KR20190010057A - Fluorene derivatives, coating composition comprising fluorene derivatives, organic light emitting diode using the same and method of manufacturing the same - Google Patents

Abstract

The present invention relates to a fluorene derivative which can allow a device to have a large area since a solution process can be performed, a coating composition including the same, an organic light emitting device using the same, and a manufacturing method thereof. The fluorene derivative is represented by chemical formula 1. In chemical formula 1, Ar1 to Ar4 are the same or different, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and R1 to R8 are the same or different, and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a coating composition comprising a fluorene derivative, a fluorene derivative, and a fluorene derivative, an organic light emitting device using the same, and a method for manufacturing the same. BACKGROUND ART [0002] Fluorescent light emitting diodes (OLEDs)

The present invention relates to a fluorene derivative, a coating composition comprising the fluorene derivative, 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 introduced 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 transporting layer material, has a glass transition temperature of 100 ° C or less, which makes it 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.

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

Korean Patent Laid-Open Publication No. 2012-0112277

It is an object of the present invention to provide a fluorene derivative usable in an organic light emitting device, a coating composition containing the fluorene derivative, an organic light emitting device including the same, and a method of manufacturing the same.

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

[Chemical Formula 1]

In Formula 1,

Ar 1 to Ar 4 are the same or different and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

R 1 to R 8 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, Gt; is a substituted heteroaryl group,

L is O or - (X1) x-Y1- (Z-Y2) y- (X2)

And X1, X2 and Z are the same as or different from each other, each independently, O, S, CO, SO _2, SO, Se, SeO _2, or SiR'R ",

Y1 and Y2 are the same or different and each independently represents O, a substituted or unsubstituted arylene group, or a substituted or unsubstituted alkylene group,

R 'and R " are the same or different and each independently hydrogen or a substituted or unsubstituted alkyl group,

a and b are integers of 0 to 7,

x, y and z are integers of 0 or 1.

The present disclosure also provides a coating composition comprising the fluorene derivative.

The disclosure also includes a cathode; Anode; And one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers is formed using the coating composition.

Finally, the present disclosure provides a method of manufacturing a semiconductor device, 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 the forming the organic material layer includes forming one or more organic material layers using the coating composition. do.

Fluorene derivatives according to one embodiment of the present invention can be subjected to a solution process, thereby enabling the device to have a large area. The fluorene derivative according to one embodiment of the present invention can be used as an organic material 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 material layer formed using the fluorene derivative according to one embodiment of the present specification is excellent in chemical resistance.

Further, the use of the fluorene derivative increases the solubility, so that the selection of the solvent in the ink manufacturing process of the solution process is widened and the molecular weight is increased to have an appropriate coating property.

1 shows an example of an organic light emitting device according to an embodiment of the present invention.
Fig. 2 is a graph showing mass analysis results of A1. Fig.
3 is a graph showing the results of mass spectrometry of A2.
4 is a graph showing the results of mass spectrometry of A3.
5 is a voltage comparison graph of Example 1, Example 2, and Comparative Example 2. Fig.
6 is an efficiency comparison graph of Example 1, Example 2, and Comparative Example 2. Fig.
7 is a life comparative graph of Example 1, Example 2, and Comparative Example 2. Fig.

Hereinafter, the present specification will be described in detail.

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

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

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

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

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

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

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

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; An alkyl group; An alkoxy group; An alkenyl group; An aryl group; And a heteroaryl group, or a substituted or unsubstituted one in which at least two of the above exemplified substituents are connected to each other. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the halogen group is fluorine, 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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. 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, but are not limited thereto.

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, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.

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.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 40 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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.

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 40 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 20 carbon atoms. The heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, Phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but the present invention is not limited thereto.

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

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 cycloalkylene group may be selected from the examples of the above-mentioned cycloalkyl group, except that it is a divalent group.

In the present specification, the heteroarylene group may be selected from the examples of the above-mentioned heteroaryl group, except that it is a divalent group.

According to one embodiment of the present invention, the fluorene derivative of the present invention can be represented by the following general formula (1).

[Chemical Formula 1]

According to one embodiment of the present invention, the compound of Formula 1 may include two or more triazine groups.

According to one embodiment of the present invention, the compound of Formula 1 has increased solubility by including a triazine group substituted with an alkyl group

When two or more triazines are included, Molecular weight 1000-2000 g / mol And the triazine structure having electronic properties occupies 50% or more of the total molecular weight, so that it has suitable solubility and coating property as a solution OLED material.

According to one embodiment of the present invention, the fluorene derivative of the present invention can be represented by the following formula (2).

(2)

In the above formula (2), Ar1 to Ar4, R1 to R8, L, and a to d are as defined in the above formula (1).

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and are each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and are each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and are each independently a direct bond; A phenylene group substituted or unsubstituted with a methyl group; Or a naphthylenylene group substituted or unsubstituted with a methyl group.

According to one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenylene group; Or a naphthylenylene group.

According to one embodiment of the present disclosure, Ar3 and Ar4 are the same or different from each other and are each independently a phenyl group.

According to one embodiment of the present disclosure, R 1 to R 8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R1 to R4 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted C6 to C20 aryl group.

According to one embodiment of the present disclosure, R1 to R4 are the same or different from each other, and each independently hydrogen; Or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group or a silyl group.

According to one embodiment of the present disclosure, R1 to R4 are the same or different from each other, and each independently hydrogen; An aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a silyl group substituted or unsubstituted with an alkyl group or an aryl group.

According to one embodiment of the present disclosure, R1 to R4 are the same or different from each other, and each independently hydrogen; A phenyl group substituted or unsubstituted with a methyl group, a t-butyl group, or a trimethylsilyl group; A biphenyl group substituted or unsubstituted with a methyl group, a t-butyl group, or a trimethylsilyl group; A terphenyl group substituted or unsubstituted with a methyl group, a tert-butyl group, or a trimethylsilyl group; A naphthyl group substituted or unsubstituted with a methyl group, a t-butyl group, or a trimethylsilyl group; Or a fluorene group substituted or unsubstituted with a methyl group, a t-butyl group, or a trimethylsilyl group.

According to one embodiment of the present invention, R 1 to R 4 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted with a methyl group, a terbutyl group, or a trimethylsilyl group; Biphenyl group; Naphthyl group; A terphenyl group substituted or unsubstituted with a tert-butyl group; Or a fluorene group substituted or unsubstituted with a methyl group.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; Or an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a substituted or unsubstituted silyl group.

According to one embodiment of the present invention, R5 and R6 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted with a methyl group, a terbutyl group, a trimethylsilyl group, or a triphenylsilyl group; Or a fluorene group substituted or unsubstituted with a methyl group.

According to one embodiment of the present specification, R7 and R8 are the same or different from each other, and each independently is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted silyl group.

According to one embodiment of the present disclosure, R7 and R8 are the same or different from each other, and each independently hydrogen, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present disclosure, R7 and R8 are the same or different from each other, and each independently hydrogen or a methyl group.

When R1 to R4, R7 or R8 is an alkyl group or a silyl group, the solubility is improved.

According to one embodiment of the present disclosure, L is O, or - (X1) x-Y1- (Z-Y2) y- (X2) z-.

According to one embodiment of the present disclosure, L is O, -X1-Y1-X2-, -X1-Y1-Z-Y2-X2-, or -Y1-.

According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, each independently represent O, S, CO, SO _2, SO, Se, SeO _2, or SiR'R ".

According to one embodiment of the present disclosure, X1 and X2 are the same or different and each independently O, or SiR'R ".

According to one embodiment of the present disclosure, Y1 and Y2 are the same or different from each other and are each independently 0; A substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, Y1 and Y2 are the same or different from each other and are each independently 0; A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, Y1 and Y2 are the same or different from each other and are each independently 0; A substituted or unsubstituted methylene group; A substituted or unsubstituted hexylene group; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted fluorenylene group.

According to one embodiment of the present disclosure, Y1 and Y2 are the same or different from each other and are each independently 0; A substituted or unsubstituted methylene group; A substituted or unsubstituted hexylene group; A phenylene group substituted or unsubstituted with an alkyl group; A fluorenylene group spiro bonded to a cycloalkyl group; Or a fluorenylene group substituted or unsubstituted with an alkyl group.

According to one embodiment of the present disclosure, Y1 and Y2 are the same or different from each other and are each independently 0; A methylene group; A hexylene group; A phenylene group; A fluorenylene group spiro bonded to a cycloalkyl group having 5 to 10 carbon atoms; Or a fluorenylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present disclosure, Z is a carbonyl group, or a sulfonyl group.

According to one embodiment of the present disclosure, R 'and R " are the same or different and each independently represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R 'and R "are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms .

According to one embodiment of the present disclosure, R 'and R " are the same or different from each other, and are each independently a methyl group or a phenyl group.

According to one embodiment of the present disclosure, a and b are integers from 0 to 7.

According to one embodiment of the present disclosure, x, y and z are 0 or 1.

According to one embodiment of the present invention, the compound of Formula 1 may be represented by any one of the following compounds.

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

For example, the compound of Formula 1 can be prepared as a core structure as shown in Reaction Scheme 1 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

<General Production Method of Chemical Formula 1>

R 1 ', R 2', R 5 'Ar 1', Ar 3 'and Y 1' have the same definitions as R 1, R 2, R 5, Ar 1, Ar 3 and Y 1 in the formula (1).

The starting material and the reactant can be replaced by commercially available ones, whereby an asymmetric structure can be produced. In addition, the combination of the moieties corresponding to L in the above formula (1) may be different.

In one embodiment of the present disclosure, there is provided a coating composition comprising a fluorene derivative as described above.

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

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

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 fluorene derivative is 1,000 g / mol to 3,000 g / mol.

In one embodiment of the present invention, the fluorene derivative may further include a thermosetting group or a photocurable 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, chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; Examples of polyhydric alcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, Alcohols and their derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethylsulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; A solvent such as tetralin is exemplified, but a solvent capable of dissolving or dispersing the fluorene derivative 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 invention, the coating composition may further include one or more additives selected from the group consisting of a thermal polymerization initiator and a photopolymerization initiator.

Examples of the thermal polymerization initiator include methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methyl cyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide , Bis-3,5,5-trimethylhexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-chlorobenzoyl peroxide, dicumyl peroxide, 2,5-dimethyl- Oxy-hexane, 1,3-bis (t-butylperoxy-isopropyl) benzene, t-butyl cumyl peroxide, di- T-butylperoxy) hexane-3, tris- (t-butylperoxy) triazine, 1,1-ditertiary butyl peroxy-3,3,5-trimethylcyclohexane, 1,1- Butylperoxycyclohexane, 2,2-di (t-butylperoxy) butane, 4,4-di-t-butoxypivalicylic acid n-butyl ester, 2,2- 4-t-butylperoxy Butyl peroxy isobutyrate, t-butyl peroxyhexahydroterephthalate, t-butyl peroxy-3,5,5-trimethyl hexaate, t-butyl peroxybenzoate, di and peroxides such as t-butyl peroxytrimethyl adipate, and azo compounds such as azobisisobutylnitrile, azobisdimethylvaleronitrile, and azobiscyclohexyl nitrile, but are not limited thereto.

Examples of the photopolymerization initiator include diethoxyacetophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, 1 -hydroxy-cyclohexylphenyl-ketone, 4- (2-hydroxyethoxy) Phenyl-2- (2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) 1-one, 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) oxime , Etc., benzoin ethers such as benzoin, benzoin methylurate, benzoin etchurateur, benzoin isobutyrate, benzoin isopropyrate, etc., Based photopolymerization initiator such as benzophenone, 4-hydroxybenzophenone, 2-benzoylnaphthalene, 4-benzoylbiphenyl, 4-benzoylphenyl ether, acrylated benzophenone and 1,4-benzoylbenzene, 2-isopropylthioxanthone, 2- Examples of the photopolymerization initiator include thioxanthone photopolymerization initiators such as thioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone and 2,4-dichlorothioxanthone, and other photopolymerization initiators include ethyl anthraquinone, 2 , 2,4,6-trimethylbenzoylphenyl ethoxyphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, bis (2,4- Dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, methylphenyl glyoxycellester, 9,10-phenanthrene, acridine compound, triazine compound, imidazole compound have. The photopolymerization initiator having the photopolymerization promoting effect may be used alone or in combination with the photopolymerization initiator. Examples thereof include triethanolamine, methyldiethanolamine, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, benzoic acid (2-dimethylamino) ethyl and 4,4'-dimethylaminobenzophenone, It is not limited thereto.

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 a cathode And at least one layer of the organic material layer is formed using the coating composition or a cured product thereof.

In one embodiment of the present invention, the organic light emitting device includes the fluorene derivative of Formula 1 in the light emitting layer.

In one embodiment of the present invention, the organic light emitting device includes a fluorene derivative of Formula 1 as a host in the light emitting layer.

In one embodiment of the present invention, the organic light emitting device further includes a light emitting material such as a fluorene derivative and a metal complex of Formula 1 in the light emitting layer.

The metal complex may be an iridium complex, but is not limited thereto. (A '+ b' + c '= 3, a', b 'and c' are integers of 0-3) of Ir (L1) a ' Structure. L1 is an anionic monoanionic bidentate cyclometalating ligand, linked by a carbon and nitrogen atom, L2 is a monoanionic bidentate ligand and is not linked by carbon, and L3 is a monoanionic bidentate ligand The ligand (monodentate ligand).

Ll is preferably selected from the group consisting of phenylpyridines, phenylquinolines, phenylpyrimidines, phenylpyrazoles, thienylpyridins, thienylquinolines, thienylpyridines, Thienyl pyrimidines, and the like, but are not limited thereto.

L2 is an atom in which N, O, P, and S are mainly coordinated, and forms iridium and pentagonal or hexagonal rings. Suitable coordinating groups include amino groups, imino groups, amido groups, alkoxy groups. A carboxylate group, a phosphine group, and a thiolate group. However, the present invention is not limited thereto.

L3 is anionic or nonionic and the anionic ligand has C, O, S as a coordinating atom, and specifically includes carboxylate, thiocarboxylate thiocarboxylate, thiocarboxylate, dithiocarboxylate, sulfonate, thiolate, carbamate, dithiocarbamate, thiocarbazone anions, sulfonamide sulfonamides, anions, and the like, but are not limited thereto.

The iridium complex may be represented by the following formula.

In one embodiment of the present invention, the organic light emitting device includes a luminescent material such as a metal complex in the light emitting layer, the fluorene derivative in a weight ratio of 1: 100 or 100: 1.

In one embodiment of the present invention, the organic light emitting device includes a luminescent material such as a metal complex in the light emitting layer, the fluorene derivative in a weight ratio of 1: 100 to 20: 1.

In another embodiment, the organic light-emitting device includes a luminescent material such as a metal complex in the light-emitting layer: the fluorene derivative in a weight ratio of 1: 100 or 1: 1.

In one embodiment of the present invention, the organic light emitting device includes a luminescent material such as a metal complex in the light emitting layer, the fluorene derivative in a weight ratio of 5:95 to 20:80.

In one embodiment of the present invention, the organic light emitting device comprises a coating composition comprising the fluorene derivative of Formula 1, or a cured product thereof, in a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes .

In one embodiment of the present invention, the organic light emitting device may include a coating composition containing a fluorene derivative of Formula 1 in a hole transport layer, a hole injection layer, or a layer that simultaneously transports holes and holes.

In one embodiment of the present invention, the organic light emitting device may include a cured product of the coating composition comprising the fluorene derivative of Formula 1 in a hole transport layer, a hole injection layer, or a layer that simultaneously transports holes and holes .

In one embodiment of the present invention, the organic light emitting device comprises a coating composition comprising the fluorene derivative of Formula 1, or a cured product thereof, in an electron injecting layer, an electron transporting layer, or a layer simultaneously performing electron injection and electron transport can do.

In one embodiment of the present invention, the organic light emitting device may include a coating composition comprising the fluorene derivative of Formula 1, or a cured product thereof, in the electron blocking layer.

In one embodiment of the present invention, the organic light emitting device may include a coating composition comprising the fluorene derivative of Formula 1, or a cured product thereof, in the major blocking layer.

In one embodiment of the present invention, the organic light emitting element includes a light emitting layer, a hole injecting layer, and a hole transporting 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 illustrates a structure of an organic light emitting device in which an anode 201, a hole injecting and transporting layer 301, a light emitting layer 401, an electron transporting layer 501, and a cathode 601 are sequentially stacked on a substrate 101 have.

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 the coating composition comprising the fluorene derivative or a cured product thereof.

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 invention also provides a method of manufacturing an organic light emitting device formed using the coating composition or a cured product thereof.

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.

The step of forming at least one layer of the organic material layer using the coating composition may include a coating step followed by a drying step. If necessary, the drying step may include a curing step.

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.

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 the organic layer using the coating composition includes heat treatment or vacuum drying. The residual solvent is removed through the heat treatment or the vacuum drying step.

In one embodiment of the present invention, the step of forming the organic layer using the coating composition includes vacuum drying.

In one embodiment of the present disclosure, the step of heat-treating or vacuum-drying may comprise a curing step.

In one embodiment of the present invention, the coating composition containing the fluorene derivative may be a coating composition prepared by mixing and dispersing the fluorene derivative in 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 .

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); A combination of a metal and an oxide such as ZnO: Al or SNO2: 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 LiO2 / 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 (Alq3); 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 fluorene 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 Alq3; 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 fluorene derivative 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.

According to another embodiment, the compound of formula 1 may be represented by the following structural formulas.

< Synthetic example >

One. A1's  synthesis

10 g A1-2, A1-3 10.2 g was added to a 500 mL round bottom flask (RBF) was added (PPh _{3) 4} Pd 1.2 g. The mixture was evacuated and refilled with nitrogen. This procedure was repeated three times and 210 mL of tetrahydrofuran (THF) was added. After dissolving all the solid by stirring, 21 mL of 2 MK ₂ CO ₃ (aq) was added. Followed by stirring at 60 占 폚 for 12 hours.

The resulting mixture was added 200 mL NH ₄ Cl (aq), extracted with EtOAc 200 mL (x2). The organic layer was dried over MgSO ₄ , filtered and concentrated. The resulting mixture was dissolved in DCM, poured into EtOH, and solidified. The obtained solid was recrystallized from DCM / EtOH to obtain 10 g of A1-1.

A1-1 3.39 g was dissolved in 50 mL of Acetone, and then 1.3 g of potassium carbonate was added. After stirring for 5 minutes, 0.37 mL of dibromohexane was added. The mixture was refluxed for 3 days and stirred. To the obtained mixture, 50 mL of NH ₄ Cl (aq) and DCM (200 mL) were added. After the organic layer was obtained, SiO ₂ (50 g) was added and stirred for 30 minutes. The resulting solution was concentrated, dissolved in DCM, and recrystallized with EtOH to obtain 2 g of Al.

Fig. 2 is a graph showing mass analysis results of A1. Fig.

2. A2  synthesis

A1-1 was dissolved in 10 mL of NMP, and 1 g of potassium carbonate was added thereto. The mixture was then heated to 150 &lt; 0 &gt; C and stirred for 2 days. EtOH was added to the resulting mixture, and the resulting solid was filtered. The solid was dissolved in DCM, and the SiO ₂ column was purified. The solid was recrystallized from DCM / Hexane mixed solution to obtain 1 g of A2.

3 is a graph showing the results of mass spectrometry of A2.

3. A3  synthesis

1 g of A3-1 was dissolved in 6 mL of NMP, and 0.4 g of potassium carbonate was added thereto. After adding 130 mg of A3-1, the mixture was heated at 150 DEG C and stirred for 2 days. EtOH was added to the resulting mixture, and the resulting solid was filtered. The solid was dissolved in DCM, and the SiO ₂ column was purified. The solid was recrystallized using DCM / Hexane mixed solution to obtain 0.5 g of A3.

4 is a graph showing the results of mass spectrometry of A3.

Experimental Example 1. Measurement of solubility of the synthesized material

1900 mg of toluene was added to 100 mg of the compound of the above Synthesis Example A1, and the mixture was heated to 60 占 폚 using an oil bath. After dissolving all of the solids, they were cooled to room temperature and observed to precipitate one hour later. One week later, they were observed again. The prepared solution maintained a clear solution without precipitation after one week.

Experimental Example  2.

Except that Compound A2 was used instead of Compound A1 in Experimental Example 1 above. The prepared solution maintained a clear solution without precipitation after one week.

Through experiments 1 and 2, it was confirmed that the compound of formula (1) had a suitable solubility as a material for solution process.

< Example >

Example  One

A glass substrate coated with a thin ITO (indium tin oxide) film with a thickness of 50 nm was washed with ultrasonic waves in distilled water containing detergent. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

AI4083 was formed on the ITO transparent electrode prepared as described above under the process conditions shown in Table 1 below to form a 60 nm hole injection layer and a transport layer.

matter Coating speed time Soft baking Hard baking AI4083 1000 rpm 60s 80 ° C, 2 min 120 DEG C, 15 min

The poly (9,9-di-n-octylfluorenyl-2,7-diyl) (Sigma Aldrich) ), A 0.5 wt% toluene solution of the compound A1 and the metal complex D41 of the above Synthesis Example in a weight ratio of 91: 9 was spin coated at 5000 rpm, baked at 80 DEG C for 2 minutes, baked at 120 DEG C for 30 minutes ) To form a light emitting layer having a thickness of 55 nm.

This was dried in a nitrogen gas atmosphere at 130 占 폚 for 10 minutes, and lithium fluoride (LiF) was vapor-deposited to a thickness of about 1 nm. Finally, aluminum was vapor-deposited to a thickness of 100 nm to form a cathode.

During the above process, the deposition rate of lithium fluoride was maintained at 0.3 Å / sec for aluminum and 2 Å / sec for aluminum, and the vacuum level during deposition was maintained at 2 × 10 ^-7 to 5 × 10 ^-6 torr to fabricate an organic light emitting device .

Example  2

The experiment was carried out in the same manner as in Example 3 except that the compound A2 was used in place of the compound A1 in Example 1.

< Comparative Example >

Comparative Example  One.

Comparative Example B1 was used instead of A1 in Experimental Example 1 Experiments were carried out, however, it was not dissolved and toluene could be dissolved by addition of 2000 mg. However, it was observed at room temperature for one week and deposited.

From the above results, it can be seen that the compound of the present invention has good solubility of 5 wt / wt% or more and is not precipitated even when stored for a long time, and thus is suitable as a material for solution processing.

Comparative Example  2

In the same manner as in Example 1, except that Comparative Compound B1 was used instead of A1.

The results of Examples 1 and 2 and Comparative Example 2 are shown in Figs.

5 is a voltage comparison graph of Example 1, Example 2, and Comparative Example 2. Fig. As a result, it can be seen that Example 1 and Example 2 are driven at a lower voltage than Comparative Example 2.

6 is an efficiency comparison graph of Example 1, Example 2, and Comparative Example 2. Fig. As a result, it was confirmed that Example 1 and Example 2 emit light at a higher efficiency than Comparative Example 2.

7 is a life comparison graph of Example 1, Example 2, and Comparative Example 2; As a result, it can be seen that the life span of Example 1 and Example 2 is longer than that of Comparative Example 2.

101: substrate
201: anode
301: hole injection and transport layer
401: light emitting layer
501: electron transport layer
601: cathode

Claims (15)

A fluorene derivative represented by the following formula (1): &lt; EMI ID =
[Chemical Formula 1]

In Formula 1,
Ar 1 to Ar 4 are the same or different and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
R 1 to R 8 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, Gt; is a substituted heteroaryl group,
L is O or - (X1) x-Y1- (Z-Y2) y- (X2)
And X1, X2 and Z are the same as or different from each other, each independently, O, S, CO, SO _2, SO, Se, SeO _2, or SiR'R ",
Y1 and Y2 are the same or different and each independently represents O, a substituted or unsubstituted arylene group, or a substituted or unsubstituted alkylene group,
R 'and R &quot; are the same or different and each independently hydrogen, or a substituted or unsubstituted alkyl group,
a and b are integers of 0 to 7,
x, y and z are 0 or 1;
[2] The method of claim 1, wherein the fluorene derivative represented by Formula 1 is represented by Formula 2:
(2)

In the formula (2)
R1 to R8, Ar1 to Ar4, L, a and b are as defined in the above formula (1).
[3] The compound according to claim 1, wherein Ar &lt; 1 &gt; and Ar &lt; 2 &gt; are the same or different and are each independently a substituted or unsubstituted phenylene group; Or a naphthylenylene group.
2. The fluorene derivative according to claim 1, wherein Ar3 and Ar4 are the same or different and are each independently a phenylene group.
The compound according to claim 1, wherein R 1 to R 4 are the same or different and each is a phenyl group substituted or unsubstituted with a methyl group, a t-butyl group, or a trimethylsilyl group; Biphenyl group; Naphthyl group; A terphenyl group substituted or unsubstituted with a tert-butyl group; Or a fluorene group substituted or unsubstituted with a methyl group.
[4] The compound according to claim 1, wherein R5 and R6 are the same or different and each is a phenyl group substituted or unsubstituted with a methyl group, a terbutyl group, a trimethylsilyl group, or a triphenylsilyl group; Or a fluorene group substituted or unsubstituted with a methyl group.
The fluorene derivative according to claim 1, wherein the fluorene derivative is any one of the following compounds:

The fluorene derivative according to claim 1, wherein the fluorene derivative has a molecular weight of 1,000 g / mol to 3,000 g / mol. A coating composition comprising a fluorene derivative according to any one of claims 1 to 8. 10. The coating composition of claim 9, wherein the coating composition further comprises a luminescent material such as a metal complex. The coating composition according to claim 9, wherein the coating composition is a mixture of a luminescent material such as a metal complex: the fluorene derivative in a weight ratio of 1: 100 or 1: 1. 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 comprises the coating composition of claim 9 or a cured product thereof. [Claim 12] The organic light emitting device according to claim 12, wherein the organic material layer is a hole transporting layer, a hole injecting layer, or a layer simultaneously injecting holes and transporting a hole containing the cured product of the coating composition. 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 the forming of the organic material layer includes forming at least one organic material layer using the coating composition of claim 9. [16] The method of claim 14, wherein the step of forming the organic material layer using the coating composition comprises a drying step after the application of the coating composition.

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