KR20190079339A - Compound for organic optoelectric device, composition for organic optoelectric device, organic optoelectric device and display device - Google Patents

Abstract

The present specification relates to a compound for organic optoelectronic device represented by a chemical formula 1, a composition for organic optoelectronic device including the same, and an organic optoelectronic device and display device to which the compound is applied. The details of a chemical formula 1 are as defined in the specification. The compound for organic optoelectronic device may implement the organic optoelectronic device with the high efficiency and long life.

Description

Technical Field The present invention relates to a compound for organic optoelectronic devices, a composition for organic optoelectronic devices, 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 organic optoelectronic devices comprising the composition.

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

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

[Chemical Formula 1]

In Formula 1,

X < ¹ > is O or S,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group ,

At least one of R ⁶ and R ⁷ is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one nitrogen atom,

At least one of R ⁵ to R ⁸ is represented by the following general formula (2)

(2)

In Formula 2,

X ² is O or S,

R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .

According to another embodiment, there is provided a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

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, and the organic layer is a composition for a compound for organic optoelectronic devices or a composition for organic optoelectronic devices Organic photovoltaic devices.

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, respectively.

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, A C1 to C20 alkoxy group, a C1 to 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. Further, in a specific example of the present invention, "substituted" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group . In a specific example of the present invention, "substituted" means that at least one hydrogen in the substituent or compound is substituted with one or more groups selected from the group consisting of deuterium, methyl, ethyl, propanyl, butyl, phenyl, biphenyl, terphenyl, A dibenzofuranyl group, or a 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 grouping of groups having one or more hydrocarbon aromatic moieties,

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.

Specific examples of the heterocyclic group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl 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 triphenylene group, a substituted or unsubstituted perylenyl 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, 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 benzoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted Substituted or unsubstituted benzothiazyl groups, substituted or unsubstituted benzothiazyl groups, substituted or unsubstituted benzothiazyl groups, substituted or unsubstituted aryidinyl groups, substituted or unsubstituted phenazinyl groups, substituted or unsubstituted phenothiazine A substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene 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 so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer migrate to the cathode, It is a characteristic that facilitates movement.

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

The compound for organic optoelectronic devices according to one embodiment can be represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X < ¹ > is O or S,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group ,

At least one of R ⁶ and R ⁷ is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one nitrogen atom,

At least one of R ⁵ to R ⁸ is represented by the following general formula (2)

(2)

In Formula 2,

X ² is O or S,

R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .

The compound represented by Formula 1 can serve as an electron injecting, electron transporting or luminescent material in an organic optoelectronic device. In particular, when used as a light emitting material, a driving voltage can be lowered and an organic optoelectronic device having a high efficiency can be manufactured .

In Formula 1, since at least one of R ⁵ to R ⁸ is represented by the following formula (2), it has a polar group, which enables interaction with the electrode, facilitating injection of electrons and increasing mobility, The driving voltage drop and the high efficiency effect can be obtained at the same time. In addition, since the compound represented by Formula 1 has an asymmetric structure, decomposition during deposition can be suppressed.

In one embodiment of the present invention, at least one of R ⁶ and R ⁷ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, A substituted or unsubstituted quinazolinyl group or a substituted or unsubstituted benzothienopyrimidinyl group.

For example, at least one of R < ⁶ > and R < ⁷ >

(3)

In Formula 3,

X ³ to X ⁵ are each independently N or CR ^a (R ^a is hydrogen or a C1 to C10 alkyl group)

At least one of X ³ to X ⁵ is N,

R ¹⁴ and R ¹⁵ are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group .

In Formula 3, at least two of X ³ to X ⁵ may be N.

In Formula 3, R ¹⁴ and R ¹⁵ each independently represent any one substituent selected from the following Group I.

[Group I]

The formula (2) may be represented by the following formula (2-1) or (2-2).

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

In the above formulas (2-1) to (2-2)

X ² are each independently O or S,

R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .

For example, the compound for organic optoelectronic devices represented by Formula 1 may be selected from the compounds listed in Group 1 below, but is not limited thereto.

[Group 1]

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

The present invention provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device represented by the above-mentioned Formula 1 (compound for a first organic optoelectronic device).

Also, the present invention can provide a composition for an organic electronic device comprising the compound for the first organic optoelectronic device and the compound represented by the following formula (4) (compound for a second organic optoelectronic device).

[Chemical Formula 4]

In Formula 4,

Y ¹ and Y 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,

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

R ¹⁶ to R ²¹ are each independently selected from the group consisting of 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 C50 heterocyclic group, ego,

m is an integer of 0 to 2;

In one embodiment of the invention, Y ¹ and ^Y2 of the formula (4) each independently be a C6 to C18 arylene date a single bond, or a substituted or unsubstituted.

In one embodiment of the present invention, Ar ¹ and Ar ² in Formula 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted A naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolyl group, a substituted A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzothiophenylene group, . ≪ / RTI >

In one embodiment of the present invention, R ¹⁶ to R ²¹ in Formula 4 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

In one embodiment of the present invention, m in Formula 4 may be 0 or 1.

In one specific embodiment of the present invention, the above-mentioned formula (4) is one of the structures listed in the following Group II, and * -Y ¹ -Ar ¹ and * -Y ² -Ar ² are one of the substituents listed in Group III below .

[Group II]

[Group III]

In Groups II and III, * is a connection point.

Specifically, the formula (4) is represented by C-8 of the group II, and * -Y ¹ -Ar ¹ and * -Y ² -Ar ² are any one of B-1 to B-4 of the group III Can be expressed.

More specifically, * -Y ¹ -Ar ¹ , and * -Y ² -Ar ² may be selected from B-2, B-3, and combinations thereof of Group III.

The compound for the second organic optoelectronic device represented by Formula 4 may be, for example, compounds listed in the following Group 2, but is not limited thereto.

[Group 2]

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

[C-6] [C-7] [C-8] [C-9]

[C-11] [C-12] [C-13] [C-14]

[C-16] [C-17] [C-18] [C-19]

[C-21] [C-22] [C-23] [C-24]

[C-26] [C-27] [C-28] [C-29]

[C-31] [C-32] [C-33] [C-34]

[C-36] [C-37] [C-38] [C-39]

[C-41] [C-42] [C-43] [C-44]

[C-46] [C-47] [C-48] [C-49]

[C-51] [C-52] [C-53] [C-54]

[C-56] [C-57] [C-58] [C-59]

[C-61] [C-62] [C-63] [C-64]

[C-66] [C-67] [C-68] [C-69]

[C-71] [C-72] [C-73] [C-74]

[C-76] [C-77] [C-78] [C-79]

[C-81] [C-82] [C-83] [C-84]

[C-86] [C-87] [C-88] [C-89]

[C-91] [C-92] [C-93] [C-94]

[C-96] [C-97] [C-98] [C-99]

[C-101] [C-102] [C-103] [C-104]

[C-106] [C-107] [C-108] [C-109]

[C-111] [C-112] [C-113] [C-114]

[C-116] [C-117] [C-118] [C-119]

[C-121] [C-122] [C-123] [C-124]

[C-126] [C-127] [C-128] [C-129]

[C-131] [C-132] [C-133] [C-134]

[C-136] [C-137] [C-138] [C-139]

The present invention also relates to an organic electroluminescent device comprising a compound for the first organic optoelectronic device and a compound consisting of a combination of a moiety represented by the following formula (5) and a moiety represented by the following formula (6) A composition for a device can be provided.

[Chemical Formula 5]

In the above formulas (5) and (6)

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

Ar ³ and Ar ^{4 are} each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ²² to R ²⁵ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or combinations thereof ,

The adjacent two * in the formula (5) are combined with two * in the formula (6) to form a fused ring. In the formula (5), the fused rings are independently CR ^b ,

R ^b is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or combinations thereof.

For example, Ar ³ and Ar ⁴ may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a combination thereof.

For example, at least one of Ar ³ and Ar ⁴ may include a substituted or unsubstituted carbazole group.

The second organic compound composed of the combination of the moiety represented by the formula (5) and the moiety represented by the formula (6) may be represented by any one of the following formulas (7-1) to (7-5) according to the bonding position.

[Formula 7-1] [Formula 7-2]

[Formula 7-3] [Formula 7-4-4]

[Formula 7-5]

In Formulas 7-1 to 7-5,

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

Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ²² to R ²⁵ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or combinations thereof .

For example, at least one of Ar ³ and Ar ⁴ in formulas (7-1) to (7-5) may be a substituent having a hole property, and may include, for example, a substituted or unsubstituted carbazole group. The compound for the second organic optoelectronic device composed of the combination of the moiety represented by Formula 5 and the moiety represented by Formula 6 may be, for example, a compound listed in Group II below, but is not limited thereto. [Group IV] (in the specific compounds described in [Group IV] below, all the heteroatoms are "N").

[Group IV]

The composition according to one embodiment may be applied to an organic layer of an organic optoelectronic device, for example, to a light emitting layer of an organic optoelectronic device, and the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be a host, Can play a role. Here, the first organic optoelectronic device compound may be a compound having a bipolar characteristic having a relatively high electron characteristic, and the second organic optoelectronic device compound may have a bipolar characteristic having a relatively high hole characteristic. Can be used together with a compound for an organic optoelectronic device to improve the mobility and stability of charge, thereby further improving the luminous efficiency and lifetime characteristics.

In the device in which the electron or the hole characteristic is biased to the light emitting layer, the recombination of the carriers occurs at the interface between the light emitting layer and the electron transporting layer or the hole transporting layer, and the formation of the excitons is relatively increased. As a result, a roll-off phenomenon in which the efficiency is drastically decreased due to the interaction between molecular excitons in the light emitting layer and the charge at the interface of the transport layer occurs, and the luminescent lifetime characteristics also sharply drop. To solve this problem, the compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device are simultaneously introduced into a light emitting layer as a host compound to adjust the carrier balance in the light emitting layer so that the light emitting region is not shifted to either the electron transporting layer or the hole transporting layer It is possible to remarkably improve the lifetime characteristics as well as the roll-off.

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.

As described above, the compound for the second organic optoelectronic device can be used in the light emitting layer together with the compound for the first organic optoelectronic device, thereby improving the drivability, luminescence efficiency and lifetime characteristics by increasing the charge mobility and increasing the stability .

The compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device may be used in a ratio of about 1: 9 to 9: 1, 2: 8 to 8: 2, 3: 7 to 7: : 4, and 5: 5, and specifically in a weight ratio of 1: 9 to 8: 2, 1: 9 to 7: 3, 1: 9 to 6: 4, 1: 9 to 5: And more specifically may be included in a weight ratio of 2: 8 to 7: 3, 2: 8 to 6: 4, and 2: 8 to 5: 5. Also, it can be contained in a weight ratio of 3: 7 to 6: 4, and 3: 7 to 5: 5, and most specifically in a weight ratio of 3: 7 to 4: 6 or 5:

The composition for organic optoelectronic devices may be used as a host of a green or red organic light emitting device.

The compound or composition for an organic optoelectronic device may further include at least one organic compound in addition to other compounds for an organic optoelectronic device.

The composition comprising the compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device may further include a dopant.

The dopant may be a red, green or blue dopant, for example a red or green phosphorescent 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 organic metal compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, For example, a compound represented by the following formula (Z) may be used, 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 >

More specifically, the phosphorescent dopant is an organometallic compound containing one of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, In one specific embodiment, the phosphorescent dopant may be an organometallic compound represented by the following formula (401).

≪ Formula 401 >

In Formula 401, M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm; X401 to X404 independently of one another are nitrogen or carbon; The A401 and A402 rings may be, independently of one another, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted indene, substituted Substituted or unsubstituted pyrazoles, substituted or unsubstituted thiols, substituted or unsubstituted thiophenes, substituted or unsubstituted furan, substituted or unsubstituted imidazoles, substituted or unsubstituted pyrazoles, substituted or unsubstituted thiols, substituted or unsubstituted thiophenes, Substituted or unsubstituted pyrazole, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazole, substituted or unsubstituted pyrazole, substituted or unsubstituted pyrazole, substituted or unsubstituted thiophene, Substituted or unsubstituted pyrazine, unsubstituted pyridazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, Substituted or unsubstituted benzoimidazoles, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophenes, substituted or unsubstituted isobenzothiophenes, substituted or unsubstituted benzothiophenes, substituted or unsubstituted benzothiophenes, Substituted or unsubstituted benzoxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, And substituted or unsubstituted dibenzothiophene; The term "substituted" as used herein means that at least one hydrogen in the substituent or the compound is substituted with a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, a cyano group, an amino group, a substituted or unsubstituted C1 to C30 amine group, C3 to C30 heterocycloalkyl groups, C6 to C30 aryl groups, C2 to C30 heterocyclic groups, C1 to C30 aryl groups, C3 to C30 heterocycloalkyl groups, C3 to C30 heterocycloalkyl groups, C1 to C30 alkyl groups, C1 to C10 alkylsilyl groups, C6 to C30 arylsilyl groups, C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a combination thereof; L401 is an organic ligand; xc1 is 1, 2 or 3; xc2 is 0, 1, 2 or 3;

The L401 may be any monovalent, divalent or trivalent organic ligand. For example, L401 may be a halogen ligand (e.g., Cl, F), a diketone ligand (e.g., acetylacetonate, 1,3-diphenyl-l, 3- propanedionate, 2,2,6 , 6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (for example, picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon mono But are not limited to, an oxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorus ligand (for example, phosphine, phosphite).

Q401 to Q407, Q411 to Q417 and Q421 to Q427 are independently selected from hydrogen, a C1 to C60 alkyl group, a C2 to C60 alkenyl group, a C6 to C60 aryl group, and a C2 to C60 heteroaryl group.

When A401 in the above formula (401) has two or more substituents, two or more substituents of A401 may be bonded to each other to form a saturated or unsaturated ring.

When A402 in the above formula (401) has two or more substituents, two or more substituents of A402 may be bonded to each other to form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A401 및 A402는 각각 이웃하는 다른 리간드의 A401 및 A402와 각각 직접(directly) 또는 연결기(예를 들면, C1 내지C5 알킬렌기, -N(R')-(여기서, R'은 C1 내지 C10 알킬기 또는 C6 내지 C20 아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands of Formula 401

May be the same or different from each other. When xc1 in Formula 401 is 2 or more, A401 and A402 are each directly or indirectly linked to A401 and A402 of another adjacent ligand (e.g., C1 to C5 alkylene group, -N (R ') - ( Wherein R 'is a C1 to C10 alkyl group or a C6 to C20 aryl group) or -C (= O) -).

For example, the phosphorescent dopant may be a red or green phosphorescent dopant and may be selected from the following compounds PD1 to PD75, but is not limited thereto.

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. When the composition of the present invention is used as a host, the combination ratio thereof may vary depending on the kind of the dopant used and the propensity of the dopant, and the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device For example, in a weight ratio of 1:10 to 10: 1. And specifically may be 2: 8 to 8: 2, 9: 1 to 5: 5, 8: 2 to 5: 5 and 7: 3 to 5: 2 < / RTI > compound for organic optoelectronic devices may be 5: 5.

The bipolar characteristics can be more effectively realized by including them in the weight ratio range, thereby improving efficiency and lifetime at the same time.

The composition may be formed by a dry film forming method such as chemical vapor deposition or a solution process.

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

An 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 may include the composition for the organic optoelectronic device described above .

For example, the organic layer includes a light emitting layer, and the light emitting layer may include a composition for an organic optoelectronic device 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 layer may include at least one auxiliary layer selected from a light emitting layer and a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer and a hole blocking layer, . ≪ / RTI >

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 SnO2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

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

The organic layer 105 includes the light emitting layer 130 including the compound for the organic optoelectronic device described above.

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

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole-assist layer 140 in addition to the light-emitting layer 130. The hole auxiliary layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.

1 or 2 may further include an electron injection layer, an electron transport layer, an electron transporting auxiliary layer, a hole transporting layer, a hole transporting auxiliary layer, a hole injecting layer, or a combination layer thereof have. The compound for organic optoelectronic devices of the present invention can be included in these organic layers. The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a dry deposition method such as evaporation, sputtering, plasma plating, and ion plating; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode or anode on the organic layer.

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

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

Hereinafter, the starting materials and reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI unless otherwise stated, or synthesized by known methods.

(Preparation of compound for organic optoelectronic device)

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

(Compound for first organic optoelectronic device)

Synthetic example  1: Synthesis of compound 2

[Reaction Scheme]

(1) A round bottom flask was charged with 15 g (53.58 mmol) of 4-bromo-2-chloro-Dibenzofuran, 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 1.858 g (1.61 mmol) of tetrakis (triphenylphosphine) palladium [Pd (PPh3) 4] and 7.406 g (53.58 mmol) of potassium carbonate were added to 200 mL of THF and 100 mL of distilled water, Was heated to reflux. When the reaction was completed, the reaction mixture was cooled to room temperature, and THF and distilled water were separated. Then, separated THF was added dropwise to 100 mL of methanol and crystallized. The resulting solid was filtered and washed with water and methanol. The resulting solid was dried in a vacuum oven to give compound 2-A (13 g, 66% yield).

MS (m / z, [M] < + >): 368.81

(2) A round bottom flask was charged with 1344 g (1.77 mmol), Tricyclohexylphosphine (1.981 g, 7.06 mmol), Potassium Acetate (10.4 g, 105.96 mmol), Bis pinacolato) diboron 10.76 g (42.76 mmol) was suspended in 100 ml of DMF and stirred at reflux for 48 hours. After completion of the reaction, the reaction mixture was poured into distilled water (300 ml), and the resulting solid was stirred for 1 hour, filtered, and then subjected to silica gel filtration to obtain the desired compound, 2-B (10 g, 62% yield).

MS (m / z, [M] < + >): 460.33

(3) To a round bottom flask was added 10 g (22.47 mmol) of 2-B, 6 g (22.47 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, tetrakis (triphenylphosphine) palladium 1.298 g (1.12 mmol) of [Pd (PPh3) 4] and 9.315 g (67.4 mmol) of potassium carbonate were added to 100 mL of THF and 30 mL of distilled water and the mixture was refluxed for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and THF and distilled water were separated. Then, separated THF was added dropwise to 100 mL of methanol and crystallized. The resulting solid was filtered and washed with water and methanol. The resulting solid was dried in a vacuum oven to give compound 2 (9 g, 71% yield).

MS (m / z, [M] < + >): 565.62

Synthetic example  2: Synthesis of Compound 3

[Reaction Scheme]

(1) A round bottom flask was charged with 20 g (71.45 mmol) of 4-bromo-2-chloro-Dibenzofuran, 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2.477 g (2.14 mmol) of tetrakis (triphenylphosphine) palladium [Pd (PPh3) 4] and 9.875 g (71.45 mmol) of potassium carbonate were placed in 300 mL of THF and 150 mL of distilled water, Was heated to reflux. When the reaction was completed, the reaction mixture was cooled to room temperature, and THF and distilled water were separated. Then, separated THF was added dropwise to 100 mL of methanol and crystallized. The resulting solid was filtered and washed with water and methanol. The resulting solid was dried in a vacuum oven to give compound 3-A (20 g, 76% yield).

MS (m / z, [M] < + >): 368.81

(2) A round bottom flask was charged with 20 g (54.34 mmol) of the intermediate compound 3-A, 2.2 g (2.72 mmol) of Pd (dppf) Cl2, 3 g (10.87 mmol) of tricyclohexylphosphine, 16 g 16.55 g (65.21 mmol) of pinacolato diboron are suspended in 135 ml of DMF, and the mixture is stirred under reflux for 48 hours. After completion of the reaction, the reaction mixture was poured into distilled water (300 ml), and the resulting solid was stirred for 1 hour, filtered, and then subjected to silica gel filtration to obtain the desired compound, 3-B (16 g, 64% yield).

MS (m / z, [M] < + >): 460.33

(3) To a round bottom flask was added 15.5 g (33.7 mmol) of 3-B, 9 g (33.7 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, tetrakis (triphenylphosphine) palladium 1.947 g (1.69 mmol) of [Pd (PPh3) 4] and 13.973 g (101.1 mmol) of potassium carbonate were dissolved in 170 mL of THF and 50 mL of distilled water and the mixture was refluxed for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and THF and distilled water were separated. Then, separated THF was added dropwise to 100 mL of methanol and crystallized. The resulting solid was filtered and washed with water and methanol. The solids obtained therefrom were dried in a vacuum oven to give compound 3 (12 g, 63% yield).

MS (m / z, [M] < + >): 565.62

Synthetic example  3: Synthesis of Compound 7

[Reaction Scheme]

12 g (26.23 mmol) of 3-B and 9 g (26.23 mmol) of 2- [1,1'-biphenyl] -4-yl-4-chloro- 1.513 g (1.31 mmol) of tetrakis (triphenylphosphine) palladium [Pd (PPh3) 4] and 10.877 g (78.70 mmol) of potassium carbonate were placed in 130 mL of THF and 40 mL of distilled water and the mixture was refluxed for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and THF and distilled water were separated. Then, separated THF was added dropwise to 100 mL of methanol and crystallized. The resulting solid was filtered and washed with water and methanol. The resulting solid was dried in a vacuum oven to give compound 7 (12 g, 71% yield).

MS (m / z, [M] < + >): 641.71

Comparative Synthetic Example  1: Synthesis of compound c

[Reaction Scheme]

(1) A round bottom flask was charged with 12 g (34.98 mmol) of intermediate C-1 (PharmaBlock, cas: 1472062-94-4), 5.457 g (34.98 mmol) of 3-chlorophenyl boronic acid, 14.5 g (104.93 mmol) 2.021 g (1.75 mmol) of Pd (PPh3) 4 (Tetrakis- (triphenylphosphine) palladium (0)) were placed in 150 mL of tetrahydrofuran and 75 mL of water, and then heated to 70 DEG C for 12 hours under a nitrogen stream. The resulting solid was dissolved in dichlorobenzene, filtered through silica gel / celite, an organic solvent was removed in an appropriate amount, and the residue was recrystallized from methanol to obtain Compound C-2 (12 g , 82% yield).

MS (m / z, [M] < + >): 419.12

(2) A round bottom flask was charged with 12 g (28.63 mmol) of Intermediate C-2, 6.072 g (28.63 mmol) of B-3-dibenzofuranyl-Boronic acid, 11.871 g (85.89 mmol) of potassium carbonate, - (triphenylphosphine) palladium (0)) (1.654 g, 1.43 mmol) were dissolved in tetrahydrofuran (130 mL) and water (40 mL), and the mixture was heated at 70 ° C for 12 hours under a nitrogen stream. The resulting solid was dissolved in dichlorobenzene, filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount. The resulting residue was recrystallized from methanol to obtain Compound C (10 g, 63 % Yield).

MS (m / z, [M] < + >): 551.20

(Compound for second organic optoelectronic device)

Synthetic example  4: Synthesis of Compound C-99

To a 500 mL round bottom flask equipped with a stirrer under nitrogen atmosphere was added 15.00 g (37.66 mmol) of 3-bromo-N-biphenylcarbazole, 16.77 g (37.66 mmol) of 3-boronic ester- 200 mL of toluene (1: 1) and 100 mL of a 2M potassium carbonate aqueous solution were mixed, and 2.18 g (1.88 mmol) of tetrakistriphenylphosphine palladium (0) was added thereto. The mixture was heated under reflux for 12 hours Respectively. After completion of the reaction, the reaction product was poured into methanol to filter the solid, and the obtained solid matter was sufficiently washed with water and methanol and dried. The resulting product was dissolved in 500 mL of chlorobenzene, and the solution was then subjected to silica gel filtration and the solvent was completely removed. The solvent was dissolved in 400 mL of toluene by heating and then recrystallized to obtain 16.54 g (yield 69%) of Compound C-99 .

[Formula C-99]

(Fabrication of organic light emitting device)

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. Compound C-99 and Compound 2 were simultaneously used as a host on the hole transport layer, doped with 7 wt% of Ir (ppy) ₃ as a dopant, and a 400Å thick light emitting layer was formed by vacuum deposition. Here, the compound C-99 and the compound 2 were used in a weight ratio of 6: 4, and the proportions were 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.

ITO / Compound A (700Å) / Compound B (50Å) / Compound C (1020Å) / EML [Compound C-99: Compound _{2: Ir (ppy) 3 (} 7wt%)] (400Å) / Compound D: Liq (300Å ) / 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) quinolone

Example  2, Example  3 and Comparative Example  One

The organic light emitting devices of Example 2, Example 3 and Comparative Example 1 were fabricated in the same manner as in Example 1 using the first host and the second host as shown in Table 1 below.

evaluation

The effects of the organic luminescent devices according to Examples 1 to 3 and Comparative Example 1 were evaluated as follows. The specific measurement method is as follows.

(1) Driving voltage measurement

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

(2) Measurement of change of 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.

(3) 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.

(4) 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 (2) and (3).

(5) External quantum efficiency (EQE)

For the fabricated organic light emitting device, all devices were evaluated by encapsulation with a desiccant, and the EQE was measured at the required luminance (9000 cd / m ² ) using an IPCE measurement system.

division The first host Second host First host:
Second host
(Weight ratio) Driving voltage
(V) Luminous efficiency
(cd / A) EQE Example 1 Compound 2 C-99 4: 6 3.90 67.3 19.6 Example 2 Compound 3 C-99 4: 6 3.86 70.1 19.4 Example 3 Compound 7 C-99 4: 6 3.88 72.9 20.1 Comparative Example 1 Compound c C-99 4: 6 4.01 69.9 19.4

Referring to Table 1, when the first host according to one embodiment is used alone or in combination with the second host, the driving voltage of the organic light emitting diode to which the first host is applied and the lifetime are remarkably improved .

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 (16)

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

In Formula 1,
X < ¹ > is O or S,
R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group ,
At least one of R ⁶ and R ⁷ is a substituted or unsubstituted C2 to C30 heterocyclic group containing at least one nitrogen atom,
At least one of R ⁵ to R ⁸ is represented by the following general formula (2)
(2)

In Formula 2,
X ² is O or S,
R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .
The method according to claim 1,
At least one of R ⁶ and R ⁷ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, Lt; RTI ID = 0.0 > benzothienopyrimidinyl < / RTI > group.
The method according to claim 1,
Wherein at least one of R < ⁶ > and R < ⁷ >
(3)

In Formula 3,
X ³ to X ⁵ are each independently N or CR ^a (R ^a is hydrogen or a C1 to C10 alkyl group)
At least one of X ³ to X ⁵ is N,
R ¹⁴ and R ¹⁵ are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group .
The method of claim 3,
Wherein at least two of X < ³ > to X < ⁵ > are N.
The method of claim 3,
And R < ¹⁴ > and R < ¹⁵ > are each independently any one substituent selected from the following Group I.
[Group I]

The method according to claim 1,
(2) is represented by the following formula (2-1) or (2-2): < EMI ID =
[Formula 2-1] [Formula 2-2]

In the above formulas (2-1) to (2-2)
X ² are each independently O or S,
R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .
A composition for organic optoelectronic devices comprising the compound for organic optoelectronic devices according to claim 1.
8. The method of claim 7,
The composition for an organic optoelectronic device according to the present invention comprises a compound for an organic optoelectronic device represented by the following formula 4 or a compound for an organic optoelectronic device comprising a combination of a moiety represented by the following formula 5 and a moiety represented by the following formula 6 Compositions for optoelectronic devices:
[Chemical Formula 4]

In Formula 4,
Y ¹ and Y 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,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ¹⁶ to R ²¹ each represent A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof,
m is an integer of 0 to 2,
[Chemical Formula 5]

In the above formulas (5) and (6)
Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ²² to R ²⁵ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or combinations thereof ,
The adjacent two * in the formula (5) are combined with two * in the formula (6) to form a fused ring. In the formula (5), the fused rings are independently CR ^b ,
R ^b is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or combinations thereof.
9. The method of claim 8,
Ar ¹ and Ar ² in Formula 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra 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 thienyl group, a substituted or unsubstituted thienyl group, A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
9. The method of claim 8,
Wherein the formula (4) is one of the structures listed in the following Group II, and * -Y ¹ -Ar ¹ and * -Y ² -Ar ² are one of the substituents listed in the following Group III:
[Group II]

[Group III]

In Groups II and III, * is a connection point.
11. The method of claim 10,
Wherein * -Y ¹ -Ar ¹ and * -Y ² -Ar ² are each independently a group represented by any one of B-1 to B-4 of Group III Gt; < / RTI >
9. The method of claim 8,
Wherein the compound represented by the formula (5) and the moiety represented by the formula (6) is represented by at least one of the following formulas (7-1) to (7-5)
[Formula 7-1] [Formula 7-2]

[Formula 7-3] [Formula 7-4-4]

[Formula 7-5]

In the above formulas (7-1) to (7-5)
Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ²² to R ²⁵ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or combinations thereof .
9. The method of claim 8,
Wherein the compound for organic optoelectronic device represented by Formula 1 and the compound for organic optoelectronic device represented by Formula 4 are contained in a weight ratio of 3: 7 to 6: 4.
Positive and negative facing each other, and
And at least one organic layer positioned between the anode and the cathode,
Wherein the organic layer comprises the organic photovoltaic compound according to any one of claims 1 to 6 or the composition for organic optoelectronic devices according to any one of claims 7 to 13.
15. The method of claim 14,
Wherein the organic layer includes a light emitting layer,
Wherein the composition for the organic optoelectronic device is included as a host of the light emitting layer.
A display device comprising the organic opto-electronic device according to claim 14.

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