KR20190081262A - Novel compound and organic electroluminescent device including the same - Google Patents

Abstract

The present invention relates to a novel compound comprising a crosslinking group, a solution process composition comprising the same, and an organic light emitting device comprising the same. It is possible to improve resistance of a solvent when manufacturing a subsequent layer by forming an insoluble layer when a compound is laminated by crosslinking. Accordingly, the compound according to the present invention can be used in the organic light emitting device, thereby realizing long lifespan, driving stability, and high efficiency of the organic light emitting device.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and an organic light-

The present invention relates to a novel compound containing a crosslinking group, a composition for forming an organic layer of an organic light emitting device comprising the same, and an organic light emitting device comprising the same.

A material used as an organic material layer in the organic electroluminescent device (OLED) can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from an electron triplet excited state according to a light emitting mechanism, The light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant and the host.

In organic electroluminescent devices, since most low-molecular materials are manufactured by a vacuum deposition method, it is difficult to form a film having a relatively high production cost and uniform film characteristics, compared with a wet process, And large area production is difficult. Further, the organic electroluminescent device uses multiple layers of various functions for high efficiency and long life. Such a multilayer has, for example, an electron- and hole-injecting layer, a charge-transporting layer, an electron- and a hole-transporting layer, and a layer containing luminescent components, Lt; / RTI > Where multiple layers are applied in a solution process, the already applied layer should not be destroyed by subsequent application of the solution for subsequent layer preparation after it has been dried.

Korean Patent Publication No. 10-2015-0086721

In order to solve the above problems, the present invention provides a novel organic compound including a crosslinking group, a composition for forming an organic layer of the organic light emitting device comprising the same, and an organic light emitting device comprising the same.

However, the problems to be solved by the present invention are not limited to the problems described above, and other problems not described can be clearly understood by those skilled in the art from the following description.

An aspect of the present invention provides a compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

CL is hydrogen, an alkyl group or a crosslinked former of C ₁ ~ C _10,

R is hydrogen, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

L is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

n is an integer of 1 to 4, and when n is 2 or more, CL may be different from each other,

A ₁ is represented by the following general formula (1-1) or (1-2)

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

In the above formula (1-1) or (1-2)

Ar ₁ to Ar ₃ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

CL ₁ to CL ₃ are each independently a hydrogen or a crosslinking group,

L ₁ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

A ₂ and A ₃ are each independently represented by the following formula 1-3 or 1-4,

[Chemical Formula 1-3] [Chemical Formula 1-4]

In the above formulas 1-3 or 1-4,

Ar ₄ to Ar ₆ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

CL ₄ to CL ₆ are each independently a hydrogen or a crosslinking group,

L ₂ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

The CL, CL ₁ to CL at least one of the former ₆ is a cross-linked, with the proviso that the A ₁ is represented by the above formula 1-1, CL _1, this cross-linking the former and CL CL CL ₄ to ₆ of At least one is a crosslinking group.

Another aspect of the invention is a compound according to the invention; And a solvent having a boiling point of 100 to 400 DEG C and a viscosity of 0.1 to 15 cP.

Another aspect of the present invention provides an organic light emitting device comprising an organic material layer containing a polymer formed by the compound according to the present invention between a first electrode and a second electrode.

Since the compound of the present invention includes a crosslinking group, the insoluble layer can be formed through a crosslinking process after lamination by a solution process in the lamination of multiple layers of an organic light emitting device to improve the resistance to a solvent in the subsequent layer, The uniformity and stability of the thin film can be improved. Accordingly, the compound according to the present invention can be used in an organic light emitting device to realize long lifetime, driving stability, and high efficiency of the organic light emitting device.

In addition, the compound of the present invention can achieve a low voltage and a high efficiency by forming a HOMO level that facilitates injection of holes and transport of holes as the arylamine is bonded to the position 2 or 3 of the indole. In particular, the compound of the present invention may be more suitable for improving the solubility by the indole and forming the organic material layer in the solution process.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, embodiments and examples of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains.

It should be understood, however, that the present invention may be embodied in many different forms and is not limited to the embodiments and examples described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are denoted by like reference characters throughout the specification.

Throughout this specification, when a member is "on " another member, it includes not only when the member is in contact with the other member, but also when there is another member between the two members.

Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. The terms "about "," substantially ", etc. used to the extent that they are used throughout the specification are intended to be taken to mean the approximation of the manufacturing and material tolerances inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure. The word " step (or step) "or" step "used to the extent that it is used throughout the specification does not mean" step for.

Throughout this specification, the term "combination thereof" included in the expression of the machine form means one or more combinations or combinations selected from the group consisting of the constituents described in the expression of the machine form, And the like.

Throughout this specification, the description of "A and / or B" means "A or B, or A and B".

Throughout the specification, the term "aryl" refers to a C _6-50 aromatic hydrocarbon ring group such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, Means an aromatic ring such as phenyl, naphthyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, neopentyl, Examples of the C _5-50 aromatic ring containing a hetero element include pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Thienyl, and pyridine rings, pyrazine rings, pyrimidines, pyrimidines, pyrimidines, pyrimidines, pyrimidazines, pyrimidines, pyrimidines, pyrimidines, A pyridine ring, a triazine ring, an indole ring, a quinoline A pyridine ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzo ring, an oxadiazole ring, an oxadiazole ring, an oxadiazole ring, an oxadiazole ring, May mean to include a heterocyclic group formed from an oxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring have.

Throughout the present specification the term "substituted" as in "substituted or unsubstituted" is a deuterium, a halogen, an amino group, a nitrile group, a nitro group or a C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ - can mean substituted with one or more groups selected from C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C ₃₀ aryl group and C ₃ ~ a heteroaryl group the group consisting of the C ₃₀ of the.

In addition, throughout the present specification, the same symbols may have the same meanings unless otherwise specified.

An aspect of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

CL is hydrogen, an alkyl group or a crosslinked former of C ₁ ~ C _10,

R is hydrogen, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

L is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

n is an integer of 1 to 4, and when n is 2 or more, CL may be different from each other,

A ₁ is represented by the following general formula (1-1) or (1-2)

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

In the above formula (1-1) or (1-2)

Ar ₁ to Ar ₃ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

CL ₁ to CL ₃ are each independently a hydrogen or a crosslinking group,

L ₁ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

A ₂ and A ₃ are each independently represented by the following formula 1-3 or 1-4,

[Chemical Formula 1-3] [Chemical Formula 1-4]

In the above formulas 1-3 or 1-4,

Ar ₄ to Ar ₆ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

CL ₄ to CL ₆ are each independently a hydrogen or a crosslinking group,

L ₂ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,

The CL, CL ₁ to CL at least one of the former ₆ is a cross-linked, with the proviso that the A ₁ is represented by the above formula 1-1, CL _1, this cross-linking the former and CL CL CL ₄ to ₆ of At least one is a crosslinking group.

The compound according to one embodiment of the present invention has a crosslinking group forming agent, and can form cross-linking between compounds when forming a thin film layer with the compound according to the present invention. Thus, if an organic layer is additionally formed through a solution process on top of the thin film layer, the thin film layer formed with the compound according to the present invention may have solvent resistance to the subsequent layer.

In general, when a thin film is formed of a polymer having a high molecular weight in order to improve the thin film characteristics, the solubility is low and it is difficult to produce an organic light emitting device by a solution process. When a substituent is bonded to increase the solubility of the polymer, it may be possible to laminate by a solution process. However, when the subsequent layer is laminated by a solution process after the formation of the thin film, resistance to the solvent of the subsequent layer is decreased, There may be a problem of mixing with the layer.

However, since the compound according to the present invention has a high solubility, it is easy to control the solution process because it is highly soluble in a solvent, and since the molecular weight is increased through crosslinking after the formation of a thin film, a solvent resistance have.

In one embodiment of the present invention, the compound may be represented by the following general formula (2).

(2)

In one embodiment of the present invention, the compound may be represented by the following general formula (3) or (4).

(3)

 [Chemical Formula 4]

In Formula 3 or Formula 4,

The two Ar ₄ may be the same or different. In addition, the two CL ₄ may be the same or different from each other.

Further, in one embodiment of the present invention, the compound may be represented by the following general formula (5) or (6).

[Chemical Formula 5]

[Chemical Formula 6]

In one embodiment of the present invention, the compound may be represented by the following general formula (7) or (8).

 (7)

 [Chemical Formula 8]

In Formula 7 or Formula 8,

The two Ar _{5 s} may be the same or different and the two Ar _{6 s} may be the same or different. In addition, the two CL ₅ may be the same or different from each other, two CL ₆ may be the same or different from each other.

According to an embodiment of the present invention, at least two of CL ₄ to CL ₆ in Formula 3 may be a crosslinking-forming group, and at least two of CL ₅ to CL ₆ in Formula 4 may be a crosslinking- .

In one embodiment of the present invention, CL and CL ₁ in Formula 3 or Formula 4 may all be hydrogen.

In one embodiment of the present invention, L, L ₁ , and L ₂ can each independently be phenyl, naphthyl, biphenyl, dimethylfluorene or dibenzofuran, have. In this case, high efficiency and long life of the organic light emitting device can be realized.

In one embodiment of the invention, the compound may have two or more crosslinking groups. In this case, the crosslinking formation rate is increased and solvent resistance can be increased. According to one embodiment of the present invention, at least two of CL ₄ to CL ₆ may be a crosslinking-forming group.

According to one embodiment, the CL and CL ₁ may be hydrogen.

In one embodiment of the present invention, Ar ₁ to Ar ₆ each independently represents a substituted or unsubstituted phenyl, biphenyl, terphenyl, dimethylfluorene, dibenzofuran, dibenzothiophene, naphthyl, Fluorene, spirobifluorene, and combinations thereof.

In one embodiment of the present invention, the cross-linking group may be a functional group capable of forming a chemical bond between a molecule and a molecule and capable of forming an insoluble compound through a cross-linking reaction.

In one embodiment of the present invention, the crosslinking reaction may be carried out by polymerization of crosslinking groups of the same structure or by polymerization of crosslinking groups of different structures. The cross-linking group may include a double bond or a cyclic compound. Specific examples thereof include a vinyl group, an acryloyl group, a methacyloyl group, a cyclic ether, Siloxane, styrene, trifluorovinyl ether, benzocyclo-butane, cinnamate, chalcone, or oxetane. The term " But is not limited thereto.

When the organic light emitting device is laminated by the solution process in the multilayer lamination of the organic light emitting device, the crosslinking process is crosslinked to form the insoluble layer, so that the subsequent layer is formed by the solution process, And the uniformity and stability of the thin film can be improved through crosslinking. The term "insoluble" in the context of the present invention specifically means that the crosslinking compound according to the invention after the crosslinking reaction, that is, the reaction of the crosslinking groups through the curing process, Specifically, it has a solubility of 10 times or less.

In one embodiment of the present invention, the crosslinking group forming unit may be any one of the following structural formulas.

In the above formula,

Y is a direct bond, a substituted or unsubstituted C ₁ -C ₁₈ alkyl group, a substituted or unsubstituted C ₆ -C ₁₈ arylalkyl group, a substituted or unsubstituted C ₂ -C ₁₈ alkenyl group, of a C ₁ ~ C ₁₈ alkoxy group, a substituted or unsubstituted C ₃ ~ C ₁₈ of octanoic seten group, a substituted or unsubstituted C ₃ ~ C ₁₈ acetate group, a substituted or unsubstituted C ₃ ~ C ₁₈ rings of A substituted or unsubstituted C ₃ -C ₁₈ aryloxy group, a substituted or unsubstituted C ₃ -C ₁₈ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₁₈ aryl group, or a substituted or unsubstituted C ₃ -C ₁₈ aryloxy group, An unsubstituted C ₃ to C ₁₈ carbonyl group, and a dotted line is a bonding position.

For example, the crosslinking groups may form cross-links when laminated for application to devices, as in the following reaction schemes. As an example of the crosslinking, the following schemes can be used for polymerization of crosslinking groups having different structures in addition to polymerization of crosslinking groups having the same structure as described below.

According to one embodiment of the present invention, when the cross-linking group includes a vinyl group, it may be a polymer having repeating units as described below.

According to one embodiment of the present invention, when the cross-linking group forming agent is trifluoro vinyl ether, it may be a polymer having repeating units as described below.

According to one embodiment of the present invention, when the cross-linking group forming agent is benzocyclobutane, it may be a polymer having repeating units as described below.

The reaction of such a crosslinking grouping agent can result in a crosslinked compound. Cross-linking may be accomplished by a curing process, including but not limited to, reaction by heating, UV, microwave, X-ray or electron beam irradiation in the presence of an initiator.

For example, the heating method may be performed at a temperature of about 200 ° C for about 10 minutes to about 120 minutes. Since the heat curing process does not require an initiator, an additive such as photo-curing is not required and reaction byproducts are not produced, which is suitable for the production of an OLED by a solution process and excellent characteristics can be obtained.

The polymerization mechanism using the vinyl structure may follow a radical polymerization mechanism.

In one embodiment of the present invention, the compound represented by Formula 1 may include, but is not limited to, the following compounds.

According to one embodiment of the present invention, the compound represented by Formula 1 may be the following compounds among the compounds, and these compounds have a proper HOMO level and high hole transporting ability as a hole transporting layer and have a high rate of crosslinking formation .

Another aspect of the present invention is a compound represented by Formula 1 above; And a solvent having a boiling point of 100 to 400 DEG C and a viscosity of 0.1 to 15 cP.

The composition for solution process of the present invention can prevent volatilization during the process due to high boiling point, exhibit excellent process control characteristics, and enable the composition to be injected at a higher frequency by lower viscosity.

The composition can be used to make electronic devices using solution process printing techniques such as ink-jet printing, roll printing or screen printing.

In one embodiment of the invention, the solvent is selected from the group consisting of o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, But are not limited to, formamide, 2-chloro-6-fluorotoluene, 2- fluoroanisole, anisole, 2,3-dimethylpyrazine, 4-fluoroanisole, 3- 2-fluorobenzonitrile, 2-fluorobenzonitrile, 2-fluorobenzonitrile, 2-fluorobenzonitrile, Dimethylaniline, N, N-dimethylaniline, N, N-dimethylaniline, 1- But are not limited to, fluoro-3,5-dimethoxybenzene, N-methylpyrrolidinone, 3-fluorobenzotrifluoride, benzotrifluoride, dioxane, trifluoromethoxybenzene, 4-fluorobenzotrifluoride, 3-fluoropyridine, toluene, 2- 2-fluorobenzotrifluoride, 3-fluorotoluene, pyridine, 4-fluorotoluene, 2,5-difluoro-toluene, 1-chloro-2,4-difluorobenzene, 2 1-chloro-2,5-difluorobenzene, 4-chlorofluorobenzene, chlorobenzene, 2-chlorofluorobenzene, 3-phenoxytoluene, 1- Benzophenone, isophorone, butoxygen, benzyl butyl ether, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy- Benzene, 1,4-benzodioxane, 1,3-dipropoxybenzene, 2,5-dimethoxytoluene, 4-ethylphenetol, 1,2,4-trimethoxy Benzene, 4- (1-propenyl) -1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert- 1,2-dimethoxybenzene, phenetole, 2-methoxy toluene 3-methoxy toluene, 2,2-dimethyl-1,3-benzodioxole, 4-methoxy toluene, benzyl methyl ether, 1,8-cineol, allyl phenyl ether, 2,3- 2-methylbenzofuran, 2,3-dihydrobenzofuran, 3,5-dimethyl anisole, 2,5-dimethyl anisole, 4-ethyl anisole, Benzene, p-xylene, m-xylene, and combinations thereof.

In one embodiment of the present invention, the solvent may have a boiling point of greater than 200 < 0 > C and a viscosity of less than 10 cP.

In solution processes, a high boiling point allows the ink to remain wet for a longer period of time after the solution process, providing better process control during drying, and providing better control over more uniform film and film profiles. In addition, the low viscosity of the solvent makes it possible to spray the composition with a higher frequency.

In one embodiment of the present invention, the solvent may include a solvent blend in which two or more solvents are mixed, and when the solvent blend is used, control over the viscosity and boiling point of the composition is facilitated.

The solvent blend may comprise a first solvent having a boiling point greater than 200 ° C, for example greater than 200 ° C and less than 400 ° C, and a viscosity less than 10 cP, such as 0.1 to 9 cP, And a second solvent having a lower boiling point. For example, the second solvent may be selected from the group consisting of benzenes substituted with one or more of alkylalkoxy, alkylthio or alkylamino substituents, such as 4-methyl anisole, mesitylene, butylbenzene and ortho- Lt; / RTI > Specifically, the second solvent has a boiling point of 200 ° C to 250 ° C and a viscosity in the range of 1 to 5 cP. The solvent blend can form a better thin film when it is a blend of a first solvent and a second solvent having a lower boiling point than the first solvent.

In one embodiment of the present invention, the compound represented by Formula 1 may be contained in an amount of 0.01 to 3 wt% based on the total weight of the composition. If the weight of the compound is less than 0.01 wt%, the thickness of the thin film may be too thin. If the weight of the compound is more than 3 wt%, the thickness of the thin film may be too thick or crystallization may occur.

Another aspect of the present invention provides an organic light emitting device comprising a polymer of the compound represented by Formula 1.

The organic light emitting device may include at least one organic compound layer containing a polymer formed by the compound according to the present invention between the first electrode and the second electrode.

In one embodiment of the present invention, the compound represented by Formula 1 is crosslinked to form a polymer, and the polymer of the compound thus formed may have a low solubility to form an insoluble layer.

In one embodiment of the present invention, the degree of insolubility of the polymer layer may be defined as follows, the degree of insolubility may be from 0.6 to 1, and specifically the degree of insolubility may be from 0.7 to 1, more specifically from 0.9 to 1 have. If the degree of insolubility is less than 0.6, the loss of the organic film may be too much, and it may be difficult to expect a high efficiency and a long-life effect.

Degree of insolubility = thickness after washing with organic solvent after crosslinking (B) / thickness (A) of initial thin film after crosslinking

More specifically, the degree of insolubility can be measured as follows. The compound according to an embodiment of the present invention may be dissolved in an organic solvent to form a thin film layer, and the thin film layer may be crosslinked to form a thin film layer having a thickness of 30 to 100 nm. This is referred to as the initial thickness (A) of the thin film, and the thin film thickness (B) after washing with an organic solvent can be measured. The cleaning may be performed from one to three times, though not limited thereto. The degree of insolubility can be determined by comparing the initial thickness (A) with the thickness after cleaning (B).

In one embodiment of the present invention, the organic layer may be a hole injection layer, a hole transport layer, or a light emission assist layer, and may be, for example, a hole transport layer, but is not limited thereto. The compounds of the present invention may be used alone or in combination with known compounds when forming an organic layer.

In one embodiment of the present invention, the organic light emitting device may include, but not limited to, an organic material layer containing a hole transporting material and an organic material layer containing a polymer of the compound represented by the formula (1).

The organic light emitting device includes an organic layer such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode One or more layers may be included.

For example, the organic light emitting device can be fabricated as shown in FIG. The organic light emitting device includes an anode (hole injection electrode 1000), a hole injection layer 200, a hole transport layer 300, a light emitting layer 400, an electron transport layer 500, an electron injection layer 600, Implantation electrode 2000) may be stacked in this order.

1, the substrate 100 may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. have.

The hole injection electrode 1000 is used as an anode for hole injection of the organic light emitting element. A material having a low work function may be used to inject holes and may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene.

A hole injecting layer material may be formed on the anode by vacuum deposition, thermal transfer, spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll through process, doctor blading, The hole injection layer 200 can be formed by a solution processing method such as a sputtering method or the like. When the hole injection layer is formed by the solution processing method, the coating thickness and the cross-linking conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and the thermal properties of the desired hole injection layer, Can be crosslinked at 100-250 占 폚 for 10 minutes to 120 minutes, and can be suitably selected in the layer thickness range of 10 占 퐉 to 5 占 퐉 (1 to 5000 nm).

Next, a hole transporting layer material is deposited on the hole injection layer 200 by vacuum deposition, thermal transfer, spin coating, nozzle printing, inkjet printing, slot coating, dip coating, The hole transport layer 300 can be formed by a solution process such as a screen printing process or a screen printing process. When the hole transporting layer is formed by the solution process, the coating thickness and the crosslinking conditions vary depending on the compound used, but it is generally preferable to select the coating thickness and the conditions under substantially the same conditions as the formation of the hole injection layer.

The hole transport layer 300 may be formed of a compound according to the present invention. When the organic light emitting device is laminated by a solution process and then subjected to a crosslinking process, an insoluble layer may be formed through a crosslinking reaction between the crosslinking groups . The insoluble layer formed by the crosslinking reaction may be excellent in uniformity and stability of the thin film. Further, when the subsequent layer is laminated by a solution process thereafter, the resistance of the subsequent layer to the solvent can be improved, and the uniformity and stability of the thin film can be improved through crosslinking.

As described above, the compound according to the present invention can be used alone or a known compound can be used together. In addition, according to one embodiment of the present invention, the hole transport layer 300 may have one or more layers, and may include a hole transport layer formed only of a known material. According to an embodiment of the present invention, the light-emitting auxiliary layer may be formed on the hole transport layer 300 using the compound according to the present invention. In the present invention, the light-emission-assisting layer means a layer formed between the hole-transporting layer and the light-emitting layer and may be referred to as a second hole-transporting layer or a third hole-transporting layer.

In one embodiment of the present invention, cross-linking after the solution process can be accomplished by a curing process. The curing process may be formed by a reaction by heating, optionally in the presence of an initiator, or by UV, microwave, X-ray or electron beam irradiation.

For example, the heating method may be performed at a temperature of about 200 ° C for about 10 minutes to about 120 minutes, and more specifically, for about 20 to 60 minutes.

A light emitting layer material may be formed on the hole transport layer 300 or the light emitting auxiliary layer by vacuum deposition, thermal transfer, spin coating, nozzle printing, inkjet printing, slot coating, dip coating, The light emitting layer 400 can be formed by a solution process such as a screen printing process or a screen printing process. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The light emitting layer material may be a known compound as a host or a dopant. For example, R (red), G (green) and B (blue) of the light emitting layer 400 may be used as a solution process and B may be used as a superhybrid type used in a deposition process.

In one embodiment of the present invention, when two successive layers of, for example, a hole transporting layer and a luminescent auxiliary layer, a hole transporting layer and a luminescent layer or a luminescent auxiliary layer and a luminescent layer are laminated by a solution process, Since the insoluble layer is formed through the crosslinking reaction between the forming units, the resistance of the subsequent layer to the solvent can be improved when the subsequent layer is laminated by the solution process, and the uniformity and stability of the thin film can be improved through crosslinking.

When a phosphorescent dopant is used in the light emitting layer, a hole blocking material (HBL) may be further deposited by a vacuum deposition method or a solution process to prevent the triplet excitons or holes from diffusing into the electron transporting layer. The hole blocking material that can be used at this time is not particularly limited, but any known hole blocking material may be used. For example, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open Publication No. 11-329734 (A1) can be exemplified. Typically, Balq (bis Phenanthrolines based compounds such as UDC company BCP (bassocouroin), and the like can be used.

An electron transport layer 500 is formed on the light emitting layer 400 formed as described above. The electron transport layer may be formed by vacuum deposition, thermal transfer, spin coating, nozzle printing, inkjet printing, slot coating, Process, a roll-to-roll process, a doctor blading process, a screen printing process, or the like. The deposition conditions of the electron transporting layer depend on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer.

Thereafter, an electron injection layer material may be deposited on the electron transport layer 500 to form an electron injection layer 600. The electron injection layer may be formed by vacuum deposition, thermal transfer, Such as a coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, a screen printing process and the like.

The hole injecting layer 200, the hole transporting layer 300, the light emitting layer 400 and the electron transporting layer 500 of the organic light emitting diode can be formed using the compound according to the present invention or the following materials. The compound and a known substance can be used together.

A cathode 2000 for electron injection is formed on the electron injection layer 600 by a vacuum evaporation method or a sputtering method. As the cathode, various metals may be used. Specific examples thereof include aluminum, gold, and silver.

The organic light emitting device of the present invention can have an organic light emitting device having various structures as well as an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode structure, Layer or an intermediate layer of two layers may be further formed.

As described above, the thickness of each organic material layer formed according to the present invention can be controlled according to the required degree, specifically 10 to 1,000 nm, and more specifically, 20 to 150 nm.

In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.

The organic light emitting compound according to the present invention may be applied to all of the first and second aspects of the present invention, but the present invention is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited by these Examples.

[Example]

Synthetic example

The compound according to one embodiment of the present invention can be synthesized through the following reaction formula, but is not limited thereto.

[Reaction Scheme]

Hal = Halogen

Preparation Example 1: Synthesis of intermediate product

The synthesis process of the intermediate product is as follows, but is not limited thereto.

Intermediate Sub C1 Synthesis

10 g of 4'-vinylbiphenyl-4-amine (SMA), 8 g of 2-bromo-9,9-dimethyl-7-vinyl-9H-fluorene (SM B) _{BuONa 5.7 g, Pd 2 (dba} ) 3 0.9 g, P (t-Bu) ₃ were dissolved in 1.8 ml of toluene 100 ml and stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 12.5 g (yield: 81%) of an intermediate product Sub C1.

Intermediate products Sub C2 to Sub C9 synthesis

The intermediate products Sub C2 to Sub C9 were synthesized in the same manner as in Sub C1, as shown in Table 1, except that the starting materials SM A and SM B were different.

Intermediate Sub E1 synthesis

The synthesis process of the intermediate product Sub E1 is as follows, but is not limited thereto.

Was dissolved Sub C7 5 g, 4-Bromoiodobenzene 3 g, t-BuONa 3 g, Pd 2 (dba) 3 0.4 g, P (t-Bu) 3 0.8 ml round bottom flask in 50 ml of toluene was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain intermediate product Sub E1 (5.4 g, yield 71%).

Intermediate Sub E2 and Sub E3 synthesis

The starting materials Sub E2 and Sub E3 were synthesized as shown in Table 2,

Intermediate SM D1 synthesis

The synthesis process of the intermediate product SM D1 is as follows, but is not limited thereto.

To a round bottom flask was added 1-phenyl-3- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-Indole 9 g, 4-Bromoiodobenzene 9 g, K 2 CO 3 3 g of Pd (PPh ₃ ) _{4 and} 0.9 g of Pd (PPh ₃ ) ₄ were dissolved in 100 ml of 1,4-dioxane and 30 ml of distilled water, followed by stirring under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 5.2 g (yield: 71%) of the intermediate product SM D1.

Intermediate Sub D2 to Sub D7 Synthesis

The starting materials SM D2 to SM D7 were synthesized in the same manner as in Sub D1 as shown in Table 3 below

Preparation Example 2: Synthesis of the final product, Product P

The synthesis of the final product, Product P, may be synthesized, but is not limited to, the following scheme:

Final product Product P1 Synthesis

To a round bottom flask Sub C1 10 g, 3- (4- bromophenyl) -1H- indol-1-phenyl (SM D) 10.4 g, t -BuONa 3.9 g, Pd 2 (dba) 3 0.5 g, (t -Bu) ₃ P was dissolved in 80 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and purified by column and recrystallized to obtain 10.4 g of product P1 (yield: 64%).

m / z: 680.32 (100.0%), 681.32 (55.9%), 682.33 (15.2%), 683.33

Product P2 to Product P7 were synthesized in the same manner as Product P1 with starting materials Sub C and SM D as shown in Table 4 below.

Final product Product P8 Synthesis

5 g of Sub C6, 5.4 g of Sub E1, 1.9 g of t-BuONa, 0.3 g of Pd ₂ (dba) _{3 and} 0.5 ml of (t-Bu) ₃ P were dissolved in 40 ml of toluene and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 5.2 g (yield: 63%) of Product P8.

m / z: 1189.52 (100.0%), 1190.52 (95.0%), 1191.52 (44.4%), 1192.53 (13.9%), 1193.53

Final product Product P9 Synthesis

5 g of Sub C8, 5.4 g of Sub E2, 1.9 g of t-BuONa, 0.3 g of Pd ₂ (dba) _{3 and} 0.5 ml of (t-Bu) ₃ P were dissolved in 40 ml of toluene and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification and recrystallization to obtain 5 g of Product P9 (yield 62%).

m / z: 1185.49 (100.0%), 1186.49 (93.9%), 1187.49 (44.5%), 1188.50 (13.3%), 1189.50 (3.3%), 1186.48

Final product Product P10 Synthesis

10 g of Sub E3, 5.4 g of Sub D7, 2.9 g of t-BuONa, 0.6 g of Pd ₂ (dba) _{3 and} 1 ml of (t-Bu) ₃ P were dissolved in 40 ml of toluene, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, and purified and recrystallized from the column to obtain 6.4 g (yield: 51%) of Product P10.

m / z: 1603.70 (100.0%), 1602.70 (79.0%), 1604.70 (63.9%), 1605.71 (26.1%), 1606.71 (8.6%), 1607.71 (2.2% ), 1604.71 (1.0%)

Example 1: Preparation of organic light emitting device

A glass substrate coated with a thin film of indium tin oxide (ITO) was ultrasonically cleaned with a solvent such as distilled water, isopropyl alcohol, acetone, or methanol, dried and transferred to a plasma cleaner, and the substrate was cleaned for 5 minutes using oxygen plasma Respectively. Then, PEDOT: PSS was spin-coated on the ITO layer to a thickness of 50 nm using a spin coater on the ITO substrate. Then, the solvent was removed by drying on 150 hot plates for 10 minutes, and then the compound P1 of the present invention, which is a hole transporting material, was dissolved in xylene at 0.5 wt% and spin-coated to a thickness of 30 nm. Then, it was dried on 100 hot plates for 10 minutes and then crosslinked by heating for 200 to 30 minutes. A dopant DPAVBi was doped to the host material ADN as a light emitting layer on the hole transport layer at a ratio of 96: 4 and the solution was dissolved in 0.5 wt% of xylene to form a 30 nm thick spin coating layer. The resultant was dried on a hot plate of 100 minutes for 10 minutes, A film of ET01: Liq (1: 1) was formed to a thickness of 30 nm as an electron transfer layer using a thermal evaporator and then LiF 1 nm and aluminum (Al) 100 nm were formed. Encapsulation of the device was performed in a glove box, Respectively.

Examples 2 to 10: Preparation of organic light emitting device

An organic light emitting device having a hole transporting layer formed by using Product P2 to P10 instead of Product P1 was manufactured in the same manner as in Example 1.

Comparative Examples 1 to 8

An organic light emitting device was prepared by using the same method as in Example 1 except that the following Ref.1 to Ref.8 were used in place of Compound 1, respectively.

Experimental Example 1: Evaluation of performance of organic light emitting device

A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light emitting devices of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under atmospheric pressure. The results are shown in Table 5 below.

Op. V mA / cm2 Cd / A lm / w CIEx CIEy LT95 Comparative Example 1 6.85 10 3.50 1.87 0.140 0.112 30 Comparative Example 2 5.61 10 4.05 2.25 0.140 0.109 45 Comparative Example 3 5.35 10 4.89 2.97 0.140 0.109 87 Comparative Example 4 5.32 10 5.08 3.08 0.140 0.110 88 Comparative Example 5 5.32 10 5.10 3.11 0.140 0.109 80 Comparative Example 6 5.30 10 4.79 2.95 0.140 0.109 80 Comparative Example 7 5.37 10 4.56 2.80 0.140 0.111 82 Comparative Example 8 5.58 10 4.06 2.20 0.140 0.111 41 Example 1 4.91 10 6.43 3.97 0.140 0.109 129 Example 2 4.95 10 6.49 3.99 0.140 0.109 130 Example 3 4.94 10 6.42 3.93 0.140 0.110 128 Example 4 4.95 10 6.24 3.85 0.140 0.109 120 Example 5 4.91 10 6.20 3.81 0.140 0.109 123 Example 6 4.93 10 6.23 3.82 0.140 0.109 121 Example 7 4.91 10 6.38 3.89 0.140 0.109 139 Example 8 4.88 10 6.49 3.98 0.140 0.109 120 Example 9 4.89 10 6.42 3.97 0.140 0.109 131 Example 10 4.90 10 6.41 3.97 0.140 0.109 134

As shown in Table 5, the embodiments of the present invention can show the increase in efficiency and lifetime as compared with Comparative Examples 1 to 8.

More specifically, as compared with Comparative Example 1, Example 1 includes a crosslinking group forming agent, which results in crosslinking through a crosslinking step after forming a thin film, thereby increasing solvent resistance upon formation of a subsequent layer, thereby exhibiting a high efficiency long life. Compared with the comparative examples 2 to 5, it can be seen that the embodiments of the present invention show that the arylamine is substituted at the 3-position of the indole and exhibits a high efficiency and a long life-span effect. Compared with the comparative examples 6 to 7, the examples of the present invention show that the arylamine is substituted at the 3-position of the indole, showing higher efficiency than the carbazole. In comparison with Comparative Example 8, it can be seen that the embodiments of the present invention show high efficiency and long life by bonding an aryl group of N to indole. When an aryl group other than alkyl is bonded to N of the indole, stabilization of electrons of nitrogen to stabilize the structure of the compound can realize a long-life device.

Experimental Example 2: Solvent resistance test

Ref1 and Ref.2 and Ptoduct P1 to P10 of the present invention were respectively dissolved in xylene at 1 wt% and then spin-coated on the silicon wiper. 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. The initial thickness after crosslinking was measured, and 2 ml of xylene was dropped by a spin coater. After washing for 60 seconds at 2000 RPM, the solvent resistance was compared by comparing the thicknesses. The results are shown in Table 6.

Thickness after crosslinking Thickness after 1 wash of xylene Thickness after 2 times of xylene washing Insolubility degree Ref.1 50 nm 9 nm 2 nm 0.04 Ref.2 51 nm 33 nm 28 nm 0.55 P1 52 nm 49 nm 49 nm 0.94 P2 50 nm 48 nm 47 nm 0.94 P3 50 nm 48 nm 47 nm 0.94 P4 52 nm 49 nm 47 nm 0.90 P5 52 nm 48 nm 48 nm 0.92 P6 50 nm 49 nm 48 nm 0.96 P7 50 nm 48 nm 47 nm 0.94 P8 52 nm 49 nm 48 nm 0.92 P9 51 nm 49 nm 48 nm 0.94 P10 51 nm 49 nm 49 nm 0.96

As shown in Table 6, in the case of the compound of the present invention including a crosslinking group, crosslinking is performed through a crosslinking process after forming a thin film by a solution process, and the solvent resistance of the thin film is increased due to crosslinking. Therefore, It is possible to prevent the loss of the thin film when it is washed with the xylene used. That is, Ref. 1, the thickness of Product P1 to P10 was less than that of Ref. Compared with 2, Product P1 to P10 had a low loss rate because of high crosslinking probability. As shown in Table 3, it can be assumed that the film exhibits high efficiency and long life because it acts as a hole transport material while minimizing the loss of the thin film.

It will be understood by those of ordinary skill in the art that the foregoing description of the embodiments is for illustrative purposes and that those skilled in the art can easily modify the invention without departing from the spirit or essential characteristics thereof. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.

The scope of the present invention is defined by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be interpreted as being included in the scope of the present invention .

100: substrate
200: Hole injection layer
300: hole transport layer
400: light emitting layer
500: electron transport layer
600: electron injection layer
1000: anode
2000: cathode

Claims (22)

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

In Formula 1,
CL is hydrogen, an alkyl group or a crosslinked former of C ₁ ~ C _10,
R is hydrogen, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,
L is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,
n is an integer of 1 to 4, and when n is 2 or more, CL may be different from each other,
A ₁ is represented by the following general formula (1-1) or (1-2)

[Formula 1-1] [Formula 1-2]
In the above formula (1-1) or (1-2)
Ar ₁ to Ar ₃ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,
CL ₁ to CL ₃ are each independently a hydrogen or a crosslinking group,
L ₁ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,
A ₂ and A ₃ are each independently represented by the following formula 1-3 or 1-4,

[Chemical Formula 1-3] [Chemical Formula 1-4]
In the above formulas 1-3 or 1-4,
Ar ₄ to Ar ₆ each independently represent a substituted or unsubstituted C ₆ -C ₃₀ arylene group or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,
CL ₄ to CL ₆ are each independently a hydrogen or a crosslinking group,
L ₂ is a direct bond, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroarylene group,
The CL, CL ₁ to CL at least one of the former ₆ is a cross-linked, with the proviso that the A ₁ is represented by the above formula 1-1, CL _1, this cross-linking the former and CL CL CL ₄ to ₆ of At least one is a crosslinking group. The method according to claim 1,
Wherein said compound is represented by the following formula (2).
(2)

The method according to claim 1,
Wherein said compound is represented by the following general formula (3) or (4).
(3)

[Chemical Formula 4]

In Formula 3 or Formula 4,
The two Ar ₄ may be the same or different. In addition, the two CL ₄ may be the same or different from each other. The method according to claim 1,
Wherein said compound is represented by the following formula (5) or (6).
[Chemical Formula 5]

[Chemical Formula 6]

The method according to claim 1,
Wherein said compound is represented by the following formula (7) or (8).
(7)

[Chemical Formula 8]

In Formula 7 or Formula 8,
The two Ar _{5 s} may be the same or different and the two Ar _{6 s} may be the same or different. In addition, the two CL ₅ may be the same or different from each other, two CL ₆ may be the same or different from each other. The method according to claim 1,
Wherein CL and CL < _{1 >} are both hydrogen. The method according to claim 1,
Wherein L, L &_lt; ₁ &_gt; and L < ₂ > are each independently phenyl or biphenyl. The method according to claim 1,
Wherein the compound has two or more crosslinking groups. The method according to claim 1,
And at least two of the above-mentioned CL ₄ to CL ₆ are crosslinking-forming groups. The method according to claim 1,
Wherein the crosslinking group is represented by any one of the following structural formulas.

In the above formula,
Y is a direct bond, a substituted or unsubstituted C ₁ -C ₁₈ alkyl group, a substituted or unsubstituted C ₆ -C ₁₈ arylalkyl group, a substituted or unsubstituted C ₂ -C ₁₈ alkenyl group, of a C ₁ ~ C ₁₈ alkoxy group, a substituted or unsubstituted C ₃ ~ C ₁₈ of octanoic seten group, a substituted or unsubstituted C ₃ ~ C ₁₈ acetate group, a substituted or unsubstituted C ₃ ~ C ₁₈ rings of A substituted or unsubstituted C ₃ -C ₁₈ aryloxy group, a substituted or unsubstituted C ₃ -C ₁₈ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₁₈ aryl group, or a substituted or unsubstituted C ₃ -C ₁₈ aryloxy group, An unsubstituted C ₃ to C ₁₈ carbonyl group, and a dotted line is a bonding position. The method according to claim 1,
Ar ₁ to Ar ₆ each independently represents a substituted or unsubstituted phenyl, biphenyl, terphenyl, dimethylfluorene, dibenzofuran, dibenzothiophene, naphthyl, diphenylfluorene, spirobifluorene And combinations thereof. The method according to claim 1,
Wherein the compound represented by Formula 1 comprises any one of the following compounds.

A polymer formed by the compound represented by the general formula (1) as set forth in claim 1. A compound represented by formula (1) as set forth in claim 1; And
A solvent having a boiling point of 100 to 400 DEG C and a viscosity of 0.1 to 15 cP. 15. The method of claim 14,
The solvent is selected from the group consisting of o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2- chlorobenzotrifluoride, dimethylformamide, Fluoroanisole, 3-trifluoromethyl anisole, 2-methyl anisole, 2-fluoroanisole, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, 2-fluorobenzonitrile, 4-fluororubberatol, 2,6-dimethyl anisole, 3- (4-fluorobenzonitrile) Fluorobenzonitrile, 2,5-dimethyl anisole, 2,4-dimethyl anisole, benzonitrile, 3,5-dimethyl anisole, N, N-dimethylaniline, 1-fluoro-3,5-dimethoxy Benzene, N-methylpyrrolidinone, 3-fluorobenzotrifluoride, benzotrifluoride, dioxane, trifluoromethoxybenzene, 4-fluorobenzotrifluoride, 3-fluoropyridine, toluene, 2 - fluorotoluene, 2-fluorobenzoate Trifluoro-toluene, 1-chloro-2,4-difluorobenzene, 2-fluoropyridine, 3-chloropyridine, Fluorobenzene, 1-chloro-2,5-difluorobenzene, 4-chlorofluorobenzene, chlorobenzene, 2- chlorofluorobenzene, 3-phenoxytoluene, 1- tetralone, acetophenone, 2-phenoxy-2H-pyran, 1,2-dimethoxy-4- (1-propenyl) phenol, benzophenone, isophorone, butoxygen, benzyl butyl ether, p- anisaldehyde dimethyl acetal, tetrahydro- Benzene, 1,4-benzodioxane, 1,3-dipropoxybenzene, 2,5-dimethoxytoluene, 4-ethylphenetol, 1,2,4-trimethoxybenzene, 4- Phenyl-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butyl anisole, trans- Dimethoxybenzene, phenetole, 2-methoxy toluene, 3-methoxy toluene, 2,2-dimethyl-1 , 3-benzodioxole, 4-methoxytoluene, benzyl methyl ether, 1,8-cineol, allylphenyl ether, 2,3-dihydro-2-methylbenzofuran, 2,3-dihydrobenzofuran, But are not limited to, 3,5-dimethyl anisole, 2,5-dimethyl anisole, 4-ethyl anisole, 2-ethyl anisole, 1,2-methylenedioxybenzene, p- A composition for forming an organic layer of an organic light emitting element, 15. The method of claim 14,
Wherein the solvent has a boiling point of more than 200 and a viscosity of less than 10 cP. 15. The method of claim 14,
Wherein the solvent comprises a solvent blend in which two or more solvents are mixed. 18. The method of claim 17,
Wherein the solvent blend comprises a first solvent having a boiling point of greater than 200 and a viscosity of less than 10 cP and a second solvent having a boiling point lower than that of the first solvent. An organic light-emitting device comprising an organic material layer containing a polymer formed of a compound represented by the general formula (1) described in claim 1 between a first electrode and a second electrode. 20. The method of claim 19,
Wherein the polymer comprises an organic material layer containing any one of the following repeating units.

20. The method of claim 19,
Wherein the organic material layer is one or more layers of a hole injecting layer, a hole transporting layer, and a light emitting auxiliary layer. 22. The method of claim 21,
Wherein the organic layer comprises a polymer layer having an insolubility degree of 0.6 to 1 as defined by the following formula.
Degree of insolubility = thickness after washing with organic solvent after crosslinking (B) / thickness (A) of initial thin film after crosslinking

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