TW201811776A - Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

Disclosed are a compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device, an organic optoelectronic device including the same, and a display device. Details of Chemical Formula 1 are the same as those defined in the specification.

Description

Compound for organic photovoltaic device, composition for organic photovoltaic device, organic photovoltaic device and display device

The invention discloses a compound for an organic photovoltaic device, a composition for an organic photovoltaic device, an organic photovoltaic device and a display device.

Organic optoelectronic devices are devices that convert electrical energy into light energy and vice versa.

Organic photovoltaic devices can be classified as follows based on their driving principles. One is a photoelectric device, in which excitons are generated by light energy, separated into electrons and holes, and transferred to different electrodes to generate electric energy, and the other is a light-emitting device, in which a voltage or current is supplied to the electrode to generate light energy from electric energy .

The organic optoelectronic device may include, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, an organic photo conductor drum, and the like.

Among them, organic light emitting diodes (organic light emitting diodes, OLEDs) have recently attracted attention due to the increased demand for flat panel displays. An organic light emitting diode is a device that converts electric energy into light by applying a current to an organic light emitting material, and has a structure in which an organic layer is provided between an anode and a cathode. Herein, the organic layer may include a light emitting layer and an auxiliary layer (if necessary), and the auxiliary layer may be, for example, selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and a hole At least one layer of a barrier layer.

The efficiency of the organic light emitting diode can be affected by the characteristics of the organic layer, and among them, it can be mainly affected by the characteristics of the organic material of the organic layer.

Specifically, there is a need to develop an organic material capable of increasing hole and electron mobility while increasing electrochemical stability, so that the organic light emitting diode can be applied to a large-sized flat panel display.

The embodiment of the present invention provides a compound for an organic photovoltaic device, which can achieve an organic photovoltaic device with high efficiency and long life.

Another embodiment of the present invention provides a composition for an organic photovoltaic device including the compound for an organic photovoltaic device.

Another embodiment of the present invention provides an organic photovoltaic device including the compound.

Another embodiment of the present invention provides a display device including the organic photoelectric device.

According to an embodiment, a compound for an organic photovoltaic device represented by Chemical Formula 1 is provided.

[Chemical Formula 1]

In Chemical Formula 1, X ¹ to X ^{3 are} independently N or CR ^a , at least one of X ¹ to X ³ is N, Y is O or S, and Ar ¹ is a substituted or unsubstituted C6 to C30 Aryl, R ^a and R ¹ to R ^{12 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and L ¹ and L ^{2 are} independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group, and a and b are independently an integer ranging from 1 to 3.

According to another embodiment, an organic photovoltaic device includes an anode and a cathode facing each other and at least one organic layer, the at least one organic layer is disposed between the anode and the cathode, wherein the organic layer includes The compound of the organic photovoltaic device or the composition for an organic photovoltaic device.

According to yet another embodiment, a display device includes the organic optoelectronic device.

An organic photovoltaic device with high efficiency and long life can be achieved.

Hereinafter, embodiments of the present invention are explained in detail. However, these embodiments are exemplary and the present invention is not limited thereto, and the present invention is defined by the scope of the patent application scope.

In this specification, when a definition is not provided otherwise, "substituted" means that at least one hydrogen of a substituent or compound is deuterium, halogen, hydroxyl, amine, substituted or unsubstituted C1 to C30 amine, nitrate Group, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkane Group, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, fluoro, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

In the examples of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is deuterated, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 ring Alkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, or C2 to C30 heteroaryl substitutions. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, C1 to C20 alkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. In the specific examples of the present invention, "substituted" means that at least one hydrogen is deuterium, C1 to C20 alkyl, C6 to C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinine Phenyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl.

In this specification, when a definition is not otherwise provided, "hetero" means that one functional group contains 1 to 3 heteroatoms selected from N, O, S, P, and Si and the remainder is carbon.

In this specification, when a definition is not provided otherwise, "alkyl" means an aliphatic hydrocarbon group. Alkyl may be a "saturated alkyl" without 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, a C1 to C4 alkyl group may have 1 to 4 carbon atoms in the alkyl chain, and may be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, second Butyl and tertiary butyl.

Specific examples of the alkyl group may be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, third butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclo Jiji et al.

In this specification, "aryl" refers to a group containing at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have a p-orbital that forms a conjugate, such as phenyl, naphthyl, etc., two or more Each hydrocarbon aromatic moiety may be connected by a sigma bond, and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more hydrocarbon aromatic moieties are fused directly or indirectly to provide non-aromatic Fused ring. For example, it may be fluorenyl.

Aryl groups may include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

In this specification, "heterocyclyl" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P, and Si instead of a cyclic compound (for example, aryl, cycloalkyl, (Fused ring or combination thereof). When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl may contain one or more heteroatoms.

For example, "heteroaryl" may refer to an aryl group containing at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected through a sigma bond, or when the heteroaryl group contains two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

Specific examples of the heterocyclic group may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, and the like.

More specifically, the substituted or unsubstituted C6 to C30 aryl and / or the substituted or unsubstituted C2 to C30 heterocyclyl may be a substituted or unsubstituted phenyl, a substituted or unsubstituted Substituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted fluorenyl, substituted or Unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted Fluorenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, substituted or Unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted Or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted Thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or Unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted Benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl , Substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, Substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted Substituted dibenzofuranyl, or substituted or unsubstituted dibenzothienyl, or a combination thereof, But it is not limited to this.

In this specification, a single bond refers to a direct bond without carbon or a heteroatom other than carbon, and specifically means that L is a single bond, which means that a substituent connected to L is directly bonded to the central core. That is, in this specification, a single bond does not mean a methylene group which is bonded via a carbon.

In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and the holes formed in the anode can be determined based on the highest occupied molecular orbital (HOMO) energy level. It is easy to be injected into the light-emitting layer and transmitted in the light-emitting layer.

In addition, electronic characteristics refer to the ability to accept electrons when an electric field is applied, and the electrons formed in the cathode can be easily injected into the light-emitting layer due to the conduction characteristics according to the lowest unoccupied molecular orbital (LUMO) energy level and Transmission in the light-emitting layer.

Hereinafter, a compound for an organic photovoltaic device according to an embodiment is explained.

The compound for an organic photovoltaic device according to the embodiment is represented by Chemical Formula 1.

[Chemical Formula 1]

In Chemical Formula 1, X ¹ to X ^{3 are} independently N or CR ^a , at least one of X ¹ to X ³ is N, Y is O or S, and Ar ¹ is a substituted or unsubstituted C6 to C30 Aryl, R ^a and R ¹ to R ^{12 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, L ¹ It is a single bond independently of L ² or a substituted or unsubstituted C6 to C30 arylene group, and a and b are independently an integer ranging from 1 to 3.

According to the embodiment, the compound for an organic optoelectronic device represented by Chemical Formula 1 mainly includes a carbazole substituted with a carbazolyl group, and has a structure in which a heterocyclic group including at least one nitrogen is Make the connection at position 3.

The nitrogen-containing heterocyclic group according to the embodiment is directly connected to dibenzofuran or dibenzothiophene without a linker, and is connected at the 3rd position of dibenzofuran or dibenzothiophene, and therefore has a When an electric field is applied to a LUMO orbit, the structure of the LUMO orbit expands easily and accepts electrons. Therefore, a driving voltage of an organic photovoltaic device manufactured by applying a compound for an organic photovoltaic device can be reduced.

In addition, the compound for an organic photovoltaic device according to the embodiment includes a nitrogen-containing heterocyclic ring attached at the third position of dibenzofuran or dibenzothiophene having a large triplet energy and electrochemical stability, and Contains carbazole, so it has both an electron withdrawing group (EWG) and an electron donating group (EDG), showing bipolar characteristics on the entire molecule, and has a high gap between holes and electrons The binding force, and therefore, can be applied to the transmission layer and the hole injection layer and used as a host in a light emitting layer of an organic photoelectric device.

Therefore, when the compound represented by Chemical Formula 1 of the present invention is used as a material of a hole injection layer, a hole transport layer, or a light emitting layer of an organic light emitting diode, the efficiency and life of the organic light emitting diode can be improved.

In Chemical Formula 1, preferably, X ¹ to X ³ in at least two of N, and more preferably, all of X ¹ to X ³ are both N.

A compound for an organic photovoltaic device according to an exemplary embodiment may be represented by Chemical Formula 1-1 to Chemical Formula 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3]

In Chemical Formulas 1-1 to 1-3, X ¹ to X ^{3 are} independently N or CR ^a , at least one of X ¹ to X ³ is N, and Ar ¹ is a substituted or unsubstituted C6 to C30 aryl, Y is O or S, R ^a and R ¹ to R ^{12 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl , Or a combination thereof, L ¹ and L ^{2 are} independently a single bond, or a substituted or unsubstituted C6 to C18 arylene group, and a and b are independently integers ranging from 1 to 3.

In one example, all of X ¹ to X ^{3 of} Chemical Formulas 1-1 to 1-3 may be N.

In one example, X ¹ and X ^{3 of} Chemical Formulas 1-1 to 1-3 may be N, and X ² may be CH.

In one example, X ¹ and X ^{2 of} Chemical Formulas 1-1 to 1-3 may be N, and X ³ may be CH.

In one example, X ² and X ^{3 of} Chemical Formulas 1-1 to 1-3 may be N, and X ¹ may be CH.

In one example, X ^{1 of} Chemical Formulas 1-1 to 1-3 may be N, and X ² and X ³ may be CH.

In one example, X ^{2 of} Chemical Formulas 1-1 to 1-3 may be N, and X ¹ and X ³ may be CH.

In one example, X ^{3 of} Chemical Formulas 1-1 to 1-3 may be N, and X ¹ and X ² may be CH.

In one example, Ar ^{1 of} Chemical Formulas 1-1 to 1-3 may be phenyl, naphthyl, biphenyl, triphenyl, or fluorenyl.

In one example, L ¹ and L ^{2 of} Chemical Formulas 1-1 to 1-3 may be single bonds.

In one example, L ^{1 of} Chemical Formulas 1-1 to 1-3 may be a single bond, L ² is a phenylene group, or L ² may be a single bond and L ¹ may be a phenylene group.

In one example, L ¹ and L ^{2 of} Chemical Formulas 1-1 to 1-3 may be phenylene.

As shown in Chemical Formulas 1-1 to 1-3, when the nitrogen-containing heterocyclic group is contained in the dibenzofuranyl group or the dibenzothienyl group at the 3rd position directly connected without a substituent of the linker The best effect of reducing the driving voltage of the organic light emitting diode manufactured by applying the compound and increasing the life of the organic light emitting diode is because the LUMO electron cloud is positioned on a plane and The effect of expanding the electron cloud is maximized. However, when the nitrogen-containing heterocyclic group is not attached at the 3rd position of the dibenzofuran or dibenzothiophene, but is attached at the other position of the dibenzofuran or dibenzothiophene, or via an arylene linker When linked to dibenzofuran or dibenzothiophene, the effect of lowering the driving voltage due to the expansion of the LUMO electron cloud can be reduced.

In Chemical Formula 1, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group.

The substituted or unsubstituted C6 to C30 aryl group of Chemical Formula 1 may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted Or unsubstituted phenanthrene, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl Group, substituted or unsubstituted tetraphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenyl, and substituted Or unsubstituted fluorenyl, such as phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl Or p-terphenyl.

Specifically, Ar ^{1 of} Chemical Formula 1 may be a substituted or unsubstituted C6 to C30 aryl group, preferably a substituted or unsubstituted C6 to C18 aryl group, and more preferably a substituted or unsubstituted C6 to C12 aryl. For example, Ar ¹ according to an embodiment may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted P-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted ortho-terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, A substituted or unsubstituted bitriphenylene group, or a substituted or unsubstituted fluorenyl group, for example, is phenyl, naphthyl, biphenyl, or terphenyl.

More specifically, in the exemplary embodiment of the present invention, Ar ¹ may be phenyl, p-biphenyl, m-biphenyl, p-terphenyl, p-terphenyl, ortho-terphenyl, etc., But it is not limited to this.

Herein, in the substituted aryl group of Ar ¹ , "substituted" means that at least one hydrogen is replaced with deuterium, a C1 to C20 alkyl group, or a C6 to C30 aryl group. For example, "substituted" means that at least one hydrogen is replaced with deuterium, C1 to C10 alkyl, or C6 to C18 aryl, for example, at least one hydrogen is replaced with deuterium, C1 to C4 alkyl, or C6 to C12 aryl .

L ¹ and L ^{2 of} Chemical Formula 1 may be independently a single bond, or a substituted or unsubstituted C6 to C30 aryl group, and preferably a single bond or a substituted or unsubstituted C6 to C18 Shenfang. For example, the linker, L ¹ and L ² according to an embodiment may independently be a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted phenylene, substituted or unsubstituted Substituted naphthyl, substituted or unsubstituted para-terphenyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted ortho-terphenyl, substituted or unsubstituted Substituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted extended terphenyl, or substituted or unsubstituted fluorenyl.

More specifically, in the exemplary embodiment of the present invention, L ¹ and L ² may be independently a single bond, a phenyl group, a p-biphenyl group, a m-biphenyl group, and the like, but are not limited thereto.

In an exemplary embodiment of the present invention, Ar ^{1 of} Chemical Formula 1 may be phenyl, naphthyl, biphenyl, terphenyl, or fluorenyl, and L ¹ and L ² may be independently a single bond, phenyl, or Biphenyl, and may be represented by, for example, Chemical Formula 1-a to Chemical Formula 1-d.

[Chemical Formula 1-a]

[Chemical Formula 1-b]

[Chemical Formula 1-c]

[Chemical Formula 1-d]

In Chemical Formulas 1-a to 1-d, X ¹ to X ^{3 are} independently N or CR ^a , at least one of X ¹ to X ³ is N, Y is O or S, n1, n2, m, and k is independently an integer ranging from 0 to 2, R ^a and R ¹ to R ^{14 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 To C18 aryl, or a combination thereof, and adjacent groups, ie, R ¹³ and R ¹⁴ are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring.

In one example, the adjacent groups of Chemical Formula 1-a and Chemical Formula 1-b, ie, R ¹³ and R ¹⁴ are connected to form a naphthyl group, an anthryl group, a phenanthryl group, a bitriphenylene group, or a fluorenyl group.

In one example, m of Chemical Formula 1-b and Chemical Formula 1-d may be 1, and k may be 0.

In one example, m of Chemical Formula 1-b and Chemical Formula 1-d may be 2, and k may be 0.

In one example, n1 and n2 of Chemical Formulas 1-a to 1-d may be independently 0 or 1.

In one example, all of n1 and n2 of Chemical Formulas 1-a to 1-d may be independently 0. R ¹ to R ^{12 of} Chemical Formula 1 may be independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, preferably hydrogen , Deuterium, unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C18 aryl, or a combination thereof, and more preferably hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl , Substituted or unsubstituted C6 to C12 aryl, or a combination thereof.

Specifically, R ⁹ to R ^{12 of} Chemical Formula 1 may be independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C18 aryl, or a combination thereof, And it is preferably hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C12 aryl, or a combination thereof. For example, R ⁹ to R ¹² according to the embodiment may be independently hydrogen, deuterium, methyl, ethyl, propyl, n-butyl, second butyl, third butyl, isobutyl, phenyl Or a combination.

Specifically, R ¹ to R ^{4 of} Chemical Formula 1 may be independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C18 aryl, or a combination thereof, And it is preferably hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C12 aryl, or a combination thereof. For example, R ¹ to R ⁴ according to an embodiment may be independently hydrogen, deuterium, methyl, phenyl, or a combination thereof.

Specifically, R ⁵ to R ^{8 of} Chemical Formula 1 may be independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C18 aryl, or a combination thereof, And it is preferably hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C12 aryl, or a combination thereof. For example, R ⁵ to R ⁸ according to an embodiment may be independently hydrogen, deuterium, methyl, phenyl, or a combination thereof.

In one example of the present invention, R ¹ to R ^{12 of} Chemical Formula 1 may be independently hydrogen.

The compound for an organic photovoltaic device represented by Chemical Formula 1 may be, for example, a compound selected from Group 1, but is not limited thereto.

[Group 1]

The first compound for an organic photovoltaic device may be applied to the organic photovoltaic device, and may be applied to the organic photovoltaic device alone or together with other compounds for the organic photovoltaic device. When a compound for an organic photovoltaic device is applied together with other compounds for an organic photovoltaic device, the compound may be applied in the form of a composition.

Hereinafter, an example of a composition for an organic photovoltaic device including a first compound for an organic photovoltaic device will be described.

A composition for an organic photovoltaic device according to another embodiment of the present invention includes a first compound for an organic photovoltaic device and a second compound for an organic photovoltaic device represented by Chemical Formula 2.

[Chemical Formula 2]

In Chemical Formula 2, L ³ and L ^{4 are} independently a single bond, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 aryl group, or a combination thereof, Ar ² and Ar ^{3 are} independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and R ²¹ to R ^{26 are} independently hydrogen, deuterium, Substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof, l is between 0 and One of the integers of 2, and "substituted" means that at least one hydrogen is replaced with deuterium, C1 to C4 alkyl, C6 to C18 aryl, or C2 to C30 heteroaryl.

In an exemplary embodiment of the present invention, L ² and L ^{3 of} Chemical Formula 2 may be independently a single bond or a substituted or unsubstituted C6 to C18 arylene group.

In an exemplary embodiment of the present invention, Ar ² and Ar ^{3 of} Chemical Formula 2 may be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridyl, substituted or Unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted isoquinazolinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted Substituted dibenzofuranyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted An azole group, a substituted or unsubstituted fluorenyl group, or a combination thereof.

In an exemplary embodiment of the present invention, Ar ² and Ar ^{3 of} Chemical Formula 2 may be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridyl, substituted or Unsubstituted quinazolinyl, substituted or unsubstituted isoquinazolinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted Or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, or a combination thereof.

In an exemplary embodiment of the present invention, Ar ² and Ar ^{3 of} Chemical Formula 2 may be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenyl, or a combination thereof .

In one example, R ²¹ to R ^{26 of} Chemical Formula 2 may be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. For example, R ²¹ to R ^{26 of} Chemical Formula 2 may be independently Is hydrogen or deuterium.

In one example, l of Chemical Formula 2 may be 0 or 1, and l may be, for example, 0.

In a specific exemplary embodiment of the present invention, * -L ³ -Ar ² and * -L ⁴ -Ar ³ are one of the substituents of Group II, and Chemical Formula 2 is among the substituents including Group II Compounds bonded to one of the structures of group I.

[Group I] [Group II]

In groups I and II, * is the connection point.

The second compound for an organic photovoltaic device represented by Chemical Formula 2 may be, for example, a compound selected from Group 2.

[Group 2]

The first host compound and the second host compound can be combined in various ways to prepare various compositions.

The composition according to the exemplary embodiment of the present invention includes a compound represented by Chemical Formula 1-1 or Chemical Formula 1-2 as a first host, and includes the following compound as a second host: wherein L ² and L ³ in Chemical Formula 2 are independently Is a single bond, substituted or unsubstituted C6 to C30 aryl; Ar ² and Ar ^{3 are} independently substituted or unsubstituted C6 to C30 aryl; R ²¹ to R ^{26 are} independently hydrogen and deuterium , Substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl; and l is 0.

The composition according to the exemplary embodiment of the present invention may include a compound represented by Chemical Formula 1-1 or Chemical Formula 1-2 as a first host, and include Chemical Formula E-31, Chemical Formula E-99, Chemical Formula E- A compound represented by one of 129 and Chemical Formula E-140 serves as a second host.

The second compound used in the organic photoelectric device is used in the light emitting layer together with the first compound used in the organic photoelectric device, and the charge mobility and stability can be improved, and the light emitting efficiency and life characteristics can be improved by this. In addition, the ratio of the second compound for the organic photovoltaic device to the first compound for the organic photovoltaic device can be adjusted, and thereby the charge mobility can be controlled.

For example, it may include a weight ratio of about 1: 9 to 9: 1, specifically a weight ratio of 2: 8 to 8: 2, 3: 7 to 7: 3, 4: 6 to 6: 4, or 5 : 5 First compound for organic optoelectronic devices and second compound for organic optoelectronic devices, and may include, for example, a first compound for organic optoelectronic devices and organic optoelectronic devices of 3: 7 Of the second compound. In addition, a first compound for an organic photovoltaic device and a second compound for an organic photovoltaic device may be used in a weight ratio of 1: 1 to 1: 4, 1: 1 to 1: 3, or 1: 1 to 4: 6. .

Within this range, both efficiency and life can be improved.

The composition may further include one or more organic compounds in addition to the first compound for an organic photovoltaic device and the second compound for an organic photovoltaic device.

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

The dopants are mixed in small amounts to cause light emission, and may be generally a material that emits light by being excited to the triplet state or more than multiple times, such as a metal complex. The dopant may be, for example, an inorganic compound, an organic compound, or an organic / inorganic compound, and one or more kinds thereof may be used.

The dopant may be, for example, a phosphorescent dopant, and examples of the phosphorescent dopant may include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd Or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[Chemical Formula Z] L ₂ MX

In the chemical formula Z, M is a metal, and L and X are the same or different, and are ligands forming a complex compound with M.

M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L and X may be, for example, bidentate ligands.

Hereinafter, an organic photovoltaic device including a compound for an organic photovoltaic device or a composition for an organic photovoltaic device is described.

An organic photovoltaic device according to another embodiment includes an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the compound for an organic photovoltaic device or the for Composition of organic photovoltaic device.

For example, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound for an organic photovoltaic device or the composition for an organic photovoltaic device of the present invention.

Specifically, the compound for an organic photovoltaic device or the composition for an organic photovoltaic device may be included as a host (for example, a green host) of the light emitting layer.

In addition, the organic layer may include a light emitting layer and at least one auxiliary layer, and the at least one auxiliary layer is selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and a hole blocking layer The auxiliary layer may include the compound for an organic photovoltaic device or the composition for an organic photovoltaic device.

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

In an exemplary embodiment of the present invention, the compound for an organic photoelectric device included in the electron transport auxiliary layer may be represented by Chemical Formula 1-I, Chemical Formula 1-a, or Chemical Formula 1-c.

The organic photoelectric device may be any device that converts electrical energy into light energy and vice versa, but is not particularly limited, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

Herein, an organic light emitting diode as an example of an organic photovoltaic device is explained with reference to the drawings.

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

Referring to FIG. 1, an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110, 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 large work function to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal, nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, or indium tin oxide (ITO) , Indium zinc oxide (IZO), etc .; metal and oxide combinations, such as ZnO and Al or SnO ₂ and Sb; conductive polymers, such as poly (3-methylthiophene), poly [3,4- Poly (3,4- (ethylene-1,2-dioxy) thiophene) (PEDT), polypyrrole, and polyaniline are not limited thereto.

The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, thallium, aluminum, silver, tin, lead, cesium, barium, and the like; -layer) structural materials such as LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca, but it is not limited to this.

The organic layer 105 includes a light emitting layer 130 including a compound for an organic photoelectric device or a composition for an organic photoelectric device.

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

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

Although the following layers are not shown, the organic layer 105 shown in FIG. 1 or FIG. 2 may further include an electron injection layer, an electron transport layer, an electron transport auxiliary layer, a hole transport layer, a hole transport auxiliary layer, a hole injection layer, or Its combination. These organic layers may include the compound for an organic photovoltaic device or the composition for an organic photovoltaic device of the present invention. The organic light emitting diode 100 and the organic light emitting diode 200 can be manufactured by forming an anode or a cathode on a substrate; using, for example, a vacuum deposition method (evaporation), sputtering, plasma, or plasma plating. forming an organic layer by a dry film forming method such as plating and ion plating, or a wet coating method such as spin coating, dipping, and flow coating; and on the organic layer Form a cathode or anode.

The organic light emitting diode can be applied to an organic light emitting diode display.

Hereinafter, embodiments will be described in more detail with reference to examples. However, these examples should not be construed as limiting the scope of the invention in any sense.

In the following, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd. and Apichemical Co. Ltd.) or TCI Inc., or synthesized by known methods. (Preparation of compounds for organic photovoltaic devices)

A compound as a specific example of the present invention was synthesized by the following steps. Synthesis of Compound [1]: (first compound for an organic photoelectric device) Synthesis Example 1

[Reaction Scheme 1] First step: Synthesis of intermediate A

Under a nitrogen atmosphere, 2,4-dichloro-6-phenyl-1,3,5-triazine (50.55 g, 223.59 mmol) and dibenzofuran-3-ylboronic acid (40.3 g, 190.06 mmol) Mol) was dissolved in 900 ml of tetrahydrofuran in a 2-liter round-bottom flask, and tetrakis (triphenylphosphine) palladium (12.9 g, 11.18 mmol) was added thereto, and the mixture was stirred. A saturated aqueous solution of potassium carbonate (61.8 g, 447.19 mmol) was added thereto, and the obtained mixture was heated and refluxed at 80 ° C for 12 hours. When the reaction was completed, the organic layer was separated, treated with anhydrous MgSO ₄ to remove water, filtered, and concentrated under reduced pressure. The obtained residue was crystallized using dichloromethane and hexane to obtain 35.3 g (44%) of Intermediate A. Second step: Synthesis of intermediate B

To 240 ml of N, N-dimethylformamide (DMF) in a 1 liter round bottom flask was added 3-bromocarbazole (7.4 g, 29.96 mmol), the mixture was stirred, To this was slowly added sodium hydride (60%, mineral oil, 2.4 g, 59.92 mmol). After 30 minutes, Intermediate A (12.6 g, 35.25 mmol) was slowly added thereto and the resulting mixture was stirred for 12 hours. The reaction product was poured into water, and the solid formed therein was filtered. The obtained residue was solidified using dichlorobenzene and methanol to obtain 17 g (85%) of Intermediate B. Third step: Synthesis of compound [1]

Intermediate B (16.5 g, 29.06 mmol), carbazole (5.8 g, 34.88 mmol) and sodium tert-butoxide (5.6 g, 58.13 mmol) were dissolved in 50 ml of xylene, and To this were added dropwise palladium (diphenylmethyleneacetone) (0.836 g, 1.45 mmol) and a third butylphosphine (1.41 g, 2.91 mmol, 50% toluene mixture). The reaction solution was heated and stirred under a nitrogen stream at 120 ° C. After the reaction was completed, methanol was poured into the reaction product, and the solid produced therein was filtered and dissolved in dichlorobenzene. Activated carbon and anhydrous magnesium sulfate were added thereto, and the obtained mixture was subjected to It was stirred, filtered, and recrystallized using dichlorobenzene and methanol to obtain 16 g (84%) of the compound [1]. Liquid chromatography (liquid chromatography, LC) mass (theoretical value: 653.73 g / mole, measured value: M ⁺ H + = 654.22 g / mole) Synthesis Example 2: Compound [40] Synthesis of

[Reaction Scheme 2] First step: Synthesis of intermediate C

According to the same method as the synthesis method of intermediate A, 2,4-dichloro-6-phenyl-1,3,5-triazine (42.3 g, 187.24 mmol) and benzothiophen-3-ylboronic acid were used. (36.3 grams, 159.15 millimoles) 30 grams (43%) of Intermediate C were obtained. Second step: Synthesis of intermediate D

According to the same method as the method of synthesizing intermediate B, 16 g (80%) of intermediate D was obtained using 3-bromocarbazole (7.17 g, 29.13 mmol) and intermediate C (12.8 g, 34.28 mmol). . Third step: Synthesis of compound [40]

According to the same method as the method for synthesizing compound [1], 13 g (76%) of compound [40] was obtained using intermediate D (14.8 g, 25.38 mmol) and carbazole (5.1 g, 30.46 mmol). Synthesis of Compound [2]: liquid chromatography mass (theoretical value: 669.79 g / mole, measured value: M ⁺ H + = 670.20 g / mole) Synthesis Example 3

[Reaction Scheme 3] First step: Synthesis of intermediate E

According to the same method as the method for synthesizing Compound [1], 17 g (85%) of intermediate was obtained using 2-bromocarbazole (7.4 g, 29.96 mmol) and intermediate A (12.61 g, 35.25 mmol). E. Second step: Synthesis of compound [2]

According to the same method as the method for synthesizing compound [1], 14 g (82%) of compound [2] was obtained using intermediate E (14.756 g, 26 mmol) and carbazole (5.22 g, 31.21 mmol). Liquid chromatography mass (theoretical value: 653.73 g / mole, measured value: M ⁺ H + = 654.22 g / mole) Synthesis Example 4: Compound [41] Synthesis of

[Reaction Scheme 4] First step: Synthesis of intermediate F

According to the same method as the synthesis method of intermediate B, 16 g (80%) of intermediate F was obtained using 2-bromocarbazole (7.2 g, 29.13 mmol) and intermediate C (12.81 g, 34.28 mmol). . Second step: Synthesis of compound [41]

According to the same method as the method for synthesizing compound [1], 13 g (81%) of compound [41] was obtained using intermediate F (13.9 g, 23.9 mmol) and carbazole (4.8 g, 28.67 mmol). Liquid chromatography quality (theoretical value: 669.79 g / mole, measured value: M + H ⁺ = 670.20 g / mole) Comparative Synthesis Example 1 : Comparative Compound 1

[Reaction Scheme 5]

Comparative compound 1 was synthesized by the same method as the method for synthesizing compound [1]. Mass of liquid chromatography (theoretical value: 563.65 g / mole, measured value: M + H ⁺ = 564.21 g / mole) (manufacturing of organic light-emitting diodes: light-emitting layer device 1 ) Example 1

An organic light-emitting diode was manufactured using the compound [1] obtained in Synthesis Example 1 as a host and Ir (PPy) ₃ as a dopant.

For the anode, 1000 angstrom indium tin oxide was used, and for the cathode, 1000 angstrom aluminum was used. Specifically, a method for manufacturing an organic light emitting diode is described. An anode is manufactured by cutting an indium tin oxide glass substrate having a sheet resistance of 15 ohm / cm 2 into a size of 50 mm × 50 mm × 0.7 mm It was subjected to ultrasonic cleaning for 15 minutes in each of acetone, isopropanol, and pure water, and it was subjected to ultraviolet ozone cleaning for 30 minutes.

On the substrate, N4, N4'-bis (naphthalene-1-yl) -N4, N4 was deposited at a deposition rate of 0.1 nm / sec to 0.3 nm / sec under a vacuum of 650 × 10 ^-7 Pa. '-Diphenylbiphenyl-4,4'-diamine (NPB) (80 nm) was deposited to form a 800 Angstrom hole transport layer. Subsequently, a 300 Angstrom thick light emitting layer was formed using the compound [1] of Synthesis Example 1 under the same vacuum deposition conditions, and a phosphorescent dopant Ir (PPy) 3 was simultaneously deposited. Herein, a phosphorescent dopant is deposited to 7% by weight based on 100% by weight of the total weight of the light-emitting layer by adjusting the deposition rate.

On the light-emitting layer, a 50 Angstrom electrode was formed by depositing bis (2-methyl-8-hydroxyquinoline) -4- (phenylphenol) aluminum (BAlq) under the same vacuum deposition conditions. Hole barrier. Subsequently, a 200 Angstrom thick electron transport layer was formed by depositing Alq3 under the same vacuum deposition conditions. On the electron transport layer, a cathode was formed by sequentially depositing LiF and Al to manufacture an organic light emitting diode.

The structure of the organic light emitting diode is ITO / NPB (80 nm) / EML (compound [1] (93% by weight) + Ir (PPy) ₃ (7% by weight), 30nm) / Balq (5nm ) / Alq3 (20nm)) / LiF (1nm) / Al (100nm). Example 2 and Example 3

Each of the compounds according to Example 2 and Example 3 was produced according to the same method as Example 1 except that Compound [40] of Synthesis Example 2 and Compound [2] of Synthesis Example 3 were used instead of Compound [1] of Synthesis Example 1. Organic light emitting diode. Comparative Example 1 and Comparative Example 2

Instead of using Comparative Compound 1 and 4,4'-bis (N-carbazolyl) -1,1'-biphenyl (CBP, CAS No. 58328-31-7) in Comparative Synthesis Example 1, respectively, Except for the compound [1], each organic light-emitting diode according to Comparative Examples 1 and 2 was manufactured by the same method as in Example 1. Evaluation 1 : Evaluation of the characteristics of an organic light emitting diode

The current density change, brightness change, and luminous efficiency according to the apparent voltage of each organic light emitting diode of Examples 1 to 3 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1. .

The specific measurement method is as follows. (1) Measurement of current density change depending on voltage change

Regarding the value of the current flowing into the unit device, the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400) when the voltage was increased from 0 volts to 10 volts, and the measured Divide the current value by the area to get the result. (2) Measurement of brightness change depending on voltage change

A brightness meter (Minolta Cs-1000A) was used to measure the brightness when the voltage of the organic light emitting diode increased from 0 volts to 10 volts. (3) Measurement of luminous efficiency

The brightness, current density, and voltage (volts) from items (1) and (2) were used to calculate the current efficiency (candela / amp) at the same current density (10 mA / cm2).

(Table 1)

Referring to Table 1, the organic light emitting diodes according to Examples 1 to 3 showed improved driving voltage and light emitting efficiency compared to the organic light emitting diodes according to Comparative Examples 1 and 2. The reason is that the compounds of Examples 1 to 3 include a carbazolyl-substituted carbazole and also a triazine located at N of the carbazolyl group and directly connected to a dibenzofuran or dibenzothiophene without a linker, and As the LUMO electron cloud expands, the driving voltage is reduced. (Manufacture of organic light-emitting diodes: light-emitting layer device 2 )

The second compounds E-31, E-99, E-129, and E-140 for organic photovoltaic devices were synthesized by a known method.

[E-31] [E-99] [E-129] [E-140] Example 4

A glass substrate coated with indium tin oxide (ITO) to be a thin film of 1500 angstroms was washed with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed and dried with a solvent such as isopropanol, acetone, and methanol, and then moved to a plasma cleaner, cleaned with an oxygen plasma for 10 minutes, and moved to Vacuum depositor. Using the obtained indium tin oxide transparent electrode as an anode, compound A was vacuum-deposited on an indium tin oxide substrate to form a 700 angstrom hole injection layer, and compound B was deposited on the injection layer to a thickness of 50 angstroms. Compound C was deposited to a thickness of 1020 Angstroms to form a hole transport layer. By simultaneously vacuum-depositing the compound [1] and the compound E-31 of Synthesis Example 1 as a host and depositing 10% by weight of tris (2-phenylpyridine) iridium (III) [Ir (ppy) ₃ ] as a dopant, A 400 Angstrom thick light emitting layer was formed on the hole transport layer. Herein, the compound [1] and the compound E-31 are used in a weight ratio of 5: 5, and the ratios of the compound [1] and the compound E-31 in the following examples are separately explained.

Subsequently, compounds D and Liq were simultaneously vacuum-deposited on the light-emitting layer at a ratio of 1: 1 to form a 300 angstrom thick electron transport layer, and Liq was vacuum-deposited to 15 angstroms thick and Al was vacuum deposited to a thickness of 1200 Angstroms to form a cathode, thereby fabricating an organic light emitting diode.

The organic light emitting diode has the following five-layer organic thin layer.

ITO / Compound A (700 Angstroms) / Compound B (50 Angstroms) / Compound C (1,020 Angstroms) / EML [Compound [1]: E-31: Ir (ppy) ₃ = 27% by weight: 63% by weight: 10% by weight %] (400 Angstroms) / Compound D: Liq (300 Angstroms) / Liq (15 Angstroms) / Al (1,200 Angstroms).

Compound A: N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4,4'-diamine

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-3-yl) phenyl) -9H-fluorene- 2-amine

Compound D: 8- (4- (4,6-bis (naphthalene-2-yl) -1,3,5-triazin-2-yl) phenyl) quinoline Examples 5 to 14 and Comparative Examples 3 to Comparative Example 6

The organic light-emitting diodes according to Examples 5 to 14 and Comparative Examples 3 to 6 were manufactured by using the same method as Example 4 as shown in Table 2 using the first body and the second body, respectively.

Evaluation 2 : Evaluation of the characteristics of organic light emitting diodes

The luminous efficiency and lifetime characteristics of each organic light emitting diode according to Examples 4 to 14 and Comparative Examples 3 to 6 were evaluated, and the results are shown in Table 2.

The specific measurement method is as follows. (1) Measurement of current density change depending on voltage change

Regarding the value of the current flowing into the unit device, the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400) when the voltage was increased from 0 volts to 10 volts, and the measured Divide the current value by the area to get the result. (2) Measurement of brightness change depending on voltage change

A brightness meter (Minolta Cs-1000A) was used to measure the brightness when the voltage of the organic light emitting diode increased from 0 volts to 10 volts. (3) Measurement of luminous efficiency

The current efficiency (Candela / A) at the same current density (10 mA / cm 2) was calculated by using the brightness, current density, and voltage (volts) from items (1) and (2). (4) Measurement of life

The life was obtained by measuring the time taken until the current efficiency (Candela / A) was reduced to 97% while maintaining the brightness (Candela / m2) at 6000 Candela / m2.

(Table 2)

Referring to Table 2, the organic light emitting diodes according to Examples 4 to 14 showed significantly deteriorated light emitting efficiency and lifetime characteristics compared to the organic light emitting diodes according to Comparative Examples 3 to 6. As described above, the reason is that the compounds used in Examples 4 to 14 include substituents which are directly attached to the nitrogen-containing heterocyclic group at the 3rd position of dibenzofuran or dibenzothiophene without the need for a linker, and therefore It has a structure that easily accepts electrons when the LUMO electron cloud expands when an electric field is applied, and thus the driving voltage is reduced.

Specifically, Comparative Example 3 using a CBP compound as a first host compound, and Comparative Examples 4 and 5 using a second host compound, compared to an organic light emitting diode according to an exemplary embodiment of the present invention, High driving voltage and significantly low luminous efficiency and lifetime. In addition, when the first body and the second body according to the exemplary embodiment of the present invention are used, as compared to the case where the same second body is used according to Comparative Example 6, but a diphenyl having no direct substitution with a nitrogen-containing heterocyclic group is used The organic light-emitting diodes of the comparative compound 1 of benzofuran or dibenzothiophene as the first host, the organic light-emitting diodes according to Examples 4 to 14 showed a lifespan increase of up to 4 times.

Although the present invention has been described in conjunction with exemplary embodiments that are presently considered practical, it should be understood that the invention is not limited to the disclosed embodiments, but instead is intended to cover the spirit and scope included within the scope of the accompanying patent application Various retouching and equivalent configurations. Therefore, it should be understood that the above-mentioned embodiments are exemplary and do not limit the present invention in any way.

100, 200‧‧‧ organic light-emitting diodes

105‧‧‧ organic layer

110‧‧‧ cathode

120‧‧‧Anode

130‧‧‧Light-emitting layer

140‧‧‧Electric hole auxiliary layer

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

Claims (14)

A compound for an organic photovoltaic device, represented by Chemical Formula 1: [Chemical Formula 1] Wherein, in Chemical Formula 1, X ¹ to X ^{3 are} independently N or CR ^a , at least one of X ¹ to X ³ is N, Y is O or S, and Ar ¹ is substituted or unsubstituted C6 To C30 aryl, R ^a and R ¹ to R ^{12 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, L ¹ and L ^{2 are} independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group, and a and b are independently an integer ranging from 1 to 3. As the compound for an organic photovoltaic device according to item 1 of the scope of application for a patent, the compound for an organic photovoltaic device is represented by Chemical Formula 1-1 to Chemical Formula 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] Among them, in Chemical Formulae 1-1 to 1-3, X ¹ to X ^{3 are} independently N or CR ^a , at least one of X ¹ to X ³ is N, and Ar ¹ is substituted or unsubstituted C6 to C30 aryl, Y is O or S, R ^a and R ¹ to R ^{12 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 An aryl group, or a combination thereof, L ¹ and L ^{2 are} independently a single bond, or a substituted or unsubstituted C6 to C18 aryl group, and a and b are independently integers ranging from 1 to 3. As the compound for an organic photovoltaic device according to item 1 of the scope of application for a patent, the compound for an organic photovoltaic device is represented by Chemical Formula 1-a or Chemical Formula 1-b: [Chemical Formula 1-a] [Chemical Formula 1-b] [Chemical Formula 1-c] [Chemical Formula 1-d] Wherein, in Chemical Formulas 1-a to 1-d, X ¹ to X ^{3 are} independently N or CR ^a , at least one of X ¹ to X ³ is N, Y is O or S, n1, n2, m and k are independently integers ranging from 0 to 2, R ^a and R ¹ to R ^{14 are} independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C18 aryl, or a combination thereof, and R ¹³ and R ¹⁴ exist independently or are connected to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring. The compound for an organic photovoltaic device according to item 1 of the scope of patent application, wherein Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted Naphthyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted anthryl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenylene, or substituted or unsubstituted fluorenyl. The compound for an organic photovoltaic device according to item 1 of the scope of the patent application, wherein L ¹ and L ^{2 are} independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted extender Phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted para-terphenyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted ortho-terphenyl Phenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted extrinyl, or substituted or unsubstituted fluorenyl . As the compound for an organic photovoltaic device according to item 1 of the scope of patent application, the compound for an organic photovoltaic device is selected from the compounds of group 1: [group 1] . A composition for an organic photovoltaic device, comprising the first compound for an organic photovoltaic device as described in item 1 of the scope of patent application; and a second compound for an organic photovoltaic device, represented by Chemical Formula 2: [Chemical Formula 2 ] Wherein, in Chemical Formula 2, L ³ and L ^{4 are} independently a single bond, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 aryl group, or a combination thereof Ar ² and Ar ^{3 are} independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R ²¹ to R ^{26 are} independently hydrogen, Deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof, l is between An integer in the range of 0 to 2, and the "substituted" means that at least one hydrogen is replaced with deuterium, C1 to C4 alkyl, C6 to C18 aryl, or C2 to C30 heteroaryl. The composition for an organic photovoltaic device according to item 7 of the scope of patent application, wherein Ar ² and Ar ^{3 of} Chemical Formula 2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group Base, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted Substituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, Substituted or unsubstituted quinazolinyl, substituted or unsubstituted isoquinazolinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl , Substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, or a combination thereof. The composition for an organic photovoltaic device according to item 7 of the scope of patent application, wherein each of * -L ³ -Ar ² and * -L ⁴ -Ar ³ of Chemical Formula 2 is a substituent of group II And the second compound for an organic optoelectronic device is a compound containing one of the substituents of group II that is bonded to one of the structures of group I: [group I] [Group II] Among them, in group I and group II, * is the connection point. An organic photovoltaic device includes an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes any one of items 1 to 6 of a patent application range. A compound for an organic photovoltaic device according to one item; or a composition for an organic photovoltaic device according to any one of claims 7 to 9 of the scope of patent application. The organic photovoltaic device according to claim 10, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound for an organic photovoltaic device or the composition for an organic photovoltaic device. The organic photovoltaic device according to item 11 of the scope of patent application, wherein the compound for an organic photovoltaic device or the composition for an organic photovoltaic device is used as a host of the light emitting layer. The organic photovoltaic device according to item 11 of the scope of patent application, wherein the organic layer includes at least one auxiliary layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection. Layer and hole blocking layer, and the auxiliary layer further includes an electron transport auxiliary layer adjacent to the light emitting layer, and the electron transport auxiliary layer includes the compound for an organic photoelectric device or the organic Composition of photovoltaic device. A display device includes the organic photoelectric diode according to item 10 of the scope of patent application.