TWI791943B - Compound, organic optoelectronic device and display device - Google Patents

Abstract

The present application relates to a compound represented by Chemical Formula 1, an organic optoelectronic diode and a display device.

[Chemical Formula 1] In Chemical Formula 1, each substituent has the same definition as in the specification.

Description

Compound, organic photodiode and display device

This application claims priority and benefits to Korean Patent Application No. 10-2019-0009761 filed at the Korean Intellectual Property Office on January 25, 2019, the entire contents of which are incorporated herein by reference.

The present application relates to a compound, an organic photodiode and a display device.

Organic photodiodes are devices capable of interconverting electrical energy and light energy.

Organic photodiodes can be classified into two categories depending on the principle of operation. One is a photodiode, in which excitons formed by light energy are separated into electrons and holes and electricity is generated when the electrons and holes are each transferred to a different electrode, and the other is a light-emitting diode, which is powered by supplying Voltage or current to the electrodes produces light energy from electrical energy.

Examples of the organic photoelectric diode may include an organic photoelectric diode, an organic light emitting diode, an organic solar cell, an organic photoconductive drum, and the like.

Among them, organic light emitting diodes (OLEDs) have attracted extensive attention in recent years as the demand for flat panel display devices increases. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by the organic materials disposed between electrodes.

An organic light emitting diode has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light emitting diode having such a structure, electrons and holes injected from two electrodes are combined and paired in an organic thin film, and light is emitted when the electrons and holes are annihilated. A single-layer or multi-layer organic thin film can be formed as necessary.

The material of the organic thin film may have a light-emitting function as required. For example, a compound capable of forming the light emitting layer itself may be used alone as a material of the organic thin film, or a compound capable of functioning as a host or a dopant of a host-dopant-based light emitting layer may also be used as a material for organic thin films.

In addition, compounds capable of functioning as hole injection, hole transfer, electron blocking, hole blocking, electron transfer, electron injection, and the like can also be used as the material of the organic thin film.

In order to improve the performance, lifetime or efficiency of OLEDs, continuous research and development of organic thin film materials is required.

[technical problem]

One embodiment of the present specification is concerned with providing a compound capable of obtaining an organic photodiode having high efficiency and long service life.

Another embodiment of the present specification relates to providing an organic photodiode comprising the compound.

Yet another embodiment of the present specification relates to providing a display device including the organic photodiode. [Technical solution]

One embodiment of the present application provides a compound represented by Chemical Formula 1 below. [chemical formula 1]

In Chemical Formula 1, Ar ¹ is a substituent with hole characteristics, R ¹ to R ²⁰ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl or substituted or unsubstituted Substituted C6 to C60 aryl, L ^{to L3} are each independently a single bond, substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl, and n1 to n3 are each independently one of the integers of 0 to 2.

Another embodiment of the present specification provides an organic photodiode comprising an anode and a cathode facing each other and at least one organic layer disposed between the anode and the cathode, wherein the organic layer comprises said compound.

Yet another embodiment of the present specification provides a display device including an organic photodiode. [favorable effect]

An organic photodiode with high efficiency and long service life can be obtained.

Hereinafter, embodiments of the present disclosure will be described in detail. However, these embodiments are for illustrative purposes only, and the present disclosure is not limited thereto and is only defined by the categories of claims described later.

In this specification, "substituted or unsubstituted" means: substituted by one or more substituents selected from the group consisting of: deuterium, halo, -CN, C1 to C60 straight chain or Branched chain alkyl, C2 to C60 straight chain or branched alkenyl, C2 to C60 straight chain or branched alkynyl, C3 to C60 monocyclic or polycyclic cycloalkyl, C2 to C60 monocyclic or polycyclic heterocycloalkane Group, C6 to C60 monocyclic or polycyclic aryl group, C2 to C60 monocyclic or polycyclic heteroaryl group, -SiRR'R", -P(=O)RR', C1 to C20 alkylamino group, C6 to C60 monocyclic or polycyclic arylamine, C2 to C60 monocyclic or polycyclic heteroarylamine, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or Unsubstituted heteroaryloxy group, substituted or unsubstituted arylthiooxy group, substituted or unsubstituted alkylthiooxy group, substituted or unsubstituted arylthiooxy group substituted or unsubstituted alkenyl, substituted or unsubstituted boronyl, substituted or unsubstituted silyl, substituted or unsubstituted arylphosphino, substituted or unsubstituted A phosphine oxide group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted aromatic or aliphatic heterocyclic group including one or more of N, O and S atoms, or unsubstituted; Or substituted by a substituent that makes two or more of the substituents bonded, or unsubstituted; or a substituent that makes two or more of the substituents selected from the above-mentioned substituents bonded Substituted or unsubstituted. In addition, these groups may further form rings with adjacent substituents.

For example, "a substituent that links two or more substituents" may include biphenyl. In other words, a biphenyl group may be an aryl group, or a substituent interpreted as a link between two phenyl groups. Additional substituents may be further substituted. R, R', and R" are the same or different from each other, and are each independently hydrogen, deuterium, -CN, substituted or unsubstituted C1 to C60 linear or branched chain alkyl, substituted or unsubstituted C3 to C60 monocyclic or polycyclic cycloalkyl, substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl, or substituted or unsubstituted C2 to C60 monocyclic or polycyclic heteroaryl.

According to one embodiment of the present application, "substituted or unsubstituted" means substituted or unsubstituted by one or more substituents selected from the group consisting of: deuterium, halo, -CN , -SiRR'R", -P(=O)RR', C1 to C20 straight chain or branched chain alkyl, C6 to C60 monocyclic or polycyclic aryl and C2 to C60 monocyclic or polycyclic heteroaryl, And R, R' and R" are the same or different from each other and are each independently: hydrogen; deuterium; -CN; unsubstituted or deuterium, halo, -CN, C1 to C20 alkyl, C6 to C60 aryl and C1 to C60 alkyl substituted with C2 to C60 heteroaryl; C3 to C60 ring unsubstituted or substituted with deuterium, halogen, -CN, C1 to C20 alkyl, C6 to C60 aryl and C2 to C60 heteroaryl Alkyl; C6 to C60 aryl unsubstituted or substituted with deuterium, halogen, -CN, C1 to C20 alkyl, C6 to C60 aryl and C2 to C60 heteroaryl; or unsubstituted or substituted with deuterium, halogen , -CN, C1 to C20 alkyl, C6 to C60 aryl and C2 to C60 heteroaryl substituted by C2 to C60 heteroaryl.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and the position of substitution is not limited as long as the substitution position is a position where a hydrogen atom is substituted, that is, a position where a substituent can be substituted , and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In this specification, halogen may include fluorine, chlorine, bromine or iodine.

In this specification, the alkyl group includes C1 to C60 straight or branched chains, and may be further substituted with other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, specifically 1 to 20, and more specifically 1 to 10. Specific examples thereof may include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, second-butyl, 1- Methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methyl Pentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclo Hexylmethyl, octyl, n-octyl, tertiary octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In this specification, alkenyl includes C2 to C60 straight or branched chains, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof may include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentene Base, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethenyl-1-yl, 2-phenylethenyl- 1-yl, 2,2-diphenylethenyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl- 1-yl) vinyl-1-yl, stilbene, styryl and the like.

In this specification, the alkynyl group includes C2 to C60 straight or branched chains, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

In this specification, cycloalkyl includes C3 to C60 monocyclic or polycyclic rings, and may be further substituted with other substituents. Herein, polycyclic means a group in which a cycloalkyl group is directly bonded to or fused to another cyclic group. Herein, another cyclic group may be a cycloalkyl group, but may also include other types of cyclic groups such as heterocycloalkyl, aryl and heteroaryl. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl , 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and similar groups .

In the present specification, alkoxy may include C1 to C10 alkoxy, and more specifically, methoxy, ethoxy, propoxy, butoxy, pentyloxy, and the like.

In this specification, the silyl group can be represented by -SiRR'R", and R, R' and R" have the same definitions as above. More specifically, -Sidimethyl (-Sidimethyl), -Sidiethyl (-Sidiethyl), -Simethylethyl (-Simethylethyl), and the like may be contained.

In the present specification, the phosphine oxide group may be represented by -P(=O)RR', and R and R' have the same definitions as above. More specifically, -P(=O)dimethyl (-P(=O)dimethyl), -P(=O)diethyl (-P(=O)diethyl), -P(=O)diethyl may be included )methylethyl (-P(=O)methylethyl) and similar groups.

In this specification, the fluorenyl group means a substituent including various substituents at the number 9 position. Specifically, a concept including a fluorenyl group in which the number 9 position is substituted with two hydrogens, two alkyl groups, two aryl groups or two heteroaryl groups can be used. More specifically, 9-di-H-fluorenyl, 9-di-methyl-fluorenyl, 9-di-phenyl-fluorenyl or similar groups may be used.

In this specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, includes C2 to C60 monocyclic or polycyclic rings, and may be further substituted with other substituents. Herein, polycyclic means a group in which a heterocycloalkyl group is directly bonded to or fused to another cyclic group. Herein, another cyclic group may be a heterocycloalkyl group, but may also include other types of cyclic groups such as cycloalkyl, aryl and heteroaryl. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In this specification, the aryl group includes C6 to C60 monocyclic or polycyclic rings, and may be further substituted with other substituents. Herein, polycyclic means a group in which an aryl group is directly bonded to or fused to another cyclic group. Herein, another cyclic group may be an aryl group, but may also include other types of cyclic groups such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl groups include spirocyclic groups. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, specifically 6 to 30 and more specifically 6 to 25. Specific examples of aryl groups may include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, chrysyl, phenanthrenyl, perylene, fluorenyl, terphenyl, acryl, Naphthyl, pyrenyl, fused tetraphenyl, condensed pentaphenyl, fluorenyl, indenyl, acenaphthyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, and its fused rings groups and similar groups.

In this specification, a spiro group is a group including a spiro structure, and may be C15 to C60. For example, a spiro group may include a structure in which a 2,3-dihydro-1H-indenyl or cyclohexyl group is spiro-bonded to a fluorenyl group. Specifically, the spirocyclic group may include any of the following groups of structural formulae.

In this specification, the heteroaryl group includes S, O, Se, N or Si as a heteroatom, includes C2 to C60 monocyclic or polycyclic rings, and may be further substituted with other substituents. Herein, polycyclic means a group in which a heteroaryl group is directly bonded to or fused to another cyclic group. Herein, another cyclic group may be a heteroaryl group, but may also include other types of cyclic groups such as cycloalkyl, heterocycloalkyl, and aryl. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, specifically 2 to 30 and more specifically 3 to 25. Specific examples of heteroaryl may include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl , isothiazolyl, triazolyl, furanyl, oxadiazolyl, thiadiazolyl, bithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazolyl Azinyl, dioxynyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl group, quinozolinyl group), naphthyridinyl, acridinyl, phenanthryl, imidazopyridinyl, naphthyridine, triazindenyl, indolyl, indorazinyl, benzothiazolyl, benzoxazolyl , Benzimidazolyl, Benzothienyl, Benzofuryl, Dibenzothienyl, Dibenzofuryl, Carbazolyl, Benzocarbazolyl, Dibenzocarbazolyl, Phthazinyl, Di Benzosilyl, spiro two (dibenzosilyl), dihydrophenazinyl (dihydrophenazinyl group), phenanthoxazinyl, phenanthridyl (phenanthridyl group), imidazopyridyl, thienyl, indolo[ 2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[b,f]azepine, 9, 10-Dihydroacridinyl, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl, naphthyridinyl group, phenanthrazinyl, benzo[c][1, 2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl (5,10-dihydrodibenzo[b,e][1,4]azasilinyl) , pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indoline 5,11-dihydroindeno[1,2-b]carbazolyl and similar groups.

In this specification, the amine group can be selected from the group consisting of: monoalkylamine, monoarylamine, monoheteroarylamine, _-NH2 , dialkylamino, diarylamino An amino group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and although the number of carbon atoms is not particularly limited thereto, it is preferably 1 to 30. Specific examples of amine groups may include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, anilino, naphthylamine, benzidine, dibenzidine, anthraceneamino ( anthracenylamine group), 9-methyl-anthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine group, phenyltoluidine, triphenylamine, biphenylnaphthylamine, phenyl benzidine group, biphenylfluorenylamine group, phenyltriphenylenylamine group, biphenyltriphenylenylamine group, and the like.

In this specification, an aryl group means an aryl group having two bonding sites, that is, a divalent group. Except that each is a divalent group, the description provided above for aryl groups is applicable here. In addition, the heteroaryl group means a heteroaryl group having two bonding sites, that is, a divalent group. Except that each is a divalent group, the description provided above for heteroaryl groups applies here.

In this specification, the hole characteristic refers to the characteristic capable of forming a hole by supplying electrons when an electric field is applied, and means (by having a conduction characteristic along the HOMO energy level) that contributes to the formation of a hole formed in the anode. Hole injection into the light-emitting layer, the migration of holes formed in the light-emitting layer to the anode, and the characteristics of migration in the light-emitting layer.

Substituents with hole properties include substituted or unsubstituted C6 to C60 aryl groups with hole properties, substituted or unsubstituted C2 to C60 heteroaryl groups with hole properties, substituted or unsubstituted Substituted arylamine groups, substituted or unsubstituted heteroarylamine groups, or similar groups.

More specifically, the substituted or unsubstituted C6 to C60 aryl group having hole properties may be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spiro-fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, or combinations thereof.

More specifically, the substituted or unsubstituted C2 to C60 heteroaryl having hole properties is substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted Or unsubstituted dibenzothienyl, substituted or unsubstituted indolecarbazolyl or similar groups.

More specifically, the aryl or heteroaryl group, the substituent bonded to the nitrogen of the substituted or unsubstituted arylamine group and the substituted or unsubstituted heteroarylamine group may be substituted or unsubstituted Substituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted Chrysyl, substituted or unsubstituted triphenyl, substituted or unsubstituted perylene, substituted or unsubstituted indenyl, substituted or unsubstituted furyl, substituted or unsubstituted Substituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted Pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuryl, substituted or Unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted Isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxa Azinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenthiazinyl, Substituted or unsubstituted phenoxazinyl or a combination thereof.

In addition, the electron characteristic refers to a characteristic capable of receiving electrons when an electric field is applied, and means (by having a conduction characteristic along the LUMO level) that it facilitates injection of electrons formed in the cathode into the light-emitting layer, formed in the light-emitting layer The characteristics of electron migration to the cathode and in the light-emitting layer.

Substituted or unsubstituted C2 to C60 heteroaryl with electronic properties can be substituted or unsubstituted imidazolyl, substituted or unsubstituted tetrazolyl, substituted or unsubstituted quinoline substituted or unsubstituted isoquinolinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furyl, substituted or unsubstituted benzofuryl, substituted or unsubstituted isofuryl, substituted or unsubstituted benzisofuryl, substituted or unsubstituted Oxazolinyl, substituted or unsubstituted benzoxazolinyl, substituted or unsubstituted oxadiazolinyl, substituted or unsubstituted benzoxadiazolinyl, substituted or unsubstituted oxatriazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted isothiazoline, substituted or unsubstituted Benzisothiazolinyl, substituted or unsubstituted thiazoline, substituted or unsubstituted benzothiazolinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted benzo Pyridazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted benzopyrazinyl, substituted or unsubstituted phthalazinyl, substituted or unsubstituted benzoquinoline substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenanthrolinyl, substituted Or unsubstituted phenanthrazinyl or a combination thereof.

[化學式X-2]

[化學式X-3]

[化學式X-4]

[化學式X-5]

More specifically, the substituted or unsubstituted C2 to C60 heteroaryl group having electronic properties may be any of the following Chemical Formulas X-1 to X-5. [Chemical formula X-1]

[Chemical formula X-2]

[Chemical formula X-3]

[Chemical formula X-4]

[Chemical formula X-5]

In one embodiment of the present application, L ⁿ may be a direct bond (or a single bond), a substituted or unsubstituted arylylene, or a substituted or unsubstituted heteroarylylene.

In another embodiment, ^Ln can be a direct bond, a substituted or unsubstituted C6-C60 arylylene or a substituted or unsubstituted C2-C60 heteroarylylene.

In another embodiment, ^Ln can be a direct bond, a substituted or unsubstituted C6-C40 arylylene or a substituted or unsubstituted C2-C40 heteroarylylene.

In L ⁿ , n means the number for distinguishing substituents.

Hereinafter, a compound according to one embodiment will be described.

A compound according to one embodiment is represented by Chemical Formula 1 below. [chemical formula 1]

In Chemical Formula 1, Ar ¹ is a substituent with hole characteristics, R ¹ to R ²⁰ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl or substituted or unsubstituted Substituted C6 to C60 aryl, L ^{to L3} are each independently a single bond, substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl, and n1 to n3 are each independently one of the integers of 0 to 2.

By introducing various substituents into the structure of Chemical Formula 1, compounds having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents generally used as hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transfer layer materials, and charge generation layer materials for manufacturing organic light emitting diodes into the core structure , materials that satisfy the conditions required for each organic material layer can be synthesized.

In addition, by introducing various substituents into the structure of Chemical Formula 1, an energy band gap can be finely controlled, and at the same time, characteristics at an interface between organic materials can be enhanced, and material applications can become diversified.

At the same time, the compound has a high glass transition temperature (Tg), and thereby has excellent thermal stability. Such an increase in thermal stability becomes an important factor in providing drive stability to the device.

In one embodiment of the present application, Ar is ^substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, cyano, SiRR'R", substituted or unsubstituted amino, alkoxy (-OR) or arylthio (-SRa), Ra is a substituted or unsubstituted C6 to C60 aryl, R, R' and R" are the same as each other or Different, and each independently hydrogen, deuterium, -CN, substituted or unsubstituted C1 to C60 linear or branched chain alkyl, substituted or unsubstituted C3 to C60 monocyclic or multicyclic cycloalkyl , a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group or a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heteroaryl group.

More specifically, Ar ¹ may be a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C6 to C60 heteroaryl group.

More specifically, ^Ar is substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted Substituted 9,9-dialkylfluorenyl or substituted or unsubstituted 9,9-diarylfluorenyl, and the alkyl group of the dialkyl can be substituted or unsubstituted C1 to C10 alkyl And the aryl group of the diaryl group may be a substituted or unsubstituted C6 to C10 aryl group.

Additionally, ^Ar can be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or Unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted terphenyl group) or substituted or unsubstituted quaterphenyl group.

Additionally, ^Ar can be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or Unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted terphenyl, or substituted or unsubstituted biphenyl Phenyl, and the substituent may be phenyl or naphthyl.

When represented by such substituents, compared with other cases, the luminous efficiency and service life of the organic light emitting diode can be more excellent.

In addition, Ar ¹ may be represented by Chemical Formula 2 below. [chemical formula 2]

In Chemical Formula 2, Ar ² and Ar ³ are each independently substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl, each of X ¹ to X ³ is independently -N-, -CH- or -CR-, at least one of ^X1 to ^X3 is -N-, ^L4 and ^L5 are each independently a single bond, substituted or unsubstituted C6 to C60 stretches An aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, n4 and n5 are each independently one of the integers from 0 to 2, and * is a bonding position.

In one embodiment of the present application, Ar ² and Ar ³ of Chemical Formula 2 may each independently be a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C2-C60 heteroaryl group.

In another embodiment, Ar ² and Ar ³ of Chemical Formula 2 may each independently be a substituted or unsubstituted C6-C40 aryl group or a substituted or unsubstituted C2-C40 heteroaryl group.

In another embodiment, Ar ² and Ar ³ of Chemical Formula 2 may each independently be a C6-C40 aryl group or a C2-C40 heteroaryl group.

In another embodiment, Ar ² and Ar ³ of Chemical Formula 2 may each independently be a C6 to C40 monocyclic or polycyclic aromatic group.

In another embodiment, Ar ² and Ar ³ of Chemical Formula 2 may each independently be phenyl, biphenyl, or naphthyl.

In one embodiment of the present application, X ¹ to X ³ may be -N-.

In another embodiment, X ¹ can be -N-, and X ² and X ³ can be -CH-.

In another embodiment, ^X2 can be -N-, ^X1 and ^X3 can be -CH-.

In another embodiment, ^X3 can be -N-, and ^X1 and ^X2 can be -CH-.

In another embodiment, X ¹ can be -CH-, and X ² and X ³ can be -N-.

In another embodiment, ^X2 can be -CH-, and ^X1 and ^X3 can be -N-.

In another embodiment, ^X3 can be -CH-, and ^X1 and ^X2 can be -N-.

In one embodiment of the present application, L ⁴ and L ⁵ can each independently be a single bond, a substituted or unsubstituted C6 to C60 aryl, or a substituted or unsubstituted C2 to C60 heteroaryl base.

In another embodiment, ^L4 and ^L5 can each independently be a single bond or a substituted or unsubstituted C6-C60 aryl group.

In another embodiment, ^L4 and ^L5 can each independently be a single bond or a C6-C40 arylylene group.

In another embodiment, ^L4 and ^L5 can each independently be a single bond, a phenylene group or a biphenylene group.

When represented by such substituents, compared with other cases, the luminous efficiency and service life of the organic light emitting diode can be more excellent.

In addition, Ar ¹ may be represented by Chemical Formula 3 below. [chemical formula 3]

In Chemical Formula 3, R ²¹ and R ²² are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl or substituted or unsubstituted C6 to C60 aryl, and * is bond position.

In one embodiment of the present application, R ²¹ and R ²² of Chemical Formula 3 may each independently be hydrogen or a substituted or unsubstituted C6-C60 aryl group.

In another embodiment, R ²¹ and R ²² of Chemical Formula 3 may each independently be hydrogen or a substituted or unsubstituted C6-C40 aryl group.

In another embodiment, R ²¹ and R ²² of Chemical Formula 3 may each independently be hydrogen or a C6-C40 aryl group.

In another embodiment, R ²¹ and R ²² of Chemical Formula 3 may each independently be hydrogen or a C6 to C40 monocyclic or polycyclic aromatic group.

In another embodiment, R ²¹ and R ²² of Chemical Formula 3 may each independently be hydrogen, phenyl or naphthyl.

When represented by such substituents, compared with other cases, the luminous efficiency and service life of the organic light emitting diode can be more excellent.

In one embodiment of the present application, Ar ¹ may be represented by Chemical Formula 4 below. [chemical formula 4]

In Chemical Formula 4, A is O, S, SiRaRb or NRc, Ra to Rc are the same or different from each other, and are each independently substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl, R ³¹ to R ³⁵ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C6 to C60 aryl or substituted or Unsubstituted C2 to C60 heteroaryl, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, m is an integer from 0 to 3 , and * is the bonding position.

In one embodiment of the present application, Ra to Rc are the same or different from each other, and can each be independently substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl .

In another embodiment, Ra to Rc are the same or different from each other, and can each independently be a substituted or unsubstituted C6 to C40 aryl or a substituted or unsubstituted C2 to C40 heteroaryl.

In another embodiment, Ra to Rc are the same or different from each other, and each independently can be a C6 to C40 aryl group that is unsubstituted or substituted with a C1 to C10 alkyl group, or a C2 to C40 heteroaryl group.

In another embodiment, Ra to Rc are the same or different from each other, and each independently can be a C6 to C20 aryl group that is unsubstituted or substituted with a C1 to C10 alkyl group, or a C2 to C20 heteroaryl group.

In another embodiment, Ra to Rc are the same or different from each other, and may each independently be phenyl, biphenyl, naphthyl, dimethylfluorenyl or carbazolyl.

In one embodiment of the present application, R ³¹ to R ³⁵ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C6 to C60 aromatic or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

In another embodiment, R ³¹ to R ³⁵ are each independently hydrogen, substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl, or two adjacent One or more than two groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

In another embodiment, R ³¹ to R ³⁵ are each independently hydrogen, substituted or unsubstituted C6 to C40 aryl or substituted or unsubstituted C2 to C40 heteroaryl, or two adjacent One or more groups may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.

In another embodiment, R ³¹ to R ³⁵ are each independently hydrogen, C6 to C40 aryl unsubstituted or substituted by C1 to C10 alkyl, or C2 to C40 heteroaryl, or two adjacent Or more than two groups may be bonded to each other to form a C6 to C20 aromatic hydrocarbon ring.

In another embodiment, R ³¹ to R ³⁵ are each independently hydrogen, phenyl, biphenyl, naphthyl, dimethylfluorenyl or carbazolyl, or two or more adjacent groups can be bonded to each other to form a benzene ring.

In one embodiment of the present application, Ar ¹ may be represented by Chemical Formula 5 below. [chemical formula 5]

In Chemical Formula 5, R ³² to R ³⁵ and R ⁴¹ to R ⁴⁴ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C6 to C60 An aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, B is a direct bond or CRdRe, Re and Rd are the same or different from each other, and each independently is a substituted or unsubstituted C6 to C60 aryl or a substituted or unsubstituted C1 to C20 alkyl, and * is a bond Location.

In one embodiment of the present application, R ³² to R ³⁵ of Chemical Formula 5 have the same definitions as in Chemical Formula 4.

In one embodiment of the present application, R ⁴¹ to R ⁴⁴ of Chemical Formula 5 have the same definitions as R ³² to R ³⁵ of Chemical Formula 4.

In one embodiment of the present application, B of Chemical Formula 5 may be a direct bond.

When B is a direct bond in Chemical Formula 5, the following structures may be included.

In one embodiment of the present application, Rd and Re of Chemical Formula 5 are the same or different from each other, and can be independently substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C1 to C20 alkyl.

In another embodiment, Rd and Re of Chemical Formula 5 are the same or different from each other, and each independently can be a substituted or unsubstituted C1-C20 alkyl group.

In another embodiment, Rd and Re of Chemical Formula 5 are the same or different from each other, and each independently can be a substituted or unsubstituted C1-C10 alkyl group.

In another embodiment, Rd and Re of Chemical Formula 5 are the same or different from each other, and each independently is a C1 to C10 alkyl group.

In another embodiment, Rd and Re of Chemical Formula 5 are the same or different from each other, and each independently can be a C1 to C10 linear alkyl group.

In another embodiment, Rd and Re of Chemical Formula 5 are the same or different from each other, and may be each independently a methyl group.

In one embodiment of the present application, Ar ¹ may be cyano, SiRR'R", substituted or unsubstituted amine, alkoxy (-OR) or arylthio (-SRa).

In another embodiment, Ar ¹ can be: cyano; SiRR'R"; unsubstituted or substituted by one or more selected from the group consisting of C6 to C40 aryl and C2 to C40 heteroaryl alkoxy (-OR); or arylthio (-SRa).

In another embodiment, Ar can be: ^cyano ; SiRR'R"; unsubstituted or via phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, anthracenyl, and Amine substituted with one or more substituents selected from the group consisting of dimethylfluorenyl; alkoxy (-OR); or arylthio (-SRa).

In one embodiment of the present application, Ra may have the same definition as the aryl groups of R, R' and R" below.

In one embodiment of the present application, R, R' and R" are the same or different from each other, and are each independently hydrogen, deuterium, -CN, substituted or unsubstituted C1 to C60 straight chain or branched chain alkane substituted or unsubstituted C3 to C60 monocyclic or polycyclic cycloalkyl, substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl or substituted or unsubstituted C2 to C60 monocyclic Cyclic or polycyclic heteroaryl.

In another embodiment, R, R' and R" are the same or different from each other, and each independently can be a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.

In another embodiment, R, R' and R" are the same or different from each other, and each independently can be phenyl, biphenyl, naphthyl or anthracenyl.

Additionally, ^Ar is substituted phenyl or substituted naphthyl, and the substituents may be one or more substituents selected from the group consisting of substituted or unsubstituted aryl Amino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted aryloxy, and substituted or unsubstituted arylthiol.

When represented by such substituents, compared with other cases, the luminous efficiency and service life of the organic light emitting diode can be more excellent.

More specifically, ^L3 can be phenyl or naphthyl.

The compound of one example described above may be represented by any of the following compounds.

The compound or composition described above can be used in an organic photodiode, and a dry film forming method such as chemical vapor deposition can be used to form a compound for an organic photodiode or a compound for an organic photodiode. combination.

Hereinafter, an organic photodiode using the compound for an organic photodiode or the composition for an organic photodiode described above will be described.

The organic photodiode is not particularly limited as long as it is a device capable of interconverting electric energy and light energy, and examples thereof may include organic photodiodes, organic light emitting diodes, organic solar cells, organic photoconductive drums and the like.

Another embodiment of the present application provides an organic light emitting diode, and the organic light emitting diode includes: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed Between the first electrode and the second electrode, one or more layers of the organic material layer include the heterocyclic compound represented by Chemical Formula 1.

In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

In another embodiment, the first electrode can be a cathode and the second electrode can be an anode.

Specific details of the heterocyclic compound represented by Chemical Formula 1 are the same as the description provided above.

In one embodiment of the present application, the organic light emitting diode may be a blue organic light emitting diode, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting diode.

In one embodiment of the present application, the organic light emitting diode may be a green organic light emitting diode, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light emitting diode.

In one embodiment of the present application, the organic light emitting diode may be a red organic light emitting diode, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light emitting diode.

The organic light-emitting diodes of the present disclosure can be fabricated using general organic light-emitting diode fabrication methods and materials, except that the heterocyclic compounds described above are used to form one or more organic material layers.

When manufacturing an organic light emitting diode, a solution coating method and a vacuum deposition method may be used to form a heterocyclic compound as an organic material layer. Herein, the solution coating method means, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating method, and the like.

Herein, another example of an organic light emitting diode, one example of an organic photodiode, will be described with reference to the accompanying drawings.

1 to 3 illustrate a lamination sequence of electrodes and organic material layers of an organic light emitting diode according to an embodiment of the present application. However, the scope of the present application is not limited to these drawings, and structures of organic photodiodes known in the art may also be used in the present application.

FIG. 1 illustrates an organic light emitting diode in which an anode 200 , an organic material layer 300 , and a cathode 400 are sequentially laminated on a substrate 100 . However, the structure is not limited to such a structure, and as shown in FIG. 2 , an organic light emitting diode in which a cathode, an organic material layer, and an anode are successively laminated on a substrate may also be obtained.

FIG. 3 shows the case where the organic material layer is multilayered. The organic light emitting diode according to FIG. 3 comprises a hole injection layer 301 , a hole transfer layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transfer layer 305 and an electron injection layer 306 . However, the scope of the present application is not limited to such a laminated structure, and may not include layers other than the light emitting layer, and may further include other necessary functional layers, as necessary.

In an organic light emitting diode, the compound represented by Chemical Formula 1 may be used as a material of an electron transport layer, a hole transport layer, a hole blocking layer, a light emitting layer, or the like. More specifically, the compound represented by Chemical Formula 1 may be used as a material of an electron transfer layer in an organic light emitting diode.

A material having a relatively large work function can be used as the anode material, and a transparent conductive oxide, metal, conductive polymer, or the like can be used as the anode material. Specific examples of anode materials include (but are not limited to): metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conducting polymers such as poly(3-methylthiophene), poly[3,4-( Ethylene-1,2-dioxy)thiophene] (poly[3,4-(ethylene-1,2-dioxy)thiophene]; PEDOT), polypyrrole and polyaniline, and the like.

A material having a relatively small work function can be used as the cathode material, and a metal, metal oxide, conductive polymer, or the like can be used as the cathode material. Specific examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF/Al or LiO ₂ /Al, and the like.

A compound of one embodiment of the present disclosure or a known hole injection material can be used as the hole injection material, and for example: a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or a star starburst-type amine derivatives such as tris(4-carbazinyl-9-ylphenyl)amine described in the literature [Advanced Materials (Advanced Materials), 6, p. 677 (1994)] (tris(4-carbazoyl-9-ylphenyl)amine; TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (4,4',4"-tri[phenyl (m-tolyl)amino]triphenylamine; m-MTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (1,3,5-tris[4- (3-methylphenylphenylamino)phenyl]benzene; m-MTDAPB); conductive polymers with solubility, polyaniline/dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene)/poly(4- styrene sulfonate), polyaniline/camphorsulfonic acid, or polyaniline/poly(4-styrene-sulfonate); and similar materials.

The compound of one embodiment of the present disclosure or pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and similar materials can be used as the hole transfer material, and can also be Use low-molecular or high-molecular materials.

Metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, Cyananthraquinone dimethane and its derivatives, fluorenone derivatives, diphenylethylene dicyanide and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, and similar materials as electron transfer materials, and High-molecular materials and low-molecular materials can also be used as electron transfer materials.

As an example of an electron injection material, LiF is generally used in this field, however, the present application is not limited thereto.

The compound of one embodiment of the present disclosure or a material emitting red, green, or blue light may be used as a light emitting material, and two or more light emitting materials may be mixed and used as a light emitting material as necessary. Herein, two or more luminescent materials can be used by depositing as individual supplies or by premixing and depositing as one supply. In addition, a fluorescent material may also be used as the light emitting material, however, a phosphorescent material may also be used. A material that emits light by bonding electrons and holes injected from the anode and cathode, respectively, may be used alone as the light emitting material, however, a material having a host material and a dopant material that together participate in light emission may also be used as the light emitting material.

When mixing luminescent material hosts, hosts of the same series may be mixed, or hosts of different series may be mixed. For example, any two or more types of materials of N-type host material or P-type host material can be selected and used as the host material of the light emitting layer.

An organic light emitting diode according to an embodiment of the present application may be a top emission type, a bottom emission type, or a dual emission type depending on materials used.

1）製備化合物1-1Hereinafter, the above-described embodiments will be described in more detail by way of examples. However, the following examples are for illustrative purposes only and do not limit the scope of rights. ( Preparation of Compounds for Organic Photodiodes ) [ Preparation Example 1-1] Preparation of Compound 1

1) Preparation of compound 1-1

In a round bottom flask (rbf), 4-bromoaniline (15 g, 0.087 mmol), phenylboronic acid (15.9 g, 0.13 mmol), Pd(PPh ₃ )Cl ₂ ( 3 g, 4.35 mmol), sodium carbonate (18.44 g, 0.17 mmol), and a mixture of 1,4-dioxane/water (450 ml/150 ml) were refluxed at 120° C. for 1 hour. The resultant was extracted with dichloromethane and dried over MgSO ₄ . The resultant was adsorbed on silica gel and then separated using mc/Hex=1/1 column to obtain compound 1-1 (10 g, 68%). 2) Preparation of compound 1

In a one-neck round bottom flask (rbf), make [1,1'-biphenyl]-4-amine (4.2 g, 0.0249 mmol), 2-bromoindole[3,2,1-jk]carba azole (20 g, 0.062 mmol), Pd ₂ (dba) ₃ (1.14 g, 1.24 mmol), third Bu ₃ P (9.96 g, 4.98 mmol), sodium butoxide (11.9 g, 0.124 millimolar) and toluene (480 ml) were refluxed at 130°C for 3 hours. The solid produced in excess was filtered while washing with MeOH. The solid was introduced into 1,2-dichlorobenzene 10T and dissolved therein via reflux, then cooled and purified using a recrystallization method to obtain Compound 1 (7.75 g, 48%). [ Preparation Example 1-2]

48% 2

71% 3

70% 5

62% 10

75% 12

68% 26

67% 32

75% 46

80% 57

85% 45

73% 62

43% 70

86% 73

70% 82

54% 87

82% 90

77% 91

90% 108

68% [ 製備實例 2-1] 製備化合物 101

1 ） 製備化合物 101-1 The target compound (C) was synthesized in the same manner as in Preparation Example 1-1 using Intermediate A instead of Compound 1-1. [Form A] compound A B C Yield (A to C ) 1

48% 2

71% 3

70% 5

62% 10

75% 12

68% 26

67% 32

75% 46

80% 57

85% 45

73% 62

43% 70

86% 73

70% 82

54% 87

82% 90

77% 91

90% 108

68% [ Preparation Example 2-1] Preparation of Compound 101

1 ) Preparation of compound 101-1

In a one-neck round bottom flask (r.b.f), make carbazole (7.6 g, 46 mmol), 4-iodoaniline (10 g, 46 mmol), CuI (0.09 g, 0.47 mmol, 1% Cu), 1,2-diaminocyclohexane (0.6 ml, 5.0 mmol, 10 eq in Cu) and anhydrous potassium phosphate (21 g, 99 mmol, 2.2 eq) were dissolved in 1 , 4-dioxane (450 ml), and the resultant was refluxed for 10 hours. The reaction mixture was diluted with dichloromethane, and insoluble material was filtered off. The black oil obtained by removing the solvent from the filtrate by evaporation was absorbed with silica gel and then separated by column chromatography (MC/Hex: 1/3). Obtained as a solid (8 g, 68%). 2) Preparation of compound 101

The target compound 101(D) (15.1 g, 66%) was obtained in the same manner as the preparation of Compound 1 in Preparation Example 1, except that Compound 101-1(A) was used instead of Compound 1-1(A). [ Preparation Example 2-2]

65% 102

73% 103

61% 104

57% 105

45% 106

70% 107

71% 108

70% 115

47% 116

72% 120

75% 121

68% 143

70% 144

67% 156

43% 157

56% 163

70% 166

75% 193

82% 194

80% 195

65% 197

65% 216

78% 220

51% 225

58% 236

51% The target compound (D) was synthesized in the same manner as in Preparation Example 2-1 using Intermediate A instead of Compound 101-1. [Form B] compound A B D. Yield (A to D) 101

65% 102

73% 103

61% 104

57% 105

45% 106

70% 107

71% 108

70% 115

47% 116

72% 120

75% 121

68% 143

70% 144

67% 156

43% 157

56% 163

70% 166

75% 193

82% 194

80% 195

65% 197

65% 216

78% 220

51% 225

58% 236

51%

The prepared compounds were identified by NMR and mass (Mass) results. [Table 1] compound FD-quality compound FD-quality 1 m/z=647.78 (C48H29N3=647.24) 2 m/z=723.27 (C54H33N3=723.88) 3 m/z=687.27 (C51H33N3=687.85) 4 m/z=763.30 (C57H37N3=763.94) 5 m/z=661.22 (C48H27N3O=661.76) 6 m/z=737.25 (C54H31N3O=737.86) 7 m/z=661.22 (C48H27N3O=661.76) 8 m/z=737.25 (C54H31N3O=737.86) 9 m/z=661.22 (C48H27N3O=661.76) 10 m/z=737.25 (C54H31N3O=737.86) 11 m/z=811.30 (C61H37N3=811.99) 12 m/z=887.33 (C67H41N3=888.09) 13 m/z=621.22 (C46H27N3=621.74) 14 m/z=697.25 (C52H31N3=697.84) 15 m/z=697.25 (C52H31N3=697.84) 16 m/z=621.22 (C46H27N3=621.74) 17 m/z=697.25 (C52H31N3=697.84) 18 m/z=723.27 (C54H33N3=723.88) 19 m/z=823.30 (C62H37N3=824.00) 20 m/z=823.30 (C62H37N3=824.00) twenty one m/z=671.24 (C50H29N3=671.80) twenty two m/z=671.24 (C50H29N3=671.80) twenty three m/z=671.24 (C50H29N3=671.80) twenty four m/z=671.24 (C50H29N3=671.80) 25 m/z=747.27 (C56H33N3=747.90) 26 m/z=747.27 (C56H33N3=747.90) 27 m/z=747.27 (C56H33N3=747.90) 28 m/z=747.27 (C56H33N3=747.90) 29 m/z=747.27 (C56H33N3=747.90) 30 m/z=747.27 (C56H33N3=747.90) 31 m/z=747.27 (C56H33N3=747.90) 32 m/z=747.27 (C56H33N3=747.90) 33 m/z=746.88(C51H30N4OS=746.21) 34 m/z=797.28 (C60H35N3=797.96) 35 m/z=797.28 (C60H35N3=797.96) 36 m/z=797.28 (C60H35N3=797.96) 37 m/z=763.30 (C57H37N3=763.94) 38 m/z=763.30 (C57H37N3=763.94) 39 m/z=813.31 (C61H39N3=814.00) 40 m/z=813.31 (C61H39N3=814.00) 41 m/z=813.31 (C61H39N3=814.00) 42 m/z=813.31 (C61H39N3=814.00) 43 m/z=747.27 (C56H33N3=747.90) 44 m/z=671.24 (C50H29N3=671.80) 45 m/z=747.27 (C56H33N3=747.90) 46 m/z=797.28 (C60H35N3=797.96) 47 m/z=823.30 (C62H37N3=824.00) 48 m/z=747.27 (C56H33N3=747.90) 49 m/z=823.30 (C62H37N3=824.00) 50 m/z=797.28 (C60H35N3=797.96) 51 m/z=797.28 (C60H35N3=797.96) 52 m/z=873.31 (C66H39N3=874.06) 53 m/z=671.24 (C50H29N3=671.80) 54 m/z=747.27 (C56H33N3=747.90) 55 m/z=811.30 (C61H37N3=811.99) 56 m/z=811.30 (C61H37N3=811.99) 57 m/z=887.33 (C67H41N3=888.09) 58 m/z=809.28 (C61H35N3=809.97) 59 m/z=809.28 (C61H35N3=809.97) 60 m/z=887.33 (C67H41N3=888.09) 61 m/z=695.24 (C52H29N3=695.82) 62 m/z=771.27 (C58H33N3=771.92) 63 m/z=695.24 (C52H29N3=695.82) 64 m/z=771.27 (C58H33N3=771.92) 65 m/z=787.26 (C58H33N3O=787.92) 66 m/z=737.25 (C54H31N3O=737.86) 67 m/z=787.26 (C58H33N3O=787.92) 68 m/z=737.25 (C54H31N3O=737.86) 69 m/z=661.22 (C48H27N3O=661.76) 70 m/z=737.25 (C54H31N3O=737.86) 71 m/z=737.25 (C54H31N3O=737.86) 72 m/z=787.26 (C58H33N3O=787.92) 73 m/z=813.28 (C60H35N3O=813.96) 74 m/z=813.28 (C60H35N3O=813.96) 75 m/z=813.28 (C60H35N3O=813.96) 76 m/z=813.28 (C60H35N3O=813.96) 77 m/z=813.28 (C60H35N3O=813.96) 78 m/z=813.28 (C60H35N3O=813.96) 79 m/z=813.28 (C60H35N3O=813.96) 80 m/z=813.28 (C60H35N3O=813.96) 81 m/z=723.27 (C54H33N3=723.88) 82 m/z=799.30 (C60H37N3=99.98) 83 m/z=799.30 (C60H37N3=799.98) 84 m/z=773.28 (C58H35N3=773.94) 85 m/z=773.28 (C58H35N3=773.94) 86 m/z=773.28 (C58H35N3=773.94) 87 m/z=799.30 (C60H37N3=799.98) 88 m/z=725.26 (C52H31N5=725.86) 89 m/z=726.25 (C51H30N6=726.84) 90 m/z=801.29 (C58H35N5=801.95) 91 m/z=802.28 (C57H34N6=802.94) 92 m/z=802.28 (C57H34N6=802.94) 93 m/z=802.28 (C57H34N6=802.94) 94 m/z=723.27 (C54H33N3=723.88) 95 m/z=877.32 (C64H39N5=878.05) 96 m/z=878.32 (C63H38N6=879.04) 97 m/z=953.35 (C70H43N5=954.15) 98 m/z=954.35 (C69H42N6=955.14) 99 m/z=877.32 (C64H39N5=878.05) 100 m/z=878.32 (C63H38N6=879.04) 101 m/z=736.26 (C54H32N4=736.88) 102 m/z=812.29 (C60H36N4=812.98) 103 m/z=736.26 (C54H32N4=736.88) 104 m/z=812.29 (C60H36N4=812.98) 105 m/z=888.33 (C66H40N4=889.07) 106 m/z=888.33 (C66H40N4=889.07) 107 m/z=738.28 (C54H34N4=738.89) 108 m/z=814.31 (C60H38N42=814.99) 109 m/z=838.31 (C62H38N4=839.01) 110 m/z=890.34 (C66H42N4=891.09) 111 m/z=814.31 (C60H38N4=814.99) 112 m/z=814.31 (C60H38N4=814.99) 113 m/z=738.28 (C54H34N4=738.89) 114 m/z=814.31 (C60H38N4=814.99)) 115 m/z=828.29 (C60H36N4O=828.98) 116 m/z=828.29 (C60H36N4O=828.98) 117 m/z=828.29 (C60H36N4O=828.98) 118 m/z=828.29 (C60H36N4O=828.98) 119 m/z=854.34 (C63H42N4=855.06) 120 m/z=854.34 (C63H42N4=855.06) 121 m/z=854.34 (C63H42N4=855.06) 122 m/z=854.34 (C63H42N4=855.06) 123 m/z=878.30 (C64H38N4O=879.03) 124 m/z=878.30 (C64H38N4O=879.03) 125 m/z=878.30 (C64H38N4O=879.03) 126 m/z=878.30 (C64H38N4O=879.03) 127 m/z=904.36 (C67H44N4=905.12) 128 m/z=904.36 (C67H44N4=905.12) 129 m/z=904.36 (C67H44N4=905.12) 130 m/z=904.36 (C67H44N4=905.12) 131 m/z=878.30 (C64H38N4O=879.03) 132 m/z=878.30 (C64H38N4O=879.03) 133 m/z=878.30 (C64H38N4O=879.03) 134 m/z=878.30 (C64H38N4O=879.03) 135 m/z=788.29 (C58H36N4=788.95) 136 m/z=788.29 (C58H36N4=788.95) 137 m/z=838.31 (C62H38N4=839.01) 138 m/z=838.31 (C62H38N4=839.01) 139 m/z=838.31 (C62H38N4=839.01) 140 m/z=890.34 (C66H42N4=891.09) 141 m/z=970.40 (C72H50N4=971.22) 142 m/z=918.30 (C66H38N4O2=919.06) 143 m/z=812.29 (C60H36N4=812.98) 144 m/z=812.29 (C60H36N4=812.98) 145 m/z=812.29 (C60H36N4=812.98) 146 m/z=812.29 (C60H36N4=812.98) 147 m/z=888.33 (C66H40N4=889.07) 148 m/z=888.33 (C66H40N4=889.07) 149 m/z=888.33 (C66H40N4=889.07) 150 m/z=888.33 (C66H40N4=889.07) 151 m/z=966.37 (C72H46N4=967.19) 152 m/z=964.36 (C72H44N4=965.17) 153 m/z=964.36 (C72H44N4=965.17) 154 m/z=786.28 (C58H34N4=786.94) 155 m/z=786.28 (C58H34N4=786.94) 156 m/z=778.31 (C57H38N4=778.96) 157 m/z=901.32 (C66H39N5=902.07) 158 m/z=901.32 (C66H39N5=902.07) 159 m/z=854.34 (C63H42N4=855.06) 160 m/z=854.34 (C63H42N4=855.06) 161 m/z=854.34 (C63H42N4=855.06) 162 m/z=854.34 (C63H42N4=855.06) 163 m/z=905.32 (C66H43N3Si=906.18) 164 m/z=905.32 (C66H43N3Si=906.18) 165 m/z=677.19 (C48H27N3S=677.83) 166 m/z=753.22 (C54H31N3S=753.92) 167 m/z=829.26 (C60H35N3S=830.02) 168 m/z=753.22 (C54H31N3S=753.92) 169 m/z=677.19 (C48H27N3S=677.83) 170 m/z=753.22 (C54H31N3S=753.92) 171 m/z=829.26 (C60H35N3S=830.02) 172 m/z=753.22 (C54H31N3S=753.92) 173 m/z=753.22 (C54H31N3S=753.92) 174 m/z=753.22 (C54H31N3S=753.92) 175 m/z=844.27 (C60H36N4S=845.04) 176 m/z=844.27 (C60H36N4S=845.04) 177 m/z=844.27 (C60H36N4S=845.04) 178 m/z=844.27 (C60H36N4S=845.04) 179 m/z=950.25 (C66H38N4S2=951.18) 180 m/z=697.23 (C50H27N5=697.80) 181 m/z=773.26 (C56H31N5=773.90) 182 m/z=672.23 (C49H28N4=672.79) 183 m/z=748.26 (C55H32N4=748.89) 184 m/z=697.23 (C50H27N5=697.80) 185 m/z=672.23 (C49H28N4=672.79) 186 m/z=748.26 (C55H32N4=748.89) 187 m/z=849.29 (C62H35N5=850.00) 188 m/z=849.29 (C62H35N5=850.00) 189 m/z=799.30 (C60H37N3=799.98) 190 m/z=875.33 (C66H41N3=876.07) 191 m/z=799.30 (C60H37N3=799.98) 192 m/z=875.33 (C66H41N3=876.07) 193 m/z=736.26 (C54H32N4=736.88) 194 m/z=812.29 (C60H36N4=812.98) 195 m/z=812.29 (C60H36N4=812.98) 196 m/z=812.29 (C60H36N4=812.98) 197 m/z=852.33 (C63H40N4=853.04) 198 m/z=852.33 (C63H40N4=853.04) 199 m/z=852.33 (C63H40N4=853.04) 200 m/z=852.33 (C63H40N4=853.04) 201 m/z=786.28 (C58H34N4=786.94) 202 m/z=786.28 (C58H34N4=786.94) 203 m/z=736.26 (C54H32N4=736.88) 204 m/z=812.29 (C60H36N4=812.98) 205 m/z=786.28 (C58H34N4=786.94) 206 m/z=786.28 (C58H34N4=786.94) 207 m/z=736.26 (C54H32N4=736.88) 208 m/z=812.29 (C60H36N4=812.98) 209 m/z=812.29 (C60H36N4=812.98) 210 m/z=786.28 (C58H34N4=786.94) 211 m/z=786.28 (C58H34N4=786.94) 212 m/z=862.31 (C64H38N4=863.04) 213 m/z=862.31 (C64H38N4=863.04) 214 m/z=862.31 (C64H38N4=863.04) 215 m/z=862.31 (C64H38N4=863.04) 216 m/z=812.29 (C60H36N4=812.98) 217 m/z=812.29 (C60H36N4=812.98) 218 m/z=862.31 (C64H38N4=863.04) 219 m/z=862.31 (C64H38N4=863.04) 220 m/z=734.25 (C54H30N4=734.86) 221 m/z=810.28 (C60H34N4=810.96) 222 m/z=860.29 (C64H36N4=861.02) 223 m/z=860.29 (C64H36N4=861.02) 224 m/z=663.23 (C48H29N3O=663.78) 225 m/z=739.26 (C54H33N3O=739.88) 226 m/z=739.26 (C54H33N3O=739.88) 227 m/z=679.21 (C48H29N3S=679.84) 228 m/z=755.24 (C54H33N3S=755.94) 229 m/z=755.24 (C54H33N3S=755.94) 230 m/z=930.37 (C69H46N4=931.15) 231 m/z=930.37 (C69H46N4=931.15) 232 m/z=930.37 (C69H46N4=931.15) 233 m/z=930.37 (C69H46N4=931.15) 234 m/z=904.32 (C66H40N4O=905.07) 235 m/z=904.32 (C66H40N4O=905.07) 236 m/z=904.32 (C66H40N4O=905.07) 237 m/z=904.32 (C66H40N4O=905.07) [Table 2] compound ¹ H NMR (CDCl ₃ , 200Mz) 1 δ=8.19 (4H,d), 7.75 (2H,d), 7.55~7.37 (15H,m), 7.20 (4H,t), 7.09 (2H,s) 2 δ=8.19 (4H,d), 7.75 (2H,d), 7.58~7.37 (15H,m) 7.5~7.20 (8H,m), 7.09 (2H,s) 3 δ=8.19 (4H,d), 7.90~7.86 (2H,m), 7.58~7.50 (9H,m), 7.38~7.20 (8H,m), 7.09 (2H,s), 1.69 (2H,s) 5 δ=8.19 (4H,d), 8.03~7.98 (4H,m), 7.80 (1H,s) 7.58~7.50 (9H,m), 7.20 (4H,s), 7.09 (2H,s), 6.91 (1H , d) 10 δ=8.19 (4H,d), 8.08~7.98 (3H,m),7.58 ~7.50 (12H,m), 7.39 ~7.31 (4H,m), 7.20 (4H,s), 7.09 (2H,s) 12 δ=8.19 (4H,d), 8.09 (1H,d), 7.90~7.10 (2H,m), 7.78 (1H,d), 7.58~ 7.50 (4H,m), 7.38~7.37 (3H,m), 7.28~7.09 (18H,m) 26 δ=9.11 (1H,d), 8.70 (1H,d), 8.46~8.43 (2H,m), 8.19 (4H,d), 7.92~7.90 (2H,m), 7.75~7.50 (12H,m), 7.37 (2H,d), 7.20 (4H,t), 7.09 (4H,s) 32 δ=9.08 (1H,d), 8.84 (1H,d), 8.27~8.19 (5H,m), 8.05 (1H,s), 7.90 (1H,d), 7.70~7.50 (13H,m), 7.20~ 7.09 (11H,m) 46 δ=8.95 (1H,d), 8.50 (1H,d), 8.21~8.19 (9H,m), 8.09 (1H,d), 7.77 (1H,t), 7.58~7.39 (14H,m), 7.20 ( 4H,t), 7.09 (4H,s) 57 δ=8.19~8.18 (5H,m), 7.90 (1H,d), 7.74~7.68 (2H,m), 7.58~7.55 (11H,m), 7.38~7.37 (3H,m), 7.28~7.09 (19H ,m) 62 δ=8.52 (1H,d), 8.31 (1H,d), 8.19~8.08 (9H,m), 7.92 (1H,d), 7.70 (1H,d), 7.58~7.50 (10H,m), 7.37 ( 2H,d), 7.20 (4H,t), 7.09 (4H,s) 70 δ=8.19 (4H,d), 7.98 (1H,d), 7.82 (1H,d), 7.69 (1H,d), 7.58~7.50 (12H m), 7.39~7.37 (4H,m), 7.20 (4H ,t), 7.09 (4H,s) 73 δ=8.19 (4H,d), 7.98 (1H,d), 7.82 (1H,d), 7.69 (1H,d), 7.58~7.50 (12H,m), 7.39~7.20 (12H,m), 7.09 ( 4H,s) 82 δ=8.19 (4H,d), 8.04 (3H,s), 7.75 (4H,d), 7.58~7.37 (18H,m), 7.20 (4H,t), 7.09 (4H,s) 87 δ=8.19 (4H,d), 8.04 (3H,s), 7.75 (4H,d), 7.58~7.41 (15H,m), 7.27~7.17 (7H,m), 7.09 (4H,s) 90 δ=8.23~8.19 (5H,m), 8.01~7.94 (6H,m), 7.58~7.49 (14H,m), 7.37 (2H,d), 7.20 (4H,t), 7.09 (4H,s) 91 δ=8.36 (4H,d), 8.19 (4H,d), 8.01 (2H,d), 7.58~7.50 (14H,m), 7.37 (2H,d), 7.20 (4H,t), 7.09 (4H, s) 101 δ=8.55 (1H,d), 8.19 (5H,d), 7.94 (1H,d), 7.69 (2H,d), 7.58~7.50 (10H,m), 7.35~7.32 (3H,m), 7.20~ 7.09 (10H,m) 102 δ=8.55 (1H,d), 8.19 (5H,d), 7.94~7.91 (5H,m), 7.58~7.50 (12H,m), 7.37~7.35 (3H,m), 7.20~7.09 (10H,m ) 103 δ=8.55 (1H,d), 8.19 (6H,d),7.94 (1H,d), 7.58~7.45 (11H,m), 7.20~7.04 (12H,m) 104 δ=8.55 (1H,d), 8.19 (5H,d), 7.94~7.91 (5H,m), 7.58~7.50 (11H,m), 7.20~7.09 (12H,m) 105 δ=8.62 (1H,d), 8.22~8.19 (5H,m), 7.92 (1H,d), 7.75~7.69 (8H,m), 7.58~7.32 (14H,m), 7.09 (4H,s) 106 δ=8.30 (1H,d),8.19~8.13 (5H,m), 7.99 (1H,d), 7.89 (1H,s), 7.77~7.69 (7H,m), 7.58~7.32 (16H,m), 7.20 (4H,t), 7.09 (4H,s) 107 δ=8.19 (4H,d), 7.58~7.50 (8H,m), 7.24~7.04 (20H,m) 108 δ=8.19 (4H,d), 7.58~7.50 (12H,m), 7.37 (4H,d), 7.24~7.20 (8H,m), 7.09~7.00 (10H,m) 115 δ=8.19 (4H,d), 7.08 (1H,d), 7.58~7.50 (9H,m), 7.38~7.00 (21H,m) 116 δ=8.22~8.19 (5H,d), 7.98 (1H,d), 7.58~7.50 (10H,m), 7.39~6.97 (13H,m) 120 δ=8.19 (4H,d), 7.90 (1H,d), 7.62~7.50 (11H,m), 7.28~7.00 (19H,m), 1.69 (6H,s) 121 δ=8.19 (4H,d), 7.90~7.86 (2H,m), 7.58~7.50 (9H,m), 7.38~7.00 (22H,m) 143 δ=8.55 (1H,d), 8.19 (4H,d),7.94~7.93 (2H,m), 7.69~7.68 (3H,d), 7.58~7.32 (15H,m), 7.20~7.09 (9H,m ) 144 δ=8.55 (1H,d), 8.19 (4H,d), 7.99~7.89 (3H,m), 7.77~7.69 (5H,m), 7.58~7.32 (14H,m), 7.20~7.09 (9H,m ) 156 δ=8.19 (4H,d), 7.58~7.50 (8H,m), 7.20~7.09 (18H,m), 6.95 (2H,t), 1.69 (6H,s) 157 δ=8.55 (2H,d), 8.19 (5H,d), 7.94 (2H,d), 7.72~7.69 (4H,m), 7.58~7.50 (10H,m), 7.38~7.32 (5H,m), 7.20~7.09 (11H,m) 163 δ=8.19 (4H,d), 7.87 (2H,d), 7.58~7.38 (26H,m), 7.20 (4H,t), 7.09 (4H,s) 166 δ=8.55 (1H,d),8.45 (1H,d), 8.32 (1H,d), 8.19 (4H,d), 7.93 (1H,d), 7.70 (1H,t), 7.58~7.49 (11H, m), 7.37 (2H,d), 7.20 (4H,t), 7.09 (4H,s) 193 δ=8.19 (5H,d), 8.01 (1H,s), 7.90 (1H,d), 7.62~7.50 (15H,m), 7.20 (4H,t), 7.09 (4H,s), 6.48 (1H, d) 194 δ=8.19 (5H,d), 8.01 (1H,s), 7.92~7.90 (5H,m), 7.75 (1H,d), 7.58~7.41 (13H,m), 7.20 (4H,t), 7.09 ( 4H,s), 6.48 (1H,d) 195 δ=8.21~8.19 (6H,m), 8.01 (1H,s), 7.90 (1H,d), 7.68~7.41 (18H,m), 7.20 (4H,t), 7.09 (4H,s), 6.48 ( 1H, d) 197 δ=8.19 (5H,d), 8.01 (1H,s), 7.90~7.86 (3H,m), 7.58~7.50 (12H,m), 7.40~7.38 (2H,m), 7.2~7.20 (6H,m ), 7.09 (4H,s), 6.48 (1H,d) 216 δ=8.21~8.19 (6H,m), 8.04 (1H,d), 7.62~7.50 (18H,m), 7.37 (2H,d), 7.20 (5H,t), 7.09 (4H,s) 220 δ=8.24~8.19 (7H,m), 7.72 (1H,d), 7.58~7.50 (10H,m), 7.29~7.20 (12H,m), 7.09 (4H,s) 225 δ=8.19 (4H,d), 7.78~7.75 (4H,m), 7.58~7.41 (11H,m), 7.27~7.09 (2H,m), 6.85 (2H,d) 236 δ=8.19 (4H,d), 8.03~7.98 (2H,m), 7.80~7.75 (3H,m), 7.58~7.31 (18H,m), 7.20~7.09 (12H,m), 6.91 (2H,d ) [ Experimental Example ] Experiment: Manufacturing Organic Light-Emitting Diodes

The glass substrate was ultrasonically cleaned with distilled water, and ITO was coated on the glass substrate as a thin film in a thickness of 1,500 angstroms. After cleaning with distilled water, the substrate was ultrasonically cleaned with a solvent such as acetone, methanol, and isopropanol, followed by drying and UVO treatment using UV in a UV cleaner for 5 minutes. Thereafter, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum for ITO work function and residual film removal, and the substrate was transferred to thermal deposition equipment for organic deposition.

On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine) and hole transfer Layer NPB (N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenylyl)-4,4'-diamine).

The light-emitting layer is thermally vacuum-deposited thereon as follows. The compounds described in Table 4 below were used as hosts and Ir(ppy) ₃ was doped as green phosphorescent by doping tris(2-phenylpyridine)iridium (Ir(ppy) ₃ ) by 7% to the host. dopant to deposit the emissive layer to 400 angstroms. Thereafter, BCP was deposited to 60 Å as a hole blocking layer, and Alq ₃ was deposited thereon to 200 Å as an electron transfer layer. Finally, an electron injection layer was formed on the electron transfer layer by depositing lithium fluoride (LiF) to a thickness of 10 Å, and then by depositing an aluminum (Al) cathode to a thickness of 1,200 Å on the electron injection layer. A cathode is formed, and thus, an organic electroluminescent diode is fabricated.

Simultaneously, all organic compounds required for OLED fabrication were vacuum sublimated purified at 10 ⁻⁶ Torr to 10 ⁻⁸ Torr for each material used in OLED fabrication.

化合物II

化合物III

化合物IV

化合物V

化合物VI

評估 ： 有機電致發光二極體的驅動電壓及發光效率 Herein, the hole transfer compounds of Comparative Examples are shown in Table 3 below. [table 3] Compound I

Compound II

Compound III

Compound IV

Compound V

Compound VI

Evaluation : Driving Voltage and Luminous Efficiency of Organic Electroluminescent Diodes

For the organic electroluminescent diode manufactured as above, electroluminescent (EL) characteristics were measured using M7000 manufactured by McScience Inc., and from the measurement results, when the standard luminance At 6,000 cd/m², T90 was measured using a service life measurement system (M6000) manufactured by Mc Scientific. The characteristics of the organic electroluminescent diodes of the present disclosure are shown in Table 4. [Table 4] hole transfer compound Driving voltage (V) Efficiency (cd/A) Service life (T ₉₀ ) Comparative example 1 I 4.18 116.76 164 Comparative example 2 II 4.15 118.80 166 Comparative example 3 III 4.19 120.12 170 Comparative example 4 IV 4.10 122.05 168 Comparative Example 5 V 4.12 119.70 160 Comparative example 6 VI 4.14 120.12 169 Example 1 1 3.75 130.31 230 Example 2 2 3.80 132.22 240 Example 3 3 3.82 140.00 250 Example 4 4 3.93 138.82 258 Example 5 5 3.94 144.01 253 Example 6 6 3.92 143.87 264 Example 7 7 3.79 139.91 252 Example 8 8 3.79 139.95 270 Example 9 9 3.80 134.45 272 Example 10 10 3.82 136.46 271 Example 11 11 3.85 138.88 224 Example 12 12 3.80 138.35 250 Example 13 13 3.70 140.44 243 Example 14 14 3.79 148.81 322 Example 15 15 3.74 148.45 323 Example 16 16 3.76 149.75 325 Example 17 17 3.80 149.11 330 Example 18 18 3.80 150.85 342 Example 19 19 3.78 149.15 329 Example 20 20 3.80 148.97 330 Example 21 twenty one 3.84 147.89 324 Example 22 twenty two 3.79 149.99 320 Example 23 twenty three 3.76 152.25 327 Example 24 twenty four 3.74 150.67 328 Example 25 25 3.80 150.69 330 Example 26 26 3.77 149.71 329 Example 27 27 3.75 150.89 340 Example 28 28 3.81 151.31 342 Example 29 29 3.76 149.99 341 Example 30 30 3.79 147.95 328 Example 31 31 3.74 148.99 330 Example 32 31 3.78 150.25 328 Example 33 32 3.80 151.74 327 Example 34 34 3.75 149.86 346 Example 35 35 3.79 148.88 340 Example 36 40 3.79 150.11 330 Example 37 45 3.77 151.67 327 Example 38 47 3.75 150.11 326 Example 39 49 3.77 149.13 329 Example 40 50 3.73 150.71 320 Example 41 55 3.77 149.61 326 Example 42 57 3.79 148.65 329 Example 43 58 3.74 150.36 328 Example 44 59 3.75 151.77 330 Example 45 60 3.81 150.44 324 Example 46 64 3.85 151.12 340 Example 47 65 3.87 154.41 341 Example 48 71 3.89 149.99 342 Example 49 72 3.80 150.07 333 Example 50 73 3.76 150.00 338 Example 51 82 3.79 151.32 328 Example 52 87 3.84 152.72 330 Example 53 90 3.76 151.99 324 Example 54 91 3.82 153.12 322 Example 55 101 3.79 151.25 335 Example 56 102 3.80 150.03 320 Example 57 103 3.79 149.79 337 Example 58 104 3.84 149.71 329 Example 59 105 3.82 152.11 320 Example 60 106 3.82 148.01 318 Example 61 107 3.85 150.36 324 Example 62 108 3.80 150.11 314 Example 63 115 3.80 148.89 320 Example 64 116 3.80 147.90 333 Example 65 120 3.79 149.05 324 Example 66 121 3.84 148.65 230 Example 67 143 3.77 140.31 234 Example 68 144 3.77 144.02 240 Example 69 156 3.76 140.99 272 Example 70 157 3.75 144.82 260 Example 71 163 3.80 143.87 270 Example 72 166 3.83 143.91 261 Example 73 193 3.83 142.05 230 Example 74 194 3.84 139.95 234 Example 75 195 3.88 139.45 235 Example 76 197 3.81 142.46 274 Example 77 216 3.80 146.88 230 Example 78 220 3.79 144.35 254 Example 79 225 3.77 147.81 320 instance 80 236 3.76 146.45 320

As can be seen from the results in Table 4, the organic light emitting diode using the hole transport layer material of the blue organic light emitting diode of the present disclosure has a lower driving voltage and improved Luminous efficiency and service life.

In the above, the preferred examples of the present disclosure have been described in detail, however, the scope of rights of the present disclosure is not limited thereto, and those skilled in the art make use of the basic concepts of the present disclosure defined in the appended patent scope. Various modifications and improvements also belong to the scope of rights of the content of this disclosure.

100: Substrate 200: anode 300: organic material layer 301: Hole injection layer 302: Hole transfer layer 303: luminous layer 304: Hole blocking layer 305: Electron transfer layer 306: Electron injection layer 400: Cathode

1 to 3 are cross-sectional views each illustrating an organic light emitting diode according to an embodiment of the present specification.

100: Substrate

200: anode

300: organic material layer

400: Cathode

Claims (11)

A compound represented by the following chemical formula 1:

Wherein, in Chemical Formula 1, Ar ¹ is a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C6 to C60 heteroaryl group; R ¹ to R ²⁰ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl or substituted or unsubstituted C6 to C60 aryl; L to ^{L3 are} each independently a single bond, substituted or unsubstituted C6 to C60 arylylene or substituted or unsubstituted C2 to C60 heteroaryl; and n1 and n2 are each independently 0, n3 is one of the integers from 0 to 2. The compound as claimed in claim ¹ , wherein Ar is: (1) substituted or unsubstituted carbazolyl; (2) substituted or unsubstituted dibenzofuranyl; (3) substituted or Unsubstituted dibenzothienyl; (4) substituted or unsubstituted 9,9-dialkylfluorenyl, and the alkyl in the dialkyl is substituted or unsubstituted C1 to C10 alkane or (5) a substituted or unsubstituted 9,9-diarylfluorenyl group, and the aryl group in the diaryl group is a substituted or unsubstituted C6 to C10 aryl group. The compound as claimed in claim ¹ , wherein Ar is: (1) substituted or unsubstituted naphthyl; (2) substituted or unsubstituted anthracenyl; (3) substituted or unsubstituted (4) substituted or unsubstituted pyrenyl; (5) substituted or unsubstituted terphenyl; (6) substituted or unsubstituted terphenyl; or (7) Substituted or unsubstituted p-tetraphenylene. The compound as described in claim 1, wherein Ar ¹ is represented by the following chemical formula 2:

In Chemical Formula 2, Ar ² and Ar ³ are each independently substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl; X ¹ to X ³ are each independently -N-, -CH - or -CR-, and at least one of X ¹ to X ³ is -N-; R is deuterium, -CN, substituted or unsubstituted C1 to C60 straight or branched chain alkyl, substituted or Unsubstituted C3 to C60 monocyclic or polycyclic cycloalkyl, substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl, or substituted or unsubstituted C2 to C60 monocyclic or polycyclic hetero Aryl; L and ^L are each independently a single bond, substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted C2 to C60 heteroaryl; n4 ^and n5 are each independently is one of the integers from 0 to 2; and * is the bonding position. The compound as described in claim 1, wherein Ar ¹ is represented by the following chemical formula 3:

In Chemical Formula 3, R ²¹ and R ²² are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C60 alkyl or substituted or unsubstituted C6 to C60 aryl; and * is bond position. The compound as claimed in claim 1, wherein Ar is substituted phenyl or substituted naphthyl; and the substituent is one or more substituents ^selected from the group consisting of: substituted or unsubstituted arylamine, substituted or unsubstituted heteroarylamine, substituted or unsubstituted aryloxy, and substituted or unsubstituted arylthiol. The compound as claimed in claim 1, wherein L ³ is phenyl or naphthyl. The compound as described in claim 1, wherein the compound represented by Chemical Formula 1 is any one of the following compounds:

An organic photodiode, comprising: an anode and a cathode facing each other; and at least one organic layer, disposed between the anode and the cathode, wherein the organic layer includes as claimed in claim 1 to claim 8 The compound described in any one. The organic photodiode as claimed in claim 9, wherein the organic layer includes a hole transfer layer, a light emitting layer, a hole injection layer or a combination thereof, and the hole transfer layer, the light emitting layer or the The hole injection layer includes the compound. A display device, comprising the organic photodiode as described in Claim 9 or Claim 10.

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