'' or ``linear or branched alkenyl group having 2 to 6 carbon atoms which may be substituted''"A linear or branched alkyl group having ₁ to 6 carbon atoms having a substituent", "Alkyl group having ₅ to 10 carbon atoms having a The same as those shown in relation to the "substituent" in the "cycloalkyl group" or "substituted linear or branched alkenyl group having 2 to 6 carbon atoms" can be mentioned, and possible embodiments are also possible. , can give similar.

"A _linear or branched alkyl group having 1 to 6 carbon _atoms which may have a substituent", "having a substituent "Optionally substituted cycloalkyl group having 5 to 10 carbon atoms" or "linear or branched alkenyl group having 2 to 6 carbon atoms which may be substituted", "1 to 1 6 straight-chain or branched alkyl group", "C5-C10 cycloalkyl group" or "C2-C6 straight-chain or branched alkenyl group" are 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., and these groups are single bonds, substituted or unsubstituted methylene groups, oxygen atoms or They may be bonded to each other through a sulfur atom to form a ring.

"A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "C 5 to 10 having a substituent" represented by R ₃₉ to R ₄₄ in the general formula (7) The "substituent" in "a cycloalkyl group of" or "a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent" specifically includes a deuterium atom, a cyano group, a nitro group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group and allyl aryloxy groups such as phenyloxy group and tolyloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group These substituents may be further substituted with the substituents exemplified above. Further, these substituents may be bonded to each other through 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 “a "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 having 5 to 10 carbon atoms which may be ” specifically includes 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., and these groups are single bonds, substituted or unsubstituted methylene groups, oxygen They may be attached to each other through an atom or a sulfur atom to form a ring.
In addition, these groups may have a substituent, and the substituent represented by R ₃₉ to R ₄₄ in the general formula (7) may be a “straight chain group having 1 to 6 carbon atoms having a substituent”. "a linear or branched alkyl group", "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 ones as those shown in relation to the "substituent" can be mentioned, and the same examples can be mentioned as possible modes.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic group” represented by R ₃₉ to R ₄₄ in general formula (7) Specific examples of the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the ring aromatic group include phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, 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 benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group , and carbonyl groups, 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.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic group” represented by R ₃₉ to R ₄₄ in general formula (7) Specific examples of the "substituent" in the "aromatic ring group" include deuterium atom, cyano group, nitro group; fluorine atom, chlorine atom, bromine atom, halogen atom such as iodine atom; methyl group, ethyl group, n - straight or branched chain having 1 to 6 carbon atoms such as propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group and n-hexyl group; Alkyl groups of; Linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; Alkenyl groups such as vinyl group and allyl group; Phenyloxy group and Tolyloxy group Aryloxy groups such as benzyloxy group, arylalkyloxy group such as phenethyloxy group; Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as fluoranthenyl and triphenylenyl groups; pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzo Aromatic heterocyclic groups such as thienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group; styryl group, naphthyl arylvinyl groups such as a 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; A group may be substituted. Further, these substituents may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

Specific examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R ₃₉ to R ₄₄ in general formula (7) include a phenyloxy group, a biphenylyloxy group, a terphenyloxy lyloxy group, naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group and the like. They may be bonded to each other via a bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

The “substituent” in the “substituted or unsubstituted aryloxy group” represented by R ₃₉ to R ₄₄ in general formula (7) is represented by R ₁ to R ₃ in general formula (1). The same ones as those shown for the "substituent" in the "substituted or unsubstituted aryloxy group" can be mentioned, and the same examples can be mentioned as possible embodiments.

In general formula (7), r ₁ to r ₆ may be the same or different, r ₁ to r ₄ represent integers of 0 to 5, and r ₅ and r ₆ represent integers of 0 to 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, multiple R ₃₉ to R ₄₄ bonded to the same benzene ring may be the same They may be different and may be bonded to each other via a single bond, substituted or unsubstituted methylene group, oxygen atom or sulfur atom to form a ring.

The "divalent linking group" represented by K ₁ in the general formula (7) includes a methylene group, an ethylene group, an n-propylylene group, an isopropylylene group, an n-butylylene group, an isobutylylene group, and a tert-butylylene group. , n-pentylylene group, isopentylene group, neopentylylene group, n-hexylylene group and other "linear or branched alkylene groups having 1 to 6 carbon atoms"; cyclopentylylene group, cyclohexylylene group, adamantylene group "Cycloalkylene group having 5 to 10 carbon atoms" such as; "linear or branched alkenylene group having 2 to 6 carbon atoms" such as vinylene group, arylene group, isopropenylene group, butenylene group; benzene , biphenyl, terphenyl, tetrakisphenyl, and other aromatic hydrocarbons by removing two hydrogen atoms; naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene, indane, pyrene, triphenylene A bivalent group such as a "condensed polycyclic aromatic divalent group" obtained by removing two hydrogen atoms from a condensed polycyclic aromatic such as
Moreover, these divalent groups may have substituents. "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 of R ₃₉ to R ₄₄ in the general formula (7), "a linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "having a substituent List the same as those shown in relation to the "substituent" in the "cycloalkyl group having 5 to 10 carbon atoms" or "linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent". can be done. As a substituent of the "aromatic hydrocarbon divalent group" or the "condensed _polycyclic aromatic divalent group", the "substituted or _{unsubstituted} Examples of the same as those shown with respect to the "substituent" in the "aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" can be mentioned. The same thing can be mentioned as possible modes.
Preferred embodiments of the “divalent linking group” represented by K ₁ in general formula (7) include divalent groups represented by the above structural formulas (HTM-A) to (HTM-F).

"A linear or branched alkyl group having ₁ to 6 carbon _atoms which may have a substituent", "having a substituent "Optionally substituted cycloalkyl group having 5 to 10 carbon atoms" or "linear or branched alkenyl group having 2 to 6 carbon atoms which may be substituted", "1 to 1 6 straight-chain or branched alkyl group", "C5-C10 cycloalkyl group" or "C2-C6 straight-chain or branched alkenyl group" is represented by the general formula In (7), represented by R ₃₉ to R ₄₄ , “optionally substituted C 1 to 6 linear or branched alkyl group”, “having a substituent ``Cycloalkyl group having 5 to 10 carbon atoms which may be substituted'' or ``Linear or branched alkenyl group having 2 to 6 carbon atoms which may be substituted'' the same as those indicated for "straight-chain or branched alkyl group", "cycloalkyl group having 5 to 10 carbon atoms" or "straight-chain or branched alkenyl group having 2 to 6 carbon atoms" can be given, and possible modes can be given in the same way.

"A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent", "Alkyl group having 5 to 10 carbon atoms having a substituent" represented by R ₄₅ to R ₅₆ in the general formula (8) The “substituent” in the “cycloalkyl group of” or “a linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” includes R ₃₉ to R ₄₄ in the general formula (7) "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 carbon atom having a substituent The same ones as those shown with respect to the "substituent" in the linear or branched alkenyl group having numbers 2 to 6 can be mentioned, and the same possible embodiments can be mentioned.

“A linear or branched alkyloxy group having 1 to 6 carbon atoms optionally having a substituent” or “having a substituent” represented by R ₄₅ to R ₅₆ in the general formula (8) "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 having 5 to 10 carbon atoms which may be ” is an “optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms” represented by R ₃₉ to R ₄₄ in the general formula (7), or "Linear or branched alkyloxy group having 1 to 6 carbon atoms" or "C5 to 10 cycloalkyloxy group optionally having substituent(s)" The same ones as those shown in relation to "the cycloalkyloxy group of" can be mentioned, and the same possible embodiments can be mentioned.

"a linear or branched _alkyloxy group having ₁ to 6 carbon atoms having a substituent" or "a linear or branched alkyloxy group having 5 to 6 carbon atoms having a The “substituent” in the cycloalkyloxy group of 10” includes the “substituted linear or branched C 1 to 6 substituent represented by R ₃₉ to R ₄₄ in the general formula (7). or "substituted cycloalkyloxy group having 5 to 10 carbon atoms". can give

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic group” represented by R ₄₅ to R ₅₆ in general formula (8) The "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "aromatic ring group" are represented by R ₃₉ to R ₄₄ in the general formula (7). "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" The same groups as those shown for "heterocyclic group" or "condensed polycyclic aromatic group" can be mentioned, and these groups have a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. may be bonded to each other via to form a ring.
In addition, these groups may have a substituent, and examples of the substituent include the “substituted aromatic hydrocarbon group” and the “substituted aromatic heterohydrocarbon group” represented by R ₃₉ to R ₄₄ in the general formula (7). The same examples as those shown for the "substituent" in the "cyclic group" or the "substituted condensed polycyclic aromatic group" can be given, and the same examples can be given as possible embodiments.

The “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R ₄₅ to R ₅₆ in general formula (8) is represented by R ₃₉ to R ₄₄ in general formula (7). The same examples as those shown for the “aryloxy group” in the “substituted or unsubstituted aryloxy group” can be mentioned, and the same examples can be given as possible embodiments.

The “substituent” in the “substituted aryloxy group” represented by R ₄₅ to R ₅₆ in general formula (8) is represented by R ₃₉ to R ₄₄ in general formula (7). The same examples as those shown for the "substituent" in the "aryloxy group having a substituent" can be given, and the same examples can be given as possible modes.

In general formula (8), r ₇ to r ₁₈ may be the same or different, r ₇ to r ₁₂ represent integers of 0 to 5, and r ₁₃ to r ₁₈ represent integers of 0 to 4. When r ₇ to r ₁₂ are integers of 2 to 5, or when r ₁₃ to r ₁₈ are integers of 2 to 4, multiple R ₄₅ to R ₅₆ bonded to the same benzene ring may be the same They may be different and may be bonded to each other via a single bond, substituted or unsubstituted methylene group, oxygen atom or sulfur atom to form a ring.

As the "divalent linking group" represented by K ₂ , K ₃ and K ₄ in the general formula (8), the "divalent linking group" represented by K ₁ in the general formula (7) The same ones as those shown in relation to can be mentioned, and the same possible modes can be mentioned.

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

The arylamine compound represented by general formula (1) of this embodiment can be used as a host material for the second hole-transporting layer and/or the light-emitting layer adjacent to the light-emitting layer of the organic EL device. Excitons generated in the light-emitting layer can be confined by using materials that have higher hole injection properties, higher mobility, higher electron blocking properties, and higher stability against electrons than conventional materials. can. As a result, the probability of recombination of holes and electrons can be further improved, and high luminous efficiency can be obtained. At the same time, the driving voltage is lowered, and the effect of improving the durability of the organic EL element is obtained.

The arylamine compound represented by the general formula (1) of this embodiment can also be used as a constituent material of the light-emitting layer of an organic EL device. The compound has excellent hole-transport properties compared to conventional materials, and has the effect of being able to more preferably improve the luminous efficiency of the organic EL device, particularly when it contains a green phosphorescent light-emitting material.

The organic EL device of the present embodiment has higher hole mobility than conventional hole transport materials, excellent electron blocking ability, excellent amorphous property, and electrical reduction durability. Excellent arylamine compounds are used. Therefore, it becomes possible to realize high efficiency and high durability.

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

The arylamine compound described above can be synthesized according to a method known per se (see, for example, Patent Document 8). For example, as shown in the examples below, a disubstituted amine and a halogenated substituted aromatic hydrocarbon are reacted by a coupling reaction, and the obtained compound is further halogenated to obtain a boronic acid of the aromatic hydrocarbon. The above-mentioned arylamine compound can be synthesized by reacting with a coupling reaction.

Among the compounds represented by the chemical 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 limited to these compounds. not a thing

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

Among the compounds represented by the chemical 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 limited to these compounds. not a thing

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

Among the compounds represented by the chemical 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. do not have.

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

Specific examples of preferred compounds 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, are shown below. It is not limited to compounds.

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

Among the compounds having a benzazole 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. is not limited to compounds of

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

Specific examples of preferred compounds among the triphenylamine derivatives represented by the general formula (7), which are preferably used in the organic EL device of the present embodiment, are shown below. It is not limited.

Specific examples of preferred compounds among the triphenylamine derivatives represented by the general formula (8), which are preferably used in the organic EL device of the present embodiment, are shown below. It is not limited.

The compound having the triarylamine structure described above 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 performed by column chromatography, adsorption purification by silica gel, activated carbon, activated clay, etc., recrystallization or crystallization with a solvent, It can be performed by a sublimation purification method or the like. Identification of compounds can be done by NMR analysis. As physical properties, the melting point, glass transition point (Tg), and work function are measured. The melting point is an index of vapor deposition properties, the glass transition point (Tg) is an index of thin film state stability, and the work function is an index of hole-transporting properties and hole-blocking properties.
In addition, the compounds used in the organic EL element of the present embodiment are purified by column chromatography, adsorption purification by silica gel, activated carbon, activated clay, etc., recrystallization with a solvent, crystallization method, etc. After purification, the final To use the one purified by the sublimation purification method.

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

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

T1 of these compounds can be calculated from the measured phosphorescence spectrum. A phosphorescence spectrum can be measured using a commercially available spectrophotometer. As a general method for measuring the phosphorescence spectrum, a method of dissolving in a solvent and irradiating excitation light at low temperature to measure (for example, see Non-Patent Document 3), or vapor deposition on a silicon substrate to form a thin film, at low temperature There is a method of irradiating excitation light and measuring a phosphorescence spectrum (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 phosphorescence spectrum or the wavelength at the rising position on the short wavelength side and converting it into a light energy value according to the following formula. T1 is an index of the triplet exciton confinement ability of the phosphorescent emitter.

where E is the value of light energy, h is Planck's constant (6.63×10 ⁻³⁴ Js), c is the speed of light (3.00×10 ⁸ m/s), and λ is the short wavelength of the phosphorescence spectrum. represents the wavelength (nm) at which the side rises. 1 eV is 1.60×10 ⁻¹⁹ J.

The structure of the organic EL device of the present embodiment includes, on a substrate, 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 Examples include those having a laminated cathode, and those having a hole-blocking layer between the light-emitting layer and the electron-transporting layer in addition to the above structure. In these multilayer structures, it is possible to omit or combine some organic layers. Further, it is possible to have a structure in which two or more organic layers having the same function are laminated, such as a structure in which two light-emitting layers are laminated, a structure in which two electron transport layers are laminated, and the like.

As the anode of the organic EL element 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), porphyrin compounds typified by copper phthalocyanine and starburst type triphenyl An acceptor heterocyclic compound such as an amine derivative, hexacyanoazatriphenylene, or a coating type polymer material can be used. Thin films of these materials can be formed by known methods such as a spin coating method and an ink jet method in addition to the vapor deposition method.

As the first hole-transporting layer of the organic EL device of the present embodiment, the arylamine compounds represented by the general formulas (7) and (8) are more preferable. N'-di(m-tolyl)-benzidine (hereinafter abbreviated as TPD), N,N'-diphenyl-N,N'-di(α-naphthyl)-benzidine (hereinafter abbreviated as NPD), N ,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 deposited alone, or may be used as a single layer formed by mixing with other materials. A laminated structure of layers formed by mixing the above materials or a layer formed by mixing a plurality of materials alone and a layer formed by mixing the above materials may be used. In addition, as a hole injection/transport layer, poly(3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT)/poly(styrene sulfonate) (hereinafter abbreviated as PSS), etc. of polymeric materials can be used. Thin films of these materials can be formed by known methods such as a spin coating method and an ink jet method in addition to the vapor deposition method.

In addition, in the hole injection layer or the hole transport layer, trisbromophenylamine hexachloroantimony, radialene derivatives (for example, the compound (Acceptor-1) described later, or patent literature 17), or a polymer compound having a structure of a benzidine derivative such as TPD in its partial structure.

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 ), carbazole derivatives such as 2,2-bis(4-carbazol-9-ylphenyl)adamantane (hereinafter abbreviated as Ad-Cz), 9-[4-(carbazol-9-yl)phenyl]-9 A compound having an electron blocking action such as a compound having a triphenylsilyl group and a triarylamine structure typified by -[4-(triphenylsilyl)phenyl]-9H-fluorene can be used. These may be formed alone, or may be used as a single layer formed by mixing with other materials, layers formed by themselves, layers formed by mixing, or A laminated structure of a layer formed independently and a layer formed by mixing may be employed. Thin films of these materials can be formed by known methods such as a spin coating method and an ink jet method in addition to the vapor deposition method.

A hole-transporting host material or an electron-transporting host material can be used as the host of the light-emitting layer of the organic EL device of this embodiment. As the 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), TCTA, mCP and other carbazole derivatives can be used. Examples of electron-transporting host materials include compounds having a nitrogen-containing heteroaromatic ring structure represented by the general formula (HOST-A), p-bis(triphenylsilyl)benzene (UGH2), 2, 2′,2″-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBi) and the like can be used. These may be formed alone, or may be used as a single layer formed by mixing a plurality of materials, layers formed by themselves, layers formed by mixing, or A laminated structure of a layer formed independently and a layer formed by mixing may be employed. Thin films of these materials can be formed by known methods such as a spin coating method and an ink jet method in addition to the vapor deposition method.

In this embodiment, it is preferable to use two or more kinds of compounds, a first host compound having an electron-transporting ability and a second host compound having a hole-transporting ability. One or more of the second host compounds may be used. The first host compound and the second host compound may be contained in a weight ratio of, for example, 1:10 to 10:1.

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 is preferably a compound having a carbazole ring structure represented by the general formula (HOST-B) or an arylamine compound represented by the general formula (1) of the present embodiment.

At least one host compound may be further included in addition to the first host compound and the second host compound described above.

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. , Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof can be used. The dopant may be a red, green or blue dopant and can produce high performance organic EL devices.

In order to avoid concentration quenching, doping of the host material with the phosphorescent light-emitting material is preferably carried out by co-evaporation in the range of 1 to 30% by weight with respect to the entire light-emitting layer.

Thin films of these materials can be formed by known methods such as a spin coating method and an ink jet method in addition to the vapor deposition method.

Benzoazole compounds and pyrimidine compounds represented by the general formulas (4) and (6) are more preferable as the hole-blocking layer of the organic EL device of the present embodiment. ), metal complexes of quinolinol derivatives such as BAlq, various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and other compounds having a hole-blocking effect can be used. It may also serve as a material. These may be deposited alone, or may be used as a single layer formed by mixing with other materials. A laminated structure of layers formed by mixing the above materials or a layer formed by mixing a plurality of materials alone and a layer formed by mixing the above materials may be used. Thin films of these materials can be formed by known methods such as a spin coating method and an ink jet method in addition to the vapor deposition method.

_Benzoazole compounds and pyrimidine compounds represented by the general formulas (4) and (6) are more preferable as the electron transport layer of the organic EL device of the present embodiment. ETM-1) and other metal complexes of quinolinol derivatives, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, Pyridoindole derivatives, phenanthroline derivatives, silole derivatives and the like can also be used. These may be deposited alone, or may be used as a single layer formed by mixing with other materials. A laminated structure of layers formed by mixing the above materials or a layer formed by mixing a plurality of materials alone and a layer formed by mixing the above materials may be used. Thin films of these materials can be formed by known methods such as a spin coating method and an ink jet method in addition to the vapor deposition 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 aluminum oxide. can be used, but it can be omitted in the preferred selection of the electron-transporting layer and the cathode.

Furthermore, in the electron injection layer or the electron transport layer, an organic compound that is usually used in the layer may be N-doped with a metal such as cesium, lithium fluoride, or ytterbium.

As the cathode of the organic EL element of the present embodiment, an electrode material with a low work function such as aluminum or ytterbium, or an alloy with a lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy is used as the electrode material. Used.

BEST MODE FOR CARRYING OUT THE INVENTION 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 as long as the gist thereof is not exceeded.

<Synthesis of di(biphenyl-4-yl)-(2′-phenyl-1,1′:3′,1″-terphenyl-5′-yl)-amine (compound 1-1)>
Di(biphenyl-4-yl)-amine: 50.0 g, 5′-bromo-1,1′:3′,1″terphenyl: 57.7 g, sodium t-butoxy: 59.8 g and toluene: 1000 mL were added, and nitrogen gas was passed through while applying ultrasonic waves for 30 minutes. 1.4 g of palladium acetate and 2.5 mL of a 50% (w/v) toluene solution of t-butylphosphine were added, and the mixture was stirred under reflux with heating for 4 hours. After allowing 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 mixed solvent of toluene/acetone was added to the crude product, and the precipitated solid was collected and treated with di(biphenyl-4-yl)-(1,1′:3′,1″-terphenyl-5′-yl)-amine. of white powder: 73.9 g (yield 86%).

Di(biphenyl-4-yl)-(1,1′:3′,1″-terphenyl-5′-yl)-amine: 62.3 g and dichloromethane: 1250 mL were added to a reaction vessel purged with nitrogen, and ice was added. Cooled in a bath. N-bromosuccinimide: 20.2 g was added and stirred for 8 hours. After concentrating the reaction solution under reduced pressure, methanol was added and the precipitated solid was collected, and (2′-bromo-1,1′:3′,1″-terphenyl-5′-yl)-di( A white solid of biphenyl-4-yl)-amine: 60.0 g (84% yield) was obtained.

(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 potassium carbonate: 6.6 g dissolved in H ₂ O: 30 mL was added, and nitrogen gas was passed through while applying ultrasonic waves for 30 minutes. did. Tetrakistriphenylphosphine palladium: 0.4 g was added and stirred for 24 hours while heating under reflux. After allowing 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 crude product, the precipitated solid was collected, and di(biphenyl-4-yl)-(2′-phenyl-1,1′:3′,1″-terphenyl-5′-yl)- A white powder of amine (compound 1-1): 4.0 g (yield 40%) was obtained.

The structure of the resulting white powder was identified using NMR.
¹ H-NMR (CDCl ₃ ) detected the following 35 hydrogen signals.
δ (ppm) = 7.60 (7H), 7.46 (4H), 7.41-7.30 (6H), 7.28 (2H), 7.18-6.86 (13H), 6. 89 (3H).

<(biphenyl-4-yl)-(9,9-dimethyl-9H-fluoren-2-yl)-(2′-phenyl-1,1′:3′,1″-terphenyl-5′-yl )-Synthesis of amine (compound 1-2)>
(Biphenyl-4-yl)-(2′-bromo-1,1′:3′,1″-terphenyl-5′-yl)-(9,9 synthesized in the same manner as in Example 1 -dimethyl-9H-fluoren-2-yl)-amine: 17.6 g, toluene: 170 mL, ethanol: 35 mL, phenylboronic acid: 3.7 g, followed by potassium carbonate: 4.4 g beforehand in H ₂ O: An aqueous solution dissolved in 30 mL was added, and nitrogen gas was passed through while applying ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.6 g was added, and the mixture was stirred under reflux with heating for 24 hours. After standing to cool, the organic layer was collected by a liquid separation operation. It was washed 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)-(2 '-Phenyl-1,1': 3',1''-terphenyl-5'-yl)-amine (compound 1-2) was obtained as white powder: 11.2 g (yield 64%).

The structure of the resulting white powder was identified using NMR.
¹ H-NMR (CDCl ₃ ) detected the following 39 hydrogen signals.
δ (ppm) = 7.53-7.69 (5H), 7.21-7.48 (14H), 6.96-7.12 (12H), 6.81-6.90 (2H), 1 .51 (6H).

<Di(9,9-dimethyl-9H-fluoren-2-yl)-(2′-phenyl-1,1′:3′,1″-terphenyl-5′-yl)-amine (compound 1- Synthesis of 3)>
Synthesized in the same manner as in Example 1, (2′-bromo-1,1′:3′,1″-terphenyl-5′-yl)-di(9,9-dimethyl-9H-fluorene- 2-yl)-amine: 10.0 g, toluene: 80 mL, ethanol: 40 mL, phenylboronic acid: 2.1 g, and then potassium carbonate: 5.9 g dissolved in H ₂ O: 30 mL in advance was added. Nitrogen gas was passed through while applying ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.3 g was added, and the mixture was stirred under reflux with heating for 5 hours. After allowing 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 mixed solvent of THF/acetone was added to the crude product, and the precipitated solid was collected. A white powder of ''-terphenyl-5'-yl)-amine (compound 1-3): 7.7 g (yield 77%) was obtained.

The structure of the resulting white powder was identified using NMR.
¹ H-NMR (DMSO-d ₆ ) detected the following 43 hydrogen signals.
δ (ppm) = 7.81 (2H), 7.76 (2H), 7.53 (4H), 7.31 (4H), 7.18 (2H), 7.08 (6H), 7.03 -6.92 (9H), 6.83 (2H), 1.44 (12H).

<(biphenyl-4-yl)-(9,9-diphenyl-9H-fluoren-2-yl)-(2′-phenyl-1,1′:3′,1″-terphenyl-5′-yl )-Synthesis of amine (compound 1-4)>
(Biphenyl-4-yl)-(2′-bromo-1,1′:3′,1″-terphenyl-5′-yl)-(9,9 synthesized in the same manner as in Example 1 -diphenyl-9H-fluoren-2-yl)-amine: 14.0 g, toluene: 140 mL, ethanol: 35 mL, phenylboronic acid: 3.2 g, followed by potassium carbonate: 4.9 g beforehand in H ₂ O: An aqueous solution dissolved in 35 mL was added, and nitrogen gas was passed through while applying ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.4 g was added and stirred for 20 hours while heating under reflux. After allowing 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 mixed solvent of toluene/acetone was added to the crude product, and the precipitated solid was collected and treated with (biphenyl-4-yl)-(9,9-diphenyl-9H-fluoren-2-yl)-(2′-phenyl-1, A white powder of 1′:3′,1″-terphenyl-5′-yl)-amine (compound 1-4): 7.5 g (yield 54%) was obtained.

The structure of the resulting white powder was identified using NMR.
¹ H-NMR (DMSO-d ₆ ) detected the following 43 hydrogen signals.
δ (ppm) = 7.91 (1H), 7.87 (1H), 7.65 (4H), 7.49-7.04 (26H), 6.99 (3H), 6.94 (2H) , 6.90 (4H), 6.79 (2H).

<(biphenyl-4-yl)-{4-(naphthyl-2-yl)-phenyl)}-(2′-phenyl-1,1′:3′,1″-terphenyl-5′-yl) -Synthesis of amine (compound 1-58)>
(Biphenyl-4-yl)-(2′-bromo-1,1′:3′,1″-terphenyl-5′-yl)-{4-( Naphthyl-2-yl)-phenyl)}-amine: 10.0 g, toluene: 70 mL, ethanol: 30 mL, phenylboronic acid: 2.7 g, followed by potassium carbonate: 6.1 g H ₂ O: 20 mL was added, and nitrogen gas was passed through while applying ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.3 g was added and stirred for 24 hours while heating under reflux. After standing to cool, methanol was added and the precipitated solid was collected to obtain a crude product. A mixed solvent of THF/acetone was added to the crude product, and the precipitated solid was collected, and (biphenyl-4-yl)-(2′-bromo-1,1′:3′,1″-terphenyl-5′- A white powder of yl)-{4-(naphthyl-2-yl)-phenyl)}-amine (compound 1-58): 6.5 g (yield 65%) was obtained.

The structure of the resulting white powder was identified using NMR.
¹ H-NMR (DMSO-d ₆ ) detected the following 37 hydrogen signals.
δ (ppm) = 8.21 (1H), 7.96 (3H), 7.86 (3H), 7.70 (4H) 7.52 (2H), 7.45 (2H), 7.35 ( 5H), 7.19-6.96 (15H), 6.86 (2H).

<Di{4-(naphthyl-2-yl)-phenyl)}-(2′-phenyl-1,1′:3′,1″-terphenyl-5′-yl)-amine (compound 1-62 ) synthesis>
(2′-Bromo-1,1′:3′,1″-terphenyl-5′-yl)-di{4-(naphthyl-2-yl)-, synthesized in the same manner as in Example 1 Phenyl)}-amine: 15.0 g, toluene: 160 mL, ethanol: 40 mL, phenylboronic acid: 3.0 g, and then an aqueous solution prepared by previously dissolving potassium carbonate: 5.7 g in H ₂ O: 40 mL was added. Nitrogen gas was passed through while applying ultrasonic waves for 30 minutes. Tetrakistriphenylphosphine palladium: 0.5 g was added, and the mixture was stirred under reflux with heating for 21 hours. After standing to cool, the organic layer was collected by a liquid separation operation. It was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. A mixed solvent of toluene/n-heptane was added to the crude product, and the precipitated solid was collected, and di{4-(naphthyl-2-yl)-phenyl)}-(2′-phenyl-1,1′:3′, A white powder of 1″-terphenyl-5′-yl)-amine (compound 1-62): 8.2 g (yield 55%) was obtained.

The structure of the resulting white powder was identified using NMR.
¹ H-NMR (DMSO-d ₆ ) detected the following 39 hydrogen signals.
δ (ppm) = 8.22 (2H), 8.03-7.90 (6H), 7.86 (6H), 7.53 (4H) 7.39 (4H), 7.19-6.98 (15H), 6.87 (2H).

The glass transition point of the arylamine compound represented by the general formula (1) was determined using a high-sensitivity differential scanning calorimeter (DSC3100S, manufactured by Bruker AXS).
glass transition point
Compound of Example 1 110°C
Compound of Example 2 121°C
Compound of Example 3 135°C
Compound of Example 4 140°C
Compound of Example 5 115°C
Compound of Example 6 121°C

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

Using the compounds of Examples 1 to 6, a deposited film with a thickness of 100 nm was prepared on an ITO substrate, and the work function was measured with an ionization potential measurement device (manufactured by Sumitomo Heavy Industries, Ltd., PYS-202 type). was measured.
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, the compounds of Examples 1 to 6 show a suitable energy level compared to the work function of 5.4 eV that general hole transport materials such as NPD and TPD have, and are good positive electrons. It can be seen that it has pore transport ability.

For the compounds of Examples 1 to 4, 2-methyltetrahydrofuran solutions of 1.0×10 ⁻⁵ mol/L were prepared. The prepared solution was placed in a dedicated quartz tube, oxygen was removed by aeration with pure nitrogen, and the tube was plugged with a septum rubber to prevent contamination by oxygen. After cooling to 77K, the phosphorescence spectrum was measured by irradiating excitation light using a fluorescence phosphorescence spectrophotometer (manufactured by JASCO Corporation, Model FP-8500). 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. For reference, HTM-2 and T1 of compound (3-3) are also shown below.
T1
Compound (1-1) of Example 1 2.55 eV
Compound (1-2) of Example 2 2.58 eV
Compound (1-3) of Example 3 2.58 eV
Compound (1-4) of Example 4 2.57 eV
HTM-2 2.40 eV
Compound 3-3 2.43 eV

Thus, the compounds used in the present disclosure have T1 values greater than that of tri(m-terphenyl-4-yl)amine (HTM-2), a commonly used hole-transporting material. The two meta-substituted phenyl groups to the nitrogen atom of triarylamine cause a large twist in the skeleton around the amine, and the para-substituted phenyl group to the nitrogen atom acts as a large steric hindrance group. By acting, the compounds used in this disclosure achieve higher T1 compared to HTM-2. In addition, the compound used in the present disclosure has a T1 value greater than that of tris(4-methyl-2,5-diphenylpyridine)iridium (III) (compound 3-3), which is a green phosphorescent material, It has the ability to sufficiently confine triplet excitons excited in the light-emitting layer.

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

Specifically, the glass substrate 1 on which an ITO film having a thickness of 150 nm was formed was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 200° C. for 10 minutes. Then, after performing UV ozone treatment for 15 minutes, this ITO-attached glass substrate was mounted in a vacuum deposition machine, 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, a compound Acceptor-1 and a compound (7-3) of the following structural formula were deposited at a deposition rate ratio of Acceptor-1:Compound (7-3)= Two-source vapor deposition was performed on the transparent anode 2 at a vapor deposition rate of 3:97 to form a hole injection layer 3 having a thickness of 10 nm. On the hole injection layer 3, the compound (7-3) was vapor-deposited as the first hole transport layer 4 to a thickness of 70 nm. On the first hole transport layer 4, the compound (1-2) of Example 2 was vapor-deposited as the second hole transport layer 5 to a thickness of 10 nm. On the second hole-transporting layer 5, the first host compound (A-19) and the second host compound (B-22) are simultaneously used as a light-emitting layer 6, and the iridium compound (B-22) is used as a dopant. 3-3) was doped to 5 wt %, and the compound was vacuum-deposited to a film thickness of 40 nm. Here, the first host compound (A-19) and the second host compound (B-22) were used at a ratio of 1:1.

Next, a compound (4-78) of the following structural formula and a compound ETM-1 of the following structural formula are deposited on the light-emitting layer 6 as an electron-transporting layer 7 so that the deposition rate ratio is compound (4-78):ETM. Two-source vapor deposition was performed at a vapor deposition rate of −1=50:50 to form an electron transport layer 6 having a thickness of 30 nm. Lithium fluoride was vapor-deposited as an electron injection layer 8 on the electron transport layer 7 so as to have a thickness of 1 nm. Finally, a cathode 9 was formed by depositing aluminum on the electron injection layer 8 to a thickness of 100 nm. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

An organic EL device was fabricated in the same manner as in Example 10, except that the compound (6-1) was used as the material of the electron transport layer 7 instead of the compound (4-78). The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

An organic EL device was fabricated in the same manner as in Example 10, except that the compound (1-3) of Example 3 was used instead of the compound (1-2) of Example 2 as the material for the second hole transport layer 5. made. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

An organic EL device was fabricated in the same manner as in Example 12, except that the compound (6-1) was used as the material of the electron transport layer 7 instead of the compound (4-78). The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

An organic EL device was fabricated in the same manner as in Example 10, except that the compound (1-4) of Example 4 was used instead of the compound (1-2) of Example 2 as the material for the second hole transport layer 5. made. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

An organic EL device was fabricated in the same manner as in Example 14, except that the compound (6-1) was used as the material of the electron transport layer 7 instead of the compound (4-78). The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

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

An organic EL device was fabricated in the same manner as in Example 11 except that the compound (1-2) of Example 2 was used as the second host material instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-2) were used at a ratio of 1:1. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

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

An organic EL device was fabricated in the same manner as in Example 13, except that the compound (1-3) of Example 3 was used as the second host material instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-3) were used at a ratio of 1:1. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

An organic EL device was fabricated in the same manner as in Example 14, except that the compound (1-4) of Example 4 was used as the second host material instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-4) were used at a ratio of 1:1. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

An organic EL device was fabricated in the same manner as in Example 15, except that the compound (1-4) of Example 4 was used as the second host material instead of the compound (B-22). Here, the first host compound (A-19) and the second host compound (1-4) were used at a ratio of 1:1. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

[Comparative Example 1]
For comparison, an organic EL device was prepared 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 for the second hole transport layer 5. was made. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

[Comparative Example 2]
For comparison, an organic EL device was prepared 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 for the second hole transport layer 5. was made. The characteristics of the produced organic EL device were measured at room temperature in the air. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

[Comparative Example 3]
For comparison, Example 10 was carried out in the same manner as the material of the second hole transport layer 5 except that the compound (B-22) of the following structural formula was used instead of the compound (1-2) of Example 2. An organic EL device was produced by The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

[Comparative Example 4]
For comparison, an organic EL device was prepared 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 for the second hole transport layer 5. was made. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

[Comparative Example 5]
For comparison, in Example 14, 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, and the compound (HTM-2) of Example 2 was used as the second host material. An organic EL device was prepared in the same manner except that the compound (HTM-2) was used instead of the compound (1-2). Here, the first host compound (A-19) and the second host compound (HTM-2) were used at a ratio of 1:1. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

[Comparative Example 6]
For comparison, in Example 15, 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, and the compound (HTM-2) of Example 2 was used as the second host material. An organic EL device was produced in the same manner except that the compound (HTM-2) was used in place of the compound (1-2). Here, the first host compound (A-19) and the second host compound (HTM-2) were used at a ratio of 1:1. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere. Table 1 summarizes the measurement results of the emission characteristics when a DC voltage is applied to the fabricated organic EL device.

Using the organic EL devices produced in Examples 10 to 21 and Comparative Examples 1 to 6, the device life was measured and the results are summarized in Table 1. The life of the element is determined by setting the emission luminance (initial luminance) at the start of light emission to 10000 cd/m ² and constant current driving, and the emission luminance is 9500 cd/m ² (equivalent to 95% when the initial luminance is 100%: Measured as the time to decay to 95% decay).

As shown in Table 1, Examples 10 to 15 using the arylamine compound of the present disclosure as the second hole transport material, respectively, and the compound (HTM-2) and the compound (B-22) were used as the second positive hole transport material. In comparison with Comparative Examples 1 to 4, which were used as hole-transporting materials, the luminous efficiencies of the organic EL devices of Comparative Examples 1 to 4 were 72.06 to 73.0 when a current with a current density of 10 mA/cm ² was applied. Compared to 03 cd/A, the organic EL devices of Examples 10 to 15 had a high efficiency of 76.05 to 78.00 cd/A. In addition, the power efficiency is as high as 57.31 to 58.99 lm/W for the organic EL devices of Examples 10 to 15, compared to 52.00 to 53.27 lm/W for the organic EL devices of Comparative Examples 1 to 4. It was efficient. On the other hand, the device life (95% attenuation) was 341 to 400 hours for the organic EL devices of Comparative Examples 1 to 4, while the organic EL devices of Examples 10 to 15 were 461 to 585 hours. It can be seen that the life span is greatly extended.

As shown in Table 1, Examples 16 to 21 using the arylamine compound of the present disclosure as the second hole transport material and the second host material, and the compound (HTM-2) as the second hole transport material and In comparison with Comparative Examples 5 and 6 using the second host material and Comparative Examples 3 and 4 using the compound (B-22) as the second hole transport material and the second host material, the current density was 10 mA/ The luminous efficiency of the organic EL devices of Comparative Examples 3-6 was 63.74-73.03 cd/A when a current of cm ² was applied, while the organic EL devices of Examples 16-21 had luminous efficiencies of 73.98-76. 04 cd/A, which is a high efficiency. In addition, the power efficiency is as high as 55.53 to 56.32 lm/W for the organic EL devices of Examples 16 to 21, compared to 45.93 to 53.27 lm/W for the organic EL devices of Comparative Examples 3 to 6. It was efficient. On the other hand, the device life (95% attenuation) was 309 to 384 hours for the organic EL devices of Comparative Examples 3 to 6, whereas it was 408 to 480 hours for the organic EL devices of Examples 16 to 21. It can be seen that the life span is greatly extended.

As is clear from the results in Table 1, an organic EL device comprising a light-emitting layer using both a first host material having a high electron-transporting ability and a second host material having a hole-transporting ability, wherein the aryl of the present disclosure An organic EL device using an amine compound as a material for the second hole transport layer has improved power efficiency, It was found that longer life can be achieved. This is due to the fact that the arylamine compounds of the present disclosure have higher T1 values than HTM-2. The organic EL device using the arylamine compound of the present disclosure can sufficiently confine the triplet excitons excited in the light-emitting layer as compared with the organic EL device using HTM-2. As a result, an organic EL device having improved efficiency characteristics and significantly improved life characteristics has been realized. Further, it was found that improvement in power efficiency and extension of life can be achieved even in comparison with an organic EL device using the compound (B-22), which is a carbazole derivative, as a material for the second hole transport layer. By combining arylamine compounds having specific structures, holes were efficiently supplied to the light-emitting layer, and electron excess in the light-emitting layer was improved. As a result, the carrier balance in the light-emitting layer is further refined, and an organic EL device with improved efficiency characteristics and significantly improved life characteristics is realized.

Furthermore, in the organic EL device using the arylamine compound of the present disclosure as the second host material, compared with the organic EL device using the compound (HTM-2), which is also an arylamine compound, the power efficiency is improved. , it was found that longer life can be achieved. The arylamine compound of the present disclosure has a T1 value greater than that of the compound (compound 3-3), which is a green phosphorescent light-emitting material, and even when used as a second host material, excited triplet excitons are generated. I am able to close it down enough. On the other hand, HTM-2 has a low T1 and insufficient confinement of triplet excitons, and deactivation of the excited triplet excitons greatly reduces the luminous efficiency and device life. 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 with excellent electrical durability and excellent hole-transporting ability, holes are efficiently supplied to the light-emitting layer, and electron excess in the light-emitting layer is improved. As a result, the carrier balance in the light-emitting layer is further refined, and an organic EL device with improved efficiency characteristics and significantly improved life characteristics is realized.

This application is based on a Japanese patent application (Japanese Patent Application No. 2017-233148) filed on December 5, 2017, the entirety of which is incorporated by reference. Also, all references cited herein are incorporated in their entirety.
Although the present invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

The organic EL device of the present invention has improved luminous efficiency and greatly improved durability, and has become possible to be applied to home electric appliances and lighting applications, for example.

REFERENCE SIGNS LIST 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 (8)

Between the anode and the cathode, at least a first hole-transporting layer, a second hole-transporting layer, a green light-emitting layer, and an electron-transporting layer are provided in this order from the anode side, and the first hole-transporting layer and the electron-transporting layer At least one of the layers arranged between the layers contains an arylamine compound represented by the following general formula (1) ,
The green emitting layer includes a host and a phosphorescent dopant, and the host includes at least one first host compound represented by the following chemical formula Host-A and the following chemical formula Host-B. and at least one second host compound .

(wherein Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or unsubstituted represents a condensed polycyclic aromatic group, R ₁ , R ₂ and R ₃ may be the same or different and have a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group and a substituent A linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted, 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 be optionally substituted, 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, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or represents a substituted or unsubstituted aryloxy group.)

(In Host-A, Z is each independently N or CRa, at least one of Z is N, 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 ring-forming carbon atoms, The total number of 6-membered rings substituted by triphenylene groups in Host-A is 6 or less, and L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted tertiary a phenylene group, 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 a substituted or 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 hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted ring It is a heteroaryl group having 4 to 50 carbon atoms, and 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.) Between the anode and the cathode, at least a first hole-transporting layer, a second hole-transporting layer, a green light-emitting layer, and an electron-transporting layer are provided in this order from the anode side, and the first hole-transporting layer and the electron-transporting layer At least one of the layers arranged between the layers contains an arylamine compound represented by the following general formula (2) ,
The green emitting layer includes a host and a phosphorescent dopant, and the host includes at least one first host compound represented by the following chemical formula Host-A and the following chemical formula Host-B. and at least one second host compound .

(In the formula, Ar ₁ and Ar ₂ may be the same or different, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted condensed polycyclic aromatic Ar ₅ and Ar ₆ , which may be the same or different, represent a phenyl group, biphenylyl group, naphthyl group, phenanthrenyl group, or fluorenyl group; R ₄ represents a hydrogen atom, a deuterium atom, a fluorine atom; , a chlorine atom, a cyano group, a nitro group, an optionally substituted C 1 to 6 linear or branched alkyl group, an optionally substituted C 5 to 10 cycloalkyl group, optionally substituted C2-C6 linear or branched alkenyl group, optionally substituted C1-C6 linear straight or branched alkyloxy group, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic ring group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group.)

(In Host-A, Z is each independently N or CRa, at least one of Z is N, 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 ring-forming carbon atoms, The total number of 6-membered rings substituted by triphenylene groups in Host-A is 6 or less, and L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted tertiary a phenylene group, 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 a substituted or 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 hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, alkyl group having 1 to 15 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted ring It is a heteroaryl group having 4 to 50 carbon atoms, and 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.) Between the anode and the cathode, at least a first hole-transporting layer, a second hole-transporting layer, a green light-emitting layer, and an electron-transporting layer are provided in this order from the anode side, and the first hole-transporting layer and the electron-transporting layer At least one of the layers arranged between the layers contains an arylamine compound represented by the following general formula (1),
The organic EL device, wherein the electron transport layer contains a compound having a benzazole structure represented by the following general formula (6).

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ each may be the same or different and represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group; ₁ , R ₂ , R ₃ may be the same or different, hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, optionally substituted linear or branched C 1 to 6 an alkyl group of, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, an optionally substituted linear or branched alkenyl group having 2 to 6 carbon atoms, optionally substituted linear or branched C 1-6 alkyloxy group, optionally substituted C 5-10 cycloalkyloxy group, substituted or It represents an 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. )

(In the formula, Ar ₁₂ , Ar ₁₃ may be the same or different, 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 aromatic heterocyclic represents a cyclic 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, optionally substituted C 1 to 6 A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, or an optionally substituted linear chain having 2 to 6 carbon atoms represents a linear or branched alkenyl group, X represents an oxygen atom or a sulfur atom, W ₁ , W ₂ may be the same or different and represent a carbon atom or a nitrogen atom. ) Between the anode and the cathode, at least a first hole-transporting layer, a second hole-transporting layer, a green light-emitting layer, and an electron-transporting layer are provided in this order from the anode side, and the first hole-transporting layer and the electron-transporting layer At least one of the layers arranged between the layers contains an arylamine compound represented by the following general formula (2),
The organic EL device, wherein the electron transport layer contains a compound having a benzazole structure represented by the following general formula (6).

(In the formula, Ar ₁ , Ar ₂ may be the same or different, and represents 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 , Ar ₆ may be the same or different, and represents a phenyl group, biphenylyl group, naphthyl group, phenanthrenyl group, or fluorenyl group; ₄ has a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, or a substituent a cycloalkyl group having 5 to 10 carbon atoms which may be substituted, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent; linear or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group , represents a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted or unsubstituted aryloxy group. )

(In the formula, Ar ₁₂ , Ar ₁₃ may be the same or different, 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 aromatic heterocyclic represents a cyclic 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, optionally substituted C 1 to 6 A linear or branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, or an optionally substituted linear chain having 2 to 6 carbon atoms represents a linear or branched alkenyl group, X represents an oxygen atom or a sulfur atom, W ₁ , W ₂ may be the same or different and represent a carbon atom or a nitrogen atom. ) 5. The organic EL device according to claim 1 , wherein said green emitting layer contains a host and a phosphorescent dopant, and said phosphorescent dopant is a metal complex containing iridium. 5. The green light-emitting layer according to any one of claims 1 to 4 , 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). organic EL element.

(Wherein, R ₁₉ to R ₃₄ may be the same or different, and may be a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, or an optionally substituted linear chain having 1 to 6 carbon atoms. or a branched alkyl group, an optionally substituted cycloalkyl group having 5 to 10 carbon atoms, or an optionally substituted linear or branched 2 to 6 carbon atom alkenyl group, optionally substituted C1-C6 linear or branched alkyloxy group, optionally substituted C5-C10 cycloalkyloxy group , 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 an aromatic represents a disubstituted amino group substituted with a group selected from the group consisting of a hydrocarbon group, an aromatic heterocyclic group and a condensed polycyclic aromatic group, n represents an integer of 1 to 3.) The organic EL device according to any one of claims 1 to 6 , wherein the electron transport layer contains a compound having a pyrimidine structure represented by the following general formula (4).

(wherein Ar ₈ represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted condensed polycyclic aromatic group; Ar ₉ and Ar ₁₀ may be the same or different; represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, and B represents a monovalent group represented by the following structural formula (5), wherein Ar ₉ and Ar ₁₀ cannot be hydrogen atoms at the same time.)

(wherein Ar ₁₁ represents a substituted or unsubstituted aromatic heterocyclic group, R ₃₅ to R ₃₈ may be the same or different, hydrogen atom, deuterium atom, fluorine atom, chlorine atom, a cyano group, a trifluoromethyl 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 represents an unsubstituted condensed polycyclic aromatic group.) 8. The organic EL device according to claim 1, wherein the first hole-transporting layer contains a triphenylamine derivative represented by general formula (7) or (8) below.

(In the formula, R ₃₉ to R ₄₄ each independently deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, optionally substituted linear chain having 1 to 6 carbon atoms linear or branched alkyl group, optionally substituted cycloalkyl group having 5 to 10 carbon atoms, linear or branched chain having 2 to 6 carbon atoms optionally having substituent(s) alkenyl group, optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy having 5 to 10 carbon atoms r ₁ represents a group, 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. to r ₆ may be the same or different, r ₁ to r ₄ represent integers of 0 to 5, r ₅ and r ₆ represent integers of 0 to 4. r ₁ to r ₆ are 2 or more; When it is an integer, the plurality of R ₃₉ to R ₄₄ bonded to the same benzene ring may be the same or different, and the benzene ring and the substituents substituted on the benzene ring are Multiple substituted substituents and benzene rings adjacent to each other via a nitrogen atom may be bonded to each other by a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. K ₁ represents a divalent group represented by the following structural formulas (HTM-A) to (HTM-F), or a single bond.)

(Wherein, j represents an integer of 1 to 3.)

(In the formula, R ₄₅ to R ₅₆ each independently deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, optionally substituted linear chain having 1 to 6 carbon atoms linear or branched alkyl group, optionally substituted cycloalkyl group having 5 to 10 carbon atoms, linear or branched chain having 2 to 6 carbon atoms optionally having substituent(s) alkenyl group, optionally substituted linear or branched alkyloxy group having 1 to 6 carbon atoms, optionally substituted cycloalkyloxy having 5 to 10 carbon atoms r ₇ represents a group, 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. to r ₁₈ may be the same or different, r ₇ to r ₁₂ each represent an integer of 0 to 5, and r ₁₃ to r ₁₈ each represent an integer of 0 to 4. r ₇ to r ₁₈ are 2 or more; When it is an integer, the plurality of R ₄₅ to R ₅₆ bonded to the same benzene ring may be the same or different, and the benzene ring and the substituents substituted on the benzene ring are Multiple substituted substituents and benzene rings adjacent to each other via a nitrogen atom may be bonded to each other by a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. K ₂ to K ₄ may be the same or different, and each represents a divalent group represented by (HTM-A) to (HTM-F) in general formula (7), or a single bond.)

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