KR20160041124A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The purpose of the present invention is to provide: a compound, capable of improving the durability, having a low driving voltage, and having high light-emitting efficiency of an element; an organic electrical element using the same; and an electronic device thereof. The compound is represented by chemical formula 1, comprising at least one cross-linking formation group represented by at least one of CL^1 to CL^3.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for organic electroluminescent devices, an organic electroluminescent device using the same, and an electronic device using the same. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent (EL)

TECHNICAL FIELD The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device therefor.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multi-layered structure made of different materials, and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

The most problematic lifetime and efficiency of the organic electroluminescent device is that the efficiency and lifetime problem must be solved as the display becomes larger.

The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage drops and the driving voltage drops. As a result, crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase.

However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimal combination of the energy level and the T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.

Recently, in order to solve the problem of light emission in the hole transporting layer in organic electroluminescent devices, a light-emitting auxiliary layer (or a second hole transporting layer) must exist between the hole transporting layer and the light emitting layer, It is necessary to develop different light-emission-assisted layers according to the method.

Generally, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination. However, the material used for the hole transport layer has a low HOMO value and therefore has a low T 1 value. As a result, the exciton generated in the light emitting layer is transferred to the hole transport layer, resulting in a charge unbalance in the light emitting layer. And emits light at the interface of the hole transporting layer.

When light is emitted from the interface of the hole transporting layer, the color purity and efficiency of the organic electronic device are lowered and the lifetime is shortened. Therefore, it is urgently required to develop a light emitting auxiliary layer having a high T 1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer.

On the other hand, it is a reality that a large-area display by a solution process is indispensable at a present time when the organic electroluminescence device is required to have a large area. Polymer materials have been studied as a material for the solution process, but the crosslinking-free solution process causes the lower film to be eroded by the solvent used in forming the upper film, thereby damaging the lower film. As a result, the characteristics of the device are deteriorated and the process yield is lowered.

Crosslinking is essential for preventing erosion of the lower film during formation of the upper film, and a compound capable of crosslinking has high solubility in organic solvent before crosslinking and low solubility in organic solvent after crosslinking.

As a method of forming the crosslinking, there are a method of crosslinking by light and a method of crosslinking by heat. Light crosslinking has the advantage of rapid crosslinking at low temperatures, but it requires a photoinitiator, which acts as an impurity in the device and leads to a problem of deterioration of properties. On the other hand, cross-linking through heat is known to enhance device characteristics, although long time high temperature is required.

In order to sufficiently exhibit the excellent characteristics of the organic electroluminescent device described above, a material constituting the organic material layer in the device such as a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, However, the development of a stable and efficient organic material layer for an organic electric device has not yet been sufficiently developed. Therefore, the development of new materials is continuously required.

The present invention has been proposed in order to solve the above-mentioned problems of the prior art. The present invention has an excellent solubility by an organic solvent and enables a solution process in the production of an organic electric device, (I.e., a second hole transport layer), and a light emitting layer material in the organic electroluminescent device manufactured using the organic electroluminescent device, and in particular, it can be used alone as a hole transport layer, a light emitting auxiliary layer, An organic electroluminescent device using the same, and an electronic device using the same.

The solubility of the compound of the present invention varies depending on the kind and / or number of the repeating unit and the resistance of the thin film to the solvent when the thin film is formed.

In one aspect, the present invention provides an organic electroluminescent compound characterized by having a repeating unit represented by the following formula and having crosslinking properties.

The moiety A in the above formula is of the following formula.

In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.

Increasing the number of repeating steps in the compounds of the present invention may increase the resistance of the thin film to solvents upon formation of the thin film. In addition, by introducing a substituent having cross-linking properties into the compound of the present invention together with the above characteristics, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the lifetime of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is an illustration of an organic electroluminescent device according to the present invention. FIG.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

It should be noted that, in adding reference numerals to the constituent elements of the drawings, the same constituent elements are denoted by the same reference numerals even though they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements. When a component is described as being "connected", "coupled", or "connected" to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be "connected," "coupled," or "connected."

As used in this specification and the appended claims, unless stated otherwise, the following terms have the following meanings:

The term " halo "or" halogen ", as used herein, unless otherwise indicated, is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I).

The term "alkyl" or "alkyl group ", as used herein, unless otherwise indicated, has a single bond of from 1 to 60 carbon atoms and includes straight chain alkyl groups, branched chain alkyl groups, cycloalkyl (alicyclic) Alkyl " means a radical of a saturated aliphatic group, including alkyl, cycloalkyl-substituted alkyl groups.

The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.

The term "heteroalkyl group" as used herein means that at least one of the carbon atoms constituting the alkyl group is replaced by a heteroatom.

The term "alkenyl group" or "alkynyl group ", as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.

The term "cycloalkyl" as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.

The term "alkoxyl group "," alkoxy group ", or "alkyloxy group" used in the present invention means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.

The term "alkenoyl group "," alkenoyl group ", "alkenyloxy group ", or" alkenyloxy group "as used in the present invention means an alkenyl group to which an oxygen radical is attached, , But is not limited thereto.

As used herein, the term "aryloxyl group" or "aryloxy group" refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.

The terms "aryl group" and "arylene group ", as used herein, unless otherwise specified, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or a multicyclic aromatic group, and neighboring substituents include aromatic rings formed by bonding or participating in the reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorene group, a spirobifluorene group, or a spirobifluorene group.

The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, the arylalkyl group is an alkyl group substituted with an aryl group, the arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the carbon number described in the present specification.

Also, if prefixes are named consecutively, it means that the substituents are listed in the order listed first. For example, the arylalkoxy group means an alkoxy group substituted with an aryl group, the alkoxycarbonyl group means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, an alkenyl group substituted with an arylcarbonyl group means Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heteroalkyl ", as used herein, unless otherwise indicated, means an alkyl comprising one or more heteroatoms. The term "heteroaryl group" or "heteroarylene group" as used in the present invention means an aryl or arylene group having 2 to 60 carbon atoms each containing at least one heteroatom unless otherwise specified, And includes at least one of a single ring and a multi-ring, and neighboring functional devices may be formed in combination.

The term "heterocyclic group ", as used herein, unless otherwise specified, includes one or more heteroatoms, has from 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, Aromatic rings. Adjacent functional groups may be combined and formed.

As used herein, the term "heteroatom " refers to N, O, S, P or Si unless otherwise stated.

The "heterocyclic group" may also include a ring containing SO ₂ in place of the carbon forming the ring. For example, the "heterocyclic group" includes the following compounds.

Unless otherwise stated, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms and an "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring of 3 to 60 carbon atoms or an aromatic ring of 6 to 60 carbon atoms or a heterocycle of 2 to 60 carbon atoms, or combinations thereof, Saturated or unsaturated ring.

Other hetero-compounds or hetero-radicals other than the above-mentioned hetero-compounds include, but are not limited to, one or more heteroatoms.

Unless otherwise specified, the term "carbonyl" as used herein refers to -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, A cycloalkyl group of 2 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise indicated, the term "ether" used in the present invention refers to -RO-R 'wherein R or R' are each independently of the other hydrogen, an alkyl group having 1 to 20 carbon atoms, An aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

One also no explicit description, the terms in the "unsubstituted or substituted", "substituted" is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C for use in the present invention ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron Means a group substituted with at least one substituent selected from the group consisting of a halogen atom, a halogen atom, a cyano group, a germanium group, and a C ₂ to C ₂₀ heterocyclic group.

Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.

When a is an integer of 0, substituent R ¹ is absent. When a is an integer of 1, one substituent R ¹ is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as follows: and wherein R ¹ may be the same or different from each other, a is the case of 4 to 6 integer, and bonded to the carbon of the benzene ring in a similar way, while the display of the hydrogen bonded to the carbon to form a benzene ring Is omitted.

1 is an illustration of an organic electroluminescent device according to an embodiment of the present invention.

1, an organic electroluminescent device 100 according to the present invention includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110, ) Comprising an organic compound layer comprising a compound according to the present invention. In this case, the first electrode 120 may be an anode and the second electrode 180 may be a cathode (cathode). In case of an inverting type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, the remaining layers except the light emitting layer 150 may not be formed. An electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like, and the electron transport layer 160 may serve as a hole blocking layer.

Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

The compound according to the present invention applied to the organic material layer may include a hole injecting layer 130, a hole transporting layer 140, an electron transporting layer 160, an electron injecting layer 170, a light emitting auxiliary layer 151, Or a material of a dopant or a light-efficiency improvement layer. Preferably, the compound of the present invention may be used as the hole injecting layer 130, the hole transporting layer 140, the light emitting auxiliary layer 151, and the light emitting layer 150.

On the other hand, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at any position even in the same core, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and T1 value and the intrinsic properties (mobility, interfacial characteristics, etc.) between the organic layers are achieved, it is possible to achieve long life and high efficiency at the same time.

Accordingly, in the present invention, by forming the light emitting layer using the compound represented by the general formula (1), it is possible to optimize the energy level and the Tl value between the respective organic layers, the mobility of the material, And efficiency can be improved at the same time.

The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a physical vapor deposition (PVD) method. For example, the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, and an electron transporting layer 160 and an electron injection layer 170, and then depositing a material usable as the cathode 180 on the organic layer.

In addition, the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.

The organic electroluminescent device according to the present invention may be of a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Typically, a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down , And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light from the electroluminescent material. Can be applied to such WOLED.

The organic electroluminescent device according to the present invention may be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochromatic or white illumination device.

Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. The electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, the compound according to one aspect of the present invention will be described.

In one aspect, the present invention relates to an organic electroluminescent device comprising a repeating unit represented by the following general formula (1) and having crosslinking characteristics including at least one crosslinking group represented by at least one of CL ¹ to CL ³ ≪ / RTI >

≪ Formula 1 >

The moiety A in the formula (1) has the following formula (a).

<Formula a>

In formula (1)

l is an integer from 0 to 2; o is an integer from 2 to 10;

Ar ¹ to Ar ³ independently represent a C ₆ to C ₆₀ aryl group; And a fluorenyl group; &Lt; / RTI &gt;

L is independently an aryl group of C ₆ to C ₆₀ ; A fluorenylene group; An alkenylene group having ₂ to ₆₀ carbon atoms; &Lt; / RTI &gt;

CL ¹ to CL ³ may independently be hydrogen or a crosslinking group. When CL ¹ to CL ³ are crosslinking groups, they are independently selected from the group consisting of vinyl group, acryloyl group, methacyloyl group, cyclic ethers, siloxanes Styrenes, trifluorovinyl ethers, benzocyclo-butenes, cinnamates, chalcones, and oxetanes; and the like; &Lt; / RTI &gt;

M is an integer of 0 to 4; n is an integer of 0 to 3;

X is NAr ^4, O, it may be S, CR ³ R ^4. Wherein Ar ⁴ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; And an arylalkyl group having ₇ to ₆₀ carbon atoms.

R ¹ and R ² are independently selected from: i) deuterium independently of one another; Tritium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An arylalkyl group of C ₇ to C ₆₀ ; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; A C ₆ to C ₃₀ aryloxy group, and the like.

In addition, R ¹ and R ² is ii) wherein n is 2 and m the same or different, each a plurality or more, a plurality of R ¹ and R ² may form a ring in combination, respectively. Wherein R ¹ and R ² which do not form a ring may be defined as defined above. Wherein the ring formed is a fused ring consisting of a C ₃ to C ₆₀ aliphatic ring or a C ₆ to C ₆₀ aromatic ring, a C ₂ to C ₆₀ heterocycle, a C ₃ to C ₆₀ alicyclic ring, Etc., and can be a single ring or multiple rings, as well as a saturated or unsaturated ring.

R ³ and R ⁴ independently of one another are a C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An arylalkyl group of C ₇ to C ₆₀ ; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; A C ₆ to C ₃₀ aryloxy group, and the like. And R &lt; ³ &gt; and R &lt; ⁴ &gt; may combine with each other to form a spiro compound.

For example, Ar ¹ to Ar ³ may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, or the like. L may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, or the like. R ¹ and R ² may be a phenyl group, a hexyl group, a phenylhexyl group, or the like. Ar ⁴ may be a phenyl group, a phenylhexyl group or the like. R ³ and R ⁴ may be a methyl group, a phenyl group, a hexyl group, a phenylbutyl group or the like.

Here, the aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group, alkenylene group, A halogen atom, a silane group, an alkenyloxy group, an ether group, an alkenylaryl group, a cycloalkyl group, a silane group, a siloxane group, an arylalkoxyl group, an arylalkenyl group, and an alkoxycarbonyl group, (alkylene group alkenylene group) siloxane group, a boron group, a germanium group, a cyano group, a nitro ^{group, -L b -N (R d)} (R e) ( wherein L ^b, R ^d and R ^e are the L ^a, R ^a and R ^b each as defined), C ₁ ~ Import alkylthio of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ of the alkenyl group, C ₂ ~ alkynyl of C ₂₀ , A C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, a fluorenyl group, a C ₂ to C ₂₀ heterocyclic group, a C ₃ to C ₂₀ cycloalkyl group, a C ₇ to C arylalkenyl of ₂₀ Group, C ₈ ~ C ₂₀ aryl alkenyl group, a carbonyl group, an ether group, C ₂ ~ C ₂₀ alkoxyl group, an aryloxy group of a C ₆ ~ C ₃₀ ^{of, -O-Si (R f)} 3, and R ^c O-Si (R ^f ) ₂ - (wherein R ^f is the same as the definition of R ^c ).

Specifically, at least one of CL ¹ to CL ³ in Formula 1 may include any one of the following Formulas h-1 to h-12.

<Formula h-1> <Formula h-2> <Formula h-3>

<Formula h-4> <Formula h-5> <Formula h-6>

<Formula h-7> <Formula h-8> <Formula h-9>

   <Formula h-10> <Formula h-11> <Formula h-12>

In the above formula (h-7)

q is an integer of 1 to 6;

More specifically,

의 경우, 할로겐으로 치환된 알켄일옥실기, 할로알켄일옥실기, 또는 트리플로오로비닐에테르로 분류될 수 있으며,I) a compound of formula h-2

, It may be classified into an alkenyloxy group substituted with a halogen, a haloalkenoyloxy group, or a trifluorovinyl ether,

의 경우, 할로알켄일옥시알킬, 또는 할로겐으로 치환된 에테르기로 분류될 수 있으며,Ii) a compound of formula h-3

For example, haloalkenyloxyalkyl, or an ether group substituted with a halogen,

의 경우, 알켄일아릴기로 분류될 수 있으며,Iii) The formula h-4

, It may be classified as an alkenyl aryl group,

의 경우, 할로알켄일옥실아릴기, 또는 에테르기로 분류될 수 있으며, Iv) a compound of formula h-5

, It may be classified as a haloalkenyloxylaryl group or an ether group,

의 경우, 방향족고리와 지방족고리의 융합고리기로 분류될 수 있으며,V) a compound of formula h-6

, It can be classified as a fused ring group of an aromatic ring and an aliphatic ring,

의 경우, 알켄일아릴알킬옥실기, 또는 알켄일아릴기로 치환된 알콕실기로 분류될 수 있으며,Vi) a compound of formula h-8

, It may be classified into an alkenyl arylalkyloxyl group or an alkoxyl group substituted with an alkenyl aryl group,

의 경우, 방향족고리와 지방족고리의 융합고리기로 치환된 알킬옥실기, 또는 에테르기로 명명할 수 있으며,Ⅶ) The formula h-9

An alkyloxyl group substituted with a fused ring group of an aromatic ring and an aliphatic ring, or an ether group,

의 경우, 알켄일아릴헤테로알킬기, 또는 에테르기로 분류될 수 있으며,Ⅷ) The formula h-10

, An alkenyl arylheteroalkyl group, or an ether group,

의 경우, 할로알켄일옥실기로 치환된 아릴헤테로알킬기, 또는 할로알켄일옥실기로 치환된 에테르기로 분류될 수 있으며(E) a compound represented by the formula h-11

, An arylheteroalkyl group substituted by a haloalkenoyloxy group, or an ether group substituted by a haloalkenoyloxy group,

의 경우, 알켄일아릴헤테로알킬아릴기, 또는 에테르기로 치환된 아릴기로 분류될 수 있다.X) Formula h-12

, An alkenylarylheteroalkylaryl group, or an aryl group substituted with an ether group.

Specifically, the compound represented by the formula (1) may be represented by the following formulas (2) to (5).

(2)

(3)

&Lt; Formula 4 >

&Lt; Formula 5 >

In the above formulas 2 to 5,

Wherein L, Ar ¹ to Ar ⁴ , CL ¹ to CL ³ , R ¹ to R ⁴ , l, m, n and o are the same as L, Ar ¹ to Ar ⁴ , CL ¹ to CL ³ , R ¹ to R ⁴ , l, m, n and o.

More specifically, the compounds represented by Chemical Formulas 1 to 5 may be any one of the following compounds.

In another embodiment, the present invention provides a compound for an organic electroluminescent device represented by the general formula (1).

In another embodiment, the present invention provides an organic electronic device containing the compound represented by the above formula (1).

The organic electroluminescent device includes a first electrode; A second electrode; And an organic material layer disposed between the first electrode and the second electrode. The organic material layer may include a compound represented by Formula 1, and the compound represented by Formula 1 may include a hole injecting layer, a hole transporting layer, , The light emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer. In particular, the compound represented by the formula (1) may be included in the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer and the light emitting layer.

Specifically, an organic electrical device including one of the compounds represented by Chemical Formulas 2 to 5 in the organic material layer may be provided. For example, it is possible to provide an organic electric device including the compound represented by the above-mentioned individual formulas (P-1 to P-189) in the organic material layer.

In still another embodiment, the compound is contained singly in at least one layer of the hole injection layer, the hole transport layer, the light emission assisting layer, the light emitting layer, the electron transport layer, and the electron injection layer of the organic material layer, Wherein the compound is contained in combination of two or more different compounds, or the compound is contained in combination with two or more kinds of other compounds. In other words, each of the layers may contain a compound corresponding to Formulas (1) to (5) alone, and may include a mixture of two or more compounds of Formulas (1) to (5) A mixture with a compound not corresponding to the invention may be included. Herein, the compound not corresponding to the present invention may be a single compound or may be two or more compounds. When the compound is contained in combination with two or more kinds of other compounds, the other compound may be a known compound of each organic layer or a compound to be developed in the future. At this time, the compound contained in the organic material layer may be composed of the same kind of compound, but it may be a mixture of two or more different kinds of compounds represented by the general formula (1).

For example, the organic electroluminescent device is characterized in that a molar ratio of a compound containing one crosslinking group forming group to another compound containing two or more crosslinking forming groups is mixed in a ratio of 99: 1 to 1:99 can do.

In another embodiment of the present invention, the light efficiency improving layer is formed on at least one side of the one side of the first electrode opposite to the organic layer, or one side of the one side of the second electrode opposite to the organic layer, And an organic electroluminescent device.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be specifically described with reference to examples, but the present invention is not limited to the following examples.

Synthetic example

The compounds represented by Formula 1 according to the present invention are synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below, but are not limited thereto.

<Reaction Scheme 1>

(Wherein A, L, Ar ¹ to Ar ³ , CL ¹ to CL ³ , R ¹ to R ⁴ , l and o are the same as defined in Formula 1)

I. Synthesis of Sub 1

Sub 1 of Scheme 1 can be synthesized by the reaction path of Scheme 2 and Scheme 3, but is not limited thereto.

<Reaction Scheme 2>

Examples of the synthesis of specific compounds belonging to Sub 1 are as follows.

1. Sub 1-15 Synthetic Example

<Reaction Scheme 3>

The starting material, 4,4'-dibromo-1,1'-biphenyl (30.00 g, 96.15 mmol) and N- (9,9-dimethyl- 3-amine (57.38 g, 96.15 mmol) was dissolved in toluene (500 ml) in a round bottom flask and Pd ₂ (dba) ₃ (4.40 g, 4.80 mmol) , 50% P (t-Bu) ₃ (2.33 ml, 9.61 mmol) and NaOt-Bu (10.64 g, 288.45 mmol) were added and stirred at 80 ° C. Upon completion of the reaction, the reaction mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. The concentrated compound was subjected to silicagel column to obtain 59.69 g (yield: 75%) of the product.

2. Sub 1-57 Synthetic Example

<Reaction Scheme 4>

To a solution of N- (4 - (((4 - ((1,2,2-trifluorovinyl) oxy) benzyl) oxy) benzoic acid was added to 4,4'-dibromo-1,1'- biphenyl (30.00 g, 96.15 mmol) Pd (d-Bu) ₃ (2.33 ml, 4.80 mmol), Pd ₂ (dba) ₃ (4.40 g, 4.80 mmol) 47.94 g (Yield: 69%) of the product was obtained by using Sub 1-15 synthesis method described above, NaOt-Bu (10.64 g, 288.45 mmol) and Toluene (500 ml).

3. Sub 1-78 Synthetic Example

<Reaction Scheme 5>

The starting material, N4- (4'-bromo- [1,1'-biphenyl] -4-yl) -N4 ' Dibenzo [b, d] furan-4-yl) amino] - [1,1'-biphenyl] -4-yl) (dibenzo [b, 4-yl) amino] - [1,1'-biphenyl] -4-yl) (dibenzo [b, d] furan- N4, N4'-bis (dibenzo [b, d] furan-4-yl) - [1,1'-biphenyl] -4,4'-diamine (30.00 g, 15.16 mmol) 4-yl) dibenzo [b, d] furan-4-amine (5.48 g, 15.16 mmol), Pd ₂ (dba) ₃ (0.70 g, 0.75 mmol), 50% P 29.11 g (Yield: 85%) of the product was obtained by using the sub 1-15 synthesis method described above (t-Bu) ₃ (0.36 ml, 1.51 mmol), NaOt-Bu (1.67 g, 45.48 mmol) and Toluene .

4. Sub 1-113 Synthetic Example

<Reaction Scheme 6>

(9,9-dimethyl-9H-fluoren-2-yl) phenyl) -4-vinylnaphthalene (30.00 g, 96.15 mmol) was added to the starting material, 4,4'-dibromo-1,1'- 1-amine (42.07 g, 96.15 mmol), Pd ₂ (dba) ₃ (4.40 g, 4.80 mmol), 50% P (t-Bu) ₃ (2.33 ml, 9.61 mmol), NaOt- 288.45 mmol) and Toluene (500 ml) were subjected to the Sub 1-15 synthesis method to obtain 52.07 g (yield: 81%) of the product.

5. Sub 1-117 Synthetic Example

<Reaction Scheme 7>

To the starting material, 4,4'-dibromo-1,1'-biphenyl (30.00 g, 96.15 mmol) was added N- (4- (9,9'-spirobi [fluoren] -2-yl) 1-amine (53.81 g, 96.15 mmol), Pd ₂ (dba) ₃ (4.40 g, 4.80 mmol), 50% P (t- Bu) ₃ (2.33 ml, 9.61 mmol), NaOt- 288.45 mmol) and Toluene (500 ml) were obtained 49.42 g (yield: 65%) of the product using Sub 1-15 synthesis method described above.

On the other hand, the compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.

[Table 1]

II. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction path of Reaction Scheme 8, but is not limited thereto.

<Reaction Scheme 8>

Examples of the synthesis of specific compounds belonging to Sub 2 are as follows.

1. Synthesis Example of Sub 2-30

<Reaction Scheme 9>

The starting material N - ([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'- biphenyl] -4-yl) (10.52 g, 40.69 mmol) and 9-phenyl-9H-carbazol-3-amine (30.00 g, 40.69 mmol) were added to a round bottom flask Pd ₂ (dba) ₃ (1.86 g, 2.03 mmol), 50% P (t-Bu) ₃ (1.00 ml, 4.06 mmol) and NaOt-Bu (4.50 g, 122.07 mmol) were dissolved in toluene Lt; RTI ID = 0.0 &gt; 80 C. &lt; / RTI &gt; Upon completion of the reaction, the reaction mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. The concentrated compound was subjected to silicagel column to obtain 31.68 g (yield: 85%) of the product.

2. Synthesis Example of Sub 2-44

<Reaction formula 10>

The starting material N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N- (9,9-diphenyl-9H-fluoren- Dibenzo [b, d] thiophen-4-ylmethyl) -9H-fluorene-2-amine (30.00 g, 27.34 mmol) (5.44 g, 27.34 mmol), Pd ₂ (dba) ₃ (1.25 g, 1.36 mmol), 50% P (t- Bu) ₃ (0.70 ml, 2.73 mmol), NaOt- Bu (3.02 g, 82.02 mmol) , And toluene (150 ml) were obtained 26.56 g (yield: 80%) of the product using the Sub 2-30 synthesis method described above.

.

3. Synthesis Example of Sub 2-69

<Reaction Scheme 11>

The starting material, N - ([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -5-vinylnaphthalen- 30.00 g, 54.29 mmol) to dibenzo [b, d] furan- 4-amine (9.90 g, 54.29 mmol), Pd 2 (dba) 3 (2.48g, 2.71mmol), 50% P (t-Bu) 3 ( 1.30 ml, 5.42 mmol), NaOt-Bu (6.00 g, 162.87 mmol) and Toluene (300 ml) were used to obtain 25.95 g (yield: 73%) of the product.

4. Synthesis Example of Sub 2-111

<Reaction Scheme 12>

To a solution of 4- (9,9-dimethoxyphenyl) naphthalen-1-amine (30.00 g, 62.97 mmol) in N- (4'- 9-dimethyl-9H-fluoren- 2-yl) aniline (17.97 g, 62.97 mmol), Pd 2 (dba) 3 (5.76g, 6.29mmol), 50% P (t-Bu) 3 (15.27ml, 6.29mmol ), NaOt-Bu (6.97 g, 188.91 mmol) and Toluene (320 ml) were subjected to the synthesis of Sub-2-30 to obtain 30.01 g (yield: 70%) of the product.

5. Synthesis Example of Sub 2-115

<Reaction Scheme 13>

To a solution of 4- (9,9-dimethoxyphenyl) naphthalen-1-amine (30.00 g, 62.97 mmol) in N- (4'- (25.66 g, 62.97 mmol), Pd ₂ (dba) ₃ (5.76 g, 6.29 mmol), 50% P (t-Bu) ₃ (15.27 ml, 6.29 mmol ), NaOt-Bu (6.97 g, 188.91 mmol) and Toluene (320 ml) were obtained 35.39 g (Yield: 70%) of the product using the Sub 2-30 synthesis method.

On the other hand, the compound belonging to Sub 2 may be, but not limited to, the following compound, and Table 2 shows the FD-MS value of the compound belonging to Sub 2.

[Table 2]

III. Product synthesis

After the Sub 1 (1 eq) and Sub 2 (1 eq.) In a round bottom flask was dissolved in _{Toluene, Pd 2 (dba) 3} (0.05 equiv), 50% P (t- Bu) 3 (0.1 eq.), NaOt- Bu (3 eq) was added and stirred at 80 [deg.] C. Upon completion of the reaction, the reaction mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. The concentrated compound was silicagel column to obtain the final product.

1. P-32 Synthetic Example

<Reaction Scheme 14>

Sub 1-15 (10.00 g, 12.07 mmol) and Sub 2-30 (11.05 g, 12.07 mmol) obtained in the above synthesis were dissolved in toluene (120 ml) in a round bottom flask. Pd ₂ (dba) ₃ (0.55 g, was added 0.60mmol), 50% P (t -Bu) 3 (0.30ml, 1.20mmol), NaOt-Bu (1.33g, 36.21mmol) and stirred at 80 ° C. Upon completion of the reaction, the reaction mixture is extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. The concentrated compound was subjected to silicagel column to obtain 16.05 g (yield: 80%) of the product.

2. Synthesis example of P-98

<Reaction Scheme 15>

Sub-2-44 (16.80 g, 13.83 mmol), Pd ₂ (dba) ₃ (0.63 g, 0.69 mmol), 50% P (t-Bu) were added to Sub 1-57 (10.00 g, 13.83 mmol) _{3 (0.33ml, 1.38mmol), NaOt} -Bu (1.53 g, 41.49 mmol), using the synthesis method of P-32 Toluene (150ml) product was 26.11 g (yield: 65%) was obtained.

3. Synthesis example P-127

<Reaction Scheme 16>

Sub 2-69 (2.89 g, 4.42 mmol), Pd ₂ (dba) ₃ (0.20 g, 0.22 mmol), 50% P (t-Bu) _{3 (0.10ml, 0.44mmol), NaOt} -Bu (0.48 g, 13.26 mmol), using the synthesis method of P-32 Toluene (100ml) product was 8.89 g (yield: 71%) was obtained.

4. Synthesis example of P-175

<Reaction Scheme 17>

Sub 2-111 (10.19 g, 14.95 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.50 mmol) and 50% P (t-Bu) were added to Sub 1-113 (10.00 g, 14.95 mmol) 12.54 g (Yield: 70%) of the product was obtained by using the P-32 synthesis method described above, ₃ (0.36 ml, 1.49 mmol), NaOt-Bu (1.65 g, 44.85 mmol) and Toluene (150 ml).

5. Synthesis example of P-181

<Reaction Scheme 18>

Sub 2-115 (10.14 g, 12.64 mmol), Pd ₂ (dba) ₃ (0.57 g, 0.63 mmol) and 50% P (t-Bu) were added to Sub 1-117 (10.00 g, 12.64 mmol) 16.44 g (Yield: 86%) of the product was obtained by using the above P-32 synthetic method using ₃ (0.30 ml, 1.26 mmol), NaOt-Bu (1.39 g, 37.92 mmol) and Toluene (100 ml).

Meanwhile, the FD-MS values of the compounds P-1 to P-189 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Evaluation of manufacturing of organic electric device

[Example 1]

The ITO (Indium Tin Oxide) layer was patterned to have a light emitting area of 3 mm x 3 mm on the substrate and then cleaned. After the substrate was mounted on a spin coater, PEDOT: PSS was spin-coated on the ITO layer to a thickness of 50 nm. Thereafter, the resultant was dried on a hot plate at 150 ° C for 10 minutes to remove the solvent. The compound P-1 of the present invention, which is a hole transporting material, was dissolved in xylene and spin-coated to a thickness of 30 nm. Then, it was dried on a hot plate at 100 DEG C for 10 minutes, and then crosslinked by heating at 200 DEG C for 30 minutes. On the hole transport layer, DPNBi was doped with 96: 4 with ADN as a dopant material as a host material of the light emitting layer,

The solution is spin-coated to a thickness of 30 nm, dried on a hot plate at 100 ° C for 10 minutes, and mounted in a vacuum chamber so that the base pressure is 1 × 10 ^-6 torr. Subsequently, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum was vapor-deposited to a thickness of 10 nm as a hole blocking layer, Aluminum) was deposited to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide serving as an electron injecting layer, was vapor-deposited to a thickness of 0.5 nm, and then Al was vapor-deposited to a thickness of 150 nm to form an organic electroluminescent device.

[Example 2] to [Example 80]

An organic electroluminescent device was prepared in the same manner as in Example 1 except that the compounds P-9 to P-189 of the present invention described in Table 4 were used instead of the compound P-1 of the present invention as the hole transport layer material .

[Comparative Example 1]

An organic electroluminescence device was prepared in the same manner as in Example 1, except that the following compound 1 was used instead of the compound P-1 of the present invention as a hole transport layer material.

<Comparative Compound 1>

[Comparative Example 2]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the following compound 2 was used instead of the compound P-1 of the present invention as a hole transport layer material.

&Lt; Comparative Compound 2 >

[Comparative Example 3]

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the following compound 3 was used instead of the compound P-1 of the present invention as a hole transport layer material.

&Lt; Comparative Compound 3 >

[Comparative Example 4]

An organic electroluminescence device was prepared in the same manner as in Example 1, except that the following compound 4 was used instead of the compound P-1 of the present invention as a hole transport layer material.

<Comparative Compound 4>

Electruminescence (EL) characteristics were measured with photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 80 and Comparative Example 1 and Comparative Example 4 of the present invention And the T95 lifetime was measured by a life measuring apparatus manufactured by Mac Science Inc. at a reference luminance of 500 cd / m ^2. The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, the organic electroluminescent device using the compound of the present invention as a hole transporting layer material has improved luminous efficiency as compared with an organic electroluminescent device using Comparative Compounds 1 to 4 as a hole transporting layer material, And so on.

These results indicate that the compound of the present invention having an increased repetition rate is relatively more distant from the crosslinking group than the comparative compound 1 to the comparative compound 4, making crosslinking easier and increasing the molecular weight. Thus, And the resistance is increased.

Taken together, the above-mentioned characteristics indicate that introduction of a substituent having cross-linking characteristics and increase of repeating steps can greatly change the thin film characteristics, electrical characteristics and interface characteristics, Can exhibit low contact pressure, high luminous efficiency and high curability, and can greatly improve lifetime, thereby showing excellent materials for solution processing materials.

Although the device characteristics have been described from the viewpoint of the hole transport layer in the evaluation results of the above-described device fabrication, the materials commonly used as the hole transport layer are organic electroluminescent materials such as the electron transport layer, electron injection layer, hole injection layer, It can be used in combination with a single or other material as the organic layer of the device. Therefore, the compound of the present invention can be used alone or in combination with other organic materials other than the hole transporting layer, for example, an electron transporting layer, an electron injecting layer, a hole injecting layer, a light emitting layer and a light emitting auxiliary layer.

The foregoing description is merely illustrative of the present invention, and various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all techniques within the scope of the same should be construed as being included in the scope of the present invention.

100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: Hole transport layer 141: Buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (10)

A compound, characterized in that it has a crosslinking property, including, and represented by the formula ^1, CL 1 to CL at least one crosslinking-forming represented by at least one of the ^three.
&Lt; Formula 1 >

The moiety A in the formula (1) has the following formula (a).
<Formula a>

In Formula 1,
A moiety is of the following formula a,
Ar ¹ to Ar ³ independently represent a C ₆ to C ₆₀ aryl group; And a fluorenyl group; , &Lt; / RTI &gt;
L is independently an aryl group of C ₆ to C ₆₀ ; A fluorenylene group; An alkenylene group having ₂ to ₆₀ carbon atoms; , &Lt; / RTI &gt;
CL ¹ to CL ³ are each independently hydrogen or a crosslinking group, and when CL ¹ to CL ³ are crosslinking groups, they may be independently selected from a vinyl group, but are not limited to, methacyloyl groups, cyclic ethers, siloxanes, styrenes, trifluorovinyl ethers, benzocyclo-butenes, cinnamates, chalcones, and oxetanes; , &Lt; / RTI &gt;
M is an integer of 0 to 4; n is an integer of 0 to 3,
X is NAr ^4, O, it may be S, CR ³ R ^4. Wherein Ar ⁴ is a C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₇ to C ₆₀ arylalkyl group,
R ¹ and R ² are independently selected from: i) deuterium independently of one another; Tritium; halogen; A C ₆ to C ₆₀ aryl group; A fluorenyl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An arylalkyl group of C ₇ to C ₆₀ ; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; An aryloxy group of C ₆ to C ₃₀ , or R ¹ and R ² are the same as or different from each other when n and m are two or more, and a plurality of R ¹ and R ² are the same or different, To form a ring,
R ³ and R ⁴ independently of one another are a C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C ₁ to C ₅₀ alkyl group; An arylalkyl group of C ₇ to C ₆₀ ; A fused ring group of an aromatic ring of C ₆ to C ₆₀ and an aliphatic ring of C ₃ to C ₆₀ ; An alkenyl group having ₂ to ₂₀ carbon atoms; A C ₁ to C ₃₀ alkoxyl group; A C ₆ to C ₃₀ aryloxy group,
The aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxyl group, the aryloxy group, the arylene group, the fluorenylene group, the alkenylene group, and the arylalkyl group each may be substituted with deuterium, silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro ^{group, -L b -N (R d)} (R e) ( wherein L ^b, R ^d and R ^e are the L ^a, R ^a, respectively, and are the same) and the definition of R ^b, C ₁ ~ Import alkylthio of C _20, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ alkyl group of C _20, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C ₂₀ of the A C ₆ to C ₂₀ aryl group, a C ₆ to C ₂₀ aryl group substituted with deuterium, a fluorenyl group, a C ₂ to C ₂₀ heterocyclic group, a C ₃ to C ₂₀ cycloalkyl group, a C ₇ ~ C ₂₀ aryl group, an aryloxy group of C ₈ ~ C ₂₀ aryl alkenyl group, a carbonyl group, an ether group, C ₂ ~ C ₂₀ alkoxyl group, a C ₆ ~ C ₃₀ of the, -O-Si (R ^f ) ₃ , and R ^c O-Si (R ^f ) ₂ - (wherein R ^f is the same as the definition of R ^c ) &Lt; / RTI &gt; and the like. The method according to claim 1,
Wherein at least one of CL &^lt; ¹ > to CL &^lt; ³ >
<Formula h-1><Formulah-2><Formulah-3>

<Formula h-4><Formulah-5><Formulah-6>

<Formula h-7><Formulah-8><Formulah-9>

<Formula h-10><Formulah-11><Formulah-12>

(In the above formula h-7, q is an integer of 1 to 6) The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by the following formula.
(2)

(3)

&Lt; Formula 4 >

&Lt; Formula 5 >

(Wherein L, Ar ¹ to Ar ⁴ , CL ¹ to CL ³ , R ¹ to R ⁴ , l, m, n and o are the same as defined in claim 1) The method according to claim 1,
Wherein the compound represented by Formula 1 is one of the following compounds.

A first electrode;
A second electrode; And
And an organic material layer disposed between the first electrode and the second electrode,
Wherein the organic material layer contains the compound of any one of claims 1 to 4. 6. The method of claim 5,
Wherein the compound is contained in at least one of the hole injection layer, the hole transport layer, the light emission assisting layer and the light emitting layer of the organic material layer. 6. The method of claim 5,
Wherein a molar ratio of a compound containing one crosslinking group forming group to another compound containing two or more crosslinking forming groups is mixed in the range of 99: 1 to 1:99. 6. The method of claim 5,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device comprising the organic electroluminescent device of claim 5; And
And a control unit for driving the display device. 10. The method of claim 9,
Wherein the organic electroluminescent device is one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, and a monochromatic or white illumination device.

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