WO2014104600A1

WO2014104600A1 - Compound for organic optoelectronic device, organic light-emitting device containing same, and display apparatus including said organic light-emitting device

Info

Publication number: WO2014104600A1
Application number: PCT/KR2013/011005
Authority: WO
Inventors: 장유나; 이상신; 홍진석; 강의수; 김준석; 류동완; 유동규; 이승재; 이한일; 정성현; 조영경; 채미영; 허달호
Original assignee: 제일모직 주식회사
Priority date: 2012-12-31
Filing date: 2013-11-29
Publication date: 2014-07-03
Also published as: KR20170098759A; KR20140088003A; KR101811327B1

Abstract

Provided are a compound for an organic optoelectronic device represented by chemical formula 1, an organic light-emitting device containing same, and a display apparatus including said organic light-emitting device. The structure of the compound for the organic optoelectronic device represented by chemical formula 1 is disclosed in the present specification. By providing the compound for the organic optoelectronic device, an organic optoelectronic device having properties such as high efficiency and long lifespan can be manufactured.

Description

【Specification】

[Name of invention]

Compound for an organic optoelectronic device, an organic light emitting device comprising the same and the

Display device including organic light emitting device

Technical Field

A display device comprising an organic light emitting device.

Background Art

An organic optoelectric 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 divided into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes, respectively, to the current source (voltage source). It is an electronic device of the type used.

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

Examples of an organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which are injecting or transporting holes for driving the device. Requires electron injection or transport material, or a luminescent material

In particular, organic light emitting diodes (OLEDs) have recently become flat panels.

The demand for flat panel displays is increasing. In general, organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.

Such an organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has a structure in which a functional organic material layer is inserted between an anode and a cathode. In this case, the organic material layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.

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

Recently, it has been known that not only fluorescent light emitting materials but also phosphorescent light emitting materials can be used as light emitting materials of organic light emitting devices, and the phosphorescent light emission is generated by the transfer of electrons from the ground state to the excited state, It is composed of a mechanism in which singlet excitons are non-luminescent transition into triplet excitons, and then triplet excitons are emitted to the ground state.

As described above, the material used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like depending on their functions.

In addition, the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors. On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. In order to increase luminous efficiency and stability through the host / dopant system can be used as a light emitting material.

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

In addition, the low molecular weight organic light emitting device is a device in the form of a thin film by vacuum deposition method As it is manufactured, the efficiency and lifespan performance are good, and the polymer organic light emitting diode has an advantage of low initial investment cost and large area using an inkjet or spin coating method.

Both low molecular weight organic light emitting diodes and high molecular weight organic light emitting diodes are attracting attention as next-generation displays because they have advantages such as self-luminous, high speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range. In particular, compared to conventional LCD (liquid crystal display) as a self-luminous type, even in a dark place or outside light is good cyanity, and no backlight is required, it can reduce the thickness and weight to 1/3 of the LCD.

In addition, the voice response speed is 1000 times faster than LCD, which makes it possible to realize a perfect video without afterimages. Therefore, it is expected to be spotlighted as the most suitable display in line with the recent multimedia era. Based on these advantages, we have made rapid technological developments with efficiency of 80 times and lifespan over 100 times since the first development in the late 1980s. Increasingly, large-scaled developments are being made with the introduction of organic light emitting diode panels.

In order to increase the size, the luminous efficiency must be increased and the life of the device must be accompanied. To this end, it is necessary to develop a stable and efficient organic material layer for an organic light emitting device.

[Detailed Description of the Invention]

[Technical problem]

It is to provide a compound for an organic optoelectronic device capable of providing an organic optoelectronic device having characteristics such as high efficiency and long life.

An organic light emitting device comprising the compound for an organic optoelectronic device and the

A display device including an organic light emitting device is provided.

Technical Solution

In one embodiment of the present invention, a compound for an organic optoelectronic device represented by the following Chemical Formula 1 is provided. [Formula 1]

In Formula 1, Ar ¹ is a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, L is a substituted or unsubstituted C2 to C6 An alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,? Is 0 to 3 Is any integer, X ¹ to X ⁸ are independently of each other, -Ν- or -CR'-, any one of X ¹ to X ⁸ is -Ν-, R ¹ to R ¹⁰ and R ' Independently of each other, hydrogen, deuterium, halogen group, cyano group, hydroxy group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted Or an unsubstituted C6 to C30 aryl group, substituted Or an 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 Substituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxy Carbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20

Sulfamoylamino groups, substituted or unsubstituted C1 to C20 sulfonyl groups, substituted or unsubstituted C1 to C20 alkylthio groups, substituted or unsubstituted C6 to C20 arylthiol groups, substituted or unsubstituted C1 to C20 heterocyclothiols Groups, substituted or unsubstituted C1 to C20 ureide groups, substituted or unsubstituted C3 to C40 silyl groups, or a combination thereof. In another embodiment of the present invention, in the organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least one layer of the organic thin film layer for the organic optoelectronic device It provides an organic light emitting device comprising a compound.

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

Advantageous Effects

The organic optoelectronic device including the compound for an organic optoelectronic device has excellent electrochemical and thermal stability, excellent life characteristics, and high luminous efficiency even at a low driving voltage.

[Brief Description of Drawings]

1 and 2 are cross-sectional views showing various embodiments of an organic light emitting device that may be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.

100: organic light emitting element 110: cathode

120: anode 105: organic thin film layer

130: light emitting layer 140: hole transport layer

[Best form for implementation of the invention]

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.

In the present specification, "substituted", unless otherwise defined, at least one hydrogen of a substituent or a compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, fluoro group,

It means substituted with a C1 to C10 trifluoroalkyl group or a cyano group such as a trifluoromethyl group.

In addition, the substituted halogen, hydroxy, amino, substituted or unsubstituted C1 To C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluorine Two adjacent substituents among C1 to C10 trifluoroalkyl groups or cyano groups such as a ro group and a trifluoromethyl group may be fused to form a ring.

As used herein, unless otherwise defined, "hetero" means containing 1 to 3 heteroatoms selected from the group consisting of Ν, Ο, S and Ρ within one functional group, and the rest are carbon.

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

As used herein, unless otherwise defined, an "alkyl group" is aliphatic

It means a hydrocarbon group. The alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.

The alkyl group may be an alkyl group that is 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, a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, with methyl, ethyl, propyl, iso-propyl, η-butyl, iso-butyl, _sec -butyl and t-butyl Selected from the group consisting of:

Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.

"Aryl group" 'means a substituent in which all elements of the cyclic substituent have a p-orbital, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic (Ie, rings that share adjacent pairs of carbon atoms).

"Heteroaryl group" means containing 1 to 3 heteroatoms selected from the group consisting of N, 0, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms. In the present specification, the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer. More specifically, it may be similar to the property of repelling electrons.

In addition, an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer. More specifically, it may be similar to the property of attracting electrons.

In one embodiment of the present invention, it is possible to provide a compound for an organic optoelectronic device represented by the formula (1)

[Formula 1]

In Formula 1, Ar ¹ is a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C1 to C30 heteroaryl group, L is a substituted or unsubstituted C2 to C6 An alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,? Is 0 to 3 Is any integer, X ¹ to X ⁸ are independently of each other, -Ν- or -CR'-, any one of X ¹ to X ⁸ is -Ν-, R ¹ to R ¹⁰ and R ' Independently of each other, hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine group, nitro group carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted Or unsubstituted C6 to C30 aryl group, 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 silyloxy, a substituted or unsubstituted C40 ring unsubstituted C1 To C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonyl Amino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20

Sulfamoylamino groups, substituted or unsubstituted C1 to C20 sulfonyl groups, substituted or unsubstituted C1 to C20 alkylthiol groups, substituted or unsubstituted C6 to C20 arylthiol groups, substituted or unsubstituted C1 to C20 heterocyclothiols Groups, substituted or unsubstituted C1 to C20 ureide groups, substituted or unsubstituted C3 to C40 silyl groups, or a combination thereof.

The compound represented by Chemical Formula 1 may have a core structure including a spiro compound. More specifically, the core structure may have a carbazole moiety. Since the core structure has bipolar properties in one molecule, when used as a phosphorescent host material of an organic optoelectronic device, the efficiency and lifespan of the device can be improved.

In addition, the compound for an organic optoelectronic device represented by Formula 1 may be a compound having a variety of energy band gapol by introducing a variety of other substituents to the substituents substituted in the core portion and the core portion.

By using a compound having an appropriate energy level in the organic optoelectronic device according to the substituent of the compound, the hole transfer ability or electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent in organic chemical and thermal stability It is possible to improve the life characteristics when driving the device.

More specifically, in one embodiment of the present invention, a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heteroaryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naph Tyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted Substituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted perenyl group, substituted or

Unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrylyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted Or an unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or Unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofura Nyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or Unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted Acridinyl group, substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenthiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted fluorenyl group, substituted May be a unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a combination thereof, are not limited.

In addition, the L may be selectively adjusted to determine the conjugation length of the entire compound, from which the triplet energy bandgap can be adjusted. Through this, it is possible to realize the characteristics of the material required in the organic optoelectronic device. In addition, the triplet energy bandgap can be adjusted by changing the bonding position of Olso, Para and Meta.

Specific examples of the L 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 anthracenylene group, Substituted or unsubstituted phenanthryl group, substituted or unsubstituted pyrenylene group, substituted or unsubstituted fluorenylene group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or Unsubstituted perrylenyl group. More specifically, L may be independently a phenylene group. When L is a phenylene group, both core portions may be bonded to ortho, meta or para based on the phenylene group.

More specifically, Ar ¹ is a substituted or unsubstituted amine group, substituted or unsubstituted

C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heteroaryl group, the heteroaryl group containing nitrogen in the range of Ar ¹ except for the carbazolyl group is excluded. When the heteroaryl group including the nitrogen except the carbazolyl group is excluded from the Ar ¹ range, the HT property of the compound may be increased to improve the bipolar property of the entire compound. For example, containing nitrogen except the carbazolyl group Specific examples of the heteroaryl group, that is, a heteroaryl group including nitrogen having ET characteristics include a pyridinyl group, a pyrimidinyl group, a triazinyl group, and the like. It is preferably excluded from the scope of the Ar ^1.

Here, the character of ΤΤ refers to a characteristic in which holes can be formed by donating electrons when an electric field is applied, and a hole formed at an anode into a light emitting layer having conductive properties along the HOMO level is formed in the light emitting layer. It means a characteristic that facilitates the movement of the hole to the anode and in the light emitting layer.

In addition, the ET characteristic refers to a characteristic in which electrons can be received when an electric field is applied, and has a conductivity characteristic along the LUMO level, injecting electrons formed in the cathode into the light emitting layer, moving electrons formed in the light emitting layer to the cathode, and in the light emitting layer. It means a property that facilitates the movement of.

More specifically, Ar ¹ may be a substituted or unsubstituted C6 to C30 aryl group. In this case, while the molecular weight of the compound is small, the HT characteristics may be increased, thereby improving the bipolar characteristics.

More specifically, Ar ¹ may be a substituent represented by the following formula S-1. The use of arylamine substituents with strong hole properties may increase the hole properties of the compound, thereby improving the bipolar properties of the compound.

[Formula S-1]

In Formula S-1, Ar ² and Ar ³ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and * is a linking point.

More specifically, Ar ¹ may be a substituent represented by the following formula S-2. More specifically, when the substituent having a strong hole property is used, the hole property of the compound may be increased to improve the bipolar property of the compound. [Formula S-2]

In Formula S-2, X ⁹ is -NR '-,-Ο-, or -S-, and R ¹¹ and R ¹² and R' are each independently hydrogen, deuterium, a halogen group, a cyano group, or a hydroxyl group. , Amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 To C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 ah Real, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, substituted or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20

Alkoxycarbonylamino group, substituted or unsubstituted C7 to C20

Aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthiol group, substituted or unsubstituted C6 to C20 aryl A thil 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, and * is a linking point. More specifically, Ar ¹ may be a substituent represented by the following formula S-3. Using a substituent of a carbazole derivative having a strong hole property may increase the hole property of the compound, thereby improving the bipolar property of the compound.

[Formula S-3]

In Formula S-3, R ¹¹ and R ¹² are each independently 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. Carboxyl group, ferrocenyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C1 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, Substituted or unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted Substituted C2 to C20 acyloxy group, substituted or unsubstituted C2 to C20 acylamino group substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20

Sulfamoylamino groups, substituted or unsubstituted C1 to C20 sulfonyl groups, substituted or unsubstituted C1 to C20 alkylthiol groups, substituted or unsubstituted C6 to C20 arylthiol groups, substituted or unsubstituted C1 to C20 heterocycloti Group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof, and * is a linking point.

More specifically, Ar ¹ may be a substituent represented by the following formula S-4. In such a case, the thermal stability may be increased by increasing the Tg by increasing molecular weight of the compound and structurally.

[Formula S-4]

In Formula S-4, * is a connection point.

More specifically, Ar ¹ may be a substituent represented by the following formula S-5 or S-6. In this case, the hole properties may be increased while the molecular weight is small, so that the bipolar properties may be improved. [Formula S-5] [Formula S-6]

In Formulas S-5 and S-6, * is a linking point.

More specifically, any one of X ¹ to X ⁸ may be -N-, and X ⁴ may be -N-. In this case, the bipolar properties of the compound can be improved by improving the electronic properties.

More specifically, any one of X ¹ to X ⁸ may be -N-, X ¹ and X ³ may be -N-, or X ² and X ⁴ may be -N-. In such cases, the electronic properties can be improved to improve the bipolar properties of the compound.

X ¹ and X ³ may be -N-, and X ² may be -C (Ph)-. In such a case, the stability of the molecule can be increased by reducing the delocalization of the intramolecular electrons.

More specifically, X ² and X ⁴ may be -N-, and X ³ may be -C (Ph)-. In this ^case, by reducing the delocalization of the electrons in the molecule it may increase the stability of the molecule. Any one of X ¹ to X ⁴ may be -N-, and any one of X ⁵ to X ⁸ may be -N-. In such a case, the stability of the molecule can be increased by reducing the delocalization of the intramolecular electrons.

Any two of X ¹ to X ⁴ may be -N-, and any two of X ⁵ to X ⁸ may be -N-. In such a case, the stability of the molecule can be increased by reducing the delocalization of the intramolecular electrons.

For more specific example, the compound for an organic optoelectronic device may be any one of the following specific compound structure. However, it is not limited thereto.

n

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

ST

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

91

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

LI

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

81

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

61

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

oz

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

ιζ

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV 22

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV 

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

οε

SOOllO / CTOZaM / X3d 009) ΐ / 0Ζ OAV

It

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

Lt

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

009) ΐ / 0Ζ OAV

6t

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

Of

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV 41

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

St

S00ll0 / CT0ZaM / X3d 009) ΐ / 0 Ζ OAV

The compound for an organic optoelectronic device may be used as a light emitting layer material of an organic light emitting device. More specifically, the compound for an organic optoelectronic device may further include a dopant represented by Chemical Formula D-1 when used as a light emitting layer material of an organic light emitting device.

[Formula D-1]

In Formula D-1, R ¹³ to R ²⁰ are each independently hydrogen, deuterium, a halogen substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 fluoroalkyl group, a substituted or unsubstituted C1 To C20 alkoxy group, substituted or unsubstituted A C1 to C20 amino group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, or a substituted or unsubstituted silyl group, and two adjacent substituents may form a fused ring.

Specific examples of the substituted or unsubstituted silyl group include trimethylsilyl group, triarylsilyl group, dialkylarylsilyl group, diarylalkylsilyl group and the like. remind

Detailed description of the organic light emitting device will be described later.

In another embodiment of the present invention, an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, wherein at least any one of the organic thin film layer comprises the compound for the organic optoelectronic device An organic optoelectronic device is provided. The compound for an organic optoelectronic device is used in an organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.

Specifically, the organic thin film layer may be a light emitting layer.

The organic optoelectronic device may be an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photosensitive drum, or an organic memory device.

More specifically, the organic optoelectronic device may be an organic light emitting device. 1 and 2 include a compound for an organic optoelectronic device according to an embodiment of the present invention

A cross-sectional view of an organic light emitting device.

Referring to FIG. 1, an organic optoelectronic device 100 according to an embodiment is positioned between an anode 120 and a cathode 110 facing each other, and between an anode 120 and a cathode 110.

An organic thin film layer 105.

The anode 120 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example. The anode 120 is, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide (ΠΌ),

Metal oxides such as indium zinc oxide (IZO); ZnO and A1 or Sn (a combination of metals and oxides such as ¾ and Sb; poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT) And conductive polymers such as polypyri and polyaniline, but are not limited thereto.

The cathode 110 is, for example, a conductor having a low work function to facilitate electron injection. It may be made, for example, of metals, metal oxides and / or conductive polymers. Cathode 110 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; Multilayer structure materials such as LiF / Al, Li0 ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca, but are not limited thereto.

The organic thin film layer 105 includes a light emitting layer 130 including the compound described above.

For example, the light emitting layer 130 may include the above-described compound alone, may include at least two kinds of the above-described compounds, or may include the above-mentioned compounds and other compounds in combination. In the case of including a compound different from the above-mentioned compound, for example, it may be included in the form of a host and a dopant, and the above-described compound may be included as a host, for example. The host can be, for example, a phosphorescent host or a fluorescent host, for example a green phosphorescent host.

When the above-mentioned compound is included as a host, the dopant may be an inorganic, organic or organic-inorganic compound and may be selected from known dopants.

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 230. The hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting insect 230 and block electrons. The hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. The above-described compound may be included in the light emitting layer 230 and / or hole auxiliary layer 140.

Although not shown, the organic thin film layer 105 of FIG. 1 or 2 may further include an electron injection layer, an electron transport layer, an auxiliary electron transport layer, a hole transport layer, an auxiliary hole transport layer, a hole injection layer, or a combination thereof. . The compounds of the present invention can be included in these organic layers. After the organic light emitting diodes 100 and 200 form an anode or a cathode on a substrate,

Dry film formation methods such as evaporation, sputtering, plasma plating and ion plating; Alternatively, the organic layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode or an anode thereon.

In another embodiment of the present invention, a display device including the organic optoelectronic device is provided. [Form for implementation of invention]

The following presents specific embodiments of the present invention. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.

Preparation of Compound for Organic Optoelectronic Devices

Example 1 Synthesis of Compound of Formula A-1

The compound of Formula A-1, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a six-step route such as Banung Formula 1 below.

[Banungsik 1]

Step 1: Synthesis of Intermediate Product (A)

20.0 g (70.70 mmol) of 2-bromoiodobenzene, 14.50 g (70.70 mmol) of 2-pyridylboronic ester and 14.66 g (106.04 mmol) of K ₂ C0 ₃ , Pd (PPh ₃ ) ₄ 1.63 g (1.41 mmmol) Suspended in 300 ml of toluene, 150 ml of distilled water and stirred under reflux for 24 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was extracted with dichloromethane, filtered with silica gel, and distilled under reduced pressure, followed by silica column with hexane ： ethyl acetate = 8: 2 (v / v),

Recrystallized with dichloromethane and normal nucleic acid to obtain 11.92 g of intermediate product (A) (yield: 72%). Obtained.

Second step; Synthesis of Intermediate Product

The intermediate product prepared in Synthetic Step 1 (A) 25.0 g (106.80 mmol) and suspended in 400 mL of tetrahydrofuran and add slowly n-BuLi 55.53 mL (138.84 mmol ) at -78 ^° C. In-78 ^° C After stirring for 3 hours, 30.44 g (117.48 mol) of 2-bromofluorenone was slowly added thereto and stirred for 24 hours. After completion of reaction, the reaction was terminated with an aqueous ammonium chloride solution, extracted with dichloromethane, and the organic layer was filtered with silica gel. The organic solution was removed and silica gel column with nucleic acid: ethyl acetate = 5: 5 (v / v) gave 35.0 g (yield: 79%) of the intermediate product (B).

Third Step: Synthesis of Intermediate Product (C)

Suspend 35.0 g ( ⁸ 4. ⁴ 8 mmol) of intermediate product (B) in 500 mL of acetic acid and slowly add 16.5 mL (253.45 mmol) of CH ₃ S0 ₃ H at room temperature. Stir for 24 hours. After completion of the reaction, the reaction was completed with 250 mL of sodium bicarbonate aqueous solution, and the resulting solid was filtered, extracted with dichloromethane and distilled water, and the organic layer was filtered with silica gel. The organic solution was removed and a silica gel column with nucleic acid: dichloromethane = 6: 4 (v / v) gave 26.8 g of an intermediate product (D) (yield: 80%).

Fourth Step: Intermediate Product (Synthesis of It)

Intermediate product (C) 25.0 g (63.09 mmol), 11.58 g (69.40 mmol) of 2-nitrobenzene boronic acid and 13.08 g (94. «mmol) of potassium carbonate, tetrakis- (triphenylphosphine) palladium (0) l . ⁴⁶ g (1.26mmmol) was suspended in 250 ml of toluene and 200 ml of distilled water, followed by stirring under reflux for 12 hours. After completion of reaction, the reaction solution was extracted with dichloromethane, filtered with silica gel, distilled under reduced pressure, and silica column was obtained to obtain 19.9 g of an intermediate product (D) (yield: 72%).

Step 5: Synthesis of Intermediate Product

Intermediate product (D) 15.0 g (34. 2 l mmol) and triethyl phosphite 29.8 mL

(171.05 mmol) was stirred at reflux for 4 hours under a stream of nitrogen. After completion of reaction, the reaction solvent was removed, and silica column with nucleic acid: dichloromethane = 6: 4 (v / v) gave 10.8 g (yield: 78%) of the intermediate product (E).

Step 6: Synthesis of Chemical Formula A-1

10.0 g (24.60 mmol) of intermediate product (E) and 5.79 g (36.90 mmol) of bromobenzene, 4.73 g (49.20 mmol) of NaO (t-Bu), 1.35 g (1.48 mmmol) of Pd ₂ (dba) ₃ were suspended in 170 mL of toluene, and then 33.51 mL (14.76 mmol) of P (t-Bu) was added thereto. Under reflux for 24 h. Extract with dichloromethane and distilled water and filter the organic layer with silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 7: 3 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid to give 10.3 g of compound of formula A-1 (yield: 87%). .

Example 2: Synthesis of Compound of Formula A-2

The compound of Chemical Formula A-2, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a three-step route as shown in Banung Formula 2.

[Bungungsik 2]

[Formula A-2]

Step 1: Synthesis of Intermediate Product (F)

20.0 boronic acid 9-phenylcarbazole 30.0 g (104.49 mmol), 2-bromoiodobenzene 4 3 ⁴ g (156.73 mmol) and potassium carbonate 43.32 g (313.47 mmol), tetrakis- (triphenylphosphine) Palladium (0) ² . To a ⁴ 1 g ⁽² .09mmmol) in toluene 4 0 ml, distilled water 210 ml After suspension, reflux was stirred for 12 hours. After completion of reaction, the reaction mixture was extracted with dichloromethane, filtered with silica gel, distilled under reduced pressure, and silica column to obtain 28.30 g of an intermediate product (F) (yield: 68%).

Second Step: Synthesis of Intermediate Product ffi)

35.37 g (88.80 mmol) of the intermediate product (F) synthesized in the first step of synthesis

Tetra-suspended in 180 mL tetrahydrofuran at -78 ^° and is in the C n-BuLi 43.0 mL (106.56 mmol) to put slowly.-78 ^° C 9H- After stirring for 3 hours teno [2,1-pyrimidin-9-aired 8.09 g (44.40 mol) of warm (9H-indeno [2, l-if] pyrimidine-9-one) was slowly added thereto and stirred for 24 hours. After the reaction was completed, the reaction was terminated with an aqueous ammonium chloride solution, followed by dichloromethane.

Extraction and the organic layer were silica gel filtered to give .59 g (yield: 79%) of intermediate product (G).

Third Step: Synthesis of Chemical Formula A-2

17.59 g (35.07 mmol) of the intermediate product (G) synthesized in the second step of synthesis

Under tetrahydrofuran and suspended in 140 mL, and ^{_{_{0 ° C BF 3 (C 2}}} H 5) 2 06.49 mL (52.61 mmol) and then quenching with sodium bicarbonate aqueous solution and then slowly put termination reaction after stirring for 12 hours at .0 ^° C The reaction was completed, the mixture was extracted with dichloromethane and the organic layer was filtered with silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 8: 2 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid to give 11.87 g of a compound of formula A-2 (yield: 70%). .

Example 3: Synthesis of Compound of Formula A-3

The compound of Formula A-3, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a one-step route as shown in Banung Formula 3.

[Banungsik 3]

[Formula A-3] First Step: Synthesis of Chemical Formula A-3

10.0 g ( ² 4.60 mmol) of the intermediate product (E) synthesized in Banung Formula 1, 11.89 g (36.90 mmol) of 4-bromophenyl 9-phenylcarbazole, 4.73 g (49.20 mmol) of NaO (t-Bu), Pd 1.35 g (1.48 mmmol) of ₂ (dba) ₃ was suspended in 170 mL of toluene, and then 33.51 mL (14.76 mmol) of P (t-Bu) was added thereto and stirred under reflux for 24 hours under a nitrogen stream. Extract with dichloromethane and distilled water and filter the organic layer with silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 8: 2 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid to give 13.54 g of a compound of formula A-3 (yield: 85%). .

Example 4: Synthesis of Compound of Formula A-4

The compound of Formula A-4, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a two-step route such as Banung Formula 4.

[Banungsik 4]

Formula A-4: Step 1: Synthesis of Intermediate Product τ>

35.37 g (88.80 mmol) of the intermediate product (F) synthesized in Banungsik 2 and

Of tetrahydrofuran and suspended in 180 mL and add slowly n-BuLi 43.0 mL (106.56 mmol ) at -78 ^{^°} C.-78 ^° C at after stirring for 3 hours 5H-Cyclopenta dipyridin-5-one 8.09 g (44.40 mol) slowly Put and stirred for 24 hours. Ammonium chloride after reaction After the reaction was complete with an aqueous solution, the mixture was extracted with dichloromethane and the organic layer was filtered through a silica gel to obtain 18.04 g of an intermediate product (H) (yield: 81%).

Second Step: Synthesis of Chemical Formula A-4

Suspend 18.00 g (35.89 mmol) of intermediate product (H) in 145 mL of tetrahydrofuran, and slowly add 06.64 mL (53.84 mmol) of BF ₃ (C ₂ H ₅ ) ₂ (under C). Stir at 0 ^° C for 12 h. After completion of reaction, after quenching with aqueous sodium bicarbonate solution, the reaction was terminated, extracted with dichloromethane, and the organic layer was filtered with silica gel.The organic solution was removed, followed by silica gel column with nucleic acid: dichloromethane = 8: 2 (v / v). The solid was recrystallized from dichloromethane and normal nucleic acid to give 12.50 g of a compound of Formula A-4 (yield: 72%).

Example 5: Synthesis of Compound of Formula A-5

The compound of Formula A-5, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a one-step route as shown in Banung Formula 5.

Scheme 5

First Step: Synthesis of Chemical Formula A-5

10.0 g (24.60 mmol) of the intermediate product (E) synthesized in Banungsik 1, 11.93 g (36.90 mmol) of 4-bromophenyl dibenzofuran, 4.73 g (49.20 mmol) of NaO (t-Bu), Pd2 (dba) After 31.35 g (1.48 mmmol) was suspended in 170 mL of toluene, 33.51 mL (14.76 mmol) of P (t-Bu) was added thereto, and the mixture was stirred under reflux for 24 hours under a nitrogen stream. Extract with dichloromethane and distilled water and filter the organic layer with silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 7 _: 3 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid. 13.57 g (yield: 85%) of the compound of formula A-5 were obtained.

Example ad-1 Synthesis of Compound A-6

The compound of Formula A-6, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a one-step route such as the following Scheme 6.

[Bandungsik 6]

[Formula A-6] First Step: Synthesis of Chemical Formula A-6

10.0 g (24.60 mmol) of the intermediate product (E) synthesized in Scheme 1, 9.13 g (29.52 mmol) of 5-bromotorphenyl, 3.55 g (36.90 mmol) of NaO (t-Bu), 0.68 g of Pd ₂ (dba) ₃ (0.74 mmmol) was suspended in 98 mL of toluene, and then 0.36 mL (1.48 mmol) of P (t-Bu) ₃ was added thereto, and the mixture was stirred under reflux for 24 hours under a nitrogen stream. Extract with dichloromethane and distilled water and filter the organics silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 7: 3 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid to give 11.71 g of a compound of formula A-6 (yield: 75%). .

Example ad-2: Synthesis of Compound of Formula A-7

The compound of Formula A-7, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a one-step route such as Ban Hung-Sik.

[Bungungsik 7]

[Formula A-7] First Step: Synthesis of Chemical Formula A-7

10.0 g (24.60 mmol) of the intermediate product (E) synthesized in Reaction Formula 1, 6.88 g (29.52 mmol) of 4-bromobiphenyl, 3.54 g (36.90 mmol) of NaO (t-Bu), Pd ₂ (dba) ₃ 0.68 After g (0.74 mmmol) was suspended in 98 mL of toluene, 0.36 mL (1.48 mmol) of P (t-Bu) ₃ was added thereto, and the mixture was stirred under reflux for 24 hours under a nitrogen stream. Extract with dichloromethane and distilled water and filter the organic layer with silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 7 _: 3 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid to obtain the compound ll.OOg (yield: 80%) of formula A-7. It was.

Example ad-3 Synthesis of Compound A-8

The compound of Formula A-8, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a one-step route as shown in the following formula.

(E)

[Formula A 一 8] First Step: Synthesis of Chemical Formula A-8

10.0 g ( ² 4. ⁶ 0 mmol) of the intermediate product (E) synthesized in Reaction Formula 1 and 9.51 g (29.52 mmol) of 3-bromo 9-phenylcarbazole, 3.55 g (36.90 mmol) of NaO (t-Bu) ), 0.68 g (0.74 mmmol) of Pd ₂ (dba) ₃ was suspended in 98 mL of toluene, and 0.36 mL (1.48 mmol) of P (t-Bu) ₃ was added thereto, followed by stirring under reflux for 24 hours. Extract with dichloromethane and distilled water and filter the organic layer with silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 7 _: 3 (Wv) to recrystallize the product solid with dichloromethane and normal nucleic acid to give 12.75 g of a compound of formula A-8 (yield: 68%).

Example ad-4: Synthesis of Compound of Formula A-9

Compound of the formula A-9 presented as a more specific example of the compound for an organic photoelectric device of the present invention was synthesized through a one-step route as shown in the following reaction. Scheme 9

First Step: Synthesis of Chemical Formula A-9

10.0 g (24.60 mmol) of the intermediate product (E) synthesized in Reaction Formula 1, 9.57 g (29.52 mmol) of 4-bromophenyldiphenylamine, 3.55 g (36.90 mmol) of NaO (t-Bu), Pd ₂ (dba ₃ ) 0.68 g (0.74 mmmol) was suspended in 98 mL of toluene, and then 0.36 mL (1.48 mmol) of P (t-Bu) ₃ was added thereto, followed by stirring under reflux for 24 hours. Extract with dichloromethane and distilled water and filter the organics silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 7: 3 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid to obtain 9.59 g (yield: 60%) of the compound of formula A-9. It was.

Example ad-5: Synthesis of Compound of Formula A-10

The compound of Formula A-10, which is presented as a specific example of the compound for an organic photoelectric device of the present invention, was synthesized through a one-step route as in Scheme 10 below.

[Banungsik 10]

[Formula A-10] First Step: Synthesis of Chemical Formula A-10

10.0 g (24.60 mmol) of the intermediate product (E) synthesized in Banungsik 1, 11.81 g (29.52 mmol) of biphenyl (4-bromophenyl) phenylamine, 3.55 g (36.90 mmol), Pd, NaO (t-Bu) ₂ (dba) ₃ 0.68 g (0.74 mmmol) was suspended in 98 mL of toluene and then 0.36 mL (1.48 mmol) of P (t-Bu) ₃ was added. The mixture was stirred at reflux for 24 hours under a nitrogen stream. Extract with dichloromethane and distilled water and filter the organic layer with silica gel. The organic solution was removed and silica gel column with nucleic acid: dichloromethane = 7: 3 (v / v) to recrystallize the product solid with dichloromethane and normal nucleic acid to give 12.86 g of a compound of formula A-10 (yield: 72%). .

(Manufacture of organic light emitting device)

Example 6

Specifically, the method of manufacturing the organic light emitting device, the anode is cut into a glass substrate having a sheet resistance value of 15 / cm ² of 50 mm X 50 mm X 0.7 mm in acetone, isopropyl alcohol and pure water Ultrasonic cleaning for each 15 minutes was followed by UV ozone cleaning for 30 minutes.

Using the prepared π 진공 transparent electrode as the anode, the following HTM compound was vacuum deposited on the ΙΤΌ substrate to form a hole injection layer having a thickness of 1200A.

[HTM]

The compound synthesized in Example 1 was used as a host, and a phosphorescent green dopant was doped with 7 wt% of the following PhGD compound to form a light emitting layer having a thickness of 300 A by vacuum evaporation. ΠΌ was used as a positive electrode with a thickness of 1000 A.

Aluminum (A1) was used at a thickness of 1000 A.

[PhGD]

Then, BAlq [Bis (2-methyl-8-quinolinolato-Nl, 08)-(U'-Biphenyl-4-olato) aluminum] 50 A and Alq3 [Tris (8-hydroxyquinolinato) aluminium] 250 A 1 sequentially stacked to form an electron transport layer. LiF5A and on the electron transport layer An organic light emitting diode was manufactured by sequentially vacuum depositing A11000A to form a cathode.

[BAlq] [Alq3]

Example 7

In the same manner as in Example 6 except for using the compound prepared in Example 2 instead of using the compound prepared in Example 1 as the emission layer.

The organic light emitting device was manufactured.

Example 8

Example instead of using the compound prepared in Example 1 as the light emitting layer

Except for using the compound prepared in 3 was the same as in Example 6

The organic light emitting device was manufactured.

Example 9

In the same manner as in Example 6 except for using the compound prepared in Example 4 instead of using the compound prepared in Example 1 as the emission layer.

The organic light emitting device was manufactured.

Example 10

In the same manner as in Example 6 except for using the compound prepared in Example 5 instead of using the compound prepared in Example 1 as the emission layer.

The organic light emitting device was manufactured.

Example ad-6

In the same manner as in Example 6 except for using the compound prepared in Example ad-1 instead of using the compound prepared in Example 1 as the emission layer.

The organic light emitting device was manufactured.

Example ad-7

In the same manner as in Example 6, except that the compound prepared in Example ad-2 was used instead of the compound prepared in Example 1 as the light emitting layer. The organic light emitting device was manufactured.

Example ad-8

In the same manner as in Example 6 except for using the compound prepared in Example ad-3 instead of using the compound prepared in Example 1 as a light emitting layer.

The organic light emitting device was manufactured.

Example ad-9

In the same manner as in Example 6 except for using the compound prepared in Example ad-4 instead of using the compound prepared in Example 1 as the emission layer.

The organic light emitting device was manufactured.

Example ad-10

In the same manner as in Example 6 except for using the compound prepared in Example ad-5 instead of using the compound prepared in Example 1 as the emission layer.

The organic light-emitting device was manufactured.

Comparative Example 1

Except for using the compound synthesized in Example 1 as a host of the light emitting layer, the same as in Example 6 except that 4,4-Ν, Ν-dicarbazole biphenyl (CBP) was used as the host of the light emitting layer An organic light emitting device was manufactured by the method.

(Performance Measurement of Organic Light Emitting Diode)

For each of the organic light emitting diodes manufactured in Examples 6 to 10, ad-6 to ad-10, and Comparative Example 1, current density change, luminance change, and luminous efficiency according to voltage were measured. Specific measurement methods are as follows, and the results are shown in Table 1 below.

(1) Measurement of change in current density according to voltage change

With respect to the organic light emitting device manufactured, the current value flowing through the unit device was measured using a current-voltmeter (Keithley2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.

(2) Measurement of luminance change according to voltage change

The resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000 A) while increasing the voltage from 0V to 10V to obtain a result.

(3) Measurement of luminous efficiency

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

TABLE 1

In the devices of Examples 6 to 10 and Examples ad-6 to ad-10, compared to Comparative Example 1 in which a comparative material CBP was used as a host of the light emitting layer, it was confirmed that the efficiency of the device was improved. The present invention is not limited thereto, but may be manufactured in various forms, and it is understood by those skilled in the art that the present invention may be implemented in other specific forms without changing the technical spirit or essential features of the present invention. Could be. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

Claims

Claims Claim 1 Compound for an organic optoelectronic device represented by the following formula (1):

[Formula 1]

In Chemical Formula 1

Ar ¹ is a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,

L is a substituted or unsubstituted C2 to C6 alkenylene group, a substituted or unsubstituted C2 to C6 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group or these Is a combination of

n is an integer of any one of 0 to 3,

X ¹ to X ⁸ are independently of each other, -N- or -CR'-, any one of X ¹ to X ⁸ is -N-,

R ¹ to R ¹⁰ and R ′ are each independently hydrogen, deuterium, halogen, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted Or an 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, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group , A substituted or unsubstituted C2 to C20 acylamino group, Substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20

Sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthi group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocycloti Groups, substituted or unsubstituted C1 to C20 ureide groups, substituted or unsubstituted C3 to C40 silyl groups, or a combination thereof.

[Claim 2]

The method of claim 1,

Ar ¹ is a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and in the range of Ar ¹ includes nitrogen except for a carbazolyl group The heteroaryl group is excluded compound for an organic optoelectronic device. ^'

[Claim 3]

In that U term,

Any one of X ¹ to X ⁸ is -N-, and X ⁴ is -N-

Compound for organic optoelectronic device.

[Claim 4]

The method of claim 1,

Any ^{one of} X ¹ to X ⁸ is —N—, wherein X ¹ and X ³ are -N-, or ² and X ⁴ are -Ν-.

[Claim 5]

The method of claim 4,

Wherein X ¹ and X ³ are -Ν-, and X ² is -C (Ph)-.

[Claim 6]

The method of claim 4,

Wherein X ² And X ⁴ Is -N-, X ³ Is -C (Ph)-Is a compound for an organic optoelectronic device.

[Claim 7]

The method of claim 1,

Any one of the X ¹ to X ⁴ is -N-, Any one of the X ⁵ to X ⁸ is -N- compound for an organic optoelectronic device.

[Claim 8]

According to claim 11,

Any one of the X ¹ to X ⁴ is -N-, Any two of the X ⁵ to X ⁸ is -N- compound for an organic optoelectronic device.

[Claim 9]

The method of claim 1,

Ar ¹ is a compound for an organic optoelectronic device is represented by the following formula S-1: [Formula s-1]

In Chemical Formula S-1,

Ar ² and Ar ³ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,

* Is the connection point.

[Claim 10]

According to claim 11,

Ar ¹ is a compound for an organic optoelectronic device is represented by the following formula S-2: [Formula s-2]

In Chemical Formula S-2,

X ⁹ is -NR'-, -0- or -S-,

R ¹¹ and R ¹² and R ′ independently of one another are hydrogen, deuterium, halogen, cyano, hydroxyl, amino, substituted or unsubstituted C1 to C20 amine, nitro, carboxyl, ferrocenyl, substituted Or an 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 C Aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 acyloxy group, Substituted or unsubstituted C2 to C20 acylamino group substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20

Sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 alkylthi group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocycloti Group, a substituted or unsubstituted C1 to C20 ureide group, a substituted or unsubstituted C3 to C40 silyl group, or a combination thereof,

* Is the connection point.

[Claim 11]

According to claim 11,

Ar ¹ is a compound for an organic optoelectronic device is represented by the following formula S-3: [Formula S-3]

In Chemical Formula S-3,

R ⁱⁱ and R ⁱ² are each independently hydrogen, deuterium, halogen, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1 to C20 amine group, nitro group, carboxyl group,

Ferrocenyl, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or Unsubstituted C6 to C20 aryloxy group, substituted or unsubstituted C3 to C40 silyloxy group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 To C20 acyloxy group, substituted or unsubstituted C2 to C20 acylamino group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20

Aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted C1 to C20 sulfonyl group, substituted or unsubstituted C1 to C20 Alkylthiol group, substituted or unsubstituted C6 to C20 arylthiol group, substituted or unsubstituted C1 to C20 heterocyclothiyl group, substituted or unsubstituted C1 to C20 ureide group, substituted or unsubstituted C3 to C40 silyl Groups or a combination thereof,

* Is the connection point.

[Claim 12]

According to claim 1,

Ar ¹ is a compound for an organic optoelectronic device is represented by the following formula S-4. [Formula S-4]

In Chemical Formula S-4,

* Is the connection point.

[Claim 13]

The method of claim 1,

Ar ¹ is a compound for an organic optoelectronic device is represented by the following formula S-5 or S-6.

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

In Chemical Formulas S-5 and S-6,

* Is the connection point.

[Claim 14]

At least one layer interposed between the positive electrode, the negative electrode and the positive electrode and the negative electrode In an organic light emitting device comprising an organic thin film layer,

At least one of the organic thin film layers according to claim 1

An organic light emitting device comprising a compound for an organic optoelectronic device.

[Claim 15]

The method of claim 14,

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

Organic light emitting device.

[Claim 16]

The method of claim 15,

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

[Claim 17]

The method of claim 16,

The organic light emitting device further comprises a dopant represented by the following formula D-1:

[Formula D-1]

In Chemical Formula D-1,

R ¹³ to R ²⁰ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C1 to C20 fluoroalkyl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted Or an unsubstituted C1 to C20 amino group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, or a substituted or unsubstituted silyl group, and two adjacent substituents form a fused ring which Can be.

[Claim 18]

A display device comprising the organic light emitting device of claim 14.