KR20230115734A - 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. The compound represented by a chemical formula 1 can be used as a material for an organic layer of the organic light-emitting device, can also be used in a solution process, and can improve efficiency and lifespan characteristics of the organic light-emitting device.

Description

Novel compound and organic light emitting device using the same

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, 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 this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.

Meanwhile, in recent years, an organic light emitting device using a solution process, particularly an inkjet process, instead of a conventional deposition process has been developed to reduce process costs. In the early days, an attempt was made to develop an organic light emitting device by coating all organic light emitting device layers with a solution process, but current technology has limitations, so only HIL, HTL, and EML are processed as a solution process, and the subsequent process is a hybrid that utilizes the existing deposition process. (hybrid) process is under investigation.

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

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

D means deuterium,

P ₁ and P ₂ are each independently a single bond; or phenylene which is unsubstituted or substituted with deuterium;

Q ₁ and Q ₂ are each independently unsubstituted or deuterium-substituted naphthylene,

L ₁ to L ₄ are each independently a single bond; phenylene unsubstituted or substituted with deuterium; or naphthylene unsubstituted or substituted with deuterium;

Ar ₁ and Ar ₂ are each independently unsubstituted or deuterium-substituted phenyl; or naphthyl unsubstituted or substituted with deuterium;

x, y and z are each independently an integer from 0 to 8;

provided that the compound contains at least one deuterium.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. .

The compound represented by Formula 1 described above can be used as a material for an organic layer of an organic light emitting device, and can also be used in a solution process, and can improve efficiency and lifetime characteristics of an organic light emitting device.

1 shows 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.
2 is 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). is shown.

Hereinafter, in order to aid understanding of the present invention, it will be described in more detail.

(Definition of Terms)

In this specification, and means a bond connected to another substituent, and D means deuterium.

As used herein, the term “substituted or unsubstituted” refers to heavy hydrogen, 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 alkyl Thioxy group, arylthioxy group, alkylsulfoxyl group, arylsulfoxyl group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine substituted or unsubstituted with one or more substituents selected from the group consisting of a group, a heteroarylamine group, an arylamine group, an arylphosphine group, or a heteroaryl containing at least one of N, O, and S atoms; It means that two or more substituents among the substituents exemplified above are linked to each other, substituted or unsubstituted. 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 or may be interpreted as a substituent in which two phenyl groups are connected. For example, the term “substituted or unsubstituted” means “unsubstituted or one or more selected from the group consisting of deuterium, halogen, C _1-10 alkyl, C _1-10 alkoxy and C _6-20 aryl. , for example, substituted with 1 to 5 substituents". In addition, the term "substituted with one or more substituents" in this specification will be understood to mean, for example, "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents". can

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

In the present specification, the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. Specifically, it may be a substituent of the following structural formula, but is not limited thereto.

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

In the present specification, the silyl group is specifically 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, and the like. but not limited to

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

In this specification, examples of the halogen group include fluoro, chloro, bromo, or iodo.

In the present specification, the alkyl group may be straight-chain or branched-chain, 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 exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5 -methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4- trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc., but is not limited thereto.

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 alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include 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, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 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. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, 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, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. 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, triphenylenyl group, pyrenyl group, perylenyl group, chrysenyl group, etc., but is not limited thereto.

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

In the present specification, an aralkyl group, an aralkenyl group, an alkylaryl group, an arylamine group, and an aryl group among arylsilyl groups are the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the above-mentioned alkyl group. In the present specification, the description of the above-described heteroaryl may be applied to the heteroaryl among heteroarylamines. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of heteroaryl described above may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.

In this specification, the term "deuterated or substituted with deuterium" means that at least one available hydrogen in each formula is replaced with deuterium. Specifically, substituting with deuterium in each chemical formula or definition of a substituent means that at least one of hydrogen-bonding positions in a molecule is substituted with deuterium.

In addition, in the present specification, the term "deuterium substitution rate" means the percentage of the number of deuterium substituted with respect to the total number of hydrogens that may be present in each chemical formula.

(compound)

The present invention provides a compound represented by Formula 1 above.

Specifically,

In Formula 1,

P ₁ and P ₂ are each independently a single bond; or phenylene unsubstituted or substituted with 1 to 4 deuterium atoms;

Q ₁ and Q ₂ are each independently unsubstituted or 1 to 6 deuterium-substituted naphthylene,

L ₁ to L ₄ are each independently a single bond; phenylene unsubstituted or substituted with 1 to 4 deuterium; or naphthylene unsubstituted or substituted with 1 to 6 deuterium atoms;

Ar ₁ and Ar ₂ are each independently phenyl unsubstituted or substituted with 1 to 5 deuterium atoms; or naphthyl unsubstituted or substituted with 1 to 7 deuterium atoms;

x, y and z are each independently an integer from 0 to 8;

provided that the compound contains at least one deuterium.

The compound represented by Formula 1 is a compound having a structure in which three 9,10-anthracenylenes are connected by two naphthylene linkers, and the compound contains at least one deuterium.

Here, "the compound contains at least one deuterium" means that at least one hydrogen in the compound molecule is substituted with a deuterium, and more specifically, the compound has one or more of the following 1) to 5) means that the case is satisfied:

1) x+y+z is greater than or equal to 1;

2) at least one of P ₁ and P ₂ is phenylene substituted with one or more deuterium;

3) at least one of Q ₁ and Q ₂ is naphthylene substituted with one or more deuterium;

4) phenylene in which at least one of L ₁ to L ₄ is substituted with one or more deuterium; or naphthylene substituted with one or more deuterium; or

5) phenyl in which at least one of Ar ₁ and Ar ₂ is substituted with one or more deuterium; or naphthyl substituted with one or more deuterium.

As such, a compound containing at least one deuterium in the compound has a stronger bond energy in the molecule than a compound not substituted with deuterium because the bond energy of the C-D bond is greater than that of the C-H bond. and, accordingly, material stability may be increased. Therefore, the compound represented by Chemical Formula 1 can improve the efficiency and stability of the organic light emitting device compared to a compound having a structure not substituted with deuterium.

Alternatively, Formula 1 may be represented by the following Formula 1D:

[Formula 1D]

In Formula 1D,

n means the number of deuterium substitutions in the compound,

P' ₁ and P' ₂ are each independently a single bond; or phenylene;

Q' ₁ and Q' ₂ are each independently naphthylene;

L' ₁ to L' ₄ are each independently a single bond; phenylene; or naphthylene;

Ar' ₁ and Ar' ₂ are each independently phenyl; or naphthyl;

However, n is 1 or more.

(In other words, P' ₁ , P' ₂ , Q' ₁ , Q' ₂ , L' ₁ to L' ₄ , Ar' ₁ and Ar' ₂ are respectively P ₁ , P ₂ , Q ₁ , Q ₂ , L ₁ to L ₄ , Ar ₁ and Ar ₂ mean non-deuterated substituents)

Specifically, the deuterium substitution rate of the compound may be 50% to 100%. Specifically, the deuterium substitution rate of the compound is 60% or more, 70% or more, 80% or more, 85% or more, 88% or more, 90% or more, 91% or more, 92% or more, 92.5% or more, 93% or more , may be 100% or less. The deuterium substitution rate of these compounds is calculated as the number of substituted deuteriums relative to the total number of hydrogens that may exist in the formula. Spectrometer) analysis.

At this time, in order for a compound having a specific structure to exhibit an effect of increasing intramolecular binding energy and improving material stability according to deuterium substitution, the higher the deuterium substitution rate of the compound, the better. Therefore, preferably, the deuterium substitution rate of the compound is 80% or more.

Therefore, the deuterium substitution rate of the compound represented by Formula 1D can be calculated by the following Formula 1, and preferably the value of Formula 1 is 80% or more.

[Equation 1]

Deuterium substitution rate (%) = [number of deuterium substituted (n) / total number of hydrogens that can be substituted with deuterium present in the formula] * 100

In particular, since at least one hydrogen in the anthracenylene moiety must be substituted with deuterium in order for the compound to exhibit a deuterium substitution rate of 80% or more, the case where at least one of the three anthracenylene hydrogens is substituted with deuterium is described above. The compound may be suitable for exhibiting an effect of improving device characteristics according to deuterium substitution.

Accordingly, in Chemical Formula 1, x+y+z may be 1 or more.

In other words, a, b, and c are each independently 0, 1, 2, 3, 4, 5, 6, 7, or 8, and x+y+z is 1 or more and 24 or less. At this time, a compound in which x+y+z is 24, that is, a compound in which all hydrogens bonded to carbons at positions 1 to 8 of three 9,10-anthracenylene are substituted with deuterium have more C-D bonds in the molecule. , and thus material stability may be higher. Accordingly, the organic light emitting device employing the compound in which x+y+z is 24 in Chemical Formula 1 may have improved efficiency and lifetime characteristics.

For example, each of x, y, and z is 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, or 8 or less.

In addition, P ₁ and P ₂ are single bonds; 1,3-phenylene unsubstituted or substituted with 1 to 4 deuterium; or 1,4-phenylene that is unsubstituted or substituted with 1 to 4 deuterium atoms.

Also, P ₁ and P ₂ may be identical to each other.

In addition, Q ₁ and Q ₂ may be any one of divalent linking groups represented by the following Chemical Formulas 2a to 2j:

In Formulas 2a to 2j,

r is an integer from 1 to 6;

Also, Q ₁ and Q ₂ may be equal to each other.

In addition, L ₁ to L ₄ are each independently a single bond; Or it may be any one of the divalent linking groups represented by Formulas 3a to 3m:

In Formulas 3a to 3m,

s is an integer from 0 to 4;

t is an integer from 0 to 6;

Preferably, in Formulas 3a to 3m,

s is an integer from 1 to 4;

t is an integer from 1 to 6.

Also preferably, L ₁ and L ₂ are each independently a single bond; A divalent linking group represented by Formula 3a; Or a divalent linking group represented by Formula 3b,

Here, s is an integer from 1 to 4.

Also, L ₁ and L ₂ may be the same as each other.

Also preferably, L ₃ and L ₄ are each independently a single bond; A divalent linking group represented by Formula 3a; A divalent linking group represented by Formula 3b; Or a divalent linking group represented by Formula 3i,

Here, s is an integer from 1 to 4, and t is an integer from 1 to 6.

Also, L ₃ and L ₄ may be the same as each other.

In addition, Ar ₁ and Ar ₂ are each independently phenyl substituted with 1 to 5 deuterium atoms; 1-naphthyl substituted with 1 to 7 deuterium; or 2-naphthyl substituted with 1 to 7 deuterium atoms.

및 상기

는 서로 동일할 수 있다.At this time, the

and above

may be equal to each other.

Meanwhile, the compound represented by Formula 1 is any one selected from the group consisting of compounds represented by Formula 1' below:

[Formula 1']

In Formula 1',

n means the number of deuterium substitutions in the compound,

Core is any one selected from divalent linking groups represented by the following formulas Core 1 to Core 44,

R is any one selected from substituents represented by the following formulas R1 to R22,

The compound represented by Formula 1' is as follows,

.

에 대응되고, "R"은

및

에 대응된다.In Formula 1', "Core" is of Formula 1D

Corresponds to, "R" is

and

corresponds to

At this time, the meaning that n in Formula 3-2, which is one of the above compounds, is an integer of 50 to 54, means that 50 to 54 of Z in the following compound 3-2' are deuterium, and the remaining Z other than deuterium is hydrogen. means that

.

.

및

가 서로 동일한 경우 하기 반응식 1과 같은 제조 방법으로 제조할 수 있다: On the other hand, the compound represented by Formula 1 is, for example,

and

When are the same as each other, it can be prepared by the manufacturing method shown in Scheme 1 below:

[Scheme 1]

In Scheme 1, P' ₁ , P' ₂ , Q' ₁ , Q' ₂ , L' ₁ , L' ₃ and Ar' ₁ are respectively P ₁ , P ₂ , Q ₁ , Q ₂ , L ₁ , L ₃ and Ar ₁ represent non-deuterated substituents, and definitions for other substituents are as described above.

Specifically, the compound represented by Formula 1 may be prepared through steps a to c.

First, in the step a, using Tf ₂ O (trifluoromethanesulfonic anhydride), compound 1-1 is prepared by introducing a -OTf (-O ₃ SCF ₃ ) group, which is a reactive group for the Suzuki coupling reaction, to prepare compound 1-2 am.

Next, step b is a step for preparing the compound represented by Formula 1 "through the Suzuki coupling reaction of compounds 1-2 and 1-3. Each of these Suzuki coupling reactions is performed in the presence of a palladium catalyst and a base In addition, the reactor for the Suzuki coupling reaction may be appropriately changed.

Next, step c is a step of deuterating intermediate compound 1' to prepare a compound represented by Formula 1, wherein the deuterium substitution reaction is performed to convert intermediate compound 1' to a benzene-D ₆ (C ₆ D ₆ ) solution and It can be carried out by adding to the same deuterated solvent and then reacting with TfOH (trifluoromethanesulfonic acid).

Meanwhile. The compound represented by Formula 1 has high solubility in an organic solvent used in a solution process, for example, an organic solvent such as cyclohexanone, so that it can be used in a large-area solution process such as an inkjet coating method using a solvent with a high boiling point. Suitable.

The organic material layer containing the compound according to the present invention can be formed using various methods such as a vacuum deposition method and a solution process, and the solution process will be described in detail below.

(coating composition)

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

The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention, and examples thereof include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorinated solvents such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, mesitylene, 1-methylnaphthalene, and 2-methylnaphthalene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; 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; benzoate-based solvents such as butyl benzoate, methyl-2-methoxy benzoate, and ethyl benzoate; phthalate-based solvents such as dimethyl phthalate, diethyl phthalate, and diphenyl phthalate; tetralin; Solvents, such as 3-phenoxytoluene, are mentioned. In addition, the above-mentioned solvent 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 as the host material will be described later.

In addition, the viscosity of the coating composition is preferably 1 cP or more. In addition, considering the ease of coating of the coating composition, the viscosity of the coating composition is preferably 10 cP or less. Also, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% or more. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 20 wt / v% or less so that the coating composition can be coated optimally.

In addition, the solubility (wt%) of the compound represented by 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, the coating composition including the compound represented by Chemical Formula 1 and a solvent may be used in a solution process.

In addition, the present invention provides a method of forming a light emitting layer using the coating composition described above. Specifically, coating the light emitting layer according to the present invention described above on the anode or on the hole transport layer formed on the anode by a solution process; and heat-treating the coated coating composition.

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

In the heat treatment step, the heat treatment temperature is preferably 150 to 230 °C. In addition, the heat treatment time is 1 minute to 3 hours, 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 element)

Meanwhile, the present invention provides an organic light emitting device including the compound represented by Formula 1 above. In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. .

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

In one embodiment, the organic material layer may include a light emitting layer, and in this case, the organic material layer including the compound may be a light emitting layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer, wherein the organic material layer including the compound may be a light emitting layer or an electron injection and transport layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, and an electron injection and transport layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron injection and transport layer.

In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron blocking layer, and an electron injection and transport layer, wherein the organic material layer containing the compound is a light emitting layer or an electron injection and transport layer. can be

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention further includes a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode, in addition to the light emitting layer as an organic material layer. can have a structure that However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.

In addition, the organic light emitting device according to the present invention has a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate in which the first electrode is an anode and the second electrode is a cathode. can be In addition, the organic light emitting device according to the present invention has 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 in which a first electrode is a cathode and a second electrode is an anode. can be 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 .

1 shows 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 this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

2 is 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). is shown. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

The organic light emitting device according to the present invention may be manufactured with materials and methods known in the art, except that the light emitting layer includes the compound according to the present invention and is manufactured as described above.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, using a physical vapor deposition (PVD) 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 a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and depositing a material that can be used as a cathode thereon, it can be prepared.

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

In one 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 preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include 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; 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 easily inject electrons into the organic material layer. Specific examples of the anode material include 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 hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

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

Meanwhile, in the organic light emitting device, an electron suppression layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons to increase hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device. means a layer that serves to improve The electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Chemical Formula 1 or an arylamine-based organic material may be used, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. As the host material, the compound represented by Chemical Formula 1 may be used. In addition, a condensed aromatic ring derivative or a compound containing a heterocyclic ring may be used together with the compound represented by Formula 1 as the host material. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

In addition, examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc. having an arylamino group, and styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

Meanwhile, in the organic light emitting device, a hole blocking layer may be provided between the light emitting layer and the electron transport layer. The hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to improve the efficiency of the organic light emitting device by controlling electron mobility and preventing excessive movement of holes to increase the probability of hole-electron coupling layers that play a role. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound having an electron withdrawing group such as a phosphine oxide derivative may be used, but is not limited thereto.

The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting the received electrons to the light emitting layer, and is formed on the light emitting layer or the hole blocking layer. As such an electron injecting and transporting material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Examples of specific electron injection and transport materials include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives, etc., but are not limited thereto. Or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds , or may be used together with nitrogen-containing 5-membered ring derivatives, etc., but is not limited thereto.

The electron injection and transport layer may also be formed as a separate layer 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 above-described electron injection and transport material may be used as an electron transport material included in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and examples of electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiophyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like can be used.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-hydroxyquinolinato)chlorogallium, bis(2-methyl-8-hydroxyquine nolinato)(o-cresolato)gallium, bis(2-methyl-8-hydroxyquinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-hydroxyquinolinato)(2- Naphtolato) gallium and the like, but are not limited thereto.

In addition to the above-described materials, an inorganic compound such as a quantum dot or a polymer compound may be further included in the light emitting layer, the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer.

The quantum dot may be, for example, a colloidal quantum dot, an alloy quantum dot, a core-shell quantum dot, or a core quantum dot. An element belonging to groups 2 and 16, an element belonging to groups 13 and 15, an element belonging to groups 13 and 17, an element belonging to groups 11 and 17, or an element belonging to groups 14 and 17 It may be a quantum dot containing elements belonging to group 15, such as cadmium (Cd), selenium (Se), zinc (Zn), sulfur (S), phosphorus (P), indium (In), tellurium (Te), lead Quantum dots including elements such as (Pb), gallium (Ga), and arsenic (As) may be used.

The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.

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

Preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail 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 thereto.

Preparation Example 1: Preparation of compound 3-2

Compound 1-a (1.0 eq.) and Compound 1-b (2.1 eq.) were placed in a round bottom flask and dissolved in THF:PhMe 1:1 (v/v). Na ₂ CO ₃ (6.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 130° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 1-c (67% yield).

Compound 1-c (1.0 eq.) was placed in a round bottom flask and dissolved in anhydrous CH ₂ Cl ₂ . Thereafter, pyridine (4.0 eq.) was added dropwise at room temperature, and then the bath temperature was lowered to 0° C. and stirred for 10 minutes. Thereafter, Tf ₂ O (2.4 eq.) dissolved in anhydrous CH ₂ Cl ₂ was slowly added dropwise to the mixture using a dropping funnel, and the bath temperature was gradually raised from 0° C. to room temperature, followed by stirring overnight. After the reaction, the reactant was sufficiently diluted with CH ₂ Cl ₂ and washed with CH ₂ Cl ₂ /brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 1-d (98% yield).

Compound 1-d (1.0 eq.) and Compound 1-e (2.1 eq.) were placed in a round bottom flask and dissolved in THF:PhMe 1:1 (v/v). Na ₂ CO ₃ (6.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 130° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 1-f (87% yield).

Compound 1-f (1.0 eq.) was placed in a round bottom flask under a nitrogen atmosphere and dissolved in benzene-D ₆ (150 eq.). TfOH (2.0 eq.) was slowly added dropwise to the reaction and stirred at 25 °C for 2 hours. D ₂ O was added dropwise to the reactant to terminate the reaction, and potassium phosphate tribasic (30 wt% in aqueous solution, 2.4 eq.) was added dropwise to adjust the pH of the aqueous layer to 9-10. The organic layer was separated by washing with CH ₂ Cl ₂ /DI water. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 3-2 (a+b+c+d+e+f+g+h+i = 50-54, 91% yield).

m/z [M+H] ⁺ 1141.3

Preparation Example 2: Preparation of compound 3-3

Compound 3-3 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 2-a was used instead of compound 1-e. = 50-54) was prepared.

m/z [M+H] ⁺ 1141.4

Preparation Example 3: Preparation of compound 3-5

Compound 3-5 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 3-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 4: Preparation of compound 3-6

Compound 3-6 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 4-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.4

Preparation Example 5: Preparation of Compound 3-8

Compound 3-8 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 5-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 6: Preparation of compound 3-9

Compound 3-9 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 6-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 7: Preparation of compound 3-7

Compound 3-7 (a + b + c + d + e + f + g = 46-50 ) was prepared.

m/z [M+H] ⁺ 1085.5

Preparation Example 8: Preparation of Compound 3-4

Compound 3-4 (a + b + c + d + e + f + g = 46-50 ) was prepared.

m/z [M+H] ⁺ 1085.5

Preparation Example 9: Preparation of compound 3-14

Compound 3-14 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 9-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 10: Preparation of Compound 3-15

Compound 3-15 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 10-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 11: Preparation of compound 3-11

Compound 3-11 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 11-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.4

Preparation Example 12: Preparation of compound 3-12

Compound 3-12 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 12-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 13: Preparation of Compound 3-10

Compound 3-10 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 13-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.6

Preparation Example 14: Preparation of compound 3-13

Compound 3-13 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 14-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 15: Preparation of Compound 3-16

Compound 3-16 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 15-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 16: Preparation of Compound 3-17

Compound 3-17 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 16-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 17: Preparation of Compound 3-18

Compound 3-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 17-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 18: Preparation of compound 3-19

Compound 3-19 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 18-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 19: Preparation of Compound 3-20

Compound 3-20 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 19-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 20: Preparation of compound 3-21

Compound 3-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 20-a was used instead of compound 1-e. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 21: Preparation of compound 3-22

Compound 3-22 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 21-a was used instead of compound 1-e. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 22: Preparation of Compound 3-1

Compound 3-1 (a + b + c + d + e + f + g = 42-46 ) was prepared.

m/z [M+H] ⁺ 981.5

Preparation Example 23: Preparation of Compound 1-6

Compound 1-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 23-a was used instead of compound 1-b and compound 4-a was used instead of 1-e. +e+f+g+h+i=54-58) was prepared.

m/z [M+H] ⁺ 1245.4

Preparation Example 24: Preparation of Compound 1-9

Compound 1-9 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 1-6, except that compound 6-a was used instead of compound 4-a. = 54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 25: Preparation of Compound 1-17

Compound 1-17 (a + b + c + d + e + f + g + h + i) was synthesized in the same manner as in the method for preparing compound 1-6, except that compound 16-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 26: Preparation of Compounds 1-18

Compound 1-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 1-6, except that compound 17-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 27: Preparation of Compounds 1-20

Compound 1-20 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 1-6, except that compound 19-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 28: Preparation of Compound 1-21

Compound 1-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 1-6, except that compound 20-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 29: Preparation of compound 16-6

Compound 16-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 29-a was used instead of compound 1-b and compound 4-a was used instead of 1-e. +e+f+g+h+i=54-58) was prepared.

m/z [M+H] ⁺ 1245.4

Preparation Example 30: Preparation of Compounds 16-18

Compound 16-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 16-6, except that compound 17-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 31: Preparation of Compounds 16-21

Compound 16-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 16-6, except that compound 20-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 32: Preparation of compound 17-6

Compound 17-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 32-a was used instead of compound 1-b and compound 4-a was used instead of 1-e. +e+f+g+h+i=54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 33: Preparation of Compounds 17-18

Compound 17-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 17-6, except that compound 17-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 34: Preparation of Compounds 17-21

Compound 17-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 17-6, except that compound 20-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 35: Preparation of Compound 2-6

Compound 2-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 35-a was used instead of compound 1-b and compound 4-a was used instead of 1-e. +e+f+g+h+i=54-58) was prepared.

m/z [M+H] ⁺ 1245.5

Preparation Example 36: Preparation of Compound 2-18

Compound 2-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 2-6, except that compound 17-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 37: Preparation of compound 2-21

Compound 2-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 2-6, except that compound 20-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 38: Preparation of compound 6-6

Compound 6-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 38-a was used instead of compound 1-a and compound 4-a was used instead of 1-e. +e+f+g+h+i+j=58-62) was prepared.

m/z [M+H] ⁺ 1325.5

Preparation Example 39: Preparation of Compound 6-18

Compound 6-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 6-6, except that compound 17-a was used instead of compound 4-a. +j+k+l=66-70) was prepared.

m/z [M+H] ⁺ 1485.6

Preparation Example 40: Preparation of compound 6-21

Compound 6-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 6-6, except that compound 20-a was used instead of compound 4-a. +j+k+l=66-70) was prepared.

m/z [M+H] ⁺ 1485.6

Preparation Example 41: Preparation of compound 9-6

Compound 9-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 41-a was used instead of compound 1-a and compound 4-a was used instead of 1-e. +e+f+g+h+i+j=58-62) was prepared.

m/z [M+H] ⁺ 1325.5

manufacturing example 42: Preparation of compounds 9-18

Compound 9-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 9-6, except that compound 17-a was used instead of compound 4-a. +j+k+l=66-70) was prepared.

m/z [M+H] ⁺ 1485.6

Preparation Example 43: Preparation of compound 9-21

Compound 9-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 9-6, except that compound 20-a was used instead of compound 4-a. +j+k+l=66-70) was prepared.

m/z [M+H] ⁺ 1485.6

Preparation Example 44: Preparation of compound 36-6

Compound 1-a (1.0 eq.) and Compound 1-b (1.05 eq.) were placed in a round bottom flask and dissolved in THF:PhMe 1:1 (v/v). Na ₂ CO ₃ (3.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (5 mol%) was added dropwise under a bath temperature of 80° C. and stirred for 4 hours. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 44-a (52% yield).

Compound 44-a (1.0 eq.) and Compound 44-b (1.05 eq.) were placed in a round bottom flask and dissolved in THF:PhMe 1:1 (v/v). Na ₂ CO ₃ (6.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 130° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 44-c (60% yield).

Compound 44-c (1.0 eq.) was placed in a round bottom flask and dissolved in anhydrous CH ₂ Cl ₂ . Thereafter, pyridine (4.0 eq.) was added dropwise at room temperature, and then the bath temperature was lowered to 0° C. and stirred for 10 minutes. Thereafter, Tf ₂ O (2.4 eq.) dissolved in anhydrous CH ₂ Cl ₂ was slowly added dropwise to the mixture using a dropping funnel, and the bath temperature was gradually raised from 0° C. to room temperature, followed by stirring overnight. After the reaction, the reactant was sufficiently diluted with CH ₂ Cl ₂ and washed with CH ₂ Cl ₂ /brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 44-d (99% yield).

Compound 44-d (1.0 eq.) and compound 4-a (2.1 eq.) were placed in a round bottom flask and dissolved in THF:PhMe 1:1 (v/v). Na ₂ CO ₃ (6.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 130° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 44-e (79% yield).

Compound 44-e (1.0 eq.) was placed in a round bottom flask under a nitrogen atmosphere and dissolved in benzene-D ₆ (150 eq.). TfOH (2.0 eq.) was slowly added dropwise to the reaction and stirred at 25 °C for 2 hours. D ₂ O was added dropwise to the reactant to terminate the reaction, and potassium phosphate tribasic (30 wt% in aqueous solution, 2.4 eq.) was added dropwise to adjust the pH of the aqueous layer to 9-10. The organic layer was separated by washing with CH ₂ Cl ₂ /DI water. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 36-6 (a+b+c+d+e+f+g+h+i=54-58, 89% yield).

m/z [M+H] ⁺ 1245.5

Preparation Example 45: Preparation of Compound 36-18

Compound 36-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 36-6, except that compound 17-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 46: Preparation of compound 36-21

Compound 36-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 36-6, except that compound 20-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

manufacturing example 47: Preparation of compound 18-6

Compound 18-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 47-a was used instead of compound 1-b and compound 4-a was used instead of 1-e. +e+f+g+h+i=54-58) was prepared.

m/z [M+H] ⁺ 1245.4

Preparation Example 48: Preparation of Compounds 18-18

Compound 18-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 18-6, except that compound 17-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 49: Preparation of Compounds 18-21

Compound 18-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 18-6, except that compound 20-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Preparation Example 50: Preparation of compound 19-6

Compound 19-6 (a+b+c+d) was synthesized in the same manner as in the method for preparing compound 3-2, except that compound 50-a was used instead of compound 1-b and compound 4-a was used instead of 1-e. +e+f+g+h+i=54-58) was prepared.

m/z [M+H] ⁺ 1245.4

Preparation Example 51: Preparation of Compounds 19-18

Compound 19-18 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 19-6, except that compound 17-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.6

Preparation Example 52: Preparation of Compounds 19-21

Compound 19-21 (a+b+c+d+e+f+g+h+i) was synthesized in the same manner as in the method for preparing compound 19-6, except that compound 20-a was used instead of compound 4-a. +j+k=62-66) was prepared.

m/z [M+H] ⁺ 1405.5

Comparative Preparation Example 1: Preparation of Comparative Compound F

Compound Fa (1.0 eq.) and compound Fb (2.2 eq.) were placed in a round bottom flask and dissolved in THF:PhMe 1:1 (v/v). Na ₂ CO ₃ (6.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 130° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound F (86% yield).

m/z [M+H] ⁺ 935.4

Comparative Preparation Example 2: Preparation of Comparative Compound H

Compound Ha (1.0 eq.) and compound Hb (2.1 eq.) were placed in a round bottom flask and dissolved in anhydrous THF. Cs ₂ CO ₃ (20.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 80° C. and stirred for 3 days. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound Hc (76% yield).

Compound Hc (1.0 eq.) was placed in a round bottom flask and dissolved in anhydrous CH ₂ Cl ₂ . Thereafter, pyridine (2.0 eq.) was added dropwise at room temperature, and then the bath temperature was lowered to 0° C. and stirred for 10 minutes. Thereafter, Tf ₂ O (1.2 eq.) dissolved in anhydrous CH ₂ Cl ₂ was slowly added dropwise to the mixture using a dropping funnel, and the bath temperature was gradually raised from 0° C. to room temperature, followed by stirring overnight. After the reaction, the reactant was sufficiently diluted with CH ₂ Cl ₂ and washed with CH ₂ Cl ₂ /brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound Hd (98% yield).

Compound Hd (1.0 eq.) and compound He (1.2 eq.) were placed in a round bottom flask and dissolved in anhydrous THF. CS ₂ CO ₃ (10.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (5 mol%) was added dropwise under a bath temperature of 80° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound H (82% yield).

m/z [M+H] ⁺ 643.31

Comparative Preparation Example 3: Preparation of Comparative Compound I

Compound Ia (1.0 eq.) and Compound Hb (1.1 eq.) were placed in a round bottom flask and dissolved in anhydrous THF. Cs ₂ CO ₃ (10.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (5 mol%) was added dropwise under a bath temperature of 80° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound Ib (64% yield).

Compound Ic (1.0 eq.) and compound 1-d (2.1 eq.) were placed in a round bottom flask and dissolved in anhydrous THF. Cs ₂ CO ₃ (20.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 80° C. and stirred for 3 days. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 1-e (87% yield).

Compound 1-e (1.0 eq.) was placed in a round bottom flask and dissolved in anhydrous CH ₂ Cl ₂ . Thereafter, pyridine (4.0 eq.) was added dropwise at room temperature, and then the bath temperature was lowered to 0° C. and stirred for 10 minutes. Thereafter, Tf ₂ O (2.4 eq.) dissolved in anhydrous CH ₂ Cl ₂ was slowly added dropwise to the mixture using a dropping funnel, and the bath temperature was gradually raised from 0° C. to room temperature, followed by stirring overnight. After the reaction, the reactant was sufficiently diluted with CH ₂ Cl ₂ and washed with CH ₂ Cl ₂ /brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 1-f (99% yield).

Compound 1-f (1.0 eq.) and compound He (1.2 eq.) were placed in a round bottom flask and dissolved in anhydrous THF. CS ₂ CO ₃ (20.0 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (10 mol%) was added dropwise under a bath temperature of 80° C. and stirred overnight. After the reaction, the reactant was cooled at room temperature, sufficiently diluted in EtOAc, and washed with EtOAc/brine to separate an organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound I (76% yield).

m/z [M+H] ⁺ 895.4

Experimental Example 1: Confirmation of deuterium substitution rate

For the compounds prepared in Preparation Examples 1 to 52, the number of deuterium substituted in the compound was obtained through MALDI-TOF MS (Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometer) analysis, and then The deuterium substitution rate was calculated as a percentage of the number of substituted deuteriums relative to the total number of hydrogens available, and is shown in Table 1 below.

compound heavy hydrogen
number of substitutions heavy hydrogen
Substitution rate (%) compound heavy hydrogen
number of substitutions heavy hydrogen
Substitution rate (%) compound 3-2 50-54 92.6-100 Compounds 1-20 62-66 93.9-100 compound 3-3 50-54 92.6-100 compound 1-21 62-66 93.9-100 compounds 3-5 54-58 93.1-100 compound 16-6 54-58 93.1-100 compounds 3-6 54-58 93.1-100 Compounds 16-18 62-66 93.9-100 compounds 3-8 54-58 93.1-100 Compounds 16-21 62-66 93.9-100 compounds 3-9 54-58 93.1-100 compound 17-6 54-58 93.1-100 compounds 3-7 46-50 92.0-100 Compounds 17-18 62-66 93.9-100 Compounds 3-4 46-50 92.0-100 Compounds 17-21 62-66 93.9-100 Compounds 3-14 62-66 93.9-100 compound 2-6 54-58 93.1-100 Compounds 3-15 62-66 93.9-100 Compounds 2-18 62-66 93.9-100 compound 3-11 62-66 93.9-100 compound 2-21 62-66 93.9-100 compound 3-12 62-66 93.9-100 compound 6-6 58-62 93.5-100 compounds 3-10 54-58 93.1-100 Compounds 6-18 66-70 93.9-100 Compounds 3-13 54-58 93.1-100 compound 6-21 66-70 93.9-100 Compounds 3-16 54-58 93.1-100 compound 9-6 58-62 93.5-100 compounds 3-17 62-66 93.9-100 Compounds 9-18 66-70 93.9-100 compounds 3-18 62-66 93.9-100 compound 9-21 66-70 93.9-100 compounds 3-19 54-58 93.1-100 compound 36-6 54-58 93.1-100 compound 3-20 62-66 93.9-100 Compounds 36-18 62-66 93.9-100 compound 3-21 62-66 93.9-100 compound 36-21 62-66 93.9-100 compound 3-22 54-58 93.1-100 compound 18-6 54-58 93.1-100 compound 3-1 42-46 91.3-100 Compounds 18-18 62-66 93.9-100 Compounds 1-6 54-58 93.1-100 Compounds 18-21 62-66 93.9-100 compounds 1-9 54-58 93.1-100 compound 19-6 54-58 93.1-100 Compounds 1-17 62-66 93.9-100 Compounds 19-18 62-66 93.9-100 compounds 1-18 62-66 93.9-100 Compounds 19-21 62-66 93.9-100

Experimental Example 2: Measurement of solubility

It was confirmed whether the compounds and comparative compounds F to I prepared in Preparation Examples 1 to 52 could be dissolved in cyclohexanone at a concentration of 1.3 wt% at 25° C., and the results are shown in Table 2. At this time, the structures of comparative compounds F to I are as follows:

compound Solubility (1.3 wt%) compound Solubility (1.3 wt%) compound 3-2 O compound 16-6 O compound 3-3 O Compounds 16-18 O compounds 3-5 O Compounds 16-21 O compounds 3-6 O compound 17-6 O compounds 3-8 O Compounds 17-18 O compounds 3-9 O Compounds 17-21 O compounds 3-7 O compound 2-6 O Compounds 3-4 O Compounds 2-18 O Compounds 3-14 O compound 2-21 O Compounds 3-15 O compound 6-6 O compound 3-11 O Compounds 6-18 O compound 3-12 O compound 6-21 O compounds 3-10 O compound 9-6 O Compounds 3-13 O Compounds 9-18 O Compounds 3-16 O compound 9-21 O compounds 3-17 O compound 36-6 O compounds 3-18 O Compounds 36-18 O compounds 3-19 O compound 36-21 O compound 3-20 O compound 18-6 O compound 3-21 O Compounds 18-18 O compound 3-22 O Compounds 18-21 O compound 3-1 O compound 19-6 O Compounds 1-6 O Compounds 19-18 O compounds 1-9 O Compounds 19-21 O Compounds 1-17 O compound F O compounds 1-18 O compound G X Compounds 1-20 O compound H O compound 1-21 O compound I O

As can be seen in Table 2, all of the compounds represented by Formula 1 were soluble in cyclohexanone at a concentration of 1.3 wt%, but the comparative compound G was not soluble, and thus the organic layer of the organic light emitting device was prepared by a solution process. It can be seen that it cannot be used as a compound constituting the organic layer during manufacture.

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 cleaned for 5 minutes and transported to a glove box.

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

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

On the hole transport layer, a coating composition in which the light emitting layer host compound 3-2 prepared in Preparation Example 1 and the light emitting layer dopant compound R (98:2 weight ratio) dissolved in cyclohexanone at 1.3 wt/v% was spin coated (4000 rpm) on the hole transport layer. ) 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 evaporator, the compound S was vacuum deposited to a thickness of 350 Å on the light emitting layer to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

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

Examples 2 to 52

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 3 was used instead of Compound 1 as a host of the light emitting layer.

comparative example 1 to comparative example 3

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 3 was used instead of Compound 1 as a host of the light emitting layer.

Experimental Example 3: Characteristic evaluation of organic light emitting device

When a current was applied to the organic light emitting device prepared in the above Examples and Comparative Examples, the driving voltage at a current density of 10 mA/cm ² , the external quantum efficiency (EQE), and the lifetime were measured. Table 3 shows. At this time, the external quantum efficiency (EQE) was obtained as “(number of photons emitted) / (number of charge carriers injected) * 100”, and T90 is the time required for the luminance to decrease from the initial luminance (500 nit) to 90% means

division light emitting layer
host drive voltage
(V@10mA/cm ² ) EQE
(% @10mA/cm ² ) Life (hr)
(T90 @500 nits) Example 1 compound 3-2 6.5 5.52 957 Example 2 compound 3-3 6.8 5.67 978 Example 3 compounds 3-5 6.9 5.62 982 Example 4 compounds 3-6 7.0 5.42 975 Example 5 compounds 3-8 6.9 5.76 985 Example 6 compounds 3-9 7.1 5.86 899 Example 7 compounds 3-7 7.0 5.56 985 Example 8 Compounds 3-4 7.2 5.52 935 Example 9 Compounds 3-14 7.0 5.48 857 Example 10 Compounds 3-15 7.0 5.52 957 Example 11 compound 3-11 6.8 5.60 958 Example 12 compound 3-12 7.1 5.39 974 Example 13 compounds 3-10 7.0 5.45 958 Example 14 Compounds 3-13 7.2 5.46 851 Example 15 Compounds 3-16 6.9 5.75 956 Example 16 compounds 3-17 7.0 5.62 998 Example 17 compounds 3-18 7.1 5.60 978 Example 18 compounds 3-19 7.2 5.58 921 Example 19 compound 3-20 6.9 5.51 987 Example 20 compound 3-21 6.9 5.68 936 Example 21 compound 3-22 7.0 5.70 985 Example 22 compound 3-1 6.9 5.82 925 Example 23 Compounds 1-6 7.0 5.65 897 Example 24 compounds 1-9 7.0 5.58 845 Example 25 Compounds 1-17 7.2 5.57 958 Example 26 compounds 1-18 7.1 5.54 978 Example 27 Compounds 1-20 7.4 5.63 958 Example 28 compound 1-21 7.0 5.50 893 Example 29 compound 16-6 6.9 5.62 898 Example 30 Compounds 16-18 6.7 5.78 857 Example 31 Compounds 16-21 6.8 5.89 959 Example 32 compound 17-6 6.8 5.50 885 Example 33 Compounds 17-18 7.0 5.54 878 Example 34 Compounds 17-21 7.2 5.58 897 Example 35 compound 2-6 7.0 5.56 857 Example 36 Compounds 2-18 7.2 5.60 985 Example 37 compound 2-21 7.0 5.66 905 Example 38 compound 6-6 7.1 5.62 968 Example 39 Compounds 6-18 7.3 5.54 932 Example 40 compound 6-21 7.2 5.68 945 Example 41 compound 9-6 7.0 5.70 985 Example 42 Compounds 9-18 6.9 5.69 936 Example 43 compound 9-21 7.0 5.58 978 Example 44 compound 36-6 7.1 5.52 978 Example 45 Compounds 36-18 7.0 5.59 896 Example 46 compound 36-21 6.9 5.60 958 Example 47 compound 18-6 7.0 5.49 924 Example 48 Compounds 18-18 7.2 5.82 987 Example 49 Compounds 18-21 7.1 5.86 925 Example 50 compound 19-6 7.0 5.69 948 Example 51 Compounds 19-18 6.9 5.57 957 Example 52 Compounds 19-21 7.1 5.55 905 Comparative Example 1 compound F 6.9 4.01 420 Comparative Example 2 compound H 6.9 4.02 122 Comparative Example 3 compound I 7.2 3.99 157

As shown in Table 3, it is confirmed that the organic light emitting device including the compound of the present invention in the light emitting layer has improved efficiency and lifetime compared to the device of the comparative example.

Specifically, the organic light emitting device of Example using the compound represented by Formula 1 as a host of the light emitting layer has higher efficiency than the organic light emitting device of Comparative Examples 1 to 3 using Comparative Compounds F, H, and I as a host of the light emitting layer, respectively. and improved lifespan. It is believed that this is because the compound represented by Formula 1 has a high deuterium substitution rate and thus improves material stability.

Accordingly, it can be seen that when the compound represented by Chemical Formula 1 is used as a host material of the organic light emitting diode, external quantum efficiency and lifetime characteristics of the organic light emitting diode can be simultaneously improved.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron injection and transport layer

Claims (13)

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

In Formula 1,
D means deuterium,
P ₁ and P ₂ are each independently a single bond; or phenylene which is unsubstituted or substituted with deuterium;
Q ₁ and Q ₂ are each independently unsubstituted or deuterium-substituted naphthylene,
L ₁ to L ₄ are each independently a single bond; phenylene unsubstituted or substituted with deuterium; or naphthylene unsubstituted or substituted with deuterium;
Ar ₁ and Ar ₂ are each independently unsubstituted or deuterium-substituted phenyl; or naphthyl unsubstituted or substituted with deuterium;
x, y and z are each independently an integer from 0 to 8;
provided that the compound contains at least one deuterium.
According to claim 1,
The deuterium substitution rate of the compound is 80% or more,
compound.
According to claim 1,
x+y+z is greater than or equal to 1;
compound.
According to claim 1,
P ₁ and P ₂ are single bonds; 1,3-phenylene unsubstituted or substituted with 1 to 4 deuterium; or 1,4-phenylene, which is unsubstituted or substituted with 1 to 4 deuterium atoms;
compound.
According to claim 1,
Q ₁ and Q ₂ are any one of divalent linking groups represented by the following formulas 2a to 2j,
compound:

In Formulas 2a to 2j,
r is an integer from 1 to 6;
According to claim 1,
L ₁ to L ₄ are each independently a single bond; Or any one of the divalent linking groups represented by Formulas 3a to 3m,
compound:

In Formulas 3a to 3m,
s is an integer from 0 to 4;
t is an integer from 0 to 6;
According to claim 6,
L ₁ and L ₂ are each independently a single bond; A divalent linking group represented by Formula 3a; Or a divalent linking group represented by Formula 3b,
Here, s is an integer from 1 to 4,
compound.
According to claim 6,
L ₃ and L ₄ are each independently a single bond; A divalent linking group represented by Formula 3a; A divalent linking group represented by Formula 3b; Or a divalent linking group represented by Formula 3i,
Here, s is an integer from 1 to 4, t is an integer from 1 to 6,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl substituted with 1 to 5 deuterium atoms; 1-naphthyl substituted with 1 to 7 deuterium; or 2-naphthyl substituted with 1 to 7 deuterium;
compound.
According to claim 1,
remind

and above

are equal to each other,
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of compounds represented by Formula 1' below,
compound:
[Formula 1']

In Formula 1',
n means the number of deuterium substitutions in the compound,
Core is any one selected from divalent linking groups represented by the following formulas Core 1 to Core 44,

R is any one selected from substituents represented by the following formulas R1 to R22,

The compound represented by Formula 1' is as follows,























.

a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers is a compound according to any one of claims 1 to 11. To include, an organic light emitting device.
According to claim 12,
The organic material layer containing the compound is a light emitting layer,
organic light emitting device.