KR20220013229A - 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 chemical formula 1 described above can be used as a material for an organic material layer of the organic light emitting device, and can be used in a solution process, and thus can improve efficiency and lifespan characteristics in the organic light emitting device.

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.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and 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 and a cathode and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, it may be made of an electron injection layer, etc. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

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

Meanwhile, in recent years, organic light emitting devices using a solution process, particularly an inkjet process, have been developed instead of the conventional deposition process in order to reduce process costs. In the early days, all organic light emitting device layers were coated with a solution process to develop an organic light emitting device, but the 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. The (hybrid) process is being studied.

Accordingly, the present invention provides a material for a novel organic light emitting device 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 comprising the same.

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

[Formula 1]

In Formula 1,

Q is a divalent substituent represented by any one of the following 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, except when both Ar ₁ and Ar ₂ are unsubstituted phenyl,

When Q is a divalent substituent represented by 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 is a first electrode; a second electrode provided to face the first electrode; and an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes the compound represented by Formula 1 above.

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

1 shows an example of an organic light emitting device including 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 including 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 will show

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

(Definition of Terms)

및

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

and

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; a phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more . 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.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but 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, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound 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 it is preferably from 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 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. However, the present invention is not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

In the present specification, examples of the halogen group 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 an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. 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-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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, 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 an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. 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, stilbenyl group, styrenyl group, and the like, but is 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 carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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 is 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. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenylyl group, or a terphenylyl group, but is not limited thereto. The polycyclic aryl group may be 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, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다. 또한, 벤조플루오레닐기도 상기 플루오레닐기와 마찬가지로 치환되거나, 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

etc. can be However, the present invention is not limited thereto. In addition, the benzofluorenyl group may be substituted like the fluorenyl group, or two may be bonded to 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 heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the above-described aryl group. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group. In the present specification, as for heteroaryl among heteroarylamines, the description regarding heteroaryl described above may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. In the present specification, the description of the above-described aryl group may be applied, except that arylene is a divalent group. In the present specification, the description of the above-described heteroaryl may be applied, except that heteroarylene is a divalent group.

(compound)

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

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

The organic light emitting device employing the compound represented by Formula 1 includes: i) a compound in which the naphthylene linker (Q) is a divalent substituent represented by Formula 1d and L ₁ and L ₂ are both single bonds, and ii) Ar ₁ and Ar 2 may exhibit high efficiency and long lifespan characteristics compared to organic light emitting devices employing a compound in which Ar ₂ is simultaneously unsubstituted phenyl.

In addition, the compound represented by Formula 1 has high solubility in an organic solvent used in the solution process, for example, an organic solvent such as cyclohexanone. suitable for use

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

[Formula 1-A]

[Formula 1-B]

[Formula 1-C]

[Formula 1-D]

In Formulas 1-A to 1-D,

L ₁ to L ₄ , Ar ₁ and Ar ₂ are as defined in Formula 1 above.

In addition, in 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:

.

.

In this case, L ₁ and L ₂ may be the same as 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;

one of L ₁ and L ₂ is phenylene and the other is biphenyldiyl;

both L ₁ and L ₂ are phenylene; or

Both L ₁ and L ₂ may be biphenyldiyl.

이고, 다른 하나는 단일결합이거나;Also, for example, one of L ₁ and L ₂ is

and the other is a single bond;

이고, 다른 하나는 단일결합이거나;one of L ₁ and L ₂ is

and the other is a single bond;

이고, 다른 하나는

이거나;one of L ₁ and L ₂ is

and the other

is;

이고, 다른 하나는

이거나;one of L ₁ and L ₂ is

and the other

is;

이고, 다른 하나는

이거나;one of L ₁ and L ₂ is

and the other

is;

이거나; both L ₁ and L ₂

is;

이거나; 또는both L ₁ and L ₂

is; or

일 수 있다.both L ₁ and L ₂

can be

Also, in Formula 1, L ₃ and L ₄ may each independently represent a single bond or C _6-20 arylene.

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

In this case, L ₃ and L ₄ may be the same as each other. Alternatively, L ₃ and L ₄ may be different.

More specifically, L ₃ and L ₄ are both a single bond;

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

L ₃ and L ₄ may both be phenylene.

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

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

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

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

L ₃ and L ₄ may both be 1,4-phenylene.

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

이거나; one of L ₃ and L ₄ is a single bond, and the other is

is;

이거나; one of L ₃ and L ₄ is a single bond, and the other is

is;

이고, 다른 하나는

이거나;one of L ₃ and L ₄ is

and the other

is;

이거나; 또는L ₃ and L ₄ are both

is; or

일 수 있다.L ₃ and L ₄ are both

can be

In addition, in 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 are each independently 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.

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

In this case, Ar ₁ and Ar ₂ may be the same as each other. Alternatively, Ar ₁ and Ar ₂ may be different.

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

.

.

은 아니다.provided that both Ar ₁ and Ar ₂

is not

이고, 나머지 하나는 하기로 구성되는 군으로부터 선택되는 어느 하나이거나; 또는In addition, one of Ar ₁ and Ar ₂ is

and the other one is any one selected from the group consisting of; or

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

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

.

.

이거나;Also preferably, Ar ₁ and Ar ₂ are both

is;

이고, 다른 하나는

이거나; 또는 one of Ar ₁ and Ar ₂ is

and the other

is; or

일 수 있다.Ar ₁ and Ar ₂ are both

can be

Representative examples of the compound represented by Formula 1 are as follows:

.

Meanwhile, the compound represented by Chemical Formula 1 may be prepared by, for example, a preparation method as shown in Scheme 1 below.

[Scheme 1]

In Scheme 1, the definition of each substituent is the same as described above.

Specifically, the compound represented by Formula 1 may be prepared through steps a and b.

First, in step a, using Tf ₂ O (Trifluoromethanesulfonic anhydride), the -OTf(-O ₃ SCF ₃ ) group, which is a reactive group for the Suzuki coupling reaction, is introduced into compound 1-1 to prepare compound 1-2. to be.

Next, step b is a step of preparing the compound represented by Formula 1 through the Suzuki coupling reaction of Compounds 1-2 and 1-3. The Suzuki coupling reaction is preferably performed in the presence of a palladium catalyst and a base, respectively. In addition, the reactive group for the Suzuki coupling reaction may be appropriately changed, and the method for preparing the compound represented by Formula 1 may be more specific in Preparation Examples to be described later.

(Coating composition)

On the other hand, the compound according to the present invention can form the organic material layer of the organic light emitting device, particularly the light emitting layer, by a solution process. Specifically, the compound may be used as a host material of the light emitting layer. To this end, the present invention provides a coating composition comprising the above-described 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 for example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o - Chlorine 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 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; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol alcohols and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents such as butylbenzoate, methyl-2-methoxybenzoate, and ethylbenzoate; 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 solvents may be used alone or as a mixture 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 for the host material will be described later.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy in 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 Formula 1 at room temperature/atmospheric 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 Formula 1 and the solvent may be used in a solution process.

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

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

The heat treatment temperature in the heat treatment step is preferably 150 to 230 ℃. 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)

In addition, the present invention provides an organic light emitting device comprising 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 an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes the compound represented by Formula 1 above.

In addition, the organic light emitting device according to the present invention is an organic light emitting device having 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 a first electrode is an anode and a 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 the organic light emitting diode 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 including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 . In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

2 is an example of an organic light emitting device including 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 will show In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

The organic light emitting device according to the present invention may be manufactured using 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, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate to form an anode And, after forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon.

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

In one example, the first electrode is an anode, 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 large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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 to facilitate electron injection 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; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

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

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them to the light emitting layer. 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 a conjugated portion and a non-conjugated portion together may be used, but the present invention is not limited thereto. .

Meanwhile, the organic light emitting device may include an electron suppression layer between the hole transport layer and the light emitting layer. The electron suppression layer is formed on the hole transport layer, preferably provided in contact with the light emitting layer, adjusts hole mobility, prevents excessive movement of electrons, and increases the hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device It means a layer that plays a role in improving The electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Formula 1 or an arylamine-based organic material may be used, but is not limited thereto.

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

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

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 provided in contact with the light emitting layer, to control electron mobility and prevent excessive movement of holes to increase the hole-electron coupling probability, thereby improving the efficiency of the organic light emitting device layer that plays 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 into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but the present invention 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 the electrode and transporting the received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer. As the electron injection and transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples of the electron injection and transport material include Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives, but is not limited thereto. Or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives, metal complex compounds , or may be used together with a nitrogen-containing 5-membered ring derivative, and the like, but is not limited thereto.

The electron injection and transport layer may 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 electron injection and transport material described above may be used as the electron transport material included in the electron transport 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 is LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc. 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-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

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

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

The compound represented by Formula 1 and the preparation of an organic light emitting device including the same will be described in detail in Examples below. 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 B1

Compound 1-a (1 g, 1.0 eq.) and compound 1-b (2.1 eq.) were placed in a round bottom 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 under a bath temperature of 90° C. and stirred for 3 days. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 B1 (86% yield).

m/z [M+H] ⁺ = 885.3

Preparation 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 bottom 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 under a bath temperature of 90° C. and stirred overnight. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 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 bottom 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 under a bath temperature of 90° C. and stirred overnight. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 B4 (85% yield).

m/z [M+H] ⁺ = 585.1

Preparation Example 3: Preparation of compound B10

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

m/z [M+H] ⁺ = 961.4

Preparation Example 4: Preparation of compound B3

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

m/z [M+H] ⁺ = 961.4

Preparation 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 bottom 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 under a bath temperature of 90° C. and stirred for 2 days. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 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 CH ₂ Cl ₂ . Thereafter, pyridine (2.0 eq.) was added dropwise at room temperature, and the bath temperature was lowered to 0° C. and stirred for 10 minutes. Then, 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 slowly raised from 0° C. to room temperature, followed by stirring overnight. After the reaction, the reactant was sufficiently diluted in CH ₂ Cl ₂ and washed with CH ₂ Cl ₂ /brine to separate the 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 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 bottom 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 under a bath temperature of 90° C. and stirred for 2 days. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 A1 (yield 92%).

m/z [M+H] ⁺ = 809.3

Preparation Example 6: Preparation of compound A2

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

m/z [M+H] ⁺ = 809.3

Preparation 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 bottom 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 under a bath temperature of 90° C. and stirred for 2 days. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 A4 (83% yield).

m/z [M+H] ⁺ = 1037.4

Preparation Example 8: Preparation of compound A3

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

m/z [M+H] ⁺ = 885.3

Preparation 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 bottom 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 under a bath temperature of 90° C. and stirred for 2 days. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 C1 (83% yield).

m/z [M+H] ⁺ = 885.3

Preparation 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 bottom 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 under a bath temperature of 90° C. and stirred overnight. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 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 bottom 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 under a bath temperature of 90° C. and stirred overnight. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 C2 (87% yield).

m/z [M+H] ⁺ = 885.3

Preparation Example 11: Preparation of compound C3

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

m/z [M+H] ⁺ = 835.3

Preparation 12: Preparation of compound C4

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

m/z [M+H] ⁺ = 961.4

Preparation 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 bottom 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 under a bath temperature of 90° C. and stirred for 2 days. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 D1 (91% yield).

m/z [M+H] ⁺ = 885.3

Preparation 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 bottom 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 under a bath temperature of 90° C. and stirred overnight. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 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 bottom 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 under a bath temperature of 90° C. and stirred overnight. After the reaction, the reactant was cooled to room temperature, diluted sufficiently in EtOAc, and washed with EtOAc/brine to separate the 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 D2 (89% yield).

m/z [M+H] ⁺ = 885.3

Preparation 15: Preparation of compound D4

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

m/z [M+H] ⁺ = 961.4

Preparation 16: Preparation of compound D3

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

m/z [M+H] ⁺ = 885.3

Comparative Preparation Example 1: Preparation of Comparative Compound X1

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

m/z [M+H] ⁺ = 785.3

Comparative Preparation Example 2: Preparation of Comparative Compound X2

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

m/z [M+H] ⁺ = 733.3

Comparative Preparation Example 3: Preparation of Comparative Compound X3

Compound X3 (90% yield) was prepared in the same manner as in 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 indium tin oxide (ITO) to a thickness of 500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl and acetone and dried. After washing the substrate for 5 minutes, the substrate was transported to a glove box.

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

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

On the hole transport layer, the light emitting layer host compound B1 prepared in Preparation Example 1 and the light emitting layer dopant The compound Dopant (weight ratio of 98:2) was dissolved in cyclohexanone at 2 wt/v% at 2 wt/v% by spin coating (4000 rpm) and A light emitting layer was formed to a thickness of 400 Å by heat treatment at 180° C. for 30 minutes.

After transferring to a vacuum evaporator, the compound ETL was vacuum deposited to a thickness of 350 Å on the emission 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 the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of 0.3 Å/sec for LiF and 2 Å/sec for aluminum was maintained, and the vacuum degree during deposition was 2*10 ^-7 to 5 *10 ^-8 torr was maintained.

Examples 2 to 16

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound B1 as the host of the light emitting layer. At this time, the compounds used in the Examples are summarized as follows.

Comparative Examples 1 to 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound B1 as the host of the light emitting layer. In this case, the compounds used in Comparative Examples are as follows.

[Experimental example]

Experimental Example 1: Characteristic evaluation of organic light emitting devices

When a current was applied to the organic light emitting diodes prepared in Examples and Comparative Examples, the driving voltage at a current density of 10 mA/cm ² , external quantum efficiency (EQE), and lifespan were measured. Table 1 shows. At this time, the external quantum efficiency (EQE) was calculated as “(the number of emitted photons) / (the number of injected charge carriers) * 100”, and T90 is the time it takes 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 ) Lifetime (hr)
(T90 @500 nits) 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, it can be seen that the organic light emitting device of the Example using the compound represented by 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 Comparative Example. have.

Specifically, in the organic light emitting device of an embodiment using the compound represented by Formula 1 as a host for the light emitting layer, in Formula 1, Ar ₁ and Ar ₂ are both unsubstituted phenyl, Comparative Compound X1, and Q in Formula 1 is the Compared to the organic light emitting devices of Comparative Examples 1 to 3 using comparative compounds X2 and X3 in which both L ₁ and L ₂ are single bonds as the host of the light emitting layer, respectively, high efficiency and significantly longer lifespan indicated. In general, considering that the luminous efficiency and lifespan characteristics of the organic light emitting device have a trade-off relationship with each other, the organic light emitting device employing the compound of the present invention exhibits significantly improved device characteristics compared to the comparative example device. means

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 (10)

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

In Formula 1,
Q is a divalent substituent represented by any one of the following 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, except when both Ar ₁ and Ar ₂ are unsubstituted phenyl,
When Q is a divalent substituent represented by Formula 1d, at least one of L ₁ and L ₂ is a substituted or unsubstituted C _6-60 arylene.
With respect to paragraph 1,
The compound is represented by any one of the following formulas 1-A to 1-D,
compound:
[Formula 1-A]

[Formula 1-B]

[Formula 1-C]

[Formula 1-D]

In Formulas 1-A to 1-D,
L ₁ to L ₄ , Ar ₁ and Ar ₂ are as defined in claim 1.
With respect to paragraph 1,
one of L ₁ and L ₂ is C _6-20 arylene, and the other is a single bond or C _6-20 arylene,
compound.
With respect to paragraph 1,
one of L ₁ and L ₂ is phenylene, and the other is a single bond;
one of L ₁ and L ₂ is phenylene and the other is biphenyldiyl;
both L ₁ and L ₂ are phenylene; or
L ₁ and L ₂ are both biphenyldiyl,
compound.
With respect to paragraph 1,
L ₃ and L ₄ are each independently a single bond, or phenylene,
compound.
With respect to paragraph 1,
L ₃ and L ₄ are both single bonds;
one of L ₃ and L ₄ is a single bond and the other is 1,3-phenylene or 1,4-phenylene;
one of L ₃ and L ₄ is 1,3-phenylene and the other is 1,4-phenylene;
L ₃ and L ₄ are both 1,3-phenylene; or
L ₃ and L ₄ are both 1,4-phenylene;
compound.
With respect to paragraph 1,
one of Ar ₁ and Ar ₂ is naphthyl unsubstituted or substituted with 1 to 5 C _1-10 alkyl, the other is unsubstituted or substituted with 1 to 5 C _1-10 alkyl phenyl; or naphthyl unsubstituted or substituted 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, 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.
With respect to paragraph 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of
compound:

.
With respect to paragraph 1,
The compound is any one selected from the group consisting of the following compounds,
compound:

.
a first electrode; a second electrode provided to face the first electrode; and a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes the compound according to any one of claims 1 to 9. .

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