KR20220028353A - Novel compound, coating composition comprising same, organic light emitting device using same and method of manufacturing same - Google Patents

Abstract

The present specification relates to a compound represented by chemical formula 1, a coating composition comprising the compound represented by the chemical formula 1, an organic light emitting device using the same, and a manufacturing method thereof. The compound of chemical formula 1 of the present invention can be used as a material for an organic material layer of the organic light emitting device, and a device having a low driving voltage, and excellent efficiency and lifespan characteristics can be obtained, and a solution process is possible, so that it is possible to enlarge a device.

Description

Novel compound, coating composition comprising same, organic light emitting device using same, and manufacturing method thereof {NOVEL COMPOUND, COATING COMPOSITION COMPRISING SAME, ORGANIC LIGHT EMITTING DEVICE USING SAME AND METHOD OF MANUFACTURING SAME}

The present specification relates to a novel compound, a coating composition including the compound, an organic light emitting device formed using the coating composition, and a method for manufacturing 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 the 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 generally include a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and an electron transport layer.

Conventionally, a deposition process has been mainly used to manufacture an organic light emitting device. However, there is a problem that a lot of material loss occurs and it is difficult to manufacture a device having a large area when manufacturing an organic light emitting device through the deposition process. To solve these problems, a device using a solution process is being developed.

Accordingly, there is a demand for development of materials for solution processing.

Korean Patent Publication No. 10-2000-0051826

An object of the present specification is to provide a novel compound and an organic light emitting device including the same.

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

[Formula 1]

In Formula 1,

At least one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted aryl group,

At least one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted aryl group,

At least one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted aryl group,

R1 to R4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. is a flag,

n1, n3 and n4 are each an integer of 0 to 4, n2 is an integer of 0 to 3, and when n1 to n4 are each 2 or more, the substituents in two or more parentheses are the same as or different from each other,

Formula 1 includes at least one fluoro group.

The present specification provides a coating composition comprising the compound.

The present specification also includes a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the at least one organic material layer provides an organic light emitting device including the above-described coating composition or a cured product thereof.

Finally, the present specification includes the steps of preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein the forming of the one or more organic material layers includes forming one or more organic material layers using the coating composition. A method of manufacturing a device is provided.

The compound of Formula 1 of the present invention can be used as a material for an organic material layer of an organic light emitting device, and can obtain a device having a low driving voltage and excellent efficiency and lifespan characteristics, and a solution process is possible so that a large area of the device is possible.

In addition, since the compound of Formula 1 of the present invention includes at least one fluoro group (-F) in the compound, a device having a long lifespan can be obtained when applied to a device.

In addition, when the organic material layer containing the compound of Formula 1 of the present invention is formed through a solution process after forming the organic material layer of the upper layer, the organic layer containing the compound of Formula 1 is not dissolved in the solution process solvent of the upper layer. There is an advantage that the performance of the device is not deteriorated.

1 illustrates an example of an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in detail.

In the present specification, when a member (layer) is said to be located “on” another member (layer), this is not only when a member (layer) is in contact with another member but also between two members (layers). (layer) is also included.

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

As used herein, the term “photocurable group and thermosetting group” may refer to a reactive substituent that cross-links compounds by exposing them to heat and/or light. Crosslinking may be generated while radicals generated while decomposing carbon-carbon multiple bonds or cyclic structures are connected by heat treatment or light irradiation.

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

In the present specification, “-----” refers to a site bonded to another substituent or a bonding group.

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

As used herein, the term "substituted or unsubstituted" is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, and a heteroaryl group, It means that it is unsubstituted or substituted with a substituent to which two or more substituents are connected among the above-exemplified substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In addition, as used herein, the term “substituted or unsubstituted” refers to deuterium, a halogen group, a nitrile group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, 6 to 60 carbon atoms. It means unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 2 to 60 carbon atoms, or substituted or unsubstituted with a substituent to which two or more substituents among the above-exemplified substituents are connected.

In the present specification, the halogen group is a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br), or an iodo group (-I).

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. Specific examples of the alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, etc. , but not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group may have 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.

In the present specification, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but may be 1 to 20 carbon atoms. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, n-propoxy group, n-butoxy group, tert-butoxy group, n-pentyloxy group, n-hexyloxy group, n-octyloxy group, n-no It may be a nyloxy group, an n-decyloxy group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may include, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, and the like.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

spirofluorenyl groups such as

(9,9-dimethyl fluorenyl group), and

a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the heteroaryl group is an aromatic ring group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but may be 2 to 60 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of the heteroaryl group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, and the like. However, the present invention is not limited thereto.

According to an exemplary embodiment of the present specification, there is provided a compound represented by Formula 1 above.

According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 has one or more fluoro groups and thus has a high HOMO energy level, thereby including the compound of Chemical Formula 1 in the hole injection layer in the organic light emitting device. In this case, by facilitating the injection of holes from the hole injection layer to the hole transport layer, it has a major effect on improving the lifespan of the device.

As used herein, "energy level" means an energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, when the energy level is deep, the absolute value increases in the negative direction from the vacuum level.

In the present specification, the highest occupied molecular orbital (HOMO) refers to a molecular orbital (highest occupied molecular orbital) in the region with the highest energy in the region where electrons can participate in bonding, and the lowest unoccupied molecular orbital (LUMO). is the molecular orbital function (lowest unoccupied molecular orbital) in which electrons are in the lowest energy region among the antibonding regions, and the HOMO energy level means the distance from the vacuum level to the HOMO. In addition, the LUMO energy level means the distance from the vacuum level to the LUMO.

According to an exemplary embodiment of the present specification, the compound of Formula 1 is preferably a compound having solubility in a suitable organic solvent.

In addition, in the case of the compound according to an exemplary embodiment of the present specification, an organic light emitting device can be manufactured by a solution coating method, so that the device can have a large area.

In the exemplary embodiment of the present specification, Chemical Formula 1 includes at least one fluoro group (-F).

According to another exemplary embodiment, Chemical Formula 1 includes 1 to 6 fluoro groups (-F).

In another exemplary embodiment, any one of Ar1 and Ar2 in Formula 1 includes a fluoro group.

In another exemplary embodiment, any one of Ar3 and Ar4 in Formula 1 includes a fluoro group.

In another exemplary embodiment, any one of Ar5 and Ar6 in Formula 1 includes a fluoro group.

According to another exemplary embodiment, at least one of R1, R3, and R4 in Formula 1 is a fluoro group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

The definitions of the substituents are the same as in Formula 1.

In an exemplary embodiment of the present specification, in the definitions of Ar1 to Ar6, “fluorene substituted with a photocurable group or a thermosetting group” may be unsubstituted or substituted with an additional substituent in addition to the photocurable group and the thermosetting group.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, at least one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. It is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, at least one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted phenyl group; or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, at least one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. It is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, at least one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted phenyl group; or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, at least one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, at least one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. It is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, at least one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted phenyl group; or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, any one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, the other is a substituted or unsubstituted aryl group, and any one of Ar3 and Ar4 is a photocurable group fluorene substituted with a chemical group or a thermosetting group, the other one is a substituted or unsubstituted aryl group, any one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is substituted or unsubstituted is an aryl group.

According to an exemplary embodiment of the present specification, any one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, any one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is at least one substituent selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. An aryl group having 6 to 60 carbon atoms is unsubstituted or substituted with

According to another exemplary embodiment, any one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is at least one substituent selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. A phenyl group unsubstituted or substituted with; or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, any one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, any one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is at least one substituent selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. An aryl group having 6 to 60 carbon atoms is unsubstituted or substituted with

According to another exemplary embodiment, any one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is at least one substituent selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. A phenyl group unsubstituted or substituted with; or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, any one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, any one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is at least one substituent selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. An aryl group having 6 to 60 carbon atoms is unsubstituted or substituted with

According to another exemplary embodiment, any one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is at least one substituent selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms. A phenyl group unsubstituted or substituted with; or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a fluoro group and an alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the photocurable group and the thermosetting group are any one of the following structures.

According to an exemplary embodiment of the present specification, the -NAr1Ar2, -NAr3Ar4 and -NAr5Ar6 are the same as or different from each other, and are each independently represented by the following formula (A).

[Formula A]

In the formula A,

R10 to R13 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. is a flag,

Y is a photocurable group or a thermosetting group,

n10 is an integer from 0 to 5, n11 is an integer from 0 to 3, n12 is an integer from 0 to 4, and when n10 to n12 are 2 or more, two or more substituents in parentheses are the same as or different from each other.

The '-----' refers to a bonding position.

According to an exemplary embodiment of the present specification, Chemical Formula A is represented by the following Chemical Formula A-1.

[Formula A-1]

In the formula A-1,

The definitions of the substituents are as in Formula A.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 4 below.

[Formula 4]

In Formula 4,

The definitions of R1 to R4 and n1 to n4 are the same as in Formula 1,

R10', R10'', R10''', R11', R11'', R11''', R12', R12'', R12''', R13', R13'' and R13''' are the same or different, each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

Y', Y'' and Y''' are the same as or different from each other, and each independently a photocurable group or a thermosetting group,

n10', n10'' and n10''' are each an integer from 0 to 5, n11', n11'' and n11''' are each an integer from 0 to 3, n12', n12'' and n12'' ' is an integer of 0 to 4, respectively, and n10', n10'', n10''', n11', n11'', n11''', n12', n12'' and n12''' are each 2 or more. In case two or more substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 4 is represented by the following Chemical Formula 4-1 or 4-2.

[Formula 4-1]

[Formula 4-2]

In Formulas 4-1 and 4-2,

The definitions of the substituents are the same as in Formula 4.

According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 1 to an alkoxy group of 20, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R1 to R4 are the same as or different from each other, and each independently represent hydrogen or a fluoro group.

According to an exemplary embodiment of the present specification, n1 to n4 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, the R10, R10', R10'', R10''', R11, R11', R11'', R11''', R12, R12', R12'', R12'' ', R13, R13', R13'' and R13'' are the same as or different from each other, and each independently represent hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, R10, R10', R10'' and R10'' are the same as or different from each other, and each independently hydrogen, a fluoro group, an alkyl group having 1 to 20 carbon atoms, or 1 to carbon atoms It is a C6-C30 aryl group unsubstituted or substituted with a 20-alkyl group.

In an exemplary embodiment of the present specification, R10, R10', R10'' and R10''' are the same as or different from each other, and each independently substituted with hydrogen, a fluoro group, a methyl group, or an alkyl group having 1 to 20 carbon atoms. is a phenyl group.

In the exemplary embodiment of the present specification, the n10, n10', n10'' and n10''' are each an integer of 0 to 2, and the n10, n10', n10'' and n10''' are each 2 In this case, the substituents in the two parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, R11, R11', R11'', R11''', R12, R12', R12'' and R12''' are the same as or different from each other, and each independently hydrogen, fluorine an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a rho group, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R11, R11', R11'', R11''', R12, R12', R12'' and R12''' are each hydrogen.

According to an exemplary embodiment of the present specification, the n11, n11', n11'', n11''', n12, n12', n12'' and n12''' are each an integer of 0 to 2, and the n11, n11 When ', n11'', n11''', n12, n12', n12'' and n12''' are each 2, the substituents in the two parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, R13, R13', R13'' and R13''' are the same as or different from each other, and each independently hydrogen; or a substituted or unsubstituted C6-C60 aryl group.

According to another exemplary embodiment, R13, R13', R13'' and R13''' are the same as or different from each other, and each independently hydrogen; or an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with an alkyl group.

According to another exemplary embodiment, R13, R13', R13'' and R13''' are the same as or different from each other, and each independently hydrogen; or an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R13, R13', R13'' and R13'' are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R13, R13', R13'' and R13''' are each a dimethylphenyl group.

In the exemplary embodiment of the present specification, Chemical Formula 4 is represented by the following Chemical Formula 4-A or 4-B.

[Formula 4-A]

[Formula 4-B]

In the formulas 4-A and 4-B,

R1 to R4, n1 to n4, R10', R10'', R10''', R11', R11'', R11''', R12', R12'', R12''', R13', R13'' , R13''', Y', Y'', Y''', n10', n10'', n10''', n11', n11'', n11''', n12', n12'' and n12 The definition of ''' is the same as in Formula 4,

R101 to R106 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. is a flag,

m1 to m3 are each an integer of 0 to 4, m4 to m6 are each an integer of 0 to 3, and when m1 to m6 are each 2 or more, the substituents in two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently hydrogen, a fluoro group, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms or unsubstituted carbon atoms It is an aryl group of 6 to 30.

In an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently represents a phenyl group substituted with hydrogen, a fluoro group, a methyl group, or an alkyl group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R104 to R106 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 1 to an alkoxy group of 20, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R104 to R106 are the same as or different from each other, and are each independently hydrogen or a fluoro group.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds.

The compound according to an exemplary embodiment of the present specification may have a core structure as in Preparation Examples to be described later. In addition, the substituents may be combined by a method known in the art, and the type, position or number of the substituents may be changed according to a method known in the art.

In one embodiment of the present specification, there is provided a coating composition comprising the compound of Formula 1 described above.

In an exemplary embodiment of the present specification, the coating composition includes the compound of Formula 1 and a solvent.

In one embodiment of the present specification, the coating composition may be in a liquid state. The "liquid phase" means a liquid state at room temperature and pressure.

In one embodiment of the present specification, the solvent is, for example, a chlorine-based solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, Isophorone, Tetralone, Decalone, and Acetylacetone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol alcohols and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; A solvent such as tetralin is exemplified, but any solvent capable of dissolving or dispersing the compound of Formula 1 according to an exemplary embodiment of the present invention is sufficient, and the present invention is not limited thereto.

In another exemplary embodiment, the solvent may be used alone or as a mixture of two or more solvents.

In one embodiment of the present specification, the coating composition does not further include a p-doping material.

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

In the present specification, the p-doped material refers to a material that allows the host material to have p-semiconductor properties. The p-semiconductor property refers to the property of receiving or transporting holes at the highest occupied molecular orbital (HOMO) energy level, that is, the property of a material having high hole conductivity.

The p-doping material may have any one of the following structures, but is not limited thereto.

In an exemplary embodiment of the present specification, the content of the p-doping material is 0% to 50% by weight based on the compound of Formula 1 above.

In another exemplary embodiment, the content of the p doping material includes 0 to 30% by weight based on the total solid content of the coating composition. In an exemplary embodiment of the present specification, the content of the p doping material is preferably 1 to 30% by weight based on the total solid content of the coating composition, and in another exemplary embodiment, the p doping material It is more preferable that the content of the coating composition comprises 10 to 30% by weight based on the total solid content of the coating composition.

In another embodiment, the coating composition is a single molecule comprising a photocurable group and / or thermosetting group; Alternatively, it may further include a single molecule including a terminal group capable of forming a polymer by heat. Monomolecules containing a photocurable group and/or a thermosetting group as described above; Alternatively, the molecular weight of a single molecule including a terminal group capable of forming a polymer by heat may be a compound of 3,000 g/mol or less.

a single molecule comprising the photocurable group and/or the thermosetting group; Alternatively, a single molecule including a terminal group capable of forming a polymer by heat may be aryl such as phenyl, biphenyl, fluorene, or naphthalene; arylamine; Alternatively, it may refer to a single molecule in which a photocurable group and/or a thermosetting group or a terminal group capable of forming a polymer by heat is substituted with fluorene.

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

When the above viscosity is satisfied, it is easy to manufacture a device. Specifically, a uniform film may be formed when the organic material layer in the device is formed.

The present specification also provides an organic light emitting device formed using the coating composition.

In one embodiment of the present specification, the first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers includes the coating composition or a cured product thereof, and the cured product of the coating composition is the The coating composition is in a cured state by heat treatment or light treatment.

In an exemplary embodiment of the present specification, the organic material layer including the coating composition or a cured product thereof is a hole transport layer or a hole injection layer.

In an exemplary embodiment of the present specification, the organic material layer including the coating composition or a cured product thereof is an electron transport layer or an electron injection layer.

In another embodiment, the organic material layer including the coating composition or a cured product thereof is a light emitting layer.

In another exemplary embodiment, the organic material layer including the coating composition or a cured product thereof is a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a host of the light emitting layer.

In another exemplary embodiment, the organic material layer including the coating composition or a cured product thereof is a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a dopant of the light emitting layer.

In the present specification, the cured product means that the coating composition is cured by heat treatment and/or light treatment.

In an exemplary embodiment of the present specification, the organic light emitting device includes a hole injection layer and a hole transport layer. It further includes one or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a hole injection and transport layer, and an electron transport and injection layer.

In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

In another exemplary embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole injection and transport layer, an electron injection and transport layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIG. 1 .

In FIG. 1 , a first electrode 201 , a hole injection layer 301 , a hole transport layer 401 , a light emitting layer 501 , an electron injection and transport layer 601 , and a second electrode 701 are sequentially arranged on a substrate 101 . The structure of the organic light emitting device stacked with Here, the electron injection and transport layer means a layer that simultaneously injects and transports electrons. The hole injection layer 301 and/or the hole transport layer 401 of FIG. 1 may be formed using a coating composition including the compound of Formula 1 described above.

1 illustrates an organic light emitting device, but is not limited thereto.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer is formed using a coating composition including the compound of Formula 1 above.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and an organic material layer including at least one layer of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole injection and transport layer, and an electron injection and transport layer thereon. It can be prepared by depositing a material that can be used as a cathode on it. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The present specification also provides a method of manufacturing an organic light emitting device formed using the coating composition.

Specifically, in one embodiment of the present specification, the steps of preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein the forming of the one or more organic material layers includes forming one or more organic material layers using the coating composition.

In one embodiment of the present specification, the step of forming one or more organic material layers using the coating composition uses a spin coating method.

In another embodiment, the step of forming one or more organic material layers using the coating composition uses a printing method.

In the present specification, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited thereto.

Since the coating composition according to an exemplary embodiment of the present specification is suitable for a solution process due to its structural characteristics, it can be formed by a printing method, thereby having an economical effect in terms of time and cost when manufacturing a device.

In one embodiment of the present specification, the step of forming one or more organic material layers using the coating composition comprises: coating the coating composition on the first electrode or one or more organic material layers; and heat-treating or light-treating the coated coating composition.

In an exemplary embodiment of the present specification, the heat treatment may be performed through heat treatment, and the heat treatment temperature in the heat treatment step may be 85° C. to 250° C., and according to an exemplary embodiment, 100° C. to 250° C., In another exemplary embodiment, it may be 150 °C to 250 °C.

In another exemplary embodiment, the heat treatment time in the heat treatment step is 1 minute to 2 hours, according to an exemplary embodiment may be 1 minute to 1 hour, in another exemplary embodiment, 30 minutes to It can be 1 hour.

When the step of forming one or more organic material layers formed by using the coating composition includes the heat treatment or light treatment step, a plurality of the compounds included in the coating composition form cross-linking to provide an organic material layer including a thinned structure. can In this case, when another layer is laminated on the surface of the organic material layer formed by using the coating composition, it can be prevented from being dissolved, morphologically affected, or decomposed by a solvent.

Therefore, when the organic material layer formed by using the coating composition is formed including a heat treatment or light treatment step, resistance to solvent increases, so that a multilayer can be formed by repeatedly performing solution deposition and crosslinking methods, and stability of the device is increased Lifespan characteristics can be increased.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include the compound of Formula 1, metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, and quinacridone-based organic material. , perylene-based organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or hole injection layer to the light emitting layer and has high hole mobility. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The hole injection and transport layer may include the material of the hole transport layer and the hole injection layer described above.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene, and the like, having an arylamino group. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. Do. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons as an electron injection material, has an electron injection effect from the cathode, has an excellent electron injection effect on the light emitting layer or the light emitting material, and is generated in the light emitting layer A compound which prevents the exciton from moving to the hole injection layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

The electron injection and transport layer may include the material of the electron transport layer and the electron injection layer described above.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

The electron blocking layer is a layer that blocks electrons from reaching the anode, and a material known in the art may be used.

The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

< production example >

production example 1: Preparation of compound 1

Step 1) Preparation of Intermediate 1-1

2-bromo-9-(2,5-dimethylphenyl)-9-(4-vinylphenyl)-9H-fluorene (10 g, 22.2 mmol), 3-fluoro-4-methylaniline (2.5 g, 20 mmol) in toluene After dissolution, NaOtBu (10.7 g, 111 mmol) and Pd(tBu ₃ P) ₂ (1.13 g, 2.22 mmol) were added, and the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was purified by recrystallization in hexane to obtain Intermediate 1-1.

Step 2) Preparation of compound 1

4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl (1 g, 1.8 mmol), intermediate 1-1 (3 g, 6.1 mmol) After dissolving in toluene, NaOtBu (707 mg, 7.4 mmol) and Pd(tBu ₃ P) ₂ (47 mg, 0.1 mmol) were added, and then the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was subjected to column purification to obtain Compound 1.

production example 2: Preparation of compound 2

3,3''-dibromo-5'-(3-bromophenyl)-1,1':3',1''-terphenyl (1 g, 1.8 mmol), Intermediate 1-1 (3 g, 6.1 mmol) After dissolving in toluene, NaOtBu (707 mg, 7.4 mmol) and Pd(tBu ₃ P) ₂ (47 mg, 0.1 mmol) were added, and then the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was subjected to column purification to obtain Compound 2.

production example 3: Preparation of compound 3

Step 1) Preparation of Intermediate 3-1

After dissolving 2-bromo-9-(2,5-dimethylphenyl)-9-(4-vinylphenyl)-9H-fluorene (10 g, 22.2 mmol) and 3,4-difluoroaniline (2.58 g, 20 mmol) in toluene After NaOtBu (10.7 g, 111 mmol) and Pd(tBu ₃ P) ₂ (1.13 g, 2.22 mmol) were added, the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was purified by recrystallization in hexane to obtain Intermediate 3-1.

Step 2) Preparation of compound 3

4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl (1 g, 1.8 mmol), Intermediate 3-1 (3 g, 6.1 mmol) After dissolving in toluene, NaOtBu (707 mg, 7.4 mmol) and Pd(tBu ₃ P) ₂ (47 mg, 0.1 mmol) were added, and then the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was subjected to column purification to obtain compound 3.

production example 4: Preparation of compound 4

Step 1) Preparation of Intermediate 4-1

After dissolving 2-bromo-9-(2,5-dimethylphenyl)-9-(4-vinylphenyl)-9H-fluorene (10 g, 22.2 mmol) and 3,4-difluoroaniline (4.22 g, 20 mmol) in toluene After NaOtBu (10.7 g, 111 mmol) and Pd(tBu ₃ P) ₂ (1.13 g, 2.22 mmol) were added, the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was purified by recrystallization in hexane to obtain Intermediate 4-1.

Step 2) Preparation of compound 4

4,4''-dibromo-5'-(4-bromo-2-fluorophenyl)-2,2''-difluoro-1,1':3',1''-terphenyl (1 g, 1.6 mmol), After dissolving Intermediate 4-1 (5.28 g, 5.28 mmol) in toluene, NaOtBu (614 mg, 6.4 mmol) and Pd(tBu ₃ P) ₂ (41 mg, 0.08 mmol) were added, and then the temperature was raised to 80 ℃ and stirred. did The organic layer extracted with ethyl acetate (EA) was subjected to column purification to obtain compound 4.

production example 5: Preparation of compound 5

4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl (1 g, 1.8 mmol), intermediate 4-1 (3.5 g, 6.1 mmol) After dissolving in toluene, NaOtBu (707 mg, 7.4 mmol) and Pd(tBu ₃ P) ₂ (47 mg, 0.1 mmol) were added, and then the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was subjected to column purification to obtain compound 5.

production example 6: Preparation of compound 6

4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl (1 g, 1.8 mmol), N-phenyl-4-vinylaniline (1.2 g, 6.1 mmol) was dissolved in toluene, NaOtBu (707 mg, 7.4 mmol) and Pd(tBu ₃ P) ₂ (47 mg, 0.1 mmol) were added thereto, and then the temperature was raised to 80 °C and stirred. The organic layer extracted with ethyl acetate (EA) was subjected to column purification to obtain compound 6.

<Experimental example>

Example 1.

A glass substrate on which ITO was deposited as a thin film to a thickness of 1500 Å was ultrasonically cleaned for 10 minutes using an acetone solvent. Thereafter, the detergent was placed in distilled water, washed with ultrasonic waves for 10 minutes, and repeated twice with distilled water, followed by ultrasonic washing for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol for 10 minutes, followed by drying. The substrate was then transported to a glove box.

On the ITO transparent electrode prepared as described above, a 1.5 wt% toluene coating composition comprising the compound 1 prepared in Preparation Example 1 and the following compound A in a weight ratio of 8:2 (compound 1:compound A) was spin-coated on the ITO surface and A hole injection layer was formed with a thickness of 30 nm by heat treatment (curing) at 220° C. for 30 minutes. A hole transport layer having a thickness of 40 nm was formed by spin coating a 2 wt% toluene coating composition of the following α-NPD compound on the hole injection layer.

Thereafter, after transferring to a vacuum evaporator, the weight ratio (ADN:DPAVBi) of the following ADN compound to the following DPAVBi compound was 20:1 on the hole transport layer, and vacuum deposition was performed to a thickness of 20 nm to form a light emitting layer. On the light emitting layer, the following BCP compound was vacuum-deposited to a thickness of 35 nm to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of LiF of the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2Х10 ^-7 ~ 5Х10 ^{- 6} torr was maintained.

Example 2.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1.

Example 3.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1.

Example 4.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1.

comparative example One.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1.

comparative example 2.

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1.

The organic light emitting diodes prepared in Examples 1 to 4 and Comparative Examples 1 and 2 were measured for driving voltage, current efficiency, quantum efficiency (QE) and luminance values at a current density of 10 mA/cm ² , and at a current density of 10 mA/cm ² The time (T90) at which the current density becomes 90% of the initial luminance was measured. The results are shown in Table 1 below.

device Driving voltage (V) current efficiency
(cd/A) QE (%) Life T90
(10mA/cm ² ) Example 1 4.95 6.05 6.50 26 Example 2 4.78 6.05 6.38 29 Example 3 5.01 5.85 6.23 21 Example 4 5.22 6.24 6.78 21 Comparative Example 1 5.65 5.53 6.13 12 Comparative Example 2 6.33 3.55 4.08 5

Examples 1 to 4, in which organic light emitting devices were manufactured using the compound of the present invention, Comparative Example 1 using compound 5 not containing a fluoro group in the compound, and compound 6 not containing fluorene substituted with a curable group were used It can be seen from Table 1 that the driving voltage of the organic light emitting diode is lower than that of Comparative Example 2, and the current efficiency, quantum efficiency (QE) and lifespan characteristics are excellent.

101: substrate
201: first electrode
301: hole injection layer
401: hole transport layer
501: light emitting layer
601: electron injection and transport layer
701: second electrode

Claims (14)

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

In Formula 1,
At least one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted aryl group,
At least one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted aryl group,
At least one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the remainder is a substituted or unsubstituted aryl group,
R1 to R4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. is a flag,
n1, n3 and n4 are each an integer of 0 to 4, n2 is an integer of 0 to 3, and when n1 to n4 are each 2 or more, the substituents in two or more parentheses are the same as or different from each other,
Formula 1 includes at least one fluoro group. The method according to claim 1,
Formula 1 is a compound represented by Formula 2 or 3 below:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
The definitions of the substituents are the same as in Formula 1. The method according to claim 1,
A compound wherein the photocurable group and the thermosetting group have any one of the following structures:

. The method according to claim 1,
Wherein -NAr1Ar2, -NAr3Ar4 and -NAr5Ar6 are the same as or different from each other, and each independently a compound represented by the following formula (A):
[Formula A]

In the formula A,
R10 to R13 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. is a flag,
Y is a photocurable group or a thermosetting group,
n10 is an integer from 0 to 5, n11 is an integer from 0 to 3, n12 is an integer from 0 to 4, and when n10 to n12 are 2 or more, two or more substituents in parentheses are the same as or different from each other. The method according to claim 1,
Formula 1 is a compound comprising 1 to 6 fluoro groups. The method according to claim 1,
Any one of Ar1 and Ar2 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is a substituted or unsubstituted aryl group,
Any one of Ar3 and Ar4 is fluorene substituted with a photocurable group or a thermosetting group, and the other is a substituted or unsubstituted aryl group,
Any one of Ar5 and Ar6 is fluorene substituted with a photocurable group or a thermosetting group, and the other one is a substituted or unsubstituted aryl group. The method according to claim 1,
Formula 1 is a compound represented by Formula 4 below:
[Formula 4]

In Formula 4,
The definitions of R1 to R4 and n1 to n4 are the same as in Formula 1,
R10', R10'', R10''', R11', R11'', R11''', R12', R12'', R12''', R13', R13” and R13”' are the same as or different from each other and each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Y', Y'' and Y''' are the same as or different from each other, and each independently a photocurable group or a thermosetting group,
n10', n10'' and n10''' are each an integer from 0 to 5, n11', n11'' and n11''' are each an integer from 0 to 3, n12', n12'' and n12''' is an integer of 0 to 4, respectively, and n10', n10'', n10''', n11', n11'', n11''', n12', n12'' and n12''' are each 2 or more. In case two or more substituents in parentheses are the same as or different from each other. 8. The method of claim 7,
Formula 4 is a compound represented by the following Formula 4-1 or 4-2:
[Formula 4-1]

[Formula 4-2]

In Formulas 4-1 and 4-2,
The definitions of the substituents are the same as in Formula 4. The method according to claim 1,
The compound of Formula 1 is represented by any one of the following compounds:

. 10. A coating composition comprising a compound according to any one of claims 1 to 9. a first electrode;
a second electrode; and
At least one organic material layer provided between the first electrode and the second electrode,
One or more of the one or more organic material layers may include the coating composition of claim 10 or a cured product thereof. 12. The method of claim 11,
The organic material layer comprising the coating composition or a cured product thereof is an organic light emitting device that is a hole transport layer or a hole injection layer. preparing a first electrode;
forming one or more organic material layers on the first electrode; and
Comprising the step of forming a second electrode on the one or more organic material layer,
The method of manufacturing an organic light emitting device, wherein the forming of the at least one organic material layer includes forming an organic material layer using the coating composition of claim 10 . 14. The method of claim 13,
The step of forming an organic material layer using the coating composition is
coating the coating composition on the first electrode or one or more organic material layers; and
Method of manufacturing an organic light emitting device comprising the step of heat-treating or light-treating the coated coating composition.

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