KR20190060484A - Compound, 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 compound having low driving voltage, high efficiency, and long lifetime in an organic light emitting device, a coating composition including the same, an organic light emitting device using the same, and a manufacturing method thereof. The compound of the present invention is represented by chemical formula 1. In chemical formula 1, m is 1 or 2, when m is 1, X is -(L3)_n3-Y3, and when m is 2, X is a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent arylamine group.

Description

TECHNICAL FIELD The present invention relates to a compound, a coating composition containing the same, an organic light emitting device using the same, and a method of manufacturing the same. BACKGROUND ART [0002]

The present invention relates to a compound, a coating composition comprising the compound, 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 can be stored. 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 material used in the solution process should have excellent coatability so that a thin film of uniform thickness can be formed without forming holes or aggregation when forming the thin film.

Third, the layers to be subjected to 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.

Therefore, there is a need in the art to develop new organic materials.

Korean Patent Laid-Open Publication No. 2016-139159

It is an object of the present invention to provide a compound usable in an organic light emitting device for a solution process and an organic light emitting device including the same.

There is provided a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

m is 1 or 2,

When m is 1, X is - (L3) _n3- Y3,

when m is 2, X is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group,

L1 to L3 are the same or different and are each independently a direct bond; -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

L is a substituted or unsubstituted arylene group,

R is hydrogen; heavy hydrogen; A halogen group; 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,

q is an integer of 0 to 8, and when q is 2 or more, Rs are the same or different from each other,

each of n1 to n3 is an integer of 0 to 3, and when n1 to n3 are each 2 or more, the substituents in the parentheses are the same or different from each other,

Y1 and Y3 are the same or different from each other and are each independently any one of the following formulas (2) to (4)

Y2 is hydrogen or any one of the following formulas (2) to (4)

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

R1 to R3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

p1 to p3 are each an integer of 0 to 7, and when p1 to p3 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 compounds described above.

The disclosure also relates to a light emitting device comprising: a first electrode; A second electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described 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 compound according to one embodiment of the present invention can be subjected to a solution process and can be used as a material for an organic material layer of an organic light emitting device and can provide a low driving voltage, a high luminous efficiency and a high lifetime .

In addition, the compound according to one embodiment of the present invention has excellent solubility in a solvent, and since a curing unit including a benzocyclobutane structure is bonded to two or more, a thin film completely cured from heat treatment or UV treatment is formed, A stable thin film which is not damaged is formed.

In addition, since the compound of the present invention has an effect of increasing the band gap by the fluorene structure and reducing the intermolecular interaction by the substituent at the 9-position of fluorene, it easily dissolves in the solution and reduces the problem of precipitation in the solution, It is suitable for application to process. In addition, since the charge mobility is increased by the amine group bonded to the fluorene, the device has low driving voltage, high efficiency and long life characteristics when applied to an organic light emitting device.

1 shows an example of an organic light emitting device according to an embodiment of the present invention.
Fig. 2 shows the results of the membrane retention test of Compound 1. Fig.
Fig. 3 shows the results of the membrane retention test of Comparative Compound 1. Fig.

Hereinafter, the present specification will be described in detail.

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

[Chemical Formula 1]

In Formula 1,

m is 1 or 2,

When m is 1, X is - (L3) _n3- Y3,

when m is 2, X is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group,

L1 to L3 are the same or different and are each independently a direct bond; -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

L is a substituted or unsubstituted arylene group,

R is hydrogen; heavy hydrogen; A halogen group; 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,

q is an integer of 0 to 8, and when q is 2 or more, Rs are the same or different from each other,

each of n1 to n3 is an integer of 0 to 3, and when n1 to n3 are each 2 or more, the substituents in the parentheses are the same or different from each other,

Y1 and Y3 are the same or different from each other and are each independently any one of the following formulas (2) to (4)

Y2 is hydrogen or any one of the following formulas (2) to (4)

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

R1 to R3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

p1 to p3 are each an integer of 0 to 7, and when p1 to p3 are each 2 or more, the substituents in the parentheses are the same or different from each other.

In the formula (1), when m is 2, the structures in parentheses are the same or different from each other.

The compound according to one embodiment of the present invention includes a curing group containing two or more benzocyclobutane structures in the compound to form a stable thin film completely cured from the heat treatment or the UV treatment, It is resistant to the solvent used in forming the layer by the solution process, and migration to another layer can be prevented.

In addition, it can provide excellent coating properties, low driving voltage, high luminous efficiency and high lifetime characteristics.

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 one embodiment of the present invention, the compound of formula (1) is preferably a compound having solubility in a suitable organic solvent.

In addition, in the case of the compound 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; A nitrile group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryl group; An arylamine group; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the halogen group is fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BR _d R _e , wherein R _d and R _e are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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 60. According to one embodiment, the alkyl group may have 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n- .

In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specific examples of the cycloalkyl group 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 alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, and may be 1 to 20 carbon atoms. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, N-decyloxy group, n-decyloxy group, n-decyloxy group, and the like.

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) 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), and the like. 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, and the number of carbon atoms is not particularly limited, but may be 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to another embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, benzothiophene, benzofurane, dibenzothiophene, However, 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, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a triphenylamine group, a biphenylphenylamine group, An amine group, and a fluorenylphenylamine group, but the present invention is not limited thereto.

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

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

According to one embodiment of the present invention, when m is 1 in Formula 1, X is - (L3) _n3- Y3, and when m is 2, X is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group.

When the divalent arylamine group is a diarylamine group or a triarylamine group and X is a divalent arylamine group, the carbon atoms constituting the aryl group of the diarylamine group or the triarylamine group and the N The atoms bind to each other.

According to another embodiment, when m is 2, X is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent arylamine group, and the aryl group of the arylamine group has 6 to 60 carbon atoms.

In another embodiment, when m is 2, X is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted substituted or unsubstituted divalent arylamine group, and the aryl group of the arylamine group has 6 to 30 carbon atoms.

According to another embodiment, when m is 2, X is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted divalent triphenylamine group.

In one embodiment of the present invention, Formula 1 may be represented by Formula 1-1 or Formula 1-2.

[Formula 1-1]

[Formula 1-2]

In the above formulas 1-1 and 1-2,

Y1 to Y3, L, L1 to L3, R, n1 to n3 and q are as defined in the above formula (1)

X1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group,

L 'is a substituted or unsubstituted arylene group,

L1 'and L2' are the same or different and are each independently a direct bond; -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

R 'is hydrogen; heavy hydrogen; A halogen group; 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,

Y1 'is any one of the formulas (2) to (4)

Y2 < 2 > is hydrogen or any one of the formulas (2) to (4)

n1 'and n2' are each an integer of 0 to 3, and when n1 'and n2' are each 2 or more, the substituents in the parentheses are the same or different from each other,

q 'is an integer of 0 to 8, and when q is 2 or more, R' are the same or different from each other.

According to one embodiment of the present disclosure, n1 'is an integer of 0 to 3.

According to another embodiment, n1 'is 0, 1 or 3.

According to one embodiment of the present disclosure, L1 'is a direct bond; -O-; 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.

According to another embodiment, L1 'is a direct bond; -O-; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present disclosure, L1 'is a direct bond; -O-; An alkylene group having 1 to 10 carbon atoms; Or an arylene group having 6 to 30 carbon atoms.

According to another embodiment, L1 'is a direct bond; -O-; A methylene group; An ethylene group; Propylene group; Butylene group; Pentylene group; A hexylene group; A phenylene group; Biphenylene group; Or a naphthylene group.

According to one embodiment of the present disclosure, n1 is an integer of 0 to 3.

According to another embodiment, n1 is 0, 1 or 3.

According to one embodiment of the present disclosure, L1 is a direct bond; -O-; 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.

According to another embodiment, L1 is a direct bond; -O-; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present disclosure, L1 is a direct bond; -O-; An alkylene group having 1 to 10 carbon atoms; Or an arylene group having 6 to 30 carbon atoms.

According to another embodiment, L1 is a direct bond; -O-; A methylene group; An ethylene group; Propylene group; Butylene group; Pentylene group; A hexylene group; A phenylene group; Biphenylene group; Or a naphthylene group.

According to one embodiment of the present invention, the formula (1) may be represented by any of the following formulas (1-3) to (1-5).

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-3 to 1-5 above,

The definitions of Y1, Y2, L, L2, n2, X, R, q and m are as defined in the above formula (1)

L11 to L14 are the same or different and are each independently -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, L11 to L14 are the same or different from each other and are each independently -O-; 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.

According to another embodiment, L11 to L14 are the same or different and are each independently -O-; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L11 to L14 are the same or different and are each independently -O-; An alkylene group having 1 to 10 carbon atoms; Or an arylene group having 6 to 30 carbon atoms.

According to another embodiment, any one of L11 to L13 is -O-, the other is an alkylene group having 1 to 10 carbon atoms, and the other is an arylene group having 6 to 30 carbon atoms.

In another embodiment, any one of L11 to L13 is -O-, and the other is a methylene group; An ethylene group; Propylene group; Butylene group; Pentylene group; Or a hexylene group, and the other is a phenylene group; Biphenylene group; Or a naphthylene group.

According to another embodiment, L11 is a phenylene group, L12 is -O-, and L13 is a hexylene group.

In another embodiment, any one of L11 to L13 is -O- and the others are the same or different and each independently is an arylene group having 6 to 30 carbon atoms.

According to another embodiment, any one of L11 to L13 is -O-, and the others are the same or different, and each independently is a phenylene group.

In another embodiment, L11 and L13 are phenylene groups and L12 is -O-.

According to another embodiment, L14 is a phenylene group.

According to one embodiment of the present invention, the formula 1-2 may be represented by any one of the following formulas 1-2-1 to 1-2-3.

[Formula 1-2-1]

[Formula 1-2-2]

[Formula 1-2-3]

In Formulas 1-2-1 to 1-2-3,

The definitions of Y1, Y2, L, L2, n2, R, q, Y1 ', Y2', L ', L2', n2 ', R' and q '

X1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group,

L21 to L28 are the same or different from each other and each independently -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently -O-; 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.

According to another embodiment, L21 to L23 are the same or different from each other and are each independently -O-; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L21 to L23 are the same or different and are each independently -O-; An alkylene group having 1 to 10 carbon atoms; Or an arylene group having 6 to 30 carbon atoms.

According to another embodiment, one of L21 to L23 is -O-, the other is an alkylene group having 1 to 10 carbon atoms, and the other is an arylene group having 6 to 30 carbon atoms.

In another embodiment, any one of L21 to L23 is -O-, and the other is a methylene group; An ethylene group; Propylene group; Butylene group; Pentylene group; Or a hexylene group, and the other is a phenylene group; Biphenylene group; Or a naphthylene group.

According to another embodiment, L21 is -O-, L22 is a hexylene group, and L23 is a phenylene group.

In another embodiment, any one of L21 to L23 is -O-, and the rest are the same or different, and each independently is an arylene group having 6 to 30 carbon atoms.

According to another embodiment, any one of L21 to L23 is -O-, and the others are the same or different, and each independently is a phenylene group.

In another embodiment, L21 and L23 are phenylene and L22 is -O-.

According to one embodiment of the present invention, L24 to L26 are the same or different from each other and each independently -O-; 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.

According to another embodiment, L24 to L26 are the same or different from each other, and each independently -O-; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L24 to L26 are the same or different and are each independently -O-; An alkylene group having 1 to 10 carbon atoms; Or an arylene group having 6 to 30 carbon atoms.

According to another embodiment, any one of L24 to L26 is -O-, the other is an alkylene group having 1 to 10 carbon atoms, and the other is an arylene group having 6 to 30 carbon atoms.

In another embodiment, any one of L24 to L26 is -O-, and the other is a methylene group; An ethylene group; Propylene group; Butylene group; Pentylene group; Or a hexylene group, and the other is a phenylene group; Biphenylene group; Or a naphthylene group.

According to another embodiment, L24 is -O-, L25 is a hexylene group, and L26 is a phenylene group.

In another embodiment, any one of L24 to L26 is -O- and the others are the same or different, and each independently is an arylene group having 6 to 30 carbon atoms.

According to another embodiment, any one of L24 to L26 is -O-, and the others are the same or different, and each independently is a phenylene group.

In another embodiment, L24 and L26 are phenylene and L25 is -O-.

According to one embodiment of the present disclosure, L27 and L28 are the same or different from each other and are each independently -O-; 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, L27 and L28 are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another embodiment, L27 and L28 are the same or different and are each independently a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In another embodiment, L27 and L28 are the same or different and each independently represents a substituted or unsubstituted phenylene group.

According to another embodiment, L27 and L28 are the same or different and are each independently a phenylene group.

According to one embodiment of the present invention, X1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent arylamine group, and the aryl group of the arylamine group has 6 to 60 carbon atoms.

When the divalent arylamine group is a diarylamine group or a triarylamine group, and when X1 is a divalent arylamine group, the carbon atom constituting the aryl group of the diarylamine group or the triarylamine group and the N The atoms bind to each other.

According to another embodiment, X1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent arylamine group, and the aryl group of the arylamine group has 6 to 30 carbon atoms.

In another embodiment, X1 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted divalent triphenylamine group.

According to one embodiment of the present invention, X1 may be represented by any one of the following formulas (1-A) to (1-C).

[Chemical Formula 1-A]

[Chemical Formula 1-B]

[Chemical Formula 1-C]

In the above formulas (1-A) to (1-C)

R11 to R16 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

each of m1 to m5 is an integer of 0 to 4, and when m1 to m5 are 2 or more, the substituents in the parentheses are the same or different from each other,

m6 is an integer of 0 to 5, and when m6 is 2 or more, R16 are the same or different from each other.

In one embodiment of the present invention, R11 to R16 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; 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.

According to another embodiment, R11 to R16 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.

According to another embodiment, R11 to R16 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.

In another embodiment, R11 to R16 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted n-butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted dibenzofurane group.

According to another embodiment, R11 to R16 are the same or different and each independently hydrogen; heavy hydrogen; Methyl group; An ethyl group; n-propyl group; an n-butyl group; tert-butyl group; A phenyl group; A biphenyl group; Or a dibenzofurane group.

In another embodiment, R11 to R16 are hydrogen.

According to one embodiment of the present disclosure, m1 is 0 or 1.

According to one embodiment of the present disclosure, m2 is 0 or 1.

According to one embodiment of the present disclosure, m3 is 0 or 1.

According to one embodiment of the present disclosure, m4 is 0 or 1.

According to one embodiment of the present disclosure, m5 is 0 or 1.

In one embodiment of the present disclosure, R and R '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; A substituted or unsubstituted C1 to C30 alkoxy group; 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.

According to another embodiment, R and R 'are the same or different from each other, and each independently hydrogen; 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 and R 'are the same or different and are each independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, R and R 'are hydrogen.

According to one embodiment of the present disclosure, q and q 'are each 0 or 1.

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

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

In another embodiment, L 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.

In another embodiment, L is selected from the group consisting of a phenylene group; Biphenylene group; A terphenylene group; Or a naphthylene group.

According to one embodiment of the present invention, L is a phenylene group or a biphenylene group.

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

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

In another embodiment, L '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.

In another embodiment, L 'is a phenylene group; Biphenylene group; A terphenylene group; Or a naphthylene group.

According to one embodiment of the present invention, L 'is a phenylene group; Or a biphenylene group.

According to one embodiment of the present disclosure, n2 is 1 or 2.

In another embodiment, n2 is one.

According to one embodiment of the present disclosure, n2 'is 1 or 2.

In another embodiment, n2 'is one.

According to one embodiment of the present disclosure, L2 is a direct bond; -O-; 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.

According to another embodiment, L2 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another embodiment, L2 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another embodiment, L2 is an arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group or an arylamine group.

In another embodiment, L2 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted fluorenylene group; Or a substituted or unsubstituted naphthylene group.

According to another embodiment, L2 is a phenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; A biphenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; A terphenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; A fluorenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; Or a naphthylene group substituted or unsubstituted with a methyl group or a diphenylamine group.

In another embodiment, L < 2 > is selected from the group consisting of a phenylene group; A biphenylene group substituted or unsubstituted with a diphenylamine group; A terphenylene group; A 9,9-dimethylfluorenylene group; Or a naphthylene group.

According to one embodiment of the present invention, L2 represents a phenylene group; A biphenylene group substituted or unsubstituted with a diphenylamine group; A 9,9-dimethylfluorenylene group; Or a naphthylene group. The naphthylene group is a 1-naphthylene group or a 2-naphthylene group.

According to one embodiment of the present disclosure, L2 'is a direct bond; -O-; 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.

According to another embodiment, L2 'is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another embodiment, L2 'is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to another embodiment, L2 'is an arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group or an arylamine group.

In another embodiment, L2 'is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted fluorenylene group; Or a substituted or unsubstituted naphthylene group.

According to another embodiment, L2 'is a phenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; A biphenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; A terphenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; A fluorenylene group substituted or unsubstituted with a methyl group or a diphenylamine group; Or a naphthylene group substituted or unsubstituted with a methyl group or a diphenylamine group.

In another embodiment, L2 'is a phenylene group; A biphenylene group substituted or unsubstituted with a diphenylamine group; A terphenylene group; A 9,9-dimethylfluorenylene group; Or a naphthylene group.

According to one embodiment of the present invention, L2 'is a phenylene group; A biphenylene group substituted or unsubstituted with a diphenylamine group; A 9,9-dimethylfluorenylene group; Or a naphthylene group. The naphthylene group is a 1-naphthylene group or a 2-naphthylene group.

According to one embodiment of the present disclosure, n3 is 1 or 2.

In another embodiment, n3 is one.

According to one embodiment of the present disclosure, L3 is a direct bond; -O-; 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.

According to another embodiment, L3 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In another embodiment, L3 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L3 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.

In another embodiment, L3 is selected from the group consisting of a phenylene group; Biphenylene group; A terphenylene group; Or a naphthylene group.

According to one embodiment of the present invention, L3 is a phenylene group.

In one embodiment of the present invention, Y1 is any one of the following formulas (2) to (4).

In one embodiment of the present invention, Y1 'is any one of the following formulas (2) to (4).

In one embodiment of the present invention, Y2 is hydrogen or any one of the following formulas (2) to (4).

In one embodiment of the present invention, Y2 'is hydrogen or any one of the following formulas (2) to (4).

In one embodiment of the present invention, Y3 is any one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

R1 to R3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

p1 to p3 are each an integer of 0 to 7, and when p1 to p3 are each 2 or more, the substituents in the parentheses are the same or different from each other.

According to one embodiment of the present invention, R1 to R3 are the same or different from each other and each independently hydrogen; heavy hydrogen; 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.

According to another embodiment, R 1 to R 3 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, R 1 to R 3 are hydrogen.

According to one embodiment of the present disclosure, p1 is 0 or 1.

According to one embodiment of the present disclosure, p2 is 0 or 1.

According to one embodiment of the present disclosure, p3 is 0 or 1.

The above-mentioned formulas (2) to (4) are curing units comprising benzocyclobutane. In the present specification, the term "curing unit" may mean a reactive substituent which causes crosslinking among the compounds by exposure to heat and / or light. The crosslinking can be produced by heat treatment or light irradiation, and connecting the radicals generated by decomposition of the carbon-carbon multiple bond, cyclic structure.

The compound of the present invention contains two or more curing groups of any one of formulas (2) to (4) in the compound to form a layer having a high film retention rate when applied to an organic light emitting device.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following compounds 1 to 20.

[Compound 1]

[Compound 2]

[Compound 3]

[Compound 4]

[Compound 5]

[Compound 6]

[Compound 7]

[Compound 8]

[Compound 9]

[Compound 10]

[Compound 11]

[Compound 12]

[Compound 13]

[Compound 14]

[Compound 15]

[Compound 16]

[Compound 17]

[Compound 18]

[Compound 19]

[Compound 20]

The compound according to one embodiment of the present specification can be produced by a production method described below.

For example, the compound of Formula 1 can be prepared as a core structure as shown in Reaction Scheme 1 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.

<Reaction Scheme 1>

In one embodiment of the present disclosure, coating compositions comprising the compounds described above are provided.

In one embodiment of the present disclosure, the coating composition comprises a compound and a solvent as described above.

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 is exemplified, but a solvent capable of dissolving or dispersing the compound of the formula (1) 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 one embodiment of the present disclosure, the coating composition further comprises no p-doping material.

In one embodiment of the present disclosure, the coating composition further comprises a p-doping material.

In this specification, the p-doped material means a material that has a p-type semiconductor property as a host material. p semiconductor property means a property of injecting or transporting holes at a highest occupied molecular orbital (HOMO) energy level, that is, a material having a high conductivity of holes.

In one embodiment of the present invention, the p-doped material may be represented by any one of the following formulas A to C, but is not limited thereto.

(A)

[Chemical Formula B]

&Lt; RTI ID = 0.0 &

In this specification, the p-doping material may be a material that has p-semiconductor properties, and one or two or more materials may be used.

In one embodiment of the present invention, the content of the p-doped material is 0 wt% to 50 wt% based on the compound of the formula (1).

In one embodiment of the present disclosure, the content of the p-doped material comprises 0 to 30% by weight based on the total solids content of the coating composition. In one embodiment of the present disclosure, the content of the p-doped material preferably comprises 1 to 30% by weight based on the total solid content of the coating composition, and in another embodiment, the p-doped material More preferably 10 to 30% by weight based on the total solids content of the coating composition.

In yet another embodiment, the coating composition comprises a monolayer comprising a curable group that is crosslinkable by heat or light; Or a monomer capable of forming a polymer by heat. A monomolecule comprising a curing group which is crosslinkable by heat or light as described above; Or a molecular weight of a monomolecule including an end group capable of forming a polymer by heat can be 3,000 g / mol or less.

In one embodiment of the present disclosure, the coating composition has a molecular weight less than or equal to 2,000 g / mol and comprises a curing agent that is crosslinkable by heat or light; Or a terminal molecule containing a terminal group capable of forming a polymer by heat.

A monomolecule comprising a curable group which is crosslinkable by heat or light; Or monomers comprising an end group capable of forming a polymer by thermal polymerization include aryl, such as phenyl, biphenyl, fluorene, naphthalene; Arylamine; Or a curing unit capable of crosslinking by heat or light to fluorene, or a single molecule substituted with a terminal group capable of forming a polymer by heat.

In another embodiment, the viscosity of the coating composition is from 2 cP to 15 cP. More preferably 3 cP to 8 cP, but is not limited thereto. When the viscosity is satisfied, it is easy to prepare a cleaning agent.

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 provided 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, and the coating composition or a cured product thereof comprises the coating And the composition is cured by heat treatment or light treatment.

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.

In one embodiment of the present invention, the organic compound layer comprising the coating composition or a cured product thereof is an electron transport layer or an electron injection layer.

In another embodiment, the organic compound layer comprising the coating composition or a cured product thereof is a light emitting layer.

In another embodiment, the organic compound layer including the coating composition or the cured product thereof is a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a host of the light emitting layer.

In another embodiment, the organic compound layer comprising the coating composition or a cured product thereof is a light emitting layer, and the light emitting layer contains the compound of Formula 1 as a dopant of the light emitting layer.

The organic light emitting device may be stacked in the order of an anode / a hole injection layer / a hole transporting layer / a light emitting layer / an electron transporting layer / an electron injection layer / a cathode.

According to another embodiment, the organic light emitting device may be stacked in the order of a layer / a light emitting layer / an electron transporting layer / an electron injecting layer / a cathode simultaneously performing anode / hole injection and hole transporting.

According to another embodiment, the organic light emitting diode may be stacked in the order of an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / a layer / cathode simultaneously injecting electrons and electron transporting.

According to another embodiment, the organic light emitting diode may be stacked in the order of a layer / a light emitting layer / an electron injecting layer simultaneously injecting electrons and / or an electron transporting layer.

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 electrons 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 luminescent device of the present invention includes a hole injecting layer, a hole transporting layer, a layer simultaneously transporting holes and 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.

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 of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using a coating composition comprising the compound of Formula 1 above.

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 A hole injection layer, a hole transporting layer, a light emitting layer, and a layer that simultaneously transports electrons and electrons, 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.

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.

According to one embodiment of the present disclosure, the step of forming one or more organic layers using the coating composition uses a solution process.

In one embodiment of the present invention, the step of forming one or more organic layers using the coating composition uses a spin coating method.

In another embodiment, the step of forming one or more organic layers using the coating composition uses 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.

Since the coating composition according to one embodiment of the present invention has a structural characteristic and is suitable for a solution process, the coating composition can be formed by a printing method, so that there is an economical effect in time and cost in manufacturing a device.

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

In one embodiment of the present invention, the heat treatment may be performed through heat treatment, and the heat treatment temperature in the heat treatment step may be 85 to 250 ° C, and may be 100 to 250 ° C according to an embodiment, In another embodiment, it may be between 150 ° C and 250 ° C.

In another embodiment, the heat treatment time in the heat treatment step may be from 1 minute to 2 hours, and may be from 1 minute to 1 hour according to one embodiment. In another embodiment, 1 hour.

In the case where the organic compound layer formed using the coating composition includes the heat treatment or the light treatment step, the organic compound layer including a structure in which a plurality of the compounds included in the coating composition form a crosslink to form a thin film may be provided. In this case, when another layer is laminated on the surface of the organic material layer formed using the coating composition, it can be prevented that it is dissolved, morphologically affected or decomposed by the solvent.

Therefore, when the organic material layer formed using the coating composition is formed by including the heat treatment or the light treatment step, the resistance to the solvent is increased, so that the multilayer can be formed by repeating the solution deposition and crosslinking method, Life characteristics can be increased.

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. Synthesis of Compound 1

1) Synthesis of intermediate 1-1

                                 [Intermediate 1-1]

After dissolving 4-bromobenzocyclobutene (4.23 mL, 34 mmol) in tetrahydrofuran [THF] (100 mL), the solution was added to a dry ice / acetone bath and dried in a dry ice / acetone bath The temperature was lowered. n-BuLi (13 mL, 32 mmol, 2.5 M in hexane) was slowly added and stirred for 1 hour. The following 9-fluorenone [9-fluorenone] (3.6 g, 20 mmol) was added thereto, followed by stirring overnight. The reaction was quenched with water and extracted with ethyl acetate water. The organic layer was collected and dried over anhydrous MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary evaporator to remove the organic solvent, and the residue was subjected to column purification to obtain 4.32 g (yield 76%) of Intermediate 1-1.

2) Synthesis of intermediate 1-2

                              [Intermediate 1-2]

Intermediate 1-1 (3.4 g, 12 mmol) and phenol (3.4 g, 36 mmol) were dissolved in methanesulfonic acid (17 mL) and stirred at 50 ° C for 4 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic layer was collected and dried over anhydrous MgSO ₄ and filtered. Thereafter, the filtrate was dried with a vacuum rotary condenser to remove the organic solvent, and the residue was subjected to column purification to obtain 2.4 g (yield 55%) of intermediate 1-2.

3) Synthesis of intermediate 1-3

                                 [Intermediate 1-3]

Intermediate 1-2 (2.4 g, 6 mmol) and pyridine (0.97 mL, 12 mmol) were dissolved in dichloromethane (40 mL) and cooled to 0 占 폚. A solution of triflic anhydride (1.21 mL, 7.2 mmol) in dichloromethane (20 mL) was slowly added to the reaction mixture. Thereafter, the mixture was stirred at room temperature for 2 hours. The reaction was quenched with 1 M HCl and extracted with dichloromethane. The organic layer was collected and dried over anhydrous MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary condenser to remove the organic solvent to obtain 2.81 g (yield: 95%) of intermediate 1-3.

4) Synthesis of Compound 1

                                                [Compound 1]

Intermediate 1-3 (2.8 g, 5.7 mmol) and N , N -diphenylbenzidine (800 mg, 2.38 mmol) Pd (P t Bu ₃ ) ₂ (61 mg, 0.12 mmol) and NaO t Bu (686 g, 7.14 mmol) were placed in a round bottom flask and replaced with nitrogen. Toluene (12 mL) was added thereto, followed by stirring at 90 ° C for 4 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. Thereafter, the organic layer was collected, and the organic layer was dried and filtered using MgSO ₄ . The filtrate was dried with a vacuum rotary evaporator and the organic solvent was blown off. The residue was subjected to column purification to obtain 1.78 g (73% yield) of Compound 1.

NMR measurement of Compound ^{1: 1 H NMR (500 MHz} , CDCl 3) δ 7.88 (m, 4H), 7.55 (m, 8H), 7.40 - 7.35 (m, 4H), 7.30 - 7.22 (m, 12H), 4H), 6.88 (d, 4H), 2.88 (s, 8H), 7.18 (m, 6H)

Synthetic example  2. Synthesis of Compound 2

                                                  [Compound 2]

Pd (PtBu ₃ ) ₂ (128 mg, 0.25 mmol) and NaO t Bu (1.44 g, 15 mmol) were added to a round bottom flask And replaced with a nitrogen atmosphere. 25 mL of anhydrous toluene was added, and the mixture was stirred at 90 占 폚 for 4 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic layer was collected and dried over anhydrous MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary evaporator to remove the organic solvent, and the residue was subjected to column purification and column purification to obtain 2.1 g (yield 70%) of Compound 2.

NMR measurement of the compound ^{2: 1 H NMR (500 MHz} , CDCl 3) δ 7.90 (d, 2H), 7.82 (s, 1H), 7.58- 7.52 (m, 4H), 7.42 - 7.37 (m, 5H), 2H), 2.88-2.86 (m, 8H), 7.29-7.22 (m, 5H), 7.19-7.13 (m, 4H)

Synthetic example  3. Synthesis of Compound 3

                                               [Compound 3]

Pd (PtBu ₃ ) ₂ (128 mg, 0.25 mmol) and NaO t Bu (1.44 g, 15 mmol) were added to a round bottom flask And replaced with a nitrogen atmosphere. 25 mL of anhydrous toluene was added, and the mixture was stirred at 90 占 폚 for 4 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic layer was collected and dried over anhydrous MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary evaporator to remove the organic solvent, and the residue was subjected to column purification and column purification to obtain 2.3 g (yield: 63%) of Compound 3.

Compound 3 of the NMR ^{measurements: 1 H NMR (500 MHz,} CDCl 3) δ 7.88 (d, 2H), 7.82 (s, 2H), 7.56 (d, 4H), 7.54 (d, 2H), 7.40 (d, 2H), 7.37 (d, 4H), 7.36 (d, 2H), 7.30-7.28 (m, 4H), 7.19-7.08

Synthetic example  4. Synthesis of Comparative Compound 1

1) Synthesis of intermediate 4-1

[Intermediate 4-1]

9,7-dibromo-9,9-dimethyl-9H-fluorene] (4.93 g, 14 mmol), amine (2.45 g, 10 mmol ), Pd (PtBu ₃ ) ₂ (256 mg, 0.5 mmol) and NaO t Bu (2.88 g, 30 mmol) were placed in a round bottom flask and replaced with nitrogen atmosphere. 50 mL of anhydrous toluene was added, and the mixture was stirred at 90 占 폚 for 4 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic layer was collected and dried over anhydrous MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary evaporator to remove the organic solvent, and the residue was subjected to column purification and column purification to obtain 2.9 g (yield: 56%) of Intermediate 4-1.

2) Synthesis of Comparative Compound 1

[Comparative Compound 1]

Pd (PtBu ₃ ) ₂ (128 mg, 0.25 mmol) and NaO t Bu (1.44 g, 15 mmol) were added to a round-bottomed flask with intermediate 4-1 (2.58 g, 5 mmol) Nitrogen atmosphere. 25 mL of anhydrous toluene was added, and the mixture was stirred at 90 占 폚 for 4 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic layer was collected and dried over anhydrous MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary evaporator to remove the organic solvent, and the residue was subjected to column purification and column purification to obtain 3 g (yield 86%) of Comparative Compound 1.

NMR measurements of Comparative Compound ^{1: 1 H NMR (500 MHz} , CDCl 3) δ 7.85 (d, 2H), 7.83 (s, 1H), 7.75 (d, 2H), 7.56 (m, 4H), 7.47 (dd (D, 2H), 7.42-7.37 (m, 8H), 7.33 (s, 2H), 7.28 t, 2H), 2.89 (m, 4H), 1.71 (s, 6H)

< Experimental Example >

Experimental Example  1. Thin film retention rate measurement

Compound 1 and Comparative Compound 1 were each spin-coated on glass with 2 wt% toluene solution to form a thin film. Treated at 220 캜 for 30 minutes in a nitrogen atmosphere, and the UV absorption of each thin film was measured. Again, the films were soaked in toluene for 10 minutes and UV was measured after drying. Thin film retention was measured by comparing the maximum peak of UV absorption before and after immersion in toluene (Toluene).

Compound 1 having two curing groups had excellent resistance to solvents (Fig. 2, thin film retention rate 100%), whereas Comparative Compound 1 having one curing group did not retain thin films (Fig. 3, thin film retention rate 0% . It can be seen from this that, in the case of having two or more curable groups, the cross-linking reaction proceeds and the membrane retention ratio is high.

FIG. 2 is a graph showing the results of the film retention test of the compound 1, FIG. 3 is a graph showing the results of the film retention test of the comparative compound 1, the horizontal axis in FIGS. 2 and 3 means a wavelength, It means density (OD: Optical Density).

Experimental Example  2. Device fabrication

Preparation of Substrate

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice.

After the distilled water was washed, the substrate was ultrasonically washed with a solvent of isopropyl alcohol and acetone, and the substrate was washed for 5 minutes, and then the substrate was transported to a glove box.

Device example  One.

1.5 wt% toluene [toluene] ink of Compound 1: p dopant (Formula C) (8: 2) was spin-coated (4000 rpm) on the ITO transparent electrode and annealed (cured) at 230 캜 for 30 minutes to form a 30 nm thick A hole injection layer was formed. Thereafter, the layer was transferred to a vacuum evaporator, and then a compound D was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 40 nm. Next, Compound E and Compound F were vacuum deposited on the hole transporting layer at a concentration of 8 wt% to a thickness of 30 nm to form a light emitting layer. Compound G was vacuum deposited on the light emitting layer to a thickness of 35 nm to form a layer for simultaneous electron injection and electron transport. Aluminum was sequentially deposited to a thickness of 1 nm and a thickness of 100 nm on the layer simultaneously injecting electrons and electrons to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the cathode was maintained at a deposition rate of 0.3 Å / sec for lithium fluoride and the deposition rate of 2 Å / sec for aluminum, ^-7 to 5 X 10 &lt; ^-8 &gt; torr.

&Lt; RTI ID = 0.0 &

[Compound D]

[Compound E]

[Compound F]

[Compound G]

Device example  2.

Compound 1: p dopant (8: 2) 1.5 wt% of compound 2: p dopant (8: 2) synthesized in Synthesis Example 2 instead of 1.5 wt% An organic light emitting device was prepared in the same manner as in the device example 1 except that toluene ink was used.

Device example  3.

Compound 1: p dopant (8: 2) 1.5% by weight of compound 3: p dopant (8: 2) synthesized in Synthesis Example 3 instead of 1.5% by weight toluene ink at the time of forming the hole injection layer in the production process of Device Example 1 An organic light emitting device was prepared in the same manner as in the device example 1 except that toluene ink was used.

compare Device example  One.

(1: p dopant (8: 2) 1.5 wt% of the comparative compound 1: p dopant (8: 2) synthesized in Synthesis Example 4 instead of 1.5 wt% toluene ink at the time of forming the hole injection layer % Toluene ink was used as the organic light emitting device.

The results of the material according to the invention and the results of the device made of the comparative material are shown in Table 1 below. T95 means the time required to reduce the initial luminance (500 nits) to 95% at a current density of 10 mA / cm ² .

Volt J (mA / cm ² ) QE (%) Cd / m ² T95 @ 500 nit Device Example 1 5.08 10 3.6 105 60 Device Example 2 4.73 10 3.0 75 43 Element Example 3 4.88 10 3.2 98 52 Comparative Device Example 1 5.58 10 2.5 62 22

The compounds according to one embodiment of the present invention are excellent in solubility in an organic solvent so that the coating composition can be easily prepared. From the results shown in Table 1, it can be seen that when the organic light emitting device is manufactured using the coating composition, Coating layer can be formed and the stability of the film is excellent. Thus, it can be confirmed that an organic light emitting device having a low driving voltage, and excellent efficiency and lifetime characteristics can be manufactured.

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

Claims (12)

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

In Formula 1,
m is 1 or 2,
When m is 1, X is - (L3) _n3- Y3,
when m is 2, X is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group,
L1 to L3 are the same or different and are each independently a direct bond; -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
L is a substituted or unsubstituted arylene group,
R is hydrogen; heavy hydrogen; A halogen group; 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,
q is an integer of 0 to 8, and when q is 2 or more, Rs are the same or different from each other,
each of n1 to n3 is an integer of 0 to 3, and when n1 to n3 are each 2 or more, the substituents in the parentheses are the same or different from each other,
Y1 and Y3 are the same or different from each other and are each independently any one of the following formulas (2) to (4)
Y2 is hydrogen or any one of the following formulas (2) to (4)
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
R1 to R3 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
p1 to p3 are each an integer of 0 to 7, and when p1 to p3 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 compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2:
[Formula 1-1]

[Formula 1-2]

In the above formulas 1-1 and 1-2,
Y1 to Y3, L, L1 to L3, R, n1 to n3 and q are as defined in the above formula (1)
X1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group,
L 'is a substituted or unsubstituted arylene group,
L1 'and L2' are the same or different and are each independently a direct bond; -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
R 'is hydrogen; heavy hydrogen; A halogen group; 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,
Y1 'is any one of the formulas (2) to (4)
Y2 &lt; 2 &gt; is hydrogen or any one of the formulas (2) to (4)
n1 'and n2' are each an integer of 0 to 3, and when n1 'and n2' are each 2 or more, the substituents in the parentheses are the same or different from each other,
q 'is an integer of 0 to 8, and when q is 2 or more, R' are the same or different from each other. The method according to claim 1,
(1) is a compound represented by any one of the following formulas (1-3) to (1-5):
[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-3 to 1-5 above,
The definitions of Y1, Y2, L, L2, n2, X, R, q and m are as defined in the above formula (1)
L11 to L14 are the same or different and are each independently -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group. The method of claim 2,
The compound represented by Formula 1-2 is represented by any one of the following formulas 1-2-1 to 1-2-3:
[Formula 1-2-1]

[Formula 1-2-2]

[Formula 1-2-3]

In Formulas 1-2-1 to 1-2-3,
The definitions of Y1, Y2, L, L2, n2, R, q, Y1 ', Y2', L ', L2', n2 ', R' and q '
X1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent arylamine group,
L21 to L28 are the same or different from each other and each independently -O-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group. The method of claim 2,
Wherein X &lt; 1 &gt; is any one of the following formulas 1-A to 1-C:
[Chemical Formula 1-A]

[Chemical Formula 1-B]

[Chemical Formula 1-C]

In the above formulas (1-A) to (1-C)
R11 to R16 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
each of m1 to m5 is an integer of 0 to 4, and when m1 to m5 are 2 or more, the substituents in the parentheses are the same or different from each other,
m6 is an integer of 0 to 5, and when m6 is 2 or more, R16 are the same or different from each other. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following compounds 1 to 20:
[Compound 1]

[Compound 2]

[Compound 3]

[Compound 4]

[Compound 5]

[Compound 6]

[Compound 7]

[Compound 8]

[Compound 9]

[Compound 10]

[Compound 11]

[Compound 12]

[Compound 13]

[Compound 14]

[Compound 15]

[Compound 16]

[Compound 17]

[Compound 18]

[Compound 19]

[Compound 20]

. A coating composition comprising a compound according to any one of claims 1 to 6. 8. The coating composition of claim 7, wherein the coating composition further comprises a p-doping material. 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 7 or a cured product thereof. The method of claim 9,
Wherein the organic compound layer including the coating composition or the cured product thereof is a hole transporting layer or a hole injecting 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 7. The method of claim 11,
The step of forming one or more organic layers using the coating composition
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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