KR20110102055A - Compound for organic photoelectric device and organic photoelectric device including the same - Google Patents

Abstract

상기 화학식 1에서 A¹ 내지 A³, X¹, R¹ 및 R²의 정의는 명세서에 기재된 바와 같다. 상기 유기광전소자용 화합물을 이용하면, 낮은 구동전압을 가지며, 열적/전기화학적 안정성 및 수명, 효율이 우수한 유기광전소자를 제공할 수 있다.The present invention relates to a compound for an organic photoelectric device and an organic photoelectric device including the same, wherein the compound for an organic photoelectric device is represented by the following Chemical Formula 1.
[Formula 1]

Definitions of A ¹ to A ³ , X ¹ , R ^1, and R ² in Chemical Formula 1 are as described in the specification. By using the compound for an organic photoelectric device, it is possible to provide an organic photoelectric device having a low driving voltage and excellent thermal / electrochemical stability, lifetime, and efficiency.

Description

Compound for organic photoelectric device and organic photoelectric device including same

The present invention relates to a compound for an organic photoelectric device and an organic photoelectric device including the same, which can provide an organic photoelectric device having excellent lifetime, efficiency, electrochemical stability, and thermal stability.

An organic photoelectric device refers to a device that requires charge exchange between an electrode and an organic material using holes or electrons.

The organic photoelectric device may be classified into two types according to the operation principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.

The second is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

Examples of the organic photoelectric device include an organic photoelectric device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which are used to inject or transport holes, or inject or transport materials for driving the device. Or a luminescent material.

In particular, organic light emitting diodes (OLEDs) are attracting attention as the demand for flat panel displays increases. In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

Such an organic photoelectric device is a device that converts electrical energy into light by applying a current to an organic light emitting material and has a structure in which a functional organic material layer is inserted between an anode and a cathode. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic photoelectric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.

When the voltage is applied between the two electrodes in the structure of the organic photoelectric device, holes are injected into the organic material layer in the anode and electrons in the cathode, and the injected holes and the electrons meet and recombine by recombination. High energy excitons are formed. At this time, the excitons formed are moved to the ground state, and light having a specific wavelength is generated.

In 1987, Eastman Kodak developed the first organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer (Appl. Phys. Lett. 51, 913, 1987). For the light emitting device, CW Tang et al. Reported the first practical device in 1987 (Applied Physics Letters, 51 (12), 913-915, 1987).

This document describes a structure in which a thin film of a diamine derivative (hole transport layer) and a thin film of tris (8-hydroxy-quinolate) aluminum (Alq ₃ ) are laminated as an organic layer.

Recently, phosphorescent as well as fluorescent light emitting materials can be used as light emitting materials for organic photoelectric devices (DFO'Brien et al., Applied Physics Letters, 74 (3), 442-444, 1999; MA Baldo et al. , Applied Physics letters, 75 (1), 4-6, 1999), and these phosphorescent luminescences are transferred to the excited state from the ground state to the excited state, and then through intersystem crossing The anti-exciter is non-luminescent transition into triplet excitons, and then the triplet excitons are made to emit light while transitioning to the ground state.

As described above, the material used as the organic material layer in the organic photoelectric device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.

In addition, the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. In order to increase luminous efficiency and stability through the host / dopant system can be used as a light emitting material.

In order for the organic photoelectric device to fully exhibit the above-mentioned excellent features, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc. Supported by this stable and efficient material should be preceded, and development of a stable and efficient organic material layer material for an organic photoelectric device has not been made yet, and therefore, development of new materials is continuously required. The need for such a material development is the same for the other organic photoelectric devices described above.

In addition, the low molecular organic photoelectric device is manufactured in the form of a thin film by vacuum deposition method, so the efficiency and life performance is good, and the polymer organic light emitting device uses the inkjet or spin coating method and the initial investment cost is low. Large area has an advantage.

Both low-molecular organic photoelectric devices and high-molecular organic photoelectric devices have attracted attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range. Compared with crystal display, it is self-luminous type, so it is good for cyanity even in the dark or outside light, and it can reduce thickness and weight by 1/3 of LCD because it does not need backlight.

In addition, the response speed is 1000 times faster than the LCD in microseconds, it is possible to implement a perfect video without afterimages. Therefore, it is expected to be spotlighted as the most suitable display in line with the recent multimedia era. Based on these advantages, we have made rapid technological developments with efficiency of 80 times and lifespan over 100 times since the first development in the late 1980s. Increasingly, the organic light emitting device panel has been announced.

In order to increase the size, the luminous efficiency must be increased and the life of the device must be accompanied. In this case, the light emitting efficiency of the device should be smoothly coupled to the holes and electrons in the light emitting layer. However, since the electron mobility of the organic material is generally slower than the hole mobility, in order to efficiently combine holes and electrons in the light emitting layer, an efficient electron transport layer is used to increase the electron injection and mobility from the cathode, It should be able to block the movement of holes.

In addition, in order to improve the life, it is necessary to prevent the material from crystallizing due to Joule heat generated when the device is driven. Therefore, there is a need for development of organic compounds having excellent electron injection and mobility and high electrochemical stability.

Provided are a compound for an organic photoelectric device, which may serve as light emitting, or inject and / or transport electrons and / or holes, and act as a light emitting host with an appropriate dopant.

It is intended to provide an organic photoelectric device having excellent lifespan, efficiency, driving voltage, electrochemical stability and thermal stability, and especially when used in an organic photoelectric device as a light emitting layer or a hole transporting and / or injection layer, the device has a high driving voltage. It can have efficiency characteristics of performance.

In one aspect of the present invention, there is provided a compound for an organic photoelectric device represented by the following formula (1).

[Formula 1]

In Formula 1, A ¹ to A ³ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted electronic property It is selected from the group consisting of a C3 to C30 heteroaryl group and -NR'R ", wherein R 'and R" are the same or different from each other, independently hydrogen, substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted Selected from the group consisting of a substituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, at least one of A ¹ to A ³ is a C3 to C30 heteroaryl group having substituted or unsubstituted electronic properties; , At least one of A ¹ to A ³ is substituted or unsubstituted -NR'R ", wherein R 'and R" are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, Substitution or ratio Hwandoen C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 is selected from a heteroaryl group the group consisting of, R ¹ and R ² are the same or different, are independently hydrogen, substituted or unsubstituted C1 to C6 alkyl group, It is selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, X ¹ is N.

In another aspect, the present invention provides a compound for an organic photoelectric device represented by the following Chemical Formula 2.

 [Formula 2]

In Formula 2, any one of A ⁴ or A ⁵ is a C3 to C30 heteroaryl group having a substituted or unsubstituted electronic property, the other is -NR'R ", and R 'and R" are the same as each other Different and independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, R ³ and R ⁴ Are the same as or different from each other, and are independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, X ² is one selected from the group consisting of O, S and P.

At least one of A ¹ to A ³ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted oxa Triazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrimidines, substituted or unsubstituted Triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted phthalazine, Substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and substituted or It may be selected from the group consisting of substituted phenazine.

Either A ⁴ or A ⁵ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted oxatriazole , Substituted or unsubstituted thiazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzotriazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted tree Azine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted phthalazine, substituted or Unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and substituted or unsubstituted phen It may be selected from the group consisting of Gin.

In another aspect of the present invention, a compound for an organic photoelectric device represented by any one of the following Chemical Formulas 3 to 6 is provided.

[Formula 3] [Formula 4]

[Formula 5] [Formula 6]

In another aspect of the present invention, there is provided a compound for an organic photoelectric device represented by the following formula (7).

[Formula 7]

In Formula 7, R ⁵ and R ⁶ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 Is selected from the group consisting of heteroaryl groups, X ³ is N, A ⁶ to A ⁸ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl Group, a substituted or unsubstituted C3 to C30 heteroaryl group and the following formula S-1 to S-4 is selected from the group consisting of, at least any one of A ⁶ to A ⁸ in the formulas S-1 to S-4 Which one,

Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

R ⁹ to R ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group A ¹¹ and A ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group selected from the group consisting of, X ⁵ is N, wherein X ⁶ is one selected from the group consisting of O, P and S.

At least one of A ⁶ , A ⁷ , A ⁸ , A ^11, or A ¹² may be a substituted or unsubstituted C3 to C30 heteroaryl group.

In another aspect of the present invention, there is provided a compound for an organic photoelectric device represented by the following formula (8).

 [Formula 8]

In Formula 8, R ⁷ and R ⁸ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 Is selected from the group consisting of heteroaryl groups, X ⁴ is one selected from the group consisting of O, P and S, A ⁹ and A ¹⁰ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group , A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group and the following formula S-1 to S-4 is selected from the group consisting of at least any one of A ⁹ or A ¹⁰ Any one of the formulas S-1 to S-4,

Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

R ⁹ to R ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group A ¹¹ and A ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group selected from the group consisting of, X ⁵ is N, wherein X ⁶ is one selected from the group consisting of O, P and S.

At least one of A ⁹ , A ¹⁰ , A ¹¹ or A ¹² may be a substituted or unsubstituted C3 to C30 heteroaryl group.

At least one of A ⁶ , A ⁷ , A ⁸ , A ¹¹ or A ¹² may be substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxa Diazoles, substituted or unsubstituted oxtriazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridine, substituted or unsubstituted Substituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, Substituted or unsubstituted phthalazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline And it may be selected from the group consisting of substituted or unsubstituted phenazine.

At least one of A ⁹ , A ¹⁰ , A ¹¹ or A ¹² may be substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, Substituted or unsubstituted oxtriazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzotriazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyridine Midine, substituted or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted Substituted phthalazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and It may be selected from the group consisting of substituted or unsubstituted phenazine.

In another aspect of the present invention, there is provided a compound for an organic photoelectric device represented by the formula selected from the group consisting of the following formulas 9, 10, 10-H and A-1 to A-39.

[Formula 9] [Formula 10]

[Formula 10-H] [Formula A-1]

[Formula A-2] [Formula A-3]

[Formula A-4] [Formula A-5]

[Formula A-6] [Formula A-7]

[Formula A-8] [Formula A-9]

[Formula A-10] [Formula A-11]

[Formula A-12] [Formula A-13]

[Formula A-14] [Formula A-15]

[Formula A-16] [Formula A-17]

Formula A-18 Formula A-19

Formula A-20 Formula A-21

Formula A-22 Formula A-23

[Formula A-24] [Formula A-25]

Formula A-26 Formula A-27

Formula A-28 Formula A-29

[Formula A-30] [Formula A-31]

Formula A-32 Formula A-33

Formula A-34 Formula A-35

Formula A-36 Formula A-37

Formula A-38 Formula A-39

In another aspect of the invention, there is provided a compound for an organic photoelectric device represented by any one formula selected from the group consisting of the following formula (11), 12 and 13.

[Formula 11]

[Chemical Formula 12]

[Formula 13]

In Formulas 11, 12 and 13, X ¹ is selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R 'is hydrogen, a substituted or unsubstituted C1 to C6 alkyl group , A substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, any one of X ² or X ³ is -CR ⁴ R ^5- , the other is- O-, -P-, -NR'- and -S-, and R ⁴ and R ⁵ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, substituted Or an unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, wherein R 'is hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heteroaryl group selected from the group consisting of A ¹ to A ³ is the same as or different from each other, and is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group; R ¹ to R ³ are the same as or different from each other, and are independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from the group.

At least one of A ¹ to A ³ or R ′ may be a substituted or unsubstituted C 3 to C 30 heteroaryl group.

At least one of A ¹ to A ³ or R ′ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted Substituted oxtriazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrimidines, substitutions Or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted fruc Tallazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and chi Or it may be selected from the group consisting of unsubstituted phenazine.

In another aspect of the present invention, there is provided a compound for an organic photoelectric device represented by any one formula selected from the group consisting of the following formula 14 to 20, 16-H1, 16-H2 and B-1 to B-44.

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Formula 18] [Formula 19]

[Formula 20]

[Formula 16-H1] [Formula 16-H2]

[Formula 16-H1] [Formula 16-H2]

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

[Formula B-3] [Formula B-4]

[Formula B-5] [Formula B-6]

[Formula B-7] [Formula B-8]

[Formula B-9] [Formula B-10]

[Formula B-11] [Formula B-12]

[Formula B-13] [Formula B-14]

[Formula B-15] [Formula B-16]

[Formula B-17] [Formula B-18]

Formula B-19 Formula B-20

Formula B-21 Formula B-22

Formula B-23 Formula B-24

[Formula B-25] [Formula B-26]

Formula B-27 Formula B-28

[Formula B-29] [Formula B-30]

Formula B-31 Formula B-32

[Formula B-33] [Formula B-34]

[Formula B-35] [Formula B-36]

Formula B-37 Formula B-38

[Formula B-39] [Formula B-40]

[Formula B-41] [Formula B-42]

Formula B-43 Formula B-44

In another aspect of the invention, there is provided a compound for an organic photoelectric device represented by the formula (21).

[Formula 21]

In Chemical Formula 21, z is 0 or 1, R ¹ and R ² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substitution Or an unsubstituted C3 to C30 heteroaryl group, X ¹ is selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R 'is hydrogen, substituted or An unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, C ¹ is the following formula S-5, and C ² is Formula S-6,

[Formula S-5] [Formula S-6]

The two * marks of C ¹ are any two adjacent * marks of the four * marks of Formula S-5, and the two * marks of C ² are any two of the four * marks of Formula S-6. * And R ³ to R ⁶ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 Is selected from the group consisting of heteroaryl groups, and X ² and X ³ are the same as or different from each other, and are independently selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R ' Is selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group.

Z may be 1.

Z may be zero.

At least one of R ′ or A ¹ to A ⁴ may be a substituted or unsubstituted C3 to C30 heteroaryl group.

At least one of R 'or A ¹ to A ⁴ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted Substituted oxtriazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrimidines, substitutions Or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted fruc Tallazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and chi Or it may be selected from the group consisting of unsubstituted phenazine.

In another aspect of the present invention, there is provided a compound for an organic photoelectric device represented by the formula selected from the group consisting of the following formula 22 to 31, 22-H and 23-H.

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

[Formula 26] [Formula 27]

[Formula 28] [Formula 29]

[Formula 30] [Formula 31]

[Formula 22-H] [Formula 23-H]

In another aspect of the present invention, in the organic photoelectric device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least one of the organic thin film layer for the above organic photoelectric device It provides an organic photoelectric device comprising a compound.

The organic thin film layer may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.

The compound for an organic photoelectric device may be included in a hole transport layer or a hole injection layer.

The compound for an organic photoelectric device may be included in a light emitting layer.

The compound for an organic photoelectric device may be used as a phosphorescent or fluorescent host material in a light emitting layer.

The compound for an organic photoelectric device may be used as a fluorescent blue dopant material in a light emitting layer.

The organic photoelectric device may be selected from the group consisting of an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.

In another aspect of the present invention, a display device including the organic photoelectric device described above is provided.

It is possible to provide an organic photoelectric device having excellent life characteristics due to excellent electrochemical and thermal stability and high luminous efficiency even at a low driving voltage.

1 to 5 are cross-sectional views illustrating various embodiments of an organic photoelectric device that may be manufactured using the compound for an organic photoelectric device according to an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C10 alkoxy group, fluoro group, trifluoro It means substituted by C1-C10 trifluoroalkyl groups, such as a romoxy group, or a cyano group.

As used herein, unless otherwise defined, "hetero" means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon.

In the present specification, "combination thereof" means that two or more substituents are bonded to a linking group or two or more substituents are condensed to each other unless otherwise defined.

As used herein, unless otherwise defined, an "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" meaning that it does not contain any alkenes or alkyne groups. The alkyl group may be an "unsaturated alkyl group" meaning that it contains at least one alkene group or alkyne group. "Alkene group" means a functional group consisting of at least two carbon atoms of at least one carbon-carbon double bond, and "alkyne group" means at least two carbon atoms of at least one carbon-carbon triple bond It means a functional group formed. The alkyl group, whether saturated or unsaturated, may be branched, straight chain or cyclic.

The alkyl group may be an alkyl group that is C1 to C20. The alkyl group may be a medium sized alkyl group which is C1 to C10. The alkyl group may be a lower alkyl group which is C1 to C6.

For example, a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:

Typical alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethenyl, propenyl, butenyl, cyclopropyl, cyclobutyl and cyclo It means a functional group which may be substituted with one or more groups individually and independently selected from pentyl group, cyclohexyl group and the like.

"Aromatic group" means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.

An "aryl group" includes monocyclic or fused ring polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.

"Heteroaryl group" means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S and P in the aryl group, and the rest are carbon.

"Spiro structure" means a ring structure having one carbon as a contact point. The spiro structure may also be used as a compound containing a spiro structure or a substituent including a spiro structure.

In one embodiment of the present invention provides a compound for an organic photoelectric device represented by the formula (1).

[Formula 1]

In Formula 1, A ¹ to A ³ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted electronic property It is selected from the group consisting of a C3 to C30 heteroaryl group and -NR'R ", wherein R 'and R" are the same or different from each other, independently hydrogen, substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted Selected from the group consisting of a substituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, at least one of A ¹ to A ³ is a C3 to C30 heteroaryl group having substituted or unsubstituted electronic properties; , At least one of A ¹ to A ³ is substituted or unsubstituted -NR'R ", wherein R 'and R" are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, Substitution or ratio Hwandoen C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 is selected from a heteroaryl group the group consisting of, R ¹ and R ² are the same or different, are independently hydrogen, substituted or unsubstituted C1 to C6 alkyl group, It is selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, X ¹ is N.

In another embodiment of the present invention provides a compound for an organic photoelectric device represented by the following formula (2).

 [Formula 2]

In Formula 2, any one of A ⁴ or A ⁵ is a C3 to C30 heteroaryl group having a substituted or unsubstituted electronic property, the other is -NR'R ", and R 'and R" are the same as each other Different and independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, R ³ and R ⁴ Are the same as or different from each other, and are independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, X ² is one selected from the group consisting of O, P and S.

In Formulas 1 and 2, the carbazole group and the arylamine group are substituents having excellent hole characteristics.

In addition, the C3 to C30 heteroaryl group substituted or unsubstituted in the possible substituents of A1 to A5 is a substituent having excellent electronic properties. Examples thereof include substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted oxatriazole, substituted or unsubstituted Thiatazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzotriazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted Substituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted phthalazine, substituted or unsubstituted naphpyridine , Substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline, substituted or unsubstituted phenazine, and the like.

The structures of Chemical Formulas 1 and 2 are excellent in bipolar properties. In addition, the crystallinity is low because of the high stereoscopic structure.

Preference is given to among the possible heteroatoms of X ¹ and X ² , in particular N and S.

Specific examples of Chemical Formulas 1 and 2 include compounds represented by the following Chemical Formulas 3 to 6.

[Formula 3] [Formula 4]

[Formula 5] [Formula 6]

In another embodiment of the present invention provides a compound for an organic photoelectric device represented by the following formula (7).

[Formula 7]

In Formula 7, R ⁵ and R ⁶ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 Is selected from the group consisting of heteroaryl groups, X ³ is N, A ⁶ to A ⁸ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl Group, a substituted or unsubstituted C3 to C30 heteroaryl group and the following formula S-1 to S-4 is selected from the group consisting of, at least any one of A ⁶ to A ⁸ in the formulas S-1 to S-4 Which one,

Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

R ⁹ to R ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group A ¹¹ and A ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group selected from the group consisting of, X ⁵ is N, wherein X ⁶ is one selected from the group consisting of O, P and S.

At least one of A ⁹ , A ¹⁰ , A ¹¹ or A ¹² may be a substituted or unsubstituted C3 to C30 heteroaryl group.

In another embodiment of the present invention provides a compound for an organic photoelectric device represented by the following formula (8).

 [Formula 8]

In Formula 8, R ⁷ and R ⁸ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 Is selected from the group consisting of heteroaryl groups, X ⁴ is one selected from the group consisting of O, P and S, A ⁹ and A ¹⁰ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group , A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group and the following formula S-1 to S-4 is selected from the group consisting of at least any one of A ⁹ or A ¹⁰ Any one of the formulas S-1 to S-4,

Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

R ⁹ to R ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group A ¹¹ and A ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group selected from the group consisting of, X ⁵ is N, wherein X ⁶ is one selected from the group consisting of O, P and S.

At least one of A ⁹ , A ¹⁰ , A ¹¹ or A ¹² may be a substituted or unsubstituted C3 to C30 heteroaryl group.

In Formulas 7 and 8, the carbazole group and the acridine derivative substituent have excellent hole characteristics.

The substituted or unsubstituted C3 to C30 heteroaryl group among the possible substituents of A ⁶ to A ¹² has excellent electronic properties, and specific examples thereof are the same as the examples of the substituted or unsubstituted C3 to C30 heteroaryl group described above.

Among the possible heteroatoms of X ³ to X ⁶ , in particular, N and S are preferred.

Specific examples of Chemical Formulas 7 and 8 include the following Chemical Formulas 9, 10, 10-H, A-1 to A-39, and the like.

[Formula 9] [Formula 10]

[Formula 10-H] [Formula A-1]

[Formula A-2] [Formula A-3]

[Formula A-4] [Formula A-5]

[Formula A-6] [Formula A-7]

[Formula A-8] [Formula A-9]

[Formula A-10] [Formula A-11]

[Formula A-12] [Formula A-13]

[Formula A-14] [Formula A-15]

[Formula A-16] [Formula A-17]

Formula A-18 Formula A-19

Formula A-20 Formula A-21

Formula A-22 Formula A-23

[Formula A-24] [Formula A-25]

Formula A-26 Formula A-27

Formula A-28 Formula A-29

[Formula A-30] [Formula A-31]

Formula A-32 Formula A-33

Formula A-34 Formula A-35

Formula A-36 Formula A-37

Formula A-38 Formula A-39

Another embodiment of the present invention provides a compound for an organic photoelectric device represented by any one formula selected from the group consisting of the following formulas (11), (12) and (13).

[Formula 11]

[Chemical Formula 12]

[Formula 13]

In Formulas 11, 12 and 13, X ¹ is selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R 'is hydrogen, a substituted or unsubstituted C1 to C6 alkyl group , A substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, any one of X ² or X ³ is -CR ⁴ R ^5- , the other is- O-, -P-, -NR'- and -S-, and R ⁴ and R ⁵ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, substituted Or an unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, wherein R 'is hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heteroaryl group selected from the group consisting of A ¹ to A ³ is the same as or different from each other, and is independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group; R ¹ to R ³ are the same as or different from each other, and are independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from the group.

At least one of the R ', A ¹ to A ³ or R' may be a substituted or unsubstituted C3 to C30 heteroaryl group.

In Formulas 11 to 13, the acridine derivative and carbazole have excellent hole properties.

The substituted or unsubstituted C3 to C30 heteroaryl group among the possible substituents of A ¹ to A ³ has excellent electronic properties, and specific examples thereof are the same as the examples of the substituted or unsubstituted C3 to C30 heteroaryl group described above.

Among the possible heteroatoms of X ¹ to X ³ , in particular, N and S are preferred.

Specific examples of Chemical Formulas 11 to 13 include Chemical Formulas 14 to 20, 16-H1, 16-H2, and B-1 to B-44.

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Formula 18] [Formula 19]

[Formula 20]

[Formula 16-H1] [Formula 16-H2]

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

[Formula B-3] [Formula B-4]

[Formula B-5] [Formula B-6]

[Formula B-7] [Formula B-8]

[Formula B-9] [Formula B-10]

[Formula B-11] [Formula B-12]

[Formula B-13] [Formula B-14]

[Formula B-15] [Formula B-16]

[Formula B-17] [Formula B-18]

Formula B-19 Formula B-20

Formula B-21 Formula B-22

Formula B-23 Formula B-24

[Formula B-25] [Formula B-26]

Formula B-27 Formula B-28

[Formula B-29] [Formula B-30]

Formula B-31 Formula B-32

[Formula B-33] [Formula B-34]

[Formula B-35] [Formula B-36]

Formula B-37 Formula B-38

[Formula B-39] [Formula B-40]

[Formula B-41] [Formula B-42]

Formula B-43 Formula B-44

In another embodiment of the present invention provides a compound for an organic photoelectric device represented by the formula (21).

[Formula 21]

In Chemical Formula 21, z is 0 or 1, R ¹ and R ² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substitution Or an unsubstituted C3 to C30 heteroaryl group, X ¹ is selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R 'is hydrogen, substituted or An unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, C ¹ is the following formula S-5, and C ² is Formula S-6,

[Formula S-5] [Formula S-6]

The two * marks of C ¹ are any two adjacent * marks of the four * marks of Formula S-5, and the two * marks of C ² are any two of the four * marks of Formula S-6. * And R ³ to R ⁶ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 Is selected from the group consisting of heteroaryl groups, and X ² and X ³ are the same as or different from each other, and are independently selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R ' Is selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group.

Z may be 1. In addition, z may be 0. Z may be adjusted according to the desired properties of the compound.

At least one of R ′ or A ¹ to A ⁴ may be a substituted or unsubstituted C3 to C30 heteroaryl group.

In Formula 21, the acridine derivative and carbazole have excellent hole properties.

The substituted or unsubstituted C3 to C30 heteroaryl group among the possible substituents of R ′ and A ¹ to A ⁴ has excellent electronic properties, and specific examples thereof include the examples of the substituted or unsubstituted C3 to C30 heteroaryl group described above. same.

Among the possible heteroatoms of X ¹ to X ³ , in particular, N and S are preferred.

Specific examples of Chemical Formula 21 include the following Chemical Formulas 22 to 31, 22-H, and 23-H.

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

[Formula 26] [Formula 27]

[Formula 28] [Formula 29]

[Formula 30] [Formula 31]

[Formula 22-H] [Formula 23-H]

The compound for an organic photoelectric device including the compound as described above has a glass transition temperature of 120 ° C. or more, and a thermal decomposition temperature of 400 ° C. or more, which is excellent in thermal stability. This makes it possible to implement a high efficiency organic photoelectric device.

The compound for an organic photoelectric device including the compound as described above may serve as light emission, electron injection and / or transport, or hole injection and / or transport, and may also serve as a light emitting host with an appropriate dopant. That is, the compound for an organic photoelectric device may be used as a host material of phosphorescence or fluorescence, a blue dopant material, an electron transport material or a hole transport and / or injection material.

Compound for an organic photoelectric device according to an embodiment of the present invention is used in the organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic photoelectric device, it is possible to lower the driving voltage.

Accordingly, one embodiment of the present invention provides an organic photoelectric device comprising the compound for an organic photoelectric device. In this case, the organic photoelectric device means an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, or an organic memory device. In particular, in the case of an organic solar cell, a compound for an organic photoelectric device according to an exemplary embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency, and in the case of an organic transistor, a gate, a source-drain electrode, and the like are used as electrode materials. Can be used.

Hereinafter, an organic photoelectric device will be described in detail.

Another embodiment of the present invention is an organic photoelectric device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least one of the organic thin film layer is an embodiment of the present invention It provides an organic photoelectric device comprising a compound for an organic photoelectric device according to.

The organic thin film layer which may include the compound for an organic photoelectric device may include a layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a combination thereof. At least one of the layers includes the compound for an organic photoelectric device according to the present invention. In particular, the electron transport layer or the electron injection layer may include a compound for an organic photoelectric device according to an embodiment of the present invention. In addition, when the compound for an organic photoelectric device is included in a light emitting layer, the compound for an organic photoelectric device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material.

1 to 5 are cross-sectional views of an organic photoelectric device including the compound for an organic photoelectric device according to an embodiment of the present invention.

1 to 5, the organic photoelectric device 100, 200, 300, 400, and 500 according to an embodiment of the present invention may be interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.

The anode 120 includes a cathode material, and a material having a large work function is preferable as the anode material so that hole injection can be smoothly injected into the organic thin film layer. Specific examples of the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). And metal oxides such as ZnO and Al, or combinations of metals and oxides such as SnO ₂ and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.), but is not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) may be used as the anode.

The negative electrode 110 includes a negative electrode material, and the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al. , Multilayer structure materials such as LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca, and the like, but are not limited thereto. Preferably, a metal electrode such as aluminum may be used as the cathode.

First, referring to FIG. 1, FIG. 1 illustrates an organic photoelectric device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105. The organic thin film layer 105 may exist only as a light emitting layer 130.

Referring to FIG. 2, FIG. 2 illustrates a two-layered organic photoelectric device 200 in which an emission layer 230 including an electron transport layer and a hole transport layer 140 exist as an organic thin film layer 105, as shown in FIG. 2. Likewise, the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140. In this case, the light emitting layer 130 functions as an electron transporting layer, and the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as ITO.

Referring to FIG. 3, FIG. 3 is a three-layered organic photoelectric device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, wherein the organic thin film layer 105 is formed. The light emitting layer 130 is in an independent form, and has a form in which a film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties or hole transport properties is stacked in separate layers.

Referring to FIG. 4, FIG. 4 is a four-layered organic photoelectric device 400 having an electron injection layer 160, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170 as an organic thin film layer 105. As a result, the hole injection layer 170 may improve adhesion to ITO used as an anode.

Referring to FIG. 5, FIG. 5 shows different functions such as the electron injection layer 160, the electron transport layer 150, the light emitting layer 130, the hole transport layer 140, and the hole injection layer 170 as the organic thin film layer 105. The five-layered organic photoelectric device 500 having five layers is present, and the organic photoelectric device 500 is effective for lowering the voltage by forming the electron injection layer 160 separately.

1 to 5, the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection layer 170 forming the organic thin film layer 105 and their Any one selected from the group consisting of a combination includes the compound for an organic photoelectric device. In this case, the compound for an organic photoelectric device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and among them, a hole blocking layer (not shown) when included in the electron transport layer. It is desirable to provide an organic photoelectric device having a simpler structure since it does not need to be separately formed.

In addition, when the compound for an organic photoelectric device is included in the light emitting layers 130 and 230, the compound for an organic photoelectric device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.

The above-described organic photoelectric device may include a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating after an anode is formed on a substrate; Alternatively, the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.

According to another embodiment of the present invention, a display device including the organic photoelectric device is provided.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains does not change the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100: organic photoelectric device 110: cathode
120: anode 105: organic thin film layer
130: light emitting layer 140: hole transport layer
150: electron transport layer 160: electron injection layer
170: hole injection layer 230: light emitting layer + electron transport layer

Claims (30)

A compound for an organic photoelectric device represented by Formula 1 below:
[Formula 1]

In Chemical Formula 1,
A ¹ to A ³ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a C3 to C30 hetero having a substituted or unsubstituted electronic property An aryl group and -NR'R ", wherein R 'and R" are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 An aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group;
At least one of A ¹ to A ³ is a C3 to C30 heteroaryl group having a substituted or unsubstituted electronic properties,
At least one of A ¹ to A ³ is substituted or unsubstituted —NR′R ″, wherein R ′ and R ″ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, substituted Or an unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group,
R ¹ and R ² are the same as or different from each other, and are independently a group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from
X ¹ is N.
Compound for an organic photoelectric device represented by the formula (2):
(2)

In Chemical Formula 2,
Any one of A ⁴ or A ⁵ is a C3 to C30 heteroaryl group having a substituted or unsubstituted electronic property, the other is -NR'R ", wherein R 'and R" are the same as or different from each other, and independently Hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group,
R ³ and R ⁴ are the same as or different from each other, and are independently a group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from
X ² is one selected from the group consisting of O, S and P.
The method of claim 1,
At least one of A ¹ to A ³ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted oxa Triazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrimidines, substituted or unsubstituted Triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted phthalazine, Substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and substituted or A compound for an organic photoelectric device is selected from the group consisting of a substituted phenazine.
The method of claim 2,
Either A ⁴ or A ⁵ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted oxatriazole , Substituted or unsubstituted thiazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzotriazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted tree Azine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted phthalazine, substituted or Unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and substituted or unsubstituted phen A compound for an organic photoelectric device is selected from the group consisting of Gin.
Compound for an organic photoelectric device represented by any one of the following formulas 3 to 6.
[Formula 3] [Formula 4]

[Formula 5] [Formula 6]

Compound for an organic photoelectric device represented by the formula (7):
[Formula 7]

In Chemical Formula 7,
R ⁵ and R ⁶ are the same as or different from each other, and are independently a group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from
X ³ is N,
A ⁶ to A ⁸ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, and Selected from the group consisting of Formulas S-1 to S-4, at least one of A ⁶ to A ⁸ is any one of Formulas S-1 to S-4,
Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

R ⁹ to R ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from the military,
A ¹¹ and A ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from the military,
X ⁵ is N,
X ⁶ is one selected from the group consisting of O, P, and S.
The method according to claim 6,
At least any one of A ⁶ , A ⁷ , A ⁸ , A ¹¹ or A ¹² is a substituted or unsubstituted C3 to C30 heteroaryl group compound for an organic photoelectric device.
Compound for an organic photoelectric device represented by the formula (8):
[Chemical Formula 8]

In Chemical Formula 8,
R ⁷ and R ⁸ are the same as or different from each other, and are independently a group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from
X ⁴ is one selected from the group consisting of O, P and S,
A ⁹ and A ¹⁰ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, and Selected from the group consisting of Formulas S-1 to S-4, at least one of A ⁹ or A ¹⁰ is any one of Formulas S-1 to S-4,
Formula S-1 Formula S-2

[Formula S-3] [Formula S-4]

R ⁹ to R ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from the military,
A ¹¹ and A ¹² are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from the military,
X ⁵ is N,
X ⁶ is one selected from the group consisting of O, P, and S.
The method of claim 8,
At least any one of A ⁹ , A ¹⁰ , A ¹¹ or A ¹² is a substituted or unsubstituted C3 to C30 heteroaryl group compound for an organic photoelectric device.
The method of claim 7, wherein
At least one of A ⁶ , A ⁷ , A ⁸ , A ¹¹ or A ¹² may be substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxa Diazoles, substituted or unsubstituted oxtriazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridine, substituted or unsubstituted Substituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, Substituted or unsubstituted phthalazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline And substituted or unsubstituted phenazine. The method of claim 9,
At least one of A ⁹ , A ¹⁰ , A ¹¹ or A ¹² may be substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, Substituted or unsubstituted oxtriazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzotriazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyridine Midine, substituted or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted Substituted phthalazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and Compound for an organic photoelectric device is selected from the group consisting of substituted or unsubstituted phenazine.
The compound for an organic photoelectric device represented by the formula selected from the group consisting of the following formulas 9, 10, 10-H and A-1 to A-39.
[Formula 9] [Formula 10]

[Formula 10-H] [Formula A-1]

[Formula A-2] [Formula A-3]

[Formula A-4] [Formula A-5]

[Formula A-6] [Formula A-7]

[Formula A-8] [Formula A-9]

[Formula A-10] [Formula A-11]

[Formula A-12] [Formula A-13]

[Formula A-14] [Formula A-15]

[Formula A-16] [Formula A-17]

Formula A-18 Formula A-19

Formula A-20 Formula A-21

Formula A-22 Formula A-23

[Formula A-24] [Formula A-25]

Formula A-26 Formula A-27

Formula A-28 Formula A-29

[Formula A-30] [Formula A-31]

Formula A-32 Formula A-33

Formula A-34 Formula A-35

Formula A-36 Formula A-37

Formula A-38 Formula A-39

The compound for an organic photoelectric device represented by any one formula selected from the group consisting of the following formula (11), (12) and (13):
(11)

[Formula 12]

[Formula 13]

In Chemical Formulas 11, 12, and 13,
X ¹ is selected from the group consisting of —O—, —P—, —NR′—, and —S—, wherein R ′ is hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 An aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group;
One of X ² or X ³ is -CR ⁴ R ^5- , the other is selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R ⁴ and R ⁵ is The same as or different from each other, and independently selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group, wherein R Is selected from the group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group,
A ¹ to A ³ are the same as or different from each other, and independently a group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from
R ¹ to R ³ are the same as or different from each other, and independently a group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Is selected.
The method of claim 13,
At least any one of A ¹ to A ³ or R 'is a substituted or unsubstituted C3 to C30 heteroaryl group compound for an organic photoelectric device.
The method of claim 13,
At least one of A ¹ to A ³ or R ′ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted Substituted oxtriazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrimidines, substitutions Or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted fruc Tallazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and chi Or unsubstituted phenacyl A compound for an organic photoelectric device is selected from the group consisting of Gin.
The compound for an organic photoelectric device represented by any one formula selected from the group consisting of the following formula 14 to 20, 16-H1, 16-H2 and B-1 to B-44.
[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Formula 18] [Formula 19]

[Chemical Formula 20]

[Formula 16-H1] [Formula 16-H2]

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

[Formula B-3] [Formula B-4]

[Formula B-5] [Formula B-6]

[Formula B-7] [Formula B-8]

[Formula B-9] [Formula B-10]

[Formula B-11] [Formula B-12]

[Formula B-13] [Formula B-14]

[Formula B-15] [Formula B-16]

[Formula B-17] [Formula B-18]

Formula B-19 Formula B-20

Formula B-21 Formula B-22

Formula B-23 Formula B-24

[Formula B-25] [Formula B-26]

Formula B-27 Formula B-28

[Formula B-29] [Formula B-30]

Formula B-31 Formula B-32

[Formula B-33] [Formula B-34]

[Formula B-35] [Formula B-36]

Formula B-37 Formula B-38

[Formula B-39] [Formula B-40]

[Formula B-41] [Formula B-42]

Formula B-43 Formula B-44

A compound for an organic photoelectric device represented by Formula 21:
[Chemical Formula 21]

In Chemical Formula 21,
z is 0 or 1,
R ¹ and R ² are the same as or different from each other, and are independently a group consisting of hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from
X ¹ is selected from the group consisting of —O—, —P—, —NR′—, and —S—, wherein R ′ is hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 An aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group;
C ¹ is a chemical formula S-5, C ² is a chemical formula S-6,
[Formula S-5] [Formula S-6]

Two * marks of C ¹ are any two adjacent * marks of the four * marks of Formula S-5,
Two * marks of C ² are any two adjacent * marks of the four * marks of Formula S-6,
R ³ to R ⁶ are the same as or different from each other, and independently hydrogen, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C3 to C30 heteroaryl group Selected from the military,
X ² and X ³ are the same as or different from each other, and are independently selected from the group consisting of -O-, -P-, -NR'- and -S-, wherein R 'is hydrogen, substituted or unsubstituted C1 To C6 alkyl group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group.
The method of claim 17,
The z is 1 compound for an organic photoelectric device.
The method of claim 17,
Wherein z is 0 compound for an organic photoelectric device.
The method of claim 17,
At least one of the R 'or A ¹ to A ⁴ is a substituted or unsubstituted C3 to C30 heteroaryl group compound for an organic photoelectric device.
The method of claim 17,
At least one of R 'or A ¹ to A ⁴ is substituted or unsubstituted imidazole, substituted or unsubstituted triazole, substituted or unsubstituted tetrazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted Substituted oxtriazoles, substituted or unsubstituted thiazoles, substituted or unsubstituted benzimidazoles, substituted or unsubstituted benzotriazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrimidines, substitutions Or unsubstituted triazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted purine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted fruc Tallazine, substituted or unsubstituted naphpyridine, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazolin, substituted or unsubstituted acridine, substituted or unsubstituted phenanthroline and chi Or unsubstituted phenacyl A compound for an organic photoelectric device is selected from the group consisting of Gin.
The compound for an organic photoelectric device represented by the formula selected from the group consisting of the following formula 22 to 31, 22-H and 23-H.
[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

[Formula 26] [Formula 27]

[Formula 28] [Formula 29]

[Formula 30] [Formula 31]

[Formula 22-H] [Formula 23-H]

In an organic photoelectric device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode,
At least one of the organic thin film layer is an organic photoelectric device comprising the compound for an organic photoelectric device according to claim 1.
The method of claim 23,
The organic thin film layer is selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.
The method of claim 24,
The organic photoelectric device compound is an organic photoelectric device that is included in the hole transport layer or the hole injection layer.
The method of claim 24,
The organic photoelectric device compound is included in the light emitting layer.
The method of claim 24,
The organic photoelectric device compound is used as a phosphorescent or fluorescent host material in the light emitting layer.
The method of claim 24,
The organic photoelectric device compound is used as a fluorescent blue dopant material in the light emitting layer.
The method of claim 23,
The organic photoelectric device is selected from the group consisting of an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum and an organic memory device.
A display device comprising the organic photoelectric device of claim 23.

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