KR101507002B1 - Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode - Google Patents

Abstract

The present invention relates to a compound for an organic optoelectronic device, an organic light emitting device including the same, and a display device including the organic light emitting device. The present invention provides a compound for an organic optoelectronic device represented by the following Chemical Formula 1 and having excellent electrochemical and thermal stability, And an organic light emitting device having a high luminous efficiency even at a low driving voltage can be manufactured.
[Chemical Formula 1]

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device,

The present invention relates to a compound for an organic optoelectronic device capable of providing an organic optoelectronic device excellent in lifetime, efficiency, electrochemical stability and thermal stability, an organic light emitting device including the organic optoelectronic device, and a display device including the organic light emitting device.

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

Organic optoelectronic devices can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electronic device.

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

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting devices, organic solar cells, organic photo conductor drums, and organic transistors, all of which are used for the injection or transport of holes, An injection or transport material, or a luminescent material.

In particular, organic light emitting diodes (OLEDs) have been attracting attention in recent years 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 light emitting device is a device that converts electric energy into light by applying an electric current to an organic light emitting material, and is usually composed of a structure in which a functional organic layer is interposed between an anode and a cathode. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected into the anode and electrons are injected into the organic layer through the cathode, and injected holes and electrons are recombined Energy excitons are formed. At this time, the exciton formed again moves to the ground state, and light having a specific wavelength is generated.

In recent years, it is known that not only fluorescent light emitting materials but also phosphorescent emitting materials can be used as light emitting materials for organic light emitting devices. Such phosphorescence emission is a phenomenon in which electrons are transferred from a ground state to an excited state, The mechanism consists of a non-luminescent transition of a singlet exciton to a triplet exciton through intersystem crossing, followed by a luminescence of the triplet exciton transitioning to the ground state.

As described above, a material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system can be used as a light emitting material in order to increase the light emitting efficiency and stability through the light emitting layer.

In order for the organic luminescent device to fully exhibit the above-described excellent characteristics, a host material and / or a dopant such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material, an electron injecting material, The organic material layer for organic light emitting devices has not been sufficiently developed yet. Therefore, development of new materials has been continuously required. The necessity of developing such a material is the same in other organic optoelectronic devices described above.

In addition, the low-molecular organic light-emitting device has good efficiency and long life performance because it is manufactured in the form of a thin film by a vacuum deposition method. The polymer organic light-emitting device uses an inkjet or spin coating method, There is an advantage that the large area is advantageous.

Low molecular organic light emitting devices and polymer organic light emitting devices are attracting attention as next generation displays because they have advantages such as self-emission, fast response, wide viewing angle, ultra-thin, high image quality, durability and wide driving temperature range. Compared to conventional liquid crystal displays (LCDs), it is self-luminous and has good visibility even when dark or external light enters. It can reduce thickness and weight to 1/3 of that of LCD without backlight.

In addition, the response speed is 1000 times faster than that of LCD, so it is possible to realize perfect video without residual image. Therefore, it is anticipated that it will be seen as an optimal display in accordance with the multimedia age in recent years. Based on these advantages, after the first development in the late 1980s, the efficiency has been rapidly increased to 80 times and the life span of 100 times. And organic light-emitting device panels have been announced, and the size of the organic light-emitting device panel is rapidly increasing.

In order to increase the size, it is necessary to increase the luminous efficiency and the lifetime of the device. At this time, the luminous efficiency of the device should be such that the holes and electrons in the light emitting layer are smoothly coupled. However, since the electron mobility of an organic material is generally slower than the hole mobility, in order to efficiently bond holes and electrons in the light-emitting layer, an efficient electron transport layer is used to increase electron injection and mobility from the cathode, It should be able to block the movement of holes.

Further, in order to improve the lifetime, the material should be prevented from crystallizing due to joule heat generated when the device is driven. Therefore, it is necessary to develop organic compounds having excellent electron injection and mobility and high electrochemical stability.

A hole injecting and transporting role, or an electron injecting and transporting function, and can function as a light emitting host together with an appropriate dopant.

Life, efficiency, driving voltage, electrochemical stability, and thermal stability, and a display device including the organic light emitting device.

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

[Chemical Formula 1]

In Formula 1, X ¹ and X ² are independently -S-, -O-, -S (O) - or -S (O ₂ ) -, L ¹ and L ² are independently a single bond, A substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group, and n1 and n2 are each a substituted or unsubstituted C2 to C10 alkenylene group, independently 0 to a third any integer of, Ar ¹ and Ar ² are independently substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl An aryl group, a substituted or unsubstituted arylamine group or a substituted or unsubstituted heteroarylamine group.

Wherein Ar ¹ and Ar ² are independently a substituted or unsubstituted C2 to C30 heteroaryl group having electron characteristics, a substituted or unsubstituted C6 to C30 aryl group having a hole property, a substituted or unsubstituted C2 To C30 heteroaryl group, a substituted or unsubstituted arylamine group or a substituted or unsubstituted heteroarylamine group.

Ar ¹ and Ar ² may independently be represented by the following formula (2) or (3).

[Chemical Formula 2] < EMI ID =

Wherein R ¹ to R ³ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and * represents the position which binds to L ¹ or L ² in the formula (1).

Ar < ^{1 >} and Ar < ^{2 >} may independently be of the following formula (4) or (5)

[Chemical Formula 4]

Wherein R ¹ to R ³ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and * represents the position which binds to L ¹ or L ² in the formula (1).

Ar < ^{1 >} and Ar < ² >

[Chemical Formula 6]

In Formula 6, Ar ³ and Ar ⁴ are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and * represents a bond to L ¹ or L ² of Formula 1 .

The substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electronic property is a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted carbazole A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted oxadiazolyl group, Substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyridazinyl groups, substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyridazinyl groups, substituted or unsubstituted pyridazinyl groups, substituted or unsubstituted pyridazinyl groups, , A substituted or unsubstituted furyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyl group A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted quinazolinyl group, Lt; / RTI >

The substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electronic characteristic may be a substituent represented by any one of the following formulas (7) to (11).

[Chemical Formula 7]

[Chemical Formula 10]

(11)

Ar ³ and Ar ⁴ are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group , A substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted thiadiazolyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzo-thiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazine group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted phenoxyrthyl group, or a combination thereof.

The compound for an organic optoelectronic device may be represented by any of the following formulas A-1 to A-138.

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

[A-5] [Chemical formula A-6] [Chemical formula A-7] [Chemical formula A-

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

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

[A-18] [Chemical formula A-19] [Chemical formula A-20]

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

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

(A-32) [Formula A-31] [Formula A-32]

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

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

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

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

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

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

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

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

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

[Formula A-72] [Formula A-70] [Formula A-71] [Formula A-72]

[Chemical Formula A-74] [Chemical Formula A-74] [Chemical Formula A-75] [Chemical Formula A-76]

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

[A-82] [Chemical Formula A-83] [Chemical Formula A-84] [Chemical Formula A-

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

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

[Chemical Formula A-93] [Chemical Formula A-94] [Chemical Formula A-95] [Chemical Formula A-96]

[Formula A-97] [Formula A-98] [Formula A-99] [Formula A-100]

[Chemical Formula A-101] [Chemical Formula A-102] [Chemical Formula A-103] [Chemical Formula A-104]

[Formula A-105] [Formula A-106] [Formula A-107] [Formula A-108]

[Formula A-109] [Formula A-110] [Formula A-111] [Formula A-112]

[Formula A-113] [Formula A-114] [Formula A-115] [Formula A-116]

[Chemical Formula A-117] [Chemical Formula A-118] [Chemical Formula A-119] [Chemical Formula A-120]

[Formula A-121] [Formula A-122] [Formula A-123] [Formula A-124]

[Formula A-125] [Formula A-126] [Formula A-127] [Formula A-128]

[Formula A-129] [Formula A-130] [Formula A-131] [Formula A-132]

[Chemical Formula A-133] [Chemical Formula A-134] [Chemical Formula A-135] [Chemical Formula A-136]

[Chemical Formula A-137] [Chemical Formula A-138]

The compound for an organic optoelectronic device may be represented by any one of the following formulas (B-1) to (B-24).

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

[Formula B-5] [Formula B-6] [Formula B-7] [Formula B-8]

[Chemical Formula B-9] Chemical Formula B-10 Chemical Formula B-11 Chemical Formula B-

[Formula B-13] [Formula B-14] [Formula B-15] [Formula B-16]

[Formula B-17] [Formula B-18] [Formula B-19] [Formula B-20]

[Chemical Formula B-21] Chemical Formula B-22 Chemical Formula B-23 Chemical Formula B-

The compound for an organic optoelectronic device may have a triplet excitation energy (T1) of 2.0 eV or more.

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

According to another embodiment of the present invention, there is provided an organic light emitting device comprising a cathode, a cathode, and at least one organic thin film layer interposed between the anode and the cathode, wherein at least one of the organic thin film layers is formed of the organic electroluminescent element Wherein the organic compound is an organic compound.

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

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

The compound for an organic optoelectronic device may be included in the light emitting layer.

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

In another embodiment of the present invention, there is provided a display device including the organic light emitting element described above.

A compound having high hole or electron transporting property, film stability, thermal stability and high triplet excitation energy can be provided.

Such a compound can be used as a hole injecting / transporting material, a host material, or an electron injecting / transporting material of a light emitting layer. The organic optoelectronic device using the organic electroluminescent device has excellent electrochemical and thermal stability, and has excellent lifetime characteristics and high luminous efficiency even at low driving voltage.

1 to 5 are cross-sectional views illustrating various embodiments of an organic light emitting device that can be manufactured using a compound for an organic optoelectronic 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, at least one of the substituents or at least one hydrogen in the compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, C1 to C10 alkyl groups such as a C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, A trifluoroalkyl group or a cyano group.

A substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C10 alkylsulfinyl group, A C1 to C10 trifluoroalkyl group such as a C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group or a trifluoromethyl group, or a cyano group may be fused together to form a ring .

Means one to three heteroatoms selected from the group consisting of N, O, S and P in one functional group, and the remainder is carbon, unless otherwise defined.

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

As used herein, the term "alkyl group" means an aliphatic hydrocarbon group, unless otherwise defined. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

"Alkynylene group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynylene group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding. The alkyl group, whether saturated or unsaturated, can be branched, straight chain or cyclic.

The alkyl group may be an alkyl group of C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.

For example, the C1 to C4 alkyl groups may have 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, ethenyl group, Butyl group, cyclopentyl group, cyclohexyl group, and the like.

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

An "aryl group" includes a monocyclic or fused ring polycyclic (i. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

"Heteroaryl group" means that the aryl group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

In the present specification, a carbazole-based derivative means a structure in which a nitrogen atom of a substituted or unsubstituted carbazolyl group is replaced by a hetero atom other than nitrogen. Specific examples thereof include dibenzofuran (dibenzofuranyl), dibenzothiophene (dibenzothiophenyl), and the like.

In the present specification, the hole property means a property of facilitating the injection into the light emitting layer and the movement in the light emitting layer of the hole formed in the anode due to conduction characteristics along the HOMO level.

Further, the electron characteristic means a property of facilitating the injection of electrons formed in the anode into the luminescent layer and the movement in the luminescent layer due to conduction characteristics along the LUMO level.

The compound for an organic optoelectronic device according to an embodiment of the present invention may include a substituent having an electron characteristic and / or a substituent having a hole characteristic in a core in which two carbazole derivatives are fused.

The HOMO and LUMO levels of the whole compound can be appropriately adjusted as needed by including a substituent having a hole property and / or a substituent having an electron characteristic to the core, thereby preparing a compound for an organic optoelectronic device having various energy levels have.

The core structure may be used as a light emitting material, a hole injecting material, or a hole transporting material of an organic optoelectronic device. And may be particularly suitable for a light emitting material.

In addition, the compound for an organic optoelectronic device may be a compound having various energy bandgaps by introducing various substituents to the substituents substituted in the core portion and the core portion.

By using a compound having an appropriate energy level according to the substituent of the compound in an organic optoelectronic device, the hole transporting ability or the electron transporting ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent electrochemical and thermal stability. The lifetime characteristics can be improved when the device is driven.

According to an embodiment of the present invention, the compound for organic optoelectronic devices may be a compound for organic optoelectronic devices represented by the following formula (1).

[Chemical Formula 1]

In Formula 1, X ¹ and X ² are independently -S-, -O-, -S (O) - or -S (O ₂ ) -, L ¹ and L ² are independently a single bond, A substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group, and n1 and n2 are each a substituted or unsubstituted C2 to C10 alkenylene group, independently 0 to a third any integer of, Ar ¹ and Ar ² are independently substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl An aryl group, a substituted or unsubstituted arylamine group or a substituted or unsubstituted heteroarylamine group.

Wherein Ar ¹ and Ar ² are independently a substituted or unsubstituted C2 to C30 heteroaryl group having electron characteristics, a substituted or unsubstituted C6 to C30 aryl group having a hole property, a substituted or unsubstituted C2 To C30 heteroaryl group, a substituted or unsubstituted arylamine group or a substituted or unsubstituted heteroarylamine group.

Due to such substituents, the compound for organic optoelectronic devices may exhibit luminescence, hole or electron characteristics; Membrane stability; Thermal stability and high triplet excitation energy (T1).

Further, by controlling the substituent, the structure of the compound can be bulk produced, thereby lowering the crystallinity. If the crystallinity of the compound is lowered, the lifetime of the device may be prolonged.

Ar ¹ and Ar ² may independently be represented by the following formula (2) or (3).

[Chemical Formula 2] < EMI ID =

Wherein R ¹ to R ³ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and * represents a position bonded to the L ¹ in the general formula (1).

Ar < ^{1 >} and Ar < ^{2 >} may independently be represented by the following formula (4) or (5) In this case, the hole mobility of the compound can be increased.

[Chemical Formula 4]

Wherein R ¹ to R ³ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and * represents a position bonded to the L ¹ in the general formula (1).

Ar < ^{1 >} and Ar < ² >

[Chemical Formula 6]

In the formula (6), and Ar ³ and Ar ⁴ are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group unsubstituted, * is a position to bind to L ¹ in the general formula (1) .

The conjugation length of the entire compound can be determined by selectively controlling L ¹ and L ² , and the effect of increasing the Tg and controlling the energy level can be obtained.

Specific examples of L ¹ and L ² include a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted A substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a thiophene group, a furan group and the like.

More specifically, the substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic is a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiaryl group, A substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted quinolinyl group, Substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, substituted or unsubstituted quinazolinyl groups, A substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, or a combination thereof, but is not limited thereto.

More specifically, the substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electronic characteristic may be a substituent represented by any one of the following formulas (7) to (11).

[Chemical Formula 7]

[Chemical Formula 10]

(11)

More specifically, the substituted or unsubstituted C6 to C30 aryl group having the hole property is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group , A substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrazolyl group, An unsubstituted perylenyl group, or a combination thereof.

More specifically, the substituted or unsubstituted C2 to C30 heteroaryl group having a hole property is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, And a substituted indolecarbazolyl group.

Ar ¹ and Ar ² may independently be the above-described formula (6), wherein Ar ³ and Ar ⁴ independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, An unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furan A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, Or a substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazine group, a substituted or unsubstituted phenothiazyl group, Group, may be substituted or unsubstituted phenoxazine group, or a combination thereof.

The compound for an organic optoelectronic device may be represented by any one of the following formulas A-1 to A-138, but is not limited thereto.

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

[A-5] [Chemical formula A-6] [Chemical formula A-7] [Chemical formula A-

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

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

[A-18] [Chemical formula A-19] [Chemical formula A-20]

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

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

(A-32) [Formula A-31] [Formula A-32]

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

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

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

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

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

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

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

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

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

[Formula A-72] [Formula A-70] [Formula A-71] [Formula A-72]

[Chemical Formula A-74] [Chemical Formula A-74] [Chemical Formula A-75] [Chemical Formula A-76]

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

[A-82] [Chemical Formula A-83] [Chemical Formula A-84] [Chemical Formula A-

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

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

[Chemical Formula A-93] [Chemical Formula A-94] [Chemical Formula A-95] [Chemical Formula A-96]

[Formula A-97] [Formula A-98] [Formula A-99] [Formula A-100]

[Chemical Formula A-101] [Chemical Formula A-102] [Chemical Formula A-103] [Chemical Formula A-104]

[Formula A-105] [Formula A-106] [Formula A-107] [Formula A-108]

[Formula A-109] [Formula A-110] [Formula A-111] [Formula A-112]

[Formula A-113] [Formula A-114] [Formula A-115] [Formula A-116]

[Chemical Formula A-117] [Chemical Formula A-118] [Chemical Formula A-119] [Chemical Formula A-120]

[Formula A-121] [Formula A-122] [Formula A-123] [Formula A-124]

[Formula A-125] [Formula A-126] [Formula A-127] [Formula A-128]

[Formula A-129] [Formula A-130] [Formula A-131] [Formula A-132]

[Chemical Formula A-133] [Chemical Formula A-134] [Chemical Formula A-135] [Chemical Formula A-136]

[Chemical Formula A-137] [Chemical Formula A-138]

The compound for an organic optoelectronic device may be represented by any one of the following formulas (B-1) to (B-24), but is not limited thereto.

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

[Formula B-5] [Formula B-6] [Formula B-7] [Formula B-8]

[Chemical Formula B-9] Chemical Formula B-10 Chemical Formula B-11 Chemical Formula B-

[Formula B-13] [Formula B-14] [Formula B-15] [Formula B-16]

[Formula B-17] [Formula B-18] [Formula B-19] [Formula B-20]

[Chemical Formula B-21] Chemical Formula B-22 Chemical Formula B-23 Chemical Formula B-

In the case where the compound according to one embodiment of the present invention requires both the electronic property and the hole property, it is effective to improve the lifetime of the organic light emitting device and reduce the driving voltage by introducing the functional group having the electron characteristic.

The compound for an organic optoelectronic device according to one embodiment of the present invention has a maximum emission wavelength in a range of about 320 to 500 nm and a triplet excitation energy (T1) in a range of 2.0 eV or more, more specifically 2.0 to 4.0 eV The charge of a host having a high triplet excitation energy can be transferred to the dopant to increase the luminous efficiency of the dopant and freely adjust the HOMO and LUMO energy levels of the material to lower the driving voltage It can be very useful as a host material or a charge transport material.

In addition, since the compound for organic optoelectronic devices has a photoactive and electrical activity, it can be used as a nonlinear optical material, an electrode material, a coloring material, an optical switch, a sensor, a module, a waveguide, an organic transistor, it can be very usefully applied to materials such as a membrane.

The compound for organic optoelectronic devices including the above compound has a glass transition temperature of 90 ° C or higher and a thermal decomposition temperature of 400 ° C or higher, which is excellent in thermal stability. As a result, it is possible to realize a highly efficient organic photoelectric device.

The compound for organic optoelectronic devices including the above-described compounds can play a role of luminescent host together with a suitable dopant, and can play a role of luminescence, electron injection and / or transport. That is, the compound for an organic optoelectronic device can be used as a phosphorescent or fluorescent host material, a blue luminescent dopant material, or an electron transporting material.

The compound for an organic optoelectronic device according to an embodiment of the present invention can be used in an organic thin film layer to improve lifetime characteristics, efficiency characteristics, electrochemical stability and thermal stability of an organic optoelectronic device, and lower a driving voltage.

Accordingly, one embodiment of the present invention provides an organic optoelectronic device including the compound for an organic optoelectronic device. Here, the organic photoelectrode refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoconductor drum, an organic memory device, or the like. In particular, in the case of an organic solar cell, the compound for an organic optoelectronic device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency. In the case of an organic transistor, an electrode material in a gate, a source- Can be used.

Hereinafter, the organic light emitting device will be described in detail.

Another embodiment of the present invention is an organic light emitting device comprising a cathode, a cathode, and at least one or more organic thin film layers interposed between the anode and the cathode, wherein at least one of the organic thin film layers is an organic thin film And a compound for an organic optoelectronic device according to the present invention.

The organic thin film layer that can include the compound for an organic optoelectronic device may include a layer selected from the group consisting of a light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, At least one of the layers includes the compound for organic optoelectronic devices according to the present invention. In particular, the hole transport layer or the hole injection layer may include the compound for organic optoelectronic devices according to an embodiment of the present invention. When the compound for an organic optoelectronic device is contained in the light emitting layer, the compound for the organic optoelectronic 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 sectional views of an organic light emitting device including a compound for an organic optoelectronic device according to an embodiment of the present invention.

1 to 5, organic light emitting devices 100, 200, 300, 400, and 500 according to an embodiment of the present invention include a cathode 120, a cathode 110, And a structure including at least one organic thin film layer (105).

The anode 120 includes a cathode material. As the anode material, a material having a large work function is preferably used to facilitate injection of holes 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 zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide ), And combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene- 2-dioxythiophene] (PEDT), conductive polymers such as polypyrrole and polyaniline, but are not limited thereto. Preferably, a transparent electrode including ITO (indium tin oxide) may be used as the anode.

The cathode 110 includes a cathode material, and the anode 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 and the like, , LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca. However, the present invention is not limited thereto. Preferably, a metal electrode such as aluminum or the like may be used for the negative electrode.

1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 is present as an organic thin film layer 105. The organic thin film layer 105 may exist only in the light emitting layer 130. FIG.

2 illustrates a two-layer organic light emitting device 200 having a light emitting layer 230 including an electron transporting layer and a hole transporting layer 140 as an organic thin film layer 105. As shown in FIG. 2, Similarly, the organic thin film layer 105 may be of a two-layer type including a light emitting layer 230 and a hole transporting 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 the bonding property with a transparent electrode such as ITO and the hole transporting property.

3 is a three-layer organic light emitting device 300 in which an electron transport layer 150, a light emitting layer 130 and a hole transport layer 140 are present as an organic thin film layer 105. The organic thin film layer 105, The emissive layer 130 is in the form of an independent layer and has a form in which a film having excellent electron transportability and hole transportability (the electron transport layer 150 and the hole transport layer 140) is stacked as a separate layer.

4, a four-layer organic light emitting 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 organic thin film layers 105, And the hole injection layer 170 can improve the bonding property with ITO used as the anode.

5, the organic thin film layer 105 has different functions such as an electron injection layer 160, an electron transport layer 150, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170 Layer organic light emitting device 500. The organic light emitting device 500 is 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, the hole injection layer 170, and the organic thin film layer 105, And combinations thereof include compounds for the organic optoelectronic devices. At this time, the compound for an organic optoelectronic device can be used for the electron transport layer 150 or the electron transport layer 150 including the electron injection layer 160, and when included in the electron transport layer, a hole blocking layer (not shown) It is not necessary to form them separately, and an organic light emitting device having a more simplified structure can be provided.

When the compound for an organic optoelectronic device is contained in the light emitting layers 130 and 230, the compound for the organic optoelectronic device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.

The organic light emitting device described above may be formed by a dry film forming method such as evaporation, sputtering, plasma plating, and ion plating after an anode is formed on a substrate; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode on the organic thin film layer.

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

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

(Preparation of compound for organic optoelectronic device)

Example  1: Synthesis of Compound A-9

The compound of the above formula A-9 shown as a more specific example of the compound for an organic optoelectronic device according to an embodiment of the present invention was synthesized through the route shown in the following reaction scheme 1.

[Reaction Scheme 1]

Step 1: Synthesis of intermediate product (A)

A mixture of 10.0 g (65.8 mmol) of 2-methoxyphenylboronic acid, 8.52 g (31.34 mmol) of 1,4-dibromo-2,5-difluorobenzene and 12.99 g (94.01 mmol) of potassium carbonate, 0.72 g (0.63 mmol) of triphenylphosphine palladium (0) was suspended in 130 ml of toluene and 65 ml of distilled water, followed by stirring under reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, and the mixture was separated by silica gel. The mixture was distilled under reduced pressure and the residue was purified by silica column chromatography to obtain 6.65 g of an intermediate product (A) (yield: 65%).

Step 2: Synthesis of intermediate product (B)

The intermediate product (A) 6.65 g (20.37 mmol ) and suspended in dichloro methane and 130 mL at _{-78 ℃ 1M BBr 3 CH 2 Cl} 2 47.84 mL (47.84 mmol) Add slowly. The mixture was stirred at -78 ° C for 30 minutes and then at room temperature for 24 hours. After completion of the reaction, the reaction mixture was quenched with aqueous NaHCO ₃ solution and extracted with dichloromethane. The organic layer was separated by silica gel and separated by silica gel to obtain 4.92 g (yield: 81%) of intermediate product (B).

Step 3: Synthesis of intermediate product (C)

4.92 g (16.5 mmol) of the intermediate product (B), 5.02 g (36.3 mmol) of potassium carbonate and 70 mL of NMP. And the mixture was refluxed for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is separated into silica gel. The residue was separated by silica gel to obtain 3.54 g (yield: 83%) of the intermediate product (C).

Step 4: Synthesis of intermediate product (D)

A suspension of 3.54 g (13.8 mmol) of the intermediate product (C) and 30 mL of THF and slowly adding 20.7 mL (41.4 mmol) of 2.0 M LDA (lithium diisopropylamide) THF at 0 ° C is added. After stirring at 0 ° C for 30 minutes, quickly add 21.03 g (82.8 mmol) of I ₂ . Stir at room temperature for 1 hour. After completion of the reaction, the reaction mixture was quenched with an aqueous solution of Na ₂ SO ₃ , recrystallized from dichloromethane and n-hexane, and then the organic solvent was removed to obtain 6.19 g (yield: 88%) of intermediate product (D).

Step 5: Synthesis of compound of formula A-9

0.36 g (0.39 mmmol) of Pd ₂ (dba) ₃ was dissolved in toluene (10 ml) and the mixture was stirred at room temperature for 10 minutes. A mixture of 10.0 g (19.6 mmol) of the intermediate compound (D), 7.30 g (43.1 mmol) of diphenylamine, 100 ml, and 0.29 ml (1.18 mmol) of P (t-Bu) ₃ was added thereto, followed by stirring under reflux for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is separated into silica gel. The organic solution was removed and the product was separated by silica gel with hexane: dichloromethane = 7: 3 (v / v), and the product solid was recrystallized from dichloromethane and acetone to give 10.1 g of the compound of formula A-9 (yield: 87%) .

Example  2: Synthesis of Compound A-14

The intermediate compound (D) 10.0 g (19.6 mmol ) and biphenyl-dimethyl-fluorene-amine 15.58 g (43.1 mmol), NaO (t-Bu) 4.52 g (47.04 mmol), Pd 2 (dba) 3 0.36 g (0.39 mmmol ) Was suspended in 100 ml of toluene, and 0.29 mL (1.18 mmol) of P (t-Bu) ₃ was added thereto, followed by reflux stirring for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is separated into silica gel. The organic solution was removed and the product was separated into silica gel with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and acetone to obtain 13.5 g (yield: 70%) of the compound of formula A-9 .

Example  3: Synthesis of Compound A-16

0.36 g (0.39 mmmol) of Pd ₂ (dba) ₃ was dissolved in toluene 100 (100 ml), and the mixture was stirred at room temperature for ₃ hours. Then, 10.0 g (19.6 mmol) of the intermediate compound (D), 7.21 g (43.1 mmol) of carbazole, 4.52 g (47.04 mmol) ml, 0.29 mL (1.18 mmol) of P (t-Bu) ₃ was added thereto, and the mixture was stirred under reflux for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is separated into silica gel. The organic solution was removed and the product was separated into silica gel with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and acetone to give 10.2 g of the compound of formula A-16 (yield: 88% .

Example  4: Synthesis of Compound A-103

15.36 g (43.1 mmol) of 1,3-diphenylbenzene-5-boronic ester, 6.21 g (47.04 mmol) of K ₂ CO ₃ and Pd (PPh ₃ ) ₄ 0.45 g (0.39 mmmol) of toluene was added to 100 ml of toluene, and the mixture was refluxed for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is separated into silica gel. The organic solution was removed and the product was separated into silica gel with hexane: dichloromethane = 7: 3 (v / v) to obtain 11.4 g (yield: 81%) of a compound of formula A-103 as a solid which was recrystallized from dichloromethane and acetone .

Example  5: Synthesis of Compound A-110

The intermediate compound (D) 10.0 g (19.6 mmol ) and 4-benzothiophene boronic acid 9.83 g (43.1 mmol), K 2 CO 3 6.21 g (47.04 mmol), Pd (PPh 3) 4 0.45 g (0.39 mmmol ) Were added to 100 ml of toluene, and the mixture was stirred under reflux for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is separated into silica gel. The organic solution was removed and the product was separated by silica gel with hexane: dichloromethane = 7: 3 (v / v), and the product solid was recrystallized from dichloromethane and acetone to obtain 10.8 g (yield: 88%) of the compound of formula A-103 .

Example  6: Synthesis of Compound A-137

A mixture of 6.19 g (12.14 mmol) of Intermediate Compound (D), 7.67 g (26.71 mmol) of N-phenylcarbazole-3-boronic acid and 6.71 g (48.56 mmol) of potassium carbonate, tetrakis- (triphenylphosphine) palladium 0) 0.28 g (0.24 mmmol) was suspended in toluene (100 ml) and distilled water (50 ml), followed by reflux stirring for 12 hours. After completion of the reaction, the reaction solution was extracted with dichloromethane, and the residue was separated by silica gel. The residue was distilled under reduced pressure and the residue was purified by silica column chromatography to obtain 8.1 g (yield: 90%) of the compound of formula A-137.

Example  7: Synthesis of Compound B-3

The intermediate compound (D) 10.0 g (19.6 mmol ) and 4-phenyl-2-pyridyl-boronic acid 8.58 g (43.1 mmol), K 2 CO 3 6.21 g (47.04 mmol), Pd (PPh 3) 4 0.45 g ( 0.39 mmmol) were added to 100 ml of toluene, and the mixture was stirred under reflux for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is separated into silica gel. The organic solution was removed and the product was separated into a silica gel column with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and acetone to obtain 9.8 g (yield: 89% Respectively.

(Production of organic light emitting device)

Example  8: Of organic optoelectronic devices  Produce

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine. The prepared ITO transparent electrode was used as an anode to form a 4,4'-bis [N- [4- {N, N-bis (3-methylphenyl) amino} -phenyl] -N-phenylamino] biphenyl ) Was vacuum-deposited to form a hole injection layer having a thickness of 600 Å. Subsequently, a 300 Å thick hole transport layer was formed by vacuum deposition using the compound prepared in Example 1. (2-naphthyl) anthracene (ADN) was used as a host on top of the hole transport layer, and 3, 5 wt% of 2,5,8,11-tetra (tert- Doped and vacuum evaporated to form a 250 Å thick light emitting layer.

Thereafter, Alq3 was vacuum deposited on the light emitting layer to form an electron transporting layer having a thickness of 250 ANGSTROM. LiF 10 Å and Al 1000 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

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

The structure of Al (1000 Å) / LiF (10 Å) / Alq 3 (250 Å) / EML [ADN: TBPe = 97: 3] (250 Å) / HTL (300 Å) / DNTPD (600 Å) / ITO (1500 Å)

Example  9

An organic light emitting device was prepared in the same manner as in Example 8, except that Example 2 was used instead of Example 1.

Example  10

An organic light emitting device was prepared in the same manner as in Example 8, except that Example 3 was used instead of Example 1.

Example  11

An organic light emitting device was prepared in the same manner as in Example 8, except that Example 4 was used instead of Example 1.

Example  12

An organic light emitting device was prepared in the same manner as in Example 8, except that Example 5 was used instead of Example 1.

Example  13

An organic light emitting device was prepared in the same manner as in Example 8, except that Example 6 was used instead of Example 1.

Example  14

An organic light emitting device was prepared in the same manner as in Example 8, except that Example 7 was used instead of Example 1.

Comparative Example  One

N'-bis- (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine instead of Example 1 Except for using NPB, N, N'-Bis- (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'- Thereby preparing an organic light emitting device.

The structures of DNTPD, ADN and TBPe used in the above organic light emitting device are as follows.

[DNTPD] [ADN] [TBPe]

(Performance Measurement of Organic Light Emitting Device)

For each of the organic light emitting devices fabricated in Examples 8 to 14, the change in current density, the luminance change, and the luminous efficiency were measured according to the voltage. Specific measurement methods are as follows, and the results are shown in Table 1 below

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

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

(2) Measurement of luminance change according to voltage change

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

(3) Measurement of luminous efficiency

Current efficiency (cd / A) and current efficiency (㏐ / W) of the same current density (10 mA / cm ² ) were calculated using the luminance, current density and voltage measured from the above (1) and (2).

device Compound used in hole transport layer Voltage (V) Color (EL color) Efficiency (cd / A) Efficiency (㏐ / W) Example 8 A-9 5.9 Blue 5.5 2.9 Example 9 A-14 5.7 Blue 5.7 3.1 Example 10 A-16 5.8 Blue 5.8 3.1 Example 11 A-103 6.0 Blue 6.0 3.1 Example 12 A-110 6.5 Blue 5.2 2.5 Example 13 A-137 5.5 Blue 6.0 3.4 Example 14 B-3 5.9 Blue 5.0 2.7 Comparative Example 1 NPB 7.1 Blue 4.9 2.2

The devices of Examples 8 to 14 according to an embodiment of the present invention have lower driving voltage and higher efficiency than the device of Comparative Example 1. [

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

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

Claims (17)

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

In Formula 1,
X ¹ and X ² are independently -O-,
L ¹ and L ² are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,
n1 and n2 are independently an integer of 0 to 3,
Ar ¹ and Ar ² are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group .
The method according to claim 1,
Wherein Ar ¹ and Ar ² are independently a substituted or unsubstituted C2 to C30 heteroaryl group having electron characteristics, a substituted or unsubstituted C6 to C30 aryl group having a hole property, a substituted or unsubstituted C2 To C30 heteroaryl group, a substituted or unsubstituted arylamine group or a substituted or unsubstituted heteroarylamine group,
The substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electronic property is a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted carbazole A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted oxadiazolyl group, Substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyridazinyl groups, substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyridazinyl groups, substituted or unsubstituted pyridazinyl groups, substituted or unsubstituted pyridazinyl groups, , A substituted or unsubstituted furyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted naphthyl group A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, or a substituted or unsubstituted quinazolinyl group Lt; / RTI >
The substituted or unsubstituted C6 to C30 aryl group having the hole property may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, A perylenyl group, or a combination thereof,
The substituted or unsubstituted C2 to C30 heteroaryl group having the hole property may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, Wherein R < 1 >
3. The method of claim 2,
Wherein Ar ¹ and Ar ² are independently of one to the formula 2 or 3. A compound for an organic optoelectronic device:
[Chemical Formula 2] < EMI ID =

In the above Formulas 2 and 3,
R ¹ to R ³ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
* Represents the position which binds to L ¹ or L ² in the formula (1).
3. The method of claim 2,
Wherein Ar < ^{1 >} and Ar < ^{2 >} are independently of the formula (4) or (5)
[Chemical Formula 4]

In the above formulas (4) and (5)
R ¹ to R ³ are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
* Represents the position which binds to L ¹ or L ² in the formula (1).
3. The method of claim 2,
Wherein Ar < ^{1 >} and Ar < ^{2 >} are independently of the formula (6)
[Chemical Formula 6]

In Formula 6,
Ar ³ and Ar ⁴ are independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
* Represents the position which binds to L ¹ or L ² in the formula (1).
delete 3. The method of claim 2,
Wherein said substituted or unsubstituted C2 to C30 heteroaryl group having said electron characteristic is a substituent represented by any one of the following formulas (7) to (11).
[Chemical Formula 7]

[Chemical Formula 10]

(11)

6. The method of claim 5,
Ar ³ and Ar ⁴ are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group , A substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted thiadiazolyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzo-thiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazine group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted phenoxyril group, or a combination thereof.
The method according to claim 1,
Wherein the compound for an organic optoelectronic device is represented by any one of the following formulas A-1 to A-48, A-97 to A-116, and A-137.
[Formula A-1] [Formula A-2] [Formula A-3] [Formula A-4]

[A-5] [Chemical formula A-6] [Chemical formula A-7] [Chemical formula A-

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

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

[A-18] [Chemical formula A-19] [Chemical formula A-20]

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

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

(A-32) [Formula A-31] [Formula A-32]

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

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

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

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

[Formula A-97] [Formula A-98] [Formula A-99] [Formula A-100]

[Chemical Formula A-101] [Chemical Formula A-102] [Chemical Formula A-103] [Chemical Formula A-104]

[Formula A-105] [Formula A-106] [Formula A-107] [Formula A-108]

[Formula A-109] [Formula A-110] [Formula A-111] [Formula A-112]

[Formula A-113] [Formula A-114] [Formula A-115] [Formula A-116]

[A-137]

The method according to claim 1,
Wherein the compound for an organic optoelectronic device is represented by any one of the following formulas (B-1) to (B-12).
[Formula B-1] [Formula B-2] [Formula B-3] [Formula B-4]

[Formula B-5] [Formula B-6] [Formula B-7] [Formula B-8]

[Chemical Formula B-9] Chemical Formula B-10 Chemical Formula B-11 Chemical Formula B-

The method according to claim 1,
Wherein the compound for an organic optoelectronic device has a triplet excitation energy (T1) of 2.0 eV or more.
The method according to claim 1,
Wherein the organic optoelectronic device is selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoreceptor drum, and an organic memory device.
An organic light emitting device comprising an anode, a cathode, and at least one organic thin film layer interposed between the anode and the cathode,
Wherein at least one of the organic thin film layers comprises the compound for an organic optoelectronic device according to any one of claims 1 to 5 and 7 to 12.
14. The method of claim 13,
Wherein the organic thin film layer is selected from the group consisting of a light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and combinations thereof.
15. The method of claim 14,
Wherein the compound for an organic optoelectronic device is contained in a light emitting layer.
16. The method of claim 15,
Wherein the compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in a light emitting layer.
14. A display device comprising the organic light emitting element according to claim 13.

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