KR101909680B1 - Compound, organic optoelectric device and display device - Google Patents

Compound, organic optoelectric device and display device Download PDF

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KR101909680B1
KR101909680B1 KR1020150051093A KR20150051093A KR101909680B1 KR 101909680 B1 KR101909680 B1 KR 101909680B1 KR 1020150051093 A KR1020150051093 A KR 1020150051093A KR 20150051093 A KR20150051093 A KR 20150051093A KR 101909680 B1 KR101909680 B1 KR 101909680B1
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이승재
김병구
김영권
류진현
유은선
장기포
정수영
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삼성에스디아이 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L51/50—

Abstract

And a display device including the organic optoelectronic device.
[Chemical Formula 1]

Figure 112015035381976-pat00067

(Wherein X 1 to X 4 , L 1 , L 2 , and R 1 to R 4 are as defined in the specification).

Description

TECHNICAL FIELD [0001] The present invention relates to a compound, an organic optoelectronic device including the same, and a display device.

Organic optoelectronic devices, and display devices.

Organic optoelectronic devices are devices that can switch between electrical and optical energy.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle. One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, the electron and hole are transferred to different electrodes to generate electric energy, and the other is a voltage / Emitting device that generates light energy from energy.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

In recent years, organic light emitting diodes (OLEDs) have attracted considerable attention due to the demand for flat panel display devices. The organic light emitting diode is a device for converting electrical energy into light by applying an electric current to the organic light emitting material, and usually has an organic layer inserted between an anode and a cathode. The organic layer may include a light emitting layer and an optional auxiliary layer. The auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, And a hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and the organic layer is highly affected by the organic material contained in the organic layer.

In particular, in order for the organic light emitting device to be applied to a large-sized flat panel display device, it is necessary to develop an organic material capable of increasing the mobility of holes and electrons and increasing the electrochemical stability.

High efficiency, long life, and the like.

An organic optoelectronic device including the compound, and a display device including the organic optoelectronic device.

In one embodiment of the present invention, there is provided a compound represented by the following formula (1).

[Chemical Formula 1]

Figure 112015035381976-pat00001

In Formula 1,

X 1 to X 4 are each independently N, C, CH, or CL a -R a ,

At least one of X 1 to X 4 is N,

L 1 , L 2 , and L a are each independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group , A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arylene amine group, a substituted or unsubstituted C1 to C30 alkoxysylene group, a substituted or unsubstituted C1 to C30 aryloxylene group , A substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,

R 1 to R 4 and R a are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 hetaryl group , A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, A substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C A substituted or unsubstituted C1 to C30 acyloxy group, a substituted or unsubstituted C1 to C30 acylamino group, a substituted or unsubstituted C1 to C30 sulfonyl group, a substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 aryl A thiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

The compounds according to one embodiment of the present invention may be for organic optoelectronic devices.

Another embodiment of the present invention provides an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer includes the compound.

In another embodiment of the present invention, there is provided a display device including the above-described organic optoelectronic device.

A high-efficiency, long-life organic optoelectronic device can be realized.

1 and 2 are cross-sectional views illustrating various embodiments of an organic light emitting diode according to an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, at least one of the substituents or at least one hydrogen in the compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, C1 to C10 alkyl groups such as a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, A trifluoroalkyl group or a cyano group.

Means one to three heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon unless otherwise defined .

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a " saturated alkyl group " which does not contain any double or triple bonds.

The alkyl group may be an alkyl group having from 1 to 20 carbon atoms. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group. For example, C1 to C4 alkyl groups mean that from 1 to 4 carbon atoms are included in the alkyl chain and include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec- Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, And the like.

The term " aryl group " used herein means a substituent in which all the elements of the cyclic substituent have p-orbital and the p-orbital forms a conjugation, and the monocyclic or fused-ring polycyclic (I. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

As used herein, the term " heteroaryl group " means that the aryl group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heteroaryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted aryl group, a substituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group , A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzothiazyl groups, substituted or unsubstituted acridinyl groups, Substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups , Combinations thereof, or combinations thereof, but are not limited thereto.

In the present specification, a single bond means a bond directly connected to a carbon atom or a hetero atom other than carbon. Specifically, L means a single bond, meaning that the substituent connected to L is directly connected to the center core do. That is, in the present specification, a single bond does not mean methylene or the like via carbon.

In the present specification, the hole property refers to a property of forming holes by donating electrons when an electric field is applied, and has a conduction property along the HOMO level so that the injection of holes formed in the anode into the light emitting layer, Quot; refers to the property of facilitating the movement of the hole formed in the light emitting layer to the anode and the movement of the hole in the light emitting layer.

In addition, the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied. The electron characteristic has a conduction characteristic along the LUMO level to inject electrons formed in the cathode into the light emitting layer, move electrons formed in the light emitting layer to the cathode, It is a characteristic that facilitates movement.

The compounds according to one embodiment are described below.

In one embodiment of the present invention, a compound represented by the following general formula (1) can be provided.

[Chemical Formula 1]

Figure 112015035381976-pat00002

In Formula 1,

X 1 to X 4 are each independently N, C, CH, or CL a -R a ,

At least one of X 1 to X 4 is N,

L 1 , L 2 , and L a are each independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group , A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C6 to C30 arylene amine group, a substituted or unsubstituted C1 to C30 alkoxysylene group, a substituted or unsubstituted C1 to C30 aryloxylene group , A substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,

R 1 to R 4 and R a are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 hetaryl group , A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, A substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C A substituted or unsubstituted C1 to C30 acyloxy group, a substituted or unsubstituted C1 to C30 acylamino group, a substituted or unsubstituted C1 to C30 sulfonyl group, a substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 aryl A thiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

The compound according to an embodiment of the present invention may include at least one N in the inner ring of the crys- scene skeleton to increase thermal stability, chemical reaction stability by oxygen and hydrogen, and radical stability,

It can be produced as a compound having relatively high electron transporting properties.

The formula (1) may be represented by, for example, the following formulas (2) to (4).

[Chemical Formula 2] < EMI ID =

Figure 112015035381976-pat00003

In the above formulas 2 to 4

X 1 to X 4 are each independently N, or CL a -R a ,

L a is a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroaryl A substituted or unsubstituted C6 to C30 arylene amine group, a substituted or unsubstituted C1 to C30 alkoxysylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C2 to C30 alkenyl group A substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,

R 3 , R 4 and R a are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 hetaryl group , A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, A substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, A substituted or unsubstituted C3 to C40 silyl group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C30 alkenyl group, A substituted or unsubstituted C1 to C30 acylamino group, a substituted or unsubstituted C1 to C30 sulfonyl group, a substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C6 to C30 arylthiol group A substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group, or a combination thereof.

Since at least two Ns included in the cryshene skeleton are located in the inner ring of the cryshen, the position of N is close to that located in the outer ring of the krysene, which results in a deeper LUMO value, You can do it smoothly.

Specifically, two of X 1 to X 4 may be N.

By controlling the number and substituents of N contained in the cryshene skeleton, it can be designed as a compound having an energy level suitable for the electron transporting layer, luminescent material, or hole transporting layer.

Accordingly, it is possible to control the high efficiency, long life, and drivability at low voltage of the organic optoelectronic device using the compound.

The formula 1 may be more specifically represented by any one of the following formulas (5) to (7).

[Chemical Formula 5] < EMI ID =

Figure 112015035381976-pat00004

In the above formulas 5 to 7,

L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, A substituted or unsubstituted C6 to C30 arylenamine group, a substituted or unsubstituted C1 to C30 alkoxysilylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C6 to C30 arylenamine group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,

R 1 to R 4 each independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetaryl group, a substituted or unsubstituted C6 to C30 aryl group, C30 arylamine group, or a combination thereof.

C in the klycene skeleton adjacent to N is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetaryl group, a substituted or unsubstituted C1 to C30 alkyl group, And an unsubstituted C6 to C30 arylamine group, the thermal stability, the chemical reaction stability by oxygen and hydrogen, and the radical stability can be further increased.

Specifically, each of R 1 to R 4 and R a is independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted A substituted or unsubstituted naphthalene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted fluoranthene group, A substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted dibenzothiophenyl group, A substituted or unsubstituted pyrazine group, a substituted quinazoline group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a combination thereof.

More specifically, R 1 to R 4 , and R a may each independently be selected from hydrogen, deuterium, or a substituted or unsubstituted group listed in Group I below.

[Group I]

Figure 112015035381976-pat00005

Figure 112015035381976-pat00006

In the group I,

W is O, S or NR "

R, R 'and R "are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A combination thereof,

* Is the connection point.

Each of R 1 , R 2 and R a in the above Chemical Formulas 1 to 7 is independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 aryl group, C30 hetaryl group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof.

In one embodiment of the present invention, each of R 1 and R 2 in the general formulas (1) and (5) to (7) independently represents a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, Or an unsubstituted C2 to C30 hetaryl group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof.

In one embodiment of the present invention, R 1 and R 2 in the general formulas (1), (5) to (7) may all be substituted or unsubstituted C6 to C30 aryl groups.

In one embodiment of the present invention, any one of R 1 and R 2 in the formulas (1), (5) to (7) is a substituted or unsubstituted C6 to C30 aryl group and the other is a substituted or unsubstituted C2- C30 hetaryl group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof.

L 1 , L 2 , and L a each independently represent a hydrogen atom, May be a single bond or a substituted or unsubstituted C6 to C30 aryl group, specifically, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, and the like.

Most particularly a single bond, or a substituted or unsubstituted group listed in Group II below.

[Group II]

Figure 112015035381976-pat00007

In the group II,

* Is the connection point.

Such compounds may be, for example, compounds listed below, but are not limited thereto.

Figure 112015035381976-pat00008

Figure 112015035381976-pat00009

Figure 112015035381976-pat00010

Figure 112015035381976-pat00011

Figure 112015035381976-pat00012

Figure 112015035381976-pat00013

Figure 112015035381976-pat00014

Figure 112015035381976-pat00015

Figure 112015035381976-pat00016

Figure 112015035381976-pat00017

Figure 112015035381976-pat00018

Figure 112015035381976-pat00019

Figure 112015035381976-pat00020

Figure 112015035381976-pat00021

Figure 112015035381976-pat00022

Figure 112015035381976-pat00023

Figure 112015035381976-pat00024

The above-described compounds may be used for organic optoelectronic devices.

Hereinafter, an organic optoelectronic device to which the above-described compound is applied will be described.

In another embodiment of the present invention, there is provided an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the above-described compound .

The organic layer includes a light emitting layer, and the light emitting layer may include a compound of the present invention.

Specifically, the compound may be included as a host of the light emitting layer.

Further, in one embodiment of the present invention, the organic layer includes at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer, May be an organic optoelectronic device including the above compound.

The organic optoelectronic device is not particularly limited as long as it is an element capable of converting electric energy and optical energy. Examples of the organic optoelectronic device include organic light emitting devices, organic solar cells, and organic photoconductor drums.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 and 2 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

1, an organic optoelectronic device 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110 .

The anode 120 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

The cathode 110 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca.

The organic layer 105 includes the light emitting layer 130 including the above-described compound.

The light-emitting layer 130 may include, for example, the above-described compounds alone or may be a mixture of at least two of the above-described compounds, or may include a mixture of the above-described compounds and other compounds. When the above-mentioned compound is mixed with another compound, it may be contained in the form of, for example, a host and a dopant, and the above-mentioned compound may be included, for example, as a host. The host may be, for example, a phosphorescent host or a fluorescent host, for example, a phosphorescent host.

When the above-mentioned compound is included as a host, the dopant may be an inorganic, organic, or organic compound and may be selected from among known dopants.

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole assist layer 140 in addition to the light emitting layer 230. The hole assist layer 140 can further enhance the hole injection and / or hole mobility between the anode 120 and the light emitting layer 230 and block the electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. The above-described compounds may be included in the light emitting layer 230 and / or the hole assist layer 140.

  The organic layer 105 of FIG. 1 or 2 may further include an electron injection layer, an electron transport layer, an auxiliary electron transport layer, a hole transport layer, an auxiliary hole transport layer, a hole injection layer, or a combination layer thereof, though not shown. The compounds of the present invention may be included in these organic layers. The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a dry deposition method such as evaporation, sputtering, plasma plating, and ion plating; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode or anode on the organic layer.

The organic light emitting device described above can be applied to an organic light emitting display.

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

Hereinafter, the starting materials and the reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI unless otherwise specified.

(Preparation of compound)

Synthetic example  1: Synthesis of intermediate L-1

<Reaction Scheme 1>

Figure 112015035381976-pat00025

50.0 g (188.77 mmol) of the starting material 2-chloro-4,6-diphenyl-1,3,5-triazine, 71.14 g (280.15 mmol) of bis (pinacolato) diboron, 54.99 g (560.31 mmol) 9.15 g (11.21 mmol) of Pd (dppf) Cl 2 , 12.57 g (44.82 mmol) of tricyclohexylphosphine and 650 ml of dimethylformamide were heated and refluxed under a nitrogen stream for 12 hours. The resulting mixture was added to 1500 mL of methanol, and the crystallized solid was filtered, and the filtrate was washed with dichloromethane silica gel / celite. An organic solvent was removed in an appropriate amount and then recrystallized with a nucleic acid to obtain Compound L-7 (53.60 g 80% Yield).

calcd. C 21 H 22 BN 3 O 2 : C, 70.21; H, 6.17; B, 3.01; N, 11.70; O, 8.91; Found: C, 70.11; H, 6.18; B, 3.02; N, 11.76; 0, 8.99;

Synthetic example  2: Intermediate L- 2 of  synthesis

<Reaction Scheme 2>

Figure 112015035381976-pat00026

Intermediate 1000ml flask L-1 30.0g (83.51mmol), 1-bromo-3-iodebenzene 28.35g (100.21mmol), potassium carbonate 23.08g (167.02mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphosphine) palladium ( 0) (4.83 g, 4.18 mmol) were dissolved in 350 mL of tetrahydrofuran and 100 mL of water, and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to 1500 mL of methanol, and the crystallized solid was filtered. The filtrate was washed with dichloromethane silica gel / celite, and the organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain a compound L-2 (37.3 g 83% Yield).

calcd. C 21 H 14 BrN 3: C , 64.96; H, 3.63; Br, 20.58; N, 10.82; Found: C, 64.91; H, 3.58; Br, 20.63; N, 10.80;

Synthetic example  3: Synthesis of intermediate L-3

<Reaction Scheme 3>

Figure 112015035381976-pat00027

30.0g (77.27mmol) Intermediate L-2 to 1000ml flask, Bis (pinacolato) diboron 29.43.g ( 115.90mmol), potassium acetate 22.75g (231.80mmol), Pd (dppf ) Cl 2 3.15g (3.86mmol) toluene , And the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to 1500 mL of methanol, and the crystallized solid was filtered, and then dichloromethane-soluble silica gel / celite was filtered. The organic solvent was removed in an appropriate amount and then recrystallized with a nucleic acid to obtain Compound L-3 % Yield).

calcd. C 27 H 26 BN 3 O 2 : C, 74.49; H, 6.02; B, 2.48; N, 9.65; O, 7.35; Found: C, 74.42; H, 6.12; B, 2.40; N, 9.58; O, 7.41;

Synthetic example  4: Synthesis of intermediate L-4

Except that 2-chloro-4-phenylquinazoline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine as a starting material in Synthesis Example 1, Intermediate L-4 was synthesized by the same method as synthesis of L-1, L-2, and L-3. (Using three basic reactions: Suzuki reaction, Br bore reaction, Cl bore reaction)

<Reaction Scheme 4>

Figure 112015035381976-pat00028

Core -A synthesis process

Figure 112015035381976-pat00029

Synthetic example  5: Intermediate core -A- 01's  synthesis

<Reaction Scheme 5>

Figure 112015035381976-pat00030

10.0 g (67.92 mmol) of phthalimide, 9.05 g (67.92 mmol) of 1-isoindolinone, 34 ml of hydrochloric acid, 204 ml of acetic acid and 100 ml of water were added to a 500 ml flask and heated under reflux for 3 hours under a nitrogen stream. The resulting mixture was extracted with water and dichloromethane, and the solvent was removed. The compound core-A-01 (yield: 14.07 g, 84%) was obtained through dichloromethane and hexane column purification.

calcd. C 16 H 10 N 2 O 2 : C, 73.27; H, 3.84; N, 10.68; O, 12.20; Found: C, 73.25; H, 3.82; N, 10.69; O, 12.21;

Synthetic example  6: Intermediate core -A- 02  synthesis

<Reaction Scheme 6>

Figure 112015035381976-pat00031

10.0 g (38.13 mmol) of intermediate coer-A-01, 0.12 g (1.91 mmol) of Zinc, 210 ml of acetic acid and 100 ml of water were placed in a 500 ml flask and reacted at room temperature for 12 hours under a nitrogen stream. The resulting mixture was extracted with water and dichloromethane, the solvent was removed, and the compound core-A-02 (yield 92%) was obtained through dichloromethane and hexane column purification.

calcd. C 16 H 12 N 2 O 2 : C, 72.72; H, 4.58; N, 10.60; O, 12.11; found: C, 72.73; H, 4.56; N, 10.61; 0, 12.13;

Synthetic example  7: Intermediate core -A- 03 of  synthesis

<Reaction Scheme 7>

Figure 112015035381976-pat00032

10.0 g (37.84 mmol) of the intermediate coer-A-02, 40 ml of hydrochloric acid and 120 ml of water were added to a 500 ml flask, and the mixture was heated under reflux in a nitrogen stream for 12 hours. The resulting mixture was extracted with water and dichloromethane, the solvent was removed, and the compound core-A-03 (9.52 g, 95% yield) was obtained through dichloromethane and hexane column purification.

calcd. C 16 H 12 N 2 O 2 : C, 72.72; H, 4.58; N, 10.60; O, 12.11; found: C, 72.76; H, 4.57; N, 10.61; O, 12.11;

Synthetic example  8: Intermediate core -A- 04's  synthesis

<Reaction Scheme 8>

Figure 112015035381976-pat00033

A 500 ml flask was charged with 10.0 g (37.84 mmol) of the intermediate coer-A-03, 25.77 g (113.52 mmol) of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 150 ml of 1,4- , And the mixture was heated under reflux in a nitrogen stream for 12 hours. The obtained mixture was extracted with water and dichloromethane, and the solvent was removed. The compound core-A-04 (yield of 6.95 g 70%) was obtained through dichloromethane and hexane column purification.

calcd. C 16 H 10 N 2 O 2 : C, 73.27; H, 3.84; N, 10.68; O, 12.20; Found: C, 73.21; H, 3.81; N, 10.68; O, 12.22;

Synthetic example  9: Intermediate core -A- 05's  synthesis

<Reaction Scheme 9>

Figure 112015035381976-pat00034

10.0 g (38.13 mmol) of the intermediate coer-A-04 and 31.89 ml (343.17 mmol) of phosphoryl chloride were added to a 500 ml flask, and the mixture was refluxed under heating in a nitrogen stream for 12 hours. After completion of the reaction, the solid was removed through a filter, and the filtrate was returned with ice to give a solid. The resulting solid was subjected to filtration to obtain a compound core-A-05 (yield of 9.48 g 83%).

calcd. C 16 H 8 Cl 2 N 2 : C, 64.24; H, 2.70; Cl, 23.70; N, 9.36; Found: C, 64.25; H, 2.71; Cl, 23.72; N, 9.34;

Synthetic example  10: Intermediate core Synthesis of -A-06

<Reaction formula 10>

Figure 112015035381976-pat00035

Intermediate coer-A-05 10.0g to 1000ml flask (39.20mmol), Phenylboronic acid 5.82g ( 37.24mmol), potassium carbonate 10.83g (78.39mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphosphine)? Palladium (0) ) Were placed in 100 mL of tetrahydrofuran and 40 mL of water, and the mixture was heated under reflux for 10 hours under a nitrogen stream. The resulting mixture was added to 300 mL of methanol, and the crystallized solid was filtered, and the resulting product was purified by dichloromethane and hexane to obtain a compound core-A-06 (yield of 6.31 g 47%).

calcd. C 22 H 13 ClN 2: C , 77.53; H, 3.84; Cl, 10.40; N, 8.22; Found: C, 77.51; H, 3.82; Cl, 10.41; N, 8.23

Synthetic example  11: Synthesis of A-8

<Reaction Scheme 11>

Figure 112015035381976-pat00036

10.0 g (29.34 mmol) of the intermediate coer-A-06, 12.58 g (30.81 mmol) of L-4, 8.11 g (58.68 mmol) of potassium carbonate and Pd (PPh 3 ) 4 (Tetrakis (triphenylphos phine) palladium ) (1.70 g, 1.47 mmol) were dissolved in tetrahydrofuran (80 mL) and water (30 mL), and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to methanol (300 mL), and the crystallized solid was filtered. Dichloromethane was dissolved in silica gel / celite, and the organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain 13.87 g of 77% Yield).

calcd. C 42 H 26 N 4 : C, 85.98; H, 4.47; N, 9.55; found: C, 85.95; H, 4.46; N, 9.52;

Synthetic example  12: Synthesis of A-64

<Reaction Scheme 12>

Figure 112015035381976-pat00037

Intermediate coer-A-06 10.0g to 1000ml flask (29.34mmol), L-3 13.41g (30.81mmol), potassium carbonate 8.11g (58.68mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphos phine) palladium (0 ) (1.70 g, 1.47 mmol) were dissolved in tetrahydrofuran (80 mL) and water (30 mL), and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to methanol (300 mL), and the crystallized solid was filtered. The filtrate was washed with dichloromethane silica gel / celite, and an organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain Compound A-64 (12.64 g 70% Yield).

calcd. C 43 H 27 N 5 : C, 84.15; H, 4.43; N, 11.41; Found: C, 84.11; H, 4.42; N, 11.43;

Core -B synthesis process

Core-A-02, core-A-03, core-A-04, and core-A-01 of the above-mentioned synthetic examples 5, 6, 7, 8, 9 and 10 as a more specific example of the compound of the present invention 2,3-dione was used in place of Phthalimide, which is the first starting intermediate in A-05, core-A-06, and 1-indolin-2-one was used in place of Isoindolinone. Core-B-01 &lt; / RTI &gt;

Figure 112015035381976-pat00038

Synthetic example  13: Synthesis of B-8

<Reaction Scheme 13>

Figure 112015035381976-pat00039

Intermediate 1000ml flask coer-B-01 10.0g (29.34mmol ), L-4 12.58g (30.81mmol), potassium carbonate 8.11g (58.68mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphos phine) palladium (0 ) (1.70 g, 1.47 mmol) were dissolved in tetrahydrofuran (80 mL) and water (30 mL), and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to methanol (300 mL), and the crystallized solid was filtered. Dichloromethane was dissolved in silica gel / celite. The organic solvent was removed in an appropriate amount, and the residue was recrystallized from methanol to obtain Compound B- Yield).

calcd. C 42 H 26 N 4 : C, 85.98; H, 4.47; N, 9.55; found: C, 85.97; H, 4.48; N, 9.56;

Synthetic example  14: Synthesis of B-64

<Reaction Scheme 14>

Figure 112015035381976-pat00040

Intermediate 1000ml flask coer-B-01 10.0g (29.34mmol ), L-3 13.41g (30.81mmol), potassium carbonate 8.11g (58.68mmol), Pd (PPh 3) 4 (Tetrakis (triphenylphos phine) palladium (0 ) (1.70 g, 1.47 mmol) were dissolved in tetrahydrofuran (80 mL) and water (30 mL), and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resulting mixture was added to methanol (300 mL), and the crystallized solid was filtered. The filtrate was washed with dichloromethane and silica gel / celite. An organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain Compound B-64 (13.21 g 73% Yield).

calcd. C 43 H 27 N 5 : C, 84.15; H, 4.43; N, 11.41; Found: C, 84.13; H, 4.41; N, 11.45;

Comparative Synthetic Example

The simulation characteristics were calculated for the compounds of the following structures and are shown in Table 1 below.

[Compound a] [Compound b]

Figure 112015035381976-pat00041
,
Figure 112015035381976-pat00042

[Compound c] [Compound d] [Compound e]

Figure 112015035381976-pat00043

(Comparison of simulation characteristics of prepared compounds)

The energy level of each material was calculated by the Gaussian 09 method using a super computer GAIA (IBM power 6), and the results are shown in Table 1 below.

compound HOMO (eV) LUMO (eV) T1 (eV) S1 (eV) A-8 -5.559 -1.926 2.380 3.270 A-64 -5.653 -1.887 2.383 3.349 B-8 -5.863 -1.929 2.450 3.406 B-64 -5.980 -2.014 2.443 3.409 a -5.53 -1.95 2.256 3.125 b -5.588 -2.213 2.225 2.957 c -5.352 -1.698 2.336 3.207 d -5.663 -1.688 2.492 3.471 e -5.481 -1.743 2.343 3.296

As can be seen from Table 1,

It is expected that the desired LUMO energy level on the simulation is good for electron transport characteristics when -1.8 to -2.1 eV and for 2.3 to 2.5 eV for Red Host T1. It can be seen that the compounds A-8, A-64, B-8 and B-64 have a LUMO value with good electron transport properties because the amine is located in the center of the chrysene, Good efficiency can be obtained. On the other hand, in the case of the comparative synthesis example compounds b, c, d, and e, the amine is located on the outer side of the klycene, and the LUMO value is too high or low. In the case of the comparative synthesis example compound a, since the T1 energy level is lower than 2.3 eV, it is difficult to expect a good efficiency.

(Fabrication of organic light emitting device)

Example  One

An organic light emitting device was fabricated using A-8 obtained in Synthesis Example 10 as a host and (piq) 2 Ir (acac) as a dopant.

As the anode, ITO was used in a thickness of 1000 Å, and aluminum (Al) was used in a thickness of 1000 Å as a cathode. The ITO glass substrate having a sheet resistance of 15 Ω / cm 2 is cut into a size of 50 mm × 50 mm × 0.7 mm, and is coated with acetone, isopropyl alcohol, and pure water in an amount of 15 Min for 30 minutes, and then rinsed with UV ozone for 30 minutes.

N4, N4'-di (naphthalene-1-yl) -N4, N4'-diphenylbiphenyl-4,4'-diaminodiphenylsulfonate was deposited on the substrate at a degree of vacuum of 650 × 10-7 Pa and a deposition rate of 0.1 to 0.3 nm / - diamine (N4, N4'-di (naphthalene-1-yl) -N4, N4'-diphenylbiphenyl-4,4'-diamine: NPB) (80 nm) was deposited thereon to form a 800Å hole transport layer. Then, using the A-8 in Synthesis Example 10 under the same vacuum deposition conditions, the film was formed in a thickness of 300Å light-emitting layer, at this time, and depositing the phosphorescent dopant (piq) 2 Ir (acac) at the same time.

At this time, the deposition rate of the phosphorescent dopant was adjusted so that the total amount of the light emitting layer was 100 wt%, and the phosphorescent dopant content was 3 wt%.

(2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (bis (2-methyl-8- quinolinolato) aluminum: BAlq) was deposited thereon to form a 50 Å hole blocking layer. Subsequently, Alq3 was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 200 ANGSTROM. LiF and Al were sequentially deposited on the electron transport layer as cathodes to fabricate an organic optoelectronic device.

The structure of the organic optoelectronic device was ITO / NPB (80 nm) / EML (A-132 (97 wt%) + (piq) 2 Ir (acac) (3 wt%), 30 nm) / Balq 20 nm) / LiF (1 nm) / Al (100 nm).

Example  2

An organic luminescent device was prepared in the same manner as in Example 1 except that A-64 of Synthesis Example 11 was used instead of the compound A-8 of Example 1.

Example  3

An organic luminescent device was prepared in the same manner as in Example 1, except that B-8 in Synthesis Example 12 was used instead of Compound A-8 in Example 1.

Example  4

An organic luminescent device was prepared in the same manner as in Example 1 except that B-64 of Synthesis Example 13 was used instead of the compound A-8 of Example 1.

Comparative Example  One

An organic luminescent device was prepared in the same manner as in Example 1 except that CBP was used in place of the compound A-8 of Example 1.

The structures of NPB, BAlq, CBP and Ir (PPy) 3 used in the above organic light emitting device are as follows.

Figure 112015035381976-pat00044

(Performance Measurement of Organic Light Emitting Device)

Examples 1, 2, 3, and 4, and Comparative Example 1 were measured for current density change, luminance change, and luminous efficiency according to the voltage of the organic light emitting device.

The specific measurement method is as follows, and the results are shown in Table 2.

(1) Measurement of change in current density with voltage change

For the organic light emitting device manufactured, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change

For the organic light-emitting device manufactured, luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the result was obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

(4) Life measurement

The time at which the luminance (cd / m 2 ) was maintained at 5000 cd / m 2 and the current efficiency (cd / A) decreased to 90% was measured and the results were obtained.

No. The light- The driving voltage (V) color
(EL color) efficiency
(cd / A) 90% lifetime (h)
At 5000 cd / m 2 Example 1 A-8 5.3 Red 12.9 74 Example 2 A-64 5.0 Red 12.4 61 Example 3 B-8 5.4 Red 13.1 76 Example 4 B-64 5.2 Red 12.3 63 Comparative Example 1 CBP 6.5 Red 5.5 20

As can be seen from the above Table 2, the improved characteristics in terms of driving voltage, luminous efficiency and / or power efficiency are shown as compared with Comparative Example 1. [

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100: organic light emitting device 200: organic light emitting device
105: organic layer
110: cathode
120: anode
130: light emitting layer 230: light emitting layer
140: hole assist layer

Claims (15)

delete delete delete A compound represented by the following formula (5) or (6):
[Chemical Formula 5]
Figure 112018088848919-pat00072
Figure 112018088848919-pat00073

In the above formulas (5) and (6)
L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, A substituted or unsubstituted C6 to C30 arylenamine group, a substituted or unsubstituted C1 to C30 alkoxysilylene group, a substituted or unsubstituted C1 to C30 aryloxylene group, a substituted or unsubstituted C6 to C30 arylenamine group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,
R 1 and R 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetaryl group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof ,
R 3 and R 4 each independently represent a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 hetaryl group, a substituted or unsubstituted C6 to C30 aryl group, C30 arylamine group, or a combination thereof. delete 5. The method of claim 4,
Any one of R 1 and R 2 is a substituted or unsubstituted C6 to C30 aryl group,
And the other is a substituted or unsubstituted C2 to C30 hetaryl group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof. 5. The method of claim 4,
Each of R 1 and R 2 is independently a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, Substituted or unsubstituted naphthalene groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted triphenylene groups, substituted or unsubstituted parenthrene groups, substituted or unsubstituted fluoranshenes, substituted or unsubstituted carbazole groups, substituted or unsubstituted A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzimidazole group, A pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a combination thereof,
R 3 and R 4 are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, A substituted or unsubstituted naphthalene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pendantrene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group , Substituted or unsubstituted fluorene groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted benzimidazole groups, substituted or unsubstituted quinazoline groups, substituted Or an unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a combination thereof. 5. The method of claim 4,
Each of R 1 and R 2 is independently selected from a substituted or unsubstituted group listed in the following Group I,
Wherein R 3 and R 4 are each independently selected from hydrogen, deuterium, or a substituted or unsubstituted group listed in Group I below:
[Group I]
Figure 112018088848919-pat00048

In the group I,
W is O, S or NR "
R, R 'and R "are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A combination thereof,
Figure 112018088848919-pat00074
, R and R 'are each independently a substituted or unsubstituted C6 to C30 aryl group,
* Is the connection point. 5. The method of claim 4,
Each of L 1 and L 2 is, independently of each other, A single bond, or a substituted or unsubstituted group listed in Group II:
[Group II]
Figure 112018088848919-pat00049

In the group II,
* Is the connection point. 5. The method of claim 4,
Is a compound selected from the compounds listed below:
Figure 112018088848919-pat00050

Figure 112018088848919-pat00051

Figure 112018088848919-pat00052

Figure 112018088848919-pat00053

Figure 112018088848919-pat00054

Figure 112018088848919-pat00055

Figure 112018088848919-pat00056

Figure 112018088848919-pat00057

Figure 112018088848919-pat00058
. 10. Compounds according to any one of claims 4 and 6 to 10 for use in organic optoelectronic devices. An anode and a cathode facing each other, and
And at least one organic layer positioned between the anode and the cathode,
Wherein the organic layer comprises the compound according to any one of claims 4 and 6 to 10. 13. The method of claim 12,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound. 14. The method of claim 13,
Wherein the compound is included as a host of the light emitting layer. 13. The method of claim 12,
Wherein the organic layer includes at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer,
Wherein the auxiliary layer comprises the compound.
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