KR20180092783A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

Provided in the present specification are a compound and an organic light emitting device comprising the same. The compound of the present invention is represented by chemical formula 1. When a coating composition containing the compound according to an embodiment of the present invention is used, a solution process is possible, and the device can be made larger.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic light-

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.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

In addition to the above, it is preferable that the material used in the organic light emitting device further has the following properties.

First, the material used in the organic light emitting device is preferably excellent in thermal stability. This is because joule heating occurs due to the movement of charges in the organic light emitting device. NPB, which is mainly used as a hole transport layer material, has a glass transition temperature of 100 ° C or less, which is a problem that is difficult to use in an organic light emitting device requiring a high current.

Secondly, in order to obtain a highly efficient organic light emitting device capable of driving at a low voltage, holes or electrons injected into the organic light emitting element should be smoothly transferred to the light emitting layer, and injected holes and electrons should not escape from the light emitting layer. For this purpose, the material used in the organic light emitting device should have an appropriate band gap and a HOMO or LUMO energy level. In the case of PEDOT: PSS used as a hole transport material in the organic light emitting device manufactured by the solution coating method, since the LUMO energy level is lower than the LUMO energy level of the organic material used as the light emitting layer material, There is a difficulty in.

In addition, materials used in organic light emitting devices should have excellent chemical stability, charge mobility, and interface characteristics with electrodes or adjacent layers. That is, the material used in the organic light emitting device should have little deformation of the material due to moisture or oxygen. In addition, by having appropriate hole or electron mobility, it is necessary to maximize the formation of excitons by balancing the density of holes and electrons in the light emitting layer of the organic light emitting device. And, for the stability of the device, the interface with the electrode including the metal or the metal oxide should be good.

Accordingly, there is a need in the art to develop organic materials having the above-mentioned requirements.

Korean Patent Publication No. 2012-0112277

The present invention provides a compound, a coating composition containing the same, and an organic light emitting device comprising the same.

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

[Chemical Formula 1]

In Formula 1,

L1 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylarylene group and a substituted or unsubstituted arylalkylene group,

L2 and L3 each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group,

Ar 1 to Ar 4 each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, or adjacent substituents may be mutually bonded to form a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group In addition,

Y1 to Y6 each independently represent hydrogen; Or a heat or light polymerization functional group, at least one of which is a heat or light polymerization functional group,

a to f are each independently an integer of 0 or 1,

The sum of a to f is 2 to 6.

In addition, one embodiment of the present disclosure provides a coating composition comprising the compound.

One embodiment of the present disclosure is an organic light emitting device comprising a cathode, an anode, and at least one organic layer disposed between the cathode and the anode, wherein at least one of the organic layers comprises the coating composition. A light emitting device is provided.

When a coating composition containing a compound according to one embodiment of the present invention is used, a solution process can be performed, and the device can be made larger.

The compound according to one embodiment of the present invention can be used as an organic layer material of an organic light emitting device and can provide a low driving voltage, a high luminous efficiency and a high lifetime characteristic.

The organic layer formed using the compound according to one embodiment of the present specification has excellent thermal stability.

1 shows an example of an organic light emitting device according to an embodiment of the present invention.
2 to 7 are MS data for confirming that a compound according to one embodiment of the present invention has been produced.
8 to 10 are data obtained by measuring the results using the compound and the comparative compound according to one embodiment of the present invention.

Hereinafter, the present specification will be described in detail.

When a member is referred to herein as being " on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as " comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

Throughout this specification, the term " combination thereof " included in the expression of the machine form means one or more combinations or combinations selected from the group consisting of the constituents described in the expression of the machine form, ≪ / RTI > are meant to include one or more selected from the group consisting of

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

In one embodiment of the present invention, Y1 to Y6 each independently represent hydrogen; Or a heat or light polymerization functional group, and at least one of them is a heat or light polymerization functional group. A heat or light polymerization functional group can mean a polymerizable functional group, by heat or light.

As used herein, the term " thermal or light-polymerizable functional group " may mean a reactive substituent that undergoes polymerization between compounds by exposure to heat or light. Polymerization can be produced by heat treatment or irradiation of light, connecting carbon-carbon multiple bonds, radicals formed by decomposition of the cyclic structure.

In one embodiment of the present disclosure, the heat or light polymerization functional group is any one of the following structures.

In the above structural formula, R 1 is selected from the group consisting of hydrogen and a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R 1 is hydrogen or an alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, R 1 is hydrogen or an alkyl group having 1 to 10 carbon atoms.

In the case of a compound containing a thermal or light-polymerizable functional group as in the embodiment of the present invention, an organic light emitting device can be manufactured by a solution coating method, which is economical in terms of time and cost.

Further, in the case of forming a coating layer using a coating composition comprising a compound containing a thermal or light-polymerizing functional group, since a polymerizable functional group is polymerized by heat or light, an additional layer is laminated on the coating layer It is possible to prevent the compound contained in the coating composition from being washed out by the solvent, so that an additional layer can be laminated on the top while maintaining the coating layer.

In addition, when a heat or light polymerization functional group forms a polymerization to form a coating layer, the coating layer has an increased chemical resistance to a solvent and a high film retention ratio.

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.

According to one embodiment of the present invention, in the case of a compound in which polymerization is carried out by heat treatment or light treatment, since a plurality of compounds are polymerized to be provided in a thin film form in an organic light emitting device, the compound has an excellent thermal stability. Therefore, the organic light emitting device using the compound according to one embodiment of the present invention has an excellent lifetime characteristic.

In addition, since the compound according to one embodiment of the present invention includes an amine structure in the core structure, it can have an appropriate energy level and band gap as a hole injecting, hole transporting material, or light emitting material in an organic light emitting device. In addition, by controlling the substituent of the compound of Chemical Formula 1 according to one embodiment of the present invention, it is possible to control the appropriate energy level and bandgap finely, improve the interfacial characteristics between the organic materials, Can be provided.

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 substituted, two or more substituents may be the same or different from each other.

As used herein, the term " substituted or unsubstituted " heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An alkyl group; An alkoxy group; An alkenyl group; An aryl group; An amine 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, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear, branched or cyclic, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 3-methylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, Cyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2- Propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like. .

The alkyl group may be substituted with an aryl group or a heteroaryl group, and may function as an arylalkyl group or a heteroarylalkyl group. The aryl group and the heteroaryl group may be selected from the following examples of the aryl group or the heterocyclic group.

In the present specification, the length of the alkyl group does not affect the conjugation length of the compound, and may affect the application of the compound to an organic light emitting device application method such as a vacuum deposition method or a solution application method.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

The alkoxy group may be substituted with an aryl group or a heteroaryl group, and may function as an aryloxy group or a heteroaryloxy group. The aryl group and the heteroaryl group may be selected from the following examples of the aryl group or the heterocyclic group.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

The alkenyl group may be substituted with an aryl group or a heteroaryl group to act as an arylalkenyl or heteroarylalkenyl group. The aryl group and the heteroaryl group may be selected from the following examples of the aryl group or the heterocyclic group.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

및

,

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

And

,

And the like. However, the present invention is not limited thereto.

The aryl group may be substituted with an alkyl group to act as an arylalkyl group. The alkyl group may be selected from the examples described above.

In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, a thiazolyl group, Group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine A phenanthrene group, a phenylmethyl group, a phenylmethyl group, a phenylmethyl group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, , Triphenylamine group and the like, but are not limited thereto.

In the present specification, the alkylene group may be selected from the examples of the alkyl group described above, except that it is a divalent group.

In the present specification, the arylene group may be selected from the examples of the aryl group described above, except that it is a divalent group.

As used herein, the term " adjacent " means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.

In the present specification, the ring formed by bonding adjacent groups to each other may be monocyclic or polycyclic, and may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and may form a hydrocarbon ring or a heterocyclic ring.

The hydrocarbon ring may be selected from the examples of the cycloalkyl group or the aryl group except that the hydrocarbon ring is not the monovalent group. The heterocyclic ring may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and examples thereof may be selected from the heterocyclic groups except that the heterocyclic group is not a monovalent group.

In one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylarylene group and a substituted or unsubstituted arylalkylene group.

Also, in one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; A substituted or unsubstituted alkylarylene group having 6 to 30 carbon atoms and a substituted or unsubstituted arylalkylene group having 6 to 30 carbon atoms.

In one embodiment of the present disclosure, L1 is selected from the following formulas.

X is selected from the group consisting of O, S, SO ₂ , SO, Se and SeO ₂ , and n is an integer of 1 to 6.

In one embodiment of the present specification, L2 and L3 each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present invention, L2 and L3 each independently represent 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.

Further, in one embodiment of the present specification, L2 and L3 each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

Further, in one embodiment of the present specification, L2 and L3 are each independently a substituted or unsubstituted phenylene group.

Further, in one embodiment of the present specification, L2 and L3 are each independently a phenylene group.

In one embodiment of the present invention, Ar 1 to Ar 4 each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, or adjacent substituents may be mutually bonded to form a substituted or unsubstituted arylene group or a substituted Or an unsubstituted heteroarylene group.

In one embodiment of the present invention, Ar 1 to Ar 4 each independently represent 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, To form 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.

Ar 1 to Ar 4 each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, Ar1 to Ar4 each independently represent a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted fluorenyl group.

Further, in one embodiment of the present specification, Ar1 to Ar4 each independently represent a substituted or unsubstituted biphenylene group or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present invention, Ar 1 to Ar 4 are each independently a biphenylene group or a fluorenyl group substituted with a methyl group.

In one embodiment of the present invention, the compound represented by Formula 1 is selected from the following structural formulas.

The present disclosure also provides coating compositions comprising the aforementioned compounds.

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

In one embodiment of the present invention, the coating composition may further include one or two compounds selected from the group consisting of a compound having a polymerizable functional group introduced into the molecule and a polymer compound.

In one embodiment of the present disclosure, the coating composition may further comprise a compound into which a polymerizable functional group is introduced into the molecule. When the coating composition further contains a compound having a functional group capable of polymerizing in the molecule, the degree of curing of the coating composition can be further increased.

According to one embodiment of the present disclosure, the molecular weight of the compound into which the polymerizable functional group is introduced into the molecule is from 100 g / mol to 3,000 g / mol. In another embodiment of the present invention, the molecular weight of the compound into which the polymerizable functional group is introduced in the molecule is more preferably from 500 g / mol to 2,000 g / mol.

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

In one embodiment of the present disclosure, the viscosity of the coating composition is between 2 cP and 15 cP. When having a viscosity in the above range, it is easy to manufacture the device.

In one embodiment of the present invention, the molecular weight of the polymer compound is 10,000 g / mol to 200,000 g / mol.

In one embodiment of the present specification, the polymer compound may further include a polymerizable functional group.

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, ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; Examples of polyhydric alcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, Alcohols and their derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethylsulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; A solvent such as tetralin may be exemplified, but a solvent capable of dissolving or dispersing the compound 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 yet another embodiment, the coating composition further comprises a p-doping material.

In the present specification, the p-doped material may promote thermal curing or light curing.

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 (2) to (5).

(2)

In formula (2)

A1 to A6 are the same or different from each other, and each independently hydrogen; A nitrile group; A nitro group; Amide group; Carbonyl group; A substituted or unsubstituted sulfonyl group; A substituted or unsubstituted ester group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic ring, or is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,

 (3)

In formula (3)

Y8 to Y11 are the same or different from each other, and are each independently CR or N,

A7 and A8 are the same or different from each other, and each independently hydrogen; A nitrile group; -CF _3; Or -COOA13,

R and A9 to A13 are the same or different from each other, and each independently hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; An unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,

[Chemical Formula 4]

In Formula 4,

Y < 7 > are the same or different from each other, and each independently CR &

R 'and A14 to A25 are the same or different from each other, and each independently hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted silyl group; A substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,

[Chemical Formula 5]

In formula (5)

A26 to A43 are the same or different from each other and each independently represents hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted heterocyclic group or a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring by bonding with adjacent substituents.

In one embodiment of the present invention, A 1 to A 6 are the same or different from each other, and each independently represents a nitrile group; A nitro group; A substituted or unsubstituted sulfonyl group (SO ₂ Ra); A substituted or unsubstituted alkenyl group; Or a substituted or unsubstituted aryl group.

The Ra represents a substituted or unsubstituted aryl group.

In another embodiment, each of A 1 to A 6 is an alkenyl group substituted with a nitrile group.

In another embodiment of the present invention, each of A1 to A6 is a nitro group; Or an aryl group substituted with a nitrile group.

In another embodiment, A1 to A6 are each a nitro group; Or a phenyl group substituted with a nitrile group.

In one embodiment of the present invention, the compound represented by Formula 2 may be represented by any one of the following Formulas 2-1 to 2-6.

2-1 2-2

(2-3) 2-4

2-5 2-6

In one embodiment of the present specification, A14 and A15 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present specification, A14 and A15 are bonded to each other to form a benzene ring.

In one embodiment of the present specification, A18 and A19 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present invention, A18 and A19 are bonded to each other to form a benzene ring.

In one embodiment of the present specification, A20 and A21 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In one embodiment of the present invention, A20 and A21 are bonded to each other to form a benzene ring.

In one embodiment of the present disclosure, Y7 is N.

In one embodiment of the present invention, the compound represented by Formula 4 may be represented by the following Formulas 4-1 to 4-3.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

In formulas (4-1) to (4-3)

Y < 7 > are the same or different from each other, and each independently CR &

R ', A14 to A19 and A22 to A25 are the same as defined in formula (4)

A44 to A59 are the same as or different from each other, and each independently is the same as defined in A14 to A25,

A14 'to A25' are the same or different from each other, and each independently hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted silyl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, the p-doped material may be represented by a conductive dopant of the following structure, but is not limited thereto. When the conductive dopant is included, it may mean a dopant that increases the conductivity of the organic material layer formed using the compound represented by Chemical Formula (1).

In one embodiment of the present invention, the conductive dopant may be represented by any one of the following formulas (7-1) to (7-11).

[Formula 7-1]

[Formula 7-2]

[Formula 7-3]

[Chemical Formula 7-4]

[Formula 7-5]

[Formula 7-6]

[Formula 7-7]

[Formula 7-8]

[Formula 7-9]

[Formula 7-10]

[Formula 7-11]

In another embodiment, the p-doping material includes, but is not limited to, metal oxides such as MoO ₂ (acac) ₂ , VO (acac) ₂ , V (acac) 3 or WO 3.

In another embodiment, the p-doping material is a halide such as AgBF ₄ , InCl ₃ , FeCl ₃ , GaCl ₃ , SbCl ₅ , AlCl ₃ , BF ₃ , I ₂ or Na ₂ IrCl ₆ , I never do that.

In another embodiment, the p-doping material may comprise a sulfonic acid compound or a compound comprising a boron anion as the ionic compound.

In another embodiment, the p-doping material may be, but is not limited to, a compound comprising a cyano group, for example, a compound of the following structure.

In another embodiment, the p-doping material may be a polymer material of polystyrene sulfonate (PSS), but is not limited thereto.

In another embodiment, the p-doping material may be, but is not limited to, Ce (NH ₄ ) ₂ (NO ₃ ) ₆ or [FeCp ₂ ] PF ₆ .

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 total compound.

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 from 1 to 10% by weight, based on the total solids content of the coating composition.

In yet another embodiment, the coating composition comprises a monomolecule comprising a polymerizable functional group; Or a monomer capable of forming a polymer by heat. A single molecule containing a polymerizable functional group as described above; Or a molecular weight of a monomolecule including an end group capable of forming a polymer by heat can be 2,000 g / mol or less.

As in one embodiment herein, the coating composition comprises a monomolecule comprising a polymerizable functional group; Or a monomolecule comprising a terminal group capable of forming a polymer by thermal polymerization, it is more preferable that the curing temperature can be lowered, and it is composed of similar structures that do not affect the physical properties of the compound of the present invention.

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

Monomers comprising said polymerizable functional groups; Or monomers comprising a terminal group capable of forming a polymer by thermal polymerization include aryl, such as phenyl, biphenyl, fluorene, naphthalene; Arylamine; Or a monomolecule in which a terminal group capable of forming a polymerizable functional group or a polymer by heat is substituted for a carbazole.

The polymerizable functional groups are the same as described above.

Further, in one embodiment of the present specification, the monomers containing the polymerizable functional group have the following structures, but are not limited as long as the properties of the coating composition of the present specification are not impaired.

In another embodiment, the monomolecule comprising a terminal group capable of forming a polymer by thermal treatment has the following structures, but is not limited thereto, so long as the properties of the coating composition of the present specification are not impaired.

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

In one embodiment of the present disclosure, a cathode; Anode; And one or more organic layers provided between the cathode and the anode, wherein at least one of the organic layers is formed using the coating composition.

In one embodiment of the present invention, the organic material layer formed using the coating composition is a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes.

In another embodiment, the organic layer formed using the coating composition is a light emitting layer.

In another embodiment, the organic compound layer formed using the coating composition is a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host of the light emitting layer.

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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

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

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material 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 an organic light emitting device according to one embodiment of the present specification is illustrated in FIG.

1 shows an organic light emitting device in which an anode 201, a hole injecting layer 301, a hole transporting layer 401, a light emitting layer 501, an electron transporting layer 601 and a cathode 701 are sequentially stacked on a substrate 101 Are illustrated.

1, the hole injecting layer 301, the hole transporting layer 401, and the light emitting layer 501 are formed using a coating composition comprising a compound represented by Chemical Formula (1).

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 represented by the above formula (1).

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, 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 cathode or an anode on the substrate; Forming at least one organic material layer on the cathode or the anode; And forming an anode or a cathode on the organic material layer, wherein at least one of the organic material layers is formed using the coating composition.

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

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

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

In another embodiment, the organic layer formed using the coating composition is formed by an ink-jet method.

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 an organic layer formed using the coating composition comprises: coating the coating composition on the cathode or the anode; And heat treating or light treating the coated coating composition.

In one embodiment of the present invention, the heat treatment temperature in the heat treatment step is 230 占 폚 or lower, more specifically 85 占 폚 to 230 占 폚.

In another embodiment, the heat treatment time in the heat treatment step may be from 1 minute to 1 hour.

In one embodiment of the present disclosure, when the coating composition contains no additive, it is preferred that the polymerization proceed by heat treatment at a temperature of 85 ° C to 230 ° C, and polymerization proceeds at a temperature of 85 ° C to 200 ° C . In addition, the coating compositions herein may further comprise initiators, but are more preferably not used.

When the heat treatment or the light treatment step is included in the step of forming the organic material layer formed using the coating composition, a plurality of compounds represented by the formula (1) contained in the coating composition may form a polymer and form an organic material layer Can 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.

Accordingly, when the organic compound layer formed using the coating composition is formed by a heat treatment or a light treatment step, the resistance to a solvent is increased, so that a multi-layer can be formed by repeating solution deposition and polymerization methods, The lifetime characteristics of the device can be increased.

In one embodiment of the present invention, the coating composition comprising the compound represented by Formula 1 may be used in the form of a coating composition prepared by mixing and dispersing a polymer binder.

In one embodiment of the present invention, the polymer binder is preferably one that does not extremely inhibit charge transport, and that does not strongly absorb visible light. Examples of the polymeric binder include poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylenevinylene) and derivatives thereof, poly (2,5-thienylenevinylene) A derivative thereof, a polycarbonate, a polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.

The compound represented by the general formula (1) according to one embodiment of the present invention includes a carbazole and an amine group, so that the compound represented by the general formula (1) may be contained in the organic material layer alone or the coating The composition may be thinned through heat treatment or light treatment, or may be incorporated as a copolymer using a coating composition mixed with other monomers. In addition, it can be incorporated as a copolymer or as a mixture using a coating composition mixed with another polymer.

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 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 material is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect on the anode, an excellent hole injecting effect on a light emitting layer or a light emitting material because of its ability to transport holes, A compound which prevents the exciton from migrating to the electron injection layer or the electron injection 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 material is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the electron injecting layer to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode to the light emitting layer. Is suitable. 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 injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, A compound which prevents migration to a 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.

In one embodiment of the present invention, the compound may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

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

1. Synthesis of A-1-1-8

(1) Synthesis of intermediate product A-1-1-4

Diborylmethane A-1-1-2 (1.0 g), A-1-1-3 (2.85 g), Pd [P (t-Bu) ₃ ] ₂ and dioxane (37 mL) were added to a dry, . 8 N KOH (aq) (0.7 mL) was added dropwise to the resultant, and the resultant was stirred at room temperature for 24 hours. 8 N KOH (aq) (1.4 mL) was slowly added, the temperature was raised to 60 ° C, and stirring was further continued for 3 days.

The mixture was diluted with DCM (30 mL) and then filtered through silica gel. The filtered solution was distilled under reduced pressure and recrystallized from THF and EtOAc to obtain A-1-1-4.

(2) Synthesis of intermediate product A-1-1-5

A-1-1-4 (400 mg) and DMF (6 mL) were added to the dried round bottom flask. NBS (227 mg) was slowly added to the mixture and the resulting mixture was stirred at room temperature for 24 hours. EtOH (6 mL) and water (6 mL) were added to form a solid, which was then filtered and eluted with EtOH (6 mL × 3). The resulting solid was dissolved in THF (12 mL), c-HCl (0.5 mL) was added slowly, and the mixture was stirred at room temperature for 4 hours. The mixture was diluted with EtOAc (10 mL), washed with 2 N Na ₂ CO ₃ (aq) (4 mL), dried over MgSO ₄ , and filtered through silica gel. The filtered solution was recrystallized from THF and EtOAc solution to obtain A-1-1-5.

FIG. 2 shows the result of M / S test to confirm that A-1-1-5 is synthesized.

(3) Synthesis of intermediate product A-1-8-6

It was added to the B-1-8 (3.8 g), A-1-1-5 (1.9 g), Pd (PPh 3) 4 (155 mg) and THF (27 mL) in a dried round bottom flask. The flask was purged with nitrogen three times. 2 MK ₂ CO ₃ (aq) (2.7 mL) was added to the resultant and stirred at 66 ° C for 4 days. Higo dilute the mixture with DCM (30 mL) was filter to SiO _2. The filtered solution was dried under reduced pressure and purified by column to obtain A-1-1-6. (Column purification with Hex / EtOAc to DCM only solution).

Fig. 3 shows the result of M / S test to confirm that A-1-8-6 is synthesized.

(4) Synthesis of the final product A-1-8

Ph ₃ PCH ₃ Br (1.6 g), and THF (4 mL) were added to an oven-dried round bottom flask. The mixture was cooled to -78 [deg.] C and n-BuLi (1.2 mL, 2.5 M sol'n in hexane) was added. The mixture was heated to 0 ° C and stirred for 30 minutes. To the resultant was added A7 (1.1 g) in THF (4 mL) and the mixture was stirred at room temperature for 4 hours. The mixture was added to water and extracted with DCM. The obtained organic layer was washed with brine solution, dried with MgSO _4, and dried under reduced pressure. The resultant was subjected to column purification (Hex / DCM) to obtain A-1-8 (final).

FIG. 4 is a result of M / S test to confirm that A-1-8 is synthesized.

2. Synthesis of A-2-9

(1) Synthesis of intermediate product A-2-9-3

On the oven dry round bottom flask A-1-1-5 (2.0 g), Boronic acid B2 (3.6 g), Pd (PPh 3) 4 (160 mg), 2 MK 2 CO 3 (2.8 mL) and THF ( 28 mL) was added. The mixture was heated to 66 DEG C and stirred for 24 hours. Higo dilute the mixture with DCM (30 mL) was filter to SiO _2. The filtered solution was dried under reduced pressure and purified by column to obtain A-2-9-3 (2.7 g). (Hex / EtOAc to DCM only).

Fig. 5 is a result of M / S test to confirm that A-2-9-3 is synthesized.

(2) Synthesis of intermediate product A-2-9-4

A-2-9-3 (2.7 g) and THF (19 mL) were added to an oven-dried round bottom flask. The mixture was cooled to 0 < 0 > C and LAH (143 mg) was added. The mixture was stirred at room temperature for 2 hours. H ₂ O (0.15 mL), 15% aq NaOH (0.15 mL) and H ₂ O (0.45 mL) were sequentially added to the resultant, and the mixture was stirred at room temperature for 14 hours. The resultant was subjected to silica filtration, dried under reduced pressure, and then subjected to column purification (Hex / EtOAc = 2: 1) to obtain A-2-9-4 (2.1 g).

6 shows the result of M / S test to confirm that A-2-9-4 is synthesized.

(3) Synthesis of the final product A-2-9

A-2-9-4 (2.1 g) and DMF (8 mL) were added to an oven-dried round bottom flask. The mixture was cooled to 0 < 0 > C and NaH (140 mg) was added. Vinylbenzyl chloride (0.58 mL) was added to the resultant and stirred at room temperature for 12 hours. The mixture was diluted with DCM (30 mL), added to water (40 mL), and extracted with DCM (40 mL x 3). The obtained organic layer was washed with brine solution, dried with MgSO _4, and dried under reduced pressure. The resultant was subjected to column purification (Hex / DCM) to obtain A-2-9 (final) (1.8 g).

FIG. 7 is a M / S test result that confirms that A-2-9 is synthesized.

Using the structures of the following B-1-1 to B-1-7 and B-1-9 to B-1-14 instead of B-1-8 in the above Synthesis Examples A-1-8 and A- Embodiments according to one embodiment of the present disclosure can be produced.

Example 1

The material of the above formula (A-2-9) and the following p-doping material (IB) were mixed at a weight ratio of 9: 1 and chlorobenzene was added dropwise under a nitrogen atmosphere and stirred at room temperature to prepare an ink. The ink thus prepared was spin-coated on the cleaned ITO glass substrate to form a hole injection layer having a thickness of 30 nm. The hole injection layer was cured at 230 DEG C for 1 hour under nitrogen to obtain a uniform thin film. This was introduced into a vacuum deposition apparatus and NPB (20 nm), the following compounds X-1 and X-2 (8% concentration, 30 nm), X-3 (20 nm), LiF ), And deposition was performed at a pressure of ¹ x 10 < ^-7 > Torr or less. The deposition rate of LiF is 0.01 to 0.05 nm / s, and the layer excluding LiF is 0.1 to 0.5 nm / s.

Example 2

Except that A-1-8 was used in place of Compound A-2-9 in Example 1.

Comparative Example 1

Except that the following VNPB was used instead of the compound A-2-9 in Example 1.

The results are shown in Figures 8-10. Referring to FIG. 8, it can be seen that Embodiments 1 and 2 according to one embodiment of the present invention exhibit high external quantum efficiency at the same current density value as that of Comparative Example 1.

Referring to FIG. 9, it can be seen that Examples 1 and 2 according to one embodiment of the present invention at the same voltage have a lower driving voltage when compared with the driving voltage for obtaining the same current density as in Comparative Example 1 Able to know.

Referring to FIG. 10, it can be seen that the luminance reduction widths of Examples 1 and 2 according to one embodiment of the present invention over time are smaller than those of Comparative Example 1.

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

Claims (17)

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

In Formula 1,
L1 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylarylene group and a substituted or unsubstituted arylalkylene group,
L2 and L3 each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group,
Ar 1 to Ar 4 each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, or adjacent substituents may be mutually bonded to form a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group In addition,
Y1 to Y6 each independently represent hydrogen; Or a heat or light polymerization functional group, at least one of which is a heat or light polymerization functional group,
a to f are each independently an integer of 0 or 1,
The sum of a to f is 2 to 6. The method according to claim 1,
Lt; RTI ID = 0.0 > L1 < / RTI >

In the above formula,
X is selected from the group consisting of O, S, SO ₂ , SO, Se and SeO ₂ ,
n is an integer of 1 to 6; The method according to claim 1,
Wherein the heat or light polymerizing functional group is selected from the following structural formula:

In the above formula,
R1 is selected from the group consisting of hydrogen and substituted or unsubstituted alkyl groups. The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the following structural formulas:

. A coating composition comprising a compound according to any one of claims 1 to 4. The method of claim 5,
Wherein the coating composition further comprises a p-doping material. The method of claim 6,
Wherein the p-doping material comprises a compound comprising a sulfonic acid compound or a boron anion as an ionic compound. The method of claim 5,
Wherein the viscosity of the coating composition is between 2 cP and 15 cP. Cathode;
Anode; And
And at least one organic layer provided between the cathode and the anode,
Wherein at least one of the organic material layers is formed using the coating composition of claim 5. The method of claim 9,
Wherein the organic compound layer formed using the coating composition is a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes. The method of claim 9,
Wherein the organic compound layer formed using the coating composition is a light emitting layer. Preparing a substrate;
Forming a cathode or an anode on the substrate;
Forming at least one organic material layer on the cathode or the anode; And
Forming an anode or a cathode on the organic material layer,
Wherein at least one of the organic material layers is formed using the coating composition of claim 5. The method of claim 12,
Wherein the organic compound layer formed using the coating composition is formed using spin coating. The method of claim 12,
Wherein the organic compound layer formed using the coating composition is formed by a printing method. 16. The method of claim 15,
Wherein the organic compound layer formed using the coating composition is formed by an ink jet method. The method of claim 12,
The step of forming one or more organic layers
Coating the coating composition on the cathode or anode; And
And heat treating or light-treating the coated coating composition. 18. The method of claim 16,
Wherein the heat treatment temperature of the step of heat treating the coated coating composition is 250 DEG C or less.

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