KR20200124013A - NOVEL COMPOUND For Organic light emitting diode AND COATING COMPOSITION FOR ORGANIC LAYER COMPRISING THE SAME - Google Patents

Abstract

The present invention relates to a compound represented by formula 1 and a coating liquid composition including the same, wherein formula 1 is as described in the detailed description of the invention. The compound of the present invention can have high solvent resistance.

Description

Novel compound for organic light emitting device and coating liquid composition for organic film material containing the same {NOVEL COMPOUND For Organic light emitting diode AND COATING COMPOSITION FOR ORGANIC LAYER COMPRISING THE SAME}

The present invention relates to a novel compound for an organic light emitting device and a coating liquid composition for an organic film material comprising the same, and in more detail, a solution process is possible, and when used in an organic light emitting device, high luminous efficiency, low voltage driving, and high heat resistance , It relates to a compound for an organic light emitting device capable of realizing device characteristics such as high solvent resistance, color purity, and long life, and a coating solution composition for an organic film material comprising the same.

The organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. In general, an organic light emitting device (OLED) is a display using an organic material that emits light by itself. When an electric field is applied to the organic material, electrons and holes are transferred from the cathode and the anode, respectively. It combines within a substance, and the energy generated at this time uses organic electroluminescence that is emitted as light.

That is, the organic light emitting device has a structure in which an organic material capable of emitting light is interposed between two electrodes in the form of a thin film, and is largely classified into a vacuum deposition type and a solution process type depending on how the organic thin film is formed.

The vacuum evaporation method is a process suitable for low molecular weight materials with low molecular weight. When heat is applied to the material in a high vacuum of 10 ^-6 torr or less, the material is vaporized and dispersed inside the chamber to form a thin film by condensing on a substrate with a relatively low temperature. .

The vacuum evaporation method is the most used method in current companies because it is easy to realize the high lifespan and excellent efficiency characteristics of the device, but the amount of material used to form the pixel pattern is condensed on the mask when manufacturing the organic light emitting device using the vacuum deposition method. However, since it is less than the amount applied to the inner wall of the chamber, it shows a low material use efficiency of about 10%.

In addition, the exponential increase in equipment operating costs due to the increase in the substrate size required to increase the production volume and decrease the production cost is acting as a challenge in lowering the production cost. There was a problem.

Meanwhile, as a method that can be used for both a low molecular weight material and a high molecular weight polymer material, there is a solution process method, and representative methods of the solution process method include inkjet printing and spin coating.

The solution process method is a method of forming a thin film by dissolving a material in a solvent to make a thin film. When using the inkjet printing method, the material use efficiency can be maximized. Because a fine pattern is possible without the use of a mask, it is an advantageous manufacturing method for large area. There is an advantage that it can be used.

However, the solution process without crosslinking causes a problem of deteriorating the characteristics of the device and lowering the process yield because there is a problem that the lower film is damaged by eroding the lower film due to the solvent used when the upper film is formed. Crosslinking is essentially required to prevent erosion of the lower film. In addition, a compound capable of forming a crosslinking bond, which has a high solubility in an organic solvent before crosslink formation and has a low solubility in an organic solvent after crosslink formation, should be used.

There are largely a crosslinking method through light and a crosslinking method through heat as a method of forming crosslinking. Crosslinking by light has the advantage of enabling rapid crosslinking at low temperatures, but it requires a photoinitiator, which acts as an impurity in the device, leading to a problem of deterioration of properties. On the other hand, crosslinking through heat requires a high temperature for a long time, but is known to improve the characteristics of the device.

As a related art, Korean Patent Publication No. 10-1105242 (2012.01.13) relates to a blue light-emitting compound capable of a solution process, and iridium having picolinic acid or picolinic acid-en-oxide derivative as an auxiliary ligand A blue light-emitting compound is disclosed, and Korean Patent Laid-Open Publication No. 10-2015-0105201 (2015.09.16) relates to a novel organic light-emitting compound, and discloses a carbazole-based organic compound.

However, despite the prior art including the prior art, the development of a stable and efficient material for an organic light emitting device capable of a solution process has not yet been sufficiently developed, and therefore, the need for development of a new material is continuously required.

Korean Registered Patent Publication No. 10-1105242 (2012.01.13) Korean Patent Application Publication No. 10-2015-0105201 (2015.09.16)

Therefore, the technical problem to be achieved by the present invention is to provide a novel organic compound for an organic light emitting device that can be used in a solution process.

In addition, the technical problem to be achieved by the present invention is that by using the organic compound as a coating liquid composition for an organic film material in an organic light emitting device, when used in an organic light emitting device, it has excellent solubility in an organic solvent, enabling a solution process and high light emission. It is to provide a coating liquid composition for an organic film material capable of implementing device characteristics such as efficiency, low voltage driving, high heat resistance, high solvent resistance, color purity, and long life, and an organic light emitting device including the same.

For the above object, the present invention provides a compound represented by the following formula (1).

[Formula (1)]

In the above formula (1),

The linking groups L ₁ to L ₄ are each the same or different, and are independently selected from a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C50 alkylene group. Which one is

The * means a linking group L ₁ or L ₂ and a bonding site bonding to the carbon atom of each phenyl ring bonded to the anthracene group,

The carbon atom of the aromatic ring in the anthracene group, or the carbon atom of the aromatic ring not bonded to L ₁ or L ₂ in each phenyl ring bonded to the anthracene group is bonded to hydrogen or deuterium,

The substituents Ar ₁ and A _r2 are each the same or different, and are each independently any one selected from the following Structural Formulas 1 to 3,

[Structural Formula 1]

[Structural Formula 2] [Structural Formula 3]

상기 구조식 1에서,

In the above structural formula 1,

At least one of the substituents R ₇ to R ₁₁ is a single bond connected to *** of the structural formula Q1, and when Q1 is 2 or more, each of Q1 is the same as or different from each other,

The substituents not bonded to Q1 in the substituents R ₇ to R ₁₁ are the same or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted Or any one selected from an unsubstituted C ₆ -C ₃₀ arylsilyl group, a cyano group, a nitro group, and a halogen group,

The substituent R ₁₂ is selected from hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₅ alkyl group,

In the above Structural Formulas 1 to 3, the ** means a bonding site connected to L ₃ or L ₄ ,

The linking groups R ₁ and R ₂ are the same as or different from each other, and each independently a single bond, O, S, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₂ -C ₃₀ Al Kenylene group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkylene group, a substituted or unsubstituted C ₂ -C ₃₀ alkynylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or Unsubstituted C ₂ -C ₃₀ heterocycloalkylene group, substituted or unsubstituted C ₆ -C ₅₀ arylene group, substituted or unsubstituted C ₂ -C ₅₀ heteroarylene group, substituted or unsubstituted C ₁ -C ₃₀ is an oxyalkylene group (-O-alkylene-), any one linking group selected from the following structural formula La and structural formula Lb,

[Structural Formula La] [Structural Formula Lb]

In the above structural formula La,

The substituents R ₁₇ to R ₁₈ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or Any one selected from an unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, a cyano group, and a halogen group,

'은 서로 동일하거나 상이하고, 또한 m₂이 2이상인 경우에 괄호내 각각의'

'은 서로 동일하거나 상이하고,The m ₁ and m2 are each the same or different, and independently of each other, are an integer of 1 to 10, but when m ₁ is 2 or more, each'in parentheses'

'Is the same or different from each other, and each in parentheses when m ₂ is 2 or more'

'Is the same or different from each other,

In the structural formula Lb,

R ₂₀ is Hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted It is any one selected from a C ₁ -C ₃₀ alkoxy group, a cyano group, and a halogen group,

M ₃ is an integer of 1 to 4, but m ₃ is 2 or more

In the case of, each R ₂₀ is the same as or different from each other,

'은 서로 동일하거나 상이하고, 또한 m₅가 2이상인 경우에 괄호내 각각의'

'은 서로 동일하거나 상이하고,The m ₄ and m5 are each the same or different, and independently of each other are an integer of 1 to 10, but when m ₄ is 2 or more, each'in parentheses'

'Is the same or different from each other, and if m ₅ is 2 or more, each in parentheses'

'Is the same or different from each other,

The n ₁ and n ₂ are the same as or different from each other, and each independently an integer of 1 to 4, but when n ₁ is 2 or more, each'Ar ₁ -L ₃ -R ₁ -L ₁ -'in parentheses is each The same or different, and when n ₂ is 2 or more, each'Ar ₂ -L ₄ -R ₂ -L ₂ -'in parentheses is the same or different from each other.

In addition, the present invention provides a coating liquid composition for an organic film material comprising at least one or more compounds represented by the formula (1).

In addition, the present invention is a first electrode, a second electrode opposite to the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the coating liquid composition for the organic film material of the present invention.

In addition, the present invention provides an electronic device including the organic light emitting device.

The coating liquid composition for an organic film material comprising the compound represented by the formula (1) according to the present invention has excellent solubility in an organic solvent, so that a solution process is possible, and in the case of the prepared organic film, it can have high solvent resistance.

In addition, the organic light-emitting device manufactured by using the coating liquid composition for the organic film material may have high luminous efficiency, low voltage driving, high heat resistance, color purity, and long lifespan compared to the organic light-emitting device manufactured by a conventional solution process.

Hereinafter, the present invention will be described in more detail. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by an expert skilled in the art to which the present invention belongs. In general, the nomenclature used in this specification is well known and commonly used in the art.

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

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

[Formula (1)]

In the above formula (1),

The linking groups L ₁ to L ₄ are each the same or different, and are independently selected from a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C50 alkylene group. Which one is

The * means a linking group L ₁ or L ₂ and a bonding site bonding to the carbon atom of each phenyl ring bonded to the anthracene group,

The carbon atom of the aromatic ring in the anthracene group, or the carbon atom of the aromatic ring not bonded to L ₁ or L ₂ in each phenyl ring bonded to the anthracene group is bonded to hydrogen or deuterium,

The substituents Ar ₁ and A _r2 are each the same or different, and are each independently any one selected from the following Structural Formulas 1 to 3,

[Structural Formula 1]

[Structural Formula 2] [Structural Formula 3]

상기 구조식 1에서,

In the above structural formula 1,

At least one of the substituents R ₇ to R ₁₁ is a single bond connected to *** of the structural formula Q1, and when Q1 is 2 or more, each of Q1 is the same as or different from each other,

The substituents not bonded to Q1 in the substituents R ₇ to R ₁₁ are the same or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted Or any one selected from an unsubstituted C ₆ -C ₃₀ arylsilyl group, a cyano group, a nitro group, and a halogen group,

The substituent R ₁₂ is selected from hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₅ alkyl group,

In the above Structural Formulas 1 to 3, the ** means a bonding site connected to L ₃ or L ₄ ,

The linking groups R ₁ and R ₂ are the same as or different from each other, and each independently a single bond, O, S, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₂ -C ₃₀ Al Kenylene group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkylene group, a substituted or unsubstituted C ₂ -C ₃₀ alkynylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or Unsubstituted C ₂ -C ₃₀ heterocycloalkylene group, substituted or unsubstituted C ₆ -C ₅₀ arylene group, substituted or unsubstituted C ₂ -C ₅₀ heteroarylene group, substituted or unsubstituted C ₁ -C ₃₀ is an oxyalkylene group (-O-alkylene-), any one linking group selected from the following structural formula La and structural formula Lb,

[Structural Formula La] [Structural Formula Lb]

In the above structural formula La,

The substituents R ₁₇ to R ₁₈ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or Any one selected from an unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, a cyano group, and a halogen group,

'은 서로 동일하거나 상이하고, 또한 m₂이 2이상인 경우에 괄호내 각각의'

'은 서로 동일하거나 상이하고,The m ₁ and m2 are each the same or different, and independently of each other, are an integer of 1 to 10, but when m ₁ is 2 or more, each'in parentheses'

'Is the same or different from each other, and each in parentheses when m ₂ is 2 or more'

'Is the same or different from each other,

In the structural formula Lb,

R ₂₀ is Hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted It is any one selected from a C ₁ -C ₃₀ alkoxy group, a cyano group, and a halogen group,

The m ₃ is an integer of 1 to 4, but when m ₃ is 2 or more, each R ₂₀ is the same or different from each other,

'은 서로 동일하거나 상이하고, 또한 m₅가 2이상인 경우에 괄호내 각각의'

'은 서로 동일하거나 상이하고,The m ₄ and m5 are each the same or different, and independently of each other are an integer of 1 to 10, but when m ₄ is 2 or more, each'in parentheses'

'Is the same or different from each other, and if m ₅ is 2 or more, each in parentheses'

'Is the same or different from each other,

The n ₁ and n ₂ are the same as or different from each other, and each independently an integer of 1 to 4, but when n ₁ is 2 or more, each'Ar ₁ -L ₃ -R ₁ -L ₁ -'in parentheses is each The same or different, and when n ₂ is 2 or more, each'Ar ₂ -L ₄ -R ₂ -L ₂ -'in parentheses is the same or different from each other,

Here, the'substituted' in the'substituted or unsubstituted' in the formula (1) is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, a C ₁ -C ₂₄ alkyl group, a C ₁ -C ₂₄ halogenation Alkyl group, C ₂ -C ₂₄ alkenyl group, C ₂ -C ₂₄ alkynyl group, C _{1 -24} heteroalkyl group, C ₆ -C ₂₄ aryl group, C ₇ -C ₂₄ arylalkyl group, C _2- C ₂₄ heteroaryl group, C ₂ -C ₂₄ heteroarylalkyl group, C ₁ -C ₂₄ alkoxy group, C ₁ -C ₂₄ alkylamino group, C ₆ -C ₂₄ arylamino group, C ₁ -C ₂₄ It means substituted with one or more substituents selected from the group consisting of a hetero arylamino group, a C ₁ -C ₂₄ alkylsilyl group, a C ₆ -C ₂₄ arylsilyl group, and a C ₆ -C ₂₄ aryloxy group.

On the other hand, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted C ₁ -C ₃₀ alkyl group" and "substituted or unsubstituted C ₆ -C ₅₀ aryl group" in the present invention , The range of the carbon number of the C ₁ -C ₃₀ alkyl group and the C ₆ -C ₅₀ aryl group is the entire constituting the alkyl moiety or the aryl moiety when viewed as unsubstituted without considering the substituted moiety of the substituent, respectively It means carbon number. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to a C ₆ aryl group substituted with a C ₄ butyl group.

The aryl group as a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, In addition, when the aryl group has a substituent, it may be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., and at least one hydrogen atom in the aryl group is a deuterium atom, a halogen Atom, hydroxy group, nitro group, cyano group, silyl group, amino group (-NH2, -NH(R), -N(R')(R''), R'and R" are each independently C ₁ -C ₁₀ Is an alkyl group, in this case referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, a C ₁ -C ₂₄ alkyl group, a C ₁ -C ₂₄ halogenated alkyl group, C ₂ -C ₂₄ alkenyl group, C ₂ -C ₂₄ alkynyl group, C ₁ -C ₂₄ heteroalkyl group, C ₆ -C ₂₄ aryl group, C ₇ -C ₂₄ arylalkyl group, C ₂ -C ₂₄ It may be substituted with a heteroaryl group or a C ₂ -C ₂₄ heteroarylalkyl group.

The heteroaryl group, which is a substituent used in the compound of the present invention, contains 1, 2 or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, Te in the aromatic ring in the aryl group, and the remaining ring atoms are carbon It means an aromatic system of phosphorus C ₂ -C ₂₄ , and the rings may be fused to form a ring. And at least one hydrogen atom in the heteroaryl group may be substituted with the same substituent as in the case of the aryl group.

In addition, specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one of the alkyl groups The above hydrogen atom can be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group that is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group as a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , Dimethylfurylsilyl, and the like, and at least one hydrogen atom in the silyl group may be substituted with the same substituent as in the case of the aryl group.

On the other hand, when the characteristics of the compound represented by Formula (1) according to the present invention will be described in more detail, It has a structure in which phenyl groups are bonded to both directions of anthracene, and'Ar ₁ -L ₃ -R ₁ -L ₁ -'and'Ar ₂ -L ₄ -R ₂ -L _{2 respectively} -'is characterized by a structure in which 1 to 4 are bonded, but Ar ₁ and Ar ₄ have any one substituent selected from Structural Formula 1 to Structural Formula 3, so that an addition reaction in the solution process is possible. It is characterized.

In one embodiment, the linking groups L ₁ and L ₂ may be the same as or different from each other, and may each independently be a single bond or an oxygen atom (O).

In one embodiment, the linking groups L ₃ and L ₄ may be the same as or different from each other, and may each independently be a single bond or an oxygen atom (O).

In one embodiment, the R ₁ and R ₂ are the same as or different from each other, and each independently a single bond, an oxygen atom (O), a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₂ -C ₃₀ alkenylene group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, substituted or unsubstituted C ₆ -C ₅₀ arylene group, substituted or unsubstituted C ₂ -C ₅₀ hetero It may be an arylene group or any one linking group selected from the structural formula Lb.

As an embodiment, Ar ₁ and Ar ₂ may be each of [Structural Formula 1].

As an example, only one or two of R ₇ to R ₁₁ in Structural Formula 1 may be a single bond bonded to the substituent Q1.

As an embodiment, the linking groups L ₁ , L _2, L ₃ and L ₄ may each be an oxygen atom (O) or a single bond.

In an embodiment, n ₁ and n ₂ may be the same as or different from each other, and may be 1 or 2 each independently.

Meanwhile, as a specific example of the compound represented by the formula (1) in the present invention, it may be represented by any one of compounds [1] to [120] shown in Table 1 below, but is not limited thereto.

[Table 1]

On the other hand, the present invention provides a coating liquid composition for an organic film material comprising at least one or more compounds represented by the formula (1).

The coating solution composition for an organic film material according to the present invention is excellent in solubility in an organic solvent by using the compound represented by the formula (1), and can have high solvent resistance when an organic film is formed in an organic light emitting device. So it may be suitable for solution processing.

The coating liquid composition for organic film preparation may be a solution or suspension containing a solvent, and the solvent is anisole, dimethyl anisole, xylene, o-xylene, m-xylene, p-xylene, toluene, mesh Styrene, methyl benzoate, dioxane, terrahydrofuran, methyl tetrahydrofuran, tetrahydropyran, tetralin, veratrol, chlorobenzene, N-methyl pyrrolidone, N,N-dimethylformamide, dimethyl sulfoxide And one selected from the group consisting of a combination thereof may be exemplified.

In addition, according to another embodiment of the present invention, the coating liquid composition for an organic film material may additionally include at least one of a photoinitiator, a pigment, and a dye.

Here, the photoinitiator may include ketones, ketoacetals, thioxanthones, phosphine oxides, anthraquinones, trichloromethyl triazines, oxime esters, and the like, and specific examples of such photoinitiators include phenylbiphenyl ketone , Thioxanthone, isopropyl thioxanthone, diethyl thioxanthone, benzophenone, 1-benzyl-1-dimethylamino-1- (4-morpholino-benzoyl) propane, 1-hydroxy-1-benzoyl Cyclohexane, 2-morpholyl-2-(4-methylmercapto) benzoylpropane, ethylanthraquinone, 4-benzoyl-4-methyldiphenylsulfide, benzoinbutyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2-(4-isopropyl)benzoylpropane, 4-butylbenzoyltrichloromethane, 4-phenoxybenzoyldichloromethane, diphenyl-2,4,6-trimethylbenzoylphosphine oxide, methyl benzoylformate , 1,7-bis(9-acridinyl)heptane, 2-methyl-4,6-bis(trichloromethyl)-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)- s-triazine, 2-naphthyl-4,6-bis (trichloromethyl)-s-triazine, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl ]-Ethanone-1-(O-acetyloxime), 1-(o-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone , 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione.

In addition, the pigment and dye may be at least one colorant pigment selected from the group consisting of red, green, blue, and black, and the black pigment may be a carbon black dispersion that is commonly used, but is not limited thereto.

On the other hand, the present invention is a first electrode, a second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the coating liquid composition for the organic film material of the present invention.

The organic light-emitting device manufactured by using the coating liquid composition for an organic film material may have high luminous efficiency, low voltage driving, high heat resistance, high solvent resistance, color purity, and long lifespan compared to conventional organic light-emitting devices.

In addition, the coating liquid composition for an organic film material may be formed by any one of a spin coating process, a nozzle printing process, a coating liquid printing process, a slot coding process, a dip coating process, and a roll-to-roll process.

Hereinafter, the organic light emitting device will be described in detail.

The organic light-emitting device according to the present invention has a structure including an anode, a cathode, and an organic layer interposed between the anode and the cathode.

In addition, the organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emission auxiliary layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. In addition to that, it is possible to further form one or two intermediate layers, and a hole blocking layer or an electron blocking layer may be further formed.

In this case, as a preferred specific example of the organic light emitting device according to the present invention, the organic layer is a light emitting layer, the coating liquid composition according to the present invention is used as a host or a dopant, and the light emitting layer is additionally used as a host, a dopant It further includes, and may further include a host when used as a dopant.

Meanwhile, in the organic light emitting device, the anode includes an anode material, and the anode material is usually a material having a large work function to facilitate hole injection into the organic thin film layer. Specific examples of the cathode material include metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), and a combination of metal and oxide such as ZnO and Al or SnO2 and Sb And poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (polyehtylenedioxythiophene: PEDT), conductive polymers such as polypyrrole and polyaniline. However, it is not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) may be used as the anode.

In addition, the negative electrode includes a negative electrode material, and the negative electrode material is usually a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or alloys thereof, and LiF/Al , LiO2/Al, LiF/Ca, LiF/Al, and multi-layered materials such as BaF2/Ca, but are not limited thereto.

In addition, as the material for the hole transport layer, electron donating molecules having a small ionization potential can be used, and diamine, triamine or tetraamine derivatives mainly having triphenylamine as a basic skeleton are widely used. For example, N, N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl) -N,N'-diphenylbenzidine (a-NPD) and the like may additionally be used.

A hole injection layer (HIL) may be additionally stacked under the hole transport layer, and TCTA (4,4',4"-tri(N-carbazolyl), which is CuPc (copperphthalocyanine) or starburst amines triphenyl-amine), m-MTDATA(4,4',4"-tris-(3-methylphenylphenyl amino)triphenylamine), and the like may be used.

In addition, the electron transport layer has a function of stably transporting electrons injected from the electron injection electrode (Cathode). Materials such as quinoli-10-noate) (beryllium bis (benzoquinolin-10-olate: Bebq2), BCP, oxadiazole derivatives PBD, BMD, BND, etc. may be used, but are not limited thereto.

On the other hand, on the top of the electron transport layer, an electron injection layer (EIL) that facilitates electron injection from the cathode and ultimately improves power efficiency may be further stacked, and the electron injection layer material is also Any one commonly used in the art may be used without particular limitation.

As the material for forming the electron injection layer, any known material for forming the electron injection layer such as CsF, NaF, LiF, NaCl, Li2O, BaO, or the like may be used.

The organic light-emitting device of the present invention and a method of manufacturing the same are as follows. First, an anode 20 is formed by coating a material for an anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a conventional organic EL device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness is preferable. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used.

A hole injection layer 30 is formed on the anode 20 electrode, and then a hole transport layer 40 is formed on the hole injection layer 30.

Subsequently, the light emitting layer 50 is deposited on the hole transport layer 40 by a solution process, and the electron transport layer 60 is formed thereon, and then the electron injection layer 70 is formed and the electron injection. The organic light emitting device is completed by forming the cathode 80 electrode on the layer 70.

Meanwhile, the present invention provides an electronic device including the organic light emitting device, and the electronic device includes an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin film transistor (OTFT), Organic Light-Emitting Transistor (O-LET), Organic Solar Cell (O-SC), Organic Optical Detector, Organic Photoreceptor, Organic Electric Field-Quenching Device (O-FQD), Light-Emitting Electrochemical Cell (LEC), Organic Laser Diode (O -Laser), etc.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereto.

Intermediate compounds frequently used in the following reaction examples are indicated by adding a serial number to the number of the final product. For example, compound 1 is represented by compound [1], and the intermediate compound of the compound is represented by [1-1].

In the present specification, the number of the compound is indicated by the number of the formula shown in Table 1. For example, the compound indicated by 1 in Table 1 is indicated as compound 1.

Synthesis example 1: compound ( 1) of Produce

Preparation of intermediate compound [1-1]

Add 100g (1.61mol) of ethylene glycol to a 3L reactor, 1.2L of methylene chloride, 246.0ml (1.77mol) triethylamine, 337.9g (1.77mol) of 4-toluenesulfonyl chloride, and stir for 6 hours. After completion of the reaction, ethyl acetate, extracted with distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 292.7 g (yield 84%) of the intermediate compound [1-1] as a white solid.

Preparation of intermediate compound [1-2]

In a 3L reactor, 227.5ml (1.49mol) of 4-vinylphenyl acetate was added, 1L of dimethyl sulfoxide was added, 135.2g (3.38mol) of sodium hydroxide was added, and the temperature was raised to 60, followed by stirring for 6 hours. 292.7 g (1.35 mol) of the intermediate compound [1-1] was dissolved in 500 ml of dimethyl sulfoxide, added to the reaction mixture, and stirred at the same temperature for 18 hours. After completion of the reaction, ethyl acetate, extracted with distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 202.0 g (yield 91%) of a transparent liquid intermediate compound [1-2].

Preparation of intermediate compound [1-3]

Intermediate compound [1-2] 202.0g (1.23mol), triethylamine 187.8ml (1.35mol), 4-toluenesulfonyl chloride 258.0g (1.35mol) in the same manner as the synthesis method of intermediate compound [1-1] , Methylene chloride 1.2L was added to prepare a white solid intermediate compound [1-3] 360.3g (92% yield).

Preparation of intermediate compound [1-4]

In a 1L reactor, 9-bromoanthracene 30.0g (116.67mmol), (3,5-dimethoxyphenyl) boronic acid 31.9g (175.01mmol), tetrakis (triphenylphosphine) palladium 6.74g (5.83mmol), anhydrous 24.2 g (175.01 mmol) of potassium carbonate was added and stirred under reflux for 12 hours with 250 mL of toluene and 50 mL of purified water under a nitrogen stream. After the reaction was completed, the mixture was filtered, and the organic material was stirred with methanol and purified water, and then filtered. Then, recrystallized from toluene and acetone to prepare 27.9 g (yield 76%) of the intermediate compound [1-4] of white crystals.

Preparation of intermediate compound [1-5]

In a 1L reactor, 27.9g (88.68mmol) of the intermediate compound [1-4] was added, dissolved in 300mL of methylene chloride, and 17.4g (97.55mmol) of N-bromosuccinimide was added and stirred for 24 hours. After completion of the reaction, 300 ml of methanol was added and filtered. The filtered organic material was stirred with methanol and purified water, and then filtered. Then, it was recrystallized from acetone to prepare 30.3 g (yield 87%) of the intermediate compound [1-5] as yellow crystals.

Preparation of intermediate compound [1-6]

Intermediate compound [1-5] 30.3g (77.15mmol), (3-methoxyphenyl) boronic acid 17.6g (115.72mmol), tetrakis (triphenylphos) in the same manner as the synthesis method of intermediate compound [1-4] Pin) palladium 4.46g (3.86mmol), anhydrous potassium carbonate 16.0g (115.72mmol) was added to prepare 26.3g (yield 81%) of the intermediate compound [1-6] yellow crystals.

Preparation of intermediate compound [1-7]

26.3g (62.50mmol) of the intermediate [1-6] was added to a 2L reactor, dissolved in 600mL of methylene chloride, 23.7ml (249.99mmol) of boron tribromide was added and stirred under a nitrogen stream for 24 hours. After the reaction was completed, extraction was performed with distilled water and an aqueous sodium hydrogen carbonate solution, treated with anhydrous magnesium sulfate, filtered, and recrystallized with methylene chloride and hexane to prepare 22.9 g (yield 87%) of white crystalline intermediate compound [1-7].

Preparation of compound [1]

In a 500mL reactor, 22.9g (60.62mmol) of the intermediate compound [1-7], 67.6g (212.17mmol) of the intermediate compound [1-3], and 25.1g (181.86mmol) of anhydrous potassium carbonate were added, and 250ml of N,N-dimethylformamide. After dissolving in, the temperature was raised to 100 and stirred for 24 hours. After the reaction was completed, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, filtered, and purified by silica gel chromatography to prepare 20.3 g (yield 41%) of the target compound [1] as an off-white solid.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.76(6H, d), 7.50~7.46(6H, m), 7.18(1H, d), 7.05~7.02(9H, m), 6.73~6.72(3H,m), 6.43(1H, s), 5.72~5.71(3H, m), 5.28~5.27(3H, m), 4.66(12H, s)

m/z = 816.3

Synthesis example 2: compound ( 8) of Produce

Intermediate compound [8- 1] of Produce

In a 2L reactor, 100.0g (502.41mmol) of 1-(3-bromophenyl)ethanone, 382.3g (5024.12mmol) of propane-1,3-diol, 9.6g (50.24mmol) of copper iodide, 138.9g of anhydrous potassium carbonate (1004.82mmol), 1,10-phenanthroline 18.1g (100.48mmol) was added and stirred at 100°C for 24 hours under a nitrogen stream. After completion of the reaction, ethyl acetate, extracted with distilled water, treated with anhydrous magnesium sulfate, filtered, and purified by silica gel chromatography to prepare 30.3 g (yield 31%) of a transparent liquid intermediate compound [8-1].

Preparation of intermediate compound [8-2]

Intermediate compound [8-1] 30.3g (155.74mmol), triethylamine 23.8ml (171.32mmol), 4-toluenesulfonyl chloride 32.7g (171.32mol) in the same manner as the intermediate compound [1-1] , 200 mL of methylene chloride was added to prepare 49.4 g (91% yield) of a white solid intermediate compound [8-2].

Preparation of intermediate compound [8-3]

9,10-dibromoanthracene 30.0g(89.28mmol), (3,5-dimethoxyphenyl)boronic acid 65.0g(357.12mmol), tetrakis(3,5-dimethoxyphenyl) boronic acid 65.0g(357.12mmol) in the same way as the intermediate compound [1-4] Triphenylphosphine) palladium 5.16g (4.46mmol) and anhydrous potassium carbonate 37.0g (267.84mmol) were added to prepare 30.0g (yield 74%) of the intermediate compound [8-3] as yellow crystals.

Preparation of intermediate compound [8-4]

Intermediate compound [8-4] 30.0g (mmol), boron tribromide 31.32ml (330.39mmol), methylene chloride 700ml in the same method as the synthesis method of intermediate compound [1-7], and white crystal intermediate compound [8- 4] 25.5g (yield 98%) was prepared.

Intermediate compound [8- Of 5] Produce

Intermediate compound [8-4] 25.5g (64.75mmol), intermediate compound [8-2] 101.5g (291.39mmol), anhydrous potassium carbonate 35.8g (259.01mmol) in the same manner as the synthesis method of compound [1], N ,N-dimethylformamide 250mL was added to prepare 69.1g (yield 97%) of a yellow liquid intermediate compound [8-5].

Intermediate compound [8- 6] of Produce

Into a 3L reactor, 69.1g (62.81mmol) of the intermediate compound [8-5] was added, and 300mL of methanol and 1L of tetrahydrofuran were added and stirred. Sodium borohydride 11.9g (314.07mmol) is slowly added dropwise. Stir for 3 hours under a nitrogen atmosphere. After the reaction was completed, extraction was performed with ethyl acetate, aqueous ammonium chloride solution, distilled water, treated with anhydrous magnesium sulfate, filtered, and purified by silica gel chromatography to prepare 64.0 g (yield 92%) of a transparent liquid intermediate compound [8-6]. .

Preparation of compound [8]

In a 2L reactor, 64.0 g (57.79 mmol) of the intermediate compound [8-6] was added, dissolved in 600 mL of xylene, and 0.34 g (1.96 mmol) of p-toluenesulfonic acid was slowly added dropwise. The mixture is stirred under reflux for 24 hours while removing moisture. After the reaction was completed, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, filtered, and purified by silica gel chromatography to prepare 33.5 g (yield 56%) of the target compound [8] as a yellow liquid.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.60~7.59(4H, m), 7.49~7.48(4H, m), 7.26~7.25(8H, m), 7.05~ 6.97(8H, m), 6.73~6.72(4H, m), 6.43(2H, s), 5.72~5.71(4H, m), 5.28~5.27(4H, m), 4.39~4.28(16H, m), 2.35~2.34 (8H, m)

m/z = 1034.5

Synthesis Example 3: Preparation of compound (19)

Intermediate compound [19- 1] of Produce

Butane-1,4-diol 50.0g (554.82mmol), triethylamine 84.7ml (610.30mmol), 4-toluenesulfonyl chloride 116.4g (610.30mmol) in the same manner as the intermediate compound [1-1] , 500 mL of methylene chloride was added to prepare 105.7 g (yield 78%) of a white solid intermediate compound [19-1].

Intermediate compound [19- 2] of Produce

4-vinylphenyl acetate 72.8ml (476.05mmol), sodium hydroxide 43.3g (1081.92mol), intermediate compound [19-1] 105.7g (432.77mol), dimethyl in the same manner as the intermediate compound [1-2] 5L of sulfoxide was added to prepare 71.0g (61% yield) of a transparent liquid intermediate compound [19-2].

Intermediate compound [19- 3] of Produce

Intermediate compound [19-2] 71.0g (369.31mmol), triethylamine 56.4ml (406.24mmol), 4-toluenesulfonyl chloride 77.5g (406.24mmol) in the same manner as the synthesis method of intermediate compound [1-1] , Methylene chloride 400mL was added to prepare 78.0g (yield 92%) of a white solid intermediate compound [19-3].

Compound [ 19] of Produce

Intermediate compound [8-4] 10.0g (25.35mmol), intermediate compound [19-3] 39.5g (114.09mmol), anhydrous potassium carbonate 14.0g (101.41mmol) in the same manner as the synthesis method of compound [1], N , 150 mL of N-dimethylformamide was added to prepare 19.9 g (72% yield) of the target compound [19] as a yellow liquid.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.72~7.70(8H, m), 7.49~7.48(4H, m), 7.05~7.02(12H, m), 6.73~ 6.72(4H, m), 6.43(2H, s), 5.72~5.71(4H, m), 5.28~5.27(4H, m), 4.16~4.14(16H, m), 1.99~1.97(16H, m)

m/z = 1090.5

Synthesis example 4: compound ( Of 60) Produce

Intermediate compounds [60- 1] of Produce

1-(3-bromophenyl)ethanone 66.5mL (502.41mmol), diethylene glycol 533.2g (5024.12mmol), iodo copper 9.6g ( 50.24mmol), 1,10-phenanthroline 18.1g (100.48mmol), anhydrous potassium carbonate 138.9g (1004.82mmol) was added to prepare a transparent liquid intermediate compound [60-1] 32.7g (yield 29%).

Preparation of intermediate compound [60-2]

Intermediate compound [60-1] 32.7g (145.69mmol), triethylamine 22.2ml (160.25mmol), 4-toluenesulfonyl chloride 30.6g (160.25mmol) in the same manner as the synthesis method of intermediate compound [1-1] , 200mL of methylene chloride was added to prepare 53.5g (yield 97%) of a white solid intermediate compound [60-2].

Preparation of intermediate compound [60-3]

Intermediate compound [8-4] 10.0g (25.35mmol), intermediate compound [60-2] 43.2g (114.09mmol), anhydrous potassium carbonate 14.0g (101.41mmol), N in the same method as the synthesis method of compound [1] ,N-dimethylformamide 150mL was added to prepare 24.1g (yield 78%) of a yellow liquid intermediate compound [60-3].

Preparation of intermediate compound [60-4]

Intermediate compound [60-3] 24.1g (19.77mmol), sodium borohydride 3.74g (98.86mmol), methanol 50mL, tetrahydrofuran 350mL in the same method as the synthesis method of intermediate compound [8-6] 22.8g (yield 94%) of the solid intermediate compound [60-4] was prepared.

Preparation of compound [60]

In the same manner as the synthesis method of compound [8], 22.8g (18.58mmol) of intermediate compound [60-4], 0.11g (0.63mmol) of p-toluenesulfonic acid, and 200mL of xylene were added to the target compound as a yellow liquid [60] 9.9g (yield 46%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.69~7.67(4H, m), 7.49~7.48(4H, m), 7.26~7.25(8H, m), 7.02~ 6.97(8H, m), 6.73~6.72(4H, m), 6.43(2H, s), 5.72~5.71(4H, m), 5.28~5.27(4H, m), 4.41~4.40(16H, m), 3.89-3.87 (16H, m)

m/z = 1155.3

Synthesis Example 5: Preparation of compound (67)

Preparation of intermediate compound [67-1]

Cyclohexane-1,4-diol 30.0g (258.26mmol), triethylamine 39.4ml (284.09mmol), 4-toluenesulfonyl chloride 54.2g (284.09mmol) in the same manner as the intermediate compound [1-1] ), 300mL of methylene chloride was added to prepare 47.5g (yield 68%) of a white solid intermediate compound [67-1].

Preparation of intermediate compound [67-2]

4-vinylphenyl acetate 29.6ml (193.19mmol), sodium hydroxide 17.6g (439.08mmol), intermediate compound [67-1] 47.5g (175.63mol), dimethyl in the same way as the intermediate compound [1-2] 200 mL of sulfoxide was added to prepare 26.5 g (69% yield) of a transparent liquid intermediate compound [67-2].

Preparation of intermediate compound [67-3]

Intermediate compound [67-2] 26.5g (121.17mmol), triethylamine 13.5ml (133.29mmol), 4-toluenesulfonyl chloride 25.4g (133.29mmol) in the same manner as the synthesis method of intermediate compound [1-1] , 100 mL of methylene chloride was added to prepare 42.9 g (yield 95%) of a white solid intermediate compound [67-3].

Compound [ 67] of Produce

Intermediate compound [8-4] 10.0g (25.35mmol), intermediate compound [67-3] 42.5g (114.09mmol), anhydrous potassium carbonate 14.0g (101.41mmol) in the same manner as the synthesis method of compound [1], N , 150mL of N-dimethylformamide was added to prepare 17.0g (yield 56%) of the target compound [67] as a yellow liquid.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.72~7.70(8H, m), 7.49~7.48(4H, m), 7.04~7.02(12H, m), 6.73~ 6.72(4H, m), 6.43(2H, s), 5.72~5.71(4H, m), 5.28~5.27(4H, m), 3.74~3.72 (8H, m), 2.05~1.80 (32H, m)

m/z = 1194.6

Synthesis example 6: compound ( 69) of Produce

Intermediate compounds [69- 1] of Produce

1-(3-bromophenyl)ethanone 33.2mL (251.21mmol), 1,4-phenylenedimethanol 347.1g (2512.06mmol), iodo copper 4.78 in the same manner as the intermediate compound [8-1] g (25.12mmol), 1,10-phenanthroline 9.05g (50.24mmol), anhydrous potassium carbonate 69.4g (502.41mmol) was added to prepare 36.1g (yield 56%) of the intermediate compound [69-1] as a white solid I did.

Intermediate compounds [69- 2] of Produce

Intermediate compound [69-1] 36.1g (140.69mmol), triethylamine 21.5ml (154.76mmol), 4-toluenesulfonyl chloride 29.5g (154.76mmol) in the same manner as the synthesis method of intermediate compound [1-1] , 150 mL of methylene chloride was added to prepare 57.2 g (yield 99%) of a white solid intermediate compound [69-2].

Intermediate compounds [69- 3] of Produce

Intermediate compound [1-7] 10.0g (26.43mmol), intermediate compound [69-2] 38.0g (92.49mmol), anhydrous potassium carbonate 11.0g (79.28mmol) in the same manner as the synthesis method of compound [1], N ,N-dimethylformamide 150mL was added to prepare 20.5g (yield 71%) of a white solid intermediate compound [69-3].

Intermediate compounds [69- Of 4] Produce

Intermediate compound [69-3] 20.5g (18.76mmol), sodium borohydride 2.8g (75.04mmol), methanol 50mL, tetrahydrofuran 350mL in the same method as the intermediate compound [8-6] 18.8g (91% yield) of the solid intermediate compound [69-4] was prepared.

Compound [ 69] of Produce

In the same manner as for the synthesis of compound [8], 18.8g (15.29mmol) of intermediate compound [69-4], 0.09g (0.034mmol) of p-toluenesulfonic acid, and 200 mL of xylene were added, and the target compound as an off-white solid [69] 9.5g (61% yield) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.69(3H, t), 7.50~7.46(6H, m), 7.26~7.23(18H, m), 7.18(1H, d), 7.05~6.97(5H, m), 6.73~6.72(3H, m), 6.43(1H, s), 5.72~5.71(3H, m), 5.28~5.27(16H, m)

m/z = 1044.4

Synthesis example 7: compound ( 79) of Produce

Intermediate compounds [79- 1] of Produce

9-bromoanthracene 10.0g (38.89mmol), (2,4-dimethoxyphenyl) boronic acid 14.2g (77.78mmol), tetrakis (triphenylphosphine) in the same manner as the intermediate compound [1-4] Fin) 2.25g (1.94mmol) palladium, 8.1g (58.34mmol) anhydrous potassium carbonate, and 100ml of toluene were added to prepare 9.3g (yield 76%) of a yellow crystalline intermediate compound [79-1].

Intermediate compounds [79- 2] of Produce

In the same manner as for the synthesis of intermediate compound [1-5], 9.3g (29.55mmol) of intermediate compound [79-1], 5.8g (32.51mmol) of N-bromosuccinimide, and 150 mL of methylene chloride were added to form yellow crystals. 9.9 g (yield 85%) of the intermediate compound [79-2] was prepared.

Preparation of intermediate compound [79-3]

Intermediate compound [79-2] 9.9g (25.12mmol), (4-methoxyphenyl) boronic acid 7.6g (50.25mmol), tetrakis (triphenylphos) in the same manner as the synthesis method of intermediate compound [1-4] Fin) palladium 1.45g (1.26mmol), anhydrous potassium carbonate 5.2g (37.68mmol), toluene 100ml was added to prepare 8.6g (yield 81%) of a yellow crystalline intermediate compound [79-3].

Preparation of intermediate compound [79-4]

Intermediate compound [79-3] 8.6g (20.36mmol), boron tribromide 7.7ml (81.43mmol), methylene chloride 200ml in the same method as the synthesis method of intermediate compound [1-7], and white crystal intermediate compound [79 -4] 7.5g (yield 97%) was prepared

Preparation of compound [79]

Intermediate compound [79-4] 7.5g (19.74mmol), intermediate compound [19-3] 23.9g (69.09mmol), anhydrous potassium carbonate 8.2g (59.22mmol) in the same manner as the synthesis method of compound [1], N ,N-dimethylformamide 100mL was added to prepare 11.6g (yield 65%) of the target compound [79] as a yellow liquid.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.78~7.67(9H, m), 7.49~7.48(4H, m), 7.15(2H, d), 7.04~7.02( 6H, m), 6.74~6.71(5H, m), 5.72~5.71(3H, m), 5.28~5.27(3H, m), 4.16~4.14(12H, m), 1.99~1.97(12H, m)

m/z = 900.4

Synthesis Example 8: Preparation of compound (85)

Preparation of intermediate compound [85-1]

In the same manner as the synthesis method of the intermediate compound [1-1], hexane-2.5-diol 20.0g (169.25mmol), triethylamine 25.8ml (186.17mmol), 4-toluenesulfonyl chloride 35.5g (186.17mmol), methylene 200 mL of chloride was added to prepare 29.0 g (yield 63%) of a white solid intermediate compound [85-1].

Preparation of intermediate compound [85-2]

4-vinylphenyl acetate 18.0ml (117.29mmol), sodium hydroxide 10.7g (266.56mmol), intermediate compound [85-1] 29.0g (106.62mol), dimethyl in the same way as the intermediate compound [1-2] Into 100 mL of sulfoxide, 15.0 g (64% yield) of a transparent liquid intermediate compound [85-2] was prepared.

Preparation of intermediate compound [85-3]

Intermediate compound [85-2] 15.0g (68.22mmol), triethylamine 10.4ml (75.04mmol), 4-toluenesulfonyl chloride 14.3g (75.04mmol) in the same manner as the synthesis method of intermediate compound [1-1] , Methylene chloride 100mL was added to prepare 24.3g (yield 95%) of a white solid intermediate compound [85-3].

Preparation of intermediate compound [85-4]

Intermediate compound [1-5] 10.0g (25.43mmol), (4-methoxyphenyl) boronic acid 7.7g (50.86mmol), tetrakis (triphenylphos) in the same manner as the synthesis method of intermediate compound [1-4] Fin) palladium 1.47g (1.27mmol), anhydrous potassium carbonate 5.3g (38.14mmol), toluene 100ml was added to prepare a yellow crystal intermediate compound [85-4] 8.5g (yield 79%).

Preparation of intermediate compound [85-5]

Intermediate compound [85-4] 8.5g (20.10mmol), boron tribromide 7.6ml (80.38mmol), methylene chloride 200ml in the same method as the synthesis method of intermediate compound [1-7], and white crystal intermediate compound [85 -5] 7.5g (yield 98%) was prepared.

Preparation of compound [85]

Intermediate compound [85-5] 7.5g (19.69mmol), intermediate compound [85-3] 25.8g (68.90mmol), anhydrous potassium carbonate 8.2g (59.06mmol), N in the same manner as the synthesis method of compound [1] ,N-dimethylformamide 100mL was added to prepare 13.8g (71% yield) of the target compound [85] as a yellow liquid.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.78~7.72(8H, m), 7.49~7.48(4H, m), 7.15(2H, d), 7.04~7.02( 8H, m), 6.73~6.72(3H, m), 6.43(1H, s), 5.72~5.71(3H, m), 5.28~5.27(3H, m), 3.96~3.93(6H, m), 1.77~ 1.76(12H, m), 1.50~1.49(18H, m)

m/z = 984.5

Synthesis example 9: compound ( 92) of Produce

Preparation of intermediate compound [92-1]

1-(3-bromophenyl)ethanone 33.2mL (251.21mmol), (E)-but-2-ene-1,4-diol 221.3g ( 2512.06mmol), copper iodo 4.78g (25.12mmol), 1,10-phenanthroline 9.05g (50.24mmol), anhydrous potassium carbonate 69.4g (502.41mmol) into the white solid intermediate compound [92-1] 28.0 g (54% yield) was prepared.

Preparation of intermediate compound [92-2]

Intermediate compound [92-1] 28.0g (135.67mmol), triethylamine 20.7ml (149.23mmol), 4-toluenesulfonyl chloride 28.5g (149.23mmol) in the same manner as the synthesis method of intermediate compound [1-1] , 150mL of methylene chloride was added to prepare 47.4g (yield 97%) of a white solid intermediate compound [92-2].

Preparation of intermediate compound [92-3]

9,10-dibromoanthracene 10.0g (29.76mmol), (2,4-dimethoxyphenyl) boronic acid 21.7g (119.04mmol), tetrakis (21.7g (119.04mmol)) in the same way as the intermediate compound [1-4] Triphenylphosphine) palladium 1.72g (1.49mmol), anhydrous potassium carbonate 8.2g (59.52mmol), and 200ml of toluene were added to prepare 11.0g (yield 82%) of a yellow crystal intermediate compound [92-3].

Preparation of intermediate compound [92-4]

Intermediate compound [92-3] 11.0g (24.39mmol), boron tribromide 11.6ml (121.97mmol), methylene chloride 300ml in the same method as the synthesis method of intermediate compound [1-7], and white crystal intermediate compound [92 -4] 7.8g (81% yield) was prepared.

Preparation of intermediate compound [92-5]

Intermediate compound [92-4] 7.8g (19.75mmol), intermediate compound [92-2] 32.0g (88.88mmol), anhydrous potassium carbonate 10.9g (79.00mmol), N in the same method as the synthesis method of compound [1] , 150 mL of N-dimethylformamide was added to prepare 15.2 g (yield 67%) of a yellow liquid intermediate compound [92-5].

Preparation of intermediate compound [92-6]

Intermediate compound [92-5] 15.2g (13.23mmol), sodium borohydride 2.5g (66.15mmol), methanol 50mL, tetrahydrofuran 300mL in the same method as the synthesis method of intermediate compound [8-6] 14.4 g (yield 94%) of the solid intermediate compound [92-6] was prepared.

Preparation of compound [92]

Intermediate compound [92-6] 14.4g (12.44mmol), p-toluenesulfonic acid 0.07g (0.42mmol), and xylene 150mL were added in the same manner as the synthesis method of compound [8], and the target compound as an off-white solid [92] 8.0g (59% yield) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.67~7.63(6H, m), 7.49~7.48(4H, m), 7.30~7.27(8H, m), 7.01~ 7.00(4H, m), 6.82~6.73(8H, m), 5.78~5.77(8H, m), 5.72~5.71(4H, m), 5.28~5.27(4H, m), 4.78~4.77(16H, m) )

m/z = 1082.5

Synthesis Example 10: Preparation of compound (94)

Preparation of intermediate compound [94-1]

1-(3-bromophenyl)ethanone 33.2mL (251.21mmol), (E)-hex-3-ene-2,5-diol 291.8g ( 2512.06mmol), copper iodo 4.78g (25.12mmol), 1,10-phenanthroline 9.05g (50.24mmol), anhydrous potassium carbonate 69.4g (502.41mmol) was added to the white solid intermediate compound [94-1] 30.6 g (yield 52%) was prepared.

Preparation of intermediate compound [94-2]

Intermediate compound [94-1] 30.6g (130.61mmol), triethylamine 19.9ml (143.67mmol), 4-toluenesulfonyl chloride 27.4g (143.67mmol) in the same manner as the synthesis method of intermediate compound [1-1] , 150 mL of methylene chloride was added to prepare 48.2 g (95% yield) of a white solid intermediate compound [94-2].

Preparation of intermediate compound [94-3]

Intermediate compound [79-2] 10.0g (25.43mmol), (3-methoxyphenyl) boronic acid 7.7g (50.86mmol), tetrakis (triphenylphos) in the same manner as the synthesis method of intermediate compound [1-4] Pin) palladium 1.47g (1.27mmol), anhydrous potassium carbonate 5.3g (38.14mmol), toluene 100ml was added to prepare a yellow crystal intermediate compound [94-3] 7.7g (72% yield).

Preparation of intermediate compound [94-4]

Intermediate compound [94-3] 7.7g (18.31mmol), boron tribromide 6.9ml (73.25mmol), methylene chloride 200ml in the same method as the synthesis method of intermediate compound [1-7], and white crystal intermediate compound [94 -4] 6.4g (92% yield) was prepared.

Intermediate compounds [94- Of 5] Produce

In the same manner as the synthesis method of compound [1], intermediate compound [94-4] 6.4 g (16.86 mmol), intermediate compound [94-2] 22.9 g (59.01 mmol), anhydrous potassium carbonate 7.0 g (50.58 mmol), N ,N-dimethylformamide 100mL was added to prepare 11.1g (yield 64%) of a yellow liquid intermediate compound [95-5].

Preparation of intermediate compound [94-6]

Intermediate compound [94-5] 11.1g (14.78mmol), sodium borohydride 2.2g (59.11mmol), methanol 50mL, tetrahydrofuran 300mL in the same method as the synthesis method of intermediate compound [8-6] 13.9 g (91% yield) of a solid intermediate compound [94-6] was prepared.

Preparation of compound [94]

In the same manner as the synthesis method of compound [8], 13.9g (13.45mmol) of intermediate compound [94-6], 0.08g (0.46mmol) of p-toluenesulfonic acid, and 150 mL of xylene were added, and the target compound as an off-white solid [94] 7.1 g (54% yield) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.67~7.63(4H, m), 7.49~7.48(6H, m), 7.30~7.27(6H, m), 7.19( 1H, d), 7.09(1H, d), 7.01~7.00(3H, m), 6.76~6.73(5H, m), 5.98~5.96(6H, m), 5.71~5.70(3H, m), 5.28~ 5.27(3H, m), 4.65~4.64(6H, m), 1.59~1.58(18H, m)

m/z = 978.5

Synthesis example 11: compound ( 99) of Produce

Preparation of intermediate compound [99-1]

3-methylpentane-1,5-diol 20.0g (169.25mmol), triethylamine 25.8ml (186.17mmol), 4-toluenesulfonyl chloride 35.5g (35.5g) in the same manner as the intermediate compound [1-1] 186.17mmol), methylene chloride 200mL was added to prepare 29.0g (yield 63%) of a white solid intermediate compound [99-1].

Preparation of intermediate compound [99-2]

4-vinylphenyl acetate 18.0.0ml (117.29mmol), sodium hydroxide 10.7g (266.56mmol), intermediate compound [99-1] 29.0g (106.62mol) in the same way as the intermediate compound [1-2] Into 100 mL of dimethyl sulfoxide, 16.7 g of a transparent liquid intermediate compound [99-2] (71% yield) was prepared.

Preparation of intermediate compound [99-3]

Intermediate compound [99-2] 16.7g (75.71mmol), triethylamine 11.6ml (83.28mmol), 4-toluenesulfonyl chloride 15.9g (83.28mmol) in the same manner as the synthesis method of intermediate compound [1-1] , Methylene chloride 100mL was added to prepare 25.8g (91% yield) of a white solid intermediate compound [99-3].

Preparation of intermediate compound [99-4]

Intermediate compound [1-5] 10.0g (25.43mmol), (2,4-dimethoxyphenyl) boronic acid 9.3g (50.86mmol), tetrakis (tree) in the same manner as the synthesis method of intermediate compound [1-4] Phenylphosphine) palladium 1.47g (1.27mmol), anhydrous potassium carbonate 5.3g (38.14mmol), toluene 100ml was added to prepare a yellow crystal intermediate compound [99-4] 9.1g (yield 79%).

Preparation of intermediate compound [99-5]

Intermediate compound [99-4] 9.1g (20.09mmol), boron tribromide 9.5ml (100.44mmol), methylene chloride 200ml in the same method as the synthesis method of intermediate compound [1-7] and white crystal intermediate compound [99] -5] 7.6g (yield 96%) was prepared.

Preparation of compound [99]

Intermediate compound [99-5] 7.6g (19.29mmol), intermediate compound [99-3] 32.5g (86.82mmol), anhydrous potassium carbonate 10.7g (77.18mmol) in the same manner as the synthesis method of compound [1], N ,N-dimethylformamide 100mL was added to prepare 14.2g (yield 61%) of the target compound [99] as a yellow liquid.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.72~7.67(9H, m), 7.49~7.48(4H, m), 7.04~7.02(10H, m), 6.74~ 6.73(6H, m), 6.43(1H, s), 5.72~5.71(4H, m), 5.28~5.27(4H, m), 4.04~4.02(16H, m), 1.77~1.75(20H, m), 1.06~1.05(12H, m)

m/z = 1202.6

Synthesis Example 12: Preparation of Compound (115)

Preparation of intermediate compound [115-1]

1,1'-(5-bromo-1,3-phenylene)ethanone 30.0g (124.44mmol), heptane-1,7-diol 164.3g in the same manner as the synthesis method of the intermediate compound [8-1] (1244.40mmol), copper iodo 2.37g (12.44mmol), 1,10-phenanthroline 4.5g (24.89mmol), anhydrous potassium carbonate 34.4g (248.88mmol) into the white solid intermediate compound [115-1] 19.3g (53% yield) was prepared.

Preparation of intermediate compound [115-2]

Intermediate compound [115-1] 19.3g (65.94mmol), triethylamine 10.1ml (72.54mmol), 4-toluenesulfonyl chloride 13.8g (72.54mmol) in the same manner as the synthesis method of intermediate compound [1-1] , Methylene chloride 100mL was added to prepare 28.0g (yield 95%) of a white solid intermediate compound [115-2].

Preparation of intermediate compound [115-3]

Intermediate compound [1-7] 10.0g (35.92mmol), intermediate compound [115-2] 56.1g (125.71mmol), anhydrous potassium carbonate 14.9g (107.75mmol) in the same manner as the synthesis method of compound [1], N ,N-dimethylformamide 100mL was added to prepare 25.5g (59% yield) of a yellow liquid intermediate compound [115-3].

Preparation of intermediate compound [115-4]

Intermediate compound [115-3] 25.5g (21.19mmol), sodium borohydride 3.2g (84.76mmol), methanol 50mL, tetrahydrofuran 350mL in the same method as the intermediate compound [8-6] synthesis 23.1g (90% yield) of the solid intermediate compound [115-4] was prepared.

Preparation of compound [115]

In the same method as the synthesis method of compound [8], 23.1g (19.07mmol) of intermediate compound [115-4], 0.22g (1.30mmol) of p-toluenesulfonic acid, and 200 mL of xylene were added to the target compound of off-white d liquid [115]. ] 11.4g (54% yield) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.50~7.46(6H, m), 7.18~7.14(7H, m), 7.05~7.02(3H, m), 6.73~ 6.72(6H, m), 6.43(1H, s), 6.34~6.33(3H, m), 5.72~5.71(6H, m), 5.28~5.27(6H, m), 4.16~4.14(12H, m), 1.86~1.85(12H, m), 1.53~1.52(12H, m), 1.39~1.38(6H, m)

m/z = 1104.6

Synthesis Example 13: Preparation of compound (117)

Preparation of intermediate compound [117-1]

In a 500ml reactor, 30.0g (150.72mmol) of 1-(4-bromophenyl)ethanone, 71.0g (753.62mmol) of ethane-1,2-dithiol, and 31.3g (226.09mmol) of anhydrous potassium carbonate were added to N, Add 300 mL of N-dimethylformamide, heat to 120°C, and stir for 24 hours. After completion of the reaction, ethyl acetate, extracted with distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 12.5 g (yield 39%) of the intermediate compound [117-1] as a white solid.

Intermediate compound [117- 2] of Produce

Anthracene-9,10-diyldiboronic acid 10.0g (37.61mmol), 1-bromo-3,5-dichlorobenzene 21.2g (94.03mmol), tetrakis in the same manner as the intermediate compound [1-4] (Triphenylphosphine) palladium 2.17g (1.88mmol), anhydrous potassium carbonate 10.4g (75.23mmol), toluene 100ml was added to the intermediate compound [117-2] 10.7g of yellow crystals (yield 61%) was prepared.

Preparation of intermediate compound [117-3]

Intermediate compound [117-2] 10.7g (22.94mmol), intermediate compound [117-1] 24.4g (114.69mmol), anhydrous potassium carbonate 9.5g (68.82mmol) in the same manner as the synthesis method of intermediate compound [117-1] ), N,N-dimethylformamide 150mL was added to prepare 11.3g (yield 42%) of a white solid intermediate compound [117-3].

Preparation of intermediate compound [117-4]

Intermediate compound [117-3] 11.3g (9.64mmol), sodium borohydride 1.82g (48.18mmol), methanol 30mL, tetrahydrofuran 150mL in the same method as the synthesis method of intermediate compound [8-6] 10.2 g (90% yield) of the solid intermediate compound [117-4] was prepared.

Preparation of compound [117]

In the same manner as the synthesis method of compound [8], 10.2g (8.67mmol) of intermediate compound [117-4], 0.10g (0.59mmol) of p-toluenesulfonic acid, and 100mL of xylene were added, and the target compound was off-white [117] 4.5 g (yield 47%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.02~8.00(4H, m), 7.49~7.38 (20H, m), 7.26 (4H, s), 7.16(2H, s), 6.73~6.72(4H, m), 5.72~5.71(4H, m), 5.28~5.27(4H, m), 3.67~3.65(16H, m)

m/z = 1106.2

Examples 1 to 14

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention obtained through synthesis as a light emitting layer.

First, patterning was performed so that the light emitting area of the ITO (Indium Tin Oxide) layer on the substrate had a size of 3 mm X 3 mm, followed by cleaning.

After mounting the substrate on a spin coater, PEDOT:PSS was spin-coated on the ITO layer to a thickness of 50 nm. Thereafter, the solvent was removed by drying on a hot plate at 150° C. for 10 minutes, and the compound of the present invention obtained through synthesis was dissolved in toluene to be used as a light emitting material, and then spin-coated to a thickness of 30 nm. .

Then, after drying for 10 minutes on a hot plate at 110°C, it was crosslinked by heating at 200°C for 30 minutes.

Then, it was mounted in a vacuum chamber and the base pressure was 1X10 ^-6 torr.

Thereafter, tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed as an electron transport layer to a thickness of 40 nm, and then, LiF, an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.5 nm, Subsequently, Al was deposited to a thickness of 150 nm and used as a cathode, thereby manufacturing an organic light emitting device.

On the other hand, in the case of adding photo-crosslinking, 1 part by weight of the compound of the present invention is added, dissolved in toluene, and then spin-coated to a thickness of 30 nm, and then crosslinked by exposing 365 nm of light for 30 minutes. As the photoinitiator, 2-methyl-4,6-bis(trichloromethyl)-s-triazine (hereinafter abbreviated as MTCMT) may be used.

Experimental examples using compounds 1, 8, 19, 60, 67, 69, 79, 85, 92, 94, 99, 115, and 117 as light emitting materials according to the present invention are shown in Examples 1 to 13, respectively.

Example 14

An organic electroluminescent device was manufactured in the same manner as in Example 11, except that 1.0 part by weight of 2-methyl-4,6-bis(trichloromethyl)-s-triazine was additionally used as a photoinitiator.

Comparative Example 1

An organic electroluminescent device was manufactured in the same manner as in the Experimental Example, except that Comparative Compound 1 (ADN) was used instead of the compound according to the present invention as a light emitting material.

As described above, a forward bias DC voltage was applied to the organic light emitting devices of Examples 1 to 14 and Comparative Example 1 to measure electroluminescence (EL) characteristics with a PR-650 of Photoresearch, and the measurement result T90 life was measured through a life measurement equipment manufactured by McScience at 300 cd/m2 reference luminance, and the results are shown in Table 2 below. T90 refers to the time it takes for the luminance to decrease from initial luminance to 90%.

compound Driving voltage Efficiency (cd/A) T(90) Comparative Example 1 Comparative compound 1 7.8 2.0 7 Example 1 Compound 1 7.4 2.3 11 Example 2 Compound 8 7.3 2.3 13 Example 3 Compound 19 7.1 2.4 10 Example 4 Compound 60 6.8 2.6 14 Example 5 Compound 67 7.4 2.5 10 Example 6 Compound 69 7.1 2.4 13 Example 7 Compound 79 6.9 2.3 15 Example 8 Compound 85 7.0 2.2 14 Example 9 Compound 92 6.9 2.7 14 Example 10 Compound 94 7.0 2.5 13 Example 11 Compound 99 7.1 2.4 15 Example 12 Compound 115 7.3 2.3 13 Example 12 Compound 117 6.9 2.7 15 Example 14 Compound 99 7.1 2.4 16

As can be seen from the device data results of Table 2, it was confirmed that the compound having the structure of the crosslinking material according to the present invention exhibited lower driving voltage, higher efficiency, and higher life than Comparative Example 1.

The reason why the compound according to the present invention exhibits high efficiency and high lifetime as described above is that it forms a stable thin film and has high thermal stability due to crosslinking of the compound according to the present invention.

Accordingly, it is possible to manufacture a large-area device by coating method and crosslinking by using the light-emitting material of the present invention, and it is possible to provide an organic electroluminescent device with improved low driving voltage, high efficiency, and improved lifetime.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims are also present. It belongs to the scope of the invention.

Claims (16)

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

In the above formula (1),
The linking groups L ₁ to L ₄ are each the same or different, and are independently selected from a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C50 alkylene group. Which one is
The * means a linking group L ₁ or L ₂ and a bonding site bonding to the carbon atom of each phenyl ring bonded to the anthracene group,
The carbon atom of the aromatic ring in the anthracene group, or the carbon atom of the aromatic ring not bonded to L ₁ or L ₂ in each phenyl ring bonded to the anthracene group is bonded to hydrogen or deuterium,
The substituents Ar ₁ and A _r2 are each the same or different, and are each independently any one selected from the following Structural Formulas 1 to 3,
[Structural Formula 1]

[Structural Formula 2] [Structural Formula 3]

In the above structural formula 1,
At least one of the substituents R ₇ to R ₁₁ is a single bond connected to *** of the structural formula Q1, and when Q1 is 2 or more, each of Q1 is the same as or different from each other,
The substituents not bonded to Q1 in the substituents R ₇ to R ₁₁ are the same or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted Or any one selected from an unsubstituted C ₆ -C ₃₀ arylsilyl group, a cyano group, a nitro group, and a halogen group,
The substituent R ₁₂ is selected from hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₅ alkyl group,
In the above Structural Formulas 1 to 3, the ** means a bonding site connected to L ₃ or L ₄ ,
The linking groups R ₁ and R ₂ are the same as or different from each other, and each independently a single bond, O, S, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₂ -C ₃₀ Al Kenylene group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkylene group, a substituted or unsubstituted C ₂ -C ₃₀ alkynylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or Unsubstituted C ₂ -C ₃₀ heterocycloalkylene group, substituted or unsubstituted C ₆ -C ₅₀ arylene group, substituted or unsubstituted C ₂ -C ₅₀ heteroarylene group, substituted or unsubstituted C ₁ -C ₃₀ is an oxyalkylene group (-O-alkylene-), any one linking group selected from the following structural formula La and structural formula Lb,
[Structural Formula La] [Structural Formula Lb]

In the above structural formula La,
The substituents R ₁₇ to R ₁₈ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or Any one selected from an unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, a cyano group, and a halogen group,
The m ₁ and m2 are each the same or different, and independently of each other, are an integer of 1 to 10, but when m ₁ is 2 or more, each'in parentheses'

'Is the same or different from each other, and each in parentheses when m ₂ is 2 or more'

'Is the same or different from each other,

In the structural formula Lb,
R ₂₀ is Hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl group, a substituted or unsubstituted It is any one selected from a C ₁ -C ₃₀ alkoxy group, a cyano group, and a halogen group,
The m ₃ is an integer of 1 to 4, but when m ₃ is 2 or more, each R ₂₀ is the same or different from each other,
The m ₄ and m ₅ are each the same or different, and are independently an integer of 1 to 10, but when m ₄ is 2 or more

Each in parentheses

'Is the same or different from each other, and if m ₅ is 2 or more, each in parentheses'

'Is the same or different from each other,

The n ₁ and n ₂ are the same as or different from each other, and each independently an integer of 1 to 4, but when n ₁ is 2 or more, each'Ar ₁ -L ₃ -R ₁ -L ₁ -'in parentheses is each The same or different, and when n ₂ is 2 or more, each'Ar ₂ -L ₄ -R ₂ -L ₂ -'in parentheses is the same or different from each other,
Here, the'substituted' in the'substituted or unsubstituted' in the formula (1) is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, a C ₁ -C ₂₄ alkyl group, a C ₁ -C ₂₄ halogenation Alkyl group, C ₂ -C ₂₄ alkenyl group, C ₂ -C ₂₄ alkynyl group, C _{1 -24} heteroalkyl group, C ₆ -C ₂₄ aryl group, C ₇ -C ₂₄ arylalkyl group, C _2- C ₂₄ heteroaryl group, C ₂ -C ₂₄ heteroarylalkyl group, C ₁ -C ₂₄ alkoxy group, C ₁ -C ₂₄ alkylamino group, C ₆ -C ₂₄ arylamino group, C ₁ -C ₂₄ It means substituted with one or more substituents selected from the group consisting of a hetero arylamino group, a C ₁ -C ₂₄ alkylsilyl group, a C ₆ -C ₂₄ arylsilyl group, and a C ₆ -C ₂₄ aryloxy group. The method of claim 1,
The linking groups L ₁ and L ₂ are the same as or different from each other, and each independently a single bond or an oxygen atom (O). The method of claim 1,
The linking groups L ₃ and L ₄ are the same as or different from each other, and each independently a single bond or an oxygen atom (O). The method of claim 1,
The R ₁ and R ₂ are the same as or different from each other, and each independently a single bond, an oxygen atom (O), a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₂ -C ₃₀ Alkenylene group, substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, substituted or unsubstituted C ₆ -C ₅₀ arylene group, substituted or unsubstituted C ₂ -C ₅₀ heteroarylene group, the structural formula A compound characterized in that it is any one linking group selected from Lb. The method of claim 1,
Each of Ar ₁ and Ar ₂ is the [Structure 1]. The method of claim 1,
A compound, characterized in that only one or two of R ₇ to R ₁₁ in Structural Formula 1 is a single bond bonded to the substituent Q1. The method of claim 1,
The linking groups L ₁ , L _2, L ₃ and L ₄ are each an oxygen atom (O) or a single bond. The method of claim 1,
Wherein n ₁ and n ₂ are the same as or different from each other, and each independently a compound, characterized in that 1 or 2. The method of claim 1,
The compound represented by the formula (1) is a condensed cyclic compound represented by any one of the following [1] to [120].

A coating liquid composition for an organic film material containing at least one or more compounds according to any one of claims 1 to 9. The method of claim 10,
The coating liquid composition for an organic film material further comprises at least one of a photoinitiator, a pigment, and a dye. First electrode,
A second electrode facing the first electrode; And
An organic light-emitting device comprising; an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the coating liquid composition for an organic film material according to claim 10. The method of claim 12,
The organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emission auxiliary layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. Organic light-emitting device characterized by. The method of claim 12,
The organic light-emitting device, characterized in that the coating liquid composition for the organic film material is formed by any one of a spin coating process, a nozzle printing process, a coating liquid printing process, a slot coding process, a dip coating process, and a roll-to-roll process. The method of claim 13,
The organic layer is a light emitting layer,
The coating liquid composition is used as a host or dopant,
The light-emitting layer further includes a dopant when used as a host, and further includes a host when used as a dopant. An electronic device comprising the organic light emitting device according to any one of claims 12 to 15.