KR20210094319A - Compound, coating composition comprising same, organic light emitting device using same and method of manufacturing same - Google Patents

Abstract

The present specification relates to a compound represented by a chemical formula 1, a coating composition comprising the compound represented by the chemical formula 1, an organic light emitting device using the same, and a method for manufacturing the same. An object of the present specification is to provide the compound that can be used in manufacturing the organic light emitting device by a solution process and the organic light emitting device including the same.

Description

Compound, coating composition containing same, organic light emitting device using same, and manufacturing method thereof

The present specification relates to a compound, a coating composition including the compound, an organic light emitting device formed using the coating composition, and a method for manufacturing the same.

The organic light emitting phenomenon is one example in which electric current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light emitting phenomenon is as follows. When an organic material layer is placed between the anode and the cathode, when a current is applied between the two electrodes, electrons and holes are respectively injected into the organic material layer from the cathode and the anode. Electrons and holes injected into the organic layer recombine to form excitons, and the excitons fall back to the ground state and emit light. An organic light emitting device using this principle is generally a cathode, an anode, and an organic material layer positioned therebetween, for example, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

Conventionally, a deposition process has been mainly used to manufacture an organic light emitting device. However, there is a problem that a lot of material loss occurs when manufacturing an organic light emitting device through the deposition process. It is being developed, and the development of a material that can be used in a solution process is required.

Korean Patent Publication No. 2012-0112277

An object of the present specification is to provide a compound that can be used in manufacturing an organic light emitting device by a solution process and an organic light emitting device including the same.

The present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted heteroarylene group; or -O-;

Ar1 to Ar4 and R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X1 to X4 are the same as or different from each other, and each independently a curable group,

a1 to a4 are each an integer of 0 to 5, and when a1 to a4 are each 2 or more, the substituents in parentheses are the same as or different from each other,

n1 to n4 are each an integer of 0 to 3, n5 to n8 are each an integer of 0 to 8, and when n1 to n8 are each 2 or more, the substituents in parentheses are the same as or different from each other.

The present specification provides a coating composition comprising the aforementioned compound.

The present specification also includes 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 specification includes the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer includes forming one or more organic material layers using the above-described coating composition. to provide.

The compound according to an exemplary embodiment of the present invention can be used as a material for an organic material layer of an organic light-emitting device, and can be used in a solution process to manufacture a large-area device, as well as low driving voltage, high luminous efficiency, and high lifespan characteristics. It is possible to provide a device having

1 illustrates an example of an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in detail.

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

[Formula 1]

In Formula 1,

L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted heteroarylene group; or -O-;

Ar1 to Ar4 and R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X1 to X4 are the same as or different from each other, and each independently a curable group,

a1 to a4 are each an integer of 0 to 5, and when a1 to a4 are each 2 or more, the substituents in parentheses are the same as or different from each other,

n1 to n4 are each an integer of 0 to 3, n5 to n8 are each an integer of 0 to 8, and when n1 to n8 are each 2 or more, the substituents in parentheses are the same as or different from each other.

The compound represented by Formula 1 has a structure in which fluorene to which a curing group is bonded to a spirobifluorene core is connected through an amine group, and four amine groups to which fluorene is bonded are characterized in that the core is bonded to the core. .

The compound represented by Formula 1 has excellent resistance to the solvent of the additional process of forming an additional layer on the thin film produced by heat or light treatment of the coating composition containing the compound by including a curable group in the compound. In addition, the compound represented by Chemical Formula 1 has a rigid structure in which four amine groups to which fluorene is bonded are connected to the spirobifluorene core, and thus has high thermal stability, so excellent performance when applied to devices has

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

In the present specification, when a part "includes" a certain component, this means that other components may be further included, rather than excluding other components, unless otherwise stated.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is preferably a compound having solubility in a suitable organic solvent.

In addition, in the case of the compound represented by Formula 1 according to an exemplary embodiment of the present specification, an organic light emitting device may be manufactured by a solution coating method, and thus a large area of the device may be possible.

As used herein, the term “curable group” refers to a “photocurable group” or “thermosetting group”, which may mean a reactive substituent for crosslinking between compounds by exposure to heat and/or light. Crosslinking may be generated by connecting radicals generated while decomposing carbon-carbon multiple bonds and cyclic structures by heat treatment or light irradiation.

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

In the present specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position to which the hydrogen atom is bonded, that is, a position where the substituent is substitutable, is not limited, 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” refers to deuterium; halogen group; nitrile group; silyl group; boron group; an alkyl group; cycloalkyl group; alkoxy group; aryl group; and substituted or unsubstituted by one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted in which two or more substituents among the above-exemplified substituents are connected. For example, "a substituent in which two or more 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 -SiRaRbRc, and Ra, Rb and Rc may each be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or the like. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of -BRdRe, and Rd and Re may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a tert-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but may be 1 to 60, and according to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 30, 1 to 20, or 1 to 10. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, etc., but these is not limited to

In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms, and according to another exemplary embodiment, the cycloalkyl group has 3 to 40, or 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 a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but may be 1 to 20 carbon atoms. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, n-propoxy group, n-butoxy group, tert-butoxy group, n-pentyloxy group, n-hexyloxy group, n-octyloxy group, n-no It may be a nyloxy group, an n-decyloxy group, or the like, but is not limited thereto.

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 another exemplary embodiment, the carbon number of the aryl group is 6 to 30, or 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

,

(스피로비플루오레닐기) 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,

,

spirofluorenyl groups such as (spirobifluorenyl group);

(9,9-dimethyl fluorenyl group), and

a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but may have 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include a pyridyl group, a pyrrole group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, etc. , but is not limited to these.

In the present specification, the description of the above-mentioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the description of the above-described aryl group is applied, except that the arylene group is a divalent group.

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

In the present specification, the description of the above-described cycloalkyl group is applied, except that the cycloalkylene group is a divalent group.

In the present specification, the description of the above-described heteroaryl group is applied, except that the heteroarylene group is a divalent group.

In the present specification, O in "-O-" means an oxygen atom, and - means a direct bond (single bond).

In the present specification, in "-S-", S means a sulfur atom, and - means a direct bond (single bond).

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 8.

[Formula 8]

In the formula (8),

L1 to L4, X1 to X4, Ar1 to Ar4, R1 to R8, a1 to a4, and n1 to n8 are as defined in Formula 1.

According to an exemplary embodiment of the present specification, the "-(L1) _a1 -X1, -(L2) _a2 -X2, -(L3) _a3 -X3 and -(L4) _a4 -X4" are each 9 times of fluorene bonded to carbon

The compound represented by Formula 1 introduces a curing group at the 9th carbon position of fluorene where the spirobifluorene core structure and the conjugation are broken, and the thin film of the portion leading to the core skeleton of fluorene and spirobifluorene to which the curing group is bonded Interference with the phase interaction can be reduced and undesirable effects on the molecular orbital function of the core skeleton can be minimized, so that an organic light emitting device having a longer lifespan can be manufactured.

In an exemplary embodiment of the present specification, Formula 1 is represented by Formula 2 below.

[Formula 2]

In Formula 2,

L1 to L4, X1 to X4, Ar1 to Ar4, R1 to R4, a1 to a4, and n1 to n4 are as defined in Formula 1,

R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m1 to m4 are each an integer of 0 to 7, and when m1 to m4 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, Chemical Formula 2 is represented by the following Chemical Formula 2-1.

[Formula 2-1]

L1 to L4, X1 to X4, Ar1 to Ar4, R1 to R4, a1 to a4, n1 to n4, R11 to R18, and m1 to m4 are as defined in Formula 2.

In the exemplary embodiment of the present specification, a1 to a4 are each an integer of 0 to 2, and when a1 to a4 are each 2, the substituents in parentheses are the same as or different from each other.

According to another exemplary embodiment, a1 to a4 are 0.

According to another exemplary embodiment, a1 to a4 are 1.

According to another exemplary embodiment, a1 to a4 are 2.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C 1 to C 10 alkylene group; a substituted or unsubstituted C 3 to C 30 cycloalkylene group; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; a substituted or unsubstituted C 2 to C 30 heteroarylene group; or -O-.

According to another exemplary embodiment, L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C 1 to C 5 alkylene group; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or -O-.

In another exemplary embodiment, L1 to L4 are the same as or different from each other, and each independently a direct bond; methylene group; phenylene group; or -O-.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 3 or 4.

[Formula 3]

[Formula 4]

In Formulas 3 and 4,

X1 to X4, Ar1 to Ar4, R1 to R4, and n1 to n4 are as defined in Formula 1,

R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m1 to m4 are each an integer of 0 to 7, and when m1 to m4 are each 2 or more, the substituents in parentheses are the same as or different from each other,

b1 to b4 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, b1 to b4 are 1.

According to an exemplary embodiment of the present specification, b1 to b4 are 0.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 5 to 7 below.

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7,

X1 to X4, Ar1 to Ar4, R1 to R4, and n1 to n4 are as defined in Formula 1,

R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m1 to m4 are each an integer of 0 to 7, and when m1 to m4 are each 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, X1 to X4 are the same as or different from each other, and are each independently a curable group.

According to an exemplary embodiment of the present specification, the curable group is any one of the following structures.

In the above structures,

L is a direct bond; -O-; -S-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R21 is hydrogen; Or a substituted or unsubstituted alkyl group,

k is 1 or 2.

는 다른 구조에 결합되는 위치를 의미한다.In the above structures,

denotes a position where it is bound to another structure.

In one embodiment of the present specification, L is a direct bond; -O-; -S-; a substituted or unsubstituted C1-C30 alkylene group; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

According to another exemplary embodiment, L is a direct bond; -O-; -S-; an alkylene group having 1 to 30 carbon atoms; an arylene group having 6 to 30 carbon atoms; or a heteroarylene group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R21 is hydrogen; or a substituted or unsubstituted C 1 to C 20 alkyl group.

According to another exemplary embodiment, R21 is hydrogen; or an alkyl group having 1 to 10 carbon atoms.

)을 사용하는 경우, 소자 내에 적용시 보다 우수한 효과를 나타낸다.According to an exemplary embodiment of the present specification, the curable group is styrene (

), it exhibits a better effect when applied within the device.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; Or a heterocyclic group having 2 to 60 carbon atoms including at least one of O, S and N as a substituted or unsubstituted heteroelement.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently has 6 to 60 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of a halogen group and an alkyl group having 1 to 10 carbon atoms. is the aryl group of

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group and an alkyl group having 1 to 10 carbon atoms; or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen group and an alkyl group having 1 to 10 carbon atoms.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently -F, a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and a propyl group; or -F, a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and a propyl group.

According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; or a heterocyclic group having 2 to 60 carbon atoms including at least one of O, S and N as a substituted or unsubstituted heteroelement.

According to another exemplary embodiment, R1 to R4 are hydrogen.

According to another exemplary embodiment, R5 to R8 are the same as or different from each other, and each independently represent a substituted or unsubstituted C6-C30 aryl group.

According to another exemplary embodiment, R5 to R8 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R5 to R8 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to another exemplary embodiment, R5 to R8 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, n1 to n4 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, n5 to n8 are each 0 to 2, and when n5 to n8 are 2 respectively, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present specification, R11 to R14 are hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; or a heterocyclic group having 2 to 60 carbon atoms including at least one of O, S and N as a substituted or unsubstituted heteroelement.

According to another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently represent a substituted or unsubstituted C6-C30 aryl group.

According to another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to another exemplary embodiment, R11 to R14 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R15 to R18 are hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; Or a heterocyclic group having 2 to 60 carbon atoms including at least one of O, S and N as a substituted or unsubstituted heteroelement.

According to another exemplary embodiment, R15 to R18 are hydrogen.

According to an exemplary embodiment of the present specification, m1 to m4 are 0 or 1, respectively.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following structures.

The compound represented by Formula 1 according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below.

For example, in Chemical Formula 2-1, which is an example of the compound represented by Chemical Formula 1, a core structure may be prepared as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

<Scheme 1>

The definition of the substituent in Scheme 1 is the same as in Formula 2-1.

In an exemplary embodiment of the present specification, there is provided a coating composition comprising a compound represented by the above-described formula (1).

In an exemplary embodiment of the present specification, the coating composition includes a compound represented by Formula 1 and a solvent.

In one embodiment of the present specification, the coating composition may be in a liquid state. The "liquid phase" means a liquid state at room temperature and pressure.

In one embodiment of the present specification, the solvent is, for example, a chlorine-based solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, 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; Polyvalents 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, and 1,2-hexanediol alcohols and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; A solvent such as tetralin is exemplified, but any solvent capable of dissolving or dispersing the compound of Formula 1 according to an exemplary embodiment of the present invention is sufficient, and the present invention is not limited thereto.

In another exemplary embodiment, the solvent may be used alone or as a mixture of two or more solvents.

In one embodiment of the present specification, the coating composition does not further include a p-doping material.

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

In the present specification, the p-doped material refers to a material that allows the host material to have p-semiconductor properties. The p-semiconductor property refers to the property of receiving or transporting holes at the highest occupied molecular orbital (HOMO) energy level, that is, the property of a material having high hole conductivity.

In the present specification, the p-doping material is sufficient as long as it has a p-semiconductor characteristic, and one or two or more types may be used, and the type thereof is not limited.

In an exemplary embodiment of the present specification, the content of the p-doping material is 0% to 50% by weight based on the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the content of the p doping material includes 0 to 30% by weight based on the total solid content of the coating composition. In an exemplary embodiment of the present specification, the content of the p-doping material is preferably 1 to 30% by weight based on the total solid content of the coating composition, and in another exemplary embodiment, the p-doping material It is more preferable that the content of the coating composition comprises 10 to 30% by weight based on the total solid content of the coating composition.

In another embodiment, the coating composition is a single molecule comprising a thermosetting group or a photocurable group; Alternatively, it may further include a single molecule including a terminal group capable of forming a polymer by heat. Monomolecules containing a thermosetting group and a photocurable group as described above; Alternatively, the molecular weight of a single molecule including a terminal group capable of forming a polymer by heat may be a compound of 4,000 g/mol or less.

In an exemplary embodiment of the present specification, the coating composition has a molecular weight of 4,000 g/mol or less, and a single molecule including a thermosetting group and/or a photocurable group; Or it further includes a monomolecular containing a terminal group capable of forming a polymer by heat.

a single molecule comprising the thermosetting group or the photocurable group; Or a single molecule including a terminal group capable of forming a polymer by heat is an aryl of phenyl, biphenyl, fluorene, or naphthalene; arylamine; Alternatively, it may refer to a single molecule in which fluorene is substituted with a thermosetting group, a photocurable group, or a terminal group capable of forming a polymer by heat.

In another embodiment, the viscosity of the coating composition is 2 cP to 15 cP. When the above viscosity is satisfied, it is easy to manufacture a cleaning agent.

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

In one embodiment of the present specification, 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 organic material layer includes the coating composition or a cured product thereof.

The cured product of the coating composition is in a state in which the coating composition is cured by heat treatment or light treatment.

In an exemplary embodiment of the present specification, the organic material layer including the coating composition or a cured product thereof is a hole injection layer. The compound represented by Formula 1 includes four amines in the compound, and thus the HOMO level is high and is suitable for the hole injection layer.

In an exemplary embodiment of the present specification, the organic material layer including the coating composition or a cured product thereof is a hole transport layer, a light emitting layer, an electron transport layer or an electron injection layer.

In an exemplary embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer, a layer for hole injection and hole transport at the same time, an electron transport layer, an electron injection layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer It further includes one or more layers selected from the group consisting of a layer and a hole blocking layer.

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

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

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

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

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention is an organic material layer, a hole injection layer, a hole transport layer, a layer that injects and transports holes at the same time, a light emitting layer, an electron transport layer, an electron injection layer, a layer that injects and transports electrons at the same time, an electron blocking layer , and may have a structure including a hole blocking layer. 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 the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIG. 1 .

1, an anode 201, a hole injection layer 301, a hole transport layer 401, a light emitting layer 501, a layer 601 for injecting and transporting electrons at the same time, and a cathode 701 are sequentially shown on a substrate 101 The structure of the organic light emitting device stacked with

1 illustrates an organic light emitting device, but is not limited thereto.

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

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one of the organic material layers is formed using a coating composition including the compound represented by Formula 1 above.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and forming an organic material layer including at least one of a hole injection layer, a hole transport layer, a light emitting layer, and a layer that simultaneously injects and transports electrons thereon, and then deposits a material that can be used as a cathode thereon. .

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

Specifically, in one embodiment of the present specification, preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer includes forming one or more organic material layers using the coating composition.

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

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

In the present specification, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited thereto.

Since the coating composition according to an exemplary embodiment of the present specification is suitable for a solution process due to its structural characteristics, it can be formed by a printing method, thereby having an economical effect in terms of time and cost in manufacturing the device.

In an exemplary embodiment of the present specification, the step of forming one or more organic material layers using the coating composition comprises: coating the coating composition on the first electrode or one or more organic material layers; and heat-treating or light-treating the coated coating composition.

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

In another exemplary embodiment, the heat treatment time in the heat treatment step is 1 minute to 2 hours, according to an exemplary embodiment may be 1 minute to 1 hour, in another exemplary embodiment, 30 minutes to It can be 1 hour.

When the step of forming the organic material layer formed using the coating composition includes the heat treatment or light treatment step, a plurality of the compounds included in the coating composition form cross-linking to provide an organic material layer including a thinned structure. In this case, when another layer is laminated on the surface of the organic material layer formed by using the coating composition, it can be prevented from being dissolved, morphologically affected, or decomposed by a solvent.

Therefore, when the organic material layer formed by using the coating composition is formed including a heat treatment or light treatment step, resistance to solvents increases, so that a multilayer can be formed by repeatedly performing solution deposition and crosslinking methods, and stability of the device is increased Lifespan characteristics can be increased.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, 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 metal and oxide such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is a substituted or unsubstituted derivative. It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. do. Specific examples include 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 transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, 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-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

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

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

< manufacturing example >

manufacturing example 1. Synthesis of Compound A

A-Int synthesis: L1 (7.00 g, 15.5 mmol), aniline (3.54 mL, 38.8 mmol) and NaOtBu (2.24 g, 23.3 mmol) were placed in a round bottom flask (RBF), and toluene (150 mL) was added thereto. After adding Pd( ^t Bu ₃ P) ₂ (0.396 g, 0.775 mmol), the mixture was stirred at 80° C. for 1 hour. Then, water was added, the organic layer was extracted with ethyl acetate (EA), dried over MgSO ₄ , and purified by ethyl acetate/hexane column to obtain A-Int (6.00 g).

Synthesis A: 2,2',7,7'-tetrabromo-9,9'-spirobi[fluorene] (1.00 g, 1.58 mmol), A-Int (3.30 g, 7.12 mmol), NaOtBu (0.304 g, 3.17 mmol) ) was put in RBF, and toluene (30 mL) was added. After raising the temperature to 100 °C, Pd( ^t Bu ₃ P) ₂ (0.0674 g, 0.132 mmol) was added and stirred for 5 hours. Water was added, and the organic layer was extracted with dichloromethane (DCM), dried over MgSO ₄ , and purified by dichloromethane/hexane column to obtain high purity Compound A (1.62) g) was obtained. [M+H] ⁺ =2162

¹ H NMR: δ 7.66 - 7.65 (m, 4H), 7.54 - 7.53 (m, 4H), 7.43 - 7.41 (m, 4H), 7.36 - 7.34 (m, 4H), 7.30 - 7.28 (m, 4H), 7.24 - 7.21 (m, 12H), 7.15 - 7.07 (m, 20H), 6.90 - 6.88 (m, 28H), 6.84 - 6.83 (m, 4H), 6.69 - 6.63 (dd, 4H), 6.61 - 6.60 (m) , 4H), 5.71 - 5.67 (d, 4H), 5.20 - 5.18 (d, 4H), 2.11 - 2.10 (m, 12H), 1.53 (br s, 12H).

manufacturing example 2. Synthesis of compound B

B-Int synthesis: L2 (5.00 g, 8.75 mmol), 4-fluoroaniline (2.07 mL, 21.9 mmol) and NaOtBu (1.26 g, 13.1 mmol) were placed in RBF, and toluene (87 mL) was added thereto. Pd(^tBu₃P)₂ (0.224 g, 0.437 mmol) was added and stirred at 90 °C for 1 hour. After adding water and extracting the organic layer with ethyl acetate (EA), MgSO₄It was dried with ethyl acetate/hexane column and purified to obtain B-Int (3.57 g).

Synthesis B: 2,2',7,7'-tetrabromo-9,9'-spirobi[fluorene] (0.800 g, 1.27 mmol), B-Int (3.32 g, 5.70 mmol), NaOtBu (0.243 g, 2.53 mmol) ) was put in RBF, and toluene (25 mL) was added. After raising the temperature to 100 °C, Pd( ^t Bu ₃ P) ₂ (0.0453 g, 0.089 mmol) was added and stirred for 6 hours. Thereafter, water was added, the organic layer was extracted with dichloromethane (DCM), dried over MgSO ₄ , and purified by dichloromethane/hexane column to obtain high-purity compound B (1.72). g) was obtained. [M+H] ⁺ =2714

¹ H NMR: δ 7.67 - 7.66 (m, 4H), 7.52 - 7.50 (m, 4H), 7.39 - 7.38 (m, 4H), 7.36 - 7.34 (m, 4H), 7.32 - 7.31 (m, 8H), 7.29 - 7.25 (m, 4H), 7.24 - 7.21 (m, 12H), 7.18 - 7.07 (m, 20H), 6.92 - 6.88 (m, 28H), 6.82 - 6.81 (m, 4H), 6.74 - 6.73 (m) , 8H), 6.70 - 6.65 (dd, 4H), 6.61 - 6.60 (m, 4H), 5.75 - 5.72 (d, 4H), 5.21 - 5.19 (d, 4H), 1.34 (br s, 36H).

manufacturing example 3: Synthesis of compound C

C-Int synthesis: L3 (6.00 g, 13.3 mmol), 4'-propyl-[1,1'-biphenyl]-4-amine (7.02 g, 33.2 mmol) and NaOtBu (1.92 g, 19.9 mmol) were placed in RBF, and toluene (133 mL) was added thereto. After adding Pd( ^t Bu ₃ P) ₂ (0.340 g, 0.665 mmol), the mixture was stirred at 90° C. for 1 hour. Water was added, and the organic layer was extracted with ethyl acetate (EA), dried over MgSO ₄ , and purified by ethyl acetate/hexane column to obtain C-Int (5.41 g).

Synthesis of C: 2,2',7,7'-tetrabromo-9,9'-spirobi[fluorene] (0.900 g, 1.42 mmol), C-Int (3.73 g, 6.41 mmol), NaOtBu (0.273 g, 2.85 mmol) ) was put in RBF, and toluene (28 mL) was added. After the temperature was raised to 100 °C, Pd( ^t Bu ₃ P) ₂ (0.0509 g, 0.100 mmol) was added and stirred for 6 hours. Then, water was added, and the organic layer was extracted with dichloromethane (DCM), dried over MgSO ₄ , and purified by dichloromethane/hexane column to obtain high purity Compound C (1.88). g) was obtained. [M+H] ⁺ =2634

¹ H NMR: δ 7.68 - 7.67 (m, 4H), 7.55 - 7.54 (m, 4H), 7.51 - 7.50 (m, 4H), 7.38 - 7.37 (m, 8H), 7.33 - 7.31 (m, 4H), 7.30 - 7.28 (m, 4H), 7.26 - 7.22 (m, 12H), 7.19 - 7.11 (m, 20H), 7.04 - 7.03 (m, 8H), 6.98 - 6.94 (m, 28H), 6.85 - 6.83 (m) , 4H), 6.71 - 6.67 (dd, 4H), 6.66 - 6.65 (m, 4H), 6.00 - 5.97 (d, 4H), 5.32 - 5.30 (d, 4H), 3.58 - 3.57 (d, 4H), 3.31 - 3.30 (d, 4H), 2.59 - 2.57 (t, 8H), 2.21 - 2.18 (m, 12H), 1.56 - 1.55 (m, 8H), 1.05 - 1.04 (t, 12H)

< Example >

Example One

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone and dried. After washing the substrate for 5 minutes, the substrate was transported to a glove box.

On the ITO transparent electrode prepared as described above, 1.5 wt% cyclohexanone ink containing the compound A prepared in Preparation Example 1 and the following compound P in a weight ratio of 8:2 (compound A:compound P) was spin-coated on the ITO surface. and heat treatment (curing) at 220° C. for 30 minutes to form a hole injection layer with a thickness of 30 nm. A hole transport layer was formed to a thickness of 40 nm by spin coating 2 wt% toluene ink of the following α-NPD compound on the hole injection layer. Thereafter, after transferring to a vacuum evaporator, the weight ratio (ADN:DPAVBi) of the following ADN compound and the following DPAVBi compound was 20:1 on the hole transport layer, and vacuum deposition was performed to a thickness of 20 nm to form a light emitting layer. On the light emitting layer, the following BCP compound was vacuum-deposited to a thickness of 35 nm to form a layer that simultaneously injects and transports electrons. A cathode was formed by sequentially depositing LiF with a thickness of 1 nm and aluminum with a thickness of 100 nm on the layer for simultaneously injecting and transporting electrons.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2×10 ^-7 ~ 5×10 ^-6 torr was maintained.

< Example 2>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound A.

< Example 3>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound C was used instead of Compound A.

< comparative example 1>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound was used instead of Compound A.

< comparative example 2>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound was used instead of Compound A.

The driving voltage, external quantum efficiency (EQE), and lifetime were measured at a current density of ^{10 mA/cm 2} for the organic light emitting devices prepared in Examples and Comparative Examples, and the results are shown in Table 1 below. It was. The external quantum efficiency was calculated as (number of emitted photons)/(number of injected charge carriers). T95 denotes a time required for the luminance to decrease from the initial luminance (1000 nit) to 95%.

Driving voltage (V) EQE (%) T95(hr) Example 1 4.10 6.13 110 Example 2 4.23 5.98 98 Example 3 4.06 6.05 120 Comparative Example 1 not measurable not measurable not measurable Comparative Example 2 4.85 4.41 57

Examples 1 to 3 in which an organic material layer was formed using the compound of the present application had lower driving voltage and excellent external quantum efficiency and lifespan characteristics than Comparative Examples 1 and 2 in which an organic material layer was formed using a compound having a structure different from the present compound. can be checked

Specifically, the compound used in Comparative Example 1 has four amine groups bonded with the spirobifluorene core as the center, but does not include a curable group, so the resistance to the solvent used in the subsequent process (hole transport layer forming process) step is low. and, due to this, it is mixed with the hole injection layer material in a subsequent process step, and thus a stable device cannot be obtained.

In Comparative Example 2, four amine groups are bonded to the spirobifluorene core as the center, but by using a compound in which fluorene is not bonded as a substituent of the amine group in the device, the device characteristics than Examples 1 to 3 of the present application It can be seen that this is low.

101: substrate
201: anode
301: hole injection layer
401: hole transport layer
501: light emitting layer
601: layer that simultaneously injects and transports electrons
701: cathode

Claims (16)

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

In Formula 1,
L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted heteroarylene group; or -O-;
Ar1 to Ar4 and R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
X1 to X4 are the same as or different from each other, and each independently a curable group,
a1 to a4 are each an integer of 0 to 5, and when a1 to a4 are each 2 or more, the substituents in parentheses are the same as or different from each other,
n1 to n4 are each an integer of 0 to 3, n5 to n8 are each an integer of 0 to 8, and when n1 to n8 are each 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
The compound of Formula 1 is represented by Formula 2 below:
[Formula 2]

In Formula 2,
L1 to L4, X1 to X4, Ar1 to Ar4, R1 to R4, a1 to a4, and n1 to n4 are as defined in Formula 1,
R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m1 to m4 are each an integer of 0 to 7, and when m1 to m4 are each 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
The compound of formula 1 is represented by the following formula 3 or 4:
[Formula 3]

[Formula 4]

In Formulas 3 and 4,
X1 to X4, Ar1 to Ar4, R1 to R4, and n1 to n4 are as defined in Formula 1,
R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m1 to m4 are each an integer of 0 to 7, and when m1 to m4 are each 2 or more, the substituents in parentheses are the same as or different from each other,
b1 to b4 are 0 or 1, respectively. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 5 to 7:
[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7,
X1 to X4, Ar1 to Ar4, R1 to R4, and n1 to n4 are as defined in Formula 1,
R11 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m1 to m4 are each an integer of 0 to 7, and when m1 to m4 are each 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 1,
The compound of Formula 1 is represented by the following Formula 8:
[Formula 8]

In the formula (8),
L1 to L4, X1 to X4, Ar1 to Ar4, R1 to R8, a1 to a4, and n1 to n8 are as defined in Formula 1. 3. The method according to claim 2,
The compound of Formula 2 is represented by the following Formula 2-1:
[Formula 2-1]

L1 to L4, X1 to X4, Ar1 to Ar4, R1 to R4, a1 to a4, n1 to n4, R11 to R18, and m1 to m4 are as defined in Formula 2. The method according to claim 1,
A compound wherein the curable group is any one of the following structures:

In the above structures,
L is a direct bond; -O-; -S-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R21 is hydrogen; Or a substituted or unsubstituted alkyl group,
k is 1 or 2. The method according to claim 1,
The compound of Formula 1 is represented by any one of the following structures:

. A coating composition comprising a compound according to any one of claims 1 to 8. The coating composition of claim 9 , wherein the coating composition further comprises a p-doping material. a first electrode;
a second electrode; and
At least one organic material layer provided between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic light emitting device comprising the coating composition of claim 9 or a cured product thereof. 12. The method of claim 11,
The cured product of the coating composition is an organic light emitting device in a state in which the coating composition is cured by heat treatment or light treatment. 12. The method of claim 11,
The organic material layer including the coating composition or a cured product thereof is an organic light emitting device that is a hole injection layer. preparing a substrate;
forming a first electrode on the substrate;
forming one or more organic material layers on the first electrode; and
Forming a second electrode on the organic material layer,
The step of forming the organic material layer is a method of manufacturing an organic light emitting device comprising the step of forming one or more organic material layer using the coating composition of claim 9. 15. The method of claim 14,
The step of forming one or more organic material layers using the coating composition is a method of manufacturing an organic light emitting device using a spin coating method. 15. The method of claim 14,
The step of forming one or more organic material layers using the coating composition
coating the coating composition on the first electrode or one or more organic material layers; and
Method of manufacturing an organic light emitting device comprising the step of heat-treating or light-treating the coated coating composition.

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