KR20190054422A - Polymer, coating composition comprising the same, organic light emitting device using the same and method of manufacturing the same - Google Patents

Abstract

The present invention relates to a polymer containing a repeat unit of chemical formula 1; a coating composition comprising the same, an organic light-emitting device using the same, and a method of producing the same. According to an embodiment of the present invention, the polymer may be subjected to a solvent process, and thus may enable surface enlargement of a device and may be used as a material of an organic layer of the organic light-emitting device.

Description

TECHNICAL FIELD [0001] The present invention relates to a polymer, a coating composition containing the same, an organic light emitting device using the same, and a method for manufacturing the same. [0002]

TECHNICAL FIELD The present invention relates to a polymer, a coating composition comprising the polymer, an organic light emitting device formed using the coating composition, and a method of manufacturing the same.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between the anode and the cathode, electrons and holes are injected into the organic layer from the cathode and the anode, respectively, when an electric current is applied between the two electrodes. Electrons and holes injected into the organic layer are recombined to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

Conventionally, a deposition process has been mainly used for manufacturing an organic light emitting device. However, there is a problem that a material loss is generated much when the organic light emitting device is manufactured by a deposition process. In order to solve this problem, a technique of manufacturing a device through a solution process which can increase production efficiency due to low material loss And development of a material that can be used in a solution process is required.

Materials used in organic light emitting devices for solution processes should have the following properties.

First, it should be able to form a homogeneous solution that is excellent in solubility in a solvent and is storable. In the case of commercially available materials for the deposition process, since the crystals are easily dissolved in the solution or the crystals are easily caught even when the solution is formed, the concentration gradient of the solution changes depending on the storage period or the possibility of forming a defective device is high.

Second, the layers of the solution process must have resistance to the solvent and the material used in the process of forming the other layers, have excellent current efficiency in the production of the organic light emitting device, and have excellent lifetime characteristics.

Korean Patent Laid-Open Publication No. 2016-094362

It is an object of the present invention to provide a polymer usable in an organic light emitting device for a solution process, a coating composition comprising the polymer, an organic light emitting device including the coating composition, and a method of manufacturing the organic light emitting device.

The present invention provides a polymer comprising a repeating unit represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 is a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

R is hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -L < 2 > -Ar <

L2 is a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

Ar 1 is a functional group capable of crosslinking by heat or light,

n1 to n4 are each an integer of 0 to 4,

n is an integer of 0 to 8,

When n and n1 to n4 are each 2 or more, the substituents in the parentheses are the same or different from each other.

The present disclosure provides coating compositions comprising the polymeric polymers.

The disclosure also relates to a light emitting device comprising: a first electrode; A second electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the coating composition or a cured product thereof.

Finally, the present disclosure provides a method of manufacturing a semiconductor device, comprising: preparing a substrate; Forming a first electrode on the substrate; Forming at least one organic layer on the first electrode; And forming a second electrode on the organic material layer, wherein the forming the organic material layer includes forming one or more organic material layers using the coating composition. do.

The polymer according to one embodiment of the present invention can be subjected to a solution process, enabling the device to have a large area, and can be used as a material for an organic material layer of an organic light emitting device. In addition, the polymer of the present invention is excellent in solubility in a solvent, is excellent in resistance to a solution used in a process for forming other layers, is excellent in current efficiency, excellent in current efficiency, The device can be manufactured.

1 shows an example of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, the present specification will be described in detail.

One embodiment of the present invention provides a polymer comprising a repeating unit represented by formula (1).

[Chemical Formula 1]

In Formula 1,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 is a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

R is hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -L < 2 > -Ar <

L2 is a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

Ar 1 is a functional group capable of crosslinking by heat or light,

n1 to n4 are each an integer of 0 to 4,

n is an integer of 0 to 8,

When n and n1 to n4 are each 2 or more, the substituents in the parentheses are the same or different from each other.

Since the hole transporting layer located between the hole injection layer and the light emitting layer of the organic light emitting device does not have a high charge mobility, it must be thinly coated. In order to form a thin and uniform film, the solubility and coating property should be excellent. Polymers with excellent coating properties are advantageous. The polymer according to an embodiment of the present invention includes a fluorene structure and an amine structure and is capable of forming a uniform film when applied to a hole transport layer of an organic light emitting device rather than a monomolecule containing a fluorene structure and an arylamine structure, Is improved.

In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

In this specification, the term " combination thereof " included in the expression of the machine form means a combination of two or more states selected from the group consisting of constituent elements described in the expression of the machine form, Quot; means that two or more members selected from the group consisting of elements are included.

As used herein, the term " repeating unit " means a repeating structure contained in a monomer of a polymer, wherein the monomer is bonded to the polymer by polymerization.

In this specification, the meaning of "including a repeating unit" means that it is included in the main chain in the polymer.

In one embodiment of the present invention, the polymer containing the repeating unit represented by the formula (1) is preferably a compound having solubility in a suitable organic solvent.

In addition, in the case of the polymer according to one embodiment of the present invention, the organic light emitting device can be manufactured by the solution coating method, and the device can be made larger.

Hereinafter, the substituent of the present specification will be described in detail.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Quot; refers to a moiety bonded to another substituent or bond.

In the present specification, the term " substituted " means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, When two or more substituents are substituted, two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; -CN; An alkyl group; An alkoxy group; A cycloalkyl group; An aryl group; And heteroaryl groups, or substituted or unsubstituted with a substituent to which at least two of the above exemplified substituents are connected. For example, the "substituent group to which at least two substituents are connected" may be a phenyl group substituted with a hexyl group.

In this specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30. According to one embodiment, the alkyl group may have 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert- , tert-pentyl group, n-hexyl group, isohexyl group, n-heptyl group, n-octyl group and the like.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is 1 to 40 carbon atoms and, according to one embodiment, has 1 to 20 carbon atoms. Specifically, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a tert-butoxy group, a n-pentyloxy group, a n-hexyloxy group, But is not limited thereto.

Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

In the present specification, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기), 9,9-디옥틸플루오레닐기 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), a 9,9-dioctylfluorenyl group, and other substituted fluorenyl groups. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, a dibenzofuranyl group and a dibenzothiophenyl group. The present invention is not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.

In the present specification, the description of the aforementioned alkyl group is applied, except that the alkylene group is a divalent group.

In this specification, the description of the aryl group described above applies, except that the arylene group is a divalent group.

According to one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another embodiment, L1 is a direct bond; A substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, L1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another embodiment, L < 1 > is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L < 1 > is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; Or a substituted or unsubstituted naphthylene group.

According to another embodiment, L < 1 > is an arylene group having 6 to 30 carbon atoms.

In another embodiment, L < 1 > is selected from the group consisting of a phenylene group; Biphenyllylene groups; A terphenylene group; Or a naphthylene group.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2).

(2)

In Formula 2,

The definitions of R1 to R4, R and n1 to n4 are the same as those in the above formula (1)

n11 is an integer of 0 to 5, and when n11 is 2 or more, Rs are the same or different from each other.

And n11 is an integer of 0 to 2.

According to another embodiment, n11 is 1 or 2.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (3) or (4).

(3)

[Chemical Formula 4]

In the above formulas (3) and (4)

The definitions of R1 to R4 and n1 to n4 are the same as those in Formula 1,

R11 to R13 are the same as or different from each other and each independently have the same definition as R in the above formula (1).

According to one embodiment of the present invention, n1 to n4 are integers of 0 to 2, respectively.

According to one embodiment of the present invention, R1 to R4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In one embodiment of the present invention, R 1 to R 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, R1 to R4 are hydrogen.

According to one embodiment of the present disclosure, R is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted C2-C60 heteroaryl group; Or -L2-Ar1.

In another embodiment, R is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted C2-C30 heteroaryl group; Or -L2-Ar1.

According to another embodiment, R is a substituted or unsubstituted alkyl group; Or -L2-Ar1.

In another embodiment, R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or -L2-Ar1.

According to another embodiment, R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or -L2-Ar1.

In another embodiment, R is a substituted or substituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted heptyl group; A substituted or unsubstituted octyl group; A substituted or unsubstituted nonyl group; Or -L2-Ar1.

According to another embodiment, R is a methyl group, an ethyl group, a propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; Hexyl group; A heptyl group; Octyl group; Nonyl; Or -L2-Ar1.

According to one embodiment of the present disclosure, n is an integer from 1 to 8, and n is an integer from 1 to 5, according to one example. R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, and when n falls within the above range, the solubility of the polymer increases.

According to one embodiment of the present disclosure, L2 is a direct bond; A substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another embodiment, L2 is a direct bond; A substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another embodiment, L2 is a substituted or unsubstituted alkylene group.

In another embodiment, L2 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

According to another embodiment, L2 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In another embodiment, L2 is a substituted or substituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted heptyl group; A substituted or unsubstituted octyl group; Or a substituted or unsubstituted nonyl group.

According to another embodiment, L2 represents a methyl group, an ethyl group, a propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; Hexyl group; A heptyl group; Octyl group; Or a nonyl group.

According to one embodiment of the present disclosure, Ar1 is a functional group capable of crosslinking by heat or light. When the R includes a functional group capable of crosslinking by heat or light, a layer having a higher hardness can be formed in the production of an organic light emitting device, and therefore resistance to solvents forming other layers is increased.

The functional group capable of crosslinking by heat or light may be any one of the following structures.

In the above structure,

X1 is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

According to one embodiment of the present disclosure, X1 is hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted pentyl group; Or a substituted or unsubstituted hexyl group.

According to another embodiment, X1 is hydrogen; Methyl group; An ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; Or a hexyl group.

According to one embodiment of the present disclosure, Ar1 is any one of the following structures.

According to one embodiment of the present invention, R11 to R13 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted C2-C60 heteroaryl group; Or -L2-Ar1.

In another embodiment, R11 to R13 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted C2-C30 heteroaryl group; Or -L2-Ar1.

According to another embodiment, R11 to R13 are the same or different and are each independently a substituted or unsubstituted alkyl group; Or -L2-Ar1.

In another embodiment, R11 to R13 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or -L2-Ar1.

According to another embodiment, R11 to R13 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or -L2-Ar1.

In another embodiment, R11 to R13 are the same or different and are each independently a substituted or substituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted heptyl group; A substituted or unsubstituted octyl group; A substituted or unsubstituted nonyl group; Or -L2-Ar1.

According to another embodiment, R11 to R13 are the same or different from each other, and each independently represents a methyl group, an ethyl group, a propyl group; Isopropyl group; Butyl group; tert-butyl group; Pentyl group; Hexyl group; A heptyl group; Octyl group; Nonyl; Or -L2-Ar1.

According to one embodiment of the present disclosure, in the definition of R11 to R13, L2 and Ar1 are as described above.

According to one embodiment of the present invention, the polymer includes a unit represented by the following formula (5).

[Chemical Formula 5]

In Formula 5,

R 1 to R 4, R, n and n 1 to n 4 have the same meanings as in the above formula (1)

m is an integer of 3 or more and 3,000 or less.

According to one embodiment of the present disclosure, the terminal group of the polymer may be a substituted or unsubstituted aryl group, but is not limited thereto.

According to another embodiment, the terminal group of the polymer may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, but is not limited thereto.

In another embodiment, the terminal group of the polymer may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, but is not limited thereto.

According to another embodiment, the terminal group of the polymer is selected from the group consisting of a halogen group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

According to another embodiment, the terminal group of the polymer is a phenyl group substituted or unsubstituted with a halogen group or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A halogen group, or a substituted or unsubstituted naphthyl group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted fluorenyl group substituted with a halogen group or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or an anthracenyl group substituted or unsubstituted with a halogen group or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, but is not limited thereto.

In another embodiment, the terminal group of the polymer is a phenyl group substituted or unsubstituted by fluorine, a tert-butyl group or a trifluoromethyl group.

According to another embodiment, the terminal group of the polymer is a phenyl group; 4-tert-butylphenyl group; Or a 4-trifluoromethylphenyl group.

According to one embodiment of the present invention, the polymer may include units represented by any one of the following formulas (5-1) to (5-4).

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

In the formulas (5-1) to (5-4)

and m is an integer of 3 to 3,000.

The polymer according to one embodiment of the present invention can be produced by a production method described below. For example, the polymer may be produced in the same manner as in the method for producing a polymer of the specific embodiment described below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

When a polymer is produced by purchasing / producing a repeating unit having a structure other than a fluorene-based repeating unit in the method for producing a polymer in a specific example to be described later, a polymer having another structure can be produced.

In one embodiment of the present disclosure, the coating composition comprises the polymer and the solvent.

In one embodiment of the present invention, the coating composition may further comprise a polymer compound. When the coating composition further comprises a polymer compound, the ink property of the coating composition can be enhanced. That is, the coating composition further comprising the polymer compound may provide a suitable viscosity for coating or ink jetting.

According to one embodiment of the present disclosure, the above-mentioned polymers may have a number average molecular weight of from 3,000 g / mol to 10,000,000 g / mol or less. According to another example, it can be from 10,000 g / mol to 1,000,000 g / mol or less. When the polymer falls within the above-mentioned molecular weight range, the OLED has an advantage in that it has excellent performance and lifetime, and has a solubility sufficient for solution processing.

In one embodiment of the present disclosure, the coating composition may be in a liquid phase. The " liquid phase " means that the liquid phase is at normal temperature and pressure.

In one embodiment of the present invention, the solvent includes, for example, chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; Examples of polyhydric alcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, Alcohols and their derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethylsulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; A solvent such as tetralin may be exemplified, but a solvent capable of dissolving or dispersing the polymer according to one embodiment of the present invention is sufficient, and the solvent is not limited thereto.

In another embodiment, the solvents may be used alone or in combination of two or more solvents.

In another embodiment, the viscosity of the coating composition is from 2 cP to 15 cP, more preferably from 3 cP to 10 cP. When the viscosity is satisfied, it is easy to manufacture the device.

The present disclosure also provides an organic light emitting device formed using the coating composition.

In one embodiment of the present disclosure, the first electrode; A second electrode; And at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes the coating composition or a cured product thereof.

In one embodiment of the present invention, the organic compound layer comprising the coating composition or a cured product thereof is a hole transporting layer or a hole injecting layer.

According to another embodiment, the organic compound layer comprising the coating composition or a cured product thereof is a hole transport layer.

In one embodiment of the present invention, the organic compound layer including the coating composition or a cured product thereof is a light emitting layer.

In one embodiment of the present invention, the organic light emitting element is a green organic light emitting element in which the light emitting layer includes the polymer.

In one embodiment of the present invention, the organic light emitting element is a red organic light emitting element in which the light emitting layer includes the polymer.

In one embodiment of the present invention, the organic light emitting element is a blue organic light emitting element in which the light emitting layer includes the polymer.

In one embodiment of the present invention, the organic light emitting device includes a hole injecting layer, a hole transporting layer, a layer simultaneously transporting holes and holes, an electron transporting layer, an electron injecting layer, a layer simultaneously carrying electrons and electrons, Layer and a hole blocking layer.

In one embodiment of the present disclosure, the first electrode is an anode and the second electrode is a cathode.

According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic compound layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a hole injecting layer, a hole transporting layer, a layer simultaneously injecting or transporting holes, a light emitting layer, an electron transporting layer, an electron injecting layer, Structure. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

According to one example of the organic light emitting device of the present invention, the anode, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer, and the cathode may be stacked in this order.

According to another example of the organic light emitting device, the anode, the hole injection layer, the hole transport layer, the light emitting layer, the layer carrying the electron transport and the electron injection simultaneously, and the cathode may be stacked in this order.

According to an example of the organic light emitting device of the present invention, the layers may be stacked in this order: [layer for simultaneously performing anode / hole injection and hole transporting / light emitting layer / electron transporting layer / electron injecting layer / cathode].

According to another example of the organic light emitting device, the layers may be stacked in this order: [layer for simultaneous anode / hole injection and hole transport / light emitting layer / layer for simultaneous electron transport and electron injection / cathode].

For example, the structure of an organic light emitting device according to one embodiment of the present specification is illustrated in FIG.

1, an anode 201, a hole injecting layer 301, a hole transporting layer 401, a light emitting layer 501, a layer 601 that simultaneously transports electrons and electrons, and a cathode 701 are formed on a substrate 101 A structure of an organic light emitting device sequentially stacked is illustrated.

FIG. 1 illustrates an organic light emitting device and is not limited thereto.

When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

The organic light emitting device in this specification includes a polymer in which at least one layer of the organic material layer contains a repeating unit represented by the formula (1), and the repeating unit is contained in an amount of more than 0 mol% and 20 mol% May be prepared by materials and methods known in the art, except that they are formed using coating compositions.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer thereon by a solution process, a deposition process, or the like, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

According to one embodiment of the present invention, the organic light emitting device of the present invention comprises the repeating unit represented by the above formula (1) in one or more organic layers of the organic light emitting device, wherein the repeating unit is present in an amount of more than 0 mol% % Or less can be formed by spin coating or printing, and the organic layer not containing the polymer can be formed by spin coating, printing, or vapor deposition .

The present disclosure also provides a method of manufacturing an organic light emitting device formed using the coating composition.

Specifically, in one embodiment of the present disclosure, there is provided a method comprising: preparing a substrate; Forming a first electrode on the substrate; Forming at least one organic layer on the first electrode; And forming a second electrode on the organic material layer, wherein forming the organic material layer includes forming at least one organic material layer using the coating composition.

In one embodiment of the present disclosure, the organic layer formed using the coating composition is formed using a solution process.

In one embodiment of the present invention, the organic layer formed using the coating composition is formed using spin coating.

In another embodiment, the organic layer formed using the coating composition is formed by a printing method.

In the state of the present specification, the printing method includes, but is not limited to, ink jet printing, nozzle printing, offset printing, transfer printing, or screen printing.

The coating composition according to one embodiment of the present invention is suitable for a solution process because of its structural characteristics and can be formed by spin coating, so that it is economically effective in time and cost in manufacturing a device.

In one embodiment of the present disclosure, the step of forming an organic layer formed using the coating composition comprises: coating the coating composition on the first electrode; And heat treating or light treating the coated coating composition.

According to another embodiment, the heat treatment or light treatment may be performed in an N ₂ atmosphere or air, but is not limited thereto.

According to one embodiment of the present invention, the heat treatment or light treatment may be performed through heat treatment, and the heat treatment temperature may be 85 to 250 ° C, and may be 100 to 250 ° C depending on an operating condition. In one embodiment, it may be between 100 ° C and 200 ° C.

In another embodiment, the heat treatment time in the step of heat treatment and heat treatment or light treatment may be from 1 minute to 2 hours, and from 1 minute to 1 hour according to one implementation state. In another embodiment, , 5 minutes to 30 minutes.

As the anode material, a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from the electrode. The hole injecting layer has a hole injecting effect for hole injecting effect on the anode, a hole injecting effect for the light emitting layer or the light emitting material due to its ability to transport holes to the hole injecting material, A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer as the hole transport material. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injecting layer is a layer for injecting electrons from the electrode. The electron injecting layer has an ability to transport electrons as an electron injecting material, has an electron injecting effect from the cathode, an excellent electron injecting effect to the light emitting layer or the light emitting material, A compound which prevents migration of excitons to the hole injection layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer is a layer which prevents the cathode from reaching the hole, and can be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Synthetic example >

Synthetic example  1. Preparation of polymer 1

1) Intermediate ( 1) of  Produce

Intermediate (1) is prepared according to Lindner, Marcin et al, Chemistry - A European Journal, 22 (37), 13218-13235; 2016 as a reference.

2) Intermediate ( 2) of  Produce

Intermediate (2) is commercially available from Joosten, Dominik et al, PCT Int. Appl., 2016184540, 24 Nov 2016.

3) Intermediate ( 3) of  Produce

Tert-butyl hydroperoxide (4.24 g, 47.1 mmol) and 50 mL of dimethylformamide [DMF] were placed in a 250 mL three-necked flask equipped with a stirrer, Lt; / RTI &gt; The temperature was then lowered to room temperature, diluted with ethyl acetate, and washed several times with water. The organic layer was extracted with MgSO ₄ , the solvent was removed, and the residue was subjected to column chromatography with silica gel. The NMR data value of the intermediate (3) is as follows.

_{1H NMR (400 MHz, CDCl 3} ) d: 8.06 (br, s, 1H), 7.86 (d, J ¼ 7.4 Hz, 2H), 7.57 (d, J ¼ 8.3 Hz, 2H), 7.53-7.51 (m, 1H), 7.47-7.43 (m, 2H), 7.23-7.21 (m, 2H), 2.95-2.88 (m, 1H), 1.27 (d, J = 6.9 Hz, 6H); 13 C NMR (100 MHz, CDCl 3) d: 165.87, 145.30, 135.56, 135.01, 131.63, 128.64, 127.01, 126.88, 120.54, 33.58, 23.96.

4) Intermediate ( 4) of  Produce

A mixture of Intermediate 3 (1.19 g, 5 mmol), CuBr ₂ (0.111 g, 0.5 mmol), Cs ₂ CO ₃ (3.26, 10 mmol), N, N'- dimethylethanediamine , 2 mmol) and anhydrous toluene (20 mL) were placed in a sealed tube and the intermediate (2) (2.38 g, 5 mmol) was added under N ₂ atmosphere and reacted at 130 ° C. for 24 hours. The temperature was lowered to room temperature, diluted with ethyl acetate [ethyl acetate], and washed several times with water. The organic layer was separated, the water was removed with Na ₂ SO ₄ , the solvent was removed, and the residue was subjected to column chromatography using silica gel.

5) Intermediate ( 5) of  Produce

In a nitrogen atmosphere, Fe (catalytic amount) was dissolved in 15 mL of tetrahydrofuran [THF] and K ₃ PO ₄ (0.066 g, 0.32 mmol) was added. Thereafter, Intermediate 4 (1 g, 1.57 mmol) was added, sealed, H ₂ was added, and the reaction was allowed to proceed at 130 ° C for 3 hours. After lowering the temperature to -78 ° C, it was ventilated, diluted with ethyl acetate [ethyl acetate], and washed several times with water. The organic layer was separated, the water was removed with Na ₂ SO ₄ , the solvent was removed, and the residue was subjected to column chromatography using silica gel.

6) Preparation of Polymer 1

(0.5 g, 0.942 mmol), sodium tertbutoxide (0.45 g, 4.71 mmol) and Pd (PtBu ₃ ) ₂ (catalytic amount) were placed in a round flask and 20 mL of toluene [toluene] Lt; / RTI &gt; The mixture was filtered and then washed with methanol, water, ethanol, hexane, dissolved in methylene chloride, charcoal, and MgSO ₄ were added to the reaction mixture for 30 minutes The mixture was stirred at room temperature. The stirred mixture was passed through silica treated with triethylamine, and methylene chloride was removed. The residue was dissolved in a small amount of toluene and adsorbed on silica treated with triethylamine. Then, the reaction mixture was added dropwise to the column, washed with hexane, and then dissolved in toluene to remove toluene. Part of the toluene was removed, precipitated in methanol, filtered and dried to obtain Polymer 1 . At this time, the number average molecular weight was measured to confirm that Polymer 1 was prepared, and the number average molecular weight of Polymer 1 was 24,000 g / mol.

2. Preparation of Polymer 2

1) Intermediate (3- 1) of  Produce

Intermediate (3-1) was prepared in the same manner as in the preparation of Intermediate (3) except that 3B was used instead of 3A in the preparation of Intermediate (3).

2) Intermediate (4- 1) of  Produce

Intermediate (4-1) was prepared in the same manner as in the preparation of intermediate (4) except for using intermediate (3-1) instead of intermediate (3) in the production of intermediate (4).

3) Intermediate (5- 1) of  Produce

Intermediate (5-1) was prepared in the same manner as in the preparation of intermediate (5) except that intermediate (4-1) was used instead of intermediate (4) in the preparation of intermediate

4) Preparation of polymer 2

Polymer 2 was prepared in the same manner as in the production of Polymer 1, except that Intermediate (5-1) was used instead of Intermediate (5) in the production of Polymer 1. [ At this time, the number average molecular weight was measured to confirm that Polymer 2 was prepared, and the number average molecular weight of Polymer 2 was 89,000 g / mol.

3. Preparation of Polymer 3

1) Intermediate (3- 2) of  Produce

Intermediate (3-2) was prepared in the same manner as in the preparation of Intermediate (3) except that 3C was used instead of 3A in the preparation of Intermediate (3).

2) Intermediate (4- 2) of  Produce

Intermediate (4-2) was prepared in the same manner as in the preparation of Intermediate (4) except that Intermediate (3-2) was used instead of Intermediate (3) in the preparation of Intermediate (4).

3) Intermediate (5- 2) of  Produce

Intermediate (5-2) was prepared in the same manner as in the preparation of intermediate (5) except for using intermediate (4-2) instead of intermediate (4) in the production of intermediate (5).

4) Preparation of polymer 3

Polymer 3 was prepared in the same manner as in the production of Polymer 1, except that Intermediate (5-2) was used instead of Intermediate (5) in the preparation of Polymer 1. [ At this time, the number average molecular weight was measured to confirm that Polymer 3 was prepared, and the number average molecular weight of Polymer 3 was 81,000 g / mol.

4. Preparation of polymer 4

1) Intermediate (3- 3) of  Produce

Intermediate (3-3) was prepared in the same manner as in the preparation of Intermediate (3) except that 3D was used instead of 3A in the preparation of Intermediate (3).

2) Intermediate (4- 3) of  Produce

Intermediate (4-3) was prepared in the same manner as in the preparation of intermediate (4) except that intermediate (3-3) was used instead of intermediate (3) in the preparation of intermediate (4).

3) Intermediate (5- 3) of  Produce

Intermediate (5-3) was prepared in the same manner as in the preparation of intermediate (5) except for using intermediate (4-3) instead of intermediate (4) in the production of intermediate (5).

4) Preparation of Polymer 4

Polymer 4 was prepared in the same manner as in the production of Polymer 1, except that Intermediate (5-3) was used instead of Intermediate (5) in the production of Polymer 1. [ The number average molecular weight of the polymer 1 was 95,000 g / mol.

< Example / Comparative Example >

Example  One.

The glass substrate on which ITO (indium tin oxide) was deposited to a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing with isopropyl alcohol and acetone solvent was performed for 30 minutes each, followed by UV ozone treatment.

PEDOT: PSS (Clevios P VP CH8000) was spin-coated on the prepared ITO transparent electrode at 2000 rpm for 30 seconds and then heat-treated at 200 ° C for 10 minutes to form a film with a thickness of 70 nm. After transferring to a glove box, Polymer 1 was dissolved in toluene in an amount of 0.7 wt% and spin-coated on the hole injecting layer to form a film having a thickness of 200 ANGSTROM. The film was heated at 200 DEG C for 30 minutes under a nitrogen atmosphere to form a hole transporting layer. Thereafter, the compound was transferred to a vacuum evaporator, and then Compound 2 and Compound 3 shown below were vacuum deposited on the hole transport layer to a thickness of 300 Å at a concentration of 8 wt% to form a light emitting layer. Compound 4 was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer. Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and a thickness of 2000 Å to form a cathode.

Was maintained at the deposition rate 0.4 ~ 0.7Å / sec for organic material in the above process, the cathode of LiF was 0.3Å / sec, aluminum was deposited at a rate of 2Å / sec, the degree of vacuum upon deposition 2x10 ^-7 ~ 5x10 ^{- 8} torr was maintained.

Thereafter, sealing was performed by bonding the sealing glass and the glass substrate to the glass using a photo-curable epoxy resin to prepare an organic light emitting device having a multilayer structure. Subsequent operations were performed at room temperature (25 캜) in the atmosphere.

[Compound 1] [Compound 2]

[Compound 3] [Compound 4]

Example  2.

An organic light emitting device was prepared in the same manner as in Example 1 except that Polymer 2 prepared in Synthesis Example 2 was used instead of Polymer 1 in Example 1.

Example  3.

An organic light emitting device was prepared in the same manner as in Example 1 except that Polymer 3 prepared in Synthesis Example 3 was used instead of Polymer 1 in Example 1.

Example  4.

An organic light emitting device was prepared in the same manner as in Example 1 except that Polymer 4 prepared in Synthesis Example 4 was used instead of Polymer 1 in Example 1.

Comparative Example  One.

An organic light emitting device was prepared in the same manner as in Example 1, except that the following Polymer 1 was used instead of Polymer 1 in Example 1. The following Comparative Polymer 1 has a number average molecular weight of 18,000 g / mol.

[Comparative Polymer 1]

The voltage, efficiency, and lifetime (T80) of the organic light emitting devices manufactured in Examples 1 to 4 and Comparative Example 1 were measured, and the time to reach 80% of the initial luminance at a current density of 10 mA / cm ² was measured. The results are shown in Table 1 below.

Voltage (V)
(10 mA / cm ² _-) Cd / A QE (%) T80 Example 1 3.96 1.62 1.01 15 Example 2 4.19 3.42 3.70 40 Example 3 3.67 5.44 5.86 62 Example 4 3.66 5.21 5.66 67 Comparative Example 1 11.8 0.72 0.32 2

From Table 1, it can be confirmed that Examples 1 to 4 of the present invention are connected by conjugation, but the driving voltage, efficiency, and lifetime characteristics are superior to Comparative Example 1 using Comparative Polymer 1 that does not contain an amine.

101: substrate
201: anode
301: Hole injection layer
401: hole transport layer
501: light emitting layer
601: layer simultaneously carrying electron transport and electron injection
701: Cathode

Claims (15)

1. A polymer comprising a repeating unit represented by the following formula (1): &lt; EMI ID =
[Chemical Formula 1]

In Formula 1,
R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 is a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
R is hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or -L &lt; 2 &gt; -Ar &lt;
L2 is a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
Ar 1 is a functional group capable of crosslinking by heat or light,
n1 to n4 are each an integer of 0 to 4,
n is an integer of 0 to 8,
When n and n1 to n4 are each 2 or more, the substituents in the parentheses are the same or different from each other. The method according to claim 1,
Wherein the heat or light-crosslinkable functional group is any one of the following structures:

In the above structure,
X1 is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. The method according to claim 1,
And L1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms. The method according to claim 1,
Wherein n is 1 or 2,
R is a substituted or unsubstituted alkyl group; Or -L2-Ar1,
The definition of L2 and Ar1 is the same as defined in the above formula (1). The method according to claim 1,
(1) is a polymer represented by the following formula (2): &lt; EMI ID =
(2)

In Formula 2,
The definitions of R1 to R4, R and n1 to n4 are the same as those in the above formula (1)
n11 is an integer of 0 to 5, and when n11 is 2 or more, Rs are the same or different from each other. The method according to claim 1,
Wherein the formula 1 is a polymer represented by the following formula 3 or 4:
(3)

[Chemical Formula 4]

In the above formulas (3) and (4)
The definitions of R1 to R4 and n1 to n4 are the same as those in Formula 1,
R11 to R13 are the same as or different from each other and each independently have the same definition as R in the above formula (1). The method according to claim 1,
Wherein the polymer comprises a unit represented by the following formula (5): &lt; EMI ID =
[Chemical Formula 5]

In Formula 5,
R 1 to R 4, R, n and n 1 to n 4 have the same meanings as in the above formula (1)
m is an integer of 3 or more and 3,000 or less. The method according to claim 1,
Wherein the polymer comprises a unit represented by any one of the following formulas (5-1) to (5-4):
[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

In the formulas (5-1) to (5-4)
and m is an integer of 3 to 3,000. A coating composition comprising a polymer according to any one of claims 1 to 8. 10. The coating composition of claim 9, wherein the viscosity of the coating composition is between 2 cP and 15 cP. A first electrode;
A second electrode; And
And at least one organic layer provided between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises the coating composition of claim 9 or a cured product thereof. 12. The organic light emitting device according to claim 11, wherein the organic compound layer including the coating composition or a cured product thereof is a hole transport layer. Preparing a substrate;
Forming a first electrode on the substrate;
Forming at least one organic layer on the first electrode; And
And forming a second electrode on the organic material layer,
Wherein the forming of the organic material layer includes forming at least one organic material layer using the coating composition of claim 9. [14] The method of claim 13, wherein the organic compound layer formed using the coating composition is formed using a solution process. 14. The method of claim 13, wherein forming the organic layer formed using the coating composition comprises:
Coating the coating composition on the first electrode; And
And a step of heat-treating or light-treating the coated coating composition.

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