KR20190038109A - 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 an organic optoelectronic element and a display device using: a compound for a first organic optoelectronic element represented by a combination of chemical formula 1 and chemical formula 2; and a composition for an organic optoelectronic element device including the compound for the first organic optoelectronic element and the compound for the second organic optoelectronic element represented by chemical formula 3. The details of chemical formulas 1 to 3 are as defined in the specification.

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 a combination of the following formulas (1) and (2).

[Chemical Formula 1] < EMI ID =

In the above formulas (1) and (2)

* Is a connecting point of formulas (1) and (2)

Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,

Ar ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group,

R ¹ to R ⁴ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,

L ⁴ is a single bond or a substituted or unsubstituted C6 to C20 arylene group

The total number of carbon atoms in " -L ⁴ -Ar ² " is 16 to 50.

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

(3)

In Formula 3,

X < ¹ > is O or S,

Z ¹ to Z ³ are each independently N or CR ^a ,

At least two of Z ¹ to Z ³ are N,

L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

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

At least one of A ¹ and A ² is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ⁵ to R ⁷ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.

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 and 2 are cross-sectional views illustrating an organic light emitting device according to one 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- , A 9-carbazolyl group, a 1-dibenzofuranyl group, a 2-dibenzofuranyl group, a 3-dibenzofuranyl group, a 4-dibenzofuransulfinyl group, a 1-dibenzothiophenyl group, , 3-dibenzothiophen yl group or 4-dibenzothiophen yl 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 a C1 to C30 alkyl group. 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 an embodiment may be represented by a combination of the following formulas (1) and (2).

[Chemical Formula 1] < EMI ID =

In the above formulas (1) and (2)

* Is a connecting point of formulas (1) and (2)

Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,

Ar ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group,

R ¹ to R ⁴ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,

L ⁴ is a single bond or a substituted or unsubstituted C6 to C20 arylene group;

The total number of carbon atoms in " -L ⁴ -Ar ² " is 16 to 50.

For example, L ⁴ may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthylene group (divalent naphthalene linking group).

For example, L < ⁴ > may be a single bond or a linking group selected from the group I below.

[Group I]

In said group I,

R ¹⁰ to R ¹³ are each independently a hydrogen atom or a substituted or unsubstituted C6 to C20 aryl group,

The R ¹⁰ to R ¹³ may be independently present, or the R ¹⁰ and R ¹¹ or the R ¹² and R ¹³ may bond to each other to form a fused ring.

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

The compound for a first organic optoelectronic device according to the present invention is a symmetric structure, which induces excellent packing between molecules by using an indolocarbazole core having a large planarity, and has at least one linear ) Terphenyl-containing aryl group, it has excellent hole transporting properties and appropriately overlaps with the absorption spectrum of the dopant applied together, so that it is effective in improving the efficiency of the organic optoelectronic device using the compound.

Particularly, since the N-substituent of indolocarbazole becomes a general aryl group which makes complete conjugation, the heat stability of the substituent having an aliphatic hydrocarbon, such as fluorenyl group, is excellent.

The compound for a first organic optoelectronic device may be represented by any one selected from the group consisting of the following formulas (1A) to (1A '' ') and (1B to 1B' '' .

[Chemical Formula 1B]

≪ RTI ID = 0.0 > 1A ') < / RTI &

&Quot; (1) "

≪ RTI ID = 0.0 > 1A '"

In the above Chemical Formulas 1A to 1 '''and 1B to 1B''', Ar ¹ , Ar ² , and R ¹ to R ⁴ are as defined above, and R ¹⁴ and R ¹⁵ are each independently hydrogen Atom or a substituted or unsubstituted C6 to C20 aryl group,

R ¹⁴ and R ¹⁵ are each independently present or may combine with each other to form a fused ring.

The indolecarbazole core of the formula (1A) and (1B) has a structure of a rod type (bar type) compared to other indolecarbazole moieties and at the same time has a symmetrical property and can be packed well. In addition, since the aryl group of more than terphenyl in the N-substituted position assists the packing in comparison with the aryl group below biphenyl, the hole flow can be increased and the refractive index can be improved to increase the efficiency.

In one embodiment of the present invention, the formula (1A) may be represented by any one of the following formulas (1A-1) to (1A-3), and the formula (1B) may be represented by any one of the following formulas have.

[Chemical Formula 1A-1] [Chemical Formula 1A-2] [Chemical Formula 1A-3]

[Chemical Formula 1B-1] [Chemical Formula 1B-2] [Chemical Formula 1B-3]

In the above formulas (1A-1) to (1A-3) and (1B-1) to (1B-3), Ar ¹ , Ar ² and R ¹ to R ⁴ are as defined above, and R ¹⁴ and R ¹⁵ are each independently Is a hydrogen atom or a substituted or unsubstituted C6 to C20 aryl group,

R ¹⁴ and R ¹⁵ are each independently present or may combine with each other to form a fused ring.

In a specific embodiment of the present invention, the compound for the first organic optoelectronic device can be represented by the formula (1A-1) or (1B-1).

In a more specific embodiment of the present invention, Ar ¹ may be an unsubstituted phenyl group, an unsubstituted biphenyl group or an unsubstituted naphthyl group.

In a more specific embodiment of the present invention, Ar ¹ may be a C6 to C16 aryl group. In addition, Ar ² may be selected from the substituents listed in Group II below.

[Group II]

Each of R ¹ to R ⁴ may independently be a hydrogen atom.

The compound for the first organic optoelectronic device represented by the combination of the above-mentioned formulas (1) and (2) can be selected from, for example, 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]

[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-32]

[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]

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 compound for the second organic optoelectronic device may be represented by the following formula (3).

(3)

In Formula 3,

X < ¹ > is O or S,

Z ¹ to Z ³ are each independently N or CR ^a ,

At least two of Z ¹ to Z ³ are N,

L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

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

At least one of A ¹ and A ² is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ⁵ to R ⁷ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.

Means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group. In one example of the present invention, the "substitution" in the above formulas (2) and (3) means that at least one hydrogen is substituted with deuterium, C1 to C4 alkyl group, C6 to C12 aryl group or C2 to C12 heteroaryl group. In one specific example of the present invention, the "substitution" in the above-mentioned formulas (2) and (3) means that at least one hydrogen atom is replaced by a substituent selected from the group consisting of deuterium, a phenyl group, a meta-biphenyl group, a para-biphenyl group, a naphthyl group, A pyrimidinyl group, or a triazinyl group.

The compound for the second organic optoelectronic device includes a structure in which dibenzofuran (or dibenzothiophene) is bonded to a triazine or a pyrimidine moiety to increase the electron injection rate through expansion of the LUMO and planarity expansion of the ET moiety . In particular, when used in the light emitting layer together with the compound for the first organic optoelectronic device, the charge is balanced in the light emitting layer, thereby realizing a long-life organic light emitting device.

In one embodiment of the present invention, all of Z ¹ to Z ³ in Formula 3 may be N.

In one embodiment of the present invention, R ⁵ to R ⁷ in Formula 3 may each independently be hydrogen or a phenyl group.

In one embodiment of the present invention, A ¹ and A ² in Formula 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and A ¹ and Lt; ² > is a substituted or unsubstituted C6 to C30 aryl group.

In a specific embodiment of the present invention, A ¹ is a substituted or unsubstituted C6 to C30 aryl group, and A ² is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 hetero Can be a ring.

In a more specific embodiment of the present invention, A ¹ may be a substituted or unsubstituted C6 to C20 aryl group, and A ¹ is, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, A substituted terphenyl group, a substituted or unsubstituted quaterphenyl group, or a substituted or unsubstituted naphthyl group, and the formula 3 may be represented by the following formula 3-1.

[Formula 3-I]

In the above formula 3-1, X ¹ , Z ¹ to Z ³ , L ¹ to L ³ , A ² , and R ⁵ to R ⁷ are as defined above, and R ⁸ and R ⁹ are defined as R ⁵ to R < ⁷ >

A ¹ in the above formula (3) may be selected from the substituents listed in the following Group III, for example.

[Group III]

In the above group III, * is a connection point with L ² .

A ² in Formula 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, An unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group,

In particular, it may be represented by any of the following formulas (3-1-1) to (3-3-3-3) depending on the specific type of A ² .

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

X ¹ , Z ¹ to Z ³ , L ¹ to L ³ , and R ⁵ to R ⁸ are as defined above, and X ² is the same as defined above for X ¹ , Z ⁴ to Z ⁶ have the same definitions as Z ¹ to Z ³ described above, and the definitions of R ^b , R ^c and R ^d are the same as those of R ⁵ to R ⁸ described above.

Ar ³ in the above formula (3-1-1) may be a substituted or unsubstituted C6-C20 aryl group, specifically a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group , A substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quaterphenyl group, wherein the additional substituent may be deuterium, cyano group, phenyl group, or naphthyl group.

In one specific embodiment of the present invention, R ^b and R ^c in formula (3-1-3) each independently represent a substituted or unsubstituted C6 to C20 aryl group, and more specifically, a phenyl group, a biphenyl group, a naphthyl group, Phenyl group.

A ² in the formula (3) may be selected from the substituents listed in the following group IV, for example.

[Group IV]

In the above group IV, * is a connection point with L ³ .

In the most specific embodiment of the present invention, the compound for the second organic optoelectronic device can be represented by the formula (3-1-1) or (3-1-2), wherein R ⁸ and R ⁹ are, for example, Ar ³ in the formula (3-1-1) may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted aliphatic group X ² in Formula 3-I-2 is O or S, and R ^b , R ^c and R ^d are each independently hydrogen, deuterium, cyano or phenyl.

(3-I) is represented by any one of the following formulas (III-A), (III-IB), (III-III) and (III-D) depending on the specific substitution position of the dibenzofuranyl group (or dibenzothiophen yl group) .

[Chemical Formula 3-IA] [Chemical Formula 3-IB]

[Chemical formula 3-1C] [Chemical formula 3-1D]

In the above formulas 3-1A to 3-1D, definitions of X ¹ , Z ¹ to Z ³ , L ¹ to L ³ , R ⁵ to R ⁹ and A ² are as described above.

In one specific embodiment of the present invention, the formula (3-1) may be represented by the formula (3-1B). In a more specific embodiment, the formula (3-1B) IB-3. ≪ / RTI >

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

[Formula 3-IB-3]

X ¹ and X ² , Z ¹ to Z ⁶ , L ¹ to L ³ , Ar ³ , R ^b , R ^c and R ^d and R ⁵ to R ^{6 in} the general formulas 3-1B-1 to 3-1B- The definition of ⁹ is as described above.

In a more specific embodiment, the above-mentioned formula (3-IB-1) or (3-IB-2) is preferable.

In a specific embodiment, R ^b and R ^c in Formula 3-IB-3 of the present invention may be independently a substituted or unsubstituted C6 to C20 aryl group, and more specifically, a phenyl group, a biphenyl group, a naphthyl group, . In a most specific embodiment of the present invention, each of L ¹ to L ³ independently represents 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 naphthylenylene group, and may be selected from, for example, a linking group listed in the following group V.

[Group V]

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

In a more specific embodiment, each of L ¹ to L ³ may independently be a single bond or an unsubstituted phenylene group. More specifically, L < ^{1 >} may be a single bond or an unsubstituted phenylene group, but a single bond is more preferable. In a more specific embodiment of the present invention, the formula (3-1-1) may be represented by the following formula (3-1-1a) or (3--1-1b)

[Formula 3-I-1a] [Formula 3-I-1b]

The formula (3-I-2) may be represented by the following formula (3-1-2a)

[Formula 3-I-2a]

(3-I-3), (3-I-3), (3-I-3b) 3f. ≪ / RTI >

[Formula 3-I-3a] [Formula 3-I-3b] [Formula 3-I-3c]

[Formula 3-I-3d] [Formula 3-I-3e] [Formula 3-I-3f]

In Formula 3-I-1a, Formula 3-I-1b, Formula 3-I-2a and Formula 3-I-3a to Formula 3-I-3f, Ar ³ , X ¹ , L ¹ to L ³ , R ^b , R ^c , R ^d and R ⁵ to R ⁹ are as defined above.

For example, R ⁵ to R ⁷ in each of the above-mentioned formulas 3-I-1a, 3-I-1b, 3-I-2a and 3-1- R ⁸ and R ⁹ may each independently be hydrogen, deuterium, a phenyl group, a biphenyl group, or a terphenyl group, more preferably R ⁵ to R ⁷ are all hydrogen, and R ⁸ and R ⁹ may each independently be hydrogen, a phenyl group, or a biphenyl group.

The nitrogen-containing six-membered ring represented by Z ¹ to Z ³ in the above formula (3) may be a pyrimidinyl group or a triazinyl group, more preferably a triazinyl group.

In a specific embodiment of the present invention, the compound for a second organic optoelectronic device may be represented by, for example, the formula 3-1-1 or 3--1-2, May be represented by the general formulas (III-I-1b) and (III-I-2a).

The compound for a second organic optoelectronic device may be represented by, for example, the formula 3-IB and more preferably the formula 3-IB-1 or the formula 3-IB-2.

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

[Group 2]

[C-1] [C-2] [C-3] [C-4]

[C-5] [C-6] [C-7] [C-8]

[C-9] [C-10] [C-11] [C-12]

[C-13] [C-14] [C-15] [C-16]

[C-17] [C-18] [C-19] [C-20]

[D-1] [D-2] [D-3] [D-4]

[D-5] [D-6] [D-7] [D-8]

[D-9] [D-10] [D-11] [D-12]

[D-13] [D-14] [D-15] [D-16]

[D-17] [D-18] [D-19] [D-20]

[D-21] [D-22] [D-23] [D-24]

[D-25] [D-26] [D-27] [D-28]

[D-29] [D-30] [D-31] [D-32]

[D-33] [D-34] [D-35] [D-36]

[D-37] [D-38] [D-39] [D-40]

[D-41] [D-42] [D-43] [D-44]

[D-45] [D-46] [D-47] [D-48]

[D-49] [D-50] [D-51] [D-52]

[D-53] [D-54] [D-55] [D-56]

[D-57] [D-58] [D-59] [D-60]

[D-61] [D-62] [D-63] [D-64]

[D-65] [D-66] [D-67] [D-68]

[D-69] [D-70] [D-71] [D-72]

[D-73] [D-74] [D-75] [D-76]

[D-77] [D-78] [D-79] [D-80]

[D-81] [D-82] [D-83] [D-84]

[D-85] [D-86] [D-87] [D-88]

[D-89] [D-90] [D-91] [D-92]

[D-93] [D-94] [D-95] [D-96]

[D-97] [D-98] [D-99] [D-100]

[D-101] [D-102] [D-103] [D-104]

[D-105] [D-106] [D-107] [D-108]

[D-109] [D-110] [D-111] [D-112]

[D-113] [D-114] [D-115] [D-116]

[D-117] [D-118] [D-119] [D-120]

[D-121] [D-122] [D-123] [D-124]

[D-125] [D-126] [D-127] [D-128]

[E-1] [E-2] [E-3] [E-4]

[E-5] [E-6] [E-7] [E-8]

[E-9] [E-10] [E-11] [E-12]

[E-13] [E-14] [E-15] [E-16]

[E-17] [E-18] [E-19] [E-20]

[F-1] [F-2] [F-3] [F-4]

[F-5] [F-6] [F-7] [F-8]

[F-9] [F-10] [F-11] [F-12]

[F-13] [F-14] [F-15] [F-16]

[F-17] [F-18] [F-19] [F-20]

[F-21] [F-22] [F-23] [F-24]

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 composition according to one embodiment of the present invention comprises a compound represented by the formula (1A-1) or (1B-1) as a compound for a first organic optoelectronic device, Wherein Ar ¹ and Ar ² in the above formulas 1A-1 and 1B-1 each independently represent an unsubstituted phenyl group, an unsubstituted biphenyl group Or an unsubstituted naphthyl group; and Ar ³ in the formula (3-1B-1) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, Or a substituted or unsubstituted quaterphenyl group. Other substituents are as defined above.

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 the first organic optoelectronic device and the compound for the second organic optoelectronic device may be included in the range of 1: 1 to 1: 4, and may be included in the range of 1: 1 to 3: 7.

For example, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be contained in the range 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.

The 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 a hole injection layer, a hole transport layer, An auxiliary layer including at least one of an electron injection layer and an electron transport layer, and a light emitting layer, and the light emitting layer may include the above-described compound for an organic optoelectronic device, or a composition for the organic optoelectronic device described above.

For example, in the compound for an organic optoelectronic device, the organic layer may be included in at least one auxiliary layer selected from a hole injection layer, a hole transport layer, and an electron blocking layer.

As another example, the composition for the organic optoelectronic device may be included as a host of the light emitting layer. For example, as a green host of the light emitting layer.

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 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.

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 the reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, Alfa-Aesar 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 A-1

[Reaction Scheme 1: Synthesis of A-1]

Synthetic example  1-a: Synthesis of A-1-1

2-bromo-9-phenylcarbazole (50.0 g, 155 mmol), 2-chloroaniline (24.3 g, 233 mmol), palladium (II) acetate (1.7 g, And tri-tert butylphosphine 50% solution (6.3 g, 16 mmol) were added to 500 mL of xylenes and refluxed under nitrogen stream for 12 hours. When the reaction was completed, all of the solvent was evaporated and purified by column chromatography with n- hexane: dichloromethane mixed solution to obtain A-1-1 (44.0 g, Y = 77%).

Synthetic example  1-b: Synthesis of A-1-2

(58.0 g, 179 mmol) and tricyclohexylphosphine tetrafluoroborate (8.8 g, 24 mmol) were added to a solution of 400 mL of dimethylacetamide (44.0 g, 119 mmol), palladium And the mixture was refluxed under nitrogen stream for 12 hours. When the reaction is complete, the solution is poured into water to precipitate a solid. The precipitated solid was filtered and purified by column chromatography with a mixed solution of n- hexane: dichloromethane to obtain A-1-2 (25.1 g, Y = 63%).

Synthetic example  1-c: Synthesis of A-1

A-1-2 (10.0 g, 30 mmol), 4-bromo- p -terphenyl (9.3 g, 30 mmol), bis (dibenzylideneacetone) palladium (0) (0.5 g, 1 mmol) and sodium tert-butoxide (4.3 g, 45 mmol) was dissolved in 150 mL of xylene, and then tri-tert-butylphosphine 50% solution (1.83 mL, 5 mmol) was slowly added thereto and refluxed under nitrogen gas stream for 12 hours. When the reaction was completed, all of the solvent was evaporated and recrystallized with chlorobenzene to obtain A-1 (10.6 g, Y = 63%).

Synthetic example  2: Synthesis of A-6

[Reaction Scheme 2: Synthesis of A-6]

Synthetic example  2-a: Synthesis of A-6-1

Synthesis was carried out as in Synthesis Example 1-a using 2-bromo-9- (4-biphenylyl) -carbazole as a starting material. (Y = 81%)

Synthetic example  2-b: Synthesis of A-6-2

Synthesis was conducted as in Synthesis Example 1-b, using A-6-1 as a starting material. (Y = 70%)

Synthetic example  2-c: 1- chloro -4- (3- biphenylyl ) Synthesis of benzene

4-chlorophenylboronic acid (30.0 g, 129 mmol), tetrakis (triphenylphosphine) palladium (0) (7.5 g, 6 mmol) and potassium carbonate (44.5 g, 322 mmol) L tetrahydrofuran: DIW = 2: 1 mixed solution, and the mixture was refluxed and stirred at 80 ° C for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. The residue was recrystallized from dichloromethane: n- hexane to obtain 26.1 g (Y = 77%) of 1-chloro-4- (3-biphenylyl) benzene.

Synthetic example  2-d: Synthesis of A-6

A-6-2 and 1-chloro-4- (3-biphenylyl) benzene as starting materials, the synthesis was carried out as in Synthesis Example 1-c. (Y = 74%)

Synthetic example  3: Synthesis of A-13

[Reaction Scheme 3: Synthesis of A-13]

The reaction methods of Synthesis Example 1-a, Synthesis Example 1-b, and Synthesis Example 1-c were sequentially applied except that 2-bromo-9- (2-naphthylyl) -carbazole was used as a starting material, A-13 was synthesized.

Synthetic example  4: A-21 synthesis

[Reaction Scheme 4: Synthesis of A-21]

Synthetic example  4-a: 2- [4- (4- klorophenyl ) phenyl] naphthalene Synthesis

4-chlorophenylboronic acid and 2-bromonaphthalene as starting materials, the synthesis was carried out as in Synthesis Example 2-c and recrystallized from chlorobenzene. (Y = 82%)

Synthetic example  4-b: Synthesis of A-21

Synthesis was carried out in the same manner as in Synthesis Example 1-c using 2- [4- (4-chlorophenyl) phenyl] naphthalene as a starting material and recrystallized from 1,2-dichlorobenzene. (Y = 77%)

Synthetic example  : A-34 synthesis

[Reaction Scheme 5: Synthesis of A-34]

Synthetic example  5-a: 2- bromo Synthesis of 6- (3-phenylphenyl) naphthalene

3-biphenylboronic acid and 2,6-dibromonaphthalene as starting materials, the synthesis was carried out as in Synthesis Example 2-c and recrystallized from 1,2-dichlorobenzene. (Y = 59%)

Synthetic example  5-b: Synthesis of A-34

Synthesis was carried out in the same manner as in Synthesis Example 1-c using 2-bromo-6- (3-phenylphenyl) naphthalene as a starting material and recrystallized from 1,2-dichlorobenzene. (Y = 71%)

Synthetic example  6: Synthesis of A-49

[Reaction Scheme 6: Synthesis of A-49]

Synthetic example  6-a: 4- chloro -1,1 ': Synthesis of 4', 1 '': 4 '', 1 '' '- quaterphenyl

Synthesis was carried out as in Synthesis Example 2-c using 4-bromo-p-terphenyl and 4-chlorophenylboronic acid as starting materials, and the product was recrystallized from 1,2-dichlorobenzene. (Y = 88%)

Synthetic example  6-b: Synthesis of A-49

Synthesis was carried out as in Synthesis Example 1-c using 4-chloro-1,1 ': 4', 1 "': 4" and 1 " , And 2-dichlorobenzene. (Y = 70%)

Synthetic example  7: Synthesis of B-1

[Reaction Scheme 7: Synthesis of B-1]

Synthetic example  7-a: Synthesis of B-1-1

Dissolve 3,3'-diindolylmethane (12 g, 50 mmol) and trimethyl orthoformate (8 mL) in 100 mL of methyl alcohol. Slowly drop 10 drops of sulfuric acid with a pipette and stir under reflux for 1 hour. When the reaction was completed, the resulting solid was filtered and washed with cold methyl alcohol to obtain B-1-1 (9.8 g, Y = 78%).

Synthetic example  7-b: Synthesis of B-1-2

Bromobenzene (6.0 g, 38 mmol), copper (I) iodide (1.46 g, 8 mmol), potassium carbonate (7.93 g, 57 mmol) and 1,10-phenanthroline (1.38 g, 8 mmol) were taken in 130 mL of N , N- dimethylformamide and refluxed under nitrogen stream for 12 hours. Once the reaction is complete, the solvent is evaporated and the residue is dissolved in toluene and filtered through silica gel. The filtered solution was directly recrystallized to obtain B-1-2 (7.2 g, Y = 57%).

Synthetic example  7-c: Synthesis of B-1

Synthesis was carried out as in Synthesis Example 1-c using B-1-2 and 4-bromo-p-terphenyl as starting materials, followed by recrystallization with 1,2-dichlorobenzene. (Y = 91%)

Synthetic example  8: Synthesis of B-5

[Reaction Scheme 8: Synthesis of B-5]

Synthetic example  8-a: Synthesis of B-5-1

Synthesis was carried out as in Synthesis Example 7-b using B-1-1 and 4-bromobiphenyl as starting materials, followed by recrystallization with chlorobenzene. (Y = 52%)

Synthetic example  8-b: Synthesis of B-5

Synthesis was conducted in the same manner as in Synthesis Example 1-c using B-5-1 and 4-bromo-p-terphenyl as starting materials and recrystallization with 1,2-dichlorobenzene once and recrystallization with N , N- dimethylformamide Respectively. (Y = 82%)

[Reaction formula 9: synthesis of B-13]

Synthetic example  9-a: Synthesis of B-13-1

Synthesis was conducted as in Synthesis Example 7-b using B-1-1 and 2-bromonaphthalene as starting materials, and the product was recrystallized from chlorobenzene. (Y = 54%)

Synthetic example  9-b: Synthesis of B-13

Synthesis was carried out as in Synthesis Example 1-c using B-13-1 and 4-bromo-p-terphenyl as starting materials, and recrystallization with 1,2-dichlorobenzene once and recrystallization with N , N- dimethylformamide Respectively. (Y = 80%)

[Reaction formula 10: synthesis of B-21]

Synthetic example  10: Synthesis of B-21

B-1-2 and 2- [4- (4-chlorophenyl) phenyl] proceeds the synthesized in the Synthesis Example 1-c to the naphthalene as the starting material, was recrystallized once with 1,2-dichlorobenzene, N, N - and recrystallized once with dimethylformamide. (Y = 83%)

[Reaction Scheme 11: Synthesis of B-33]

Synthetic example  11-a: 2- bromo Synthesis of 6- (4-phenylphenyl) naphthalene

4-biphenylboronic acid and 2,6-dibromonaphthalene as starting materials, the synthesis was carried out as in Synthesis Example 2-c and recrystallized from 1,2-dichlorobenzene. (Y = 66%)

Synthetic example  11-b: Synthesis of B-33

Synthesis was conducted in the same manner as in Synthesis Example 1-c using 2-bromo-6- (4-phenylphenyl) naphthalene as a starting material and recrystallization with 1,2-dichlorobenzene was repeated once to obtain N , N- dimethylformamide Lt; RTI ID = 0.0 > 1 < / RTI > (Y = 73%)

[Reaction formula 12: synthesis of B-35]

Synthetic example  12-a: 1- bromo Synthesis of 4- (4-phenylphenyl) naphthalene

4-biphenylboronic acid and 1,4-dibromonaphthalene as starting materials, the synthesis was carried out as in Synthesis Example 2-c and recrystallized from chlorobenzene. (Y = 70%)

Synthetic example  12-b: Synthesis of B-35

Synthesis was carried out in the same manner as in Synthesis Example 1-c using B-1-2 and 1-bromo-4- (4-phenylphenyl) naphthalene as starting materials and recrystallization with 1,2-dichlorobenzene was repeated once to obtain N , N- dimethylformamide Lt; RTI ID = 0.0 > 1 < / RTI > (Y = 76%)

compare Synthetic example :

[Compound a] [Compound b] [Compound c]

[Compound d] [ Compound e]

Synthetic example  13: Synthesis of compound a

Synthesis was carried out in the same manner as in Synthesis Example 1-c using 2 equivalents of B-1-1 and 1-bromonaphthalene as starting materials, followed by one recrystallization with 1,2-dichlorobenzene and one recrystallization with N , N- dimethylformamide. (Y = 50%)

Synthetic example  14: Synthesis of compound b

Synthesis was carried out as in Synthesis Example 1-c using 2 equivalents of B-1-1 and 4-bromobiphenyl as starting materials, followed by one recrystallization with 1,2-dichlorobenzene and one recrystallization with N , N- dimethylformamide. (Y = 84%)

Synthetic example  15: Synthesis of compound c

[Reaction formula 13: Synthesis of compound c]

Compound c-1 was synthesized by proceeding as in Synthesis Example 1-a using 2-bromo-9- (2-naphthylyl) carbazole and 2-chloroaniline as starting materials. Then, the synthesis was proceeded as in Synthesis Example 1-b to synthesize / purify the compound c-2. Finally, the compound c-2 and 2-bromonaphthalene were synthesized in the same manner as in Synthesis Example 1-c, and recrystallization with 1,2-dichlorobenzene and recrystallization with N , N- dimethylformamide were repeated once to obtain Compound c . (total Y = 44%)

Synthetic example  16: Synthesis of compound d

As described in U.S. Publication No. US2013-0264561A, indol [3,2-a] carbazole and 3-bromobiphenyl were synthesized as starting materials and purified by column chromatography to obtain compound d. (Y = 65%) (the same method as in Synthesis Example 1-c)

Synthetic example  17: Synthesis of Compound e

[Reaction Scheme 14: Synthesis of Compound e]

Synthetic example  17-a: 4- bromo -9-phenyl-carbazole

Synthesis was conducted as in Synthetic Example 7-b using 4-bromo-9H-carbazole as starting material and purified by column chromatography with n- hexane: dichloromethane mixed solution. (Y = 72%)

Synthetic example  17-b: 9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) ole  Synthesis of

(30.0 g, 93 mmol), bis (pinacolato) diboron (35.5 g, 140 mmol), potassium acetate (27.4 g, 279 mmol) and [1,1'- bis (diphenylphosphino) ferrocene] -dichloropalladium (II) (3.0 g, 4 mmol) was added to 450 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 filtrate solution was evaporated and recrystallized from dichloromethane: n- hexane to obtain 9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) carbazole 29.2 g, Y = 84.9%).

Synthetic example  17-c: Synthesis of 4- (2-nitrophenyl) -9-phenyl-carbazole

1-bromo-2-nitrobenzene and 9-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Synthesis proceeded and recrystallization was performed with n- hexane: dichloromethane mixed solution. (Y = 82%)

Synthetic example  17-d: Synthesis of 5-phenyl-5,8-dihydroindolo [2,3-c] carbazole

(20.0 g, 55 mmol) and triphenylphos phine (28.8 g, 110 mmol) were added to 1,2-dichlorobenzene and the mixture was stirred at 180 ° C for 12 hours in a nitrogen stream . After the reaction was completed, all of the solvent was evaporated and purified by column chromatography with n- hexane: dichloromethane mixture to obtain 5-phenyl-5,8-dihydroindolo [2,3-c] carbazole (11 g, Y = 60.3% .

Synthetic example  17-e: Synthesis of Compound e

Synthesis was conducted as in Synthesis Example 1-c using 5-phenyl-5,8-dihydroindolo [2,3-c] carbazole and 4-bromo- p -terphenyl as starting materials and recrystallized from chlorobenzene. (Y = 68%)

(Synthesis of compound for second organic optoelectronic device)

Synthetic example  18: Synthesis of D-3

[Reaction Scheme 15: Synthesis of D-3]

Synthetic example  18-a: Synthesis of D-3-1

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, 1-bromo-3,5 -diphenylbenzene (100 g, 323 mmol) is slowly added dropwise at 0 占 폚 over 30 minutes. The resulting mixed solution 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 thus-obtained residue was purified by flash column chromatography to obtain Intermediate D-3-1 (79.4 g, 65%).

Synthetic example  18-b: Synthesis of Compound D-3

D-3-1 and 3-dibenzofuranylboronic acid were synthesized in the same manner as in Synthesis Example 2-c and purified by chlorobenzene. (Y = 72%)

Synthetic example  19: Synthesis of D-23

[Reaction Formula 16: Synthesis of D-23]

Synthetic example  19-a: Synthesis of D-23-1

Synthesis and purification were conducted in the same manner as in Synthesis Example 18-a using 4-bromobiphenyl as a starting material to obtain Intermediate D-23-1. (Y = 75%)

Synthetic example  19-b: Synthesis of D-23-2

Intermediate D-23-1 and 3-dibenzofuranyl boronic acid were synthesized and purified in the same manner as in Synthesis Example 2-c using the starting material to synthesize Intermediate D-23-2. (Y = 65%)

Synthetic example  19-c: Synthesis of D-23

Intermediate D-23-2 and 1.1 equivalent of 2 - ([1,1 ': 3', 1 "-terphenyl] -5'-yl) -4,4,5,5-tetramethyl- -dioxaborolane was used to synthesize compound D-23 in the same manner as in Synthesis Example 2-c. (Y = 69%)

Synthetic example  20: Synthesis of D-24

[Reaction Scheme 17: Synthesis of D-24]

Using the intermediate B-23-2 and 1.1 equivalent of B- [1,1 ': 4', 1 "-terphenyl] -3-yl boronic acid, compound D-24 Were synthesized. (Y = 59%)

Synthetic example  21: Synthesis of D-71

[Reaction Scheme 18: Synthesis of D-71]

Synthetic example  21-a: Synthesis of D-71-1

3-bromodibenzofuran and 3-chlorophenylboronic acid were synthesized in the same manner as in Synthesis Example 2-c and recrystallized from toluene. (Y = 76%)

Synthetic example  21-b: Synthesis of D-71-2

Synthesis was conducted in the same manner as in Synthesis Example 17-b using D-71-1 as a starting material, and the slurry was purified with a small amount of n- hexane to obtain Intermediate D-71-2. (Y = 70%)

Synthetic example  21-c: Synthesis of D-71

1.0 equivalents of the synthesized intermediate D-71-2 and 2,4-bis ([1,1'-biphenyl] -4-yl) -6-chloro-1,3,5- Was synthesized in the same manner as in Example 2-c and purified with chlorobenzene. (Y = 55%)

(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 ITO transparent electrode thus prepared as an anode to form a hole injection layer having a thickness of 700 A and a compound B was deposited to a thickness of 50 A on the injection layer, To form a hole transporting layer. Compound A-1 was deposited to a thickness of 400 Å on the hole transporting layer to form a hole transporting auxiliary layer. Compound E was used as a host on the hole transport layer, doped with 2 wt% of dopant [Ir (piq) ₂ acac], and a 400 Å thick light emitting layer was formed by vacuum deposition. 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.

(400 Å) [Compound (E) [Ir (piq) ₂ acac] (400 Å)] was added to the mixture of ITO / Compound A (700 Å) / Compound B (50 Å) / Compound C (700 Å) / Compound A- / 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 C-1: N, N-di ([1,1'-biphenyl] -4-yl) -7,7-dimethyl-7H-fluoreno [4,3-b] benzofuran-

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

Compound E: 9-phenyl-9 '- (4-phenylquinazolin-2-yl) -9H, 9'H-3,3'- bicarbazole

Example  2 to Example  5 and Comparative Example  1 to 5

The devices of Examples 2 to 5 and Comparative Examples 1 to 5 were fabricated in the same manner as in Example 1 using the hole transporting auxiliary layer of the present invention as shown in Table 1 below.

Example  6 - Comparative Example  19 and Reference example  1 to Reference example  5

Compound C-1 was deposited on the hole transport layer to a thickness of 400 Å to form a hole transporting auxiliary layer. As shown in the following Table 2, the first host and the second host of the present invention were used The devices of Examples 6 to 19 and Reference Examples 1 to 5 were fabricated. Here, the first host and the second host were used at a weight ratio of 3: 7. [0064] The organic light emitting device has a structure having five organic thin film layers, and specifically, the following.

Evaluation: luminescence efficiency and lifetime Synergistic effect  Confirm

The luminescent efficiency and lifetime characteristics of the organic luminescent devices according to Examples 1 to 18, Comparative Examples 1 to 5, and Reference Examples 1 to 5 were evaluated. The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

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

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

(2) Measurement of luminance change according to voltage change

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

(3) Measurement of luminous efficiency

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

(4) Life measurement

Examples 1 to 5 and Comparative Examples 1 to 5 to emit light in the device at an initial luminance (cd / m ²⁾ as 6000cd / m ² and over time using a polar Optronics lifetime measuring system for the manufacture of organic light emitting devices And the time point at which the luminance was reduced to 90% of the initial luminance was measured as the T97 lifetime.

Hole transporting auxiliary layer color Life span (h) Example 1 A-1 Red 147 Example 2 A-13 Red 185 Example 3 A-21 Red 169 Example 4 A-49 Red 150 Example 5 B-33 Red 123 Comparative Example 1 The compound a Red 85 Comparative Example 2 Compound b Red 110 Comparative Example 3 Compound c Red 61 Comparative Example 4 Compound d Red 55 Comparative Example 5 Compound e Red 120

1st
Host Second
Host The first host +
Second host
ratio color efficiency Example 6 A-1 D-3 3: 7 Red 21.2 Example 7 A-1 D-23 3: 7 Red 21.2 Example 8 A-13 D-3 3: 7 Red 22.1 Example 9 A-21 D-3 3: 7 Red 22.0 Example 10 A-49 D-3 3: 7 Red 22.8 Reference Example 1 Compound c D-3 3: 7 Red 19.8 Reference Example 2 Compound d D-3 3: 7 Red 20.5 Example 11 B-1 D-3 3: 7 Red 22.4 Example 12 B-1 D-23 3: 7 Red 22.4 Example 13 B-1 D-24 3: 7 Red 22.0 Example 14 B-1 D-71 3: 7 Red 22.0 Example 15 B-5 D-3 3: 7 Red 23.2 Example 16 B-13 D-3 3: 7 Red 23.0 Example 17 B-21 D-3 3: 7 Red 22.7 Example 18 B-33 D-3 3: 7 Red 22.5 Example 19 B-35 D-3 3: 7 Red 22.0 Reference Example 3 The compound a D-3 3: 7 Red 20.5 Reference Example 4 Compound b D-3 3: 7 Red 21.0 Reference Example 5 Compound e D-3 3: 7 Red 18.9

Referring to Table 1, it is confirmed that the compound according to the present invention provides an excellent lifetime compared to Comparative Examples 1 to 5 which are known compounds.

Also, referring to Table 2, it can be seen that the efficiency characteristics are superior to those of the mixed host using the same second host when using the first host and the second host according to the present invention.

As a result, it can be confirmed that the structure in which the linear arylene is elongated on the basis of the same indolecarbazole skeleton has a higher efficiency than that in the structure having a shorter length.

Compounds A-1 to A-49 of the indolo [2,3-b] carbazole skeleton in which the intermolecular packing is strengthened by linear symmetry with respect to the compound d having indolo [3,2- can see. Likewise, indole [3,2-b] carbazole skeleton compounds B-1 to B-35 having a more flat structure in point-symmetry with respect to the indolo [2,3-c] carbazole skeleton exhibit high efficiency. From these results, it can be concluded that the efficiency increases as the molecular structure is flattened in the two indole cyclases.

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 (15)

A compound for a first organic optoelectronic device represented by a combination of the following formulas (1) and (2): < EMI ID =
[Chemical Formula 1] < EMI ID =

In the above formulas (1) and (2)
* Is a connecting point of formulas (1) and (2)
Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,
Ar ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group,
R ¹ to R ⁴ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
L ⁴ is a single bond or a substituted or unsubstituted C6 to C20 arylene group,
The total number of carbon atoms in " -L ⁴ -Ar ² " is 16 to 50. The method according to claim 1,
A compound for a first organic optoelectronic device represented by any of the following formulas (1A) to (1A '''):
≪ RTI ID = 0.0 > 1A '

≪ RTI ID = 0.0 > 1A '"

In the above formulas (1A) to (1A '''),
Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,
Ar ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group,
R ¹ to R ⁴ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
R ¹⁴ and R ¹⁵ are each independently present or may combine with each other to form a fused ring. The method according to claim 1,
A compound for a first organic optoelectronic device represented by any one of the following formulas (1B) to (1B '
[Chemical Formula 1B] < EMI ID =

≪ RTI ID = 0.0 > [1B ''] <

In the above formulas (1B) to (1B '''),
Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,
Ar ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group,
R ¹ to R ⁴ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
R ¹⁴ and R ¹⁵ are each independently present or may combine with each other to form a fused ring. The method according to claim 1,
Ar ¹ is an unsubstituted phenyl group, an unsubstituted biphenyl group, or an unsubstituted naphthyl group,
Ar ² is an unsubstituted phenyl group, an unsubstituted biphenyl group or an unsubstituted naphthyl group,
And R &^lt; ¹ > to R &^lt; ⁴ &^gt; are each independently a hydrogen atom. 5. The method of claim 4,
Wherein Ar < ² > is selected from the substituents listed in the following Group II:
[Group II]

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]

[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-32]

[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]

. A first organic optoelectronic device compound according to claim 1; And
1. A composition for an organic optoelectronic device comprising a compound for a second organic optoelectronic device represented by the following Formula 3:
(3)

In Formula 3,
X < ¹ > is O or S,
Z ¹ to Z ³ are each independently N or CR ^a ,
At least two of Z ¹ to Z ³ are N,
L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
A ¹ and A ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
At least one of A ¹ and A ² is a substituted or unsubstituted C6 to C30 aryl group,
R ^a and R ⁵ to R ⁷ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group. 8. The method of claim 7,
Wherein the compound for the second organic optoelectronic device is represented by any one of the following formulas (III-IB-1) to (III-IB-3)
[IB-3] < / RTI > [IB-3]

In Formulas 3-IB-1 to 3-IB-3,
Ar ³ is a substituted or unsubstituted C6 to C20 aryl group,
X ¹ and X ² are each independently O or S,
Z ¹ to Z ⁶ are each independently N or CR ^a ,
At least two of Z ¹ to Z ³ are N,
At least two of Z ⁴ to Z ⁶ are N,
L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Each of R ^a , R ^b , R ^c , R ^d and R ⁵ to R ⁹ is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group . 8. The method of claim 7,
A ¹ in Formula 3 is a substituted or unsubstituted C6 to C20 aryl group,
A ² in Formula 3 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted thiazinyl group. 10. The method of claim 9,
A ¹ in Formula 1 is selected from the substituents listed in Group III below,
Wherein A ² in the formula (1) is selected from the substituents listed in the following group IV:
[Group III]

[Group IV]

In the group III, * is a connecting point with L ² ,
In the above group IV, * is a connection point with L ³ . 8. The method of claim 7,
The compound for a first organic optoelectronic device is represented by the following general formula (1A-1) or (1B-1)
Wherein the compound for the second organic optoelectronic device is represented by the following Formula 3-1B-1 or Formula 3-1B-2:
[Formula 1A-1] [Formula 1B-1]

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

In Formulas 1A-1 and 1B-1,
Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,
Ar ² is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group,
R ¹ to R ⁴ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
R ¹⁴ and R ¹⁵ are each independently present or may combine with each other to form a fused ring,
In the above formula (3-IB-1) or (3-IB-2)
X ¹ and X ² are each independently O or S,
Z ¹ to Z ³ are each independently N or CR ^a ,
At least two of Z ¹ to Z ³ are N,
L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
R ^a and R ⁵ to R ⁹ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
R ^b to R ^d are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group,
Ar ³ is a substituted or unsubstituted C6 to C20 aryl group. Positive and negative facing each other, and
And at least one organic layer positioned between the anode and the cathode,
Wherein the organic layer includes an auxiliary layer including at least one of a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron injecting layer and an electron transporting layer, and a light emitting layer,
Wherein the light emitting layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 6 or the composition for an organic optoelectronic device according to any one of claims 7 to 11. 13. The method of claim 12,
Wherein the compound for an organic optoelectronic device is contained in at least one auxiliary layer selected from the hole injection layer, the hole transporting layer and the electron blocking layer. 13. The method of claim 12,
Wherein the composition for the organic optoelectronic device is included 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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