KR20190017274A - 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 chemical formula 1 and a coating solution composition including the same. More specifically, the coating solution composition for an organic film material enables a solution process and realizes device properties related to light emitting efficiency, low-voltage operations, high heat resistance, color purity, and long service life.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound for an organic electroluminescent device and a coating liquid composition for an organic film material containing the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to a novel compound for an organic electroluminescent device and a coating liquid composition for an organic film material comprising the same. More particularly, the present invention relates to a coating solution composition for organic electroluminescent devices, , High solvent resistance, color purity and long life, and a coating liquid composition for an organic film material containing the same.

An organic light emitting phenomenon is a phenomenon that converts electric energy into light energy by using an organic material. 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 an organic material, electrons and holes are transmitted from a cathode and an anode, respectively, And the organic electroluminescence in which the energy generated in this case is released into light is used.

That is, the organic light emitting device has a structure in which a thin film is sandwiched between two electrodes and can emit light. Organic light emitting devices are classified into a vacuum deposition type and a solution process type according to how an organic thin film is formed.

Vacuum deposition is a process suitable for low-molecular materials with low molecular weight. When material is heated at a high vacuum of 10 ^-6 torr or less, the material is gasified and dispersed in the chamber, and condensed on a substrate with a relatively low temperature to form a thin film .

The vacuum evaporation method is the most widely used method in the current enterprise because it can easily realize high lifetime and excellent efficiency characteristics of the device. However, when the organic light emitting device is manufactured by vacuum deposition, the amount of material used for forming the pixel pattern is condensed in the mask , The material utilization efficiency is as low as about 10% since it is smaller than the amount of the material impinged on the inner wall of the chamber.

In addition, the exponential increase in equipment operation cost due to the increase of the substrate size required for the increase of the production amount and the production unit cost is a problem in lowering the production cost, and there is a possibility of the resolution degradation due to the mask deflection due to the large- There was a problem.

On the other hand, a solution process method can be used for both a low-molecular-weight material and a high-molecular-weight polymer material. Typical methods of the solution process include inkjet printing and spin coating.

A solution process is a method of forming a thin film by dissolving a material in a solvent by ink-jetting. When the ink-jet printing method is used, the efficiency of material utilization can be maximized. Since a fine pattern can be formed without using a mask, The advantage is that it can be utilized.

However, in the solution process without cross-linking, there is a problem that when the upper film is formed, the lower film is eroded due to the solvent used, thereby damaging the lower film. Therefore, the characteristics of the device are lowered and the process yield is lowered. Cross-linking is essential to prevent erosion of the underlying film. In addition, a compound capable of forming a crosslinking, which has a high solubility in an organic solvent before crosslinking formation and a low solubility in an organic solvent after crosslinking, should be used.

As a related art, Korean Patent Registration No. 10-1105242 (Jan. 13, 2012) relates to a blue light emitting compound which can be subjected to a solution process, and includes a picolinic acid or picolinic acid-ene-oxide derivative as an auxiliary ligand, Korean Patent Laid-Open Publication No. 10-2015-0105201 (2015.09.16) discloses a novel organic luminescent compound, and discloses a carbazole-based organic compound.

However, in spite of the prior art including the above-mentioned prior arts, stable and efficient materials for organic light emitting devices which can still be subjected to a solution process have not been sufficiently developed, and thus there is a continuing need for the development of new materials.

Korean Registered Patent No. 10-1105242 (Jan. 13, 2012) Korean Patent Laid-Open Publication No. 10-2015-0105201 (2015.09.16)

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide a novel organic compound for an organic light emitting device which can be used in a solution process.

The present invention also provides a coating solution composition for an organic light emitting device in an organic light emitting diode, which is excellent in solubility in an organic solvent when used in an organic light emitting device, And to provide an organic light emitting device including the same, which can realize device characteristics such as efficiency, low voltage driving, high heat resistance, high solvent resistance, color purity and long life.

To this end, the present invention provides a compound represented by the following formula (1).

[Chemical Formula (1)

In the above formula (1)

A is a linking group represented by any one of the following formulas (A1), (A2), (A3) and (A4)

[Formula A1] [Formula A2] [Formula A3]

(A4)

The linking groups L ¹ , L ² , L ³ and L ⁴ are the same or different and each independently represents a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1- Lt; / RTI > alkylene group, < RTI ID = 0.0 &

At least one of Ar ¹ and Ar ² is any one selected from the following Structural Formulas 1 to 3,

[Structural formula 1]

[Structural formula 2] [Structural formula 3]

In Formula 1, at least one of R11 to R15 is a single bond connected to ** of Formula Q1, and when Q1 is 2 or more, each Q1 is the same or different from each other,

A substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C6-C50 aryl group, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, Substituted or unsubstituted C1-C30 heteroaryl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C1-C30 alkylthio group, substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, a cyano group, a nitro group, and a halogen group Lt;

R16 is hydrogen, deuterium, a substituted or unsubstituted C1-C5 alkyl group,

In Formulas 1 to 3, * is a single bond connected to L ³ or L ⁴ ,

In the case where the Ar ¹ or Ar ² other than one selected from the structural formula 1 to formula 3, wherein Ar ¹ or Ar ² is selected from hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted C6-C60 aryl group, a O A substituted or unsubstituted C2-C60 heteroaryl group containing at least one hetero atom selected from N, S, Si and P, a substituted or unsubstituted C3-C60 aliphatic ring and a substituted or unsubstituted C6-C60 A substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2- A substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, -L'-N (Ra) (Rb), a carboxyl group, -O-Si (R _{') 3, R'O-Si (} R'')(R''') 2 -, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C2-C30 alkenyloxy group ring of the group, a silane group , Thread Acid group, a substituted or unsubstituted aryl alkoxy group unsubstituted C7-C60, a substituted or unsubstituted C8-C60 arylalkenyl group, a substituted or unsubstituted any one selected from an alkoxycarbonyl group of C2-C60,

L 'is any one selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group,

Wherein Ra and Rb are the same or different and each independently represents a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C20 heteroatom containing at least one heteroatom selected from O, N, S, Si and P A heteroaryl group having 1 to 6 carbon atoms,

Substituted or unsubstituted C6-C20 aryl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1- Or an unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C8-C20 arylalkenyl group, a substituted or unsubstituted C7-C20 arylalkoxy group, or a substituted or unsubstituted C2-C20 alkoxycarbonyl group Lt; / RTI >

R ¹ and R ² are the same or different and each independently represents a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C50 alkylene group, A substituted or unsubstituted C7-C60 arylalkylene group, a linking group selected from the following structural formulas A and B,

[Structural Formula A] [Structural Formula B]

In Formulas A and B,

X is any one of O, S, N-R3 and CR4R5,

R 3 to R 5 are the same or different from each other and each independently represents a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, Or an unsubstituted C7-C24 arylalkyl group.

The present invention also provides a coating liquid composition for an organic film material, which comprises at least one or more of the above compounds.

The present invention also provides a liquid crystal display comprising 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.

The present invention also provides an electronic device including the organic light emitting device.

The coating liquid composition for an organic film material containing a compound represented by the formula (1) according to the present invention has a high solubility in an organic solvent and can be subjected to a solution process, and has high solvent resistance in the case of the organic film produced.

In addition, the organic light emitting device manufactured using the coating solution composition for an organic film material can have higher luminous efficiency, low voltage driving, high heat resistance, color purity, and long life time characteristics than the organic light emitting device manufactured by the conventional solution process.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

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 one of ordinary skill in the art to which this invention belongs. In general, the nomenclature used herein is well known and commonly used in the art.

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

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

[Chemical Formula (1)

In the above formula (1)

A is a linking group represented by any one of the following formulas (A1), (A2), (A3) and (A4)

[Formula A1] [Formula A2] [Formula A3]

(A4)

The linking groups L ¹ , L ² , L ³ and L ⁴ are the same or different and each independently represents a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1- Lt; / RTI > alkylene group, < RTI ID = 0.0 &

At least one of Ar ¹ and Ar ² is any one selected from the following Structural Formulas 1 to 3,

[Structural formula 1]

[Structural formula 2] [Structural formula 3]

In Formula 1, at least one of R11 to R15 is a single bond connected to ** of Formula Q1, and when Q1 is 2 or more, each Q1 is the same or different from each other,

A substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C6-C50 aryl group, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, Substituted or unsubstituted C1-C30 heteroaryl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C1-C30 alkylthio group, substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, a cyano group, a nitro group, and a halogen group Lt;

R16 is hydrogen, deuterium, a substituted or unsubstituted C1-C5 alkyl group,

In Formulas 1 to 3, * is a single bond connected to L ³ or L ⁴ ,

In the case where the Ar ¹ or Ar ² other than one selected from the structural formula 1 to formula 3, wherein Ar ¹ or Ar ² is selected from hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted C6-C60 aryl group, a O A substituted or unsubstituted C2-C60 heteroaryl group containing at least one hetero atom selected from N, S, Si and P, a substituted or unsubstituted C3-C60 aliphatic ring and a substituted or unsubstituted C6-C60 A substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2- A substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, -L'-N (Ra) (Rb), a carboxyl group, -O-Si (R _{') 3, R'O-Si (} R'')(R''') 2 -, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C2-C30 alkenyloxy group ring of the group, a silane group , Thread Acid group, a substituted or unsubstituted aryl alkoxy group unsubstituted C7-C60, a substituted or unsubstituted C8-C60 arylalkenyl group, a substituted or unsubstituted any one selected from an alkoxycarbonyl group of C2-C60,

L 'is any one selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group,

Wherein Ra and Rb are the same or different and each independently represents a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C20 heteroatom containing at least one heteroatom selected from O, N, S, Si and P A heteroaryl group having 1 to 6 carbon atoms,

Substituted or unsubstituted C6-C20 aryl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1- Or an unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C8-C20 arylalkenyl group, a substituted or unsubstituted C7-C20 arylalkoxy group, or a substituted or unsubstituted C2-C20 alkoxycarbonyl group Lt; / RTI >

R ¹ and R ² are the same or different and each independently represents a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C50 alkylene group, A substituted or unsubstituted C7-C60 arylalkylene group, a linking group selected from the following structural formulas A and B,

[Structural Formula A] [Structural Formula B]

In Formulas A and B,

X is any one of O, S, N-R3 and CR4R5,

R 3 to R 5 are the same or different from each other and each independently represents a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, Or an unsubstituted C7-C24 arylalkyl group,

Here, the 'substitution' in the 'substituted or unsubstituted' in the above formula (1) is a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, A C2-C24 heteroaryl group, a C2-C24 heteroaryl group, a C6-C24 aryl group, a C7-C24 arylalkyl group, a C2-C24 heteroaryl group, C24 aryloxy group, C1-C24 alkoxy group, C1-C24 alkylamino group, C6-C24 arylamino group, C1-C24 heteroarylamino group, C1-C24 alkylsilyl group, C6-C24 arylsilyl group, C6-C24 aryl An alkoxy group and an oxy group.

On the other hand, in consideration of the range of the alkyl or aryl group in the "substituted or unsubstituted C1-C30 alkyl group" or "substituted or unsubstituted C6-C50 aryl group" in the present invention, The carbon number of the C30 alkyl group and the C6-C50 aryl group means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety, respectively, when it is considered that the substituent does not take the substituted moiety into consideration. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to a C6 aryl group substituted with a butyl group of C4.

The aryl group which is a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to 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, An aromatic group such as a pyridyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle, a crycenyl, a naphthacenyl, a fluoranthene and the like, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH (R), -N (R ') (R''),R' and R "are independently from each other C ₁ -C ₁₀ C24 alkyl group, C1-C24 halogenated alkyl group, C2-C24 alkyl group, in this case, "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 arylalkyl group, C2-C24 heteroaryl group or C2- 4 < / RTI > heteroarylalkyl groups.

The heteroaryl group which is a substituent group used in the compound of the present invention is a compound wherein the aromatic ring in the aryl group contains 1,2 or 3 hetero atoms selected from N, O, P, Si, S, Ge, Se and Te, Means a C2-C24 aromatic system, which rings can be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

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 and hexyl. The hydrogen atoms of the above hydrogen atoms can be substituted with the same substituents as those in the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, 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 used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , And dimethylpurylsilyl. At least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

In the meantime, the characteristics of the compound represented by the formula (1) according to the present invention will be described in more detail. The compound represented by the formula (1) Wherein at least one of Ar1 and Ar2 has a structure in which -R1-L3-Ar1 'and -L2-R2-L4-Ar2' are bonded to each other, It is designed to be capable of addition reaction in a solution process by having one substituent.

In one embodiment, at least one of the linking groups L3 and L4 may each be an oxygen atom.

In one embodiment, A may be an anthracenyl group represented by the formula (A1), a pyrenyl group represented by the formula (A2), or a phenanthrenyl group represented by the formula (A3).

In one embodiment, the substituents R 1 and R 2 may be the same or different and each independently selected from a single bond, an oxygen atom, and a substituted or unsubstituted C6-C18 arylene group.

In one embodiment, both of Ar1 and Ar2 may be any one of Structural Formulas 1 to 3 above.

In one embodiment, only one or two of R11 to R15 in the structural formula 1 may be a single bond bonded to the substituent Q1.

Specific examples of the compound represented by the formula (1) in the present invention may be represented by any one of the compounds [1] to [123] described in the following Table 1, but the present invention is not limited thereto.

Meanwhile, the present invention provides a coating liquid composition for an organic film material, which comprises at least one compound represented by the above formula (1).

The coating liquid 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 chemical formula (1) and has high solvent resistance when an organic film is formed in the organic light emitting device And may be suitable for solution processes.

The coating composition for an organic film material may be a solution or suspension containing a solvent, and the solvent may be an anisole, a dimethyl anisole, a xylene, an o-xylene, an m-xylene, But are not limited to, tetrahydrofuran, tetrahydrofuran, methylene benzoate, dioxane, terahydrofuran, methyltetrahydrofuran, tetrahydropyrane, tetralin, veratrol, chlorobenzene, N-methylpyrrolidone, And a combination of these.

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

Examples of the photoinitiator include ketones, keto acetals, thioguanthones, phosphine oxides, anthraquinones, trichloromethyl triazine and oxime esters. Specific examples of such photo initiators include phenyl biphenyl ketone , Thioxanthone, isopropylthioxanthone, diethylthioxanthone, benzophenone, 1-benzyl-1-dimethylamino-1- (4-morpholino-benzoyl) propane, 1-hydroxy- Benzoyl propane, ethyl anthraquinone, 4-benzoyl-4-methyldiphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoyl propane, Butylbenzoyl trichloromethane, 4-phenoxybenzoyl dichloromethane, diphenyl-2,4,6-trimethylbenzoylphosphine oxide, methyl benzoylformate (Trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2-naphthyl-4,6-bis (trichloromethyl) (2-methylbenzoyl) -9H-carbazol-3-yl] -ethanone-1- (O-acetyloxime) Benzoyl) -1H-benzoyl) -9H-carbazol-3-yl] ethanone and 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] can do.

In addition, the pigment and the 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 conventionally used carbon black dispersion, but is not limited thereto.

According to another aspect of the present invention, there is provided a plasma display panel comprising 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 comprises the coating liquid composition for the organic film material of the present invention.

The organic light emitting device manufactured using the coating liquid composition for an organic film material may have higher luminous efficiency, lower voltage driving, higher heat resistance, higher solvent resistance, color purity, and longer life characteristics than conventional organic light emitting devices.

Also, 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 coding 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.

The organic layer includes at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, an electron injecting layer, In addition to this, an intermediate layer of one layer or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

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

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

In addition, the negative electrode includes a negative electrode material, and the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium and the like, , LiO 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but the present invention is not limited thereto.

As the hole transport layer material, an electron donor molecule having a low ionization potential can be used, and diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is widely used. For example, N, (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'- -N, N'-diphenylbenzidine (a-NPD), and the like.

A HIL (Hole Injecting Layer) may be additionally deposited on the lower portion of the hole transport layer. Alternatively, CuPc (copperphthalocyanine) or 4,4 ', 4 "-tri (N-carbazolyl) triphenyl-amine, m-MTDATA (4,4 ', 4 "-tris- (3-methylphenylphenylamino) triphenylamine).

The electron transport layer functions to stably transport electrons injected from an electron injection electrode. The electron transport layer is a quinoline derivative, tris (8-quinolinolato) aluminum (Alq3), TAZ, BAlq, beryllium bis But are not limited to, materials such as beryllium bis (benzoquinolin-10-olate: Bebq2), BCP, oxadiazole derivatives PBD, BMD, BND and the like.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. And can be used without any particular limitation as long as it is commonly used in the art.

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

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form a cathode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) or the like which is transparent and excellent in conductivity is used.

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

Then, the electron injection layer 70 is formed after the electron transport layer 60 is formed by laminating the luminous layer 50 on the hole transport layer 40, the condensed ring compound according to the present invention by a solution process, An organic light emitting device is completed by forming a cathode (80) electrode on the electron injection layer (70).

The present invention provides an electronic device including the organic light emitting device, wherein the electronic device includes an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (OTFT) (O-LET), an organic photovoltaic cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), a luminescent electrochemical cell (LEC) - laser).

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

In the following reaction examples, the intermediate compounds are indicated by adding the serial number to the final product number. For example, Compound 1 is represented by the compound [1], and the intermediate compound of the above compound is represented by [1-1] or the like.

In the present specification, the numbers of the compounds are represented by the numbers of the formulas shown in Table 1 above. For example, compounds designated 1 in Table 1 are designated Compound 1.

Synthetic example  1: Compound ( 2) of  Produce

The intermediate compound [2- 1]  Produce

Into a 500 mL reactor were added 30.0 g (89.28 mmol) of 9,10-dibromoanthracene, 36.5 g (269.84 mmol) of 1- (3-hydroxyphenyl) ethanone, 1.7 g (8.93 mmol) 3.2 g (17.86 mmol) of phenanthroline and 37.0 g (267.84 mmol) of anhydrous potassium carbonate were placed, 200 ml of N, N-dimethylformamide was added, and the mixture was stirred under reflux for 24 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, and then separated and purified by silica gel chromatography to obtain 17.0 g (yield 32%) of an intermediate compound [2-1] as a off-white solid.

The intermediate compound [2- 2]  Produce

A 1 L reactor was charged with 17.0 g (38.07 mmol) of the intermediate compound [2-1], 50 mL of methanol and 400 mL of tetrahydrofuran were added and stirred. 7.2 g (190.37 mmol) of sodium borohydride is slowly added dropwise. And stirred for 1 hour in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, ammonium chloride aqueous solution, distilled water, and subjected to anhydrous magnesium sulfate filtration and separation and purification by silica gel chromatography to obtain 14.9 g (yield: 87%) of an intermediate compound [2-2] .

The compound [ 2]  Produce

14.9 g (33.07 mmol) of the intermediate compound [2-2] was added to a 500-mL reactor and 150 mL of dimethyl sulfoxide was added thereto and stirred. 13.5 g (99.22 mmol) of zinc chloride and 7.6 mL (99.22 mmol) of trifluoroacetic acid are slowly added dropwise, and the mixture is heated to 120 DEG C and stirred for 48 hours. After completion of the reaction, ethyl acetate, sodium bicarbonate aqueous solution, extracted with distilled water, treated with anhydrous magnesium sulfate, and separated and purified by silica gel chromatography to obtain 5.1 g (yield: 37%) of the desired compound [2] as an off-white solid.

(2H, d), 7.53-7.22 (6H, m), 7.18-7.12 (4H, m), 6.73-6.72 (2H, , < / RTI > m), 5.71 (2H, d), 5.28

m / z = 414.1

Synthetic example  2: Compound ( 8) of  Produce

The intermediate compound [8- 1]  Produce

(89.28 mmol) of 9,10-dibromoanthracene, 32.6 g (214.27 mmol) of (3-methoxyphenyl) boronic acid, 1.03 g (0.89 mmol) of tetrakis (triphenylphosphine) palladium, 18.5 g (133.92 mmol) of anhydrous potassium carbonate was added, and the mixture was refluxed and stirred for 12 hours with 200 mL of toluene and 50 mL of purified water under a nitrogen stream. After completion of the reaction, the reaction mixture was filtered, and the organic matter was stirred with methanol and purified water, followed by filtration. Thereafter, recrystallization from toluene and acetone yielded 22.3 g (yield: 64%) of intermediate compound [8-1] as a white crystal.

The intermediate compound [8- 2]  Produce

22.2 g (56.85 mmol) of the intermediate compound [8-1] and 29.4 g (341.13 g) of pyridine hydrochloride were placed in a 500 mL reactor, and the mixture was stirred under reflux in a nitrogen stream. After completion of the reaction, purified water was added, followed by stirring and filtration. Thereafter, the mixture was stirred with acetone and purified water, and then filtered to obtain 19.4 g (yield: 94%) of an intermediate compound [8-2] as an off-white crystal.

The intermediate compound [8- 3]  Produce

(50.49 mmol) of intermediate compound [8-2], 26.7 mL (201.98 mmol) of 1- (3-bromophenyl) ethanone, 0.96 g (5.05 mmol) of iodopaline, 1.82 g (10.10 mmol) of anthroline and 20.9 g (151.48 mmol) of anhydrous potassium carbonate were added, and 250 ml of N, N-dimethylformamide was added thereto, followed by stirring under reflux for 24 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, distilled water, treated with anhydrous magnesium sulfate, and then recrystallized with methylene chloride, hexane and acetone to obtain 23.8 g (yield 79%) of an intermediate compound [8-3] as a off-white solid.

The intermediate compound [8- 4]  Produce

23.8 g (39.75 mmol) of intermediate compound [8-3], 100 mL of methanol, 600 mL of tetrahydrofuran, and 7.5 g (198.77 mmol) of sodium borohydride were charged in the same manner as in the synthesis of intermediate compound [ 20.4 g (yield 85%) of a solid intermediate compound [8-4] was prepared.

The compound [ 8] of  Produce

(33.85 mmol) of intermediate compound [8-4], 300 mL of dimethyl sulfoxide, 13.8 g (101.54 mmol) of zinc chloride, and 7.8 mL (101.54 mmol) of triplelacetic acid in the same manner as in the synthesis of compound [ ) To obtain 4.6 g (yield: 24%) of the desired compound [8] as a off-white solid.

(1H, m), 7.18-7.12 (6H, m), 6.73-6.72 (2H, d) , < / RTI > m), 5.71 (2H, d), 5.28

m / z = 566.2

Synthetic example  3: Compound ( 67)  Produce

The intermediate compound [67- 1]  Produce

In a 1 L reactor, 30.0 g (89.28 mmol) of 9,10-dibromoanthracene and 18.5 g (133.92 mmol) of anhydrous potassium carbonate were added, 300 mL of ethylene glycol was added under a nitrogen stream, and the mixture was heated to 120 ° C and stirred for 48 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, sodium bicarbonate aqueous solution, distilled water, and subjected to anhydrous magnesium sulfate treatment and separation and purification by silica gel chromatography to obtain 10.1 g (yield: 47%) of an intermediate compound [67-1] Respectively.

The compound [ 67]  Produce

(37.48 mmol) of intermediate compound [67-1], 20.6 g (112.44 mmol) of 1-bromo-4-vinylbenzene and 4.2 g (74.96 mmol) of potassium hydroxide were placed in a 500 mL reactor, And the mixture was stirred under reflux for 48 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, sodium bicarbonate aqueous solution, distilled water, anhydrous magnesium sulfate, and then separated and purified by silica gel chromatography to obtain 9.2 g (yield: 42%) of the desired compound as an off-white solid.

(4H, m), 7.76-7.74 (4H, m), 7.53-7.42 (4H, m), 7.04-7.03 (4H, m), 6.73-6.69 (6H, m), 5.71 (2H, d), 5.28 (2H, d)

m / z = 474.2

Synthetic example  4: Compound ( 74)  Produce

The intermediate compound [74- 1]  Produce

(83.32 mmol) of 1,6-dibromophenylene, 31.4 g (199.98 mmol) of (4-methoxyphenyl) boronic acid, 10 g of tetrakis (Yield: 85%) was obtained by adding 4.81 g (4.17 mmol) of palladium, 17.3 g (124.99 mmol) of anhydrous potassium carbonate, 200 mL of toluene and 50 mL of purified water.

The intermediate compound [74- 2]  Produce

29.4 g (70.83 mmol) of the intermediate compound [74-1] and 98.2 g (850.01 mmol) of pyridine hydrochloride were charged in the same manner as in the synthesis of intermediate compound [8-2] g (yield 69%).

The intermediate compound [74- 3]  Produce

(48.88 mmol) of intermediate compound [74-2], 25.9 mL (195.53 mmol) of 1- (3-bromophenyl) ethanone, 0.93 g of iodopropane [74-3] was obtained as a off-white solid by the same procedure as described in Example 1, except that 1.8 g (9.78 mmol) of 1,10-phenanthroline, 20.3 g (146.65 mmol) of anhydrous potassium carbonate and 250 ml of N, N- (Yield: 76%).

The intermediate compound [74- 4]  Produce

23.1 g (37.14 mmol) of the intermediate compound [74-3], 100 mL of methanol, 700 mL of tetrahydrofuran and 7.0 g (185.72 mmol) of sodium borohydride were charged in the same manner as in the synthesis of intermediate compound [2-2] 18.2 g (yield 78%) of a solid intermediate compound [74-4] was prepared.

The compound [ 74]  Produce

18.2 g (28.98 mmol) of the intermediate compound [74-4], 300 mL of dimethyl sulfoxide, 11.8 g (86.93 mmol) of zinc chloride, 6.7 mL (86.93 mmol) of triplelacetic acid in the same manner as in the synthesis of the compound [ ) To obtain 1.9 g (yield: 11%) of the desired compound as an off-white solid [74].

(4H, m), 7.86-7.76 (10H, m), 7.42 (2H, d), 7.30-7.28 (4H, m), 7.18-7.12 m), 6.73-6.72 (2H, m), 5.71 (2H, d), 5.28

m / z = 590.2

Synthetic example  5: Compound ( 79)  Produce

The intermediate compound [79- 1]  Produce

(83.32 mmol) of 1,6-dibromopyrene, 17.3 g (127.99 mmol) of anhydrous potassium carbonate and 300 mL of ethylene glycol were charged in the same manner as in the synthesis of the compound [67] 79-1] (yield: 35%).

The compound [ 79]  Produce

(29.15 mmol) of intermediate compound [79-1], 16.0 g (87.46 mmol) of 1-bromo-4-vinylbenzene and 3.3 g (58.31 mmol) of potassium hydroxide in the same manner as in the synthesis of compound [ ) To obtain 6.1 g (yield: 42%) of the desired compound [79] as a off-white solid.

(2H, d), 7.26-7.25 (4H, m), 7.69 (2H, d) 6.97 (2H, d), 6.79-6.73 (6H, m), 5.71 (2H, d), 5.28

m / z = 498.2

Synthetic example  6: Compound ( 89)  Produce

The intermediate compound [89- 1]  Produce

(77.70 mmol) of 6,12-dibromochrocycene, 16.1 g (116.56 mmol) of anhydrous potassium carbonate and 300 mL of ethylene glycol were charged in the same manner as in the synthesis of the compound [67] to obtain the intermediate compound [89 -1] (yield 37%).

The intermediate compound [ 89]  Produce

(28.75 mmol) of intermediate compound [89-1], 15.8 g (86.25 mmol) of 1-bromo-4-vinylbenzene and 3.2 g (57.50 mmol) of potassium hydroxide in the same manner as in the synthesis of compound [ ) To obtain 5.7 g (yield: 38%) of the desired compound as an off-white solid [89].

(2H, d), 7.98-7.92 (6H, m), 7.72-7.71 (4H, m), 7.04-7.03 (4H, m ), 6.79-6.73 (6H, m), 5.71 (2H, d), 5.28

m / z = 524.2

Synthetic example  7: Compound ( 95)  Produce

The intermediate compound [95- 1]  Produce

In the same manner as in the synthesis of intermediate compound [8-1], 30.0 g (116.67 mmol) of 9-bromophenanthrene, 21.3 g (140.01 mmol) of (4-methoxyphenyl) boronic acid, 26.9 g (yield 81%) of white crystalline intermediate compound [95-1] was obtained by adding 6.74 g (5.83 mmol) of palladium, 24.2 g (175.01 mmol) of anhydrous potassium carbonate, 250 mL of toluene and 50 mL of purified water.

The intermediate compound [95- 2]  Produce

28.9 g (94.50 mmol) of the intermediate compound [95-1] and 131.0 g (1133.95 mmol) of pyridine hydrochloride were charged in the same manner as in the synthesis of the intermediate compound [8-2] g (yield 75%).

The intermediate compound [95- 3]  Produce

(71.03 mmol) of intermediate compound [95-2], 28.3 g (142.05 mmol) of 1- (4-bromophenyl) ethanone, 1.35 g of iodopropane [95-3] was obtained as an off-white solid by the same procedure as in Example 1, except that 2.5 g (14.21 mmol) of 1,10-phenanthroline, 29.5 g (213.08 mmol) of anhydrous potassium carbonate and 300 ml of N, N- (Yield: 72%).

The intermediate compound [95- 4]  Produce

(51.15 mmol) of intermediate compound [95-3], 100 mL of methanol, 500 mL of tetrahydrofuran, and 9.7 g (255.75 mmol) of sodium borohydride were charged in the same manner as in the synthesis of intermediate compound [2-2] 16.6 g (83% yield) of a solid intermediate compound [95-4] was prepared.

The compound [ 95]  Produce

(42.46 mmol) of intermediate compound [95-4], 200 mL of dimethyl sulfoxide, 17.36 g (127.38 mmol) of zinc chloride and 9.8 mL (127.38 mmol) of trifluoroacetic acid in the same manner as in the synthesis of compound [ ) To obtain 3.3 g (yield 21%) of the desired compound [95] as a off-white solid.

(2H, d), 8.03-7.79 (9H, m), 7.20-7.15 (4H, m), 6.73 ), 5.71 (1 H, d), 5.28 (1 H, d)

m / z = 372.5

Example  1 to Example  7

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

First, the ITO (Indium Tin Oxide) layer was patterned to have a light emitting area of 3 mm x 3 mm on the substrate, and then cleaned.

The substrate was mounted on a spin coater, and PEDOT: PSS was spin-coated on the ITO layer to a thickness of 50 nm. Thereafter, the solution was dried on a hot plate at 150 ° C for 10 minutes to remove the solvent. The compound of the present invention obtained by the synthesis was dissolved in toluene for use as a light emitting material, and then spin-coated to a thickness of 30 nm .

Then, it was dried on a hot plate at 110 DEG C for 10 minutes, and then heated at 200 DEG C for 30 minutes to crosslink.

It was then mounted in a vacuum chamber with a base pressure of 1 × 10 ^-6 torr.

 Thereafter, tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was formed to a thickness of 40 nm as an electron transporting layer, LiF as an alkali metal metal to be an electron injecting layer was deposited to a thickness of 0.5 nm, Subsequently, Al was deposited to a thickness of 150 nm and used as a cathode to produce an organic electroluminescent device.

On the other hand, when photocrosslinking is added, 1 part by weight of the compound of the present invention is added to the compound of the present invention, and the resulting mixture is dissolved in toluene. The mixture is then spin-coated to a thickness of 30 nm and exposed to light of 365 nm 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 2, 8, 67, 74, 79, 89 and 95 according to the present invention as luminescent materials are shown in Examples 1 to 7, respectively.

Example  8

The organic electroluminescent device was fabricated in the same manner as in Example 1 except that 1.0 part by weight of 2-methyl-4,6-bis (trichloromethyl) -s-triazine was used as a photoinitiator.

Comparative Example  One

An organic electroluminescent device was fabricated in the same manner as in Experimental Example except for using the above-mentioned Comparative Compound 1 (ADN) instead of the compound according to the present invention as a luminescent material.

As described above, the electroluminescence (EL) characteristics of the organic luminescent devices of Examples 1 to 8 and Comparative Example 1 were measured with a photoresearch PR-650 by applying a forward bias DC voltage. / m < 2 > standard brightness was measured by a life measuring device manufactured by Mac Science Inc., and the results are shown in Table 2 below. T90 means the time required for the luminance to be reduced to 90% from the initial luminance.

compound Driving voltage Efficiency (cd / A) T (90) Comparative Example 1 Comparative compound 1 7.8 2.0 7 Example 1 Compound 2 7.1 2.5 10 Example 2 Compound 8 6.5 2.6 12 Example 3 Compound 67 7.2 2.5 14 Example 4 Compound 74 6.4 2.9 12 Example 5 Compound 79 7.0 3.0 11 Example 6 Compound 89 7.1 2.8 9 Example 7 Compound 95 6.9 2.7 11 Example 8 Compound 2
MTCMT
(1 part by weight addition) 7.0 2.4 10

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

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

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

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

Claims (16)

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

In the above formula (1)
A is a linking group represented by any one of the following formulas (A1), (A2), (A3) and (A4)
[Formula A1] [Formula A2] [Formula A3]

(A4)

The linking groups L ¹ , L ² , L ³ and L ⁴ are the same or different and each independently represents a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1- Lt; / RTI > alkylene group, < RTI ID = 0.0 &
At least one of Ar ¹ and Ar ² is any one selected from the following Structural Formulas 1 to 3,
[Structural formula 1]

[Structural formula 2] [Structural formula 3]

In Formula 1, at least one of R11 to R15 is a single bond connected to ** of Formula Q1, and when Q1 is 2 or more, each Q1 is the same or different from each other,
A substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C6-C50 aryl group, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, Substituted or unsubstituted C1-C30 heteroaryl group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C1-C30 alkylthio group, substituted or unsubstituted C1- A substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, a cyano group, a nitro group, and a halogen group Lt;
R16 is hydrogen, deuterium, a substituted or unsubstituted C1-C5 alkyl group,
In Formulas 1 to 3, * is a single bond connected to L ³ or L ⁴ ,
In the case where the Ar ¹ or Ar ² other than one selected from the structural formula 1 to formula 3, wherein Ar ¹ or Ar ² is selected from hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted C6-C60 aryl group, a O A substituted or unsubstituted C2-C60 heteroaryl group containing at least one hetero atom selected from N, S, Si and P, a substituted or unsubstituted C3-C60 aliphatic ring and a substituted or unsubstituted C6-C60 A substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C3-C50 cycloalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2- A substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, -L'-N (Ra) (Rb), a carboxyl group, -O-Si (R _{') 3, R'O-Si (} R'')(R''') 2 -, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C2-C30 alkenyloxy group ring of the group, a silane group , Thread Acid group, a substituted or unsubstituted aryl alkoxy group unsubstituted C7-C60, a substituted or unsubstituted C8-C60 arylalkenyl group, a substituted or unsubstituted any one selected from an alkoxycarbonyl group of C2-C60,
L 'is any one selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group,
Wherein Ra and Rb are the same or different and each independently represents a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C20 heteroatom containing at least one heteroatom selected from O, N, S, Si and P A heteroaryl group having 1 to 6 carbon atoms,
Substituted or unsubstituted C6-C20 aryl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C1- Or an unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C8-C20 arylalkenyl group, a substituted or unsubstituted C7-C20 arylalkoxy group, or a substituted or unsubstituted C2-C20 alkoxycarbonyl group Lt; / RTI >
R ¹ and R ² are the same or different and each independently represents a single bond, O, S, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C50 alkylene group, A substituted or unsubstituted C7-C60 arylalkylene group, a linking group selected from the following structural formulas A and B,
[Structural Formula A] [Structural Formula B]

In Formulas A and B,
X is any one of O, S, N-R3 and CR4R5,
R 3 to R 5 are the same or different from each other and each independently represents a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, Or an unsubstituted C7-C24 arylalkyl group,
Here, the 'substitution' in the 'substituted or unsubstituted' in the above formula (1) is a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, A C2-C24 heteroaryl group, a C2-C24 heteroaryl group, a C6-C24 aryl group, a C7-C24 arylalkyl group, a C2-C24 heteroaryl group, C24 aryloxy group, C1-C24 alkoxy group, C1-C24 alkylamino group, C6-C24 arylamino group, C1-C24 heteroarylamino group, C1-C24 alkylsilyl group, C6-C24 arylsilyl group, C6-C24 aryl An alkoxy group and an oxy group. The method according to claim 1,
And at least one of said linking groups L3 and L4 is an oxygen atom. The method according to claim 1,
Wherein A is an anthracenyl group represented by the formula (A1). The method according to claim 1,
Wherein A is a pyrenyl group represented by the formula (A2). The method according to claim 1,
Wherein A is a phenanthrenyl group represented by the formula [A3]. The method according to claim 1,
And R < 2 > are the same or different from each other, and each independently selected from a single bond, an oxygen atom and a substituted or unsubstituted C6-C18 arylene group. The method according to claim 1,
Wherein both of Ar1 and Ar2 are any one of Structural Formulas 1 to 3 above. The method according to claim 1,
Only one or two of R < 11 > to R < 15 > in the structural formula 1 is a single bond bonded to the substituent Q < 1 >. The method according to claim 1,
The compound represented by the above formula (1) is represented by any one of the following [1] to [123].

A coating liquid composition for an organic film material, which comprises at least one compound of any one of claims 1 to 7. 11. The method of claim 10,
Wherein the coating liquid composition for an organic film material further comprises at least one of a photoinitiator, a pigment, and a dye. The first electrode,
A second electrode facing the first electrode; And
And 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. 13. The method of claim 12,
The organic layer may include at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, an electron injecting layer, Wherein the organic light-emitting device comprises: 13. The method of claim 12,
Wherein the coating liquid composition for an 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 deep-coding process, and a roll-to-roll process. 14. The method of claim 13,
The organic layer is a light emitting layer,
The coating liquid composition is used as a host or a dopant,
Wherein the light emitting layer further includes a dopant when used as a host, and a host when the dopant is used as a dopant. An electronic device comprising the organic light-emitting device according to any one of claims 12 to 15.

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