KR101789254B1 - 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 from the cathode. The injected holes and electrons meet and recombine 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, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R" -, X ¹ to X ⁸ are independently of each other, -CR'- or -N-, X ¹ to X ⁸ independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , Ar ² , R 'and R "are, independently of each other, hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted Or a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted Or a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, C1 to C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, any one of X ¹ to X ⁴ is -CR ' -, wherein R 'means a bond with an adjacent substituent, and any one of X ⁵ to X ⁸ is -CR'-, wherein R' means a bond with an adjacent substituent, A few of Ar ¹ and Ar ² Is a substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic, L ¹ and L ² are, independently of each other, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 A substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, n1 and n2 are each independently any one of an integer of 0 to 3 M1 and m2 are each independently any one of 0 to 3, and m1 and m2 are not 0 at the same time.

Y ¹ and Y ² may be independently of each other -O-, -S-, -S (O ₂ ) -, or -NR'-.

Y ¹ and Y ² may be different from each other.

The compound for an organic optoelectronic device may be represented by the following formula (2).

(2)

In Formula 2, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R"'-, X ¹ to X ⁸ independently of one another are -CR'- or -N-, X ¹ to X ⁸ are independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , R' And R " are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine groups, nitro, carboxyl, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group , A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, Substituted or unsubstituted C2 to C20 acyloxy groups, substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, A C1 to C20 heterocyclothiol group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,

Wherein one of X ¹ to X ⁴ is -CR'-, wherein R 'means a bond with an adjacent substituent, Ar ¹ is a substituted or unsubstituted C2 to C30 heteroaryl Group, and m1 is 1 or 2.

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

(3)

In Formula 3, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R"'-, X ¹ to X ⁸ independently of one another are -CR'- or -N-, X ¹ to X ⁸ are independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , R' And R " are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine groups, nitro, carboxyl, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group , A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, Substituted or unsubstituted C2 to C20 acyloxy groups, substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C1 to C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, any one of X ¹ to X ⁴ are ring -CR'- , Wherein R 'represents a bond to an adjacent substituent, and Ar ¹ represents a substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic.

The compound for an organic optoelectronic device may be represented by the following formula (4).

[Chemical Formula 4]

In Formula 4, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R"'-, X ¹ to X ⁸ independently of one another are -CR'- or -N-, X ¹ to X ⁸ are independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , R' And R " are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine groups, nitro, carboxyl, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group , A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, Substituted or unsubstituted C2 to C20 acyloxy groups, substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C1 to C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, any one of X ¹ to X ⁴ are ring -CR'- , Wherein R 'represents a bond to an adjacent substituent, and Ar ¹ represents a substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic.

X ¹ to X ⁸ may all be -CR'-.

At least one of X ¹ to X ⁸ may be N.

Y ² may be -NR'-, and Y ¹ may be -NR'- or -S-.

Y ¹ and Y ² may all be -NR'-.

Y ² is -NR'-, and Y ¹ may be -CR'R "- or -SiR'R" - ".

Y ² may be -CR'R "-, and Y ¹ may be -SiR'R"'-.

The substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electron characteristic is a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, A substituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, or a combination thereof.

The substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electronic characteristics may be any one of the following formulas (X-1) to (X-15).

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

[Formula X-3] [Formula X-4]

[Formula X-5] [Formula X-6]

[Formula X-7] [Formula X-8] [Formula X-9] Formula [X-10]

[Formula X-11] [Formula X-12] Formula [X-13]

[Formula X-14] [Formula X-15]

The compound for an organic optoelectronic device may be represented by any of the following formulas A-1 to A-145.

[A-1] [A-2] [A-3]

[A-4] [A-5] [A-6]

[A-7] [A-8] [A-9]

[A-10] [A-11] [A-12]

[A-13] [A-14]

[A-15] [A-16]

[A-17] [A-18]

[A-19] [A-20]

[A-21] [A-22]

[A-23] [A-24] [A-25]

[A-26] [A-27] [A-28]

[A-29] [A-30] [A-31]

[A-32] [A-33] [A-34]

[A-35] [A-36]

[A-37] [A-38]

[A-39] [A-40] [A-41]

[A-41] [A-42] [A-43]

[A-44] [A-45] [A-46]

[A-47] [A-48] [A-49]

[A-50] [A-51] [A-52]

[A-53] [A-54] [A-55]

[A-56] [A-57] [A-58]

[A-59] [A-60] [A-61]

[A-62] [A-63] [A-64]

[A-65] [A-66] [A-67]

[A-68] [A-69]

[A-70] [A-71]

[A-72] [A-73]

[A-74] [A-75] [A-76]

[A-77] [A-78] [A-79]

[A-80] [A-81]

[A-82] [A-83]

[A-84] [A-85]

[A-86] [A-87]

[A-88] [A-89]

[A-90] [A-91] [A-92] [A-93]

[A-94] [A-95] [A-96]

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

[A-101] [A-102] [A-103]

[A-104]

[A-105] [A-106] [A-107]

[A-108] [A-109] [A-110]

[A-111] [A-112] [A-113] [A-114]

[A-115] [A-116]

[A-117] [A-118] [A-119]

[A-120] [A-121] [A-122]

[A-123] [A-124]

[A-125] [A-126] [A-127]

[A-128] [A-129] [A-130]

[A-131] [A-132] [A-133]

[A-134] [A-135] [A-136]

[A-137] [A-138] [A-139]

[A-140] [A-141] [A-142]

[A-143] [A-144] [A-145]

The compound for an organic optoelectronic device may be represented by any one of the following formulas (B-1) to (B-72).

[B-1] [B-2] [B-3]

[B-4] [B-5] [B-6]

[B-7] [B-8] [B-9]

[B-10] [B-11] [B-12]

[B-13] [B-14] [B-15]

[B-16] [B-17] [B-18]

[B-19] [B-20] [B-21]

[B-22] [B-23] [B-24]

[B-25] [B-26] [B-27]

[B-28] [B-29] [B-30]

[B-31] [B-32] [B-33]

[B-34] [B-35] [B-36]

[B-37] [B-38] [B-39]

[B-40] [B-41] [B-42]

[B-43] [B-44] [B-45]

[B-46] [B-47] [B-48]

[B-49] [B-50] [B-51]

[B-52] [B-53] [B-54]

[B-55] [B-56] [B-57]

[B-58] [B-59] [B-60]

[B-61] [B-62] [B-63]

[B-64] [B-65] [B-66]

[B-67] [B-68] [B-69]

[B-70] [B-71] [B-72]

The compound for organic optoelectronic devices may have a molecular weight of 900 or less.

The compound for organic optoelectronic devices may have a molecular weight of 600 or less.

The organic optoelectronic device may be any one selected from the group consisting of organic optoelectronic devices, organic light emitting devices, organic solar cells, organic transistors, organic photoconductor drums, and organic memory devices.

In another embodiment of the present invention, at least one organic thin film layer interposed between an anode and a cathode and between at least one anode and a cathode is provided, wherein at least one of the organic thin film layers is formed of the above- And a compound for an organic optoelectronic device according to an embodiment of the present invention.

The organic thin film layer may be any one 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 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.

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

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 C30 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.

The alkyl group may be branched, straight-chain or cyclic.

"Alkenyl group" means a functional group in which at least two carbon atoms are composed of at least one carbon-carbon double bond, and "alkynyl group" means that at least two carbon atoms have at least one carbon- Quot; means a functional group formed by bonding.

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, cyclopropyl group, cyclobutyl group, cyclopentyl 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, 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. More specifically, it may be similar to the characteristic of pushing electrons.

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. More specifically, it may be similar to the characteristic of attracting electrons.

The compound for an organic optoelectronic device according to an embodiment of the present invention may have a core structure including, for example, fused bis-indole. Some carbon atoms in the core structure may be substituted with nitrogen.

More specifically, one embodiment of the present invention may have a substituent having an electron characteristic and / or a substituent having a hole characteristic selectively in the core structure.

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. Or an electron injecting material or an electron transporting material may also be used.

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 an organic optoelectronic device may be represented by the following formula (1).

[Chemical Formula 1]

In Formula 1, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R" -, X ¹ to X ⁸ are independently of each other, -CR'- or -N-, X ¹ to X ⁸ independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , Ar ² , R 'and R "are, independently of each other, hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted Or a substituted or unsubstituted C2 to C20 acyloxy group, a substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted Or a substituted or unsubstituted C1 to C20 sulfamoylamino group, a substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, C1 to C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, any one of X ¹ to X ⁴ is -CR ' -, wherein R 'means a bond with an adjacent substituent, and any one of X ⁵ to X ⁸ is -CR'-, wherein R' means a bond with an adjacent substituent, A few of Ar ¹ and Ar ² Is a substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic, L ¹ and L ² are, independently of each other, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 A substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, and n1 and n2 are each independently any one of an integer of 0 to 3 M1 and m2 are each independently any one of 0 to 3, and m1 and m2 are not 0 at the same time.

The structure as shown in Formula 1 is excellent in the processability of the device and can improve the efficiency of the device when applied to the device.

The organic optoelectronic compound represented by Formula 1 may have a molecular weight of 900 or less. In general, when the molecular weight of the compound is small, the stability of the material can be secured due to the low deposition temperature during the deposition process.

More specifically, the molecular weight may be in the range of 450 to 810. More specifically, it may be a molecular weight of about 530 to 682. [ More specifically, it may be 600 or less.

Also, in order to reinforce the electronic characteristics of the compound, at least one of Ar ¹ and Ar ² may be a substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic.

More specifically, Y ¹ and Y ² may be independently of each other -O-, -S-, -S (O ₂ ) -, or -NR'-. Y ¹ and Y ² may be the same or different from each other. However, the present invention is not limited thereto.

More specifically, Ar ¹ , Ar ² , R ', and R''independently of each other represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl 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 pyrazinyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, Substituted or unsubstituted pyrazolyl groups, substituted or unsubstituted imidazolyl groups, substituted or unsubstituted thiazolyl groups, substituted or unsubstituted oxazolyl groups, substituted or unsubstituted pyrazolyl groups, substituted or unsubstituted pyrazolyl groups, substituted or unsubstituted pyrazolyl groups, A substituted thiazolyl 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 pyrazinyl group, a substituted or unsubstituted pyrazinyl group, Substituted or unsubstituted indolyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted phenoxyl group, But are not limited thereto.

More specifically, R 'and R " may be, independently of each other, any of the following substituents.

In addition, the conjugation length of the entire compound can be determined by selectively controlling the L ¹ and L ² , and the triplet energy band gap can be controlled therefrom. This makes it possible to realize the characteristics of materials required for organic optoelectronic devices. In addition, it is possible to control the triplet energy band gap by changing the bonding position of the ortho, para, and meta.

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 phenanthryl group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-tert A phenyl group, a substituted or unsubstituted perylenyl group and the like.

More specifically, L ¹ and / or L ² may be a phenylene group. When L ¹ and / or L ² is a phenylene group, both side core moieties may be bonded to ortho, meta or para, based on the phenylene group.

X ¹ to X ⁸ may all be -CR'-. In this case, the thermal stability of the compound can be improved.

In addition, at least one of X ¹ to X ⁸ may be N. In this case, the electronic characteristics of the compound can be finely adjusted, thereby improving the efficiency of the device.

Y ² may be -NR'-, and Y ¹ may be -NR'- or -S-. In this case, the compound can have an appropriate level of energy level, so that the efficiency of the device can be improved when the device is applied.

Y ¹ and Y ² may all be -NR'-. In this case, the sublimation characteristics of the compound can be improved and the process characteristics can be improved.

More specifically, Y ² may be -NR'-, and Y ¹ may be -CR'R "- or -SiR'R" - ". However, the present invention is not limited thereto.

More specifically, Y ² may be -CR'R "-, and Y ¹ may be -SiR'R"'-. However, the present invention is not limited thereto.

The substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electron characteristic is a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, A substituted or unsubstituted thiazolyl group, a substituted pyrimidinyl group, a substituted or unsubstituted thiazinyl group, or a combination thereof.

More specifically, the substituted or unsubstituted C2 to C30 heteroaryl group having the above-mentioned electronic characteristic may be any one of the following formulas (X-1) to (X-15). However, the present invention is not limited thereto.

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

[Formula X-3] [Formula X-4]

[Formula X-5] [Formula X-6]

[Formula X-7] [Formula X-8] [Formula X-9] Formula [X-10]

[Formula X-11] [Formula X-12] Formula [X-13]

[Formula X-14] [Formula X-15]

More specifically, the compound for an organic optoelectronic device may be represented by the following formula (2).

(2)

In Formula 2, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R"'-, X ¹ to X ⁸ independently of one another are -CR'- or -N-, X ¹ to X ⁸ are independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , R' And R " are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine groups, nitro, carboxyl, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group , A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, Substituted or unsubstituted C2 to C20 acyloxy groups, substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C1 to C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, any one of X ¹ to X ⁴ are ring -CR'- and, at this time, the R 'is wherein Ar ¹ means a bond with a neighboring substituent, and is a property having an electron, a substituted or unsubstituted C2 to C30 heteroaryl ring, m1 is 1 or 2.

However, one embodiment of the present invention is not limited to the structure of Formula 2 above.

More specifically, the compound for an organic optoelectronic device may be represented by the following formula (3).

(3)

In Formula 3, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R"'-, X ¹ to X ⁸ independently of one another are -CR'- or -N-, X ¹ to X ⁸ are independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , R' And R " are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine groups, nitro, carboxyl, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group , A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, Substituted or unsubstituted C2 to C20 acyloxy groups, substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C1 to C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, any one of X ¹ to X ⁴ are ring -CR'- , Wherein R 'represents a bond to an adjacent substituent, and Ar ¹ represents a substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic.

As shown in Formula 3, when Ar ¹ is bonded to the para position based on phenylene as a linking group, the efficiency of the device can be improved. However, the present invention is not limited thereto.

More specifically, the compound for an organic optoelectronic device may be represented by the following general formula (4).

[Chemical Formula 4]

In Formula 4, Y ¹ and Y ² independently represent -O-, -S-, -S (O ₂ ) -, -CR'R "-, -SiR'R"'-, X ¹ to X ⁸ independently of one another are -CR'- or -N-, X ¹ to X ⁸ are independently of one another or form a fused ring with an adjacent substituent, Ar ¹ , R' And R " are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine groups, nitro, carboxyl, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group , A substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, Substituted or unsubstituted C2 to C20 acyloxy groups, substituted or unsubstituted C2 to C20 acylamino groups, substituted or unsubstituted C2 to C20 alkoxycarbonylamino groups, substituted or unsubstituted C7 to C20 aryloxycarbonylamino groups, A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 alkylthiol group, C1 to C20 heterocycloalkyl thiol group, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, any one of X ¹ to X ⁴ are ring -CR'- , Wherein R 'represents a bond to an adjacent substituent, and Ar ¹ represents a substituted or unsubstituted C2 to C30 heteroaryl group having an electron characteristic.

When Ar ¹ is bonded to the meta-position based on phenylene as a linking group as shown in Formula 4, the sublimation temperature of the compound is relatively decreased, thereby improving the processability in application of the device. However, the present invention is not limited thereto.

Specific examples of the compound for an organic optoelectronic device include compounds represented by the following formulas A-1 to A-145. However, the present invention is not limited thereto.

[A-1] [A-2] [A-3]

[A-4] [A-5] [A-6]

[A-7] [A-8] [A-9]

[A-10] [A-11] [A-12]

[A-13] [A-14]

[A-15] [A-16]

[A-17] [A-18]

[A-19] [A-20]

[A-21] [A-22]

[A-23] [A-24] [A-25]

[A-26] [A-27] [A-28]

[A-29] [A-30] [A-31]

[A-32] [A-33] [A-34]

[A-35] [A-36]

[A-37] [A-38]

[A-39] [A-40] [A-41]

[A-41] [A-42] [A-43]

[A-44] [A-45] [A-46]

[A-47] [A-48] [A-49]

[A-50] [A-51] [A-52]

[A-53] [A-54] [A-55]

[A-56] [A-57] [A-58]

[A-59] [A-60] [A-61]

[A-62] [A-63] [A-64]

[A-65] [A-66] [A-67]

[A-68] [A-69]

[A-70] [A-71]

[A-72] [A-73]

[A-74] [A-75] [A-76]

[A-77] [A-78] [A-79]

[A-80] [A-81]

[A-82] [A-83]

[A-84] [A-85]

[A-86] [A-87]

[A-88] [A-89]

[A-90] [A-91] [A-92] [A-93]

[A-94] [A-95] [A-96]

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

[A-101] [A-102] [A-103]

[A-104]

[A-105] [A-106] [A-107]

[A-108] [A-109] [A-110]

[A-111] [A-112] [A-113] [A-114]

[A-115] [A-116]

[A-117] [A-118] [A-119]

[A-120] [A-121] [A-122]

[A-123] [A-124]

[A-125] [A-126] [A-127]

[A-128] [A-129] [A-130]

[A-131] [A-132] [A-133]

[A-134] [A-135] [A-136]

[A-137] [A-138] [A-139]

[A-140] [A-141] [A-142]

[A-143] [A-144] [A-145]

More specifically, the compound for an organic optoelectronic device may be represented by any one of the following formulas (B-1) to (B-72). However, the present invention is not limited thereto.

[B-1] [B-2] [B-3]

[B-4] [B-5] [B-6]

[B-7] [B-8] [B-9]

[B-10] [B-11] [B-12]

[B-13] [B-14] [B-15]

[B-16] [B-17] [B-18]

[B-19] [B-20] [B-21]

[B-22] [B-23] [B-24]

[B-25] [B-26] [B-27]

[B-28] [B-29] [B-30]

[B-31] [B-32] [B-33]

[B-34] [B-35] [B-36]

[B-37] [B-38] [B-39]

[B-40] [B-41] [B-42]

[B-43] [B-44] [B-45]

[B-46] [B-47] [B-48]

[B-49] [B-50] [B-51]

[B-52] [B-53] [B-54]

[B-55] [B-56] [B-57]

[B-58] [B-59] [B-60]

[B-61] [B-62] [B-63]

[B-64] [B-65] [B-66]

[B-67] [B-68] [B-69]

[B-70] [B-71] [B-72]

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 may 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, 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 A-141

The A-141 compound shown as a more specific example of the compound for organic photoelectric conversion of the present invention was synthesized through the route shown in the following reaction scheme 1.

[Reaction Scheme 1]

(47.01 mmol) of Compound A, 15.047 g (56.41 mmol) of Compound B and 2.16 g (2.35 mmol) of tetrakis (triphenylphosphine) palladium (0) 12.995 g (94.02 mmol) of potassium carbonate was suspended in THF / toluene / distilled water 100/100/100 mL, followed by reflux stirring for 18 hours. After completion of the reaction, reduce to room temperature and add 300 mL of methanol. After stirring, precipitate is filtered and washed with methanol and distilled water. Dissolve the solid in toluene to 650 mL and filter through silica. Toluene and monochlorobenzene are melted by heating in a mixed solvent of 220/220 mL. Fill the solvent to about 110 mL and recrystallize by lowering the temperature. 18.0 g (yield 72%) of A-141 compound was obtained.

< ¹ H-NMR (300 MHz, CDCl 3): 8.93 (d, 1 H); 8.44 (d, 4H); 8.06 (s, 1 H); 7.95 (m, 1 H); 7.64 (m, 11H); 7.48 (d, 1 H); 7.43 (d, 1 H); 7.38 (m, 1 H); 7.30 (m, 2H) >

Example  2: Synthesis of A-143

[Reaction Scheme 2]

In Example 1, 15.105 g (56.42 mmol) of Compound C was used instead of Compound B, and the reaction was carried out in the same manner. 21.0 g (yield 84%) of A-143 compound was obtained.

<^1> H-NMR (300 MHz, CDCl3): 9.00 (d, IH); 8.93 (m, 4 H); 8.00 (m, 1 H); 7.65 (m, 10 H); 7.58 (d, 1 H); 7.55 (d, 1 H); 7.45 (d, 1 H); 7.38 (m, 1 H); 7.33 (m, 2H) &gt;

Example  3: Synthesis of A-136

[Reaction Scheme 3]

In Example 1, 20 g (47.01 mmol) of Compound D was used instead of Compound A, and the reaction was carried out in the same manner. 20.5 g (yield 82%) of A-136 compound was obtained.

<^1> H-NMR (300 MHz, CDCl3): 8.78 (s, IH); 8.70 (d, 1 H); 8.17 (m, 4 H); 8.01 (d, 1 H); 7.96 (s, 1 H); 7.85 (m, 1 H); 7.74 (s, 5 H); 7.56 (m, 6 H); 7.42 (m, 1 H); 7.31 (m, 2H)

(Production of organic light emitting device)

The organic light emitting device generally has a stack structure of an anode / an organic light emitting layer / a cathode and includes an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / an electron transporting layer / an electron injecting layer / a cathode or an anode / a hole injecting layer / a hole transporting layer / Electron transport layer / electron injection layer / cathode or structure without an electron injection layer in the above lamination structure, the structure in which the electron injection layer does not exist in the layer / electron transport layer / electron injection layer / cathode or anode / hole injection layer / hole generating layer / hole transport layer / And the compound represented by Formula 1 may be used as a light emitting layer material.

Manufacturing example  One

The ITO glass substrate was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically washed in acetone isopropyl alcohol and pure water for 15 minutes, and then subjected to UV ozone cleaning for 30 minutes. Next, m-MTDATA was vacuum deposited at a deposition rate of 1 Å / sec on the layer to form a hole injection layer having a thickness of 600 Å, and a-NPD was vacuum deposited to a thickness of 300 Å at a deposition rate of 1 Å / sec to form a hole transport layer Respectively. Subsequently, a dopant material, Ir (ppy) 3, and the compound of Example 1 were vapor deposited at a deposition rate of 0.1 Å / sec and 1 Å / sec, respectively, to a thickness of 400 Å over the hole transport layer to form a light emitting layer. Subsequently, (BAlq) was vacuum deposited on the light emitting layer at a deposition rate of 1 ANGSTROM / sec to a thickness of 50 ANGSTROM to form a hole blocking layer. Thereafter, an Alq3 compound was vacuum-deposited to a thickness of 300 Å on the top to form an electron transporting layer. LiF 10 Å (electron injection layer) and Al 2000 Å (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device. This is called sample 1.

Manufacturing example  2

The procedure of Example 1 was repeated except that the compound of Example 2 was used instead of the compound of Example 1 as the host in Production Example 1, and ITO / m-MTDATA (600 Å) / a-NPD (300 Å) / Example 2 + 10% (Ir (ppy) 3) (400 Å) / Balq (50 Å) / Alq3 (300 Å) / LiF (10 Å) / Al (2000 Å). This is referred to as sample 2.

Manufacturing example  3

M-MTDATA (600 Å) / a-NPD (600 Å) was prepared in the same manner as in Example 1, except that the compound of Example 3 was used instead of the compound of Example 1 (300 Å) / Example 3 + 10% (Ir (ppy) 3) (400 Å) / Balq (50 Å) / Alq3 (300 Å) / LiF (10 Å) / Al (2000 Å). This is called sample 3.

compare Manufacturing example  One

In the same manner as in Example 1 except that CBP was used in place of the compound of Example 1 as the host in Production Example 1, ITO / m-MTDATA (600 Å) / a-NPD (300 Å) / CBP Alq 3 (300 Å) / LiF (10 Å) / Al (2000 Å) was formed on the substrate.

The properties of Production Examples 1 to 3 and Comparative Production Example 1 were evaluated. The evaluation criteria are as follows. The results are shown in Table 1 below.

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

For the manufactured organic light emitting device, the current flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while raising the voltage from -5 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 thus manufactured, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from -5 V to 10 V, and the results were obtained.

(3) Measurement of luminous efficiency

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

Luminance
(cd / m ² ) Current efficiency
(cd / A) Driving voltage
(V) Production Example 1 3500 35 6.2 Production Example 2 3500 42 6.0 Production Example 3 3500 47 5.8 Comparative Preparation Example 1 3500 30 8.1

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 (20)

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

In Formula 1,
One of Y ¹ and Y ² is -NR'- and the other of Y ¹ and Y ² is -O- or -S-,
X ¹ to X ⁸ independently of one another are -CR'- or -N-,
X ¹ to X ⁸ independently of one another or form a fused ring with an adjacent substituent,
Ar ¹ , Ar ² and R 'are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, Or a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, C20 aryloxy group, a substituted or unsubstituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group , A substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfa A substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group , A substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
Wherein one of X ¹ to X ⁴ is -CR'-, wherein R 'means a bond with an adjacent substituent,
Wherein any one of X ⁵ to X ⁸ is -CR'-, wherein R 'means a bond with an adjacent substituent,
At least one of Ar ¹ and Ar ² is a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, An unsubstituted thiazolyl group,
L ¹ and L ² each independently represent a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted A C2 to C30 heteroarylene group or a combination thereof,
n1 and n2 are each independently an integer of 0 to 3,
m1 and m2 are each independently an integer of 1 to 3;
delete delete The method according to claim 1,
Wherein the compound for an organic optoelectronic device is represented by the following Formula 2:
(2)

In Formula 2,
One of Y ¹ and Y ² is -NR'- and the other of Y ¹ and Y ² is -O- or -S-,
X ¹ to X ⁸ independently of one another are -CR'- or -N-,
X ¹ to X ⁸ independently of one another or form a fused ring with an adjacent substituent,
R 'is independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted Or an unsubstituted or substituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, A substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino , A substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group, a substituted Or an unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
Wherein one of X ¹ to X ⁴ is -CR'-, wherein R 'means a bond with an adjacent substituent,
Wherein Ar ¹ is a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group ,
m1 is 1 or 2;
The method according to claim 1,
Wherein the compound for an organic optoelectronic device is represented by the following Formula 3:
(3)

In Formula 3,
One of Y ¹ and Y ² is -NR'- and the other of Y ¹ and Y ² is -O- or -S-,
X ¹ to X ⁸ independently of one another are -CR'- or -N-,
X ¹ to X ⁸ are independently present or form a fused ring with an adjacent substituent,
R 'is independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted Or an unsubstituted or substituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, A substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino , A substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group, a substituted Or an unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
Wherein one of X ¹ to X ⁴ is -CR'-, wherein R 'means a bond with an adjacent substituent,
Wherein Ar ¹ is a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group .
The method according to claim 1,
Wherein the compound for an organic optoelectronic device is represented by the following Formula 4:
[Chemical Formula 4]

In Formula 4,
One of Y ¹ and Y ² is -NR'- and the other of Y ¹ and Y ² is -O- or -S-,
X ¹ to X ⁸ independently of one another are -CR'- or -N-,
X ¹ to X ⁸ are independently present or form a fused ring with an adjacent substituent,
R 'is independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a carboxyl group, a ferrocenyl group, C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryloxy group, a substituted Or an unsubstituted or substituted C3 to C40 silyloxy group, a substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C2 to C20 alkoxycarbonyl group, a substituted or unsubstituted C2 to C20 acyloxy group, A substituted or unsubstituted C2 to C20 acylamino group, a substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 to C20 sulfamoylamino , A substituted or unsubstituted C1 to C20 sulfonyl group, a substituted or unsubstituted C1 to C20 alkylthiol group, a substituted or unsubstituted C6 to C20 arylthiol group, a substituted or unsubstituted C1 to C20 heterocyclothiol group, a substituted Or an unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,
Wherein one of X ¹ to X ⁴ is -CR'-, wherein R 'means a bond with an adjacent substituent,
Wherein Ar ¹ is a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group .
The method according to claim 1,
And X &^lt; ¹ &gt; to X &^lt; ^{8 & gt} ; are all -CR &lt; ¹ &gt; -.
delete The method according to claim 1,
Y ² is -NR'-, and Y ¹ is -S-.
delete delete delete delete 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-89, A-101 to A-110 and A-134 to A-145.
[A-1] [A-2] [A-3]

[A-4] [A-5] [A-6]

[A-7] [A-8] [A-9]

[A-10] [A-11] [A-12]

[A-13] [A-14]

[A-15] [A-16]

[A-17] [A-18]

[A-19] [A-20]

[A-21] [A-22]

[A-23] [A-24] [A-25]

[A-26] [A-27] [A-28]

[A-29] [A-30] [A-31]

[A-32] [A-33] [A-34]

[A-35] [A-36]

[A-37] [A-38]

[A-39] [A-40] [A-41]

[A-41] [A-42] [A-43]

[A-44] [A-45] [A-46]

[A-47] [A-48] [A-49]

[A-50] [A-51] [A-52]

[A-53] [A-54] [A-55]

[A-56] [A-57] [A-58]

[A-59] [A-60] [A-61]

[A-62] [A-63] [A-64]

[A-65] [A-66] [A-67]

[A-68] [A-69]

[A-70] [A-71]

[A-72] [A-73]

[A-74] [A-75] [A-76]

[A-77] [A-78] [A-79]

[A-80] [A-81]

[A-82] [A-83]

[A-84] [A-85]

[A-86] [A-87]

[A-88] [A-89]

[A-101] [A-102] [A-103]

[A-104]

[A-105] [A-106] [A-107]

[A-108] [A-109] [A-110]

[A-134] [A-135] [A-136]

[A-137] [A-138] [A-139]

[A-140] [A-141] [A-142]

[A-143] [A-144] [A-145]

delete The method according to claim 1,
Wherein the compound for organic optoelectronic devices has a molecular weight of 900 or less.
The method according to claim 1,
Wherein the compound for organic optoelectronic devices has a molecular weight of 600 or less.
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 claim 1.
19. The method of claim 18,
Wherein the compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in a light emitting layer.
18. A display device comprising the organic light emitting element according to claim 18.

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