KR20190001116A - Compound for organic optoelectronic device and composition for organic optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to a composition for an organic optoelectronic device, and the organic optoelectronic device and a display device using the same. The composition for an organic optoelectronic device includes: a compound for a first organic optoelectronic device represented by formula 1; and a compound for a second organic optoelectronic device comprising the compound for the first organic optoelectronic device and a combination of a moiety represented by formula 2 and a moiety represented by formula 3. The description of the formulas 1 to 3 us as defined in the specification. It is possible to provide a high-efficiency and long-life organic optoelectronic device.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. BACKGROUND OF THE INVENTION 1. Field of the Invention [0001]

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

An organic optoelectronic diode is an element that can switch between electric energy and light 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 above compound.

Yet another embodiment provides an organic optoelectronic device comprising the compound or composition.

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

According to one embodiment, there is provided a compound for a first organic optoelectronic device represented by Formula 1 below.

[Chemical Formula 1]

In Formula 1,

Z ¹ to Z ⁶ are each independently N or CR ^c ,

At least two of Z ¹ to Z ³ are N,

At least two of Z ⁴ to Z ⁶ are N,

R ¹ to R ³ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ^a , R ^b and R ^c are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,

X is O or S;

According to another embodiment, the compound for the first organic optoelectronic device; And a compound for a second organic optoelectronic device comprising a combination of a moiety represented by the following formula (2) and a moiety represented by the following formula (3).

[Chemical Formula 2] < EMI ID =

In the general formulas (2) and (3)

Y ¹ and Y ² are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophen yl group,

The adjacent two * in the above formula (2) are connected with two * in the above formula (3) to form a fused ring. In the above formula (2), * without the fused ring is independently CL ^a -R ^d ,

R ^d and R ⁴ to R ⁷ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, Or a combination thereof,

L ^a , 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.

According to 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, wherein the organic layer is a compound for the organic optoelectronic device or a composition And an organic electroluminescent device.

According to another embodiment, there is provided a display device including the organic optoelectronic device.

High-efficiency long-lived organic optoelectronic devices can be realized.

1 to 3 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

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 hydrogen in the substituent or compound is replaced with a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, A C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 aryl group, Substituted with a C1-C20 alkyl group, a C1-C20 alkoxy group, a fluoro group, a C1-C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In one embodiment of the invention, " substituted " means that at least one of the substituents or the hydrogen in the compound is deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, A heterocycloalkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In a specific example of the present invention, "substituted" means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In a specific example of the present invention, " substituted " means that at least one hydrogen in the substituent or the compound is substituted with a substituent such as deuterium, methyl, ethyl, A fluorenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group. In the most specific example of the present invention, " substituted " means, for example, that at least one hydrogen in a substituent or a compound is a phenyl group, a para- , 9-carbazolyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 2-dibenzothiophenyl group, or 3-dibenzothiophenyl 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, 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 " refers to a group of groups having at least one hydrocarbon aromatic moiety,

A structure in which all the elements of the hydrocarbon aromatic moiety have a p-orbital and these p-orbital forms a conjugation, such as a phenyl group and a naphthyl group,

A structure in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarter-phenyl group,

Two or more hydrocarbon aromatic moieties 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.

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 containing at least one heteroatom selected from the group consisting of N, O, S, P and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused together. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

The heterocyclic group may include, for example, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like.

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 Substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted naphthacenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted p-terphenyl groups, substituted or unsubstituted naphthacenyl groups, A substituted or unsubstituted naphthyl group, a substituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, A substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, Substituted or unsubstituted oxadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, A substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group , A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted azo group A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted dibenzofuranyl group, Thiophene group, or a combination thereof, but is not limited thereto.

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

The compound for a first organic optoelectronic device according to one embodiment may be represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Z ¹ to Z ⁶ are each independently N or CR ^c ,

At least two of Z ¹ to Z ³ are N,

At least two of Z ⁴ to Z ⁶ are N,

R ¹ to R ³ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ^a , R ^b and R ^c are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,

X is O or S;

Means that at least one hydrogen is substituted with deuterium, cyano, C1 to C4 alkyl, C6 to C18 aryl, or C2 to C18 heteroaryl groups. Means that at least one hydrogen is substituted with deuterium, a cyano group, a C1 to C4 alkyl group, a C6 to C12 aryl group, or a C2 to C12 heteroaryl group in the formula (1). In the specific example of the present invention, the "substitution" in the above formula (1) means that at least one hydrogen atom is substituted with a substituent selected from the group consisting of deuterium, cyano group, phenyl group, meta-biphenyl group, para-biphenyl group, naphthyl group, dibenzofuranyl group, Substituted by a thiophene group.

The compound for the first organic optoelectronic device according to the present invention is a compound for the first organic optoelectronic device wherein the ET unit including an N-containing 6-membered ring is directly connected at the 3-position of dibenzofuran or dibenzothiophene without a linker, thereby effectively expanding the LUMO energy band, The structure of the organic electroluminescent device increases the planarity of the organic electroluminescent device, thereby allowing electrons to be easily received when an electric field is applied. In addition, the fusion of the LUMO and the ring increases the stability of the ET unit to electrons, which is effective in improving the lifetime of the device.

In addition, the ET unit including the N-containing 6-membered ring has a deep LUMO energy value as the two ET moieties are bonded with para around the phenylene, thereby enhancing the influence between the ET moieties, The driving voltage of the device can be further lowered.

In one embodiment of the invention, the ET moiety consisting of Z ¹ to Z ³ and the ET moiety consisting of Z ⁴ to Z ⁶ can each be pyrimidine or triazine,

When Z ¹ to Z ⁶ are CR ^c , R ^c may be, for example, hydrogen, deuterium, cyano group, nitro group, substituted or unsubstituted C 1 to C 4 alkyl group, or substituted or unsubstituted C 6 to C 12 aryl group, In a specific embodiment of the invention, R ^c may be hydrogen, deuterium, or a phenyl group, and in a most specific embodiment of the present invention, R ^c may be all hydrogen.

The compound for a first organic optoelectronic device according to an embodiment of the present invention may be represented by any of Formula 1-1 to Formula 1-8 according to the specific structure of ET mimetic.

[Formula 1-1] [Formula 1-2] [Formula 1-3]

[Formula 1-4] [Formula 1-5] [Formula 1-6]

[Chemical Formula 1-7] [Chemical Formula 1-8]

In Formulas 1-1 to 1-8, R ¹ to R ³ , R ^a and R ^b , and X are as described above.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the formulas (1-1) to (1-4) 4 < / RTI >

In one embodiment of the present invention, R ¹ to R ³ in Formula 1 are each independently a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothi In one specific embodiment, R ¹ to R ³ in the above-mentioned 1 each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted meta-biphenyl group, a substituted or unsubstituted para-biphenyl group , A substituted or unsubstituted ortho-biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, For example, R ¹ to R ³ in Formula 1 may be independently selected from the substituents listed in the following Group I.

[Group I]

In the above group I, * is a connection point.

In a more specific embodiment, R ¹ to R ³ in the above 1 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted meta-biphenyl group, a substituted or unsubstituted dibenzofuranyl group, Or a substituted dibenzothiophenyl group.

In one embodiment of the present invention, R ^a , R ^b and R ^c are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C4 alkyl group, or substituted or unsubstituted C6 to C12 aryl And may be hydrogen, deuterium, methyl group, ethyl group, n-propyl group, iso-propyl group, or phenyl group in a specific embodiment, and may be hydrogen in a more specific embodiment.

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

[Group 1]

[A-1] [A-2] [A-3] [A-4]

[A-5] [A-6] [A-7] [A-8]

[A-9] [A-10] [A-11] [A-12]

[A-13] [A-14] [A-15] [A-16]

[A-17] [A-18] [A-19] [A-20]

[A-21] [A-22] [A-23] [A-24]

[A-25] [A-26] [A-27] [A-28]

[A-29] [A-30] [A-31] [A-32]

[A-33] [A-34] [A-35] [A-36]

[A-37] [A-38] [A-39] [A-40]

[A-41] [A-42] [A-43] [A-44]

[A-45] [A-46] [A-47] [A-48]

[A-49] [A-50] [A-51] [A-52]

[A-53] [A-54] [A-55] [A-56]

[A-57] [A-58] [A-59] [A-60]

[A-61] [A-62] [A-63] [A-64]

[A-65] [A-66] [A-67] [A-68]

[A-69] [A-70] [A-71] [A-72]

[A-73] [A-74] [A-75] [A-76]

[A-77] [A-78] [A-79] [A-80]

[A-81] [A-82] [A-83] [A-84]

[A-85] [A-86] [A-87] [A-88]

[A-89] [A-90] [A-91] [A-92]

Hereinafter, a composition for an organic optoelectronic device according to another embodiment will be described.

The composition for an organic optoelectronic device according to another embodiment may be applied in the form of a composition for a second organic optoelectronic device together with the compound for the first organic optoelectronic device described above.

The second organic optoelectronic device compound comprises a combination of a moiety represented by the following formula (2) and a moiety represented by the following formula (3).

[Chemical Formula 2] < EMI ID =

In the general formulas (2) and (3)

Y ¹ and Y ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

The adjacent two * in the above formula (2) are connected with two * in the above formula (3) to form a fused ring. In the above formula (2), * without the fused ring is independently CL ^a -R ^d ,

R ^d and R ⁴ to R ⁷ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, Or a combination thereof,

L ^a , 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.

Means that at least one hydrogen is substituted with a deuterium, a cyano group, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C18 heterocyclic group. In one embodiment of the present invention, the "substitution" in the above Chemical Formulas 2 and 3 means that at least one hydrogen is substituted with deuterium, cyano, C1 to C4 alkyl, C6 to C12 aryl or C2 to C12 heterocyclic groups it means. In the specific example of the present invention, the "substitution" in the above-mentioned formulas (2) and (3) means that at least one hydrogen is substituted with a substituent selected from the group consisting of deuterium, cyano group, phenyl group, meta-biphenyl group, para-biphenyl group, carbazolyl group, A dibenzofuranyl group or a dibenzothiophenyl group.

When the compound for the second organic optoelectronic device having a relatively high hole property is used in the light emitting layer together with the compound for the first organic optoelectronic device described above, charge is balanced in the light emitting layer, thereby realizing a long-life organic light emitting device.

The compound for a second organic optoelectronic device according to an embodiment of the present invention may be represented by any of the following formulas (2A), (2B), (2C), (2D) and .

[Chemical Formula 2B] < EMI ID =

[Chemical Formula 2E] [Chemical Formula 2E]

In the above Chemical Formulas 2A to 2E, L ¹ and L ² , Y ¹ and Y ² , and R ⁴ to R ⁷ are as defined above,

R ^d1 and R ^d4 to R ^d6 are the same as defined above for R ^d and are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 hetero Can be a ring.

Specifically, R ^d1 and R ^d4 to R ^d6 each independently represent hydrogen, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group And more particularly, all hydrogen.

L ^a1 , and L ^a4 through L ^a6 are the same as defined for L ^a described above, and may be, for example, each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group.

Specifically, each of L ^a1 and L ^a4 to L ^a6 is independently a single bond, a substituted or unsubstituted para-phenylene group, a substituted or unsubstituted meta-phenylene group, or a substituted or unsubstituted biphenylene group .

In a most specific embodiment of the present invention, R ^d1 and R ^d4 To R ^d6 are each independently hydrogen, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, wherein at least one of R ^d1 and R ^d4 Substituted or unsubstituted dibenzothiophene group, and the remainder are all hydrogen, and L ^a1 and L ^a4 through L ^a6 are each ^{independently} hydrogen or a substituted or unsubstituted dibenzofuranyl group, Or a substituted or unsubstituted C6 to C18 arylene group, provided that at least one of L ^a1 and L ^a4 is a single bond, a substituted or unsubstituted para-phenylene group, a substituted or unsubstituted meta- A phenylene group, or a substituted or unsubstituted biphenylene group, all of which may be a single bond. As a more specific example, R ^d1 and R ^d4 To R ^d6 are all hydrogen, and each of L ^a1 and L ^a4 to L ^a6 may be a single bond.

The compound for a second organic optoelectronic device according to an embodiment of the present invention may be represented by any of Formula 2A, Formula 2C, Formula 2D and Formula 2E, Or < / RTI >

In one embodiment of the present invention, L ¹ and L ² are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, And Y ¹ and Y ² 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 naphthyl group, A substituted or unsubstituted thiophenylene group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, A substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

In one embodiment of the present invention, Y ¹ and Y ² are selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, A substituted or unsubstituted dibenzothiophenyl group, wherein the substitution means that any one hydrogen is substituted with deuterium, a C1 to C5 alkyl group or a C6 to C18 aryl group.

In an specific embodiment of the invention, wherein L ¹ and L ² are each independently a single bond, phenylene group, meta-, para- phenylene group, a biphenyl group, or may be a pyridinyl alkenylene group, wherein Y ¹ and Y ² Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted pyridinyl group, Or a substituted dibenzothiophenyl group,

In a more specific embodiment, L ¹ and L ² may each independently be a single bond or a phenylene group, and Y ¹ and Y ² may each independently be selected from the substituents listed in the following Group II.

[Group II]

In the above group II, * is a connection point with L ¹ and L ² , respectively.

In the most specific embodiment of the present invention, L ¹ and L ² are each independently a single bond or a para-phenylene group, Y ¹ and Y ² are each independently a substituted or unsubstituted phenyl group, Or an unsubstituted carbazolyl group.

The compound for a first organic optoelectronic device included in the composition for an organic optoelectronic device according to a preferred embodiment may be selected from among the compounds represented by Formulas 1-1, 1-3, and 1-4, The compound can be represented by the above formula (2A) or (2D).

More preferably, the compound for a first organic optoelectronic device may be represented by Formula 1-1 or Formula 1-4, and the compound for a second organic optoelectronic device may be represented by Formula 2A or Formula 2D, The compound for the first organic optoelectronic device may be represented by the formula 1-3, and the compound for the second organic optoelectronic device may be represented by the formula 2d.

The compound for the second organic optoelectronic device composed of the combination of the moiety represented by Formula 2 and the moiety represented by Formula 3 may be selected from compounds listed in the following Group 2, but is not limited thereto.

[Group 2]

[B-1] [B-2] [B-3] [B-4]

[B-6] [B-7] [B-8] [B-9]

[B-11] [B-12] [B-13] [B-14]

[B-16] [B-17] [B-18] [B-19]

[B-21] [B-22] [B-23] [B-24]

[B-26] [B-27] [B-28] [B-29] [B-30]

[B-31] [B-32] [B-33] [B-34]

[B-36] [B-37] [B-38] [B-39]

[B-41] [B-42] [B-43] [B-44]

[B-46] [B-47] [B-48] [B-49]

[B-51] [B-52] [B-53] [B-54]

[B-56] [B-57] [B-58] [B-59]

[B-61] [B-62] [B-63] [B-64] [B-65]

[B-66] [B-67] [B-68] [B-69]

[B-71] [B-72] [B-73] [B-74]

[B-76] [B-77] [B-78] [B-79]

[B-81] [B-82] [B-83] [B-84]

[B-86] [B-87] [B-88] [B-89]

[B-91] [B-92] [B-93] [B-94]

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

The compounds for the first organic optoelectronic device and the compound for the second organic optoelectronic device described above can be prepared in various compositions by various combinations.

The compound for the second organic optoelectronic device may be used in the light emitting layer together with the compound for the first organic optoelectronic device to increase the mobility of the charge and increase the stability, thereby improving the luminous efficiency and lifetime. Also, the charge mobility can be controlled by controlling the ratio of the compound for the second organic optoelectronic device and the compound for the first organic optoelectronic device.

Such as from about 1: 9 to about 9: 1, and more specifically from 2: 8 to 8: 2, from 3: 7 to 7: 3, from 4: 6 to 6: 4, and from 5: 5 And can be specifically included in a weight ratio of 1: 9 to 9: 1, 2: 8 to 8: 2, 3: 7 to 7: 3. In an embodiment of the present invention, the compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device may be contained at a weight ratio of 5: 5 to 2: 8, and may be contained at a weight ratio of 5: 5 to 3: 7.

For example, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device can be contained in a weight ratio of 3: 7. By including it in the above range, the efficiency and the life can be improved at the same time.

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

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 organic optoelectronic device to which the composition for an organic optoelectronic device described above is applied will be described.

Another organic optoelectronic device according to another embodiment 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 an organic optoelectronic device described above, And compositions for organic optoelectronic devices.

For example, the organic layer includes an auxiliary layer including at least one of a hole injection layer, a hole transport layer, an electron injection layer and an electron transport layer, and a light emitting layer,

The auxiliary layer may include the compound for organic optoelectronic devices of the present invention. Specifically, the compound for an organic optoelectronic device may be included in an electron transport layer.

In addition, the light emitting layer may include the composition for organic optoelectronic devices of the present invention. Specifically, the composition for the organic optoelectronic device may be included as a host of the light emitting layer, for example, a green host.

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 to 3 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

1, an organic light emitting device 100 according to an exemplary embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed 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.

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

5, the organic layer 105 has different functions such as an electron injection layer 160, an electron transport layer 150, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170 Layer organic light emitting device 500. The organic light emitting device 500 is formed separately from the electron injection layer 160 and is effective for lowering the voltage.

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.

(Compound for first organic optoelectronic device)

Synthetic example  1: Synthesis of Compound A-1

[Reaction Scheme 1]

a) Synthesis of intermediate A-1-1

2,4-dichloro-6-phenyl-1,3,5-triazine (50 g, 221 mmol), 3-bromodibenzofuranylboronic acid (46.8 g, 221 mmol), tetrakis (triphenylphosphine) palladium (0) 11 mmol) and potassium carbonate (76.4 g, 553 mmol) were dissolved in a 1.5 L tetrahydrofuran: DIW = 2: 1 mixed solution, and the mixture was refluxed at 80 ° C for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. The intermediate A-1-1 (39.8 g, Y = 50.3%) was obtained by recrystallization from a dichloromethane: n- hexane mixed solution.

b) Synthesis of intermediate A-1-2

Intermediate A-1-1 and 4-chlorophenylboronic acid were synthesized using the Suzuki reaction as in the synthesis example of intermediate A-1-1, and recrystallized from toluene to obtain intermediate A-1-2. (Y = 72.9%)

c) Synthesis of intermediate A-1-3

Intermediate A-1-2 (25.0 g, 58 mmol), bis (pinacolato) diboron (22.0 g, 87 mmol), potassium acetate (17.0 g, 173 mmol), tricyclohexylphosphine (3.9 g, -bis (diphenylphosphino) ferrocene] -dichloropalladium (II) (2.4 g, 3 mmol) was added to 300 mL of N , N- dimethylformamide and the mixture was refluxed at 150 ° C for 12 hours. When the reaction is complete, the solution is placed in an excess of DIW to form a precipitate. The precipitate is filtered, boiled in toluene and dissolved in silica gel. The filtrated solution was recrystallized to obtain intermediate A-1-3 (19.1 g, Y = 63.1%).

d) Synthesis of Compound A-1

Intermediates A-1-3 and 2-chloro-4,6-diphenylpyrimidine were synthesized by Suzuki reaction as in the synthesis example of intermediate A-1-1, and recrystallized from 1,2-dichlorobenzene to give Compound A -1. (Y = 55.4%)

Synthetic example  2: Synthesis of Compound A-17

[Reaction Scheme 2]

a) Synthesis of intermediate A-17-1

In a nitrogen atmosphere, magnesium (7.86 g, 323 mmol) and iodine (1.64 g, 6.46 mmol) were added to 0.1 L of tetrahydrofuran (THF) and stirred for 30 minutes. Then, 3-bromodibenzofuran (80 g, 323 mmol) is slowly added dropwise at 0 < 0 > C over 30 minutes. The resulting mixture is slowly added dropwise to a solution of 64.5 g (350 mmol) of cyanuric chloride in 0.5 L of THF at 0 ° C over 30 minutes. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with dichloromethane (DCM), followed by removal of water with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The residue thus obtained was purified by flash column chromatography to obtain intermediate A-17-1 (79.4 g, 65%).

b) Synthesis of intermediate A-17-2

Intermediate A-17-1 and 3-dibenzofuranylboronic acid were synthesized using the Suzuki reaction as in the synthesis example of intermediate A-1-1, and recrystallized with chlorobenzene to obtain intermediate A-17-2. (Y = 66.7%)

c) Synthesis of intermediate A-17-3

Intermediate A-17-2 and 4-chlorophenylboronic acid were synthesized using the Suzuki reaction as in the synthesis example of intermediate A-1-1, and recrystallized from 1,2-dichlorobenzene to obtain intermediate A-17-3 . (Y = 74.5%)

d) Synthesis of intermediate A-17-4

Intermediate A-17-3 was synthesized by using borylation as the starting material for intermediate A-1-3, and recrystallized from chlorobenzene to obtain intermediate A-17-4. (Y = 52.5%)

e) Synthesis of compound A-17

Intermediate A-17-4 and 2-chloro-4,6-diphenylpyrimidine were synthesized by Suzuki reaction as in Synthesis Example of Intermediate A-1-1, and recrystallized from 1,2-dichlorobenzene to obtain Compound A -17. (Y = 77.2%)

Synthetic example  3: Synthesis of Compound A-25

[Reaction Scheme 3]

a) Synthesis of intermediate A-25-1

2,4-dichloro-6-phenylpyrimidine and 3-dibenzofuranyl boronic acid were synthesized by the Suzuki reaction as in the synthesis of Intermediate A-1-1, and recrystallized from a dichloromethane: n- hexane mixed solution. A-25-1. (Y = 87.5%)

b) Synthesis of intermediate A-25-2

Intermediate A-25-1 and 4-chlorophenylboronic acid were synthesized using the Suzuki reaction as the starting material, and intermediate A-25-2 was obtained by recrystallization from toluene. (Y = 66.2%)

c) Synthesis of intermediate A-25-3

Intermediate A-25-2 was synthesized / purified by using borylation as starting material for intermediate A-1-3, to obtain intermediate A-25-3. (Y = 98.0%)

d) Synthesis of Compound A-25

Intermediate A-25-3 and 2-chloro-4,6-diphenyl-1,3,5-triazine were synthesized using Suzuki reaction as starting materials, 2-dichlorobenzene to obtain Compound A-25. (Y = 58.3%)

Synthetic example  4: Synthesis of Compound A-49

[Reaction Scheme 4]

a) Synthesis of Compound A-49

Intermediate A-1-3 and 2-chloro-4,6-diphenyl-1,3,5-triazine were synthesized using Suzuki reaction as starting materials, 2-dichlorobenzene to obtain Compound A-49. (Y = 60.1%)

Synthetic example  5: Synthesis of Compound A-56

[Reaction Scheme 5]

a) Synthesis of intermediate A-56-1

2,4-dichloro-6-phenyl-1,3,5-triazine and 3-dibenzothienylboronic acid were synthesized by Suzuki reaction as in the synthesis of Intermediate A-1-1 and recrystallized from toluene Intermediate A-56-1 was obtained. (Y = 43.7%)

b) Synthesis of Compound A-56

Intermediate A-56-1 and Intermediate A-1-3 were synthesized using Suzuki reaction as a starting material and intermediate A-1-1, and recrystallized from 1,2-dichlorobenzene to obtain Compound A-56 . (Y = 87.0%)

Synthetic example  6: Synthesis of Compound A-74

[Reaction Scheme 6]

a) Synthesis of intermediate A-74-1

Intermediate A-17-1 and 3-biphenylboronic acid were synthesized by Suzuki reaction as in the synthesis example of intermediate A-1-1, and recrystallized from toluene to obtain intermediate A-74-1. (Y = 55.5%)

b) Synthesis of intermediate A-74-2

4-chloro-2,6-diphenylpyrimidine and 4-chlorophenylboronic acid were synthesized by the Suzuki reaction as in the synthesis example of intermediate A-1-1, and recrystallized from chlorobenzene to obtain intermediate A-74-2 . (Y = 51.7%)

c) Synthesis of intermediate A-74-3

Intermediate A-74-2 was synthesized / purified by using borylation as starting material for intermediate A-1-3, to obtain intermediate A-74-3. (Y = 77.1%)

d) Synthesis of Compound A-74

Intermediate A-74-1 and Intermediate A-74-3 were synthesized by Suzuki reaction as in the synthesis example of Intermediate A-1-1, and recrystallized from 1,2-dichlorobenzene to obtain Compound A-74 . (Y = 65.3%)

Synthetic example  7: Synthesis of Compound A-77

[Reaction Scheme 7]

a) Synthesis of intermediate A-77-1

4,6-dichloro-2-phenylpyrimidine and 3-dibenzofuranyl boronic acid were synthesized by Suzuki reaction as in the synthesis example of intermediate A-1-1, and recrystallized from a dichloromethane: n- hexane mixed solution. A-77-1 was obtained. (Y = 56.3%)

b) Synthesis of intermediate A-77-2

Intermediate A-77-1 and 4-chlorophenylboronic acid were synthesized using the Suzuki reaction as a starting material, and intermediate A-77-2 was obtained by recrystallization from toluene. (Y = 67.9%)

c) Synthesis of intermediate A-77-3

Intermediate A-77-2 was synthesized / purified by using borylation as starting material for intermediate A-1-3, to obtain intermediate A-77-3. (Y = 70.6%)

d) Synthesis of Compound A-77

Intermediate A-77-3 and 2-chloro-4,6-diphenyl-1,3,5-triazine were synthesized using Suzuki reaction as starting materials, 2-dichlorobenzene to obtain Compound A-77. (Y = 74.4%)

Reference Synthetic example  1: Synthesis of Compound C-1

[Reaction Scheme 8]

a) Synthesis of intermediate C-1-1

Synthesis / purification of Intermediate C-1-1 (2-bromophenyl) -4,6-diphenyl-1,3,5-triazine was carried out using borylation as in Synthesis Example of Intermediate A- ≪ / RTI > (Y = 47.2%)

d) Synthesis of Compound C-1

Intermediate C-1-1 and Intermediate A-1-1 were synthesized by the Suzuki reaction as in Synthesis Example of Intermediate A-1-1, and recrystallized from 1,2-dichlorobenzene to obtain Compound C-1 . (Y = 72.6%)

Synthesis of Comparative Compounds 1 to 8

[Comparative Compound 1] [Comparative Compound 2] [Comparative Compound 3]

[Comparative Compound 4] [Comparative Compound 5] [Comparative Compound 6]

The compounds of Comparative Compounds 1 to 6 were synthesized by referring to Patent Document 10-2016-0150000.

[Comparative Compound 7] [Comparative Compound 8]

The comparative compounds 7 and 8 were synthesized by referring to the registered patent 10-1387738.

(Synthesis of compound for second organic optoelectronic device)

Synthetic example  8: Synthesis of Compound B-15

[Reaction Scheme 9]

a) Synthesis of compound B-15

1 equivalent of intermediate 5,7-dihydro-5-phenylindolo [2,3-b] carbazole (CAS No. 1448296-00-1) and 3- (4-bromophenyl) -9-phenylcarbazole (CAS No. 1028647-93 -9) to one equivalent of sodium t -butoxide, and 2 equivalents of Pd ₂ (dba) ₃ and then 0.05 equivalents was suspended so that the 0.2 M in xylene tri- t -butylphosphine placed 0.15 equivalents was stirred under reflux for 18 hours. 1.5 times of methyl alcohol was added to the reaction mixture, and the resulting solid was filtered and washed with 300 mL of water. The solid was recrystallized using chlorobenzene to obtain compound B-15 in a yield of 66%.

Synthetic example  9: Synthesis of Compound B-55

[Reaction Scheme 10]

a) Synthesis of compound B-55

1 equivalent of intermediate 5,8-dihydro-5-phenylindolo [2,3-c] carbazole (CAS No: 1637752-63-6) and 3- (4-bromophenyl) -9-phenylcarbazole (CAS No. 1028647-93 -9) to one equivalent of sodium t -butoxide, and 2 equivalents of Pd ₂ (dba) ₃ and then 0.05 equivalents was suspended so that the 0.2 M in xylene tri- t -butylphosphine placed 0.15 equivalents was stirred under reflux for 18 hours. 1.5 times of methyl alcohol was added to the reaction mixture, and the resulting solid was filtered and washed with 300 mL of water. The solid was recrystallized using chlorobenzene to obtain Compound B-55 in a yield of 54%.

Synthetic example  10: Synthesis of Compound B-66

[Reaction Scheme 11]

a) Synthesis of compound B-66

1 equivalent of intermediate 5,11-dihydro-5-phenylindolo [3,2-b] carbazole (CAS No. 1316311-27-9) and 3-bromo-9-phenylcarbazole (CAS No. 1153-85-1) the equivalent sodium t -butoxide, and 2 equivalents of Pd ₂ (dba) ₃ and then 0.05 equivalents was suspended so that the 0.2 M in xylene tri- t -butylphosphine placed 0.15 equivalents was stirred under reflux for 18 hours. 1.5 times of methyl alcohol was added to the reaction mixture, and the resulting solid was filtered and washed with 300 mL of water. The solid was recrystallized from 1,2-dichlorobenzene to obtain Compound B-66 in 72% yield.

Synthetic example  11: Synthesis of compound B-84

[Reaction Scheme 12]

a) Synthesis of compound B-84

One equivalent of intermediate 5-phenyl-12H-indolo [3,2-c] carbazole (CAS No. 1247053-55-9) and 3- (4-bromophenyl) -9-phenylcarbazole (CAS No. 1028647-93-9 ), 1 equivalent of sodium t -butoxide, and 2 equivalents of Pd ₂ (dba) ₃ and then 0.05 equivalents was suspended so that the 0.2 M in xylene tri- t -butylphosphine placed 0.15 equivalents was stirred under reflux for 18 hours. 1.5 times of methyl alcohol was added to the reaction mixture, and the resulting solid was filtered and washed with 300 mL of water. The solid was recrystallized using chlorobenzene to obtain Compound B-84 in a yield of 85%.

Evaluation 1: Energy simulation comparison

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) Simulation 1 C-1 -6.12 -2.01 2.762 3.680 Simulation 2 A-1 -6.06 -2.05 2.693 3.589 Simulation 3 A-25 -6.06 -2.05 2.686 3.658 Simulation 4 A-49 -6.12 -2.29 2.722 3.449 Simulation 5 A-77 -6.04 -2.21 2.756 3.432

Referring to Table 1, low LUMO was observed in Simulations 2 to 5 as compared to Simulation 1. Compound A-1, Compound A-25 and Compound A-77 having a pyrimidine skeleton are more LUMO than Compound C-1, although compound C-1 commonly uses triazine lower in LUMO than pyrimidine Respectively. This result suggests that the interconnection between the ET cores can enhance the influence and have a fast electron transport capability.

(Preparation of organic light emitting device I: host composition)

Example  One

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å 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. Compound A was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a hole injection layer having a thickness of 700 A and Compound B was deposited on the injection layer to a thickness of 50 ANGSTROM, To form a hole transporting layer. (2-phenylpyridine) iridium (III) [Ir (ppy) ₃ ] was doped to 10% by weight on the hole transport layer using the compound A-1 and the compound B- A 400 Å thick light emitting layer was formed by vapor deposition. Here, the compound A-1 and the compound B-15 were used in a weight ratio of 3: 7, and the ratio was separately described in the following examples. Subsequently, Compound D and Liq were simultaneously vacuum-deposited on the light emitting layer at a ratio of 1: 1 to form an electron transport layer having a thickness of 300 Å. Liq 15 Å and Al 1200 Å were sequentially vacuum deposited on the electron transport layer to form a cathode, Respectively.

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

Ir (ppy) ₃ = 27 wt%: 63 wt%: 10 wt%] (400 Å) / EML [Compound A-1: B- Compound D: Liq (300 Å) / Liq (15 Å) / Al (1200 Å).

Compound A: N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-

Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),

Compound C: N- (biphenyl-4-yl) -9,9-dimethyl- N- (4- (9-phenyl-9H-carbazol-

Compound D: 8- (4- (4,6-di (naphthalen-2-yl) -1,3,5-triazin- 2- yl) phenyl) quinoline

Example  2 to Example  6, and Comparative Example  1 to Comparative Example  6

Examples 2 to 6 and Comparative Examples 1 to 6 were prepared in the same manner as in Example 1 except that the first host and the second host were used as shown in Tables 2 and 3 below. The device was fabricated.

Evaluation 2: Luminescence efficiency and lifetime Synergistic effect  Confirm

The luminous efficiency, lifetime, and driving characteristics of the organic light emitting devices according to Examples 1 to 6 and Comparative Examples 1 to 6 were evaluated. The specific measurement method is as follows, and the results are shown in Tables 2 and 3.

(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) Measurement of driving voltage

The driving voltage of each device was measured at 15 mA / cm ² using a current-voltage meter (Keithley 2400). The results are shown in Table 1.

(5) Life measurement

Firing the polar Optronics device of life measured using the measurement system, for example from 1 to 10, Reference Example 1 and Comparative Examples 1 to 6 for the manufacture of organic light-emitting device at an initial luminance (cd / m ²⁾ as 5000cd / m ² And the decrease in luminance over time was measured, and the point at which the luminance was reduced to 90% of the initial luminance was measured as the T90 lifetime.

When the first host is a triazine-pyrimidine structure 1st
Host Second
Host The first host +
Second host
ratio color efficiency Vd life span Example 1 A-1 B-15 3: 7 green 67 3.5 300 Example 2 A-1 B-84 3: 7 green 69 3.4 330 Example 3 A-17 B-84 3: 7 green 67 3.3 350 Example 4 A-74 B-84 3: 7 green 68 3.4 350 Comparative Example 1 Comparative compound 1 B-84 3: 7 green 66 3.7 230 Comparative Example 2 Comparative compound 2 B-84 3: 7 green 66 3.8 240 Comparative Example 4 A-1 Comparative compound 4 3: 7 green 63 3.9 180 Comparative Example 5 A-1 Comparative compound 5 3: 7 green 63 3.8 220 Comparative Example 6 A-1 Comparative compound 6 3: 7 green 64 3.8 220

When the first host is a triazine-triazine structure 1st
Host Second
Host The first host +
Second host
ratio color efficiency Vd life span Example 5 A-49 B-84 3: 7 green 67 3.25 450 Example 6 A-56 B-84 3: 7 green 68 3.2 480 Comparative Example 3 Comparative compound 3 B-84 3: 7 green 66 3.3 300

Referring to Table 2 and Table 3, in Examples 1 to 4 using the first host and the second host according to the present invention and Comparative Examples 1 and 2 of the mixed host using the same second host respectively, 2, and Comparative Example 3, it was confirmed that the effect of lowering the driving voltage, the lifetime thereof was remarkably increased, and the efficiency was slightly increased.

In Examples 1 to 4, in which the second host was indolocarbazyl, the driving voltage was significantly reduced and the lifetime characteristics were better than those of Comparative Examples 4 to 6 in which the second host was made of biscarbazoles. It is believed that this is due to the well-balanced balance of the hole transport capability of the first host and the second host, which have relatively good electron transport capability.

When the ET moiety linkage from the device data is unfolded to para, the conjugation between the meta linkage to the ET moiety is enhanced to lower the LUMO and the dibenzofuran and dibenzothiophene are directly linked to the ET moiety, It can be seen that the driving voltage in the device of the material is lowered and the lifetime is increased through the fusion effect of the extension and the ring.

(Fabrication of organic light emitting device II: Electron transport layer )

Example  7

As the anode, ITO was used in a thickness of 1000 Å, and as a cathode, aluminum (Al) was used in a thickness of 1000 Å.

Specifically, the manufacturing method of the organic photoelectric device will be described. An 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 cut in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 5 minutes each, UV ozone cleaning was performed for 30 minutes.

On the glass substrate, an N ¹ , N ^{1 '} - (biphenyl-4,4'-diyl) bis (N ¹ - (naphthalene-2-yl) -N ⁴ , N ⁴ -diphenylbenzene- 1,4-diamine) was deposited on the hole transport layer. Subsequently, 40 nm of N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine (NPB) was deposited as a hole transport layer.

5% of N, N, N ', N'-tetrakis (3,4-dimethylphenyl) Phenyl) -10- (naphthalen-2-yl) anthracene (fluorescent blue host) was deposited to a thickness of 25 nm.

Subsequently, 35 nm of Compound A-1 prepared in Synthesis Example 1 was deposited as an electron transporting layer.

Liq as an electron injecting layer was vacuum deposited on the electron transporting layer to a thickness of 0.5 nm, and Al was vacuum-deposited to a thickness of 100 nm to form a Liq / Al electrode. The structure of the manufactured organic photoelectric device is as shown in FIG.

Example  8 - Example  13, Reference example  One, Comparative Example  7 and 8

The devices of Examples 8 to 13, Reference Example 1, and Comparative Examples 7 and 8 were fabricated in the same manner as in Example 7 except that the first host was used in the electron transport layer as shown in Table 4 below.

Evaluation 3: Luminescence efficiency and lifetime Synergistic effect  Confirm

The luminous efficiency and driving characteristics of the organic light emitting devices according to Examples 7 to 13, Reference Example 1, and Comparative Examples 7 and 8 were evaluated. The specific measurement method is as follows, and the results are shown in Table 4.

(1) Measurement of luminous efficiency

The luminous efficiency was calculated in the same manner as in Evaluation 2.

(2) Measurement of driving voltage

The driving voltage of each device was measured at 10 mA / cm ² using a current-voltage meter (Keithley 2400).

(3) Life measurement

It performed using polar Optronics lifetime measuring system for the manufacture of organic light emitting device Example 7 to Example 13, Reference Example 1 and Comparative Example 7 and the light emitting elements 8 to the initial luminance (cd / m ²⁾ to 750cd / m ² And the decrease in luminance over time was measured, and the time point at which the luminance was reduced to 97% of the initial luminance was measured as T97 lifetime.

Electron transport layer element effect Electron transport layer efficiency Vd life span Example 7 A-1: LiQ 14 3.5 250 Example 8 A-17: LiQ 13 3.4 285 Example 9 A-25: LiQ 15 3.8 270 Example 10 A-49: LiQ 14 3.3 380 Example 11 A-56: LiQ 14 3.2 400 Example 12 A-74: LiQ 15 3.5 270 Example 13 A-77: LiQ 14 3.5 220 Reference Example 1 C-1: LiQ 12 3.5 134 Comparative Example 7 Comparative Compound 7: LiQ 11 4.0 210 Comparative Example 8 Comparative compound 8: LiQ 12 3.9 180

Referring to Table 4, it was confirmed that Examples 7 to 13 using the first host according to the present invention had an effect of increasing the efficiency and lifetime compared to Reference Example 1 in which a compound in which ET moieties are linked by metaphenylene , And 3-dibenzofuran (or 3-dibenzothiophene) are directly connected to the ET unit, the increase in the efficiency and life span of Comparative Examples 7 and 8, which do not include such a moiety, And the driving voltage is also 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, 500: organic light emitting device
105: organic layer 130: light emitting layer
110: cathode 120: anode
140: hole assist layer
150: electron transport layer 160: electron injection layer
170: Hole injection layer

Claims (15)

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

In Formula 1,
Z ¹ to Z ⁶ are each independently N or CR ^c ,
At least two of Z ¹ to Z ³ are N,
At least two of Z ⁴ to Z ⁶ are N,
R ¹ to R ³ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R ^a , R ^b and R ^c are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
X is O or S; The method according to claim 1,
A compound for a first organic optoelectronic device represented by any of the following Formulas 1-1 to 1-4:
[Formula 1-1] [Formula 1-2] [Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
R ¹ to R ³ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R ^a and R ^b are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
X is O or S; The method according to claim 1,
Each of R ¹ to R ³ is independently a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
Wherein R ^a , R ^b and R ^c are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C4 alkyl groups, or substituted or unsubstituted C6 to C12 aryl groups. The method of claim 3,
Wherein R ¹ to R ³ are each independently selected from the substituents listed in the following Group I:
[Group I]

In the above group I, * is a connection point. The method according to claim 1,
A compound for a first organic optoelectronic device, which is one of the compounds listed in the following Group 1:
[Group 1]
[A-1] [A-2] [A-3] [A-4]

[A-5] [A-6] [A-7] [A-8]

[A-9] [A-10] [A-11] [A-12]

[A-13] [A-14] [A-15] [A-16]

[A-17] [A-18] [A-19] [A-20]

[A-21] [A-22] [A-23] [A-24]

[A-25] [A-26] [A-27] [A-28]

[A-29] [A-30] [A-31] [A-32]

[A-33] [A-34] [A-35] [A-36]

[A-37] [A-38] [A-39] [A-40]

[A-41] [A-42] [A-43] [A-44]

[A-45] [A-46] [A-47] [A-48]

[A-49] [A-50] [A-51] [A-52]

[A-53] [A-54] [A-55] [A-56]

[A-57] [A-58] [A-59] [A-60]

[A-61] [A-62] [A-63] [A-64]

[A-65] [A-66] [A-67] [A-68]

[A-69] [A-70] [A-71] [A-72]

[A-73] [A-74] [A-75] [A-76]

[A-77] [A-78] [A-79] [A-80]

[A-81] [A-82] [A-83] [A-84]

[A-85] [A-86] [A-87] [A-88]

[A-89] [A-90] [A-91] [A-92]

. A first organic optoelectronic device compound according to claim 1; And
A composition for an organic optoelectronic device comprising a compound for a second organic optoelectronic device comprising a combination of a moiety represented by the following formula (2) and a moiety represented by the following formula (3)
[Chemical Formula 2] < EMI ID =

In the above Formulas 2 and 3,
Y ¹ and Y ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
The adjacent two * in the above formula (2) are connected with two * in the above formula (3) to form a fused ring. In the above formula (2), * without the fused ring is independently CL ^a -R ^d ,
R ^d and R ⁴ to R ⁷ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, Or a combination thereof,
L ^a , 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 method according to claim 6,
Wherein the compound for a second organic optoelectronic device is represented by the following formula (2A) or (2D):
[Chemical Formula 2A]

In the above Chemical Formulas 2A and 2D,
Y ¹ and Y ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R ^d1 , R ^d4 and R ^d5 and R ⁴ to R ⁷ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, C30 heterocyclic group, or a combination thereof,
L ^a1 , L ^a6 , 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 method according to claim 6,
Y ¹ and Y ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzo A furanyl group, or a substituted or unsubstituted dibenzothiophen yl group. 9. The method of claim 8,
Wherein Y ¹ and Y ² are each independently selected from the substituents listed in the following Group II:
[Group II]

In the group II,
* Are the connection points with L ¹ and L ² , respectively. The method according to claim 6,
The compound for a first organic optoelectronic device is represented by the following general formula (1-1) or (1-4)
Wherein the compound for a second organic optoelectronic device is represented by the following formula (2A) or (2D):
[Formula 1-1] [Formula 1-4]

In Formulas 1-1 and 1-4,
R ¹ to R ³ are each independently a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
R ^a and R ^b are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C4 alkyl group, or substituted or unsubstituted C6 to C12 aryl group,
X is O or S;
[Chemical Formula 2A]

In the above Chemical Formulas 2A and 2D,
Y ¹ and Y ² each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzo A furanyl group, or a substituted or unsubstituted dibenzothiophenyl group,
R ^d1 , R ^d4 , R ^d5 and R ⁴ to R ⁷ are each independently hydrogen, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group ego,
L ^a1 , L ^a4 , L ^a5 , L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group. The method according to claim 6,
Wherein the compound for a first organic optoelectronic device is represented by the following Formula 1-3,
Wherein the compound for the second organic optoelectronic device is represented by the following Formula (2): < EMI ID =
[Formula 1-3]

In Formula 1-3,
R ¹ to R ³ are each independently a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
R ^a and R ^b are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C4 alkyl group, or substituted or unsubstituted C6 to C12 aryl group,
X is O or S;
[Chemical Formula 2]

In Formula (2D) above,
Y ¹ and Y ² each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzo A furanyl group, or a substituted or unsubstituted dibenzothiophenyl group,
R ^d4 , R ^d5 and R ⁴ to R ⁷ are each independently hydrogen, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
L ^a4 , L ^a5 , L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group. Positive and negative facing each other, and
And at least one organic layer positioned between the anode and the cathode,
An organic optoelectronic device comprising the compound for an organic optoelectronic device according to any one of claims 1 to 5 or the composition for an organic optoelectronic device according to any one of claims 6 to 11. 13. The method of claim 12,
Wherein the organic layer includes an auxiliary layer including at least one of a hole injecting layer, a hole transporting layer, an electron injecting layer and an electron transporting layer, and a light emitting layer,
Wherein the auxiliary layer comprises the compound for an organic optoelectronic device. 14. The method of claim 13,
And a composition for the organic opto-electronic device as a host of the light-emitting layer. 13. A display device comprising the organic opto-electronic device according to claim 12.

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