KR20180008154A - Carbazole derivatives, organic light emitting diode using the same and method of manufacturing the same - Google Patents

Abstract

The present invention relates to a carbazole derivative, a coating composition containing the carbazole derivative, an organic light-emitting device using the same, and a production method thereof. According to an embodiment of the present invention, the carbazole derivative is represented by chemical formula 1, and can be used as a material for organic layers in organic light-emitting devices.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a carbazole derivative, an organic light-emitting device using the same, and a method for manufacturing the same. BACKGROUND ART [0002]

The present invention relates to a carbazole derivative, a coating composition comprising the carbazole 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 carbazole derivative usable in an organic light emitting device and an organic light emitting device including the same.

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

[Chemical Formula 1]

In Formula 1,

L ₁ to L ₅ are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

D ₁ is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylamine group,

Ra and Rb are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,

r1 and r2 are each an integer of 0 to 7,

When r1 and r2 are 2 or more, the substituents in parentheses are the same or different from each other,

X ₁ and X ₂ are the same or different from each other, and each independently is a thermosetting group or a photocurable group.

The present disclosure provides coating compositions comprising the carbazole derivatives.

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.

The carbazole derivative according to one embodiment of the present invention can be subjected to a solution process, and the device can be made large in area. The carbazole derivative 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 material layer formed using the carbazole derivative according to one embodiment of the present invention is excellent in chemical resistance and film retention.

1 shows an example of an organic light emitting device according to an embodiment of the present invention.
FIG. 2 is a view showing a film retention rate of a thin film prepared from the coating composition C1-1-2 by UV-Visible spectroscopy.
FIG. 3 is a view showing the film retention of the thin film prepared in Comparative Example 1 by UV-Visible spectroscopy.
4 shows an NMR spectrum of Intermediate 1. 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.

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

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

As used herein, the term " thermosetting group or photocurable group " may mean a reactive substituent that causes crosslinking between the compounds by exposure to heat and / or light. The crosslinking can be produced by heat treatment or light irradiation, and connecting the radicals generated by decomposition of the carbon-carbon multiple bond, cyclic structure.

In one embodiment of the present disclosure, the thermosetting group or photocurable group is any one of the following structures.

In the above structure,

A 1 to A 3 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

In one embodiment of the present invention, a carbazole derivative having a thermosetting group or a photocurable group 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 carbazole derivative containing a thermosetting group or a photocurable group, since a crosslinking is formed by heat or light by a thermosetting group or a photocurable group, It is possible to prevent the carbazole derivative contained in the coating composition from being washed out by the solvent when the layers are laminated so that the additional layer can be laminated on top of the coating layer.

In addition, when a coating layer is formed by forming a crosslinking by a thermosetting group or a photocurable group, the coating layer has an increased chemical resistance to a solvent and a high film retention ratio.

In addition, in the case of the carbazole 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 size can be increased.

According to one embodiment of the present invention, in the case of a carbazole derivative crosslinked by heat treatment or light irradiation, since a plurality of carbazole derivatives are crosslinked to be provided in a thin film form in the organic light emitting device, there is an effect of excellent thermal stability. Therefore, the organic light emitting device using the carbazole derivative according to one embodiment of the present invention has an excellent lifetime characteristic.

In addition, since the carbazole derivative 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 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 " 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, the halogen group is fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear, branched or cyclic,

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, 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, 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.

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 silyl group is specifically exemplified by trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, However, the present invention is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.

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, but is preferably 10 to 30 carbon atoms. Specific 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 crycenyl group, a carbazolyl 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 50 carbon atoms, and 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, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofuranyl groups.

,

,

,

등이 있으나, 이들에만 한정되는 것은 아니다.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 phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, a diphenylamine group, a phenylpyridylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, Dibenzofuranylphenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group,

,

,

,

And the like, but are not limited thereto.

In the present specification, the aryl group of the arylalkyl group and the arylamine group may be exemplified by the aryl group described above.

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

As used herein, the term " adjacent " means a substituent in which the substituent is substituted with an atom directly connected to the substituted atom, or a substituent that is stereostatically closest to the substituent, or a substituent in which the substituent is substituted with a substituted atom can do. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other. Alternatively, two substituents of carbon number 9 in the fluorene 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.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. 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 heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed rings, and may be selected from the examples of the heteroaryl group except that it is not monovalent.

In one embodiment of the present specification, D ₁ is hydrogen; A substituted or unsubstituted aryl group or a substituted or unsubstituted arylamine group.

In one embodiment of the present specification, D ₁ is hydrogen; A substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted aryl group with a substituted or unsubstituted heterocyclic group; Or an arylamine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group .

In one embodiment of the present invention, D ₁ is a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, an aryl group substituted or unsubstituted with a substituted or unsubstituted arylamine group, Or an arylamine group substituted or unsubstituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted arylamine group.

In one embodiment of the present specification, D ₁ is hydrogen; An aryl group which is substituted or unsubstituted with a substituted or unsubstituted aryl group or a substituted or unsubstituted arylamine group; Or an arylamine group substituted or unsubstituted with a substituted or unsubstituted aryl group or a substituted or unsubstituted arylamine group.

In one embodiment of the present invention, L ₁ and L ₂ are the same or different from each other and are each independently a direct bond; Or an arylene group.

In one embodiment of the present invention, L ₁ and L ₂ are the same or different from each other and are each independently a direct bond; Or a phenylene group.

In another embodiment, L < _{1 >} and L < ₂ > are direct bonds.

In another embodiment, L ₁ and L ₂ are phenylene groups.

In one embodiment of the present invention, L ₃ and L ₄ are the same or different from each other and are each independently a direct bond; Or an arylene group.

In another embodiment, L ₃ and L ₄ are the same or different and are each independently a phenylene group or a biphenylene group.

In another embodiment, L ₃ and L ₄ are a phenylene group or a biphenylene group.

In one embodiment of the present specification, L ₅ is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L ₅ is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In one embodiment of the present invention, L ₅ is a phenylene group or a biphenylene group.

In one embodiment of the present specification, Ra and Rb are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another embodiment, Ra and Rb are the same or different from each other and represent hydrogen; Or an aryl group.

In another embodiment, Ra and Rb are phenyl groups, and r1 and r2 are 1.

In another embodiment, Ra and Rb are hydrogen.

In one embodiment of the present invention, the formula (1) is a carbazole derivative represented by the following formula (2) or (3).

(2)

(3)

In the general formula (2) or (3)

L ₃ to L- ₅ , Ra, Rb, r ₁ , r ₂ , X ₁ , X ₂ and D ₁ are as defined in the formula (1)

R11 and R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

m1 and m2 are each an integer of 0 to 4,

When m1 and m2 are each 2, the substituents in the parentheses are the same or different from each other.

In one embodiment of the present specification, R11 and R12 are the same or different from each other and each independently hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

In another embodiment, R11 and R12 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted amine group.

In one embodiment of the present invention, the formula (1) is a carbazole derivative represented by any one of the following formulas (4) to (7).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 4 to 7,

L ₅ , Ra, Rb, r ₁ , r 2, D ₁ , X ₁ and X ₂ are the same as defined in formula (1)

R13 to R16 and R101 and R112 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

m3 to m6 and p1 to p12 each are an integer of 0 to 4,

When m3 to m6 and p1 to p12 are each 2 or more, the substituents in the parentheses are the same or different from each other.

In one embodiment of the present specification, R13 to R16 and R101 to R112 are the same or different and each independently hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

In another embodiment, R13 to R16 and R101 to R12 may be the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted amine group.

In one embodiment of the present invention, the formula (1) is a carbazole derivative represented by any one of the following formulas (8) to (11).

 [Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the general formulas (8) to (11)

L ₅ , D _1, X ₁ , X ₂ , R a, R b, r 1 and r 2 are the same as defined in formula (1)

R21 to R32 and R113 to R124 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,

n1 to n4 and n9 to n12 each is an integer of 0 to 5,

n5 to n8 and p13 to p24 each is an integer of 0 to 4,

When n1 to n8 and p13 to p24 are each 2 or more, the substituents in the parentheses are the same or different from each other.

In one embodiment of the present specification, R21 to R32 and R113 to R124 are the same or different and each independently hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

In another embodiment, R21 to R32 and R113 to R124 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted amine group.

In one embodiment of the present invention, D ₁ in the formula ( ₁₎ is a carbazole derivative represented by the following structural formula.

In the above structural formulas,

R ₁ to R ₃ are the same or different and each independently hydrogen; An amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,

q1 to q3 each represent an integer of 0 to 5,

When q1 to q3 are 2 or more, the structures in parentheses are equal to or different from each other.

In one embodiment of the present disclosure, R < ₁ > is hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R ₁ is selected from the group consisting of hydrogen; Or an alkyl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In another embodiment, R ₁ is selected from the group consisting of hydrogen; Or an alkyl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted aryl group.

According to another embodiment, R < _{1 >} is hydrogen or an isopropyl group, or is bonded to adjacent substituents to form a 9,9-dimethylfluorene group.

In one embodiment of the present disclosure, R ₂ and R ₃ are the same or different and each independently hydrogen; An amine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R ₂ and R ₃ are the same or different and each independently hydrogen; An aryl group substituted or unsubstituted with an alkyl group or an amine group, or adjacent substituents include a hydrocarbon ring substituted by bonding to each other; Or a substituted or unsubstituted heterocyclic group.

,

,

, 카바졸릴기, 디페닐아민기, 피리딜기 또는 페닐기로 치환된 디페닐아민기, 9,9-디메틸플루오레닐페닐아민기, 디벤조퓨라닐페닐아민기, 페닐기로 치환된 티오펜기 또는 1-옥틸노닐기로 치환 또는 비치환된 페닐기이거나, 인접하는 치환기와 서로 결합하여 9,9-디메틸플루오레닐기, 디벤조티오페닐기, 디벤조퓨라닐기, 에틸기 또는 페닐기로 치환된 카바졸릴기, 9,9-디옥틸플루오레닐기를 형성한다.In one embodiment of the present disclosure, R ₂ and R ₃ are the same or different and each independently hydrogen; An isopropyl group, a diphenylamine group, a pyridylphenylamine group,

,

,

, A diphenylamine group substituted with a carbazolyl group, a diphenylamine group, a pyridyl group or a phenyl group, a 9,9-dimethylfluorenylphenylamine group, a dibenzofuranylphenylamine group, a thiophene group substituted with a phenyl group, or A phenyl group substituted or unsubstituted with an 1-octylnonyl group, a carbazolyl group substituted with an adjacent substituent and substituted with a 9,9-dimethylfluorenyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an ethyl group or a phenyl group, 9 , 9-dioctylfluorenyl group is formed.

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

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

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

[Reaction Scheme 1]

As shown in Reaction Scheme 1, a carbazole protected with acetal was reacted with at least three equivalents of a primary aromatic arylamine under catalyst and inorganic base conditions. Thereafter, it is transformed into a deprotection formyl group by heating and stirring at room temperature or 80 DEG C under aqueous acidic conditions. A double bond was formed by Wittig reaction with Ph ₃ PCH ₂ Br under n-BuLi or K (t-BuO) conditions.

[Reaction Scheme 2]

                                       Intermediate 1

In Scheme 1, 1.2 equivalents of primary arylamine are used to provide intermediate 1. The NMR spectrum of Intermediate 1 thus obtained is shown in Fig. Thereafter, proceeding in the same manner as in Scheme 1, a compound of the general formula 1 is obtained.

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

In one embodiment of the present disclosure, the coating composition comprises the carbazole derivative 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 thermosetting group or a photocurable group introduced into the molecule and a polymer compound.

In one embodiment of the present invention, the coating composition may further comprise a compound having a thermosetting group or a photocurable group introduced into the molecule. When the coating composition further contains a compound having a thermosetting group or a photocurable group introduced into the molecule, the degree of curing of the coating composition can be further increased.

In one embodiment of the present invention, the molecular weight of the compound having a thermosetting group or a photo-curable group introduced into the molecule is from 100 g / mol to 1,500 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 invention, the polymer compound 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 carbazole 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.

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

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

In one embodiment of the present invention, the p-doped material may be represented by any one of the following formulas (4-1) to (4-3), but is not limited thereto.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

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% by weight to 50% by weight based on the carbazole derivative of the formula (1).

In one embodiment of the present disclosure, the content of the p-doped material comprises 0 to 30% by weight based on the total solids content of the coating composition. The

In one embodiment, the amount of the p-doping material is preferably 1 to 30% by weight based on the total solid content of the coating composition. In another embodiment, the content of the p- More preferably, the coating composition comprises 10 to 30 wt% based on the total solids content of the coating composition.

In yet another embodiment, the coating composition comprises a single molecule comprising a thermosetting group or a photocurable group; Or a monomer capable of forming a polymer by heat. A single molecule containing a thermosetting group or a photocurable 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.

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 thermosetting group or a photopolymerizable group; Or a terminal molecule containing a terminal group capable of forming a polymer by heat.

Monomers including the thermosetting group or the photocurable group; Or monomers comprising an end group capable of forming a polymer by thermal polymerization include aryl, such as phenyl, biphenyl, fluorene, naphthalene; Arylamine; Or a single molecule in which a terminal group capable of forming a thermosetting group, a photo-curable group or a polymer by heat is substituted for the carbazole.

In another embodiment, the viscosity of the coating composition is from 2 cP to 15 cP.

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 disposed between the cathode and the anode, wherein at least one of the organic layers is formed using the coating composition, thereby including a cured product of the coating composition. The cured product of the coating composition means a cured state of the coating composition by heat treatment or light treatment.

In one embodiment of the present invention, the organic material layer including the cured product of 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 layer including the cured product of the coating composition is a light emitting layer, and the light emitting layer includes the carbazole derivative 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 one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following formula (12):

[Chemical Formula 12]

In Formula 12,

r3 is an integer of 1 or more,

Ar 1 is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,

L ₆ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted germanium group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group or may be bonded to each other to form a substituted or unsubstituted ring,

When r3 is 2 or more, the structures in parentheses are equal to or different from each other.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 12 as a dopant in the light emitting layer.

According to one embodiment of the present disclosure, L < ₆ > is a direct bond.

According to one embodiment of the present disclosure, r3 is 2.

In one embodiment of the present invention, Ar1 is a divalent pyylene group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group; Or a divalent cyclic group substituted or unsubstituted with a deuterium, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

According to one embodiment of the present invention, Ar 2 and Ar 3 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, Ar2 and Ar3 may be the same or different and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or an alkyl group Lt; / RTI >

In one embodiment of the present invention, Ar 2 and Ar 3 are the same or different and each independently represents an aryl group substituted or unsubstituted with a silyl group substituted with an alkyl group.

In one embodiment of the present invention, Ar2 and Ar3 are the same or different and each independently an aryl group substituted or unsubstituted with a trimethylsilyl group.

In one embodiment of the present specification, Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

In one embodiment of the present invention, Ar2 and Ar3 are the same or different and each independently a phenyl group substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group.

In one embodiment of the present invention, Ar2 and Ar3 are the same or different and each independently a biphenyl group substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group .

In one embodiment of the present invention, Ar2 and Ar3 are the same or different and each is a terphenyl group substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group .

In one embodiment of the present invention, Ar2 and Ar3 are the same or different and each independently represent a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

According to one embodiment of the present disclosure, Ar2 and Ar3 may be the same or different,

Each of which is independently a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group, or a heteroaryl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, Ar 2 and Ar 3 are the same or different and each independently represent a dibenzofurane group substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a trimethylsilyl group, to be.

According to one embodiment of the present disclosure, Formula 12 is selected from the following compounds.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following formula (13).

[Chemical Formula 13]

In the above formula (13)

Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,

G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 13 as a host of the light emitting layer.

In one embodiment of the present specification, Ar4 and Ar5 are the same or different and each independently a substituted or unsubstituted polycyclic aryl group.

In one embodiment of the present specification, Ar4 and Ar5 are the same or different and each independently a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar4 and Ar5 are the same or different and each independently a substituted or unsubstituted 1-naphthyl group.

In one embodiment of the present specification, Ar4 and Ar5 are 1-naphthyl groups.

In one embodiment of the present specification, G1 to G8 are hydrogen.

In one embodiment of this disclosure, Formula 13 is selected from the following compounds.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 12 as a dopant in the light emitting layer, and includes the compound represented by Formula 13 as a host in the light emitting 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.

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 carbazole derivative.

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 PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on a substrate 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.

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 85 캜 to 300 캜.

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 invention, when the coating composition contains no additive, it is preferable that the coating is heat-treated at a temperature of 100 ° C to 300 ° C to perform crosslinking, and crosslinking proceeds at a temperature of 150 ° C to 250 ° C . In addition, the coating compositions herein may further comprise initiators, but are more preferably not used.

In the case where the organic compound layer formed using the coating composition includes the heat treatment or light treatment step, an organic compound layer including a structure in which a plurality of carbazole derivatives contained in the coating composition forms a crosslink to form a thin film 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.

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

In one embodiment of the present invention, the coating composition containing the carbazole derivative may be a coating composition in which a polymer binder is mixed and dispersed.

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 polymer 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.

In addition, the carbazole derivative according to one embodiment of the present invention includes carbazole and amine groups, so that the carbazole derivative alone may be contained in the organic material layer, or the coating composition containing the carbazole derivative may be thinned through heat treatment or light treatment Or may be incorporated as a copolymer using coating compositions 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 metal and oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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, a hole injecting effect for the anode, an excellent hole injecting effect for a light emitting layer or a light emitting material, 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 with a low work function followed by an aluminum layer or 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 heterocyclic compound may be included in an organic solar cell or an organic transistor in addition to an 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.

The compounds having the structure of Formula 1 may be prepared by the following starting materials or intermediate compounds, but are not limited thereto.

[Formula A-1-1] [Formula A-2-1] [Formula A-3-1]

[Formula A-4-1] [Formula A-5-1] [Formula A-6-1]

The amine compounds capable of reacting with the above-mentioned formulas A-1-1 to A-6-1 may be of the following kinds, but are not limited thereto. In addition, the compounds below the formula (C-1) correspond to the -NL ₅ D ₁ skeleton within the above general formula structure.

 [Formula C-1] [Formula C-2] [Formula C-3]

[Formula C-4] [Formula C-5] [Formula C-6]

[Chemical formula C-7] [Chemical formula C-8]

[Formula C-9] [Formula C-10] Formula [C-11]

[Chemical formula C-12] [Chemical formula C-13]

[Chemical formula C-14] [Chemical formula C-15]

[Chemical formula C-16] [Chemical formula C-17]

[Chemical formula C-18] [Chemical formula C-19]

[Chemical formula C-20] [Chemical formula C-21]

[Chemical formula C-22]

[Chemical formula C-23]

[Formula C-24] [Formula C-25] Formula [C-26]

[Formula C-27] [Formula C-28] Formula [C-29]

[Formula C-30] [Formula C-31]

(C-32)

Production Example 1-1-1. Preparation of Formula 1-1-1

≪ Preparation of compound (B-1-1)

[Formula A-1-1] [Formula B-1-1]

Aniline (0.58 g, 6.2 mmol) was dissolved in 200 ml of xylene and sodium tert-butoxide (4.76 g, 49.6 mmol), bisdibenzylidene acetone palladium (0.015 g, 0.115 mmol) and 0.055 ml (0.115 mmol) of a 50 wt% tri-tertiary-butylphosphine toluene solution were added thereto, and the mixture was refluxed in a nitrogen atmosphere for 5 hours.

Distilled water was added to the reaction solution, and the reaction was terminated and the organic layer was extracted. The reaction mixture was subjected to column separation with a solvent of n-hexane / ethyl acetate = 6/1, followed by stirring with ethyl alcohol (EtOH) and hexane, followed by filtration and vacuum drying. The compound was dissolved in THF without further purification, and then 20 mL of 2N HCl was added and stirred. Then, the organic layer was extracted with EA. The organic layer was dried over anhydrous magnesium sulfate and then filtered and distilled under reduced pressure. The residue was subjected to column separation using a solvent of n-hexane / ethyl acetate = 6/1 and then stirred with CH ₂ Cl ₂ and ethyl alcohol (EtOH) 1-1 (2.66 g, yield 68%). MS: [M + H] < + > = 632

<Preparation of Formula 1-1-1>

[Formula B-1-1] [Formula 1-1-1]

(Bromomethyl) triphenylphosphonium bromide (5.18 g, 10.64 mmol) was dissolved in tetrahydrofuran (THF) (100 mL), and then 1 eq. Of n-butyllithium (n- BuLi) (2.5 M in HEX, 4.26 mL, 10.64 mmol) were added thereto, and the mixture was stirred for 20 minutes. After raising the reaction temperature to 0 ° C, the compound of formula (B-1-1) (2 g, 3.17 mmol) was added to the reaction mixture and stirred at the same temperature for 1 hour. Distilled water was added to the reaction solution, and the organic layer was extracted. The reaction solution was concentrated, dissolved in methylene chloride (MC), and recrystallized with etheral alcohol (EtOH) to obtain the compound of formula 1-1-1 (1.28 g, yield 84%). MS: [M + H] &lt; + &gt; = 628

Production Example 1-2-1. Preparation of Formulas 1-2-1

&Lt; Preparation of compound of formula (B-2-1)

[Formula A-1-1] [Formula B-2-1]

In the production example of the above formula (1-1-1), the same reaction was carried out except that N1, N1-diphenylbenzene-1,4-diamine was used in place of aniline to obtain the compound of formula (B-2-1). MS: M + H] &lt; + &gt; = 799

<Preparation of Formulas 1-2-1>

     [Formula B-2-1] [Formula 1-2-1]

In the production example of the formula 1-1-1, the same reaction was conducted except that the compound of the formula B-2-1 was used instead of the compound of the formula B-1-1 to obtain the compound of the formula 1-2-1. MS: [M + H] &lt; + &gt; = 796

Production Example 1-3-1. Preparation of Formula 1-3-1

&Lt; Preparation of compound of formula (B-3-1)

[Formula A-1-1] [Formula B-3-1]

In the same manner as in Production Example 1-1-1 except that N4, N4-diphenyl- [1,1'-biphenyl] -4,4'-diamine was used in place of aniline, -3-1. MS: [M + H] &lt; + &gt; = 876

<Preparation of Formulas 1-3-1>

[Formula B-3-1] [Formula 1-3-1]

In the production example of the formula 1-1-1, the same reaction was conducted except that the compound of the formula B-3-1 was used instead of the compound of the formula B-1-1 to obtain the compound of the formula 1-3-1. MS: [M + H] &lt; + &gt; = 872

Production Example 1-4-1. Preparation of Formula 1-4-1

&Lt; Preparation of compound of formula (B-4-1) >

[Formula A-2-1] [Formula B-4-1]

In the production example of the above-mentioned formula (1-1-1), the same method as in (A-2-1) was used instead of the formula (A-1-1) except that N1, N1-diphenylbenzene- MS: [M + H] &lt; + &gt; = 1040

<Preparation of Chemical Formula 1-4-1>

          [Formula B-4-1] [Formula 1-4-1]

In the production example of the above formula (1-1-1), the same procedure was followed except that the compound of the formula (B-4-1) was used instead of the compound of the formula (B-1-1) to obtain the compound of the formula (1-4-1). MS: [M + H] &lt; + &gt; = 48

Production Example 1-5-1. Preparation of Formula 1-5-1

&Lt; Preparation of compound of formula (B-5-1)

[Formula A-2-1] [Formula B-5-1]

In the production example of the above formula (1-1-1), a compound represented by the formula (A-2-1) is used in place of the compound represented by the formula (A-1-1), an N4, N4-diphenyl- [ '- diamine. MS: [M + H] &lt; + &gt; = 1116

<Preparation of Formulas 1-5-1>

        [Formula B-5-1] [Formula 1-5-1]

In the production example of the above formula (1-1-1), the same procedure was followed except that the compound of the formula (B-5-1) was used instead of the compound of the formula (B-1-1) to obtain the compound of the formula (1-5-1). MS: [M + H] &lt; + &gt; = 1024

Production Example 1-6-1. Preparation of 1-6-1

&Lt; Preparation of compound of formula (B-6-1) >

[Formula A-2-1] [Formula B-6-1]

In the production example of the above-mentioned formula (1-1-1), the same method as in (A-2-1) was used instead of the formula (A-1-1) except that [1,1'-biphenyl] MS: [M + H] &lt; + &gt; = 936

<Preparation of 1-6-1>

        [Formula B-6-1] [Formula 1-6-1]

In the production example of the formula 1-1-1, the same reaction was conducted except that the compound of the formula B-6-1 was used instead of the compound of the formula B-1-1 to obtain the compound of the formula 1-6-1. MS: [M + H] &lt; + &gt; = 857

Production Example 1-7-1. Preparation of 1-7-1

&Lt; Preparation of compound of formula (B-7-1)

[Formula A-1-1] [Formula B-7-1]

In the production example of the above formula (1-1-1), the same procedure was followed except that [1,1'-biphenyl] -4-amine was used instead of aniline to obtain the compound of formula (B-7-1). MS: M + H] &lt; + &gt; = 708

<Preparation of 1-7-1>

   [Formula B-7-1] [Formula 1-7-1]

In the production example of the above formula (1-1-1), the same procedure was followed except that the compound of the formula (B-7-1) was used instead of the compound of the formula (B-1-1) to obtain the compound of the formula (1-7-1). MS: [M + H] &lt; + &gt; = 704

Production Example 1-8-1. Preparation of 1-8-1

&Lt; Preparation of compound of formula (B-8-1) >

[Formula A-1-1] [Formula B-8-1]

In the same manner as in Production Example 1-1-1, except that 4- (9,9-dimethyl-9H fluoren-2-yl) aniline was used in place of aniline, MS: [M + H] &lt; + &gt; = 825

<Preparation of 1-8-1>

[Formula B-8-1] [Formula 1-8-1]

In the production example of the above formula (1-1-1), the same reaction was carried out except that the compound of the formula (B-8-1) was used instead of the compound of the formula (B-1-1) to obtain the compound of the formula (1-8-1). MS: [M + H] &lt; + &gt; = 821

Experimental Example  1. Formation of Coating Layer Using Coating Composition

Example

The coating composition is a compound represented by the formula (1) of the present invention as shown in Table 1 below. p-doping material; And an organic solvent (cyclohexanone). Also, the coating composition was formed by spin coating as shown in Table 1, and the film was baked at 250 占 폚 or less.

The following p doping materials are dopants such as the following chemical formulas (2-1), (3-1) and (4-1), but are not limited thereto.

[Formula 2-1]

[Formula 3-1]

[Formula 4-1]

Comparative Example  1 and 2

The coating composition was prepared in the same manner as in Example 1, except that the compound represented by Formula 1-1 was used instead of the compound represented by Formula 1 and the dopant used in Formula 2-1 or 3-1 was used.

[Formula 1-1]

Comparative Example  3

In the above examples, the compound represented by Formula 1-2 was used in place of the compound represented by Formula 1, and the coating composition was prepared in the same manner as in Example 1 using the compound of Formula 3-1 as the dopant.

[Formula 1-2]

               VNPB

Coating composition compound p- dopant Compound: p - dopant Spin speed (rpm) /
Time (s) Firing temperature
(° C) C1-1-1 Formula 1-1-1 2-1 0.8: 0.2 1000/60 230/30 C1-1-2 Formula 1-1-1 3-1 0.8: 0.2 1000/60 230/30 C1-1-3 Formula 1-1-1 4-1 0.8: 0.2 1000/60 230/30 C2-1-1 1-2-1 2-1 0.8: 0.2 1000/60 230/30 C2-1-2 1-2-1 3-1 0.8: 0.2 1000/60 230/30 C2-1-3 1-2-1 4-1 0.8: 0.2 1000/60 230/30 C3-1-1 1-3-1 2-1 0.8: 0.2 1000/60 230/30 C3-1-2 1-3-1 3-1 0.8: 0.2 1000/60 230/30 C3-1-3 1-3-1 4-1 0.8: 0.2 1000/60 230/30 C4-1-1 1-4-1 2-1 0.8: 0.2 1000/60 230/30 C4-1-2 1-4-1 3-1 0.8: 0.2 1000/60 230/30 C4-1-3 1-4-1 4-1 0.8: 0.2 1000/60 230/30 C5-1-1 1-5-1 2-1 0.8: 0.2 1000/60 230/30 C5-1-2 1-5-1 3-1 0.8: 0.2 1000/60 230/30 C5-1-3 1-5-1 4-1 0.8: 0.2 1000/60 230/30 C6-1-1 1-6-1 2-1 0.8: 0.2 1000/60 230/30 C6-1-2 1-6-1 3-1 0.8: 0.2 1000/60 230/30 C6-1-3 1-6-1 4-1 0.8: 0.2 1000/60 230/30 C7-1-1 1-7-1 2-1 0.8: 0.2 1000/60 230/30 C7-1-2 1-7-1 3-1 0.8: 0.2 1000/60 230/30 C7-1-3 1-7-1 4-1 0.8: 0.2 1000/60 230/30 C7-2-1 1-8-1 2-1 0.8: 0.2 1000/60 230/30 C7-2-2 1-8-1 3-1 0.8: 0.2 1000/60 230/30 C7-2-3 1-8-1 4-1 0.8: 0.2 1000/60 230/30 C1-7-4 Formula 1-1-1:
1-7-2 3-1 0.8: 0.2 1000/60 230/30 C7-7-4 Formula 1-7-1:
1-7-2 3-1 0.8: 0.2 1000/60 230/30 Comparative Example 1 (1-1) 2-1 0.8: 0.2 1000/60 230/30 Comparative Example 2 (1-1) 3-1 0.8: 0.2 1000/60 230/30 Comparative Example 3 1-2 3-1 0.8: 0.2 1000/60 230/30

The mixing ratio of the compounds of the coating compositions C1-7-4 and C7-7-4 is 1: 1 respectively.

Experimental Example  2. Film retention test of coating layer

To confirm the film retention rate of the coating layer using the coating composition shown in Table 1, the toluene solvent was spin-treated on the upper part of the film.

The film formed using the coating compositions C1-1-1 to C7-2-3 with respect to toluene as compared with the comparative examples 1 to 3, and / or the mixture of C1-7-4 and C7- 7-4, it was confirmed that the cross-linkable functional groups formed crosslinking, and that the chemical resistance and the membrane retention were high.

Example  One

The coating composition C1-1-2 was spin-coated at a spin speed of 1000 rpm for 60 seconds and then heated and fired at 230 DEG C for 30 minutes on a hot plate to form a thin film.

After immersing in toluene for 10 min and removing it, UV-Visible spectroscopy confirmed that the membrane retention was 100%.

FIG. 2 is a graph showing a film retention rate of a thin film prepared from the coating composition C1-1-2 by UV-Visible spectroscopy.

Comparative Example  4

Coating Composition Comparative Example 1 was formed into a thin film in the same manner as in Example 1.

After immersing in toluene and cyclohexanone for 10 minutes and taking out, it was confirmed by UV-Visible spectroscopy that the membrane retention was lower than that of Example 1.

FIG. 3 is a graph showing the film retention of the thin film prepared in Comparative Example 1 by UV-Visible spectroscopy.

Experimental Example  3. Fabrication of organic light emitting devices

Example  2

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

On this ITO transparent electrode, the coating composition C1-1-1 described in the following table was spin-coated to form a hole injection layer having a thickness of 300 A, and the coating composition was cured on a hot plate for 30 minutes under an atmosphere of N ₂ . Thereafter, the resultant was transferred to a vacuum evaporator, and then Compound 1 was vacuum-deposited on the hole injection layer to form a hole transport layer.

[Compound 1] [Compound 2]

[Compound 3] [Compound 4]

Next, Compound 2 and Compound 3 were vacuum-deposited to a thickness of 300 Å at a concentration of 8% on the hole transport layer to form a light emitting layer. Compound 4 was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer. Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and a thickness of 2000 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the cathode LiF was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec, and the degree of vacuum during deposition was 2 × 10 ^-7 to 5 × 10 ^-8 torr. &Lt; / RTI &gt;

Example  3

An organic light emitting device was fabricated in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced with the coating composition C1-1-2 in place of the coating composition C1-1-1.

Example  4

An organic light emitting device was prepared in the same manner as in Example 1 except that the hole injecting layer in Example 2 was replaced with the coating composition C1-1-3 in place of the coating composition C1-1-1.

Example  5

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced with the coating composition C2-1-2 in place of the coating composition C1-1-1.

Example  6

An organic light emitting device was fabricated in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced with the coating composition C2-1-3 in place of the coating composition C1-1-1.

Example  7

An organic light emitting device was prepared in the same manner as in Example 1 except that the hole injection layer in Example 2 was replaced with the coating composition C3-1-2 in place of the coating composition C1-1-1.

Example  8

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced with the coating composition C4-1-2 in place of the coating composition C1-1-1.

Example  9

An organic light emitting device was prepared in the same manner as in Example 1 except that the hole injection layer in Example 2 was replaced with the coating composition C5-1-2 in place of the coating composition C1-1-1.

Example  10

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced with the coating composition C5-1-3 in place of the coating composition C1-1-1.

Example  11

An organic light emitting device was prepared in the same manner as in Example 1 except that the hole injection layer in Example 2 was replaced by the coating composition C6-1-2 instead of the coating composition C1-1-1.

Example  12

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced with the coating composition C7-1-2 in place of the coating composition C1-1-1.

Example  13

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced with the coating composition C7-1-3 in place of the coating composition C1-1-1.

Example  14

An organic light emitting device was prepared in the same manner as in Example 1 except that the hole injection layer in Example 2 was replaced with the coating composition C7-2-2 in place of the coating composition C1-1-1.

Example  15

An organic light emitting device was prepared in the same manner as in Example 1 except that the hole injecting layer in Example 2 was replaced with the coating composition C1-7-4 in place of the coating composition C1-1-1.

Comparative Example  5

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole injection layer in Example 2 was replaced by Comparative Example 1 in place of the coating composition C1-1-1.

The results of measuring the driving voltage and the luminous efficiency at an electric current density of 10 mA / cm &lt; ² &gt; are shown in Table 2 below.

Device structure Coating composition The driving voltage (V) Driving current
(mA / cm ² ) Current efficiency
(cd / A) Power efficiency
(l m / W) Example 2 C1-1-1 6.67 10 5.09 2.57 Example 3 C1-1-2 6.24 10 4.76 2.40 Example 4 C1-1-3 6.12 10 4.62 2.33 Example 5 C2-1-2 6.42 10 4.90 2.47 Example 6 C2-1-3 6.74 10 4.76 2.40 Example 7 C3-1-2 6.74 10 5.14 2.59 Example 8 C4-1-2 6.93 10 5.28 2.66 Example 9 C5-1-2 6.80 10 6.80 2.62 Example 10 C5-1-3 6.99 10 5.33 2.77 Example 11 C6-1-2 7.05 10 5.37 2.71 Example 12 C7-1-2 7.11 10 5.43 2.74 Example 13 C7-1-3 6.18 10 4.71 2.38 Example 14 C7-2-2 6.12 10 4.66 2.35 Example 15 C1-7-4 7.02 10 5.36 2.70 Comparative Example 5 Comparative Example 1 7.49 10 3.96 2.00

As a result of the above Table 2, derivatives of the formula (1) according to one embodiment of the present invention

It is possible to form a uniform coating layer using the coating composition and to apply the composition to an organic light emitting device.

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

Claims (22)

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

In Formula 1,
L ₁ to L ₅ are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
D ₁ is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylamine group,
Ra and Rb are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylaryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
r1 and r2 are each an integer of 0 to 7,
When r1 and r2 are 2 or more, the substituents in parentheses are the same or different from each other,
X ₁ and X ₂ are the same or different from each other, and each independently is a thermosetting group or a photocurable group. The carbazole derivative according to claim 1, wherein the thermosetting group or photocurable group is any one of the following structures:

In the above structure,
A 1 to A 3 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. The method according to claim 1,
(1) is a carbazole derivative represented by the following formula (2) or (3):
(2)

(3)

In the general formula (2) or (3)
L ₃ to L ₅ , Ra, Rb, r ₁ , r ₂ , X ₁ , X ₂ and D ₁ are as defined in formula (1)
R11 and R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,
m1 and m2 are each an integer of 0 to 4,
When m1 and m2 are each 2, the substituents in the parentheses are the same or different from each other. The method according to claim 1,
(1) is represented by any one of the following formulas (4) to (7):
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 4 to 7,
L ₅ , Ra, Rb, r ₁ , r 2, D ₁ , X ₁ and X ₂ are the same as defined in formula (1)
R13 to R16 and R101 and R112 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,
m3 to m6 and p1 to p12 each are an integer of 0 to 4,
When m3 to m6 and p1 to p12 are each 2 or more, the substituents in the parentheses are the same or different from each other. The method according to claim 1,
(1) is represented by any one of the following formulas (8) to (11):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the general formulas (8) to (11)
L ₅ , D _1, X ₁ , X ₂ , R a, R b, r 1 and r 2 are the same as defined in formula (1)
R21 to R32 and R113 to R124 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group,
n1 to n4 and n9 to n12 each is an integer of 0 to 5,
n5 to n8 and p13 to p24 each is an integer of 0 to 4,
When n1 to n8 and p13 to p24 are each 2 or more, the substituents in the parentheses are the same or different from each other. The method according to claim 1,
D1 is a carbazole derivative represented by the following structural formula:

In the above structural formulas,
R ₁ to R ₃ are the same or different and each independently hydrogen; An amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,
q1 to q3 each represent an integer of 0 to 5,
When q1 to q3 are 2 or more, the structures in parentheses are equal to or different from each other. The method of claim 6,
R ₂ and R ₃ are the same or different and are each independently hydrogen; An amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method of claim 6,
R ₁ is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted alkyl group. The carbazole derivative according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas.

A coating composition comprising a carbazole derivative according to any one of claims 1 to 9. 11. The coating composition of claim 10, wherein the coating composition further comprises a p-doping material. The method of claim 11,
Wherein the p-doped material is represented by any one of the following formulas (2-1) to (4-1):
[Formula 2-1]

[Formula 3-1]

[Formula 4-1]

11. The composition of claim 10, wherein the coating composition comprises a monomolecule comprising a thermosetting group or a photocurable group; Or a monomolecule comprising an end group capable of forming a polymer by heat. Cathode;
Anode; And
And at least one organic layer provided between the cathode and the anode,
Wherein at least one of said organic layers comprises a cured product of the coating composition of claim 10,
Wherein the cured product of the coating composition is in a cured state by heat treatment or light treatment. 15. The method of claim 14,
Wherein the organic layer including the cured product of the coating composition is a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes. 15. The method of claim 14,
Wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following Formula 12:
[Chemical Formula 12]

In Formula 12,
r3 is an integer of 1 or more,
Ar 1 is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,
L ₆ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group or may be bonded to each other to form a substituted or unsubstituted ring,
When r3 is 2 or more, the structures in parentheses are equal to or different from each other. 18. The method of claim 16,
Wherein L ₆ is a direct bond, Ar1 is 2 and the monovalent pie group, Ar2 and Ar3 is a silyl group substituted or unsubstituted aryl group substituted with an alkyl group independently from each other the same or different and each, r3 is 2 to the organic Light emitting element. 15. The method of claim 14,
Wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following Formula 13:
[Chemical Formula 13]

In the above formula (13)
Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group. 19. The method of claim 18,
Wherein Ar4 and Ar5 are 1-naphthyl groups, and G1 to G8 are hydrogen. 18. The method of claim 16,
Wherein the light emitting layer further comprises a compound represented by Formula 13 below:
[Chemical Formula 13]

In the above formula (13)
Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group. 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 10. 22. The method of claim 21, wherein forming the organic layer formed using the coating composition comprises:
Coating the coating composition on the cathode or anode; And
And a step of heat-treating or light-treating the coated coating composition.

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