KR20180078177A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an adamantane derivative compound and an organic electroluminescent device comprising the same, and more particularly, to an adamantane derivative compound which can be used in an organic electroluminescent device and to the organic electroluminescent device having excellent properties such as low power and high efficiency by using the compound.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to an organic compound having a novel structure, and more particularly to an organic light emitting compound having excellent heat resistance which can be used as a light emitting layer, a hole injecting layer, a hole transporting layer or an electron blocking layer material layer of an organic electroluminescent device, BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device (OELD).

The organic electroluminescent device is simpler in structure than other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP), and a field emission display (FED) It is known that the viewing angle characteristics are excellent. In addition to this, it is used as a light source for a flat panel display such as a wall-hanging TV or a backlight of a display, a lighting, and a billboard because the response speed is fast and the driving voltage is low.

In order to improve the efficiency and stability of the organic electroluminescent device, a low-voltage-driven organic electroluminescent device in which a laminated organic thin film is formed between two opposite electrodes by CW Tang of Eastman Kodak Co. (CW Tang, SA Vanslyke, Applied Physics Letters, vol. 51, p. 913, 1987), research on organic materials for a multilayer thin film structure type organic electroluminescent device has been actively conducted.

Generally, an organic electroluminescent device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and at least one organic layer between the two electrodes. At this time, the organic electroluminescent device has a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) An electron blocking layer (EBL) or a hole blocking layer (HBL) are sequentially stacked in front of and behind the light emitting layer in order to increase the efficiency of the light emitting layer. .

As the material used in the organic electroluminescent device, a pure organic material or a complex in which an organic material and a metal form a complex are mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, And the like.

Wherein, as the hole injection material or the hole transporting material is easily oxidized, the organic material is generally used that has a stable state in its oxidized electrochemically. As the electron injecting material or the electron transporting material, an organic material which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. As the light emitting layer material, a material having a stable form in both oxidation and reduction states is preferable, and a material having high luminous efficiency for converting excitons into light when the exciton is formed is preferable.

In addition, the material used in the organic electroluminescent device preferably has the following properties.

First, materials used in organic electroluminescent devices must have a high glass transition temperature (Tg). Local heat generation of the device by joule heating during driving causes a change in the characteristics of the device. In addition, the OLED device after the deposition process is subjected to a heat treatment process of 100 to 120 degrees, in which a crystallization phenomenon occurs in a material having a low glass transition temperature. TPD or NPB, which is a conventionally used hole transport material, has a low glass transition temperature (Tg) of 60 and 96, respectively, so that the above phenomenon occurs during driving or after the process. This crystallization phenomenon breaks the charge balance, .

Second, the organic materials used should be absorptive in the visible region. In particular, it should be absorptive at 450 nm or more, but light absorption causes absorption of generated light in the light emitting layer, thereby decreasing the luminous efficiency.

Thirdly, the organic materials used require a very high level of deposition thermal stability. Generally, in the process of making OLED panels, organic materials are used for one week or more (144 hours) for one week filling. The amount of organic substances to be packed decreases with time, but the deposition rate must be kept constant, thereby increasing the deposition temperature. At this time, if the organic material is decomposed to cause a problem in the device performance, the glass transition temperature can not be used even if the glass transition temperature is high and there is no absorption in the visible light region.

Therefore, there is a continuing need for the development of new materials suitable for mass production having the above-mentioned excellent thermal and electro-optical characteristics, high efficiency and long life.

Japanese Patent No. 4649752, Japanese Patent No. 4470508, Japanese Patent No. 5551369 and Korean Patent Publication No. 2008-0104996

An object of the present invention is to provide a novel organic compound excellent in crystallinity, heat resistance and thermal stability.

Another object of the present invention is to provide an organic electroluminescent device having a low driving voltage and excellent luminous efficiency, external quantum efficiency (EQE) and thermal stability using the organic compound.

The present invention provides an organic compound represented by the following general formula (1) and an organic electroluminescent device including the same.

[Chemical Formula 1]

In this formula,

X is selected from the group consisting of N (R ₃ ), S, O, and Si (R ₄ ) (R ₅ )

n and m are the same or different and each independently represents an integer of 0 to 4,

, 수소, 중수소, 치환 또는 비치환의 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 3 내지 40의 시클로알킬기, 치환 또는 비치환의 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환의 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환의 탄소수 2 내지 30의 헤테로알킬기, 치환 또는 비치환의 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴기, 치환 또는 비치환의 탄소수 2 내지 30의 헤테로아릴기, 및 치환 또는 비치환의 탄소수 3 내지 30의 헤테로아릴알킬기로 이루어진 군으로부터 선택되고(a 및 b 는 0 내지 1의 정수이고), R₄와 R₅는 서로 연결되어 포화 또는 불포화 고리를 형성할 수 있으며,R ₁ to R ₅ are the same as or different from each other, and each independently represents -L ₁ - (A) _a ,

, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C40 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2- Substituted or unsubstituted C2-C30 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl And a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms (a and b are an integer of 0 to 1), R ₄ and R ₅ are connected to each other to form a saturated or unsaturated ring And,

L ₁ and L _{2 each} represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 nuclear atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, A substituted or unsubstituted C2-C10 alkenylene group, a substituted or unsubstituted C2-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heteroalkylene group, a substituted or unsubstituted C2-C10 cycloalkylene group, A substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C2-C10 heteroalkenylene group, and a substituted or unsubstituted C2-C10 heterocycloalkenylene group,

Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms , A substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C1 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C20 alkenyl group, A substituted or unsubstituted C1-C20 cycloalkenyl group, and a substituted or unsubstituted C1-C20 heteroalkenyl group,

The substituents of R ₁ to R ₅ , A, L ₁ and L ₂ , Ar ₁ and Ar ₂ are each independently selected from the group consisting of deuterium, cyano group, nitro group, halogen group, hydroxyl group, alkyl group having 1 to 30 carbon atoms, An alkyl group having 2 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, An aryl group, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, A heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

The organic compound according to the present invention has a low crystallinity and is excellent in heat resistance and chemical stability and can be used as an organic compound in a hole injecting layer, a hole transporting layer, a light emitting layer, a hole blocking layer, an electron transporting layer and / The electroluminescent device is excellent in lifetime characteristics, light emitting efficiency, external quantum efficiency (EQE) and thermal stability, and has a low driving voltage.

The present invention is capable of various modifications and various embodiments, and it is intended to illustrate and explain the specific embodiments in detail. It should be understood, however, that the present invention is not intended to be limited to any particular embodiment, but is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the present invention.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In the specification of the present invention, terms such as "comprises" or "having" are intended to designate the presence of stated features, integers, steps, operations, elements, parts or combinations thereof, But do not preclude the presence or addition of other features, numbers, steps, operations, components, parts, or combinations thereof.

As used herein, the term " combination thereof " means that two or more substituents are bonded to each other through a single bond or a linking group, or two or more substituents are condensed and connected.

 "Alkenyl" in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

The term "alkynyl" in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, dimethylfluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and may be a linear, branched or cyclic structure . ≪ / RTI > Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon of the ring, preferably 1 to 3 carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

"Alkylsilyl" in the present invention refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

Hereinafter, the present invention will be described.

The present invention provides an organic compound represented by the following general formula (1) and an organic electroluminescent device including the same.

[Chemical Formula 1]

In this formula,

X is selected from the group consisting of N (R ₃ ), S, O, and Si (R ₄ ) (R ₅ )

n and m are the same or different and each independently represents an integer of 0 to 4,

, 수소, 중수소, 치환 또는 비치환의 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 3 내지 40의 시클로알킬기, 치환 또는 비치환의 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환의 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환의 탄소수 2 내지 30의 헤테로알킬기, 치환 또는 비치환의 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴기, 치환 또는 비치환의 탄소수 2 내지 30의 헤테로아릴기, 및 치환 또는 비치환의 탄소수 3 내지 30의 헤테로아릴알킬기로 이루어진 군으로부터 선택되고(a 및 b 는 0 내지 1의 정수이고), R₄와 R₅는 서로 연결되어 포화 또는 불포화 고리를 형성할 수 있으며,R ₁ to R ₅ are the same as or different from each other, and each independently represents -L ₁ - (A) _a ,

, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C40 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2- Substituted or unsubstituted C2-C30 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl And a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms (a and b are an integer of 0 to 1), R ₄ and R ₅ are connected to each other to form a saturated or unsaturated ring And,

L ₁ and L _{2 each} represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 nuclear atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, A substituted or unsubstituted C2-C10 alkenylene group, a substituted or unsubstituted C2-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heteroalkylene group, a substituted or unsubstituted C2-C10 cycloalkylene group, A substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C2-C10 heteroalkenylene group, and a substituted or unsubstituted C2-C10 heterocycloalkenylene group,

Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms , A substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C1 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C20 alkenyl group, A substituted or unsubstituted C1-C20 cycloalkenyl group, and a substituted or unsubstituted C1-C20 heteroalkenyl group,

The substituents of R ₁ to R ₅ , A, L ₁ and L ₂ , Ar ₁ and Ar ₂ are each independently selected from the group consisting of deuterium, cyano group, nitro group, halogen group, hydroxyl group, alkyl group having 1 to 30 carbon atoms, An alkyl group having 2 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, An aryl group, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, A heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

The compound of Formula 1 is an adamantane derivative compound having at least one adamantyl group (A) and a trisubstituted amino group. The compound of Formula 1 has characteristics of hole injection, hole transport, low crystallinity and high heat resistance.

The adamantyl group (A) forms a condensed ring in three dimensions to lower the mobility of the compound of Formula 1 to minimize energy loss due to the molecular motion of the compound of Formula 1 and to have high heat resistance characteristics. In addition, since the compound of Formula 1 has a high melting point and a glass transition temperature due to a parent structure having a high molecular weight and a discrete electronic structure, the stability of the thin film of the organic electroluminescent device using the compound of Formula 1 is improved.

Specifically, the compound represented by the formula (1) is as follows:

[Chemical Formula 1]

In this formula,

X is selected from the group consisting of N (R ₃ ), S, O and Si (R ₄ ) (R ₅ ), n and m are the same or different and independently of each other an integer of 0 to 4.

, 수소, 중수소, 치환 또는 비치환의 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 3 내지 40의 시클로알킬기, 치환 또는 비치환의 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환의 탄소수 2 내지 24의 알키닐기, 치환 또는 비치환의 탄소수 2 내지 30의 헤테로알킬기, 치환 또는 비치환의 탄소수 7 내지 30의 아르알킬기, 치환 또는 비치환의 탄소수 6 내지 30의 아릴기, 치환 또는 비치환의 탄소수 2 내지 30의 헤테로아릴기, 및 치환 또는 비치환의 탄소수 3 내지 30의 헤테로아릴알킬기로 이루어진 군으로부터 선택되고(a 및 b 는 0 내지 1의 정수이고), R₄와 R₅는 서로 연결되어 포화 또는 불포화 고리를 형성할 수 있다. R ₁ to R ₅ are the same as or different from each other, and each independently represents -L ₁ - (A) _a ,

, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C40 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2- Substituted or unsubstituted C2-C30 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl And a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms (a and b are an integer of 0 to 1), R ₄ and R ₅ are connected to each other to form a saturated or unsaturated ring .

 A is a substituted or unsubstituted adamantyl group.

a and b are the same as or different from each other, and each independently is an integer of 0 to 1, and a + b? 1. Preferably, A may be a compound represented by the following formula 2 or 3:

(2)

(3)

When X is Si (R ₄ ) (R ₅ ), R ₄ and R ₅ may be connected to each other to form a saturated or unsaturated ring. For example, R ₄ and R ₅ may be connected to each other to form a substituted or unsubstituted C3- A ring selected from the group consisting of a substituted or unsubstituted C 1 -C 20 cycloalkyl group, a substituted or unsubstituted C 1 -C 20 heterocycloalkyl group, a substituted or unsubstituted C 1 -C 20 cycloalkenyl group and a substituted or unsubstituted C 1 -C 20 heteroalkenyl group is referred to as L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 nucleus atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, A cycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group having 2 to 10 carbon atoms A substituted or unsubstituted C2-C10 heteroalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C2-C10 heteroalkenylene group, and a substituted or unsubstituted C2- And a heterocycloalkenylene group.

Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms , A substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C1 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C20 alkenyl group, A substituted or unsubstituted cycloalkenyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms.

The substituents of R ₁ to R ₅ , A, L ₁ and L ₂ , Ar ₁ and Ar ₂ are each independently selected from the group consisting of deuterium, cyano group, nitro group, halogen group, hydroxyl group, alkyl group having 1 to 30 carbon atoms, An alkyl group having 2 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, An aryl group, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, A cycloalkyl group having 1 to 30 carbon atoms, a heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 4 below.

[Chemical Formula 4]

Wherein R ₁ , R ₂ , R ₄ and R _{5, which} may be the same or different, are each independently a substituted or unsubstituted adamantyl group, n and m are each independently an integer of 0 to 2, -L ₁ - _{(a) a,} from hydrogen, heavy hydrogen, substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted C2 to 30 of the ring of the alkenyl group, a substituted A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C2 to C30 heteroalkyl group, a substituted or unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, And a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms (a and b are integers of 0 to 1), R ₄ and R ₅ are connected to each other Be It may form a saturated or unsaturated ring.

According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 5 below.

[Chemical Formula 5]

Wherein A is a substituted or unsubstituted adamantyl group, X is selected from the group consisting of N (R ₃ ), S, O and Si (R ₄ ) (R ₅ ), m is an integer from 0 to 2 and, R _1, R _3, R ₄ and R ₅ are the same or different, each independently -L1- (a) a, group of hydrogen, heavy hydrogen, substituted or unsubstituted, having 1 to 30 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or unsubstituted C2-C30 heteroalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms. (A and b are 0 to 1 An integer), the R ₄ and R ₅ are connected to each other to form a saturated or unsaturated ring.

The compound represented by the formula (1) according to the present invention may be any one of the following compounds 1 to 460.

Another embodiment of the present invention provides an organic electroluminescent device comprising the compound of formula (1).

The organic electroluminescent device includes a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein the at least one organic layer includes the compound of Formula 1.

The organic material layer includes at least one layer such as a hole injection layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer.

The organic material layer may include a hole injection layer, a hole transporting layer, and / or an electron blocking layer. At least one layer of the organic material layer may include at least one compound of the above formula (1).

The organic layer may include a light emitting layer, and the light emitting layer may include one or more compounds of Formula 1. At this time, the compound of Chemical Formula 1 has a glass transition temperature of 100 or more and has a very high thermal stability.

The organic material layer may include one or more compounds selected from the compounds represented by the general formula (1), preferably the compounds represented by the general formulas (1) to (460), alone or in combination.

Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by the above formula have.

The organic material layer may be formed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film formation method such as spin coating, immersion coating, or flow coating. If the film thickness is too large, a high applied voltage is required to obtain a constant light output, which leads to deterioration of efficiency. When the film thickness is too thin, pin holes are generated and an electric field is applied A sufficient light emission luminance can not be obtained. A typical film thickness is preferably in the range of 5 nm to 10 mu m, more preferably in the range of 50 nm to 400 nm.

Hereinafter, the present invention will be described in more detail with reference to Examples. These embodiments are only for describing the present invention more specifically, and the scope of the present invention is not limited by these examples.

Synthetic example  1: Preparation of Compound 300

54.1 g (0.15 mol) of 4- (adamantan-1-yl) phenyltrifluoromethanesulfonate and 28.1 g (0.18 mol) of (4-chlorophenyl) boronic acid were dissolved in 800 ml of toluene, 62.2 g (0.45 mol) of potassium carbonate and 5.2 g (4.5 mmol) of tetrakis (triphenylphosphine) palladium (0) were added and refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, and organic layer was extracted with 500 ml of dichloromethane and 300 ml of H ₂ O. [ The organic layer was dried over MgSO ₄ , and the filtrate was distilled. The residue was subjected to column chromatography using dichloromethane and then recrystallized with n-hexane / dichloromethane to obtain 1- (4'-chloro- [1,1'-biphenyl] ) Adamantane (41.2 g) was obtained in a yield of 85%.

A mixture of 5.63 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, (Biphenyl) -4-yl) adamantane were dissolved in 100 ml of toluene, and then 4.32 g (45.0 mmol) of sodium tert-butoxide, 2-dicyclohexylphosphino- 246 mg (0.60 mmol) of dimethoxybiphenyl and 275 mg (0.30 mmol) of tris (dibenzylideneacetone) dipalladium (0) were added and refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, and organic layer was extracted with 100 ml of dichloromethane and 50 ml of H ₂ O. [ The organic layer was dried over MgSO ₄ , and the filtrate was distilled and then subjected to column chromatography using n-hexane / dichloromethane to obtain Compound 300 in a yield of 59%.

Synthetic example  2: Preparation of compound 429

A mixture of 5.63 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, -Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 429 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  3: Preparation of compound 340

(15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, -Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 340 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  4: Preparation of compound 430

A mixture of 6.76 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) '-Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 430 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  5: Preparation of compound 158

A mixture of 6.76 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) -9- '-Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 158 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  6: Preparation of compound 431

A mixture of 5.87 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, '-Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 431 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  7: Preparation of compound 436

A mixture of 5.87 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, '-Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 436 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  8: Preparation of compound 285

(15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) dibenzo [b, Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 285 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  9: Preparation of compound 325

(15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) dibenzo [b, Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 325 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  10: Preparation of compound 432

(15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) dibenzo [b, Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 432 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  11: Preparation of compound 433

(15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) -9-phenyl-9H- -Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 433 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  12: Preparation of compound 151

(15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) -9-phenyl-9H- -Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 151 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  13: Preparation of compound 400

(15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) dibenzo [b, d] thiophen- -Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 400 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  14: Preparation of compound 421

(1, 1 ' -chloro-[l, l '] biphenyl- -Biphenyl] -4-yl) adamantane was used in place of the compound obtained in Synthesis Example 1. Compound 421 was prepared in the same manner as in Synthesis Example 1, except that 5.33 g (16.5 mmol)

Synthetic example  15: Preparation of compound 320

A mixture of 5.63 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, Compound 320 was prepared in the same manner as in Synthesis Example 1, except that 6.58 g (16.5 mmol) of 4 ', 4', 1 "-tetraphenyl] -4-yl) adamantane was used.

Synthetic example  16: Preparation of compound 453

(15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, d] thiophen- Compound 453 was prepared in the same manner as in Synthesis Example 1, except that 6.58 g (16.5 mmol) of 1 ': 4', 1 "-terphelyl] -4-yl) adamantane was used.

Synthetic example  17: Preparation of compound 305

(4 '' - chloro-l, l '] furan-3-amine and 5.03 g (15.0 mmol) of N - [(1,1'- : 4 ', 1 "-terphelyl] -4-yl) adamantane was used in place of the compound (305).

Synthetic example  18: Preparation of compound 410

A mixture of 5.27 g (15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) dibenzo [b, Compound 410 was prepared in the same manner as in Synthesis Example 1, except that 6.58 g (16.5 mmol) of 4 ', 4', 1 "-terpetyl] -4-yl) adamantane was used.

Synthetic example  19: Preparation of compound 445

A mixture of 6.76 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) Compound 445 was prepared in the same manner as in Synthesis Example 1 except that 6.58 g (16.5 mmol) of 1 ': 4', 1 "-terphelyl] -4-yl) adamantane was used.

Synthetic example  20: Preparation of compound 446

To a solution of 6.16 g (15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) -9- Compound 446 was prepared in the same manner as in Synthesis Example 1, except for using 6.58 g (16.5 mmol) of 4 ', 4', 1 "-tetraphenyl] -4-yl) adamantane.

Synthetic example  21: Preparation of compound 447

A mixture of 6.76 g (15.0 mmol) of N- (9,9-dimethyl-9H-fluoren-2-yl) Compound 447 was prepared in the same manner as in Synthesis Example 1 except that 6.58 g (16.5 mmol) of 1 ': 4', 1 "-terphelyl] -4-yl) adamantane was used.

Synthetic example  22: Preparation of compound 448

To a solution of 6.16 g (15.0 mmol) of N - ([1,1'-biphenyl] -4-yl) -9- Compound 448 was prepared in the same manner as in Synthesis Example 1, except that 6.58 g (16.5 mmol) of 4 ', 4', 1 "-terphelyl] -4-yl) adamantane was used.

Synthetic example  23: Preparation of compound 233

(15.0 mmol) of N - ([1,1 ': 4', 1 "-terphenyl] -4-yl) dibenzo [b, 1-yl) phenyl trifluoromethanesulfonate (5.95 g, 16.5 mmol) was used in place of the compound obtained in Synthesis Example 1. Compound 233 was prepared in the same manner as in Synthesis Example 1, except that 5.95 g

Synthetic example  24: Preparation of compound 454

(15.0 mmol) of N - ([1,1 ': 4', 1 "-terphenyl] -4-yl) dibenzo [b, -1-yl) phenyltrifluoromethanesulfonate (5.95 g, 16.5 mmol) was used in place of the compound obtained in Synthesis Example 1. Compound 454 was prepared in the same manner as in Synthesis Example 1, except that 5.95 g

Synthetic example  25: Preparation of compound 455

A mixture of 7.30 g (15.0 mmol) of N - ([1,1 ': 4', 1 "-terphenyl] -4- -1-yl) phenyltrifluoromethanesulfonate (5.95 g, 16.5 mmol) was used in place of the compound obtained in Synthesis Example 1. Compound 455 was prepared in the same manner as in Synthesis Example 1.

Synthetic example  26: Preparation of compound 456

A solution of 7.30 g (15.0 mmol) of N - ([1,1 ': 4', 1 "-terphenyl] -4- -1-yl) phenyltrifluoromethanesulfonate (5.95 g, 16.5 mmol) was used in place of the compound obtained in Synthesis Example 1. Compound 456 was prepared in the same manner as in Synthesis Example 1,

Synthetic example  27: Preparation of compound 457

A mixture of 7.49 g (15.0 mmol) of N- (9,9-diphenyl-9H-fluoren-2-yl) dibenzo [b, Compound 457 was prepared in the same manner as in Synthesis Example 1, except that 5.95 g (16.5 mmol) of trifluoromethanesulfonate was used.

Synthetic example  28: Preparation of compound 460

A mixture of 7.74 g (15.0 mmol) of N- (9,9-diphenyl-9H-fluoren-2-yl) dibenzo [b, d] thiophen- Compound 460 was prepared in the same manner as in Synthesis Example 1, except that 5.95 g (16.5 mmol) of phenyltrifluoromethanesulfonate was used.

Synthetic example  29: Preparation of compound 458

(15.0 mmol) of N- (9,9-diphenyl-9H-fluoren-2-yl) -9- Compound 458 was prepared in the same manner as in Synthesis Example 1, except that 5.95 g (16.5 mmol) of phenyltrifluoromethanesulfonate was used.

Synthetic example  30: Preparation of compound 459

A solution of 8.62 g (15.0 mmol) of N- (9,9-diphenyl-9H-fluoren-2-yl) Compound 459 was prepared in the same manner as in Synthesis Example 1, except that 5.95 g (16.5 mmol) of phenyltrifluoromethanesulfonate was used.

Mass and yield data of the synthesized compounds are shown in Table 1 below.

compound Mass [M + H] < Yield (%) compound Mass [M + H] < Yield (%) Synthesis Example 1
(Compound 300) 662.3 60 Synthesis Example 16
(Compound 453) 754.3 63 Synthesis Example 2
(Compound 429) 662.3 65 Synthesis Example 17
(Compound 305) 698.3 61 Synthesis Example 3
(Compound 340) 662.3 63 Synthesis Example 18
(Compound 410) 714.3 60 Synthesis Example 4
(Compound 430) 737.4 57 Synthesis Example 19
(Compound 445) 813.4 56 Synthesis Example 5
(Compound 158) 737.4 55 Synthesis Example 20
(Compound 446) 773.4 59 Synthesis Example 6
(Compound 431) 678.3 50 Synthesis Example 21
(Compound 447) 813.4 60 Synthesis Example 7
(Compound 436) 678.3 51 Synthesis Example 22
(Compound 448) 773.4 62 Synthesis Example 8
(Compound 285) 622.3 52 Synthesis Example 23
(Compound 233) 622.3 48 Synthesis Example 9
(Compound 325) 622.3 58 Synthesis Example 24
(Compound 454) 638.3 45 Synthesis Example 10
(Compound 432) 622.3 55 Synthesis Example 25
(Compound 455) 697.4 55 Synthesis Example 11
(Compound 433) 697.4 60 Synthesis Example 26
(Compound 456) 697.4 51 Synthesis Example 12
(Compound 151) 697.4 59 Synthesis Example 27
(Compound 457) 710.3 48 Synthesis Example 13
(Compound 400) 638.3 48 Synthesis Example 28
(Compound 460) 726.3 45 Synthesis Example 14
(Compound 421) 638.3 50 Synthesis Example 29
(Compound 458) 785.4 60 Synthesis Example 15
(Compound 320) 738.4 62 Synthesis Example 30
(Compound 459) 785.4 62

Example  One: Synthetic example  1 (Compound 300) Hole transport layer  Used as a material The organic electroluminescent device  Produce

A substrate on which an Ag alloy as a light-reflecting layer and ITO (10 nm) as an anode of an organic light emitting device were sequentially laminated was patterned into a cathode, an anode region and an insulating layer through a photo-lithograph process, The surface of the anode (ITO) was surface-treated with O2: N2 plasma for the purpose of work-function increase and descum. Hexahazatriphenylene-hexacarbonitrile (HAT-CN) having a thickness of 100 Å was formed thereon as a hole injection layer (HIL). Subsequently, Synthesis Example 1 (Compound 300) was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 1000 Å. Phenyl] -N- (4- (spiro [benzo [de] anthracene-7,9'-fluorene] -2'-yl) phenyl) diester as an electron blocking layer (EBL) on the hole transport layer Benzo [b, d] furan-4-amine ( hereinafter referred to as Compound D ) was formed to a thickness of 150 Å and a blue EML was formed on the electron blocking layer (EBL) N1, N6, N6-tetrakis (4- (1-silyl) phenyl) pyrene-1,6-diamine was doped with a dopant while depositing? -ADN to form a light emitting layer with a thickness of 200 占.

Phenyl] -1-phenyl-1H-benzo [d] imidazole and LiQ in a weight ratio of 1: 1 The electron transport layer (ETL) was deposited to a thickness of 360 Å by mixing. Magnesium (Mg) and silver (Ag) were deposited as a cathode at a ratio of 9: 1 to a thickness of 160 Å. N4'-diphenyl-N4, N4'-bis (4- (9-phenyl-9H-carbazol-3- yl) phenyl) - [1,1'- 4,4'-diamine was deposited to a thickness of 63 to 65 nm. A seal cap was attached to the capping layer (CPL) with a UV curable adhesive to protect the organic electroluminescent device from O ₂ or moisture in the air, thereby manufacturing an organic electroluminescent device.

Comparative Example  One

Example 1 Synthesis of a hole transport layer in Example 1 (compound 300) Instead of NPB (N4, N4, N4 ' , N4'- tetra ([1,1'-biphenyl] -4-yl) - [1,1' -Biphenyl] -4,4'-diamine) was used as the organic electroluminescent device.

Comparative Example  2 to 3

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compound A or Compound B shown below was used instead of Synthesis Example 1 (Compound 300) as the hole transport layer in Example 1 .

[Compound A]

[Compound B]

Comparative Example  4 to 6

In Example 1, an electron blocking layer (EBL) was prepared in the same manner as in Example 1, except that N-phenyl-N- (4- (spiro [benzodioxanthracene-7,9'-fluorene] , d] furan-4-amine ( hereinafter referred to as compound D ) An organic electroluminescent device was prepared in the same manner as in Example 1, except that the following Compound A, Compound B or Compound C was used, respectively.

[Compound A]

[Compound B]

[Compound C]

Example  2 to 19

 An organic electroluminescent device was prepared in the same manner as in Example 1, except that Synthesis Examples 2 to 7, 11 to 12, 19 to 22 and 25 to 30 were used instead of Synthesis Example 1 (Compound 300) as the hole transport layer in Example 1 .

Example  20 to 30

Except that NPB was used instead of Synthesis Example 1 (Compound 300) as the hole transport layer in Example 1, and Synthesis Examples 8 to 10, 13 to 18, and 23 to 24 were used as the electron blocking layer (EBL) An organic electroluminescent device was prepared.

Experimental Example : Organic field  Characterization of light emitting device

The table below the voltage, current efficiency, and lifetime characteristics of the above Comparative Examples 1 to 6 and Example 1, all-optical characteristics at a current of 10mA / cm ² by using the organic electroluminescent element prepared in to 30 and 20mA / cm ^{2 2} Respectively.

division
compound
Driving voltage
Luminance
efficiency
Color coordinates
life span
HTL
EBL
Volt
Cd / m ²
Cd / A
lm / W
CIEx
CIEy
T @ 95%
Comparative Example 1
NPB
Compound D
4.1
392
3.92
3.0
0.136
0.061
75
Comparative Example 2
Compound A
Compound D
4.3
402
4.02
2.9
0.137
0.060
85
Comparative Example 3
Compound B
Compound D
4.2
411
4.11
3.1
0.136
0.059
80
Comparative Example 4
NPB
Compound A
4.1
399
3.99
3.1
0.136
0.060
75
Comparative Example 5
NPB
Compound B
4.3
405
4.05
3.0
0.136
0.062
85
Comparative Example 6
NPB
Compound C
4.1
410
4.10
3.1
0.136
0.061
80
Example 1
Synthesis Example 1
(Compound 300)
Compound D
4.3
541
5.41
4.0
0.136
0.053
120
Example 2
Synthesis Example 2
(Compound 429)
4.2
510
5.10
3.8
0.134
0.057
115
Example 3
Synthesis Example 3
(Compound 340)
4.1
479
4.79
3.7
0.135
0.056
90
Example 4
Synthesis Example 4
(Compound 430)
3.9
540
5.40
4.3
0.137
0.051
110
Example 5
Synthesis Example 5
(Compound 158)
3.8
529
5.29
4.4
0.135
0.056
115
Example 6
Synthesis Example 6
(Compound 431)
4.1
480
4.80
3.7
0.135
0.056
90
Example 7
Synthesis Example 7
(Compound 436)
3.9
535
5.35
4.3
0.137
0.051
118
Example 8
Synthesis Example 11
(Compound 433)
3.8
559
5.59
4.6
0.135
0.056
120
Example 9
Synthesis Example 12
(Compound 151)
4.0
530
5.30
4.2
0.135
0.055
119
Example 10
Synthesis Example 19
(Compound 445)
3.9
456
4.56
3.7
0.136
0.056
130
Example 11
Synthesis Example 20
(Compound 446)
4.0
496
4.96
3.9
0.135
0.056
115
Example 12
Synthesis Example 21
(Compound 447)
3.9
423
4.23
3.4
0.136
0.056
135
Example 13
Synthesis Example 22
(Compound 448)
4.1
483
4.83
3.7
0.136
0.056
124
Example 14
Synthesis Example 25
(Compound 455)
3.9
559
5.59
4.5
0.135
0.057
128
Example 15
Synthesis Example 26
(Compound 456)
4.0
520
5.20
4.1
0.135
0.056
115
Example 16
Synthesis Example 27
(Compound 457)
4.0
510
5.10
4.0
0.135
0.057
118
Example 17
Synthesis Example 28
(Compound 460)
3.8
559
5.59
4.6
0.135
0.056
121
Example 18
Synthesis Example 29
(Compound 458)
3.8
555
5.55
4.6
0.134
0.056
128
Example 19
Synthesis Example 30
(Compound 459)
4.0
527
5.27
4.1
0.135
0.056
120
Example 20
NPB
Synthesis Example 8
(Compound 285)
4.0
420
4.20
3.3
0.135
0.055
90
Example 21
Synthesis Example 9
(Compound 325)
3.9
456
4.56
3.7
0.134
0.057
110
Example 22
Synthesis Example 10
(Compound 432)
3.9
477
4.77
3.8
0.137
0.051
95
Example 23
Synthesis Example 13
(Compound 400)
4.0
468
4.68
3.7
0.134
0.057
90
Example 24
Synthesis Example 14
(Compound 421)
3.8
480
4.80
4.0
0.136
0.053
95
Example 25
Synthesis Example 15
(Compound 320)
3.9
469
4.69
3.8
0.139
0.052
95
Example 26
Synthesis Example 16
(Compound 453)
4.2
430
4.30
3.2
0.134
0.057
100
Example 27
Synthesis Example 17
(Compound 305)
4.1
460
4.60
3.5
0.136
0.054
110
Example 28
Synthesis Example 18
(Compound 410)
3.9
480
4.80
3.9
0.135
0.055
105
Example 29
Synthesis Example 23
(Compound 233)
3.8
479
4.79
4.0
0.131
0.064
95
Example 30
Synthesis Example 24
(Compound 454)
3.9
459
4.59
3.7
0.134
0.057
98

It can be seen from Table 2 that when the compound according to the present invention is used as a hole transporting layer or an electron blocking layer material, the same or superior characteristics are exhibited in most device characteristics such as voltage, current efficiency and lifetime .

The following Table 3 shows the evaluation of the thermal characteristics of the organic compound used in the organic electroluminescent device, and it is confirmed that the organic compound according to the present invention has a high glass transition temperature (Tg) and a decomposition temperature (Td) .

compound rescue Tg (占 폚) Td (占 폚) Example 1 Synthesis Example 1
(Compound 300)

141 402 Example 8 Synthesis Example 11
(Compound 433)

130 385 Example 10 Synthesis Example 19
(Compound 445)

142 405 Example 17 Synthesis Example 28
(Compound 460)

129 390 Example 21 Synthesis Example 9
(Compound 325)

135 388 Comparative Example 2 Compound A

92 330 Comparative Example 3 Compound B

98 334 Comparative Example 6 Compound C

90 328

According to the results of Table 3, the glass transition temperature (Tg) and decomposition temperature (Td) of Compound A used in Comparative Example 2 were measured at 92 ° C and 330 ° C, Was measured at 98 占 폚 and 334 占 폚, and Tg and Td of the compound C used in Comparative Example 6 were measured at 90 占 폚 and 328 占 폚.

In the case of the compound 433, the glass transition temperature (Tg) was 130 ° C and the decomposition temperature (Td) was 385 ° C, which was 38 ° C and 55 ° C higher than that of the compound A, (Tg) of 141 ° C and a decomposition temperature (Td) of 402 ° C, respectively. Compounds 325 had a glass transition temperature (Tg) of 135 ° C and a decomposition temperature (Td) of 388 ° C, C, respectively.

In order to test the heat resistance of the organic electroluminescent device, the devices fabricated in Examples and Comparative Examples were allowed to stand at 110 DEG C for 1 hour, and the thermal characteristics of the device were measured, and the results are shown in Tables 4 and 5.

Before heat treatment division compound Driving voltage efficiency Color coordinates HTL EBL Volt Cd / A lm / W CIEx CIEy Comparative Example 1 NPB Compound D 4.1 3.92 3.0 0.136 0.061 Comparative Example 2 Compound A Compound D 4.3 4.02 2.9 0.137 0.060 Comparative Example 3 Compound B Compound D 4.2 4.11 3.1 0.136 0.059 Comparative Example 4 NPB Compound A 4.1 3.99 3.1 0.136 0.060 Example 8 Synthesis Example 11
(Compound 433) Compound D 3.8 5.59 4.6 0.135 0.056 Example 17 Synthesis Example 28
(Compound 460) Compound D 3.8 5.59 4.6 0.135 0.056 Example 21 NPB Synthesis Example 9
(Compound 325) 3.9 4.56 3.7 0.134 0.057

After heat treatment division compound Driving voltage efficiency Color coordinates HTL EBL Volt Cd / A lm / W CIEx CIEy Comparative Example 1 NPB Compound D 5.2 1.2 0.7 0.152 0.162 Comparative Example 2 Compound A Compound D 5.5 0.8 0.5 0.150 0.156 Comparative Example 3 Compound B Compound D 5.9 0.5 0.3 0.156 0.161 Comparative Example 4 NPB Compound A 5.6 0.6 0.3 0.154 0.158 Example 8 Synthesis Example 11
(Compound 433) Compound D 3.8 5.6 4.6 0.135 0.056 Example 17 Synthesis Example 28
(Compound 460) Compound D 3.8 5.59 4.6 0.135 0.058 Example 21 NPB Synthesis Example 9
(Compound 325) 3.9 4.58 3.7 0.134 0.058

Referring to Tables 4 and 5, it can be seen that the efficiency (current efficiency, luminous efficiency) of the organic electroluminescent devices of Comparative Examples 1 to 6 was about 60 to 90% or more after the heat treatment. On the contrary, before and after the heat treatment of the device using the compound of the present invention, the characteristics of the same level were maintained due to excellent thermal characteristics.

The organic electroluminescent device using the compound of Formula 1 according to the present invention as a hole transporting material and an electron blocking material has excellent characteristics such as a driving voltage, a luminous efficiency and a thermal stability.

Claims (14)

A compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
X is selected from the group consisting of N (R ₃ ), S, O, and Si (R ₄ ) (R ₅ )
n and m are the same or different and each independently represents an integer of 0 to 4,
R ₁ to R ₅ are the same as or different from each other, and each independently represents -L ₁ - (A) _a ,

, A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C40 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2- Substituted or unsubstituted C2-C30 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl And a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms (a and b are an integer of 0 to 1), R ₄ and R ₅ are connected to each other to form a saturated or unsaturated ring And,
L ₁ and L _{2 each} represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 nuclear atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, A substituted or unsubstituted C2-C10 alkenylene group, a substituted or unsubstituted C2-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heteroalkylene group, a substituted or unsubstituted C2-C10 cycloalkylene group, A substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C2-C10 heteroalkenylene group, and a substituted or unsubstituted C2-C10 heterocycloalkenylene group,
Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms , A substituted or unsubstituted C1 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C1 to C20 heterocycloalkyl group, a substituted or unsubstituted C1 to C20 alkenyl group, A substituted or unsubstituted C1-C20 cycloalkenyl group, and a substituted or unsubstituted C1-C20 heteroalkenyl group,
The substituents of R ₁ to R ₅ , A, L ₁ and L ₂ , Ar ₁ and Ar ₂ are each independently selected from the group consisting of deuterium, cyano group, nitro group, halogen group, hydroxyl group, alkyl group having 1 to 30 carbon atoms, An alkyl group having 2 to 30 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, An aryl group, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, A heteroarylamino group, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms. The method according to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 4:
[Chemical Formula 4]

Wherein A is a substituted or unsubstituted adamantyl group,
n and m are each independently an integer of 0 to 2,
R ₁ , R ₂ , R ₄ and R ₅ are the same or different and each independently represents -L ₁ - (A) _a , hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or unsubstituted C2-C30 heteroalkyl group, a substituted or unsubstituted C2-C30 alkynyl group, A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms (a and b are integers of 0 to 1), and R ₄ and R ₅ may be connected to each other to form a saturated or unsaturated ring. The method according to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 5:
[Chemical Formula 5]

In this formula,
A is a substituted or unsubstituted adamantyl group,
X is selected from the group consisting of N (R ₃ ), S, O, and Si (R ₄ ) (R ₅ )
m is an integer of 0 to 2,
R ₁ , R ₃ , R ₄ and R ₅ are the same or different and each independently represents -L ₁ - (A) _a , hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or unsubstituted C2-C30 heteroalkyl group, a substituted or unsubstituted C2-C30 alkynyl group, A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms (a and b are integers of 0 to 1), and R ₄ and R ₅ may be connected to each other to form a saturated or unsaturated ring. The method according to claim 1,
Wherein X is S The method according to claim 1,
Wherein X is O. The method according to claim 1,
Wherein X is Si (R ₄ ) (R ₅ ). The method according to claim 1,
The Ar < ₁ & Ar ₄ is A substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. The method according to claim 1,
R ₁ to R ₅ are the same or different and each independently represents a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C40 cycloalkyl group or a substituted or unsubstituted C6-C30 aryl group ≪ / RTI > The method according to claim 1,
Wherein L ₁ and L ₂ are selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 6 to 30 nucleus atoms. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of:

A first electrode; A second electrode facing the first electrode; And at least one organic layer provided between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises a compound according to claim 1. 12. The method of claim 11,
Wherein the organic material layer is at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer. 12. The method of claim 11,
Wherein the organic material layer is a light emitting layer. 12. The method of claim 11,
Wherein the organic material layer includes a hole injection layer, a hole transporting layer, and an electron blocking layer.