KR20210155430A - 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 comprising the same. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 can be used as a material for the organic material layer of the organic light emitting device, can be used in a solution process, and can exhibit an effect of improving the efficiency, lowering driving voltage and/or improving lifespan characteristics of 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. Therefore, only HIL, HTL, and EML are processed in the solution process in the regular structure, and subsequent processes are performed using the conventional deposition process. A hybrid process using

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,

each Y is independently O, S, Se, Te, NR', C(R') ₂ , or Si(R') ₂ ,

R' is each independently hydrogen; substituted or unsubstituted C _6-60 alkyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

L _{One To} L ₂ Each independently, a single bond; Or a substituted or unsubstituted C _6-60 arylene,

Ar ₁ is substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

Ar ₂ and Ar ₃ are each independently, substituted or unsubstituted C _6-60 aryl; _{or C 2-60} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

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 the above formula (1) 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 exhibit the effect of improving the efficiency of the organic light emitting device, low driving voltage and/or lifespan characteristics .

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 a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), an electron transport layer (7), an electron injection layer (8) and a cathode (4) It shows an example of the organic light emitting device made up.

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

(Definition of Terms)

또는

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

or

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 atoms, which 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 are 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 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 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 biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.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 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. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description regarding heteroaryl described above may be applied, except that it is formed by combining two substituents.

(compound)

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

Formula 1 may be represented by Formula 1-1 below:

[Formula 1-1]

In the above, Y, L ₁ , L ₂ , Ar _{1 To} Ar ₃ are as defined in Formula 1.

Preferably, in Formula 1, each Y is independently O, S, Se, Te, NR', C(R') ₂ , or Si(R') ₂ , and R' is each independently, C _{1 -6} alkyl; unsubstituted phenyl; or t-butylphenyl. More preferably, each R' is independently methyl; n-butyl; phenyl; or t-butylphenyl.

Preferably, all of Y in Formula 1 may be the same.

Preferably, L _{One To} L ₂ Each independently, a single bond; or substituted or unsubstituted C _6-20 arylene.

Preferably, _{each L 1} is independently a single bond; unsubstituted phenylene; phenylene substituted with 1 or 2 C _{1-6 alkyl;} or pyridinediyl. More preferably, _{each L 1} is independently a single bond; unsubstituted phenylene; methyl phenylene; dimethyl phenylene; or pyridinediyl.

Preferably, L ₂ are each independently, unsubstituted phenylene; phenylene substituted with 1 or 2 C _{1-6 alkyl;} or pyridinediyl. More preferably, _{each L 2} is independently a single bond; unsubstituted phenylene; dimethyl phenylene; or pyridinediyl.

Preferably, Ar ₁ to Ar ₃ are each independently, substituted or unsubstituted C _6-20 aryl; _{or C 2-20} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

Preferably, Ar ₁ is substituted or unsubstituted C _6-20 aryl, more preferably, unsubstituted phenyl; or phenyl substituted with 1 or 2 C _{1-10 alkyl.} More preferably, Ar ₁ is unsubstituted phenyl; dimethylphenyl; n-butylphenyl; t-butylphenyl; di-t-butylphenyl.

Preferably, Ar ₂ and Ar ₃ are each independently any one selected from the group consisting of:

above,

n and m are each independently an integer of 0 to 2,

R'' is each independently C _1-10 alkyl,

_{Ar'' is each independently C 2-10} heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S;

X is C(R _a- )(R _b ), O or S;

R _a and R _b are each independently hydrogen or C _1-10 alkyl.

Preferably, Ar ₂ and Ar ₃ are each independently any one selected from the group consisting of:

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

On the other hand, the present invention provides a method for preparing the compound represented by the above formula (1).

For example, when L ₁ and L ₂ of Formula 1 are both single bonds, the compound represented by Formula 1 may be prepared by a preparation method as shown in Scheme 1 below. In addition, _{when both L 1} and L ₂ of Formula 1 are not single bonds, the compound represented by Formula 1 may be prepared by a manufacturing method as shown in Scheme 2 below:

[Scheme 1]

[Scheme 2]

In Schemes 1 and 2, definitions other than X' are the same as defined above, and X' is halogen, preferably chloro or bromo.

Scheme 1 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art.

The Suzuki coupling reaction in Scheme 2 is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art.

In this way, when the amine group is directly bonded to the core, the amine group can be bonded to the core by an amine substitution reaction as shown in Scheme 1, and in other cases, the Suzuki coupling reaction as shown in Scheme 2 may be used to couple the amine group to the core.

For example, when L ₁ is a single bond and L ₂ is not a single bond, the compound of Formula 1 may be prepared by sequentially performing step 1 of Scheme 2 and step 2 of Scheme 1.

The manufacturing method 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 dopant material of the emission 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, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents, such as acetone, methyl ethyl ketone, 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 solvents such as butylbenzoate and methyl-2-methoxybenzoate; 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, toluene may be used as the solvent.

In addition, the coating composition may further include a compound used as a host material, 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 is preferably 0.1 wt/v% to 20 wt/v%.

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.

Also, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Also, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. 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 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, an electron injection layer 8, and a cathode 4 An example of an organic light emitting device is shown. 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 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 compounds 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, polyaniline and polythiophene-based conductive compounds, and the like, 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. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The emission layer may include a host material and a dopant material. As the dopant material, the compound represented by the above-described Chemical Formula 1 may be used. In addition, as a host material, a condensed aromatic ring derivative, a heterocyclic ring containing compound, etc. can be used. 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.

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 electron control 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 LiF, NaF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, pre Orenylidene methane, anthrone, etc. derivatives thereof, metal complex compounds, or nitrogen-containing 5-membered ring derivatives may be used, but the present invention is not limited thereto.

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.

[Synthesis Example]

Synthesis Example 1: Preparation of compound 1

(Synthesis Example 1-1)

250 of compound a1 (5.0 g, 13.7 mmol), 1-Bromonaphthalen-2-ol (6.1 g, 27.4 mmol), sodium carbonate (5.8 g, 54.8 mmol), Pd(PPh ₃ ) ₄ (0.16 g, 0.14 mmol) Into an mL round bottom flask, 70 mL of anhydrous toluene (0.2 M) and 20 mL of distilled water were added. The mixture was stirred overnight at a bath temperature of 100 °C. After cooling to room temperature, the reactant was passed through a Celite/Floricil/Silica pad while flowing toluene. The filtrate was concentrated under reduced pressure and precipitated with methanol/tetrahydrofuran to obtain an intermediate a2.

(Synthesis Example 1-2)

Intermediate a2 (3.5 g, 8.8 mmol) and potassium carbonate (6.1 g, 43.9 mmol) were placed in a 250 mL round bottom flask and dissolved in 90 mL of NMP (0.1 M), followed by stirring at a bath temperature of 180 ° C. overnight. After cooling to room temperature, hexane and water were added dropwise to precipitate, filtered, and washed with tetrahydrofuran and methanol to obtain an intermediate a3.

(Synthesis Example 1-3)

Intermediate a3 (3.0 g, 8.4 mmol) and bromine (Br ₂ ) (4.7 g, 29.3 mmol) were placed in a 500 mL round bottom flask, and 280 mL of chloroform (0.03 M) was added thereto. The mixture was stirred for two days under a bath temperature of 40 °C. Tetrahydrofuran and methanol were added dropwise to the reaction mixture to precipitate, followed by filtration to obtain an intermediate a4.

(Synthesis Example 1-4)

Intermediate a4 (2.0 g, 3.9 mmol), diphenylamine (0.66 g, 4.0 mmol), sodium t-butoxide (0.41 g, 4.3 mmol), Pd(P( t- Bu) ₃ ) ₂ (0.10 g, 0.20 mmol) It was placed in a 500 mL round bottom flask, filled with nitrogen, and then 200 mL of toluene (0.02 M) was added. Thereafter, the mixture was stirred for 4 hours at a bath temperature of 110 °C. After cooling to room temperature, it was washed with water, hexane, and methanol, and purified by column chromatography to obtain an intermediate a.

(Synthesis Example 1-5)

Intermediate a (1.0 g, 1.7 mmol), aniline (0.075 g, 0.8 mmol), sodium t-butoxide (0.19 g, 2 mmol), Pd(P( t- Bu) ₃ ) ₂ (0.04 g, 0.08 mmol) was prepared It was placed in a 500 mL round-bottom flask, filled with nitrogen, and then 120 mL of toluene was added. Thereafter, the mixture was stirred for 6 hours at a bath temperature of 110 °C. After cooling to room temperature, the mixture was washed with water, hexane, and methanol, and recrystallized from chlorobenzene to obtain Compound 1.

MS: [M+H] ⁺ = 1140

Synthesis Example 2: Preparation of compound 2

Compound 2 was prepared in the same manner as in Synthesis Example 1, except that 4-(t- butyl)aniline was used instead of aniline of Synthesis Example 1-5.

MS: [M+H] ⁺ = 1196

Synthesis Example 3: Preparation of compound 3

Intermediate a (1.0 g, 1.7 mmol), Intermediate b (0.27 g, 0.8 mmol), sodium carbonate (0.29 g, 2.7 mmol), Pd(PPh ₃ ) ₄ (0.09 g, 0.08 mmol) were placed in a 250 mL round bottom flask. 50 mL of toluene and 10 mL of distilled water were added thereto. After stirring overnight at a bath temperature of 100 °C and cooling to room temperature, the reactant was passed through a Celite/Floricil/Silica pad while flowing toluene. The filtrate was concentrated under reduced pressure and recrystallized from chlorobenzene to obtain compound 3.

MS: [M+H] ⁺ = 1292

Synthesis Example 4: Preparation of compound 4

Intermediate c and compound 4 were prepared in the same manner as in Synthesis Example 1, except that 4-(t- butyl)-N-phenylaniline was used instead of diphenylamine of Synthesis Example 1-4.

MS: [M+H] ⁺ = 1252

Synthesis Example 5: Preparation of compound 5

Intermediate d and compound 5 were prepared in the same manner as in Synthesis Example 1, except that intermediate d1 was used instead of diphenylamine of Synthesis Example 1-4.

MS: [M+H] ⁺ = 1372

[Example]

Example 1: Fabrication of an organic light emitting device

A glass substrate on which indium tin oxide (ITO) was deposited to a thickness of 500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fisher Co. was used as the detergent, and distilled water filtered secondarily through 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 washing was performed with acetone, distilled water, and isopropyl alcohol and dried to prepare a washed ITO glass substrate.

A composition obtained by mixing the following compounds Z-1 and Z-2 in a weight ratio of 8:2 on the ITO transparent electrode was spin-coated and cured at 220 °C and 30 minutes on a hot plate under a nitrogen atmosphere to form a hole injection layer with a thickness of 400 Å. formed. On the hole injection layer, a composition obtained by dissolving the following compound Z-3 in toluene at a weight ratio of 1% was spin-coated and heat-treated on a hot plate at 200° C. and 30 minutes to form a hole transport layer having a thickness of 200 Å. On the hole transport layer, a composition obtained by dissolving the following compound Z-4 and the previously prepared compound 1 in a weight ratio of 98:2 in toluene at a weight ratio of 0.5% was spin-coated to form a light emitting layer having a thickness of 250 Å, and on a hot plate under a nitrogen atmosphere. The coating composition was dried at 120 °C for 10 minutes. Thereafter, the following compounds Z-5 (electron transport layer, 300 Å), LiF (electron injection layer, 10 Å), and Al (cathode, 1000 Å) were sequentially deposited in a vacuum evaporator to manufacture an organic light emitting device. In the above process, the deposition rate of 0.3 Å/sec for LiF and 2 Å/sec for aluminum (Al) was maintained, and the vacuum degree during deposition was maintained at ^{2x10 -7} to 5x10 ^{-8 torr.}

Examples 2 to 5

As shown in Table 1 below, an organic light emitting diode was manufactured in the same manner as in Example 1, except that Compounds 2 to 5 were used instead of Compound 1.

Comparative Examples 1 to 2

As shown in Table 1 below, an organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compounds A to B were used instead of compound 1.

Experimental Example: Characteristics Evaluation of Organic Light-Emitting Devices

The driving voltage, luminous efficiency, quantum efficiency, and lifetime (T95) values of the organic light emitting diodes manufactured in Examples 1 to 5 and Comparative Examples 1 to 2 ^{were measured at a current density of 10 mA/cm 2} and the results are shown in the table below. 1 is shown. The lifetime (T95) in Table 1 below means the time (hr) required for the luminance to decrease from the initial luminance to 95%.

light emitting layer
dopant drive voltage
(V) luminous efficiency
(cd/A) quantum efficiency
(%) T95
(hr) Example 1 compound 1 4.53 5.22 6.07 120 Example 2 compound 2 4.52 5.05 5.89 125 Example 3 compound 3 4.63 5.03 5.85 108 Example 4 compound 4 4.57 5.42 6.15 99 Example 5 compound 5 4.61 5.17 6.00 90 Comparative Example 1 compound A 5.01 2.83 1.97 5 Comparative Example 2 compound B 4.95 3.40 3.78 25

From the above experimental results, it can be confirmed that the compound of Formula 1 can be used as a dopant in the emission layer of an organic light emitting device and can be used in a solution process during device manufacturing.

In addition, as shown in Table 1, it can be seen that the organic light emitting device using the compound of Formula 1 as a dopant in the light emitting layer exhibits low driving voltage, high luminous efficiency and quantum efficiency, and excellent lifespan characteristics.

1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron transport layer 8: electron injection layer

Claims (11)

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

In Formula 1,
each Y is independently O, S, Se, Te, NR', C(R') ₂ , or Si(R') ₂ ,
R' is each independently hydrogen; substituted or unsubstituted C _6-60 alkyl; substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
L ₁ and L ₂ are each independently, a single bond; Or a substituted or unsubstituted C _6-60 arylene,
Ar ₁ is substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
Ar ₂ and Ar ₃ are each independently, substituted or unsubstituted C _6-60 aryl; _{or C 2-60} heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
According to claim 1,
The formula 1 is represented by the following formula 1-1,
compound:
[Formula 1-1]

In the above, Y, L ₁ , L ₂ , Ar _{1 To} Ar ₃ are as defined in claim 1.
According to claim 1,
each Y is independently O, S, Se, Te, NR', C(R') ₂ , or Si(R') ₂ ,
each R' is independently C _1-6 alkyl; unsubstituted phenyl; or t-butylphenyl;
compound.
According to claim 1,
L ₁ are each independently, a single bond; unsubstituted phenylene; phenylene substituted with 1 or 2 C _{1-6 alkyl;} or pyridinediyl,
compound.
According to claim 1,
L ₂ are each independently, a single bond; unsubstituted phenylene; phenylene substituted with 1 or 2 C _{1-6 alkyl;} or pyridinediyl,
compound.
According to claim 1,
Ar ₁ is unsubstituted phenyl; or phenyl substituted with 1 or 2 C _{1-10 alkyl;}
compound.
According to claim 1,
Ar ₂ and Ar ₃ are each independently, substituted or unsubstituted C _6-20 aryl; _{or C 2-20} heteroaryl comprising any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S;
compound.
8. The method of claim 7,
Ar ₂ and Ar ₃ are each independently any one selected from the group consisting of
compound:

above,
n and m are each independently an integer of 0 to 2,
R'' is each independently C _1-10 alkyl,
_{Ar'' is each independently C 2-10} heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S;
X is C(R _a- )(R _b ), O, or S;
R _a and R _b are each independently hydrogen or C _1-10 alkyl.
8. The method of claim 7,
Ar ₂ and Ar ₃ are each independently any one selected from the group consisting of
compound:

According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
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 10. .

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