KR20210104481A - 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, wherein chemical formula (1) is as described in the detailed description of the invention. The present invention has excellent solubility in organic solvents.

Description

A novel compound for an organic light emitting device and a coating solution composition for an organic film material comprising the same

The present invention relates to a novel compound for an organic light emitting device and a coating solution composition for an organic film material comprising the same, and more particularly, a solution process is possible, and when used in an organic light emitting device, high luminous efficiency, low voltage driving, high heat resistance , 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 emitting phenomenon is one example in which electric current is converted into visible light by an internal process of a specific organic molecule. The principle of organic light emitting phenomenon is as follows. When an organic material layer is placed between the anode and the cathode, when a current is applied between the two electrodes, electrons and holes are respectively injected into the organic material layer from the cathode and the anode. Electrons and holes injected into the organic layer recombine to form excitons, and the excitons fall back to the ground state and emit light. An organic light emitting device using this principle may be generally composed of a cathode, an anode, and an organic layer disposed therebetween, for example, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

That is, the organic light emitting device has a structure that is sandwiched between two electrodes in the form of a thin film on an organic material capable of emitting light.

The vacuum deposition 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 in the chamber, condensed on a relatively low temperature substrate to form a thin film. .

The vacuum deposition method is currently the most used method in companies because it is easy to realize the high lifespan and excellent efficiency characteristics of the device. , it shows a low material use efficiency of about 10% because it is less than the amount of coagulation on the inner wall of the chamber.

In addition, the exponential increase in equipment operating cost due to the increase in the substrate size required to increase production and reduce production cost is a challenge in lowering the production cost, and there is a high possibility of resolution degradation due to mask sagging due to large area. There was a problem.

On the other hand, 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 an inkjet printing method and a spin coating method.

The solution process method is a method of forming a thin film by dissolving a material in a solvent and turning it into ink. When the inkjet printing method is used, the material use efficiency can be maximized, and since a fine pattern is possible without using a mask, it is an advantageous manufacturing method for large area. It has the advantage of being able to use it.

However, since the solution process without crosslinking has a problem of eroding the lower film and damaging the lower film due to the solvent used when forming the upper film, it causes deterioration of device characteristics and lowering process yield, and when the upper film is formed Crosslinking is essential to prevent erosion of the underlying film. In addition, it is necessary to use a compound capable of forming a cross-link, which has high solubility in an organic solvent before cross-link formation and low solubility in organic solvent after cross-link is formed.

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

As a related art, Korean Patent Publication No. 10-1105242 (Jan. 13, 2012) relates to a blue light emitting compound capable of solution processing, and iridium having picolinic acid or a picolinic acid-ene-oxide derivative as an auxiliary ligand. Disclosed is a blue light-emitting compound, and Korean Patent Application Laid-Open No. 10-2015-0105201 (2015.09.16) relates to a novel organic light-emitting compound, and discloses a carbazole-based organic compound.

However, in spite of 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 been sufficiently developed.

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

Accordingly, 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 solution 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, so that a solution process is possible and high light emission An object of the present invention is to provide a coating solution composition for an organic film material capable of realizing 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)]

상기 화학식 (1)에서,

In the above formula (1),

The connecting _{groups L 1} to L ₆ are the same or different, and each independently a single bond, O, S, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, and a substituted or unsubstituted C ₁ -C ₃₀ alkyl It is one selected from among rengi,

The connecting _{groups Y 1} to Y ₃ are the same or different, and each independently a single bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a substituted or An unsubstituted, linking group having a structure of -MN-M'-, wherein M and M' are the same or different and each independently represent a substituted or unsubstituted C ₆ -C ₁₂ arylene group, wherein N is a substituted Or a _{linking group that is an unsubstituted C 1} -C ₁₅ alkylene group, a substituted or unsubstituted, and a linking group having a structure of -PQ-P'-, wherein P and P' are the same or different and each independently substituted or an unsubstituted C ₁ -C ₁₅ alkylene group, wherein Q is a substituted or unsubstituted C ₆ -C ₁₂ arylene group, a linking group, a substituted or unsubstituted C ₇ -C ₃₀ arylalkylene group, substituted or unsubstituted A _{substituted or unsubstituted C 2} -C ₃₀ alkenylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenylene group, a substituted or unsubstituted C ₂ -C ₅₀ heteroarylene group, substituted or unsubstituted C ₂ -C ₃₀ heterocycloalkylene group, substituted or unsubstituted C ₁ -C ₃₀ oxyalkylene group (-O-alkylene-), substituted or unsubstituted C ₆ -C ₃₀ of oxyarylene group (-O-arylene-), any one selected from,

The substituents R ₁ to R ₄ are the same or different, and are each independently 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, substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₆ - C ₃₀ is any one selected from an arylsilyl group, a cyano group, a nitro group, and a halogen group,

Wherein m1 and m2 are the same or different, and each independently represents an integer of 1 to 8, but when R ₃ or R ₄ is not bonded to a carbon atom of the aromatic ring in the anthracene group, it is bonded to hydrogen or deuterium,

When m1 or m2 is 2 or more, each R ₃ or R ₄ is the same as or different from each other,

Wherein n ₁ and n ₂ are the same or different, and each independently an integer of 1 to 4, when n ₁ is 2 or more, each 'Ar ₁ -L ₃ -Y ₁ -L ₁ -' are the same as or different from each other, and when n ₂ is 2 or more, each 'Ar ₂ -L ₄ -Y ₂ -L ₂ -' bonded to the phenyl group is the same as or different from each other,

When (5-n1) is 2 or more, each R1 is the same as or different from each other, and when (5-n2) is 2 or more, each R2 is the same or different from each other, and

The substituents Ar ₁ and A _r2 are the same or different from each other, and are each independently selected from the following [Structural Formula 1] to [Structural Formula 3],

[Structural Formula 1]

[Structural formula 2] [Structural formula 3]

In Structural Formula 1,

The substituents R ₇ to R ₁₁ are the same as or different from each other, and are 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 unsubstituted C ₆ - C ₃₀ Arylsilyl group, cyano group, nitro group, halogen group. Any one selected from the substituent Q1,

At least one of the substituents R ₇ to R ₁₁ is the substituent Q1, and '*' in the substituent Q1 means a bonding site bonded to an aromatic carbon atom of the phenyl group in Structural Formula 1,

When the substituent Q1 is 2 or more, each Q1 is the same as or different from each other,

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

In [Structural Formula 1] to [Structural Formula 3], '**' means a binding site connected to the _{linking group L 3} or L _{4 in Formula (1).}

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

In addition, the present invention provides 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 provides an organic light emitting device including the coating solution composition for an organic film material of the present invention.

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

The coating solution composition for an organic film material comprising the compound represented by Formula (1) according to the present invention has excellent solubility in an organic solvent, so that the 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 using the coating solution composition for an organic film material may have high luminous efficiency, low voltage driving, high heat resistance, color purity and long lifespan compared to organic light emitting devices manufactured by a conventional solution process.

Hereinafter, the present invention will be described in more detail. Unless defined otherwise, 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 those well known and commonly used in the art.

Throughout this specification, when a 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 connecting _{groups L 1} to L ₆ are the same or different, and each independently a single bond, O, S, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, and a substituted or unsubstituted C ₁ -C ₃₀ alkyl It is one selected from among rengi,

The connecting _{groups Y 1} to Y ₃ are the same or different, and each independently a single bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a substituted or An unsubstituted, linking group having a structure of -MN-M'-, wherein M and M' are the same or different and each independently represent a substituted or unsubstituted C ₆ -C ₁₂ arylene group, wherein N is a substituted Or a _{linking group that is an unsubstituted C 1} -C ₁₅ alkylene group, a substituted or unsubstituted, and a linking group having a structure of -PQ-P'-, wherein P and P' are the same or different and each independently substituted or an unsubstituted C ₁ -C ₁₅ alkylene group, wherein Q is a substituted or unsubstituted C ₆ -C ₁₂ arylene group, a linking group, a substituted or unsubstituted C ₇ -C ₃₀ arylalkylene group, substituted or unsubstituted A _{substituted or unsubstituted C 2} -C ₃₀ alkenylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenylene group, a substituted or unsubstituted C ₂ -C ₅₀ heteroarylene group, substituted or unsubstituted C ₂ -C ₃₀ heterocycloalkylene group, substituted or unsubstituted C ₁ -C ₃₀ oxyalkylene group (-O-alkylene-), substituted or unsubstituted C ₆ -C ₃₀ of oxyarylene group (-O-arylene-), any one selected from,

The substituents R ₁ to R ₄ are the same or different, and are each independently 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, substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₆ - C ₃₀ is any one selected from an arylsilyl group, a cyano group, a nitro group, and a halogen group,

Wherein m1 and m2 are the same or different, and each independently represents an integer of 1 to 8, but when R ₃ or R ₄ is not bonded to a carbon atom of the aromatic ring in the anthracene group, it is bonded to hydrogen or deuterium,

When m1 or m2 is 2 or more, each R ₃ or R ₄ is the same as or different from each other,

Wherein n ₁ and n ₂ are the same or different, and each independently an integer of 1 to 4, when n ₁ is 2 or more, each 'Ar ₁ -L ₃ -Y ₁ -L ₁ -' are the same as or different from each other, and when n ₂ is 2 or more, each 'Ar ₂ -L ₄ -Y ₂ -L ₂ -' bonded to the phenyl group is the same as or different from each other,

When (5-n1) is 2 or more, each R1 is the same as or different from each other, and when (5-n2) is 2 or more, each R2 is the same or different from each other, and

The substituents Ar ₁ and A _r2 are the same or different from each other, and are each independently selected from the following [Structural Formula 1] to [Structural Formula 3],

[Structural Formula 1]

[Structural formula 2] [Structural formula 3]

In Structural Formula 1,

The substituents R ₇ to R ₁₁ are the same as or different from each other, and are 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 unsubstituted C ₆ - C ₃₀ Arylsilyl group, cyano group, nitro group, halogen group. Any one selected from the substituent Q1,

At least one of the substituents R ₇ to R ₁₁ is the substituent Q1, and '*' in the substituent Q1 means a bonding site bonded to an aromatic carbon atom of the phenyl group in Structural Formula 1,

When the substituent Q1 is 2 or more, each Q1 is the same as or different from each other,

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

In the [Structural Formula 1] to [Structural Formula 3], the '**' means a binding site connected to the _{linking group L 3} or L _{4 in Formula (1),}

Here, 'substitution' in 'substituted or unsubstituted' in Formula (1) is deuterium, cyano group, halogen group, hydroxyl group, nitro group, C ₁ -C ₂₄ alkyl group, 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 Heteroarylamino group, C ₁ -C ₂₄ Alkylsilyl group, C ₆ -C ₂₄ Arylsilyl group, C ₆ -C _{24 It} means substituted with one or more substituents selected from the group consisting of an 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 carbon number of the C 1} -C ₃₀ alkyl group and the C ₆ -C ₅₀ aryl group is the total constituting the alkyl portion or the aryl portion when viewed as unsubstituted without considering the portion substituted with the substituent. 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, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by 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 a neighboring substituent 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, and aromatic groups such as pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., wherein at least one hydrogen atom of the aryl group is a deuterium atom, halogen Atom, hydroxyl group, nitro group, cyano group, silyl group, amino group (-NH2, -NH(R), -N(R')(R''), R' and R" are independently of each other C ₁ -C ₁₀ of an alkyl group, in this case referred to as "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C ₁ -C ₂₄ alkyl group, 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, includes 1, 2 or 3 heteroatoms selected from among N, O, P, Si, S, Ge, Se, and Te, and the remaining ring atoms are carbon Phosphorus C ₂ -C _{24 It} refers to an aromatic system that is an aryl group, and the rings may be fused to form a ring. And one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituents 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, and the like, and one of the alkyl groups The above hydrogen atoms can be substituted with the same substituents as in the case of the aryl group.

Specific examples of the alkoxy group as a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy and the like, One or more hydrogen atoms in the alkoxy group may be substituted with the same substituents 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, wherein one or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.

On the other hand, when describing the characteristics of the compound represented by Formula (1) according to the present invention in more detail, two anthracenes, which are main parts for electron and hole transport, are connected to the linking group '-L ₅ -Y ₃ -L ₆ -''Ar ₁ -L ₃ -R ₁ -L ₁ -' and 'Ar ₂ -L ₄ - Each of R ₂ -L ₂ -' is characterized by a structure in which 1 to 4 bonds are bonded, and in this case, as the polymerizable functional group, Ar ₁ and Ar ₄ may have any one substituent selected from Structural Formulas 1 to 3 By configuring, it is a technical feature that it is designed to enable addition reaction in the solution process.

That is, the compound represented by Formula (1) according to the present invention has a high molecular weight by _{linking two anthracene groups, which are electron and hole transport materials, adjacent to each other as the linking group '-L 5} -Y ₃ -L _{6 -'} The compound structure of the present invention suppressed the increase in driving voltage due to designed.

The chemical structure of the present invention according to these technical features corresponds to a novel parent nucleus structure that has not been previously reported, and in particular, the linking group '-L ₅ -Y ₃ -L ₆ -' in the formula (1) is a sulfur atom (S) Or, as a linking group containing an oxygen atom (O), an _{anthracene group is bonded to each of L 5} - and L ₆ , and when a phenyl group including a polymerizable functional group is present at both ends of each anthracene group, in the organic solvent Solubility is excellent, so solution processing is possible, and in the case of the prepared organic film, it can have high solvent resistance. Compared to the organic light emitting diode, it may have high luminous efficiency, low voltage driving, high heat resistance, color purity, and long lifespan.

As an embodiment, the linking _{groups L 1} and L ₂ in Formula (1) may be the same as or different from each other, and may each independently be any one selected from a single bond, a sulfur atom (S), and an oxygen atom (O). .

As an embodiment, the linking _{groups L 3} and L ₄ in Formula (1) may be the same as or different from each other, and may each independently be any one selected from a single bond, a sulfur atom (S), and an oxygen atom (O). .

As an embodiment, the linking _{groups L 5} and L ₆ in Formula (1) may be the same as or different from each other, and may each independently be any one selected from a single bond, a sulfur atom (S), and an oxygen atom (O). .

In one embodiment, Y ₁ to Y ₃ in Formula (1) are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, a substituted or unsubstituted A C ₆ -C ₁₈ arylene group, substituted or unsubstituted, and a linking group having a structure of -MN-M′-, wherein M and M′ are the same or different and independently of each other, substituted or unsubstituted C ₆ - A C ₁₂ arylene group, wherein N is a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, a linking group, a substituted or unsubstituted, and a linking group having a structure of -PQ-P'-, wherein the P and P' are the same or different and are each independently a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, wherein Q is a substituted or unsubstituted C ₆ -C ₁₂ arylene group, a linking group, a substituted or unsubstituted C ₇ -C ₁₈ arylalkylene group, substituted or unsubstituted C ₂ -C ₁₂ alkenylene group, substituted or unsubstituted C ₃ -C ₁₄ cycloalkylene group, substituted or unsubstituted C ₅ -C ₁₄ cyclo An alkenylene group, a substituted or unsubstituted C ₂ -C ₁₈ heteroarylene group, a substituted or unsubstituted C ₂ -C ₁₂ heterocycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₂ oxyalkylene group ( -O-alkylene-), a substituted or unsubstituted C ₆ -C ₁₈ oxyarylene group (-O-arylene-), may be any one linking group selected from, in this case Y ₃ is preferably . A substituted or unsubstituted C ₁ -C ₁₂ alkylene group, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, a substituted or unsubstituted, and a linking group having a structure of -MN-M′-, wherein M and M' is the same or different, and each independently represents a substituted or unsubstituted C ₆ -C ₁₂ arylene group, wherein N is a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, a linking group, substituted or unsubstituted, , -PQ-P'- as a linking group having a structure, wherein P and P' are the same or different and are each independently a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, wherein Q is a substituted or unsubstituted Any one connecting group selected from a linking group that is a C ₆ -C ₁₂ arylene group, a substituted or unsubstituted C ₇ -C ₁₈ arylalkylene group, and a substituted or unsubstituted C ₃ -C _{14 cycloalkylene group} have

In one embodiment, Ar ₁ and Ar ₂ in Formula (1) may be each of [Structural Formula 1].

[Structural Formula 1]

Here, the substituents R ₇ to R ₁₁ , the substituent Q1 and the substituent R ₁₂ are the same as defined above.

In addition, when each of Ar ₁ and Ar ₂ in Formula (1) is [Structural Formula 1], _{only one or two of R 7} to R ₁₁ in Structural Formula 1 may be a substituent Q1, and in this case, Structural Formula 1 When _{two of R 7} to R ₁₁ in R 7 to R 11 are substituents Q1, they are the same or different from each other.

As an embodiment, the connecting _{groups L 1} to L ₆ in Formula (1) may be the same or different from each other, and may each independently be a single bond, an oxygen atom (O), and a sulfur atom (S).

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

Meanwhile, a specific example of the compound represented by Formula (1) in the present invention may be a compound represented by any one of the following [Compound 1] to [Compound 166], but is not limited thereto.

[Compound 1] [Compound 2]

[Compound 3] [Compound 4]

[Compound 5] [Compound 6]

[Compound 7] [Compound 8]

[Compound 9] [Compound 10]

[Compound 11] [Compound 12]

[Compound 13] [Compound 14]

[Compound 15] [Compound 16]

[Compound 17] [Compound 18]

[Compound 19] [Compound 20]

[Compound 21] [Compound 22]

[Compound 23] [Compound 24]

[Compound 25] [Compound 26]

[Compound 27] [Compound 28]

[Compound 29] [Compound 30]

[Compound 31] [Compound 32]

[Compound 33] [Compound 34]

[Compound 35] [Compound 36]

[Compound 37] [Compound 38]

[Compound 39] [Compound 40]

[Compound 41] [Compound 42]

[Compound 43] [Compound 44]

[Compound 45] [Compound 46]

[Compound 47] [Compound 48]

[Compound 49] [Compound 50]

[Compound 51] [Compound 52]

[Compound 53] [Compound 54]

[Compound 55] [Compound 56]

[Compound 57] [Compound 58]

[Compound 59] [Compound 60]

[Compound 61] [Compound 62]

[Compound 63] [Compound 64]

[Compound 65] [Compound 66]

[Compound 67] [Compound 68]

[Compound 69] [Compound 70]

[Compound 71] [Compound 72]

[Compound 73] [Compound 74]

[Compound 75] [Compound 76]

[Compound 77] [Compound 78]

[Compound 79] [Compound 80]

[Compound 81] [Compound 82]

[Compound 83] [Compound 84]

[Compound 85] [Compound 86]

[Compound 87] [Compound 88]

[Compound 89] [Compound 90]

[Compound 91] [Compound 92]

[Compound 93] [Compound 94]

[Compound 95] [Compound 96]

[Compound 97] [Compound 98]

[Compound 99] [Compound 100]

[Compound 101] [Compound 102]

[Compound 103] [Compound 104]

[Compound 105] [Compound 106]

[Compound 107] [Compound 108]

[Compound 109] [Compound 110]

[Compound 111] [Compound 112]

[Compound 113] [Compound 114]

[Compound 115] [Compound 116]

[Compound 117] [Compound 118]

[Compound 119] [Compound 120]

[Compound 121] [Compound 122]

[Compound 123] [Compound 124]

[Compound 125] [Compound 126]

[Compound 127] [Compound 128]

[Compound 129] [Compound 130]

[Compound 131] [Compound 132]

[Compound 133] [Compound 134]

[Compound 135] [Compound 136]

[Compound 137] [Compound 138]

[Compound 139] [Compound 140]

[Compound 141] [Compound 142]

[Compound 143] [Compound 144]

[Compound 145] [Compound 146]

[Compound 147] [Compound 148]

[Compound 149] [Compound 150]

[Compound 151] [Compound 152]

[Compound 153] [Compound 154]

[Compound 155] [Compound 156]

[Compound 157] [Compound 158]

[Compound 159] [Compound 160]

[Compound 161] [Compound 162]

[Compound 163] [Compound 164]

[Compound 165] [Compound 166]

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

The coating solution composition for an organic film material according to the present invention has excellent 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. Therefore, it may be suitable for solution processing.

The coating solution composition for an organic film material 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. Tylene, methyl benzoate, dioxane, terahydrofuran, methyl tetrahydrofuran, tetrahydropyran, tetralin, veratrol, chlorobenzene, N-methyl pyrrolidone, N,N-dimethylformamide, dimethyl sulfoxide and one selected from the group consisting of combinations thereof.

Also, according to another embodiment of the present invention, the coating solution 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 the photoinitiator include phenylbiphenylketone. , 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 may include any one or more selected from the group.

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

In addition, the present invention is a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer provides an organic light-emitting device including the coating solution composition for an organic film material according to the present invention.

An organic light emitting device manufactured using the coating solution 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 solution composition for an organic film material may be formed by any one of a spin coating process, a nozzle printing process, a coating solution 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.

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 emitting 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 also possible to further form an intermediate layer of one or two layers, and it is also possible to further form a hole blocking layer or an electron blocking layer.

In this case, as a preferred embodiment of the organic light emitting device according to the present invention, the organic layer is an organic light emitting device, characterized in that the light emitting layer.

The coating solution composition according to the present invention is used as a host or a dopant, and the light emitting layer further includes a dopant when additionally used as a host, and may further include a host when used as a dopant.

On the other hand, in the organic light emitting device, the anode includes an anode material, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic thin film layer. Specific examples of the anode 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 conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (polyehtylenedioxythiophene: PEDT), polypyrrole, and polyaniline. However, the present invention 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 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, etc. or alloys thereof, and LiF/Al , LiO2/Al, LiF/Ca, LiF/Al, and a multilayer structure material such as BaF2/Ca, but is 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 mainly diamine, triamine or tetraamine derivatives 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 be additionally used.

A hole injection layer (HIL, Hole Injecting Layer) may be additionally stacked on the lower portion of the hole transport layer, and CuPc (copperphthalocyanine) or starburst amines TCTA (4,4',4"-tri(N-carbazolyl)) triphenyl-amine), m-MTDATA(4,4',4"-tris-(3-methylphenylphenyl amino)triphenylamine), etc. may be used.

In addition, the electron transport layer functions to stably transport electrons injected from the electron injection electrode (Cathode), and is a quinoline derivative, tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzo Materials such as beryllium bis(benzoquinolin-10-olate: Bebq2), BCP, and oxadiazole derivatives PBD, BMD, BND, etc. may be used, but the present invention is not limited thereto.

On the other hand, an electron injection layer (EIL), which functions to improve power efficiency by facilitating electron injection from the cathode, may be further laminated on the electron transport layer, and the electron injection layer material is also As long as it is conventionally used in the art, it 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, etc. may be used.

The organic light emitting device of the present invention and its manufacturing method will be described as follows. First, a material for an anode electrode is coated on the substrate 10 to form the anode 20 . 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, handling and waterproofing properties 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), etc., which are transparent and have excellent conductivity, are 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 .

Next, a light emitting layer 50 is laminated on the hole transport layer 40 by a solution process, and an electron transport layer 60 is formed thereon, an electron injection layer 70 is formed, and the electron injection An 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, wherein 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 Transistors (O-LET), Organic Solar Cells (O-SC), Organic Optical Detectors, Organic Photoreceptors, Organic Field-Quench Devices (O-FQDs), Light Emitting Electrochemical Cells (LECs), Organic Laser Diodes (O) -laser), etc.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating 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 thereby.

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 denoted as compound [1], and an intermediate compound of the compound is denoted as [1-1] or the like.

In the present specification, as the compound represented by Formula 1, a dianthracene intermediate compound is commonly used. The dianthracene intermediate compound may be prepared according to the method of the following general formula (1).

[General formula 1]

In General Formula 1, Y ₃ is the same as defined in Formula 1 in the present invention, and X represents a halogen element.

The general formula 1 is an example of synthesizing a dianthracene intermediate compound that forms the compound represented by the formula 1, and by designing the starting material to include an oxygen atom or a sulfur atom, the compound represented by the formula 1 of the present invention Intermediates for preparation can be easily prepared. The synthesis method according to the present invention is not limited to Formula 1 above, and may be performed by methods known in the art.

As an example of the general formula 1, it can be represented by the following synthesis examples A and A-1.

Synthesis Example A: Preparation of intermediate compounds (IM-2, IM-3)

Preparation of intermediate compound [IM-1]

In a 3L reactor, 13.1 g (540.60 mmol) of magnesium was put, 500 ml of anhydrous tetrahydrofuran was added, and 101.6 g (540.60 mmol) of 1,2-dibromoethane was slowly added dropwise and stirred under reflux. After confirming that the magnesium is completely dissolved, 50 g (257.43 mmol) of anthrone is slowly added dropwise and stirred under reflux for 24 hours. After completion of the reaction, 200 ml of 6N hydrochloric acid was added to ice water, the reaction product was added dropwise, and the mixture was stirred. Extracted with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 86.4 g of an intermediate compound [IM-1] as a white solid (yield 81%).

Preparation of intermediate compounds [IM-2], [IM-3]

In a 3L reactor, 86.4 g (208.52 mmol) of the intermediate compound [IM-1] was put, 700 ml of methylene chloride was added, 40.8 g (229.37 mmol) of N-bromosuccinimide was added, and the mixture was stirred for 20 hours. After completion of the reaction, extraction with distilled water, treatment with anhydrous magnesium sulfate, filtration, separation and purification by silica gel chromatography, light yellow solid intermediate compound [IM-2] 64.8g (yield 63%), [IM-3] 15.5g ( Yield 13%) was prepared.

Synthesis Example A-1: Preparation of intermediate compounds (IM-5, IM-6)

Preparation of intermediate compound [IM-4]

13.1 g (540.60 mmol) of magnesium, 94.6 g (540.60 mmol) of 1,4-bis (chloromethyl) benzene, 50 g (257.43 mmol) of anthrone, and anhydrous tetrahydro in the same manner as for the synthesis of the intermediate compound [IM-1] Into 500ml of furan to prepare a white solid intermediate compound [IM-4] 92.2g (yield 73%).

Preparation of intermediate compounds [IM-5], [IM-6]

Intermediate compound [IM-4] 92.2g (187.92mmol), N-bromosuccinimide 36.8g (206.71mmol), methylene chloride by the same method as for the synthesis of intermediate compounds [IM-2] and [IM-3] 700ml of the intermediate compound [IM-5] as a light yellow solid (yield 60%) and [IM-6] 13.4g (yield 11%) were prepared.

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

Synthesis Example 1: Preparation of compound (5)

Preparation of intermediate compound [5-1]

Put 1-(4-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,3-dibromopropane 222.4g (1101.73mmol), anhydrous potassium carbonate 45.7g (330.52mmol) in a 3L reactor, and ethyl acetate 300ml After dissolving in reflux and stirring for 24 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 42.5 g of a transparent liquid intermediate compound [5-1] (yield 75%).

Preparation of intermediate compound [5-3]

In a 1L reactor, 20.0 g (40.54 mmol) of intermediate compound [5-2], 8.9 g (48.64 mmol) of (3,5-dimethoxyphenyl) boronic acid, 2.34 g (2.03 mmol) of tetrakis (triphenylphosphine) palladium , Put 8.40 g (60.80 mmol) of anhydrous potassium carbonate, and stir under a nitrogen stream with 200 ml of toluene and 50 ml of purified water under reflux for 12 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 17.4 g of the intermediate compound [5-3] as white crystals (yield 78%).

Preparation of intermediate compound [5-4]

In a 1L reactor, 17.4 g (31.62 mmol) of the intermediate compound [5-3] was put, dissolved in 200 ml of methylene chloride, 6.2 g (34.78 mmol) of N-bromosuccinimide was added, and the mixture was stirred for 24 hours. After completion of the reaction, extraction was performed with methylene chloride and distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 16.1 g of yellow crystal intermediate compound [5-4] (yield 81%).

Preparation of intermediate compound [5-5]

In the same manner as for the synthesis of intermediate compound [5-3], 16.1 g (25.61 mmol) of intermediate compound [5-4], 4.7 g (30.73 mmol) of (3-methoxyphenyl) boronic acid, tetrakis (triphenylphos) Fin) 1.48 g (1.28 mmol) of palladium, 5.3 g (38.41 mmol) of anhydrous potassium carbonate, 200 ml of toluene, and 50 ml of purified water were added to prepare 14.5 g of the intermediate compound [5-5] as white crystals (yield 86%).

Preparation of intermediate compound [5-6]

In a 1L reactor, 14.5 g (22.02 mmol) of the intermediate compound [5-5] was put, dissolved in 600 mL of methylene chloride, 10.5 ml (27.58 mmol) of boron tribromide was added, and the mixture was stirred for 24 hours under a nitrogen stream. After completion of the reaction, extraction with distilled water and aqueous sodium hydrogen carbonate solution, treatment with anhydrous magnesium sulfate, filtration, separation and purification by silica gel chromatography, and 10.4 g (yield 77%) of the intermediate compound [5-6] as white crystals were prepared.

Preparation of intermediate compound [5-7]

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [5-6] 10.4 g (16.95 mmol), intermediate compound [5-1] 15.3 g (59.33 mmol), anhydrous potassium carbonate 7.0 g (50.86 mmol) ), and 250 mL of N,N-dimethylformamide to prepare 11.4 g (yield 59%) of the intermediate compound [5-7] as a yellow liquid.

Preparation of intermediate compound [5-8]

In a 1L reactor, 11.44 g (10.01 mmol) of the intermediate compound [5-7] was added, methanol 50 mL, and tetrahydrofuran 200 L were added and stirred. 1.9 g (50.03 mmol) of sodium borohydride is slowly added dropwise. Stirred under nitrogen atmosphere for 3 hours. After completion of the reaction, extraction with ethyl acetate, ammonium chloride aqueous solution, distilled water, treatment with anhydrous magnesium sulfate, filtration, separation and purification by silica gel chromatography, 10.4 g of a transparent liquid intermediate compound [5-8] (yield 90%) was prepared .

Preparation of compound [5]

In a 500ml reactor, 10.4g (9.00mmol) of the intermediate compound [5-8] was put, dissolved in 200mL of xylene, and then 0.12g (0.61mmol) of p-toluenesulfonic acid was slowly added dropwise. While removing moisture, the mixture was stirred under reflux for 48 hours. After completion of the reaction, extraction was performed with ethyl acetate and distilled water, treated with anhydrous magnesium sulfate, filtered, and separated and purified by silica gel chromatography to prepare 4.6 g of the target compound [5] as a yellow liquid (yield 47%).

¹ H NMR (δ ppm; CDCl3-d): 8.06-8.00 (4H, m), 7.80-7.75 (4H, m), 7.52-7.50 (6H, m), 7.31-7.26 (10H, m), 6.98 ( 1H, d), 6.85 to 6.82 (9H, m), 6.43 (3H, m), 6.23 (1H, s), 5.72 to 5.71 (3H, m), 5.28 to 5.27 (3H, m), 4.46 to 4.40 ( 4H, m), 4.39 to 4.30 (12H, m), 2.35 to 2.34 (6H, m)

m/z = 1094.5

Synthesis Example 2: Preparation of compound (11)

Preparation of intermediate compound [11-1]

By the same method as the synthesis method of the intermediate compound [5-1], 1-(4-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,3-dibromo-2-methylpropane 237.9g (1101.73mmol) ), 152.3 g (1101.73 mmol) of anhydrous potassium carbonate, and 500 ml of ethyl acetate were added to prepare 42.4 g of an intermediate compound [11-1] as a white solid (yield 71%).

Preparation of intermediate compound [11-3]

In the same manner as for the synthesis of intermediate compound [5-3], 20.0 g (34.95 mmol) of intermediate compound [11-2], 15.3 g (83.87 mmol) of (3,5-dimethoxyphenyl) boronic acid, tetrakis (tri Phenylphosphine) palladium 2.02g (1.75mmol), anhydrous potassium carbonate 12.1g (87.37mmol), toluene 200ml, purified water 50ml was put into the intermediate compound [11-3] 19.4g (yield 81%) as white crystals were prepared.

Preparation of intermediate compound [11-4]

In the same manner as for the synthesis of intermediate compound [5-6], 19.4 g (28.31 mmol) of intermediate compound [11-3], 13.4 ml (141.53 mmol) of boron tribromide, and 300 ml of methylene chloride were added, and white crystal intermediate compound [11] -4] 13.8 g (yield 77%) was prepared.

Preparation of intermediate compound [11-5]

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [11-4] 10.0 g (15.86 mmol), intermediate compound [11-1] 19.4 g (71.35 mmol), anhydrous potassium carbonate 8.8 g (63.42 mmol) ), and 200 ml of N,N-dimethylformamide to prepare 12.6 g (yield 57%) of intermediate compound [11-5] as a yellow liquid.

Preparation of intermediate compound [11-6]

In the same manner as for the synthesis of intermediate compound [5-8], 12.6 g (9.04 mmol) of intermediate compound [11-5], 1.71 g (45.20 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 11.3 g (yield 89%) of the intermediate compound [11-6] was prepared.

Preparation of compound [11]

In the same manner as in the synthesis of compound [5], 11.3 g (8.04 mmol) of intermediate compound [11-6], 0.10 g (0.55 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [11] as a yellow liquid 4.8 g (yield 45%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.06-8.00 (4H, m), 7.80-7.75 (4H, m), 7.52-7.50 (8H, m), 7.31-7.26 (8H, m), 6.84- 6.82 (12H, m), 6.53 (4H, m), 6.23 (2H, s), 5.72 to 5.71 (4H, m), 5.28 to 5.27 (4H, m), 4.46 to 4.40 (4H, m), 4.39 to 4.30 (16H, m), 2.77 (4H, m), 1.06 (12H, m)

m/z = 1326.6

Synthesis Example 3: Preparation of compound (57)

Preparation of intermediate compound [57-1]

By the same method as the synthesis method of the intermediate compound [5-1], 1-(3-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,7-dibromoheptane 284.2g (1101.73mmol), carbonic anhydride 152.3 g (1101.73 mmol) of potassium and 500 ml of ethyl acetate were added to prepare 44.9 g (yield 65%) of the intermediate compound [57-1] as a white solid.

Preparation of intermediate compound [57-2]

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [11-4] 10.0 g (15.86 mmol), intermediate compound [57-1] 22.4 g (71.35 mmol), anhydrous potassium carbonate 8.8 g (63.42 mmol) ), N,N-dimethylformamide (200ml) was added to prepare 11.9g (yield: 48%) of intermediate compound [57-2] as a yellow liquid.

Preparation of intermediate compound [57-3]

In the same manner as for the synthesis of intermediate compound [5-8], 11.9 g (7.61 mmol) of intermediate compound [57-2], 1.44 g (38.05 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 10.1 g (yield 85%) of the intermediate compound [57-3] was prepared.

Preparation of compound [57]

In the same manner as in the synthesis of compound [5], 10.1 g (6.47 mmol) of intermediate compound [57-3], 0.08 g (0.44 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [57] as a yellow liquid 4.2 g (yield 43%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.06-8.00 (4H, m), 7.80-7.75 (4H, m), 7.49-7.47 (4H, m), 7.31-7.26 (8H, m), 7.06- 7.04 (8H, m), 6.82 to 6.77 (8H, m), 6.53 (4H, m), 6.23 (2H, s), 5.72 to 5.71 (4H, m), 5.28 to 5.27 (4H, m), 4.46 to 4.40 (4H, m), 4.16 to 4.14 (16H, m), 1.86 to 1.84 (16H, m), 1.43 to 1.41 (16H, m), 1.39 (8H, m)

m/z = 1494.8

Synthesis Example 4: Preparation of compound (72)

Preparation of intermediate compound [72-1]

By the same method as the synthesis method of the intermediate compound [5-1], 1-(4-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,4-bis(chloromethyl)benzene 192.9g (1101.73mmol), 152.3 g (1101.73 mmol) of anhydrous potassium carbonate and 500 ml of ethyl acetate were added to prepare 36.9 g (yield 61%) of the intermediate compound [72-1] as a white solid.

Preparation of intermediate compound [72-2]

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [11-4] 10.0 g (15.86 mmol), intermediate compound [72-1] 19.6 g (71.35 mmol), anhydrous potassium carbonate 8.8 g (63.42 mmol) ), and 200 ml of N,N-dimethylformamide to prepare 11.3 g (yield 45%) of intermediate compound [72-2] as a yellow liquid.

Preparation of intermediate compound [72-3]

In the same manner as for the synthesis of intermediate compound [5-8], 11.3 g (7.13 mmol) of intermediate compound [72-2], 1.35 g (35.67 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 10.3 g (yield 91%) of the intermediate compound [72-3] was prepared.

Preparation of compound [72]

In the same manner as in the synthesis of compound [5], 10.3 g (6.50 mmol) of intermediate compound [72-3], 0.08 g (0.44 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [72] as a yellow liquid 4.6 g (yield 47%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.06-8.00 (4H, m), 7.80-7.75 (4H, m), 7.49-7.47 (8H, m), 7.31-7.26 (8H, m), 7.06- 7.04 (16H, m), 6.84 to 6.82 (12H, m), 6.53 (4H, m), 6.23 (2H, s), 5.72 to 5.71 (4H, m), 5.28 to 5.26 (20H, m), 4.46 to 4.40 (4H, m)

m/z = 1494.8

Synthesis Example 5: Preparation of compound (81)

Preparation of intermediate compound [81-1]

By the same method as the synthesis method of the intermediate compound [5-1], 1-(3-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,4-dibromobutane 237.9g (1101.73mmol), carbonic anhydride Potassium 152.3g (1101.73mmol) and ethyl acetate 500ml were put into the intermediate compound [81-1] 44.2g (yield 84%) as a white solid was prepared.

Preparation of intermediate compound [81-2]

In the same manner as for the synthesis of intermediate compound [5-3], 20.0 g (40.54 mmol) of intermediate compound [5-2], 8.9 g (48.64 mmol) of (2,4-dimethoxyphenyl) boronic acid, tetrakis (tri Phenylphosphine) palladium 2.34 g (2.03 mmol), anhydrous potassium carbonate 8.4 g (60.80 mmol), toluene 200 ml, and purified water 50 ml were put, and 18.5 g of the intermediate compound [81-2] as white crystals (yield 83%) was prepared.

Preparation of intermediate compound [81-3]

In the same manner as for the synthesis of intermediate compound [5-4], 18.5 g (33.65 mmol) of intermediate compound [81-2], 6.6 g (37.02 mmol) of N-bromosuccinimide, and 200 ml of methylene chloride were added, and yellow crystals 18.0 g (yield 85%) of the intermediate compound [81-3] was prepared.

Preparation of intermediate compound [81-4]

In the same manner as for the synthesis of the intermediate compound [5-3], 18.0 g (28.61 mmol) of the intermediate compound [81-3], 5.2 g (34.33 mmol) of (3-methoxyphenyl) boronic acid, tetrakis (triphenylphos) Fin) 1.65 g (1.43 mmol) of palladium, 5.9 g (42.91 mmol) of anhydrous potassium carbonate, 200 ml of toluene, and 50 ml of purified water were added to prepare 16.2 g (yield 86%) of the intermediate compound [81-4] as white crystals.

Preparation of intermediate compound [81-5]

In the same manner as for the synthesis of intermediate compound [5-6], 16.2 g (24.61 mmol) of intermediate compound [81-4], 9.3 ml (98.42 mmol) of boron tribromide, and 300 ml of methylene chloride were added, and white crystal intermediate compound [81] -5] 11.2 g (yield 74%) was prepared.

Preparation of intermediate compound [81-6]

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [81-5] 10.0 g (16.27 mmol), intermediate compound [81-1] 15.4 g (56.94 mmol), anhydrous potassium carbonate 6.8 g (48.81 mmol) ), and 200 ml of N,N-dimethylformamide to prepare 8.9 g (yield 46%) of intermediate compound [81-6] as a yellow liquid.

Preparation of intermediate compound [81-7]

In the same manner as for the synthesis of the intermediate compound [5-8], 8.9 g (7.48 mmol) of the intermediate compound [81-6], 1.13 g (29.93 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 8.5 g (yield 95%) of the intermediate compound [81-7] was prepared.

Preparation of compound [81]

In the same manner as in the synthesis of compound [5], 8.5 g (7.11 mmol) of intermediate compound [81-7], 0.09 g (0.48 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [81] as a yellow liquid 3.6 g (yield 45%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.31 to 8.30 (2H, m), 7.80 to 7.75 (6H, m), 7.49 to 7.47 (4H, m), 7.32 to 7.20 (10H, m), 7.06 to 7.04 (6H, m), 6.98 (1H, d), 6.85 (1H, d), 6.77 to 6.76 (3H, m), 6.53 to 6.51 (5H, m), 5.72 to 5.71 (3H, m), 5.28 to 5.26 (3H, m), 4.46 to 4.40 (4H, m), 4.16 to 4.14 (12H, m), 1.99 (12H, m)

m/z = 1136.5

Synthesis Example 6: Preparation of compound (101)

Preparation of intermediate compound [101-1]

In the same method as the synthesis method of the intermediate compound [5-1], 1-(3-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,6-dibromohexane 268.8g (1101.73mmol), carbonic anhydride Potassium 152.3g (1101.73mmol) and 500ml of ethyl acetate were added to prepare 47.5g (yield 72%) of the intermediate compound [101-1] as a white solid.

Preparation of intermediate compound [101-2]

In the same manner as for the synthesis of intermediate compound [5-3], 20.0 g (34.95 mmol) of intermediate compound [11-2], 15.3 g (83.87 mmol) of (2,4-dimethoxyphenyl) boronic acid, tetrakis (tri Phenylphosphine) palladium 2.02g (1.75mmol), anhydrous potassium carbonate 9.7g (69.89mmol), toluene 200ml, purified water 50ml was put into white crystal intermediate compound [101-2] 19.0g (yield 79%) was prepared.

Preparation of intermediate compound [101-3]

In the same manner as for the synthesis of intermediate compound [5-6], 19.0 g (27.61 mmol) of intermediate compound [101-2], 13.1 ml (138.03 mmol) of boron tribromide, and 300 ml of methylene chloride were added, and white crystals of intermediate compound [101] -3] 12.5 g (yield 72%) was prepared.

Preparation of intermediate compound [101-4]

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [101-3] 10.0 g (15.86 mmol), intermediate compound [103-1] 19.4 g (71.35 mmol), anhydrous potassium carbonate 8.8 g (63.42 mmol) ), and 200 ml of N,N-dimethylformamide to prepare 12.6 g (yield 53%) of the intermediate compound [101-4] as a yellow liquid.

Preparation of intermediate compound [101-5]

In the same manner as for the synthesis of the intermediate compound [5-8], 12.6 g (8.41 mmol) of the intermediate compound [101-4], 1.6 g (42.03 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 11.6 g (yield 91%) of the intermediate compound [101-5] was prepared.

Preparation of compound [101]

In the same manner as in the synthesis of compound [5], 11.6 g (7.65 mmol) of intermediate compound [101-5], 0.10 g (0.52 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [101] as a yellow liquid 4.7 g (yield 43%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.06-8.04 (4H, m), 7.80-7.75 (4H, m), 7.49-7.47 (6H, m), 7.31-7.30 (8H, m), 7.06- 7.04 (8H, m), 6.77 to 6.76 (4H, m), 6.54 to 6.51 (8H, m), 5.72 to 5.71 (4H, m), 5.28 to 5.26 (4H, m), 4.46 to 4.40 (4H, m) ), 4.16 to 4.14 (16H, m), 1.86 to 1.85 (16H, m), 1.53 to 1.52 (16H, m)

m/z = 1438.7

Synthesis Example 7: Preparation of compound (127)

Preparation of intermediate compound [127-1]

In the same method as the synthesis method of the intermediate compound [5-1], 1-(4-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,4-dibromobutane 237.9g (1101.73mmol), carbonic anhydride 152.3 g (1101.73 mmol) of potassium and 500 ml of ethyl acetate were added to prepare 45.4 g (yield 76%) of the intermediate compound [127-1] as a white solid.

Preparation of intermediate compound [127-3]

In the same manner as for the synthesis of intermediate compound [5-3], 20.0 g (33.31 mmol) of intermediate compound [127-2], 14.6 g (79.95 mmol) of (3,5-dimethoxyphenyl) boronic acid, tetrakis (tri Phenylphosphine) palladium 1.92g (1.67mmol), anhydrous potassium carbonate 9.2g (66.63mmol), toluene 200ml, purified water 50ml was put into white crystal intermediate compound [127-3] 17.9g (yield 75%) was prepared.

Preparation of intermediate compound [127-4]

In the same manner as for the synthesis of intermediate compound [5-6], 17.9 g (24.98 mmol) of intermediate compound [127-3], 11.9 ml (124.92 mmol) of boron tribromide, and 300 ml of methylene chloride were added, and white crystals of the intermediate compound [127] -4] 12.2 g (yield 74%) was prepared.

Preparation of intermediate compound [127-5]

In the same manner as for the synthesis of intermediate compound [5-1], 10.0 g (15.18 mmol) of intermediate compound [127-4], 18.5 g (68.31 mmol) of intermediate compound [127-1], 8.4 g (60.72 mmol) of anhydrous potassium carbonate ), and 200 ml of N,N-dimethylformamide to prepare 11.0 g (yield 51%) of the intermediate compound [127-5] as a yellow liquid.

Preparation of intermediate compound [127-6]

In the same manner as for the synthesis of intermediate compound [5-8], 11.0 g (7.74 mmol) of intermediate compound [127-5], 1.46 g (38.71 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 9.8 g (yield 89%) of the intermediate compound [127-6] was prepared.

Preparation of compound [127]

In the same manner as in the synthesis of compound [5], 9.8 g (6.89 mmol) of intermediate compound [127-6], 0.09 g (0.47 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [127] as a yellow liquid 4.3 g (yield 46%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.06~8.04(4H, m), 7.80~7.75(4H, m), 7.52~7.60 (8H, m), 7.31~7.30(8H, m), 6.84~ 6.82(12H, m), 6.54~6.51(4H, m), 6.23(2H, s), 5.72~5.71(4H, m), 5.28~5.26(4H, m), 4.16~4.14(20H, m), 1.99 to 1.97 (20H, m)

m/z = 1354.6

Synthesis Example 8: Preparation of compound (149)

intermediate compound [149- 1] of Produce

In the same method as the synthesis method of the intermediate compound [5-1], 1-(3-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,5-dibromopentane 253.3g (1101.73mmol), carbonic anhydride 152.3 g (1101.73 mmol) of potassium and 500 ml of ethyl acetate were added to prepare 45.7 g (yield 77%) of the intermediate compound [149-1] as a white solid.

intermediate compound [149- 3] of Produce

In the same manner as for the synthesis of intermediate compound [5-3], 20.0 g (32.19 mmol) of intermediate compound [149-2], 14.1 g (77.25 mmol) of (3,5-dimethoxyphenyl) boronic acid, tetrakis (tri Phenylphosphine) palladium 1.86g (1.61mmol), anhydrous potassium carbonate 8.9g (64.38mmol), toluene 200ml, purified water 50ml was put into white crystals of intermediate compound [149-3] 17.1g (yield 72%) was prepared.

intermediate compound [149- 4] of Produce

In the same manner as for the synthesis of intermediate compound [5-6], 17.1 g (23.17 mmol) of intermediate compound [149-3], 11.0 ml (115.86 mmol) of boron tribromide, and 300 ml of methylene chloride were added, and white crystals of the intermediate compound [149] -4] 11.2 g (yield 71%) was prepared.

intermediate compound [149- 5] of Produce

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [149-4] 10.0 g (14.71 mmol), intermediate compound [149-1] 17.8 g (66.20 mmol), anhydrous potassium carbonate 8.1 g (58.85 mmol) ), and 200 ml of N,N-dimethylformamide to prepare 10.4 g (yield 47%) of intermediate compound [149-5] as a yellow liquid.

Preparation of intermediate compound [149-6]

In the same manner as for the synthesis of intermediate compound [5-8], 10.4 g (6.91 mmol) of intermediate compound [149-5], 1.31 g (34.57 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 9.2 g (yield 88%) of the intermediate compound [149-6] was prepared.

Preparation of compound [149]

In the same manner as in the synthesis of compound [5], 9.2 g (6.09 mmol) of intermediate compound [149-6], 0.08 g (0.41 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [149] as a yellow liquid 4.4 g (yield 50%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.01 to 8.00 (4H, m), 7.81 to 7.80 (4H, m), 7.49 to 7.48 (4H, m), 7.31 to 7.30 (8H, m), 7.19 ( 2H, m), 7.06 to 7.05 (8H, m), 6.82 to 6.77 (8H, m), 6.54 to 6.51 (5H, m), 6.23 (2H, s), 5.72 to 5.71 (4H, m), 5.28 to 5.26 (4H, m), 4.16 to 4.14 (16H, m), 1.86 to 1.84 (16H, m), 1.70 to 1.68 (8H, m)

m/z = 1431.7

Synthesis Example 9: Preparation of compound (163)

Preparation of intermediate compound [163-1]

In the same method as the synthesis method of the intermediate compound [5-1], 1-(3-hydroxyphenyl)ethanone 30.0g (220.35mmol), 1,4-dibromocyclohexane 266.6g (1101.73mmol), anhydrous 152.3 g (1101.73 mmol) of potassium carbonate and 500 ml of ethyl acetate were added to prepare 40.6 g (yield 62%) of the intermediate compound [163-1] as a white solid.

Preparation of intermediate compound [163-3]

In the same manner as for the synthesis of intermediate compound [5-3], 20.0 g (28.72 mmol) of intermediate compound [163-2], 12.5 g (68.92 mmol) of (3,5-dimethoxyphenyl) boronic acid, tetrakis (tri Phenylphosphine) palladium 1.66g (1.44mmol), anhydrous potassium carbonate 7.9g (57.44mmol), toluene 200ml, purified water 50ml was put into white crystals of intermediate compound [163-3] 18.4g (yield 79%) was prepared.

Preparation of intermediate compound [163-4]

In the same manner as for the synthesis of intermediate compound [5-6], 18.4 g (22.69 mmol) of intermediate compound [163-3], 10.8 ml (113.45 mmol) of boron tribromide, and 300 ml of methylene chloride were added, and white crystals of intermediate compound [163] -4] 12.7 g (yield 74%) was prepared.

Preparation of intermediate compound [163-5]

In the same manner as for the synthesis of intermediate compound [5-1], intermediate compound [163-4] 10.0 g (13.25 mmol), intermediate compound [163-1] 17.7 g (59.62 mmol), anhydrous potassium carbonate 7.3 g (52.99 mmol) ), and 200 ml of N,N-dimethylformamide to prepare 11.0 g (yield 51%) of intermediate compound [163-5] as a yellow liquid.

Preparation of intermediate compound [163-6]

In the same manner as for the synthesis of intermediate compound [5-8], 11.0 g (6.76 mmol) of intermediate compound [163-5], 1.28 g (33.80 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 9.8 g (yield 89%) of the intermediate compound [163-6] was prepared.

Preparation of compound [163]

In the same manner as in the synthesis of compound [5], 9.8 g (6.01 mmol) of intermediate compound [163-6], 0.08 g (0.41 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [163] as a yellow liquid 4.2 g (yield 45%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.01 to 8.00 (4H, m), 7.81 to 7.80 (4H, m), 7.49 to 7.48 (4H, m), 7.41 to 7.30 (12H, m), 7.14 to 7.06 (12H, m), 7.06 to 6.77 (8H, m), 6.54 to 6.51 (4H, m), 6.23 (2H, s), 5.72 to 5.71 (4H, m), 5.28 to 5.26 (4H, m), 3.54 to 3.53 (8H, m), 1.90 to 1.78 (32H, m)

m/z = 1554.7

Synthesis example 10: compound ( 165)'s Produce

intermediate compound [165- 1] of Produce

In the same method as the synthesis method of the intermediate compound [5-1], 1-(3-bromophenyl)ethanone 30.0g (151.54mmol), pentane-1,5-dithiol 103.3g (757.69mmol), carbonic anhydride Potassium 104.7g (757.69mmol), N,N- dimethylformamide 500ml into the intermediate compound [165-1] 20.6g (yield 57%) was prepared as a white solid.

Preparation of intermediate compound [165-3]

In the same manner as for the synthesis of intermediate compound [5-3], 20.0 g (36.75 mmol) of intermediate compound [165-2], 19.9 g (88.20 mmol) of 1-bromo-3,5-dichlorobenzene, tetrakis (tri Phenylphosphine) palladium 2.12 g (1.84 mmol), anhydrous potassium carbonate 10.2 g (73.50 mmol), toluene 200 ml, and purified water 50 ml were put, and 14.0 g of the intermediate compound [165-3] as white crystals (yield 51%) was prepared.

Preparation of intermediate compound [165-4]

In the same manner as for the synthesis of intermediate compound [5-1], 10.0 g (13.39 mmol) of intermediate compound [165-3], 14.4 g (60.28 mmol) of intermediate compound [165-1], 7.4 g (53.58 mmol) of anhydrous potassium carbonate ), and 200 ml of N,N-dimethylformamide to prepare 8.9 g (yield 41%) of the intermediate compound [165-4] as a yellow liquid.

intermediate compound [165- 5] of Produce

In the same manner as for the synthesis of intermediate compound [5-8], 8.9 g (5.49 mmol) of intermediate compound [165-4], 1.04 g (27.47 mmol) of sodium borohydride, 50 ml of methanol, and 200 ml of tetrahydrofuran were put into a transparent liquid. 8.2 g (yield 92%) of the intermediate compound [165-5] was prepared.

Preparation of compound [165]

In the same manner as in the synthesis of compound [5], 8.2 g (5.05 mmol) of intermediate compound [165-5], 0.07 g (0.34 mmol) of p-toluenesulfonic acid, and 200 ml of xylene were added, and the target compound [165] as a yellow liquid was added. 4.1 g (yield 52%) was prepared.

¹ H NMR (δ ppm; CDCl3-d): 8.06-8.05 (4H, m), 7.81-7.80 (4H, m), 7.31-7.17 (20H, m), 7.06-7.05 (4H, m), 6.96 ( 2H, s), 6.79 to 6.78 (4H, m), 6.73 to 6.72 (4H, m), 5.72 to 5.71 (4H, m), 5.28 to 5.26 (4H, m), 4.16 to 4.14 (4H, m), 3.04 to 3.00 (16H, m), 1.86 to 1.65 (30H, m)

m/z = 1552.5

Examples 1 to 10

An organic light emitting diode was manufactured according to a conventional method using the compound according to the present invention obtained through Synthesis Examples 1 to 10 as a light emitting layer.

First, the substrate was patterned so that the light emitting area of the indium tin oxide (ITO) layer had a size of 3 mm x 3 mm, and then washed.

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

Then, the spin-coated substrate was dried on a hot plate at 80° C. for 10 minutes, cross-linked by heating at 200° C. for 30 minutes, mounted in a vacuum chamber, and the base pressure was 1 x 10 ^-6 torr. made to be

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

Experimental examples in which compounds 5, 11, 57, 72, 81, 101, 127, 149, 163 and 165 according to the present invention were used as light emitting layer materials were shown in Examples 1 to 10, respectively.

Example 11

Meanwhile, in the present invention, in order to evaluate the experimental results according to light crosslinking, immediately before spin coating the composition of the light emitting layer, the total weight of the light emitting layer composition including the compound of the present invention is 100 and 1 part by weight is additionally added to toluene. After melting, spin-coating is performed to a thickness of 30 nm, and then cross-linked by exposing it to light of 365 nm for 30 minutes. In this case, the photoinitiator used here was 2-methyl-4,6-bis(trichloromethyl)-s-triazine (hereinafter abbreviated as MTCMT), and an organic electroluminescent device was fabricated in the same manner as in Example 7 above. did.

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 as a light emitting material instead of the compound according to the present invention.

ADN

Experimental Example 1

As described above, a forward bias DC voltage was applied to the organic light emitting devices manufactured according to Examples 1 to 11 and Comparative Example 1, and electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, As a result of the measurement, the T90 lifetime was measured using a lifetime measuring device manufactured by McScience at 300 cd/m2 standard luminance, and the results are shown in Table 2 below. In this case, T90 denotes a time required for the luminance to decrease from the initial luminance to 90%.

compound drive voltage Efficiency (cd/A) T(90) Comparative Example 1 Comparative compound 1 7.8 2.0 7 Example 1 compound 5 7.1 2.5 12 Example 2 compound 11 7.2 2.5 13 Example 3 compound 57 7.4 2.4 15 Example 4 compound 72 6.9 2.7 14 Example 5 compound 81 7.1 2.5 15 Example 6 compound 101 7.3 2.6 14 Example 7 compound 127 6.9 2.6 17 Example 8 compound 149 6.5 2.8 12 Example 9 compound 163 7.1 2.5 15 Example 10 compound 165 7.0 2.7 13 Example 11 compound 127 6.9 3.0 20

From the device data results in Table 2, the organic electroluminescent device including the compound having the structure of the cross-linking material according to the present invention exhibits lower driving voltage, higher efficiency and higher lifespan than the case of using Comparative Compound 1 according to Comparative Example 1. was confirmed to be indicated.

On the other hand, as can be seen from Examples 7 and 11, which compared thermal cross-linking and optical cross-linking, it is shown that light cross-linking is more stable than thermal cross-linking and has less effect on materials, which is It can be seen that the thin film is formed better than the thermal crosslinking, which shows high efficiency and high lifespan.

Therefore, when the compound represented by Formula 1 of the present invention is applied to an organic light emitting device, it is possible to manufacture a large-area device by crosslinking, and to provide an organic electroluminescent device with improved low driving voltage, high efficiency and lifespan can do.

Although 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 as defined in the following claims are also presented. 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 connecting _{groups L 1} to L ₆ are the same or different, and each independently a single bond, O, S, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, and a substituted or unsubstituted C ₁ -C ₃₀ alkyl It is one selected from among rengi,
The connecting _{groups Y 1} to Y ₃ are the same or different, and each independently a single bond, a substituted or unsubstituted C ₁ -C ₃₀ alkylene group, a substituted or unsubstituted C ₆ -C ₃₀ arylene group, a substituted or An unsubstituted, linking group having a structure of -MN-M'-, wherein M and M' are the same or different and each independently represent a substituted or unsubstituted C ₆ -C ₁₂ arylene group, wherein N is a substituted Or a _{linking group that is an unsubstituted C 1} -C ₁₅ alkylene group, a substituted or unsubstituted, and a linking group having a structure of -PQ-P'-, wherein P and P' are the same or different and each independently substituted or an unsubstituted C ₁ -C ₁₅ alkylene group, wherein Q is a substituted or unsubstituted C ₆ -C ₁₂ arylene group, a linking group, a substituted or unsubstituted C ₇ -C ₃₀ arylalkylene group, substituted or unsubstituted A _{substituted or unsubstituted C 2} -C ₃₀ alkenylene group, a substituted or unsubstituted C ₃ -C ₃₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₃₀ cycloalkenylene group, a substituted or unsubstituted C ₂ -C ₅₀ heteroarylene group, substituted or unsubstituted C ₂ -C ₃₀ heterocycloalkylene group, substituted or unsubstituted C ₁ -C ₃₀ oxyalkylene group (-O-alkylene-), substituted or unsubstituted Any one selected from the C ₆ -C ₃₀ oxyarylene group (-O-arylene-),
The substituents R ₁ to R ₄ are the same or different, and are each independently 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, substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₃₀ alkylsilyl group, substituted or unsubstituted C ₆ - C ₃₀ is any one selected from an arylsilyl group, a cyano group, a nitro group, and a halogen group,
Wherein m1 and m2 are the same or different, and each independently represents an integer of 1 to 8, but when R ₃ or R ₄ is not bonded to a carbon atom of the aromatic ring in the anthracene group, it is bonded to hydrogen or deuterium,
When m1 or m2 is 2 or more, each R ₃ or R ₄ is the same as or different from each other,
Wherein n ₁ and n ₂ are the same or different, and each independently an integer of 1 to 4, when n ₁ is 2 or more, each 'Ar ₁ -L ₃ -Y ₁ -L ₁ -' are the same as or different from each other, and when n ₂ is 2 or more, each 'Ar ₂ -L ₄ -Y ₂ -L ₂ -' bonded to the phenyl group is the same as or different from each other,
When (5-n1) is 2 or more, each R1 is the same as or different from each other, and when (5-n2) is 2 or more, each R2 is the same or different from each other, and
The substituents Ar ₁ and A _r2 are the same or different from each other, and are each independently selected from the following [Structural Formula 1] to [Structural Formula 3],
[Structural Formula 1]

[Structural formula 2] [Structural formula 3]

In Structural Formula 1,
The substituents R ₇ to R ₁₁ are the same as or different from each other, and are 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 unsubstituted C ₆ - C ₃₀ Arylsilyl group, cyano group, nitro group, halogen group. Any one selected from the substituent Q1,
At least one of the substituents R ₇ to R ₁₁ is the substituent Q1, and '*' in the substituent Q1 means a bonding site bonded to an aromatic carbon atom of the phenyl group in Structural Formula 1,
When the substituent Q1 is 2 or more, each Q1 is the same as or different from each other,
The substituent R ₁₂ is selected from hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₅ alkyl group,
In the [Structural Formula 1] to [Structural Formula 3], the '**' means a binding site connected to the _{linking group L 3} or L _{4 in Formula (1),}
Here, 'substitution' in 'substituted or unsubstituted' in Formula (1) is deuterium, cyano group, halogen group, hydroxyl group, nitro group, C ₁ -C ₂₄ alkyl group, 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 Heteroarylamino group, C ₁ -C ₂₄ Alkylsilyl group, C ₆ -C ₂₄ Arylsilyl group, C ₆ -C _{24 It} means substituted with one or more substituents selected from the group consisting of an 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 represents any one selected from a single bond, a sulfur atom (S) and 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 represents any one selected from a single bond, a sulfur atom (S) and an oxygen atom (O).
The method of claim 1,
The linking _{groups L 5} and L ₆ are the same as or different from each other, and each independently an oxygen atom (O) or a sulfur atom (S).
According to claim 1,
Wherein Y _{1 To} Y _{3 Are} the same as or different from each other, and each independently a single bond, a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, substituted or unsubstituted cyclic, as a linking group having the structure of -MN-M'-, wherein M and M' are the same or different and each independently represent a substituted or unsubstituted C ₆ -C ₁₂ arylene group, wherein N is a substituted or A linking group that is an unsubstituted C ₁ -C ₁₂ alkylene group, a substituted or unsubstituted, and a linking group having a structure of -PQ-P'-, wherein P and P' are the same or different and independently of each other, substituted or unsubstituted a cyclic C ₁ -C ₁₂ alkylene group, wherein Q is a substituted or unsubstituted C ₆ -C ₁₂ arylene group, a linking group, a substituted or unsubstituted C ₇ -C ₁₈ arylalkylene group, substituted or unsubstituted a C ₂ -C ₁₂ alkenylene group, a substituted or unsubstituted C ₃ -C ₁₄ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₁₄ cycloalkenylene group, a substituted or unsubstituted C ₂ - C ₁₈ heteroarylene group, substituted or unsubstituted C ₂ -C ₁₂ heterocycloalkylene group, substituted or unsubstituted C ₁ -C ₁₂ oxyalkylene group (-O-alkylene-), substituted or unsubstituted C ₆ -C ₁₈ An oxyarylene group (-O-arylene-), a compound characterized in that any one linking group selected from.
6. The method of claim 5,
Wherein Y ₃ is a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, a substituted or unsubstituted, and a linking group having the structure of -MN-M'- , wherein M and M' are the same or different, and each independently represents a substituted or unsubstituted C ₆ -C ₁₂ arylene group, wherein N is a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, a linking group, substituted Or an unsubstituted, linking group having a structure of -PQ-P'-, wherein P and P' are the same or different and are each independently a substituted or unsubstituted C ₁ -C ₁₂ alkylene group, wherein Q is Any one selected from a linking group that is a substituted or unsubstituted C ₆ -C ₁₂ arylene group, a substituted or unsubstituted C ₇ -C ₁₈ arylalkylene group, and a substituted or unsubstituted C ₃ -C ₁₄ cycloalkylene group A compound characterized in that it is a linking group of
The method of claim 1,
The Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents the [Structural Formula 1].
8. The method of claim 7,
A compound, characterized in that only one or two of _{R 7} to R ₁₁ in Structural Formula 1 is a substituent Q1. _{Here, when only two of R 7} to R ₁₁ in Structural Formula 1 are the substituents Q1, they are the same as or different from each other.
According to claim 1,
The linking _{groups L 1} to L ₆ are the same or different from each other, and each independently represents any one selected from a single bond, an oxygen atom (O) and a sulfur atom (S).
According to claim 1,
Wherein n ₁ and n ₂ are each the same or different, and each independently 1 or 2 compound.
According to claim 1,
The compound represented by Formula (1) is a compound represented by any one selected from the following [Compound 1] to [Compound 166].

[Compound 1] [Compound 2]

[Compound 3] [Compound 4]

[Compound 5] [Compound 6]

[Compound 7] [Compound 8]

[Compound 9] [Compound 10]

[Compound 11] [Compound 12]

[Compound 13] [Compound 14]

[Compound 15] [Compound 16]

[Compound 17] [Compound 18]

[Compound 19] [Compound 20]

[Compound 21] [Compound 22]

[Compound 23] [Compound 24]

[Compound 25] [Compound 26]

[Compound 27] [Compound 28]

[Compound 29] [Compound 30]

[Compound 31] [Compound 32]

[Compound 33] [Compound 34]

[Compound 35] [Compound 36]

[Compound 37] [Compound 38]

[Compound 39] [Compound 40]

[Compound 41] [Compound 42]

[Compound 43] [Compound 44]

[Compound 45] [Compound 46]

[Compound 47] [Compound 48]

[Compound 49] [Compound 50]

[Compound 51] [Compound 52]

[Compound 53] [Compound 54]

[Compound 55] [Compound 56]

[Compound 57] [Compound 58]

[Compound 59] [Compound 60]

[Compound 61] [Compound 62]

[Compound 63] [Compound 64]

[Compound 65] [Compound 66]

[Compound 67] [Compound 68]

[Compound 69] [Compound 70]

[Compound 71] [Compound 72]

[Compound 73] [Compound 74]

[Compound 75] [Compound 76]

[Compound 77] [Compound 78]

[Compound 79] [Compound 80]

[Compound 81] [Compound 82]

[Compound 83] [Compound 84]

[Compound 85] [Compound 86]

[Compound 87] [Compound 88]

[Compound 89] [Compound 90]

[Compound 91] [Compound 92]

[Compound 93] [Compound 94]

[Compound 95] [Compound 96]

[Compound 97] [Compound 98]

[Compound 99] [Compound 100]

[Compound 101] [Compound 102]

[Compound 103] [Compound 104]

[Compound 105] [Compound 106]

[Compound 107] [Compound 108]

[Compound 109] [Compound 110]

[Compound 111] [Compound 112]

[Compound 113] [Compound 114]

[Compound 115] [Compound 116]

[Compound 117] [Compound 118]

[Compound 119] [Compound 120]

[Compound 121] [Compound 122]

[Compound 123] [Compound 124]

[Compound 125] [Compound 126]

[Compound 127] [Compound 128]

[Compound 129] [Compound 130]

[Compound 131] [Compound 132]

[Compound 133] [Compound 134]

[Compound 135] [Compound 136]

[Compound 137] [Compound 138]

[Compound 139] [Compound 140]

[Compound 141] [Compound 142]

[Compound 143] [Compound 144]

[Compound 145] [Compound 146]

[Compound 147] [Compound 148]

[Compound 149] [Compound 150]

[Compound 151] [Compound 152]

[Compound 153] [Compound 154]

[Compound 155] [Compound 156]

[Compound 157] [Compound 158]

[Compound 159] [Compound 160]

[Compound 161] [Compound 162]

[Compound 163] [Compound 164]

[Compound 165] [Compound 166]
A coating solution composition for an organic film material comprising at least one or more of the compounds of any one of claims 1 to 11.
13. The method of claim 12,
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 opposite 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 solution composition for an organic film material according to claim 12 .
15. The method of claim 14,
The organic layer is an organic light emitting device, characterized in that the light emitting layer.
An electronic device comprising the organic light emitting device according to claim 14 .