KR20230041199A - Novel compound, ink composition comprising same, organic light emitting device comprising same and method of manufacturing same - Google Patents

Abstract

The present invention relates to a compound represented by a chemical formula 1, an ink composition including the compound represented by the chemical formula 1, an organic light emitting device using the same, and a manufacturing method thereof. The compound represented by the chemical formula 1 of the present invention can be used as a material for an organic material layer of an organic light emitting device, and a device having low driving voltage, excellent efficiency characteristics and/or excellent lifespan characteristics can be obtained.

Description

A novel compound, an ink composition containing the same, an organic light emitting device including the same, and a manufacturing method thereof

The present invention relates to a novel compound, an ink composition containing the compound, an organic light emitting device formed using the ink 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 specific organic molecules. The principle of the organic light emitting phenomenon is as follows. When the organic material layer is placed between the anode and the cathode, when a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material 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 be composed of a cathode, an anode, and organic material layers disposed therebetween, such as 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, when manufacturing an organic light emitting device using a deposition process, there are problems that a lot of material loss occurs and it is difficult to manufacture a large-area device. To solve this problem, a device using a solution process is being developed.

Therefore, development of materials for solution processing is required.

Korean Patent Publication No. 10-2012-0112277

It is an object of the present invention to provide a compound and/or an ink composition comprising the same.

An object of the present invention is to provide an organic light emitting device comprising the aforementioned compound and/or the aforementioned ink composition.

An object of the present invention is to provide a method for manufacturing the organic light emitting device described above.

An exemplary embodiment of the present invention provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

X1 to X4 are the same as or different from each other, and are each independently a group represented by Structural Formula 1 below,

X11 to X14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

a1 to a4 are each an integer of 0 or 1, a1+a2 are an integer of 1 or 2, a3+a4 are an integer of 1 or 2,

a11 and a12 are each an integer from 0 to 5;

a13 and a14 are each an integer from 0 to 4;

When a11 to a14 are integers greater than or equal to 2, the substituents in parentheses are the same as or different from each other;

[Structural Formula 1]

In Structural Formula 1,

Y is O, S or Se;

L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent naphthyl group,

R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or bonded to each other to form a ring,

* means a position binding to Formula 1 above.

Another embodiment of the present invention provides an ink composition containing the compound.

An exemplary embodiment of the present invention also includes a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the one or more organic material layers includes the aforementioned ink composition.

Finally, one embodiment of the present invention comprises 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 ink composition. A method for manufacturing a device is provided.

The compound represented by Chemical Formula 1 of the present invention can be used as a material for an organic layer of an organic light emitting device, and a device having low driving voltage, excellent efficiency characteristics and/or excellent lifetime characteristics can be obtained, and a solution process is possible, so that the device It is possible to enlarge the area.

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

Hereinafter, the present invention will be described in detail.

An exemplary embodiment of the present invention provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

X1 to X4 are the same as or different from each other, and are each independently a group represented by Structural Formula 1 below,

X11 to X14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

a1 to a4 are each an integer of 0 or 1, a1+a2 are an integer of 1 or 2, a3+a4 are an integer of 1 or 2,

a11 and a12 are each an integer from 0 to 5;

a13 and a14 are each an integer from 0 to 4;

When a11 to a14 are integers greater than or equal to 2, the substituents in parentheses are the same as or different from each other;

[Structural Formula 1]

In Structural Formula 1,

Y is O, S or Se;

L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent naphthyl group,

R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or bonded to each other to form a ring,

* means a position binding to Formula 1 above.

In the diphenylfluorene compound according to an exemplary embodiment of the present invention, one or more phosphine oxide groups are introduced to the fluorene portion and one or more phosphine oxide groups are introduced to the phenyl portion, thereby increasing the polarity of the compound molecule and forming a polar solvent. solubility increases. In addition, the compound represented by Chemical Formula 1 in the organic light emitting device enables flexible control of electron mobility and has excellent driving voltage characteristics, efficiency characteristics, and/or lifespan characteristics when included in the organic light emitting device.

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

In the present invention, when a member (layer) is said to be located "on" another member (layer), this means that a member (layer) is in contact with another member, as well as another member (layer) between two members (layer). The case where (layer) exists is also included.

In the present invention, when a part "includes" a certain component, it means that it may further include other components without excluding other components unless otherwise stated.

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

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

In the present invention, the term "substituted or unsubstituted" is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, alkyl group, cycloalkyl group, alkoxy group, aryl group and heteroaryl group, or It means that two or more substituents among the substituents are substituted or unsubstituted with a linked substituent. 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, in the present invention, the term "substituted or unsubstituted" refers to heavy hydrogen, a halogen group, an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, and an aryl group having 6 to 60 carbon atoms. And substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group having 2 to 60 carbon atoms, or substituted or unsubstituted with a substituent in which two or more substituents among the above-exemplified substituents are connected.

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

In the present invention, the alkyl group may be straight 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 of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, etc. , but not limited to these.

In the present invention, the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms 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, and a cyclooctyl group.

In the present invention, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5. Specific examples of the alkoxy group include methoxy group, 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 an yloxy group, an n-decyloxy group, and the like, but is not limited thereto.

In the present invention, 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 one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present invention, 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-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present invention, the heteroaryl group is an aromatic ring group containing 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 have 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heteroaryl group is 2 to 30. 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, it is not limited to these.

In the present invention, the above description of the aryl group is applied except that the arylene group is divalent.

According to an exemplary embodiment of the present invention, Formula 1 is represented by Formula 11 below.

[Formula 11]

In Formula 11, X1 to X4, X11 to X14, a1 to a4, and a11 to a14 are as defined in Formula 1 above.

According to an exemplary embodiment of the present invention, X11 to X14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted silyl group; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted silyl group; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted silyl group; or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; A substituted or unsubstituted trialkylsilyl group; or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and the alkyl of the trialkylsilyl group is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. As a preferred example, the alkyl of the trialkylsilyl group is a substituted or unsubstituted methyl group. As a more preferable example, the alkyl of the trialkylsilyl group is a methyl group.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; Or a substituted or unsubstituted tert-butyl group.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted tert-butyl group.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; trimethylsilyl group; A methyl group unsubstituted or substituted with a fluoro group; or a tert-butyl group.

According to an exemplary embodiment of the present invention, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; trimethylsilyl group; methyl group; -CF ₃ ; or a tert-butyl group.

According to an exemplary embodiment of the present invention, X13 and X14 are hydrogen or deuterium.

According to an exemplary embodiment of the present invention, a1 to a4 are integers of 0 or 1, respectively.

According to an exemplary embodiment of the present invention, a1 is an integer of 0 or 1. According to another exemplary embodiment of the present invention, a1 is an integer of 0. According to another exemplary embodiment of the present invention, a1 is an integer of 1.

According to an exemplary embodiment of the present invention, a2 is an integer of 0 or 1. According to another exemplary embodiment of the present invention, a2 is an integer of 0. According to another exemplary embodiment of the present invention, a2 is an integer of 1.

According to an exemplary embodiment of the present invention, a3 is an integer of 0 or 1. According to another exemplary embodiment of the present invention, a3 is an integer of 0. According to another exemplary embodiment of the present invention, a3 is an integer of 1.

According to an exemplary embodiment of the present invention, a4 is an integer of 0 or 1. According to another exemplary embodiment of the present invention, a4 is an integer of 0. According to another exemplary embodiment of the present invention, a4 is an integer of 1.

According to an exemplary embodiment of the present invention, a1+a2 is an integer of 1 or 2. According to another exemplary embodiment of the present invention, a1+a2 is an integer of 1. According to another exemplary embodiment of the present invention, a1+a2 is an integer of 2.

According to an exemplary embodiment of the present invention, a3+a4 is an integer of 1 or 2. According to another exemplary embodiment of the present invention, a3+a4 is an integer of 1. According to another exemplary embodiment of the present invention, a3+a4 is an integer of 2.

According to an exemplary embodiment of the present invention, a11 and a12 are integers of 0 to 5, respectively.

According to an exemplary embodiment of the present invention, a11 is an integer from 0 to 5. According to another exemplary embodiment of the present invention, a11 is an integer of 0. According to another exemplary embodiment of the present invention, a11 is an integer of 1. According to another exemplary embodiment of the present invention, a11 is an integer of 2. According to another exemplary embodiment of the present invention, a11 is an integer of 3. According to another exemplary embodiment of the present invention, a11 is an integer of 4. According to another exemplary embodiment of the present invention, a11 is an integer of 5.

According to an exemplary embodiment of the present invention, a12 is an integer from 0 to 5. According to another exemplary embodiment of the present invention, a12 is an integer of 0. According to another exemplary embodiment of the present invention, a12 is an integer of 1. According to another exemplary embodiment of the present invention, a12 is an integer of 2. According to another exemplary embodiment of the present invention, a12 is an integer of 3. According to another exemplary embodiment of the present invention, a12 is an integer of 4. According to another exemplary embodiment of the present invention, a12 is an integer of 5.

According to an exemplary embodiment of the present invention, a13 and a14 are integers of 0 to 4, respectively.

According to an exemplary embodiment of the present invention, a13 is an integer from 0 to 4. According to another exemplary embodiment of the present invention, a13 is an integer of 0. According to another exemplary embodiment of the present invention, a13 is an integer of 1. According to another exemplary embodiment of the present invention, a13 is an integer of 2. According to another exemplary embodiment of the present invention, a13 is an integer of 3. According to another exemplary embodiment of the present invention, a13 is an integer of 4.

According to an exemplary embodiment of the present invention, a14 is an integer from 0 to 4. According to another exemplary embodiment of the present invention, a14 is an integer of 0. According to another exemplary embodiment of the present invention, a14 is an integer of 1. According to another exemplary embodiment of the present invention, a14 is an integer of 2. According to another exemplary embodiment of the present invention, a14 is an integer of 3. According to another exemplary embodiment of the present invention, a14 is an integer of 4.

According to an exemplary embodiment of the present invention, when a11 to a14 are integers of 2 or greater, the substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present invention, X1 to X4 are the same as or different from each other, and each independently represents a group represented by Structural Formula 1 described above.

According to an exemplary embodiment of the present invention, Y is O, S or Se.

According to a preferred embodiment of the present invention, Y is O.

According to an exemplary embodiment of the present invention, L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent naphthyl group.

According to an exemplary embodiment of the present invention, L is a direct bond; Or a substituted or unsubstituted phenylene group.

According to an exemplary embodiment of the present invention, L is a direct bond or a phenylene group.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or bonded to each other to form a ring.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently contains one or two or more selected from the group consisting of deuterium, a halogen group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted alkoxy group. It is an aryl group having 6 to 12 carbon atoms substituted or unsubstituted with a substituent, or a substituted or unsubstituted phosphindol is formed by combining with each other.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently represents one or two or more substituents selected from the group consisting of a deuterium, a halogen group, an alkyl group unsubstituted or substituted with a fluoro group, and an alkoxy group. It is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or combined with each other to form a substituted or unsubstituted phosphindol.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently deuterium, a fluoro group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, An aryl group having 6 to 12 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted tertbutyl group, a substituted or unsubstituted methoxy group, and a substituted or unsubstituted ethoxy group; They combine with each other to form a substituted or unsubstituted phosphindol.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently deuterium, a fluoro group, a methyl group unsubstituted or substituted with a halogen group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted propyl group. An aryl group having 6 to 12 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted tertbutyl group, a substituted or unsubstituted methoxy group, and a substituted or unsubstituted ethoxy group Or, they combine with each other to form a substituted or unsubstituted phosphindol.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently deuterium, a fluoro group, a methyl group, a trifluoromethyl group, an ethyl group, a propyl group, a tertbutyl group, methoxy and an ethoxy group. It is an aryl group having 6 to 12 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of, or bonded to each other to form a substituted or unsubstituted phosphindol.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group, wherein the phenyl or naphthyl group is deuterium, a fluoro group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, or a substituted or unsubstituted tert group. It is substituted or unsubstituted with one or two or more substituents selected from the group consisting of a butyl group, a substituted or unsubstituted methoxy group, and a substituted or unsubstituted ethoxy group, or is bonded to each other to form a substituted or unsubstituted phosphindol.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently deuterium, a fluoro group, a methyl group, a trifluoromethyl group, an ethyl group, a propyl group, a tertbutyl group, methoxy and an ethoxy group. A phenyl group substituted or unsubstituted with one or two or more substituents selected from the group consisting of, or bonded to each other to form a substituted or unsubstituted phosphindol.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently deuterium, a fluoro group, a methyl group, a trifluoromethyl group, an ethyl group, a propyl group, a tertbutyl group, methoxy and an ethoxy group. A phenyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and are each independently selected from the group consisting of deuterium, a fluoro group, a methyl group, a trifluoromethyl group, an ethyl group, a propyl group, a tertbutyl group, and a methoxy group. It is a phenyl group unsubstituted or substituted with 1 or 2 or more substituents selected.

According to an exemplary embodiment of the present invention, Structural Formula 1 is any one selected from the group consisting of the following Structural Formulas.

In the above structural formula, --- means a position bonded to the above formula (1).

According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is any one selected from the group consisting of the following compounds.

.

.

The compound represented by Chemical Formula 1 according to an exemplary embodiment of the present invention may have a core structure as shown in Reaction Scheme 1 below. In addition, substituents may be combined by a method known in the art, and the type, location or number of substituents may be changed according to techniques known in the art.

<Scheme 1>

Specifically, step 1-1 is a step of preparing intermediate compound A3 having a phosphine group introduced by reacting compound A1 and compound A2, and step 1-2 is a step of oxidizing intermediate compound A3 to form the final compound, the compound represented by Formula 1. It is a step of manufacturing.

In Scheme 1, each substituent corresponds to the definition of the substituent in Formula 1 above.

Hereinafter, an ink composition including the aforementioned compound will be described in detail.

According to an exemplary embodiment of the present invention, the ink composition includes the compound represented by Chemical Formula 1 and a solvent.

According to an exemplary embodiment of the present invention, the ink composition may be in liquid form.

According to an exemplary embodiment of the present invention, 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-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone-based 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; Ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; 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; Solvents such as tetralin are exemplified, but any solvent capable of dissolving or dispersing the compound represented by Formula 1 according to an exemplary embodiment of the present invention is sufficient, but is not limited thereto.

According to an exemplary embodiment of the present invention, the solvent may be used alone or in combination of two or more solvents.

According to an exemplary embodiment of the present invention, the ink composition may include an electron injection layer dopant material; an electron transport layer dopant material; Alternatively, an electron injection and transport layer may further include a dopant material. the electron injection layer dopant material; an electron transport layer dopant material; Alternatively, the electron injection and transport layer dopant material may include at least one selected from the group consisting of organic-inorganic mixtures, metals, and organic salts.

According to an exemplary embodiment of the present invention, the electron injection layer dopant material; an electron transport layer dopant material; Alternatively, the electron injection and transport layer dopant material may be an organic material including a substituent including CN and/or F.

According to an exemplary embodiment of the present invention, the electron injection layer dopant material; an electron transport layer dopant material; Alternatively, the electron injection and transport layer dopant material may include one or more selected from the group consisting of alkali metals, alkaline earth metals, lanthanide metals, Se, Ru, and compounds thereof. Specifically, the alkali metal may be Li. Also, the alkaline earth metal may be Ca and Mg. Also, the compound may be LiF, Liq, and RuCO ₃ . In addition, the lanthanide metal may be Yb.

According to an exemplary embodiment of the present invention, the electron injection layer dopant material; an electron transport layer dopant material; Alternatively, the electron injection and transport layer dopant material may include fullerene. Specifically, the fullerene may be fullerene having 60 carbon atoms or fullerene having 70 carbon atoms.

According to an exemplary embodiment of the present invention, the electron injection layer dopant material; an electron transport layer dopant material; Alternatively, the electron injection and transport layer dopant material may include a halide. Specifically, the halogenated flame may be LiF.

According to an exemplary embodiment of the present invention, the electron injection layer dopant material; an electron transport layer dopant material; or the content of the electron injection and transport layer dopant material is the electron injection layer dopant material; an electron transport layer dopant material; Alternatively, it may be 1% by weight or more and 50% by weight or less based on the total weight of the layer including the electron injection and transport layer dopant material.

According to another exemplary embodiment of the present invention, the ink composition may include a single molecule including a photocurable group and/or a thermosetting group; Or, it further includes a single molecule including an end group capable of forming a polymer by heat. As described above, a single molecule containing a photocurable group and/or a thermosetting group; Alternatively, the molecular weight of a single molecule including an end group capable of forming a polymer by heat may be a compound of 3,000 g/mol or less, but is not limited to the above-exemplified molecular weight.

a single molecule containing the photocurable group and/or thermocurable group; Alternatively, a single molecule including an end 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 fluorene is substituted with a photocurable group and/or a thermosetting group or a terminal group capable of forming a polymer by heat.

According to an exemplary embodiment of the present invention, the ink composition has a viscosity of 2 cP to 15 cP at room temperature. When the above viscosity is satisfied, it is easy to manufacture a device. Specifically, when forming the organic material layer in the organic light emitting device, a uniform film may be formed.

An exemplary embodiment of the present invention is a compound represented by Formula 1; Alternatively, an organic light emitting device including an ink composition including the compound represented by Chemical Formula 1 is provided.

An exemplary embodiment of the present invention provides an organic light emitting device formed using the ink composition.

An exemplary embodiment of the present invention is a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the one or more organic material layers includes the ink composition described above.

Hereinafter, types of organic material layers included in the organic light emitting device described above will be described in detail.

According to an exemplary embodiment of the present invention, the organic light emitting device includes one organic material layer, and the organic material layer includes the compound represented by Chemical Formula 1. As an example, the organic material layer including the compound represented by Chemical Formula 1 is a light emitting layer.

According to another exemplary embodiment of the present invention, the organic light emitting device includes two or more organic material layers, and the two or more organic material layers include the compound represented by Chemical Formula 1. For example, any one organic material layer among the two or more organic material layers includes the compound represented by Chemical Formula 1, and further includes one or more other organic material layers. According to an exemplary embodiment, the remaining one or more organic material layers do not include the compound represented by Chemical Formula 1. According to another exemplary embodiment, the remaining one or more organic material layers further include the compound represented by Chemical Formula 1. However, it is not limited to the above example.

The two or more organic material layers are selected from the group consisting of, for example, a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, and the like Contains two or more layers. In this case, the hole injection and transport layer means a layer that simultaneously injects holes and transports holes, and the electron injection and transport layer means a layer that simultaneously injects and transports electrons. However, the organic material layer constituting the group is only an example, and is not limited to the example. In addition, the two or more organic material layers may include two or more layers performing the same role as necessary. An organic light emitting device according to an example includes a first electron transport layer and a second electron transport layer. However, it is not limited to the above example.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer. As an example, the light emitting layer includes the compound represented by Chemical Formula 1. As a specific example, the light emitting layer includes the compound represented by Chemical Formula 1 as a host of the light emitting layer. As another specific example, the light emitting layer includes the compound represented by Chemical Formula 1 as a dopant of the light emitting layer.

According to an exemplary embodiment of the present invention, the organic material layer includes an electron injection and transport layer, an electron injection layer or an electron transport layer. As an example, the electron injection and transport layer, the electron injection layer or the electron transport layer includes the compound represented by Chemical Formula 1.

According to an exemplary embodiment of the present invention, the organic material layer includes an electron transport layer. As an example, the electron transport layer includes the compound represented by Chemical Formula 1.

According to an exemplary embodiment of the present invention, the organic material layer further includes one or more layers selected from the group consisting of an electron blocking layer, a hole blocking layer, a hole injection layer, a hole transport layer, and a hole injection and transport layer. As an example, one or more layers selected from the group consisting of the electron blocking layer, the hole blocking layer, the hole injection layer, the hole transport layer, and the hole injection and transport layer are a compound represented by Formula 1 or a compound containing the same. It contains an ink composition.

According to an exemplary embodiment of the present invention, the one or more organic material layers include the light emitting layer and the one or more first organic material layers, and at least one of the one or more first organic material layers includes the ink composition described above. In this case, when the one or more first organic material layers are two or more layers, the two or more first organic material layers are the same as or different from each other.

Hereinafter, a laminated structure of the organic material layer and the organic light emitting device including the same will be described in detail.

An organic material layer of an organic light emitting device according to an exemplary embodiment of the present invention has a single-layer structure. For example, the single-layer organic material layer is provided between the first electrode and the second electrode of the organic light emitting device, and the organic material layer includes the compound represented by Chemical Formula 1. According to a specific embodiment, the organic material layer having a single-layer structure is a light emitting layer, and in this case, the light emitting layer includes the compound represented by Chemical Formula 1.

An organic material layer of an organic light emitting device according to another exemplary embodiment of the present invention has a multilayer structure in which two or more organic material layers are stacked. For example, the organic material layer of the multilayer structure is provided between the first electrode and the second electrode of the organic light emitting device.

According to an exemplary embodiment of the present invention, the organic material layer of the multi-layered structure includes a light emitting layer and organic material layers other than the light emitting layer. As an example, the light emitting layer is provided between the first electrode and the second electrode, and an organic material layer other than the light emitting layer is provided between the first electrode and the light emitting layer. As another example, the light emitting layer is provided between the first electrode and the second electrode, and an organic material layer other than the light emitting layer is provided between the light emitting layer and the second electrode. As another example, the light emitting layer is provided between the first electrode and the second electrode, any one organic material layer other than the light emitting layer is provided between the first electrode and the light emitting layer, and any other organic material layer other than the light emitting layer is It is provided between the light emitting layer and the second electrode. However, the above structure is only an example, and is not limited to the above structure. In addition, the organic material layer other than the light emitting layer is selected from the group consisting of, for example, a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, and the like It may be one or more layers, but is not limited thereto.

In general, in an organic light emitting device, a hole injection layer, a hole transport layer, or an electron blocking layer is provided between the anode and the light emitting layer. As a specific example, the hole injection layer is provided over the anode, the hole transport layer is provided over the hole injection layer, and the electron blocking layer is provided over the hole injection layer, but is not limited to the above examples.

Also, in general, an electron injection layer, an electron transport layer, or a hole blocking layer is provided between the cathode and the light emitting layer in an organic light emitting device. As a specific example, the hole blocking layer is provided on the light emitting layer, the electron transport layer is provided on the hole blocking layer, and the electron injection layer is provided on the electron transport layer, but is not limited to the above example.

An organic material layer having a multilayer structure included in an organic light emitting device according to an exemplary embodiment of the present invention includes a light emitting layer; and one or more first organic material layers selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer, wherein the light emitting layer Silver is provided between the first electrode and the second electrode, and the one or more first organic material layers are provided between the light emitting layer and the second electrode. As an example, the one or more first organic material layers include the compound represented by Chemical Formula 1.

According to a preferred embodiment of the present invention, the one or more first organic material layers include an electron injection layer; electron transport layer; and at least one of an electron injection and transport layer. More preferably, the at least one first organic material layer is an electron injection and transport layer.

A structure of an organic light emitting device according to an exemplary embodiment of the present invention is shown in FIG. 1 . 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 formed on a substrate 101. The structure of the stacked organic light emitting device is illustrated. The electron injection and transport layer 601 of FIG. 1 may include a compound represented by Chemical Formula 1; Alternatively, it may include an ink composition including the compound represented by Formula 1, or may be formed using the ink composition. 1 illustrates an organic light emitting device according to an exemplary embodiment of the present invention, but is not limited thereto.

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

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

As described above, the organic light emitting device having a single-layer or multi-layered organic material layer may have, for example, a laminated structure as described below, but is not limited thereto.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) anode/hole transport layer/electron blocking layer/emission layer/electron transport layer/cathode

(11) anode/hole transport layer/electron blocking layer/emission layer/electron transport layer/electron injection layer/cathode

(12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(13) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(14) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode

(15) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(16) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode

(17) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode

(18) anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capsule

(19) anode/hole injection layer/first hole transport layer/second hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capsule

According to an exemplary embodiment of the present invention, 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.

According to another exemplary embodiment of the present invention, 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.

Hereinafter, specific details of the organic material layer described above, materials thereof, and manufacturing methods thereof will be described. However, the organic light emitting diode of the present invention may be manufactured with materials and methods known in the art, except that the organic material layer includes the above compounds.

An organic light emitting device according to an exemplary embodiment of the present invention is formed by using an ink composition containing the compound represented by Chemical Formula 1 above at least one of the organic material layers. Except for this, it can be manufactured with materials and methods known in the art.

For example, the organic light emitting device of the present invention can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode, After forming 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 transport and injection layer, and an electron transport and injection layer thereon through a solution process, a deposition process, etc. It can be manufactured by depositing a material that can be used as a cathode thereon. 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.

An exemplary embodiment of the present invention also provides a method of manufacturing an organic light emitting device formed using the ink composition.

Specifically, according to an exemplary embodiment of the present invention, 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 the organic material layer using the ink composition described above.

According to an exemplary embodiment of the present invention, the step of forming one or more organic material layers using the ink composition uses a spin coating method.

According to another exemplary embodiment of the present invention, the step of forming one or more organic material layers using the ink composition uses a printing method.

According to an exemplary embodiment of the present invention, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited to the above-listed printing methods.

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

According to an exemplary embodiment of the present invention, the forming of one or more organic material layers using the ink composition may include coating the ink composition; and drying the coated ink composition; heat treatment step; and/or a light treatment step.

According to an exemplary embodiment of the present invention, the forming of one or more organic material layers using the ink composition may include coating an ink composition on the first electrode or the one or more organic material layers; and drying the coated ink composition; heat treatment step; and/or a light treatment step. Preferably, the forming of one or more organic material layers using the ink composition may include coating an ink composition on the one or more organic material layers; and drying or heat-treating the coated ink composition. As an example, the forming of one or more organic material layers using the ink composition may include coating an ink composition on the first electrode or the one or more organic material layers; and drying the coated ink composition. As another example, the forming of one or more organic material layers using the ink composition may include coating an ink composition on the first electrode or the one or more organic material layers; and heat-treating the coated ink composition. More preferably, the forming of one or more organic material layers using the ink composition may include coating an ink composition on the one or more organic material layers; and drying and heat-treating the coated ink composition.

According to one embodiment of the present invention, the heat treatment step may be performed through heat treatment, and the heat treatment temperature in the heat treatment step may be 85 ℃ to 250 ℃, according to one embodiment may be 100 ℃ to 250 ℃, and another In one embodiment of, it may be 150 ℃ to 250 ℃.

According to one embodiment of the present invention, the heat treatment time in the heat treatment step is 1 minute to 2 hours, according to one embodiment it may be 1 minute to 1 hour, and in another embodiment, 10 minutes to 1 hour It can be 1 hour. As a preferred example, the heat treatment time in the heat treatment step is 20 minutes to 40 minutes.

In the step of forming one or more organic material layers formed using the ink composition, including the heat treatment or light treatment step, the ink composition includes a photocurable group and/or a single molecule including a thermosetting group; Alternatively, when a single molecule including a terminal group capable of forming a polymer by heat is further included, cross-linking between components included in the ink composition may be formed to provide an organic layer having a thinned structure. In this case, when another layer is laminated on the surface of the organic layer formed using the ink composition, it is possible to prevent it from being dissolved by a solvent, morphologically affected, or decomposed. Therefore, when the organic material layer is formed according to the above manufacturing method, resistance to solvent is increased, so that a multi-layer may be formed by repeatedly performing solution deposition and crosslinking methods, and stability may be increased, thereby increasing lifespan characteristics of the device.

Hereinafter, materials for the above-described anode, cathode, and specific organic layer will be described in detail.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, 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 and an oxide such as Sb; 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 so as to facilitate electron injection into the organic material layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The light emitting layer may include a host material and/or a dopant material.

Examples of the host material include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives and the like, but are not limited thereto.

According to one embodiment of the present invention, as the host material, two or more host materials selected from among the above-described host materials may be mixed and used. For example, an anthracene derivative and a pyrene derivative may be mixed and used in a weight ratio of 1:99 to 99:1. As a more specific example, an anthracene derivative and a pyrene derivative may be mixed and used in a weight ratio of 92:8.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, aromatic amine derivatives include pyrene, anthracene, chrysene, and periplanthene having an arylamine group as condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and one or two or more are selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injecting material has the ability to transport holes and has a hole receiving effect from the anode and an excellent hole injecting effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is desirable. Also, a material having excellent thin film forming ability is preferred. In addition, it is preferable that the 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 metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic substances; perylene-based organic materials; Examples include polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole injection layer may further include a p doping material (p dopant). For example, the p-doped material is F4TCNQ; or a boron anion. In another example, the p-doped material is F4TCNQ; or a boron anion, and the boron anion includes a halogen group. In another example, the p-doped material is F4TCNQ; or a boron anion, wherein the boron anion includes F. As another example, the p-doping material is selected from the following structural formula.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and may have a single layer or a multilayer structure of two or more layers. The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer, and a material having high hole mobility is preferable. As an example, it may be the following compound HTL (Mn: 27,900; Mw: 35,600; measured by GPC using PC standard using an Agilent 1200 series), but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include Al complexes 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 can be used with any desired cathode material, as used according to the prior art. In particular, a suitable cathode material is a conventional material having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that receives electrons from an electrode. As the electron injecting material, it is preferable to have an excellent ability to transport electrons, an electron receiving effect from the cathode, and an excellent electron injecting effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto. Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.

According to a preferred embodiment of the present invention, the electron injection material; the electron transport material; Alternatively, the electron injecting and transporting material to be described later is a compound represented by Formula 1 above.

The electron blocking layer is a layer capable of improving lifespan or efficiency of a device by preventing electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer. A known electron blocking material may be used as the electron blocking material.

The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specific examples of the hole blocking layer material include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes, but are not limited thereto.

The hole injection and transport layer may include the above-described hole injection and hole transport layer materials.

The electron injection and transport layer may include materials for the electron injection and hole transport layers described above.

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 according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

An exemplary embodiment of the present invention is a compound represented by Formula 1; Alternatively, an electronic device including an organic light emitting device including an ink composition including the compound represented by Chemical Formula 1 or an organic material layer formed using the ink composition is provided.

The electronic device is an interlayer insulating film of a semiconductor device, a color filter, a black matrix, an overcoat, a column spacer, a passivation film, a buffer coat film, an insulating film for a multilayer printed circuit board, a cover coat of a flexible copper clad plate, a buffer coat film, and a multilayer printed circuit board Insulation film solder resist film, OLED insulation film, thin film transistor protective film of liquid crystal display device, electrode protective film and semiconductor protective film of organic EL element, OLED insulating film, LCD insulating film, semiconductor insulating film, solar module, touch panel, display panel, etc. It may include all devices and the like, but is not limited thereto.

Hereinafter, examples will be described in detail to explain the present invention in detail. However, embodiments according to the present invention can be modified in many different forms, and the scope of the present invention is not construed as being limited to the embodiments described below. Embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.

<Production Example>

Preparation Example 1. Preparation of Compound 1

Compound 1a dried by oven drying was dissolved in anhydrous tetrahydrofuran [anhydrous THF] ([0.1M]) and then replaced with a nitrogen atmosphere. After lowering the temperature of the solution to -78°C, nBuLi (>3.0 equiv.) was slowly added dropwise and stirred for 30 minutes. Then, compound 1b (2.1 equiv.) was slowly added dropwise. Then, after stirring overnight, the temperature of the solution was lowered to 0° C., and ethanol [EtOH] was slowly added dropwise to terminate the reaction. After separating the water layer, a crude solution was obtained by ethyl acetate [EtOAc] / H ₂ O extraction [extraction], and purified by an EtOAc column to obtain Compound 1c as a white solid. Thereafter, after dissolving Compound 1c in CH ₂ Cl ₂ , the temperature of the solution was lowered to 0° C., and then excess H ₂ O ₂ was slowly added dropwise. After that, thin-layer chromatography [Thin-Layer Chromatography; TLC] to confirm the substitution, and then the reaction was terminated by slowly adding water dropwise. Thereafter, the CH ₂ Cl ₂ layer was separated to obtain Compound 1 through EtOAc column purification. MS: [M+H]+ = 719.7

Preparation Example 2. Preparation of Compound 2

Compound 2 was obtained in the same manner as in Preparation Example 1, except that Compound 2a was used instead of Compound 1a in Preparation Example 1. MS: [M+H]+ = 775.8

Preparation Example 3. Preparation of Compound 3

Compound 3 was obtained in the same manner as in Preparation Example 1, except that Compound 3a was used instead of Compound 1a in Preparation Example 1. MS: [M+H]+ = 737.7

Preparation Example 4. Preparation of Compound 4

Compound 1a, compound 4a (2.3 equiv.), K ₂ CO ₃ (3.0 equiv.) and Pd(PPh ₃ ) ₄ (0.05 equiv.) were dissolved in THF/H ₂ O ([0.2M]) and heated to 80 °C. The temperature was raised and stirred for 6 hours. After confirming the completion of the reaction by TLC, solid crude was obtained by EtOAc/H ₂ O extraction, and compound 4 was obtained by column purification. MS:[M+H] ⁺ = 871.9

Preparation Example 5. Preparation of Compound 5

Compound 5 was obtained in the same manner as in Preparation Example 4, except that Compound 5a was used instead of Compound 4a in Preparation Example 4. MS:[M+H] ⁺ = 871.9

<Device example>

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 500 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product of Fischer Co. was used as a detergent, and distilled water filtered through a second filter of a product of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl and acetone, and after drying, the substrate was washed for 5 minutes and transported to a glove box.

On the ITO transparent electrode, a coating composition in which the compound p-dopant and the compound HIL were dissolved in cyclohexanone at a weight ratio of 2:8 at 5 wt/v% was spin-coated (2500 rpm) and heat-treated at 230 ° C. for 30 minutes ( cured) to form a hole injection layer with a thickness of 1000 Å.

On the hole injection layer, a coating composition in which the compound HTL (Mn: 27,900; Mw: 35,600; measured by GPC using PC Standard using an Agilent 1200 series) was dissolved in toluene at 2 wt / v% was spin-coated ( 2500 rpm) and heat treatment at 230 °C for 20 minutes to form a hole transport layer having a thickness of 1000 Å.

On the hole transport layer, a coating composition in which the light emitting layer host compound A and the light emitting layer dopant compound Dopant in a weight ratio of 98:2 were dissolved in 2 wt/v% in cyclohexanone was spin-coated (2000 rpm) and heat-treated at 145° C. for 15 minutes A light emitting layer was formed to a thickness of 400 Å.

Compound 1 prepared in Synthesis Example 1 and lithium quinolate (LiQ) at a weight ratio of 3:7 were added to a mixed solvent of ethylene glycol and 1-propanol (volume ratio of 8:2) on the light emitting layer at 2 wt/v%. The melted coating composition was spin-coated (2000 rpm) and heat-treated at 145° C. for 10 minutes to form an electron injection and transport layer with a thickness of 300 Å.

A cathode was formed by depositing aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the aluminum deposition rate was maintained at 2 Å/sec, and the vacuum level during deposition was maintained at 2*10 ^-7 to 5*10 ^-8 torr.

Examples 2 to 5.

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 when preparing the electron injection and transport layer.

Comparative Examples 1 and 2.

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound B or C was used instead of Compound 1 in preparing the electron injection and transport layer.

Table 1 shows the results of measuring the driving voltage, external quantum efficiency, luminance, and lifetime of the organic light emitting device prepared in the above Examples and Comparative Examples at a current density of 10 mA/cm ² . The external quantum efficiency was calculated as (number of emitted photons)/(number of charge carriers injected). T95 means the time (hr) required for the luminance to decrease from the initial luminance (500 nit) to 95%.

Driving voltage (V) Current efficiency (Cd/A) Power efficiency (lm/W) Luminance (Cd/m ² ) T95 (h) Example 1 4.63 5.08 3.45 507.68 111 Example 2 4.61 5.01 3.42 501.38 188 Example 3 4.74 4.93 3.26 492.72 137 Example 4 4.55 4.78 3.30 478.21 148 Example 5 4.42 4.78 3.40 477.668 180 Comparative Example 1 6.14 4.82 2.47 481.92 85 Comparative Example 2 5.61 3.97 2.22 396.55 67

As shown in Table 1, in the organic light-emitting device using the compound represented by Formula 1 according to the present invention as an electron injection and transport material, a substituent (phosphine oxide group) is introduced only in the diphenyl portion of diphenylfluorene, or a flue Compared to the comparative example using the compound in which the substituent (phosphine oxide group) was introduced only in the orene portion, it was confirmed that the driving voltage was greatly reduced and the efficiency and lifespan characteristics were greatly improved.

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 (13)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
X1 to X4 are the same as or different from each other, and are each independently a group represented by Structural Formula 1 below,
X11 to X14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
a1 to a4 are each an integer of 0 or 1, a1+a2 are an integer of 1 or 2, a3+a4 are an integer of 1 or 2,
a11 and a12 are each an integer from 0 to 5;
a13 and a14 are each an integer from 0 to 4;
When a11 to a14 are integers greater than or equal to 2, the substituents in parentheses are the same as or different from each other;
[Structural Formula 1]

In Structural Formula 1,
Y is O, S or Se;
L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent naphthyl group,
R1 and R2 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or bonded to each other to form a ring,
* means a position binding to Formula 1 above. The compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 11:
[Formula 11]

In Formula 11, X1 to X4, X11 to X14, a1 to a4, and a11 to a14 are as defined in Formula 1 above. The method according to claim 1, X11 and X12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; A substituted or unsubstituted trialkylsilyl group; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
Alkyl of the trialkylsilyl group is a compound that is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. The method according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently deuterium; halogen group; A substituted or unsubstituted alkyl group; and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, substituted or unsubstituted with one or more substituents selected from the group consisting of a substituted or unsubstituted alkoxy group, or a compound that combines with each other to form a substituted or unsubstituted phosphindol. The compound according to claim 1, wherein L is a direct bond or a phenylene group. The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the group consisting of the following compounds:

. An ink composition comprising the compound according to any one of claims 1 to 6. a first electrode;
a second electrode; and
Including one or more organic material layers provided between the first electrode and the second electrode,
At least one layer of the one or more layers of the organic material layer is an organic light emitting device comprising the ink composition of claim 7. The method according to claim 8, wherein the one or more organic material layers include a light emitting layer and one or more first organic material layers,
At least one layer of the one or more first organic material layers includes the ink composition. The organic light emitting device of claim 9, wherein the one or more first organic material layers are provided between the light emitting layer and the second electrode. The method according to claim 9, wherein the one or more first organic material layer is an electron injection layer; electron transport layer; and at least one of an electron injection and transport layer. 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;
The step of forming one or more organic material layers comprises forming an organic material layer using the ink composition of claim 7 . The method of claim 12,
Forming an organic material layer using the ink composition
coating the ink composition on the first electrode or one or more organic layers; and
Method of manufacturing an organic light emitting device comprising a drying step or heat treatment step of the coated ink composition.

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