KR102886634B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light-emitting device using the same.

Description

Novel compound and organic light emitting device comprising the same

The present invention relates to a novel compound and an organic light-emitting device comprising the same.

Organic light-emitting diodes (OLEDs) generally refer to the conversion of electrical energy into light energy using organic materials. Organic light-emitting devices utilizing this phenomenon boast a wide viewing angle, excellent contrast, and fast response times, and are actively researched due to their superior brightness, operating voltage, and response speed characteristics.

Organic light-emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices such as the above.

Meanwhile, organic light-emitting devices are being developed using solution processes, particularly inkjet processes, instead of conventional deposition processes to reduce manufacturing costs. Initially, attempts were made to develop organic light-emitting devices by coating all layers using solution processes. However, current technology has limitations. Therefore, research is underway on a hybrid process that utilizes solution processes for HIL, HTL, and EML, with future processes utilizing conventional deposition processes.

Accordingly, the present invention provides a novel organic light-emitting device material that can be used in an organic light-emitting device and at the same time can be used in a solution process.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel compound and an organic light-emitting device comprising the same.

The present invention provides a compound represented by the following chemical formula 1:

[Chemical Formula 1]

In the above chemical formula 1,

Q is a divalent substituent represented by any one of the following chemical formulas 1a to 1d,

L ₁ to L ₄ are each independently a single bond; or a substituted or unsubstituted C _6-60 arylene,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl,

However, excluding the case where both Ar ₁ and Ar ₂ are unsubstituted phenyl,

When Q is a divalent substituent represented by the above chemical formula 1d, at least one of L ₁ and L ₂ is a substituted or unsubstituted C _6-60 arylene.

In addition, the present invention provides an organic light-emitting device including a first electrode; a second electrode provided opposite the first electrode; and a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer includes a compound represented by the chemical formula 1.

The compound represented by the above-described chemical formula 1 can be used as a material of an organic layer of an organic light-emitting device, and can also be used in a solution process, and can improve efficiency and lifespan characteristics in an organic light-emitting device.

Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4).
Figure 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron injection and transport layer (7), and a cathode (4).

Hereinafter, the present invention will be described in more detail to help understand it.

(Definition of terms)

In this specification, and means a bond that connects to another substituent.

The term "substituted or unsubstituted" as used herein means a group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylphosphine group; or a heteroaryl containing at least one of N, O, and S atoms, or a group unsubstituted or substituted with a substituent in which two or more of the above-mentioned substituents are linked. For example, the "substituent linked with two or more substituents" may be a biphenyl group. That is, the biphenyl group can be an aryl group or can be interpreted as a substituent in which two phenyl groups are connected.

In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may have the oxygen of the ester group replaced by a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.

In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc.

In this specification, the boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, etc.

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, Examples include, but are not limited to, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenylyl group, a terphenylyl group, and the like. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a benzofluorenyl group, and the like.

In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted, etc. However, it is not limited thereto. In addition, the benzofluorenyl group may be substituted like the above fluorenyl group, or two of them may be combined with each other to form a spiro structure.

In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, Examples thereof include, but are not limited to, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group.

In this specification, the aryl group among the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group is the same as the example of the aryl group described above. In this specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In this specification, the heteroaryl among the heteroarylamine may be applied with the description of the heteroaryl described above. In this specification, the alkenyl group among the aralkenyl group is the same as the example of the alkenyl group described above. In this specification, the description of the aryl group described above may be applied with the exception that arylene is a divalent group. In this specification, the description of the heteroaryl described above may be applied with the exception that heteroarylene is a divalent group.

(compound)

The present invention provides a compound represented by the above chemical formula 1.

The compound represented by the above chemical formula 1 is a compound having a structure in which two anthracenes are connected by a naphthylene linker (Q). At this time, the naphthylene linker is 1,2-naphthylene (chemical formula 1a), 1,8-naphthylene (chemical formula 1b), 2,3-naphthylene (chemical formula 1c), or 2,7-naphthylene (chemical formula 1d), and the compound is characterized in that, when the naphthylene linker (Q) is 2,7-naphthylene, which is a divalent substituent represented by the above chemical formula 1d, at least one of the 2nd and 7th positions of the 2,7-naphthylene is connected by anthracene and a C _6-60 arylene. In addition, in the above chemical formula 1, Ar ₁ and Ar ₂ are not simultaneously unsubstituted phenyl.

An organic light-emitting device employing a compound represented by the above chemical formula 1 can exhibit high efficiency and long life characteristics compared to an organic light-emitting device employing i) a compound in which the naphthylene linker (Q) is a divalent substituent represented by the above chemical formula 1d and both L ₁ and L ₂ are single bonds and ii) a compound in which Ar ₁ and Ar ₂ are both unsubstituted phenyl.

In addition, the compound represented by the above chemical formula 1 has high solubility in organic solvents used in solution processes, such as cyclohexanone, and is therefore suitable for use in large-area solution processes such as inkjet coating methods that use solvents with high boiling points.

Meanwhile, the compound may be represented by any one of the following chemical formulas 1-A to 1-D:

[Chemical Formula 1-A]

[Chemical Formula 1-B]

[Chemical Formula 1-C]

[Chemical Formula 1-D]

In the above chemical formulas 1-A to 1-D,

L ₁ to L ₄ , Ar ₁ and Ar ₂ are as defined in the above chemical formula 1.

Additionally, in the above chemical formula 1, L ₁ and L ₂ may each independently be a single bond or C _6-20 arylene.

Specifically, one of L ₁ and L ₂ may be C _6-20 arylene, and the other may be a single bond or C _6-20 arylene.

More specifically, one of L ₁ and L ₂ may be any one selected from the group consisting of: and the other may be a single bond, or any one selected from the group consisting of:

.

At this time, L ₁ and L ₂ may be identical to each other. Alternatively, L ₁ and L ₂ may be different.

For example, one of L ₁ and L ₂ is phenylene and the other is a single bond; or

One of L ₁ and L ₂ is phenylene and the other is biphenyldiyl; or

Both L ₁ and L ₂ are phenylene; or

Both L ₁ and L ₂ can be biphenyldiyl.

Also, for example, one of L ₁ and L ₂ and the other is a single bond;

Either L ₁ or L ₂ and the other is a single bond;

Either L ₁ or L ₂ and the other one is This or;

Either L ₁ or L ₂ and the other one is This or;

Either L ₁ or L ₂ and the other one is This or;

Both L ₁ and L ₂ This or;

Both L ₁ and L ₂ Either; or

Both L ₁ and L ₂ It could be.

Additionally, in the above chemical formula 1, L ₃ and L ₄ may each independently be a single bond or C _6-20 arylene.

Specifically, L ₃ and L ₄ can each independently be a single bond or phenylene.

At this time, L ₃ and L ₄ may be the same. Alternatively, L ₃ and L ₄ may be different.

More specifically, both L ₃ and L ₄ are single bonds;

One of L ₃ and L ₄ is a single bond and the other is phenylene; or

Both L ₃ and L ₄ can be phenylene.

For example, both L ₃ and L ₄ are single bonds;

One of L ₃ and L ₄ is a single bond and the other is 1,3-phenylene or 1,4-phenylene; or

One of L ₃ and L ₄ is 1,3-phenylene and the other is 1,4-phenylene; or

L ₃ and L ₄ are both 1,3-phenylene; or

Both L ₃ and L ₄ can be 1,4-phenylene.

In other words, both L ₃ and L ₄ are single bonds;

One of L ₃ and L ₄ is a single bond, and the other is This or;

One of L ₃ and L ₄ is a single bond, and the other is This or;

Either L ₃ or L ₄ and the other one is This or;

Both L ₃ and L ₄ Either; or

Both L ₃ and L ₄ It could be.

In addition, in the above chemical formula 1, Ar ₁ and Ar ₂ may each independently be unsubstituted or C _6-20 aryl substituted with one or more C _1-10 alkyl. However, Ar ₁ and Ar ₂ are not simultaneously unsubstituted phenyl.

Specifically, Ar ₁ and Ar ₂ can each independently be phenyl, which is unsubstituted or substituted with 1 to 5 C _1-10 alkyl; or naphthyl, which is unsubstituted or substituted with 1 to 7 C _1-10 alkyl.

More specifically, Ar ₁ and Ar ₂ may each independently be phenyl, which is unsubstituted or substituted with 1 to 5 C _1-10 alkyls each independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl and tert-butyl; or naphthyl, which is unsubstituted or substituted with 1 to 7 C _1-10 alkyls each independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl and tert-butyl.

At this time, Ar ₁ and Ar ₂ may be the same. Alternatively, Ar ₁ and Ar ₂ may be different.

Additionally, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of:

.

However, both Ar ₁ and Ar ₂ It is not.

Also, one of Ar ₁ and Ar ₂ and the other is any one selected from the group consisting of; or

One of Ar ₁ and Ar ₂ is selected from the group consisting of:

The other may be any one selected from the group consisting of:

.

Also preferably, both Ar ₁ and Ar ₂ This or;

One of Ar ₁ and Ar ₂ and the other one is Either; or

Both Ar ₁ and Ar ₂ It could be.

Representative examples of compounds represented by the above chemical formula 1 are as follows:

.

Meanwhile, the compound represented by the above chemical formula 1 can be manufactured by a manufacturing method such as the following reaction scheme 1, for example.

[Reaction Formula 1]

In the above reaction scheme 1, the definition of each substituent is as described above.

Specifically, the compound represented by the above chemical formula 1 can be prepared through step a and step b.

First, the above step a is a step of preparing compound 1-2 by introducing a -OTf (-O ₃ SCF ₃ ) group, which is a reactive group for Suzuki coupling reaction, into compound 1-1 using Tf ₂ O (Trifluoromethanesulfonic anhydride).

Next, step b is a step for preparing a compound represented by the above chemical formula 1 through a Suzuki coupling reaction of compounds 1-2 and 1-3. This Suzuki coupling reaction is preferably performed in the presence of a palladium catalyst and a base, respectively. In addition, the reactor for the Suzuki coupling reaction may be appropriately modified, and the method for preparing the compound represented by the above chemical formula 1 may be further specified in the manufacturing examples described below.

(Coating composition)

Meanwhile, the compound according to the present invention can form an organic layer, particularly a light-emitting layer, of an organic light-emitting device through a solution process. Specifically, the compound can be used as a host material for the light-emitting layer. To this end, the present invention provides a coating composition comprising the compound according to the present invention and a solvent.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and examples thereof include chlorine solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, etc.; ether solvents such as tetrahydrofuran, dioxane, etc.; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, mesitylene, 1-methylnaphthalene, 2-methylnaphthalene, etc.; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, etc.; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, etc.; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, etc. Examples thereof include polyhydric alcohols and their derivatives, 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; 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; benzoate solvents, such as butyl benzoate, methyl-2-methoxybenzoate, and ethyl benzoate; phthalate solvents, such as dimethyl phthalate, diethyl phthalate, and diphenyl phthalate; tetralin; and solvents, such as 3-phenoxytoluene. Additionally, the above-described solvents may be used alone or in combination of two or more solvents. Preferably, cyclohexanone may be used as the solvent.

In addition, the coating composition may further include a compound used as a dopant material, and a description of the compound used in the host material will be described below.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. In addition, the concentration of the compound according to the present invention in the coating composition may be 0.1 wt/vol% to 20 wt/vol%.

In addition, the solubility (wt%) of the compound represented by the above chemical formula 1 at room temperature/normal pressure may be 0.1 wt% or more, more specifically 0.1 wt% to 5 wt%, based on the solvent cyclohexanone. Accordingly, a coating composition comprising the compound represented by the above chemical formula 1 and the solvent may be used in a solution process.

The present invention also provides a method for forming a light-emitting layer using the above-described coating composition. Specifically, the method comprises the steps of coating the light-emitting layer according to the present invention described above on an anode or on a hole transport layer formed on the anode using a solution process; and the step of heat-treating the coated coating composition.

The above solution process uses the coating composition according to the present invention described above, and means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

In the above heat treatment step, the heat treatment temperature is preferably 150 to 230°C. In addition, the heat treatment time is preferably 1 minute to 3 hours, and more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

(organic light emitting device)

In addition, the present invention provides an organic light-emitting device comprising a compound represented by the above chemical formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer comprises a compound represented by the above chemical formula 1.

In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate, where the first electrode is an anode and the second electrode is a cathode. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially laminated on a substrate, where the first electrode is a cathode and the second electrode is an anode. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

Figure 1 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). In such a structure, the compound represented by the chemical formula 1 may be included in the light-emitting layer.

Figure 2 illustrates an example of an organic light-emitting device composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron injection and transport layer (7), and a cathode (4). In such a structure, the compound represented by the chemical formula 1 may be included in the light-emitting layer.

The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that the light-emitting layer comprises the compound according to the present invention and is manufactured using the method described above.

For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon.

In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited to this.

For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

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

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

The above-mentioned hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect at the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and has excellent thin film forming ability. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene.

The above hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. A hole transport material that can transport holes from the anode or the hole injection layer and move them to the light-emitting layer and has high hole mobility is suitable. The hole transport material may be a compound represented by the above chemical formula 1, or an arylamine-based organic material, a conductive polymer, or a block copolymer having both a conjugated portion and a non-conjugated portion, but is not limited thereto.

Meanwhile, the organic light-emitting device may include an electron blocking layer between the hole transport layer and the light-emitting layer. The electron blocking layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and refers to a layer that controls hole mobility, prevents excessive movement of electrons, and increases the probability of hole-electron coupling, thereby improving the efficiency of the organic light-emitting device. The electron blocking layer includes an electron blocking material, and examples of such an electron blocking material include, but are not limited to, a compound represented by the above chemical formula 1, or an arylamine-based organic material.

The above-described light-emitting layer may include a host material and a dopant material. A compound represented by the above chemical formula 1 may be used as the host material. In addition, a fused aromatic ring derivative or a heterocyclic compound may be used together with the compound represented by the above chemical formula 1 as the host material. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic compound includes, but is not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like.

In addition, dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and styrylamine compounds are compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one 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, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

Meanwhile, the organic light-emitting device may include a hole-blocking layer between the light-emitting layer and the electron transport layer. The hole-blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and refers to a layer that improves the efficiency of the organic light-emitting device by controlling electron mobility, preventing excessive movement of holes, and increasing the probability of hole-electron coupling. The hole-blocking layer includes a hole-blocking material, and examples of such hole-blocking materials include, but are not limited to, compounds having an electron-withdrawing group introduced therein, such as azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; and phosphine oxide derivatives.

The above electron injection and transport layer is a layer that simultaneously functions as an electron transport layer and an electron injection layer that injects electrons from an electrode and transports the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole-blocking layer. As the electron injection and transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples of the electron injection and transport material include, but are not limited to, an Al complex of 8-hydroxyquinoline; a complex containing Alq ₃ ; an organic radical compound; a hydroxyflavone-metal complex; and a triazine derivative. Alternatively, it may be used with, but is not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, or nitrogen-containing 5-membered ring derivatives.

The above electron injection and transport layer may also be formed as separate layers, such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron injection layer. In addition, the electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer may be LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

The above metal complex compounds 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

In addition, the compound according to the present invention can be included in an organic solar cell or an organic transistor in addition to an organic light-emitting device.

The manufacture of the compound represented by the above chemical formula 1 and the organic light-emitting device containing the same is specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

Manufacturing Example 1: Preparation of Compound B1

Compound 1-a (1 g, 1.0 eq.) and compound 1-b (2.1 eq.) were placed in a round-bottomed flask and dissolved in PhMe. C ₂ CO ₃ (10 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (20 mol%) was added dropwise at a bath temperature of 90°C and stirred for 3 days. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, washed with EtOAc/brine, and the organic layer was separated. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound B1 (86% yield).

m/z [M+H] ⁺ = 885.3

Manufacturing Example 2: Preparation of Compound B4

Step 2-1) Preparation of compound 2-a

Compound 1-a (3 g, 1.0 eq.) and compound 1-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, washed with EtOAc/brine, and the organic layer was separated. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 2-a (83% yield).

m/z [M+H] ⁺ = 585.1

Step 2-2) Preparation of compound B4

Compound 2-a (1 g, 1.0 eq.) and compound 2-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, washed with EtOAc/brine, and the organic layer was separated. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound B4 (85% yield).

m/z [M+H] ⁺ = 585.1

Manufacturing Example 3: Preparation of Compound B10

Compound B10 (87% yield) was prepared in the same manner as compound B4 except that compound 3-a was used instead of compound 2-b.

m/z [M+H] ⁺ = 961.4

Manufacturing Example 4: Preparation of Compound B3

Compound B3 (82% yield) was prepared in the same manner as compound B4 except that compound 4-a was used instead of compound 2-b.

m/z [M+H] ⁺ = 961.4

Manufacturing Example 5: Preparation of Compound A1

Step 5-1) Preparation of compound 5-c

Compound 5-a (10.0 g, 1.0 eq.) and compound 5-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred for 2 days. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, and washed with EtOAc/brine to separate the organic layer. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 5-c (97% yield).

m/z [M+H] ⁺ = 447.2

Step 5-2) Preparation of compound 5-d

Compound 5-c (12.0 g, 1.0 eq.) was placed in a round-bottom flask and dissolved _in anhydrous _CH2Cl2 . Pyridine (2.0 eq.) was then added dropwise at room temperature, and the bath temperature was lowered to 0°C and stirred for 10 minutes. _Tf2O (1.2 eq.) dissolved _in anhydrous _CH2Cl2 was slowly added dropwise to the mixture using a dropping funnel, and the bath temperature was gradually increased from 0°C to room temperature and stirred overnight. After the reaction, the reactant was sufficiently diluted _{in CH2Cl2} and washed with _CH2Cl2 / _brine to separate the organic layer. The water was removed with _MgSO4 and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 5-d (98% yield).

m/z [M+H] ⁺ = 579.1

Step 5-3) Preparation of compound A1

Compound 5-a (2.0 g, 1.0 eq.) and compound 1-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred for 2 days. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, and washed with EtOAc/brine to separate the organic layer. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound A1 (92% yield).

m/z [M+H] ⁺ = 809.3

Manufacturing Example 6: Preparation of Compound A2

Compound A2 (96% yield) was prepared in the same manner as compound A1 except that compound 2-b was used instead of compound 1-b.

m/z [M+H] ⁺ = 809.3

Manufacturing Example 7: Preparation of Compound A4

Compound 7-a (2.0 g, 1.0 eq.) and compound 4-a (2.4 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (10 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (20 mol%) was added dropwise at a bath temperature of 90°C and stirred for 2 days. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, washed with EtOAc/brine, and the organic layer was separated. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound A4 (83% yield).

m/z [M+H] ⁺ = 1037.4

Manufacturing Example 8: Preparation of Compound A3

Compound A3 (yield 87%) was prepared in the same manner as compound A4 except that compound 2-b was used instead of compound 4-a.

m/z [M+H] ⁺ = 885.3

Manufacturing Example 9: Preparation of Compound C1

Compound 9-a (2.0 g, 1.0 eq.) and compound 1-b (2.4 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (10 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (20 mol%) was added dropwise at a bath temperature of 90°C and stirred for 2 days. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, and washed with EtOAc/brine to separate the organic layer. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound C1 (83% yield).

m/z [M+H] ⁺ = 885.3

Manufacturing Example 10: Preparation of Compound C2

Step 10-1) Preparation of compound 10-a

Compound 9-a (10.0 g, 1.0 eq.) and compound 1-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, and washed with EtOAc/brine to separate the organic layer. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 10-a (91% yield).

m/z [M+H] ⁺ = 585.1

Step 10-2) Preparation of compound C2

Compound 10-a (2.0 g, 1.0 eq.) and compound 2-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, and washed with EtOAc/brine to separate the organic layer. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound C2 (87% yield).

m/z [M+H] ⁺ = 885.3

Manufacturing Example 11: Preparation of Compound C3

Compound C3 (91% yield) was prepared in the same manner as compound C2 except that compound 11-a was used instead of compound 2-b.

m/z [M+H] ⁺ = 835.3

Manufacturing Example 12: Preparation of Compound C4

Compound C4 (85% yield) was prepared in the same manner as compound C2 except that compound 3-a was used instead of compound 2-b.

m/z [M+H] ⁺ = 961.4

Manufacturing Example 13: Preparation of Compound D1

Compound 13-a (2.0 g, 1.0 eq.) and compound 1-b (2.4 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (10 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (20 mol%) was added dropwise at a bath temperature of 90°C and stirred for 2 days. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, washed with EtOAc/brine, and the organic layer was separated. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound D1 (91% yield).

m/z [M+H] ⁺ = 885.3

Manufacturing Example 14: Preparation of Compound D2

Step 14-1) Preparation of compound 14-a

Compound 13-a (2.0 g, 1.0 eq.) and compound 1-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, washed with EtOAc/brine, and the organic layer was separated. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 14-a (91% yield).

m/z [M+H] ⁺ = 585.1

Step 14-2) Preparation of compound D2

Compound 14-a (2.0 g, 1.0 eq.) and compound 2-b (1.03 eq.) were placed in a round-bottomed flask and dissolved in anhydrous PhMe. C ₂ CO ₃ (5 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise at a bath temperature of 90°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, diluted sufficiently with EtOAc, washed with EtOAc/brine, and the organic layer was separated. The water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed-through solution was concentrated under reduced pressure and purified by column chromatography to prepare compound D2 (89% yield).

m/z [M+H] ⁺ = 885.3

Manufacturing Example 15: Preparation of Compound D4

Compound D4 (89% yield) was prepared in the same manner as compound D2 except that compound 3-a was used instead of compound 2-b.

m/z [M+H] ⁺ = 961.4

Manufacturing Example 16: Preparation of Compound D3

Compound D3 (89% yield) was prepared in the same manner as compound D1 except that compound 16-a was used instead of compound 1-b.

m/z [M+H] ⁺ = 885.3

Comparative Manufacturing Example 1: Preparation of Comparative Compound X1

Compound X1 (78% yield) was prepared in the same manner as compound B1 except that compound 11-a was used instead of compound 1-b.

m/z [M+H] ⁺ = 785.3

Comparative Manufacturing Example 2: Preparation of Comparative Compound X2

Compound X2 (92% yield) was prepared in the same manner as compound D1 except that compound 5-b was used instead of compound 1-b.

m/z [M+H] ⁺ = 733.3

Comparative Manufacturing Example 3: Preparation of Comparative Compound X3

Compound X3 (90% yield) was prepared in the same manner as compound X2 except that compound C-a was used instead of compound 5-b.

m/z [M+H] ⁺ = 733.3

Example 1: Fabrication of an organic light-emitting device

Example 1

A glass substrate coated with a 500 Å thick ITO (indium tin oxide) film was placed in distilled water containing a detergent and ultrasonically cleaned. The detergent used was a Fischer Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, the substrate was ultrasonically cleaned with a solvent of isopropyl and acetone, dried, and then washed for 5 minutes before being transported to a glove box.

On the ITO transparent electrode, a coating composition containing the compound p-dopant and the compound HIL (weight ratio of 2:8) dissolved in cyclohexanone at 20 wt/v% was spin-coated (4000 rpm) and heat-treated (cured) at 200° C. for 30 minutes to form a hole injection layer with a thickness of 400 Å.

A coating composition containing the compound HTL (Mn: 27,900; Mw: 35,600; measured by GPC using PC Standard using Agilent 1200 series) dissolved in toluene at 6 wt/v% was spin-coated (4000 rpm) on the hole injection layer and heat-treated at 200° C. for 30 minutes to form a hole transport layer with a thickness of 200 Å.

On the hole transport layer, a coating composition in which the light-emitting layer host compound B1 prepared in Manufacturing Example 1 and the light-emitting layer dopant compound Dopant (weight ratio of 98:2) were dissolved in cyclohexanone at 2 wt/v% was spin-coated (4000 rpm) and heat-treated at 180°C for 30 minutes to form a light-emitting layer with a thickness of 400 Å.

After transferring to a vacuum deposition machine, the compound ETL was vacuum-deposited to a thickness of 350 Å on the light-emitting layer to form an electron injection and transport layer. LiF was sequentially deposited to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, LiF at 0.3 Å/sec, and aluminum at 2 Å/sec, and the vacuum during deposition was maintained at 2*10 ^-7 to 5*10 ^-8 torr.

Examples 2 to 16

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of Compound B1 as the host of the light-emitting layer. The compounds used in the examples are summarized as follows.

Comparative Examples 1 to 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of Compound B1 as the host of the light-emitting layer. At this time, the compounds used in the comparative example are as follows.

[Experimental Example]

Experimental Example 1: Characteristic Evaluation of Organic Light-Emitting Diodes

When current was applied to the organic light-emitting devices manufactured in the above examples and comparative examples, the results of measuring the driving voltage, external quantum efficiency (EQE), and lifespan at a current density of 10 mA/cm ² are shown in Table 1 below. At this time, the external quantum efficiency (EQE) was calculated as “(number of emitted photons)/(number of injected charge carriers)*100,” and T90 means the time required for the luminance to decrease from the initial luminance (500 nit) to 90%.

division luminescent layer
Host Driving voltage
(V @10mA/cm ² ) EQE
(% @10mA/cm ² ) Lifespan (hr)
(T90 @500 nit) Example 1 Compound B1 4.65 7.58 198 Example 2 Compound B4 4.67 7.54 201 Example 3 Compound B10 4.68 7.51 199 Example 4 Compound B3 4.62 7.62 200 Example 5 Compound A1 4.65 7.59 205 Example 6 Compound A2 4.68 7.53 203 Example 7 Compound A4 4.68 7.60 207 Example 8 Compound A3 4.62 7.58 199 Example 9 Compound C1 4.67 7.60 201 Example 10 Compound C2 4.68 7.56 203 Example 11 Compound C3 4.65 7.60 198 Example 12 Compound C4 4.67 7.61 206 Example 13 Compound D1 4.62 7.62 200 Example 14 Compound D2 4.59 7.62 202 Example 15 Compound D4 4.60 7.59 201 Example 16 Compound D3 4.61 7.61 198 Comparative Example 1 Compound X1 4.66 4.62 42 Comparative Example 2 Compound X2 4.65 4.59 45 Comparative Example 3 Compound X3 4.62 4.58 37

As shown in Table 1 above, it can be seen that the organic light-emitting device of the example using the compound represented by the chemical formula 1 as the host material of the light-emitting layer exhibits superior characteristics in terms of driving voltage and stability compared to the organic light-emitting device of the comparative example.

Specifically, the organic light-emitting device of the example using the compound represented by the above chemical formula 1 as a host for the light-emitting layer exhibited higher efficiency and significantly longer lifespan compared _to the organic light-emitting devices of Comparative Examples 1 to 3 using Comparative Compound X1, wherein both Ar ₁ and Ar ₂ in the above chemical formula 1 are unsubstituted phenyl, and Comparative Compounds X2 and X3 _, wherein in the above chemical formula 1, Q is a divalent substituent represented by the above chemical formula 1d and both L 1 and L 2 are single bonds, as hosts for the light-emitting layer. This means that, considering that the light-emitting efficiency and lifespan characteristics of organic light-emitting devices generally have a trade-off relationship, the organic light-emitting device employing the compound of the present invention exhibits significantly improved device characteristics compared to the comparative example device.

1: Substrate 2: Anode
3: Emitting layer 4: Cathode
5: Hole injection layer 6: Hole transport layer
7: Electron injection and transport layer

Claims (10)

A compound represented by the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
Q is a divalent substituent represented by any one of the following chemical formulas 1a to 1d,

L ₁ and L ₂ are each independently a single bond; or a substituted or unsubstituted monocyclic arylene,
L ₃ and L ₄ are each independently a single bond; or a substituted or unsubstituted C _6-20 arylene,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-20 aryl,
However, excluding the case where both Ar ₁ and Ar ₂ are unsubstituted phenyl,
When Q is a divalent substituent represented by the above chemical formula 1d, at least one of L ₁ and L ₂ is a substituted or unsubstituted monocyclic arylene,
Here, the monocyclic arylene is phenylene, biphenyldiyl, or terphenyldiyl, and “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen; alkyl; and aryl, or substituted or unsubstituted with a substituent in which two or more of the substituents exemplified above are connected.
Regarding paragraph 1,
The compound is represented by any one of the following chemical formulas 1-A to 1-D:
compound:
[Chemical Formula 1-A]

[Chemical Formula 1-B]

[Chemical Formula 1-C]

[Chemical Formula 1-D]

In the above chemical formulas 1-A to 1-D,
L ₁ to L ₄ , Ar ₁ and Ar ₂ are as defined in paragraph 1.
Regarding paragraph 1,
One of L ₁ and L ₂ is any one selected from the group consisting of the following, and the other is a single bond, or any one selected from the group consisting of the following,
compound:
.
Regarding paragraph 1,
One of L ₁ and L ₂ is phenylene and the other is a single bond; or
One of L ₁ and L ₂ is phenylene and the other is biphenyldiyl; or
Both L ₁ and L ₂ are phenylene; or
Both L ₁ and L ₂ are biphenyldiyl,
compound.
Regarding paragraph 1,
L ₃ and L ₄ are each independently a single bond, or phenylene,
compound.
Regarding paragraph 1,
L ₃ and L ₄ are both single bonds; or
One of L ₃ and L ₄ is a single bond and the other is 1,3-phenylene or 1,4-phenylene; or
One of L ₃ and L ₄ is 1,3-phenylene and the other is 1,4-phenylene; or
L ₃ and L ₄ are both 1,3-phenylene; or
L ₃ and L ₄ are both 1,4-phenylene,
compound.
Regarding paragraph 1,
One of Ar ₁ and Ar ₂ is unsubstituted or substituted naphthyl with 1 to 5 C _1-10 alkyl, and the other is unsubstituted or substituted phenyl with 1 to 5 C _1-10 alkyl; or unsubstituted or substituted naphthyl with 1 to 7 C _1-10 alkyl; or
One of Ar ₁ and Ar ₂ is phenyl substituted with 1 to 5 C _1-10 alkyl, and the other is phenyl unsubstituted or substituted with 1 to 5 C _1-10 alkyl; or naphthyl unsubstituted or substituted with 1 to 7 C _1-10 alkyl,
compound.
Regarding paragraph 1,
Ar ₁ and Ar ₂ are each independently one selected from the group consisting of:
compound:
.
Regarding paragraph 1,
The above compound is any one selected from the group consisting of the following compounds:
compound:













.
An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer comprises a compound according to any one of claims 1 to 9.