KR101986261B1

KR101986261B1 - Compound FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE

Info

Publication number: KR101986261B1
Application number: KR1020150175998A
Authority: KR
Inventors: 김병구; 장춘근; 김영권; 원종우; 유은선; 정성현; 정주연
Original assignee: 삼성에스디아이 주식회사
Priority date: 2015-12-10
Filing date: 2015-12-10
Publication date: 2019-06-05
Also published as: KR20170068927A

Abstract

A compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device including the same, and a composition for the organic optoelectronic device or a composition for an organic optoelectronic device, and a display device including the organic optoelectronic device .
Details of the above formula (1) are described in the specification.

Description

Technical Field [0001] The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, and an organic optoelectronic device and a display device including the same. BACKGROUND ART [0002]

Compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices and display devices.

An organic optoelectronic device is an element capable of converting electrical energy to 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.

One embodiment provides a compound for an organic optoelectronic device capable of implementing a high-efficiency and long-lived organic optoelectronic device.

Another embodiment provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device.

Another embodiment provides a display device comprising the organic opto-electronic device.

According to one embodiment, there is provided a compound for an organic optoelectronic device represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X is O or S,

Wherein ^{one of} R ¹ and R ² is a substituted or unsubstituted N-containing C2 to C30 heterocyclic group and the other is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, An unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkylsilyl group, a C6 to C20 arylamine group or a cyano group,

R ³ to R ⁶ each independently represent hydrogen, deuterium, a halogen group, a hydroxyl group, a substituted or unsubstituted C1 to C40 silyl group, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a C1 to C20 alkoxy group , A substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C30 arylthio group, A substituted C2-C30 heterocyclic group, or a combination thereof,

L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

The term "substituted" as used herein means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, 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 C2 to C30 heterocycloalkyl group, To C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.

According to another embodiment, the aforementioned compound for an organic optoelectronic device; And a compound represented by the following general formula (2).

(2)

In Formula 2,

Each of L ¹ to L ³ , Y ¹ , and Y ⁴ is independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof ,

Ar ¹ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ⁹ to R ¹¹ , and R ¹⁷ to R ¹⁹ are A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof,

m is an integer of 0 to 4;

In another embodiment, the organic light emitting device includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer includes the compound for the organic optoelectronic device or the organic optoelectronic device And an organic electroluminescent device.

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

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, " substituted " means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, halogen, hydroxyl, C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C3 to C30 cycloalkyl, Means a group substituted with a cycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.

A substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 An aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group may be fused to form a ring. For example, the substituted C6 to C30 aryl group may be fused with another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.

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, the term "alkyl group" means an aliphatic hydrocarbon group, unless otherwise defined. 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 of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 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.

As used herein, the term " aryl group " is intended to encompass groups having one or more hydrocarbon aromatic moieties, in which all the elements of the hydrocarbon aromatic moiety have a p-orbital, Such as a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, which include two or more hydrocarbon aromatic moieties including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, May also include non-aromatic fused rings fused directly or indirectly. For example, a fluorenyl group and the like.

The aryl groups include monocyclic, polycyclic or fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups. For example, the aryl group means a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group, and the like.

As used herein, the term " heterocyclic group " is a superordinate concept including a heteroaryl group, and includes N, O, and S substituents in the ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Means at least one heteroatom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.

As used herein, the term " heteroaryl group " means that at least one heteroatom selected from the group consisting of N, O, S, P and Si is contained in the aryl group instead of carbon (C). Two or more heteroaryl groups may be directly connected through a sigma bond, or when the C2 to C60 heteroaryl group includes two or more rings, two or more rings may be fused with each other. 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 heterocyclic group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, 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 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 triazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group , A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, Substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted naphthyridinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzthiazinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinoxalinyl groups, A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group , A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzothiophene pyrimidinyl group, a substituted or unsubstituted benzothiophene pyridinyl group, a substituted or unsubstituted benzofuran Substituted or unsubstituted benzothiophenylacetyl groups, substituted or unsubstituted benzothiophenethylacetyl groups, substituted or unsubstituted benzothiophenethylacetyl groups, substituted or unsubstituted benzothiophenylacetyl groups, A substituted or unsubstituted thiazoloquinolinyl group, a substituted or unsubstituted oxazolinoquinolinyl group, or a combination thereof, but is 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 so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer migrate to the cathode, It is a characteristic that facilitates movement.

The compounds for organic optoelectronic devices according to one embodiment will be described below.

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

[Chemical Formula 1]

In Formula 1,

X is O or S,

The compound for organic optoelectronic devices represented by Formula 1 is a C2 to C30 heterocyclic group containing N in the pyrimidine moiety of benzofuranpyrimidine core or benzothiophenepyrimidine core; And a structure which simultaneously contains a C1 to C20 alkyl group, a C1 to C20 alkoxy group, a C3 to C30 cycloalkyl group, a C1 to C20 alkylsilyl group, a C6 to C20 arylamine group or a cyano group.

In the case of the compound represented by the above formula (1), the ET moiety in the benzofuranpyrimidine core or the benzothiophene pyrimidine core, that is, the N-containing C2 to C30 heterocyclic group, is included to increase the mobility of holes and electrons, , While at the same time minimizing the interaction between molecules due to the structural steric hindrance of the compound, it is possible to inhibit the crystallization of the compound.

In addition, in the case of the compound represented by the formula (1), it is possible to form a three-dimensional molecular structure by another substituent (R ¹ or R ² ) in addition to the ET moiety and thus to form a random or amorphous molecular arrangement. The deposition temperature may be lowered. Accordingly, the production yield of the organic EL device including the compound can be improved, and the lifetime can be improved.

In addition, by having such a random or amorphous molecular array, the HOMO and LUMO energy levels of the compound can be effectively controlled, and thus the hole and electron balance can be well balanced, thereby realizing an organic EL device with low driving, high efficiency and long life .

In addition, since the compound represented by Formula 1 has good solubility, it is possible to perform a solution process in addition to the deposition process, thereby simplifying the process.

According to one embodiment of the present invention, any one of R ¹ and R ² in the above formula (1) is an N-containing C2 to C30 heterocyclic group such as a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, A substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, Or a substituted or unsubstituted indazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted quinolinyl group, Phthal A substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted sienolinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted isobenzothiazolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenanthrolinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted isobenzoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiazolyl group, A substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted imidazopyridinyl group, or a substituted or unsubstituted imidazole group Substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted benzimidazolyl groups, A benzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuran-pyridinyl group, a substituted or unsubstituted benzofuran-pyrimidinyl group, a substituted or unsubstituted benzothiophenylpyridinyl group, or a A substituted or unsubstituted benzothiophenepyrimidinyl group,

And the other is a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxy group, an ethoxy group, a trimethylsilyl group, a diphenylamine group, a cyano group, a substituted or unsubstituted cyclopentyl group, or a substituted or unsubstituted cyclohexyl group Lt; / RTI >

More specifically, the N-containing C2 to C30 heterocyclic group is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, Substituted or unsubstituted benzothiazolyl groups, substituted or unsubstituted benzoxazolyl groups, substituted or unsubstituted benzoquinazolinyl groups, substituted or unsubstituted benzoquinazolinyl groups, substituted or unsubstituted benzothiazolyl groups, substituted or unsubstituted benzoxazolyl groups, A substituted or unsubstituted benzofuranylpiperidinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyridinyl group, or a substituted or unsubstituted benzofuranylpyridazinyl group, Unsubstituted benzothiophene can pyrimidinyl group.

As the most specific example, the N-containing C2 to C30 heterocyclic group may be a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

The N-containing C2 to C30 heterocyclic group may be represented by the following formula (I-I) or (II-II) depending on the substitution position.

[Chemical Formula 1-I] [Chemical Formula 1-II]

In the above general formulas (I-1) and (II-II)

X, R ¹ to R ⁶ , L ¹ and L ² are as defined above,

Z is each independently N or CR ^a , at least one of Z is N,

R ⁷ , R ⁸ , and R ^a have the same definitions as R ¹ to R ⁶ .

In one embodiment of the present invention, each of R ³ to R ⁸ is independently hydrogen, deuterium, a halogen group, a hydroxyl group, a substituted or unsubstituted C1 to C40 silyl group, a cyano group, a substituted or unsubstituted C1 A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, To C30 arylthio groups, substituted or unsubstituted C2 to C30 heterocyclic groups, or combinations thereof.

Specifically, R ⁷ and R ⁸ are a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C6 to C30 aryl group, C30 arylthio group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

More specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenan A thienyl group, a substituted or unsubstituted triphenylene group, or a combination thereof.

Specifically, R ³ to R ⁶ are independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a substituted or unsubstituted C1- C20 alkoxy group, a substituted or unsubstituted C1 to C40 silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluoro group, A substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group,

More specifically, it is preferable to use at least one of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, And may be, for example, all hydrogen, but is not limited thereto.

In one embodiment of the present invention, L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, .

Specifically, L ¹ and L ² may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quaterphenylene group, A substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, A substituted or unsubstituted pyrimidinylene group, or a substituted or unsubstituted triazinylene group,

More specifically, it may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quaterphenylene group, or a substituted or unsubstituted naphthylene group , But is not limited thereto.

In one embodiment of the present invention, Formula 1 may be represented by Formula 1-II, wherein X may be O or S, and R ¹ may be a substituted or unsubstituted C1 to C20 An alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkylsilyl group, a C6 to C20 arylamine group or a cyano group, Z are independently N or CR ^a, and at least one Z may be a N, R ³ to R ^8, and R ^a are each independently hydrogen, deuterium, a halogen group, a hydroxyl group, a substituted or unsubstituted A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 silyl group, a substituted or unsubstituted C1 to C10 alkyl group, a C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, An unsubstituted C6 to C30 aryloxy group, Substituted C6 to C30 arylthio group, may be substituted or unsubstituted C2 to C30 heterocyclic group, or combinations thereof, L ¹ may be a single bond, L ² is a single bond, unsubstituted C6 substituted or unsubstituted To C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

The compound for the first organic optoelectronic device represented by Formula 1 may be selected from compounds listed in the following Group A, but is not limited thereto.

[Group A]

The above-described compounds for organic optoelectronic devices can be applied to organic optoelectronic devices and can be applied to organic optoelectronic devices either alone or in combination with other compounds for organic optoelectronic devices. When the above-mentioned compound for an organic optoelectronic device is used together with another compound for an organic optoelectronic device, it can be applied in the form of a composition.

Hereinafter, an example of the composition for an organic optoelectronic device including the aforementioned compound for an organic optoelectronic device will be described.

In another embodiment of the present invention, the aforementioned compound for an organic optoelectronic device (hereinafter referred to as " first compound "); And a compound represented by the following general formula (2) (hereinafter referred to as " second compound ").

(2)

In Formula 2,

L ¹ to L ³ , Y ¹ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group,

Ar ¹ and Ar ⁴ are a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ⁹ to R ¹¹ and R ¹⁷ to R ¹⁹ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 hetero A cyclic group or a combination thereof,

m is an integer of 0 to 4;

Specifically, Ar ¹ and Ar ⁴ in Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothi group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothi A substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted pyridinyl group, or a combination thereof.

Specifically, Formula 2 is one of the structures listed in Group 1, and * -Y ¹ -Ar ¹ , * -Y ⁴ -Ar ⁴ may be any of the substituents listed in Group 2 below.

[Group 1] (all the heteroatoms in the moiety are "N")

c-11 c-12 c-13

c-14 c-15

[Group 2]

B-16 B-17 B-18

In the groups 1 and 2, * is a connection point.

The second compound represented by Formula 2 may be, for example, compounds listed in Groups B to D below, but is not limited thereto.

[Group B]

[B-1] [B-2] [B-3]

[B-4] [B-5] [B-6]

[B-7] [B-8] [B-9]

[B-10] [B-11] [B-12]

[B-13] [B-14] [B-15]

[B-16] [B-17] [B-18]

[B-19] [B-20] [B-21]

[B-22] [B-23] [B-24]

[B-25] [B-26] [B-27]

[B-28] [B-29] [B-30] [B-31]

[B-33] [B-34] [B-35]

[B-36] [B-37] [B-38]

[B-39] [B-40] [B-41]

[B-42] [B-43] [B-44]

[B-45] [B-46] [B-47]

[B-48] [B-49] [B-50]

[B-51] [B-52] [B-53]

[B-54] [B-55] [B-56]

[B-57] [B-58] [B-59]

[B-60] [B-61] [B-62]

[B-63] [B-64] [B-65]

[B-66] [B-67] [B-68]

[B-69] [B-70] [B-71]

[B-72] [B-73] [B-74]

[B-75] [B-76] [B-77]

[B-78] [B-79] [B-80]

[B-81] [B-82] [B-83]

[B-84] [B-85] [B-86]

[B-87] [B-88] [B-89]

[B-90] [B-91] [B-92]

[B-93] [B-94] [B-95]

[B-96] [B-97] [B-98] [B-99]

[B-101] [B-102] [B-103]

[B-104] [B-105] [B-106]

[B-107] [B-108] [B-109]

[B-110] [B-111] [B-112]

[B-113] [B-114] [B-115]

[B-116] [B-117] [B-118]

[B-119] [B-120] [B-121]

[B-122] [B-123] [B-124]

[B-125] [B-126] [B-127]

[B-128] [B-129] [B-130]

[B-131] [B-132] [B-133] [B-134]

[B-135] [B-136] [B-137] [B-138]

The second compound is a compound having a bipolar characteristic with a relatively high hole property and is used in a light emitting layer together with the first compound to improve charge transportability and stability to improve light emitting efficiency and lifetime characteristics . Further, the charge mobility can be controlled by adjusting the ratio of the second compound having hole characteristics to the first compound. Since the hole characteristic of the second compound is relatively determined in relation to the first compound, a weak electron such as a substituted or unsubstituted pyridinyl group at any one of R ⁹ to R ¹² and Ar ¹ in the general formula &Lt; / RTI >

Also, the first compound and the second compound may be contained in a weight ratio of, for example, about 1: 9 to 9: 1, specifically 2: 8 to 8: 2, 3: 7 to 7: : 4, and 5: 5 by weight. By being included in the above-mentioned range, the bipolar characteristic can be realized, and the efficiency and lifetime can be simultaneously improved.

As an example of the composition for an organic optoelectronic device, the first compound may be represented by the formula 1-I or 1-II, and the second compound may be represented by the formula 2.

As an example of the composition for an organic optoelectronic device, the first compound may be represented by the formula (I-II), and the second compound may be represented by the formula (II).

The composition may further include at least one organic compound in addition to the first compound and the second compound.

The compound for an organic optoelectronic device may further include a dopant. The dopant may be a red, green or blue dopant.

The dopant may be a material that emits light by mixing a small amount of light, and may be a material such as a metal complex that emits light by multiple excitation that excites it to a triplet state. The dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.

Examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof And the like. The phosphorescent dopant may be, for example, a compound represented by the following formula (Z), but is not limited thereto.

(Z)

L ₂ MX

In the above formula (Z), M is a metal, L and X are the same or different from each other and are ligands that complex with M.

M may be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, Lt; / RTI >

Hereinafter, the compound for an organic optoelectronic device or the organic optoelectronic device to which the composition for an organic optoelectronic device is applied will be described.

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, An organic optoelectronic device including a composition for an organic optoelectronic device can be provided.

The organic layer may include a light emitting layer, and the light emitting layer may include a compound for an organic optoelectronic device or a composition for an organic optoelectronic device of the present invention.

Specifically, the compound for an organic optoelectronic device or the composition for an organic optoelectronic device may be included as a host of the light emitting layer.

The organic layer may include at least one auxiliary layer selected from a light emitting layer and a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer and a hole blocking layer, , Or compositions for organic optoelectronic devices.

The auxiliary layer may further include an electron transporting auxiliary layer adjacent to the light emitting layer, and the electron transporting auxiliary layer may include a compound for the organic optoelectronic device or a composition for an organic optoelectronic device.

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 compound for the organic optoelectronic device described above.

2 is a cross-sectional view illustrating an organic light emitting device according to another embodiment.

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole-assist layer 140 in addition to the light-emitting layer 130. The hole auxiliary layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block 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.

1 or 2 may further include an electron injection layer, an electron transport layer, an electron transporting auxiliary layer, a hole transporting layer, a hole transporting auxiliary layer, a hole injecting layer, or a combination layer thereof have. The compound for organic optoelectronic devices of the present invention can 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 reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI unless otherwise stated, or synthesized by known methods.

(Preparation of compound for organic optoelectronic device)

The compounds shown as more specific examples of the compounds of the present invention were synthesized by the following steps.

(First compound)

Synthesis of intermediate A

[Reaction Scheme 1]

Intermediate A (1) ( Benzo -1H- Tieno [3,2-d] pyrimidine-2,4- Dion ) Synthesis of

A 2 L round bottom flask was charged with a mixture of methyl 3-amino-benzothiophene-2-carboxylate (237.5 g, 1.15 mol) and urea (397.0 g, 5.75 mol) at 200 ° C for 2 hours. The reaction mixture was cooled to room temperature, poured into sodium hydroxide solution and the impurities were removed by filtration. The reaction product was acidified (HCl, 2N) and the obtained precipitate was dried to obtain Intermediate A (1) (IA (175 g, 75%).

calcd. _{C 10 H 6 N 2 O 2} S: C, 55.04; H, 2.77; N, 12.84; 0, 14.66; S, 14.69; Found: C, 55.01; H, 2.79; N, 12.81; O, 14.69; S, 14.70

Intermediate A ( Benzo -2,4- Dichloro - Thieno [3,2-d] pyrimidine ) Synthesis of

Thieno [3,2-d] pyrimidine-2,4-dione) (175 g, 0.80 mol) and phosphorus oxychloride (1.0 g) were added to a 3000 mL round- (1000 mL) was stirred at reflux for 8 hours. The reaction mixture was cooled to room temperature and poured into ice / water with vigorous stirring to form a precipitate. The resulting reaction product was filtered to obtain Intermediate A (I-A) (benzo-2,4-dichloro-thieno [3,2-d] pyrimidine) (175 g, 85%, white solid). The result of the elemental analysis of the resulting intermediate A is as follows.

calcd. _{C 10 H 4 Cl 2 N 2} S: C, 47.08; H, 1.58; Cl, 27.79; N, 10.98; S, 12.57; found: C, 47.03; H, 1.61; Cl, 27.81; N, 10.98; S, 12.60

Synthetic example 1: Synthesis of Compound A-1

[Reaction Scheme 2]

Synthesis of Intermediate 1-2

In a 1000 mL flask, 50.0 g (128.8 mmol) of Intermediate 1-1 prepared by a known method, 22.15 g (141.66 mmol) of 3-chloro-1-phenylboronic acid, 44.6 g (321.9 mmol) of potassium carbonate, (Triphenylphosphine) palladium (0) (4.5 g, 3.9 mmol) were placed in 400 mL of 1,4-dioxane and 200 mL of water, and the mixture was heated at 65 ° C for 24 hours under a nitrogen stream. The resulting mixture was added to 1200 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount, and then recrystallized from methanol to obtain 37.9 g , 70% yield).

calcd. C27H18ClN3: C, 77.23; H, 4.32; Cl, 8.44; N, 10.01; Found: C, 77.22; H, 4.31; Cl, 8.45; N, 10.02

Synthesis of intermediate 1-3

To a 1000 mL flask was added Intermediate 1-2 (35.0 g, 83.4 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- (25.4 g, 100.0 mmol), potassium acetate (KOAc, 24.5 g, 250.7 mmol) and 1,1'-bis (diphenylphosphino) ferrocene-palladium (II) dichloride , 5.0 mmol) and tricyclohexylphosphine (7.0 g, 12.5 mmol) were added to 400 mL of N, N-dimethylformamide, followed by stirring at 140 ° C for 24 hours. After completion of the reaction, the reaction solution was extracted with water and EA. The organic layer was dried over magnesium sulfate to remove water, concentrated and purified by column chromatography to obtain Intermediate 1-3 as a white solid (32.0 g, yield = 75 %).

calcd. C33H30BN3O2: C, 77.50; H, 5.91; B, 2.11; N, 8.22; 6.26; Found: C, 77.51; H, 5.90; B, 2.11; N, 8.21; O, 6.26

Synthesis of intermediate 1-4

To a 1000 mL flask was added 20.0 g (78.4 mmol) of intermediate A, 11.0 g (86.2 mmol) of cyclohexylbromonic acid, 27.1 g (196.0 mmol) of potassium carbonate, 2.7 g of tetrakis (triphenylphosphine) palladium 2.4 mmol) was added to 160 mL of 1,4-dioxane and 130 mL of water, and the mixture was heated to 60 DEG C for 24 hours under a nitrogen stream. The resulting mixture was added to methanol (800 mL), and the crystallized solid was filtered, and the filtrate was dissolved in monochlorobenzene. The filtrate was filtered through silica gel / celite, and an organic solvent was removed in an appropriate amount, followed by recrystallization from methanol to obtain Intermediate 1-4 , 72% yield).

calcd. For C16H15ClN2S: C, 63.46; H, 4.99; Cl, 11.71; N, 9.25; S, 10.59; Found: C, 63.46; H, 4.99; Cl, 11.71; N, 9.24; S, 10.59

Synthesis of Compound A-1

To a 100 mL flask was added 3.0 g (9.9 mmol) of intermediate 1-4, 5.6 g (10.90 mmol) of intermediate 1-3, 3.4 g (24.8 mmol) of potassium carbonate, 0.34 g 0.3 mmol) was added to 32 mL of 1,4-dioxane and 16 mL of water, and the mixture was heated to 65 DEG C for 24 hours under a nitrogen stream. The resulting solid was added to methanol (100 mL), and the resulting solid was filtered. The resulting solid was dissolved in monochlorobenzene, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain Compound A- , 67% yield).

calcd. For C43H33N5S: C, 79.23; H, 5.10; N, 10.74; S, 4.92; Found: C, 79.23; H, 5.10; N, 10.75; S, 4.91

Synthetic example 2: Compound A- 2 of synthesis

[Reaction Scheme 3]

Synthesis of Intermediate 2-1

20.0 g (78.2 mmol) of Intermediate A and 5.34 g (93.8 mmol) of sodium methoxide were added to 550 mL of tetrahydrofuran in a 1000 mL flask, and the mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to column chromatography to obtain Intermediate 2-1 (13.5 g, 69% yield).

calcd. C11H7ClN2OS: C, 52.70; H, 2.81; Cl, 14.14; N, 11.17; O, 6.38; S, 12.79; found: C, 52.71; H, 2.81; Cl, 14.13; N, 11.17; O, 6.38; S, 12.79

Synthesis of Compound A-2

To a 100 mL flask was added 3.0 g (12.0 mmol) of Intermediate 2-1, 6.7 g (13.2 mmol) of Intermediate 1-3, 4.1 g (29.9 mmol) of potassium carbonate and 0.41 g of tetrakis (triphenylphosphine) palladium 0.36 mmol) was added to 40 mL of 1,4-dioxane and 20 mL of water, and the mixture was heated to 65 DEG C for 24 hours under a nitrogen stream. The resulting mixture was added to methanol (120 mL), and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain Compound A-2 , 61% yield).

calcd. C38H25N5OS: C, 76.11; H, 4.20; N, 11.68; O, 2.67; S, 5.35; Found: C, 76.11; H, 4.20; N, 11.69; O, 2.67; S, 5.34

Synthetic example 3: Compound A- 4 of synthesis

[Reaction Scheme 4]

Synthesis of Intermediate 4-1

20.0 g (78.4 mmol) of Intermediate A and 4.85 g (94.1 mmol) of sodium cyanide were added to 550 mL of tetrahydrofuran in a 1000 mL flask, and the mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to column chromatography to obtain Intermediate 4-1 (13.1 g, 67% yield).

calcd. C11H4ClN3S: C, 53.77; H, 1.64; Cl, 14.43; N, 17.10; S, 13.05; found: C, 53.77; H, 1.63; Cl, 14.43; N, 17.11; S, 13.05

Synthesis of Compound A-4

To a 100 mL flask was added 3.0 g (12.2 mmol) of Intermediate 4-1, 6.9 g (13.4 mmol) of Intermediate 1-3, 4.2 g (30.5 mmol) of potassium carbonate, 0.42 g of tetrakis (triphenylphosphine) palladium 0.37 mmol) was added to 40 mL of 1,4-dioxane and 20 mL of water, and the mixture was heated to 65 DEG C for 24 hours under a nitrogen stream. The resulting mixture was added to methanol (120 mL), and the resulting solid was filtered, dissolved in monochlorobenzene, and filtered through silica gel / celite. An organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain 4.79 g , 66% yield).

calcd. For C38H22N6S: C, 76.75; H, 3.73; N, 14.13; S, 5.39; Found: C, 76.75; H, 3.72; N, 14.14; S, 5.39

Synthetic example 4: Compound A- 8 of synthesis

[Reaction Scheme 5]

Synthesis of Intermediate 8-1

To a 500 mL flask was added 10.0 g (39.2 mmol) of Intermediate A, 7.3 g (41.2 mmol) of diphenylamine and 2.0 g (50.9 mmol) of sodium hydride in 550 mL of tetrahydrofuran, Lt; / RTI > The resulting mixture was subjected to column chromatography to obtain Intermediate 8-1 (10.2 g, 67% yield).

calcd. C22H14ClN3S: C, 68.12; H, 3.64; Cl, 9.14; N, 10.83; S, 8.27; Found: C, 68.13; H, 3.64; Cl, 9.11; N, 10.82; S, 8.27

Synthesis of Compound A-8

To a 100 mL flask was added 3.0 g (7.7 mmol) of Intermediate 8-1, 4.4 g (8.5 mmol) of Intermediate 1-3, 2.7 g (19.3 mmol) of potassium carbonate, 0.3 g of tetrakis (triphenylphosphine) palladium 0.23 mmol) was added to 30 mL of 1,4-dioxane and 15 mL of water, and the mixture was heated to 65 DEG C for 24 hours under a nitrogen stream. The resulting mixture was added to 90 mL of methanol, and the crystallized solid was filtered, then dissolved in monochlorobenzene, filtered through silica gel / celite, an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain 3.48 g , 61% yield).

calcd. For C49H32N6S: C, 79.87; H, 4.38; N, 11.40; S, 4.35; Found: C, 79.86; H, 4.38; N, 11.41; S, 4.35

Synthetic example 5: Compound A- 9 of synthesis

[Reaction Scheme 6]

Synthesis of intermediate 9-1

Cyanuric chloride (100.0 g, 542.3 mmol) and 700 mL of anhydrous tetrahydrofuran were placed in a 2000 mL flask, and then phenylmagnesium bromide (3M, 180.7 mL) was slowly added dropwise at 0 ° C. After completion of the reaction, water was poured into the reaction solution and stirred for 30 minutes. The organic layer was separated, and the water was removed by using magnesium sulfate. The filtrate was concentrated and then purified by methanol and hexane to obtain Intermediate 9-1 as a white solid (63.7 g, Yield = 52%).

calcd. C9H5Cl2N3: C, 47.82; H, 2.23; Cl, 31.37; N, 18.59; found:, 47.81; H, 2.22; Cl, 31.38; N, 18.58

Synthesis of intermediate 9-2

60.0 g (265.35 mmol) of Intermediate 9-1, 50.0 g (252.0 mmol) of 3-biphenylboronic acid, 91.6 g (660.0 mmol) of potassium carbonate, tetrakis (triphenylphosphine) palladium 8.0 g (9.2 mmol) was added to 1,4-dioxane (880 mL) and water (440 mL), and the mixture was heated under reflux in a nitrogen stream for 16 hours. The resultant mixture was added to 2700 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered with silica gel / celite, and an organic solvent was removed in an appropriate amount, and then recrystallized with methanol to obtain Intermediate 9-2 , 70% yield).

calcd. C21H14ClN3: C, 73.36; H, 4.10; Cl, 10.31; N, 12.22; Found C, 73.36; H, 4.11; Cl, 10.30; N, 12.23

Synthesis of intermediate 9-3

60.0 g (174.5 mmol) of Intermediate 9-2, 30.0 g (192.0 mmol) of 3-chlorophenylboronic acid, 60.3 g (436.3 mmol) of potassium carbonate, tetrakis (triphenylphosphine) palladium 6.1 g (5.2 mmol) was added to 580 mL of 1,4-dioxane and 290 mL of water, and the mixture was heated under reflux in a nitrogen stream for 16 hours. The resulting mixture was added to 1800 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered with silica gel / celite, and an organic solvent was removed in an appropriate amount, and then recrystallized with methanol to obtain 46.9 g , 64% yield).

calcd. C27H18ClN3: C, 77.23; H, 4.32; Cl, 8.44; N, 10.01; found C, 77.23; H, 4.33; Cl, 8.44; N, 10.00

Synthesis of Intermediate 9-4

To a 1000 mL flask was added Intermediate 9-3 (45.0 g, 107.2 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- (32.7 g, 128.6 mmol), potassium acetate (KOAc, 31.6 g, 321.5 mmol) and 1,1'-bis (diphenylphosphino) ferrocene-palladium (II) dichloride , 6.4 mmol) and tricyclohexylphosphine (9.0 g, 16.1 mmol) were added to N, N-dimethylformamide (500 mL), and the mixture was stirred at 140 占 폚 for 24 hours. After completion of the reaction, the reaction solution was extracted with water and EA. The organic layer was extracted with magnesium sulfate and concentrated. The residue was purified by column chromatography to obtain Intermediate 9-4 as a white solid (38.0 g, yield = 69 %).

calcd. C33H30BN3O2: C, 77.50; H, 5.91; B, 2.11; N, 8.22; 6.26; Found: C, 77.51; H, 5.90; B, 2.12; N, 8.21; O, 6.25

Synthesis of Compound A-9

5.0 g (9.8 mmol) of Intermediate 9-4, 3.3 g (10.8 mmol) of Intermediate 1-4, 3.4 g (24.4 mmol) of potassium carbonate and 0.34 g of tetrakis (triphenylphosphine) palladium 0.29 mmol) was added to 30 mL of 1,4-dioxane and 15 mL of water, and the mixture was heated under reflux in a nitrogen stream for 16 hours. The resulting mixture was added to methanol (100 mL), and the resulting solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain 4.27 g , 67% yield).

calcd. For C43H33N5S: C, 79.23; H, 5.10; N, 10.74; S, 4.92; found C, 79.24; H, 5.09; N, 10.73; S, 4.93

Synthetic example 6: Compound A- Ten synthesis

[Reaction Scheme 7]

To a 100 mL round flask was added 3.0 g (11.97 mmol) of Intermediate 2-1, 6.73 g (13.16 mmol) of Intermediate 9-4, 4.1 g (29.9 mmol) of potassium carbonate, 0.41 g of tetrakis (triphenylphosphine) palladium 0.36 mmol) was added to 1, 4-dioxane (30 mL) and water (15 mL), and the mixture was heated under reflux in a nitrogen stream for 16 hours. The resulting mixture was added to methanol (100 mL), and the crystallized solid was filtered, and the filtrate was dissolved in monochlorobenzene. The filtrate was filtered through silica gel / celite, and an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain 4.59 g , 64% yield).

calcd. C38H25N5OS: C, 76.11; H, 4.20; N, 11.68; O, 2.67; S, 5.35; Found C, 76.11; H, 4.20; N, 11.67; O, 2.67; S, 5.35

Synthetic example 7: Compound A- 12 of synthesis

[Reaction Scheme 8]

To a 100 mL round flask was added 3.0 g (12.21 mmol) of Intermediate 4-1, 6.87 g (13.43 mmol) of Intermediate 9-4, 4.22 g (30.53 mmol) of potassium carbonate, 0.42 g of tetrakis (triphenylphosphine) palladium 0.37 mmol) was added to 40 mL of 1,4-dioxane and 20 mL of water, and the mixture was heated under reflux in a nitrogen stream for 16 hours. The resulting mixture was added to methanol (120 mL), and the resulting solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / celite, and then an organic solvent was removed in an appropriate amount and then recrystallized from methanol to obtain 5.01 g , 69% yield).

calcd. For C38H22N6S: C, 76.75; H, 3.73; N, 14.13; S, 5.39; found C, 76.75; H, 3.73; N, 14.14; S, 5.38

Synthetic example 8: Compound A- 16 synthesis

[Reaction Scheme 9]

To a 100 mL round bottom flask was added 3.0 g (7.7 mmol) of Intermediate 8-1, 4.4 g (8.5 mmol) of Intermediate 9-4, 2.7 g (19.3 mmol) of potassium carbonate and 0.27 g of tetrakis (triphenylphosphine) palladium 0.23 mmol) was added to 26 mL of 1,4-dioxane and 13 mL of water, and the mixture was heated under reflux in a nitrogen stream for 16 hours. The resulting mixture was added to methanol (80 mL), and the crystallized solid was filtered, and the residue was dissolved in monochlorobenzene. The solution was filtered with silica gel / celite, and an organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain 3.53 g , 62% yield).

calcd. For C49H32N6S: C, 79.87; H, 4.38; N, 11.40; S, 4.35; Found C, 79.87; H, 4.38; N, 11.40; S, 4.35

(Second compound)

Synthetic example 9: Synthesis of Compound B-22

[Reaction Scheme 10]

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere were added 16.62 g (51.59 mmol) of 3-bromo-N-phenylcarbazole, 17.77 g (61.91 mmol) of N-phenylcarbazole- After mixing 200 mL of furan: toluene (1: 1) and 100 mL of 2M-potassium carbonate aqueous solution, 2.98 g (2.58 mmol) of tetrakistriphenylphosphine palladium (0) was added and the mixture was heated under reflux for 12 hours in a nitrogen stream . After completion of the reaction, the reaction product was poured into methanol, and the solid matter was filtered, and the obtained solid matter was sufficiently washed with water and methanol and dried. The resulting product was heated to 1 L of chlorobenzene and dissolved. The solution was then filtered through a silica gel filter to remove the solvent completely. The solvent was then dissolved in 500 mL of toluene by heating and then recrystallized to obtain 16.05 g (yield 64%) of Compound B-22 .

calcd. _{C 36 H 24 N 2: C} , 89.23; H, 4.99; N, 5.78; Found: C, 89.45; H, 4.89; N, 5.65

Synthetic example 10: Synthesis of compound B-129

[Reaction Scheme 11]

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere, 20.00 g (42.16 mmol) of 3-bromo-6-phenyl-N-methabiphenylcarbazole and 17.12 g 1.46 g (1.26 mmol) of tetrakistriphenylphosphine palladium (0) was added to 175 ml of tetrahydrofuran: toluene (1: 1) and 75 ml of 2M potassium carbonate aqueous solution, The mixture was heated to reflux for 12 hours. After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid was sufficiently washed with water and methanol, and dried. The resulting solution was heated to 700 mL of chlorobenzene and then the solution was filtered through silica gel to remove the solvent completely. The solvent was then completely dissolved in 400 mL of chlorobenzene by heating and then recrystallized to obtain 18.52 g (yield 69%) of the compound B-129 .

calcd. C ₄₂ H ₃₂ N ₂ : C, 90.54; H, 5.07; N, 4.40; Found: C, 90.54; H, 5.07; N, 4.40

Synthetic example 11: Synthesis of Compound B-133

[Reaction Scheme 12]

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere, 20.00 g (42.16 mmol) of 3-bromo-6-phenyl-N-biphenylcarbazole and 17.12 g 175 mL of tetrahydrofuran: toluene (1: 1) and 75 mL of 2M potassium carbonate aqueous solution were mixed, and 1.46 g (1.26 mmol) of tetrakistriphenylphosphine palladium (0) Lt; / RTI > for one hour. After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid was sufficiently washed with water and methanol, and dried. The resulting product was dissolved in 700 mL of chlorobenzene and dissolved. The solution was then filtered through a silica gel filter to completely remove the solvent. The solvent was then dissolved in 400 mL of chlorobenzene by heating and then recrystallized to obtain 17.45 g (yield 65%) of Compound B- .

calcd. C ₄₂ H ₃₂ N ₂ : C, 90.54; H, 5.07; N, 4.40; Found: C, 90.53; H, 5.08; N, 4.40

Synthetic example 12: Synthesis of compound B-135

[Reaction Scheme 13]

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere was added 20.00 g (50.21 mmol) of 3-bromo-N-biphenylcarbazole, 18.54 g (50.21 mmol) of N-phenylcarbazole- 175 ml of toluene (1: 1) and 75 ml of 2 M potassium carbonate aqueous solution were mixed, and 2.90 g (2.51 mmol) of tetrakistriphenylphosphine palladium (0) was added thereto. The mixture was heated under reflux for 12 hours Respectively. After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid was sufficiently washed with water and methanol, and dried. The resulting solution was heated to 700 mL of chlorobenzene and the solution was filtered through silica gel to remove the solvent completely. The solvent was then completely dissolved by heating in 400 mL of chlorobenzene and then recrystallized to obtain 19.15 g (yield: 68%) of Compound B-135 .

calcd. C ₄₂ H ₂₈ N ₂ : C, 89.97; H, 5.03; N, 5.00; Found: C, 89.53; H, 4.92; N, 4.89

Synthetic example 13: Synthesis of Compound B-1

[Reaction Scheme 14]

To a 500 mL round flask was added 12.81 g (31.36 mmol) of N-phenyl-3,3-bicabazole, 8.33 g (31.36 mmol) of 2-chloro-di-4,6-phenylpyridine, 6.03 g (50% in toluene) were added to 200 mL of xylene and heated for 15 hours in a stream of nitrogen to obtain the title compound Lt; / RTI > The resulting solid was dissolved in dichlorobenzene, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain Compound B-1 (13.5 g, , 68% yield).

calcd. C ₄₇ H ₃₁ N ₃ : C, 88.51; H, 4.90; N, 6.59; Found: C, 88.39; H, 4.64; N, 6.43

Synthetic example 14: Synthesis of compound B-98

[Reaction Scheme 15]

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere was added 15.00 g (37.66 mmol) of 3-bromo-N-biphenylcarbazole, 16.77 g (37.66 mmol) of 3-boronic ester- 200 mL of toluene (1: 1) and 100 mL of a 2M potassium carbonate aqueous solution were mixed, and 2.18 g (1.88 mmol) of tetrakistriphenylphosphine palladium (0) was added thereto. The mixture was heated under reflux for 12 hours Respectively. After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid matter was sufficiently washed with water and methanol and dried. The resulting product was dissolved in 500 mL of chlorobenzene, and the solution was then subjected to silica gel filtration to completely remove the solvent. The solvent was dissolved in 400 mL of toluene by heating and then recrystallized to obtain 16.54 g (yield 69%) of Compound B-98 .

calcd. C ₄₈ H ₃₂ N ₂ : C, 90.54; H, 5.07; N, 4.40; Found: C, 90.52; H, 5.06; N, 4.42

Synthetic example 15: Synthesis of Compound B-99

[Reaction Scheme 16]

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere was added 15.00 g (37.66 mmol) of 3-bromo-N-biphenylcarbazole, 16.77 g (37.66 mmol) of 3-boronic ester- 200 mL of toluene (1: 1) and 100 mL of a 2M potassium carbonate aqueous solution were mixed, and 2.18 g (1.88 mmol) of tetrakistriphenylphosphine palladium (0) was added thereto. The mixture was heated under reflux for 12 hours Respectively. After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid matter was sufficiently washed with water and methanol and dried. The resulting product was dissolved in 500 mL of chlorobenzene. The solution was then subjected to silica gel filtration and the solvent was completely removed. The solvent was dissolved in 400 mL of toluene by heating and then recrystallized to obtain 15.10 g (yield: 63%) of Compound B-99 .

calcd. C ₄₈ H ₃₂ N ₂ : C, 90.54; H, 5.07; N, 4.40; Found: C, 90.54; H, 5.06; N, 4.41

Synthetic example 16: Synthesis of Compound B-136

[Reaction Scheme 17]

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere were added 15.00 g (37.66 mmol) of 3-bromo-N-methabiphenylcarbazole, 16.77 g (37.66 mmol) of 3-boronic ester- And tetrahydrofuran: To a mixture of 200 mL of toluene (1: 1) and 100 mL of a 2M potassium carbonate aqueous solution, 2.18 g (1.88 mmol) of tetrakistriphenylphosphine palladium (0) was added and heated for 12 hours in a nitrogen stream Lt; / RTI > After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid matter was sufficiently washed with water and methanol and dried. The resulting product was dissolved in 500 mL of chlorobenzene. The solution was then subjected to silica gel filtration and the solvent was completely removed. The solvent was dissolved in 400 mL of toluene by heating and then recrystallized to obtain 16.07 g (yield 67%) of Compound B-136 .

calcd. C ₄₈ H ₃₂ N ₂ : C, 90.54; H, 5.07; N, 4.40; found: C, 90.71; H, 5.01; N, 4.27

Synthetic example 17: Synthesis of compound B-137

[Reaction Scheme 18]

In a 250 mL round flask, 6.3 g (15.4 mmol) of N-phenyl-3,3-biscarbazole, 5.0 g (15.4 mmol) of 4- (4-bromophenyl) dibenzo [b, 1.2 g (50% in toluene) of tri (t-butylphosphine) and 0.9 g (1.5 mmol) of tris (dibenzylideneacetone) dipentaerythritol were mixed with 100 mL of xylene, Under reflux for 15 hours. The resulting solid was dissolved in dichlorobenzene, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain 7.3 g of intermediate B-137 , 73% yield).

calcd. For C48H30N2O: C, 88.59; H, 4.65; N, 4.30; O, 2.46; Found: C, 88.56; H, 4.62; N, 4.20; O, 2.43

Synthetic example 18: Synthesis of Compound B-138

[Reaction Scheme 19]

In a 250 mL round flask, 6.1 g (15.0 mmol) of N-phenyl-3,3-biscarbazole, 5.1 g (15.0 mmol) of 4- (4-bromophenyl) dibenzo [b, 1.2 mL (50% in toluene) of tri-t-butylphosphine (0.9 g, 1.5 mmol), tris (dibenzylideneacetone) dipalladium was mixed with 100 mL of xylene, And heated under reflux for 15 hours under an air stream. The resulting mixture was added to methanol (300 mL), and the crystallized solid was filtered and dissolved in dichlorobenzene, filtered through silica gel / celite, an organic solvent was removed in an appropriate amount, and recrystallized from methanol to obtain Intermediate B-138 , 67% yield).

calcd. For C48H30N2S: C, 86.46; H, 4.53; N, 4.20; S, 4.81; Found: C, 86.41; H, 4.51; N, 4.18; S, 4.80

Fabrication of Organic Light Emitting Device I

Example One

The glass substrate on which the ITO electrode was formed was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, and then subjected to UV ozone cleaning for 30 minutes.

M-MTDATA (4,4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) triphenylamine) was vacuum deposited on the ITO electrode at a deposition rate of 1 Å / sec to form a hole injection layer NPB ( N, N' -Di (1-naphthyl) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine) Vacuum deposition was performed at a deposition rate of 1 ANGSTROM / sec to form a hole transport layer having a thickness of 300 ANGSTROM. Next, Ir (ppy) ₃ (dopant) and Compound A-1 were co-deposited at a deposition rate of 0.1 Å / sec and 1 Å / sec, respectively, on the hole transport layer to form a light emitting layer having a thickness of 400 Å. BAlq was vacuum deposited on the light emitting layer at a deposition rate of 1 Å / sec to form a hole blocking layer having a thickness of 50 Å. Then, Alq ₃ was vacuum deposited on the hole blocking layer to form an electron transporting layer having a thickness of 300 Å. LiF 10 Å (electron injecting layer) and Al 2000 Å (cathode) were sequentially vacuum-deposited on the electron transporting layer to prepare an organic light emitting device.

Example 2 to Example 8

Except that compounds A-2, A-4, A-8, A-9, A-10, A-12 and A-16 were used as the host in forming the light emitting layer, Using the same method as in Example 1, organic light emitting devices corresponding to Examples 2 to 8 were produced.

Comparative Example One

An organic light emitting device was fabricated using the same method as in Example 1 except that Compound A was used instead of Compound A-1 as a host in forming the light emitting layer.

Comparative Example 2

An organic light emitting device was fabricated using the same method as in Example 1 except that Compound B was used instead of Compound A-1 as a host in forming the light emitting layer.

Comparative Example 3

An organic light emitting device was fabricated using the same method as in Example 1 except that Compound C was used instead of Compound A-1 as a host in forming the light emitting layer.

Comparative Example 4

An organic light emitting device was fabricated using the same method as in Example 1 except that Compound D was used instead of Compound A-1 as a host in forming the light emitting layer.

Evaluation example 1: Characteristic evaluation of organic light emitting device (I)

The driving voltage, current efficiency, and luminance of the organic light emitting devices of Examples 1 to 8 and Comparative Examples 1 to 4 were measured using a luminance meter PR650 Spectroscan Source Measurement Unit (manufactured by PhotoResearch Co., Ltd.) by supplying power from a current voltmeter (Kethley SMU 236) The results are shown in Table 1 below.

The specific measurement method is as follows.

(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).

Yes Host Dopant Driving
Voltage
(V) Current efficiency
(cd / A) Luminance
(cd / m ² ) Example 1 Compound A-1 Ir (ppy) ₃ 4.12 41.6 6000 Example 2 Compound A-2 Ir (ppy) ₃ 4.02 42.9 6000 Example 3 Compound A-4 Ir (ppy) ₃ 3.91 45.3 6000 Example 4 Compound A-8 Ir (ppy) ₃ 4.41 43.7 6000 Example 5 Compound A-9 Ir (ppy) ₃ 3.94 42.7 6000 Example 6 Compound A-10 Ir (ppy) ₃ 3.88 44.3 6000 Example 7 Compound A-12 Ir (ppy) ₃ 3.73 46.4 6000 Example 8 Compound A-16 Ir (ppy) ₃ 4.22 44.1 6000 Comparative Example 1 Compound A Ir (ppy) ₃ 5.0 38 6000 Comparative Example 2 Compound B Ir (ppy) ₃ 5.1 29 6000 Comparative Example 3 Compound C Ir (ppy) ₃ 4.8 34 6000 Comparative Example 4 Compound D Ir (ppy) ₃ 4.8 31 6000

From Table 1, it can be confirmed that the organic light emitting devices of Examples 1 to 8, which are the compounds of the present invention, have a lower driving voltage and higher efficiency than the organic light emitting devices of Comparative Examples 1 to 4.

It is a phosphorescent host material that has excellent charge transport properties and can overlap with the absorption spectrum of the dopant. It can be seen that the performance is improved and the ability as an OLED material is maximized, such as an increase in efficiency and a reduction in driving voltage.

Fabrication of Organic Light Emitting Device II

Example 9

Ir (ppy) ₃ (dopant), Compound A-1 (first host) and Compound B-136 (second host) were co-deposited on the hole transport layer at a weight ratio of 10:45:45, The organic light emitting device was fabricated in the same manner as in Example 1, except that a light emitting layer was formed.

Example 10 - Example 16

Except that Compound A-2, A-4, A-8, A-9, A-10, A-12 and A-16 were used in place of Compound A- 9, organic light emitting devices corresponding to Examples 10 to 16 were fabricated.

Example 17

Ir (ppy) ₃ (dopant), Compound A-9 (first host) and Compound B-98 (second host) were co-deposited on the hole transport layer at a weight ratio of 10:45:45, To form a light emitting layer, thereby fabricating an organic light emitting device.

Example 18 - Example 20

Examples 18 to 20 were prepared in the same manner as in Example 17 except that the compounds A-10, A-12 and A-16 were used instead of the compound A-1 in the formation of the light- Was prepared.

Evaluation example 2: Characteristic Evaluation of Organic Light Emitting Device (II)

The driving voltage, the efficiency, the luminance and the lifetime of the organic light emitting devices of Examples 9 to 20 and Comparative Examples 1 to 4 were supplied with power from a current voltmeter (Kethley SMU 236) and measured at a brightness of PR650 Spectroscan Source Measurement Unit. (PhotoResearch The results are shown in Table 2 below.

Yes The first host Second host Dopant Driving
Voltage
(V) Current efficiency
(cd / A) Luminance
(cd / m ² ) Example 9 Compound A-1 B-136 Ir (ppy) ₃ 4.08 42.7 6000 Example 10 Compound A-2 B-136 Ir (ppy) ₃ 3.94 43.8 6000 Example 11 Compound A-4 B-136 Ir (ppy) ₃ 3.86 46.1 6000 Example 12 Compound A-8 B-136 Ir (ppy) ₃ 4.26 44.2 6000 Example 13 Compound A-9 B-136 Ir (ppy) ₃ 3.88 43.9 6000 Example 14 Compound A-10 B-136 Ir (ppy) ₃ 3.72 45.7 6000 Example 15 Compound A-12 B-136 Ir (ppy) ₃ 3.66 47.3 6000 Example 16 Compound A-16 B-136 Ir (ppy) ₃ 4.15 45.0 6000 Example 17 Compound A-9 B-98 Ir (ppy) ₃ 3.72 44.3 6000 Example 18 Compound A-10 B-98 Ir (ppy) ₃ 3.67 46.2 6000 Example 19 Compound A-12 B-98 Ir (ppy) ₃ 3.58 47.5 6000 Example 20 Compound A-16 B-98 Ir (ppy) ₃ 4.02 43.0 6000

It can be seen from Table 2 that the organic luminescent devices of Examples 9 to 20, which are the compounds of the present invention, use the first compound and the second compound in combination, and have lower driving voltage or higher efficiency than the organic luminescent devices of Comparative Examples 1 to 4 .

Fabrication of organic light emitting device III

Example 21

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, HT13 of the following structure was vacuum deposited on the ITO substrate to form a 1400 A thick hole injection and transport layer. Subsequently, BH113 and BD370, which are sold by SFC, were doped as a blue fluorescent light emitting host and a dopant on the hole transport layer to a thickness of 200 ANGSTROM to form a light emitting layer. Compound A-1 of Synthesis Example 1 was then vacuum-deposited on the light-emitting layer to form an electron transporting layer having a thickness of 50 Å. Tris (8-hydroxyquinoline) aluminum (Alq ₃ ) was vacuum deposited on the electron transporting auxiliary layer to form an electron transporting layer having a thickness of 310 Å. Liq 15 Å and Al 1200 Å were sequentially vacuum deposited on the electron transporting layer, Thereby forming an organic light emitting device.

The organic light emitting device has a structure having five organic thin film layers. Specifically,

The structure of ITO / HT13 (1400 Å) / EML [BH113: BD370 = 95: 5 wt%] (200 Å) / Compound A-1 (50 Å) / Alq3 (310 Å) / Liq (15 Å) / Al Respectively.

<HT13>

Example 22

An organic luminescent device was prepared in the same manner as in Example 21 except that the compound A-2 of Synthesis Example 2 was used instead of the compound A-1 of Example 21.

Example 23

An organic luminescent device was prepared in the same manner as in Example 21 except that the compound A-4 of Synthesis Example 3 was used instead of the compound A-1 of Example 21.

Example 24

An organic luminescent device was prepared in the same manner as in Example 21 except that the compound A-9 of Synthesis Example 5 was used instead of the compound A-1 of Example 21.

Example 25

An organic luminescent device was prepared in the same manner as in Example 21 except that the compound A-10 of the synthesis example 6 was used instead of the compound A-1 of the example 21.

Example 26

An organic luminescence device was prepared in the same manner as in Example 21 except that the compound A-12 of the synthesis example 7 was used instead of the compound A-1 of the example 21.

Comparative Example 5

An organic light emitting device was prepared in the same manner as in Example 21 except that the electron transporting auxiliary layer was not included.

Evaluation example 3: Characteristic evaluation of organic light emitting device (III)

The organic light emitting devices manufactured in Examples 21 to 26 and Comparative Example 5 were measured for current density change, luminance change and luminous efficiency according to voltage, and the results are shown in Table 3 below.

The lifetime was measured by emitting light of 750 cd / m ² at an initial luminance (cd / m ² ) of the devices of Examples 21 to 26 and Comparative Example 5 using the Polarronix lifetime measuring system for the organic light emitting device manufactured, And the time at which the luminance was reduced to 97% of the initial luminance was measured as the T97 lifetime.

device Electron transporting auxiliary layer Driving voltage Luminous efficiency The color coordinates (x, y) T97 Life (h) @ 750nit Example 21 Compound A-1 4.96 7.0 (0.133, 0.147) 123 Example 22 Compound A-2 4.75 7.1 (0.133, 0.147) 126 Example 23 Compound A-4 4.66 7.5 (0.133, 0.147) 129 Example 24 Compound A-9 4.93 7.1 (0.133, 0.147) 126 Example 25 Compound A-10 4.88 7.3 (0.133, 0.147) 129 Example 26 Compound A-12 4.60 8.2 (0.133, 0.147) 141 Comparative Example 5 not used 5.02 6.8 (0.133, 0.147) 120

According to Table 3, it can be seen that the lifetime of the organic light emitting device according to Examples 21 to 26 of the present invention is longer than that of the organic light emitting device according to Comparative Example 5. From this, it was confirmed that lifetime characteristics of the organic light emitting device can be improved by the electron transporting auxiliary layer according to the present invention, and the luminous efficiency was also equal to or higher than that, and it was confirmed that the driving voltage was lowered.

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

Claims

A compound for an organic optoelectronic device represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
X is O or S,
Wherein ^{one of} R ¹ and R ² is a substituted or unsubstituted N-containing C2 to C30 heterocyclic group and the other is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, An unsubstituted C3 to C30 cycloalkyl group, a C6 to C20 arylamine group or a cyano group,
R ³ to R ⁶ are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, A substituted C2-C30 heterocyclic group, or a combination thereof,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
The term "substituted" as used herein means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, 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 C2 to C30 heterocycloalkyl group, To C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.

The method according to claim 1,
Wherein any one of R ¹ and R ² is a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted quinoline group, Substituted or unsubstituted naphthyridinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinoxalinyl groups, , A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted cyano group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted quinazolinyl group, Substituted or unsubstituted benzothiazolyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted benzothiazolyl groups, substituted or unsubstituted benzoxazolyl groups, substituted or unsubstituted benzothiazolyl groups, substituted or unsubstituted benzothiazolyl groups, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, A substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzo Azole group, raised a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted benzo isoquinolinium group, a substituted or unsubstituted benzo quinazolinyl group, or a substituted or unsubstituted quinoxaline the benzo ring and the group,
And the other is an organic optoelectronic element in which the alkyl group is an alkyl group, an ethyl group, a propyl group, an isopropyl group, a methoxy group, an ethoxy group, a diphenylamine group, a cyano group, a substituted or unsubstituted cyclopentyl group, or a substituted or unsubstituted cyclohexyl group / RTI >

The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by the following Formula 1-I or 1-II:
[Chemical Formula 1-I] [Chemical Formula 1-II]

In the above general formulas (I-1) and (II-II)
X is O or S,
R ¹ and R ² each independently represent a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a C6 to C20 arylamine group, Anger,
Z is each independently N or CR ^a , at least one of Z is N,
R ³ to R ⁸ and R ^a are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L ¹ and L ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
&Quot; Substitution " is the same as defined in the above item 1.

The method of claim 3,
R ⁷ and R ⁸ each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group , A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, or a combination thereof.

The method of claim 3,
Wherein the formula 1 is represented by the formula 1-II,
In the above formula (I-II)
X is O or S,
R ¹ is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a C6 to C20 arylamine group or a cyano group,
Z is each independently N or CR ^a , at least one of Z is N,
R ³ to R ⁸ and R ^a are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group , A substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L < ¹ > is a single bond,
L ² is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Herein, " substituted " means a compound for organic optoelectronic devices as defined in the above item 1.

The method according to claim 1,
Wherein L ¹ and L ² each independently represent a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quaterphenylene group, Substituted naphthylene group.

The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the following Group A:
[Group A]

.

A compound for an organic optoelectronic device according to claim 1; And
A compound for an organic optoelectronic device represented by the following formula (2)
Wherein the organic photovoltaic device comprises:
(2)

In Formula 2,
Each of L ¹ to L ³ , Y ¹ , and Y ⁴ is independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof ,
Ar ¹ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ⁹ to R ¹¹ , and R ¹⁷ to R ¹⁹ are A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof,
m is an integer of 0 to 4,
Wherein " substituted " is as defined in claim 1.

9. The method of claim 8,
Ar ¹ and Ar ⁴ in Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted A substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl group, A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted pyridinyl group, or a combination thereof.

9. The method of claim 8,
Wherein the formula (2) is one of the structures listed in the following Group 1, and * -Y ¹ -Ar ¹ , * -Y ⁴ -Ar ⁴ is one of the substituents listed in the following Group 2:
[Group 1]

[Group 2]

B-16 B-17 B-18
In the groups 1 and 2, * is a connection point.

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 is the compound for an organic optoelectronic device according to any one of claims 1 to 7. Or an organic optoelectronic device comprising the composition for organic optoelectronic devices according to any one of claims 8 to 10.

12. The method of claim 11,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound for an organic optoelectronic device or a composition for an organic optoelectronic device.

13. The method of claim 12,
Wherein the compound for an organic optoelectronic device or the composition for the organic optoelectronic device is included as a host of the light emitting layer.

12. The method of claim 11,
Wherein the organic layer includes an electron transporting auxiliary layer adjacent to the light emitting layer,
Wherein the electron transporting auxiliary layer comprises the compound for an organic optoelectronic device; Or a composition for the organic optoelectronic device.

12. A display device comprising the organic electroluminescent device according to claim 11.