KR20200106723A - Novel polymer and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a polymer compound and an organic light emitting device using the same. In the polymer including a repeating unit represented by a formula 1 of the present invention, n is an integer of 5 to 2,000.

Description

Novel polymer and organic light emitting device comprising the same

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

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

The 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, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

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

On the other hand, in recent years, in order to reduce process cost, an organic light emitting device using a solution process, especially an inkjet process, has been developed instead of a conventional deposition process. In the early days, an attempt was made to develop an organic light-emitting device by coating all organic light-emitting device layers by a solution process, but the current technology has limitations, so only HIL, HTL, and EML are processed in a solution process in the form of a regular structure. A hybrid process that utilizes 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 deposited by a solution process at the same time.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a polymer comprising a repeating unit represented by the following formula (1):

[Formula 1]

In Formula 1,

R ₁ to R ₃ are each independently hydrogen; Or substituted or unsubstituted C _1-10 alkyl,

R ₄ is substituted or unsubstituted C _1-10 alkyl; Or substituted or unsubstituted C _6-60 aryl,

X is substituted or unsubstituted C _1-60 alkylene; Substituted or unsubstituted C _6-60 arylene; (Substituted or unsubstituted C _1-60 alkylene)-O-; Or (substituted or unsubstituted C _1-60 alkylene)-O-(substituted or unsubstituted C _6-60 arylene),

L ₁ is a single bond; Or substituted or unsubstituted C _6-60 arylene, or combine with R ₄ to form a C _6-60 aryl ring,

L ₂ and L ₃ 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,

Ar ₂ is N(Ar ₃ )(Ar ₄ ); Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,

Ar ₃ and Ar ₄ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,

n is an integer from 5 to 2,000.

In addition, the present invention is a positive electrode; A cathode provided to face the anode; A light-emitting layer provided between the anode and the cathode; And a hole injection layer or a hole transport layer provided between the anode and the emission layer, wherein the hole injection layer or the hole transport layer comprises the polymer.

The polymer according to the present invention can be used as a material for a hole injection layer or a hole transport layer of an organic light-emitting device, and can be deposited by a solution process, and improves efficiency, low driving voltage and/or lifespan characteristics in an organic light-emitting device. I can make it.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, and a cathode 5.
2 is composed of a substrate (1), an anode (2), a hole injection layer (6), a hole transport layer (3), a light emitting layer (4), an electron transport layer (7), an electron injection layer (8) and a cathode (5). An example of an organic light emitting device is shown.
3 is GPC data of Compound 1 according to Preparation Example 1 of the present invention.
4 is GPC data of Compound 2 according to Preparation Example 2 of the present invention.
5 is GPC data of Compound 3 according to Preparation Example 3 of the present invention.
6 is GPC data of Comparative Compound 1 according to Preparation Example 4 of the present invention.

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

,

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

,

or

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the above exemplified substituents. . For example, "a substituent to 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 to which two phenyl groups are connected.

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

In the present specification, the ester group may be substituted with an oxygen of the ester group with a straight chain, 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 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 is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

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

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 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 cycloalkyl group has 3 to 20 carbon atoms. 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 are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl 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. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbons is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, 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, isoxazolyl group, thiiadia There may be a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the description of the aforementioned heterocyclic group may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that two substituents are bonded to each other.

The present invention provides a polymer comprising the repeating unit represented by Formula 1.

In the conventional solution deposition material, even if there is solubility in a solvent, the material is dissolved in a solvent used for the next layer deposition, and the layer is mixed, thereby deteriorating device performance.

However, the polymer including the repeating unit represented by Formula 1 according to the present invention has excellent solubility in an organic solvent and exhibits excellent hole transport properties in the device after film formation, and thus, a hole injection layer (HIL) or a hole transport layer ( It was confirmed that it can be suitably used as a soluble OLED material for HTL) formation.

In addition, since the polymer according to the present invention is a polymer without reactive benzyl hydrogen in its main chain, it can be expected to improve device life due to increased material stability.

The polymer containing the repeating unit represented by Formula 1 is not modified by an additional solution process performed after the solution coating and heat treatment process, and improves the efficiency and life of the device. Hereinafter, the present invention will be described in detail.

(Repeat Unit)

In the present specification, the'repeating unit' is a repeating unit represented by Formula 1 included in the polymer according to the present invention, and has excellent hole transport properties.

Preferably, R ₁ to R ₃ are each independently hydrogen; Or methyl.

Preferably, R ₄ is methyl; Or substituted or unsubstituted phenyl.

Preferably, X is substituted or unsubstituted C _1-10 alkylene; (Substituted or unsubstituted C _1-10 alkylene)-O-; Or substituted or unsubstituted C _1-10 alkylene)-O-(substituted or unsubstituted C _6-12 arylene), more preferably butylene; -(Butylene)-O-; Or -(butylene)-O-phenylene.

Preferably, L ₁ is a single bond; Phenylene; Or R ₄ and bonded to each other to form a fluorenylene ring.

Preferably, L ₂ is a single bond; Substituted or unsubstituted C _6-12 arylene, more preferably a single bond; Phenylene; Or biphenylylene.

Preferably, L ₃ is a single bond; Or phenylene.

Preferably, Ar ₁ is phenyl or biphenylyl.

Preferably, Ar ₂ is biphenylyl; Dimethylfluorenyl; Or substituted or unsubstituted carbazolyl.

Preferably, Ar ₃ and Ar ₄ are each independently phenyl; Biphenylyl; Naphthyl; Dimethylfluorenyl; Diphenylfluorenyl; Diphenylfluorenyl substituted with methyl; Or N(Ph) ₂ is substituted phenyl.

Preferably, the repeating unit represented by Formula 1 is any one selected from the group consisting of:

On the other hand, the compound represented by Formula 1 is derived from a monomer represented by Formula 1-1:

[Formula 1-1]

In Formula 1-1, R ₁ to R ₄ , X, L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in Formula 1 above.

The compound represented by Formula 1-1 can be prepared by the same method as in Scheme 1 below.

[Scheme 1]

In Reaction Scheme 1, the definitions other than Y and Z are as previously defined, and Y is halogen, preferably bromo or chloro. Z is hydrogen or boron. Reaction Scheme 1 is an amine substitution reaction or a Suzuki reaction, in which a palladium catalyst is reacted in the presence of a base to prepare a compound represented by Formula 1-1. The manufacturing method may be more specific in the manufacturing examples to be described later.

(Polymer)

The polymer according to the present invention can be prepared by polymerizing the monomer represented by Formula 1-1. Preferably, the polymer according to the present invention is a random copolymer comprising the repeating unit.

Preferably, the polymer containing the repeating unit represented by Formula 1 may have a weight average molecular weight of 5,000 to 1,000,000 g/mol, more preferably 5,000 to 300,000 g/mol, or 10,000 to 300,000 g/mol It may have a weight average molecular weight of.

The terminal group of the polymer according to the present invention is a substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted alkyl group, but is not limited thereto.

In the present specification, the terms "weight average molecular weight (Mw)" and "number average molecular weight (Mn)" are converted values for standard polystyrene measured using a gel permeation chromatograph (GPC). In the present specification, the term "molecular weight" means a weight average molecular weight unless otherwise specified.

(Coating composition)

The polymer according to the present invention may form an organic material layer, particularly a hole injection layer or a hole transport layer, of an organic light emitting device by a solution process. To this end, the present invention provides a coating composition comprising the polymer and a solvent according to the present invention described above.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the polymer according to the present invention, and examples include 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, 1,2-hexanediol, etc. Alcohol and its derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Benzoate solvents such as butyl benzoate and methyl-2-methoxybenzoate; Tetralin; Solvents, such as 3-phenoxy-toluene, are mentioned. In addition, the above-described solvent may be used alone or in combination of two or more solvents.

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

In addition, the coating composition may further include one or two or more additives selected from the group consisting of a thermal polymerization initiator and a photopolymerization initiator.

As the thermal polymerization initiator, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methyl cyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide Peroxides such as oxide, bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, or azobis isobutylnitrile, azobisdimethylvaleronitrile, and azobis cyclohexyl nitrile. There is an azo system, but is not limited thereto.

As the photoinitiator, diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenyl ethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4-(2-hydroxyethoxy ) Phenyl-(2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) butanone-1,2-hydroxy-2-methyl-1- Phenyl propan-1-one, 2-methyl-2-morpholino (4-methyl thiophenyl) propan-1-one, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl) Acetophenone-based or ketal-based photopolymerization initiators such as oxime; Benzoin ether photopolymerization initiators such as benzoin, benzoin methyl ether, and benzoin ethyl ether; Benzophenone photopolymerization initiators such as benzophenone, 4-hydroxybenzophenone, 2-benzoylnaphthalene, 4-benzoylbiphenyl, and 4-benzoylphenyl ether; Thioxanthone photoinitiators such as 2-isopropyl thioxanthone, 2-chloro thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, and 2,4-dichloro thioxanthone; And ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide, Other photoinitiators such as bis(2,4-dimethoxy benzoyl)-2,4,4-trimethyl pentylphosphine oxide, but are not limited thereto.

Moreover, what has a photopolymerization accelerating effect may be used alone or in combination with the photopolymerization initiator. For example, triethanolamine, methyldiethanolamine, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, ethyl benzoic acid (2-dimethylamino), 4,4'-dimethylaminobenzophenone, etc. Not limited.

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

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

In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen. In addition, it may further include evaporating a solvent between the coating step and the heat treatment or light treatment step.

(Organic light emitting device)

In addition, the present invention provides an organic light-emitting device including the polymer according to the present invention described above. Specifically, the present invention is a positive electrode; A cathode provided to face the anode; A light-emitting layer provided between the anode and the cathode; And a hole injection layer or a hole transport layer provided between the anode and the emission layer, wherein the hole injection layer or the hole transport layer comprises a polymer according to the present invention.

The structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, and a cathode 5. 2 is composed of a substrate (1), an anode (2), a hole injection layer (6), a hole transport layer (3), a light emitting layer (4), an electron transport layer (7), an electron injection layer (8) and a cathode (5). An example of an organic light emitting device is shown.

The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except that the hole injection layer or the hole transport layer contains the polymer according to the present invention and is manufactured according to the above-described method. have.

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

In addition to such a 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.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SNO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

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

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples of 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

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

In addition, the polymer 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 manufacturing of the polymer and the organic light emitting device including the polymer according to the present invention will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

<Production Example>

<Preparation Example 1>-Preparation of compound 1

1) Synthesis of Intermediate 1-1

Compound I (50 g, 193 mmol) is dissolved in THF (770 mL), replaced with nitrogen, and cooled to 0 ^o C. PhMgBr (3 M ether solution) (97 mL, 289 mmol) was slowly added at 0 ^o C and stirred at room temperature for 3 hours. NH ₄ Cl (aq) was added to terminate the reaction. After the reaction was completed, extraction was performed with ethyl acetate and ammonium chloride solution. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. Intermediate 1-1 obtained by drying the filtrate with a vacuum rotary concentrator was used in the next reaction without further purification.

2) Synthesis of Intermediate 1-2

Intermediate 1-1 (65 g, 193 mmol) was dissolved in DCM (770 mL), substituted with nitrogen, and cooled to 0 ^o C. At 0 ^o C, Et ₃ SiH (4 mL, 289 mmol) was added, and then TFA (23 mL, 301 mmol) was added. After stirring for 2 hours at room temperature. Extracted with dichloromethane and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent. Recrystallized under DCM/Hex conditions to obtain 43 g of Intermediate 1-2.

3) Synthesis of Intermediate 1-3

Intermediate 1-2 (3.21 g, 10 mmol), NaOH (1.2 g, 30 mmol), TBAB (322 mg, 1 mmol) was added to a round bottom flask, followed by nitrogen alicyclic. After adding toluene (20 mL), water (6.4 mL) and 6-bromo-1-hexene (1.6 mL), the mixture was stirred at 120 ^o C for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 3.6 g of Intermediate 1-3.

4) Synthesis of Intermediate 1-4

Compound Ⅱ (2.92 g, 6 mmol), Intermediate 1-3 (2.66 g, 6.6 mmol), Pd(PtBu ₃ ) ₂ (153 mg, 0.3 mmol) and NaOtBu (1.15 g, 12 mmol) in a round bottom flask. Then it was substituted with nitrogen. After adding toluene (30 mL), the mixture was stirred at 90 ^o C for 2 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 4.5 g of Intermediate 1-4.

NMR measured values of Intermediate 1-4: ¹ H NMR (500 MHz, CDCl ₃ ) δ 8.19 (s, 1H), 8.21 (d, 1H), 7.68 (t, 2H), 7.65-7.55 (m, 9H), 7.50-7.40 (m, 8H), 7.34-7.29 (m, 3H), 7.24-7.12 (m, 13H), 5.77-5.69 (m, 1H), 4.95-4.88 (m, 2H), 2.45-2.36 (m , 2H), 1.96-1.90 (m, 2H), 1.35-1.25 (m, 2H), 0.93-0.78 (m, 2H)

5) Synthesis of compound 1

Intermediate 1-4 (809 mg, 1 mmol), Cp ^* TiCl ₃ (2.9 mg, 0.01 mmol) and Ph ₃ CB(C ₆ F ₅ ) ₄ (13.8 mg, 0.015 mmol) in a round bottom flask and nitrogen substitution do. Add toluene (2 mL) and cool to 0 ^o C. From 0 ^o C at iBu ₃ Al (1 M Hex) gave after putting (2 mL, 2 mmol) 70 o C and stirred for 4 hours. After completion of the reaction, it was diluted with THF (5 mL), and extracted with THF, 1% HCl aqueous solution, and Na ₂ CO ₃ aqueous solution. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 550 mg of compound 1. (Mw=106357, Mn=78820)

GPC data of Compound 1 are shown in FIG. 3.

<Production Example 2>-Preparation of compound 2

1) Synthesis of Intermediate 2-1

Compound Ⅲ (3.76 g, 8 mmol) and Cs ₂ CO ₃ (2.6 g, 8 mmol) were put in a round bottom flask, followed by nitrogen substitution. After adding DMF (40 mL) and 6-bromo-1-hexene (1.28 mL, 9.6 mmol), the mixture was stirred at 60 ^o C for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 3.5 g of Intermediate 2-1.

2) Synthesis of Intermediate 2-2

Compound Ⅱ (2.65 g, 5.44 mmol), intermediate 2-1 (3.3 g, 5.98 mmol), Pd(PtBu ₃ ) ₂ (139 mg, 0.272 mmol) and NaOtBu (1.05 g, 10.9 mmol) in a round bottom flask Then it was substituted with nitrogen. After adding toluene (27 mL), the mixture was stirred at 90 ^o C for 2 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 4 g of Intermediate 2-2.

NMR measured values of Intermediate 2-2: ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 8.36 (s, 1H), 8.20 (d, 1H), 7.71 (d, 1H), 7.69-7.58 (m, 10H ), 7.52-7.41 (m, 8H), 7.37-7.30 (m, 4H), 7.28-7.17 (m, 8H), 7.14 (dd, 1H), 7.10-7.06 (m, 4H), 6.73 (d, 2H) ), 4.98 (dd, 1H), 4.92 (dd, 1H), 3.90 (t, 2H), 2.10-2.05 (m, 2H), 1.77-1.71 (m, 2H), 1.54-1.48 (m, 2H), 1.28 (s, 9H)

3) Synthesis of compound 2

Intermediate 2-2 (957 mg, 1 mmol), Cp ^* TiCl ₃ (2.9 mg, 0.01 mmol) and Ph ₃ CB(C ₆ F ₅ ) ₄ (13.8 mg, 0.015 mmol) in a round bottom flask and nitrogen substitution do. Add toluene (2 mL) and cool to 0 ^o C. From 0 ^o C at iBu ₃ Al (1 M Hex) gave after putting (2 mL, 2 mmol) 70 o C and stirred for 4 hours. After completion of the reaction, it was diluted with THF (5 mL), and extracted with THF, 1% HCl aqueous solution, and Na ₂ CO ₃ aqueous solution. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 605 mg of compound 2. (Mw=103204, Mn=45852)

GPC data of Compound 2 is shown in FIG. 4.

<Preparation Example 3>-Preparation of compound 3

1) Synthesis of Intermediate 3-1

Compound IV (4.8 g, 10 mmol), Compound V (5.69 g, 12 mmol), Pd(PPh ₃ ) ₄ (578 mg, 0.5 mmol) and K ₂ CO ₃ (4.15 g. 30 mmol) were added to a round bottom flask. After adding, dissolve in MeOH (5 mL) and THF (5 mL). While maintaining the reaction mixture at room temperature, sodium borohydride (227 mg, 6 mmol) was added little by little, followed by stirring at room temperature for 30 minutes. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to obtain 2.1 g (86% yield) of Intermediate 3-1.

2) Synthesis of Intermediate 3-2

Sodium hydride (60 wt%, 112 mg, 2.8 mmol) was put in a round bottom flask and replaced with a nitrogen atmosphere. After adding anhydrous DMF (3.5 mL), it was cooled to 0°C. A solution of intermediate 3-1 (1.71 g, 1.4 mmol) dissolved in anhydrous DMF (3.5 mL) was slowly added to the reaction mixture, followed by stirring at 0°C for 1 hour. After adding 4-vinylbenzyl chloride (0.39 mL, 2.8 mmol), the temperature was raised to 60°C and stirred for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to blow off the organic solvent, and the residue was purified by column to obtain 1.22 g of Intermediate 3-2.

3) Synthesis of Intermediate 3-3

Substance C (2.62 g, 3.1 mmol) and Cs ₂ CO ₃ (1.0 g, 3.1 mmol) were put in a round bottom flask and replaced with nitrogen. After adding DMF (16 mL) and 6-bromo-1-hexene (0.5 mL, 3.72 mmol), the mixture was stirred at 60 ^o C for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 2.3 g of Intermediate 3-3.

NMR measurement values of Intermediate 3-3: ¹ H NMR (500 MHz, CDCl ₃ ) δ 7.90 (d, 2H), 7.86 (d, 2H), 7.64-7.61 (m, 3H), 7.57-7.55 (m, 3H ), 7.46 (d, 2H), 7.43-7.29 (m, 11H), 7.30 (t, 3H), 7.26-7.23 (m, 1H), 7.20 (d, 1H), 7.16-7.08 (m, 6H), 7.03 (dd, 1H), 6.99 (dd, 2H), 6.78 (t, 2H), 6.73 (d, 2H), 4.98 (dd, 1H), 4.92 (dd, 1H), 3.90 (t, 2H), 2.10 -2.05 (m, 2H), 1.77-1.71 (m, 2H), 1.54-1.48 (m, 2H), 1.39 (s, 6H)

4) Synthesis of compound 3

Intermediate 3-2 (926 mg, 1 mmol), Cp ^* TiCl ₃ (2.9 mg, 0.01 mmol) and Ph ₃ CB (C ₆ F ₅ ) ₄ (13.8 mg, 0.015 mmol) in a round bottom flask and nitrogen substitution do. Add toluene (2 mL) and cool to 0 ^o C. From 0 ^o C at iBu ₃ Al (1 M Hex) gave after putting (2 mL, 2 mmol) 70 o C and stirred for 4 hours. After completion of the reaction, it was diluted with THF (5 mL), and extracted with THF, 1% HCl aqueous solution, and Na ₂ CO ₃ aqueous solution. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 710 mg of compound 3. (Mw=89583, Mn=48220)

GPC data of Compound 3 is shown in FIG. 5.

<Production Example 4>-Preparation of Comparative Compound 1

1) Synthesis of Intermediate 4-1

Add 4-hydroxybenzaldehyde (2.2 g, 18 mmol), 1,4-dibromobutane (4.3 mL, 36 mmol), and K ₂ CO ₃ (5 g, 36 mmol) to a round bottom flask. After adding acetone (54 mL), it was stirred at 90 oC for 4 hours. After completion of the reaction, it was filtered. The filtrate was dried with a vacuum concentrator to remove the organic solvent, and the residue was purified by column to obtain 3.2 g of Intermediate 4-1.

2) Synthesis of Intermediate 4-2

Intermediate 1-2 (3.21 g, 10 mmol), NaOH (1.2 g, 30 mmol), TBAB (322 mg, 1 mmol) was added to a round bottom flask, followed by nitrogen alicyclic. After adding toluene (20 mL), water (6.4 mL) and intermediate 4-1 (3.1 g, 12 mmol), the mixture was stirred at 100 ^o C for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 3.8 g of Intermediate 4-2.

3) Synthesis of Intermediate 4-3

CH ₃ PPh ₃ Br (4.29 g, 12 mmol) and THF (30 mL) were placed in a round bottom flask, replaced with nitrogen, and cooled to 0°C. After adding KOtBu (1.35 g, 12 mmol) to the reaction mixture, it was substituted with nitrogen and stirred at 0°C for 20 minutes. A solution of intermediate 4-2 (2.98 g, 6 mmol) dissolved in THF (30 mL) was slowly added to the reaction mixture, followed by stirring at 0° C. for 40 minutes. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 2.5 g of Intermediate 4-3.

4) Synthesis of Intermediate 4-4

Compound Ⅱ (1.95 g, 4 mmol), intermediate 4-3 (2.18 g, 4.4 mmol), Pd(PtBu ₃ ) ₂ (102 mg, 0.2 mmol) and NaOtBu (769 mg, 8 mmol) in a round bottom flask Then it was substituted with nitrogen. After adding toluene (20 mL), the mixture was stirred at 90 ^o C for 2 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and water. After collecting the organic layer, the organic layer was dried using MgSO ₄ and filtered. The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent, and the residue was purified by column to obtain 3.2 g of Intermediate 4-4.

NMR measured values of Intermediate 4-4: ¹ H NMR (500 MHz, CD ₂ Cl ₂ ) δ 8.32 (s, 1H), 8.17 (d, 1H), 7.68 (t, 2H), 7.64-7.56 (m, 9H ), 7.50-7.40 (m, 8H), 7.35-7.28 (m, 4H), 7.25-7.15 (m, 14H), 6.74 (d, 2H), 6.58 (dd, 2H), 5.52 (d, 1H), 5.05 (d, 1H), 3.89-3.77 (m, 2H), 2.51-2.41 (m, 2H), 1.71-1.66 (m, 2H), 1.54-1.48 (m, 2H)

5) Preparation of Comparative Compound 1

Intermediate 1-4 (973 mg, 0.8 mmol) and azobisisobutyronitrile (1.3 mg, 0.008 mmol) were placed in a round bottom flask and dissolved in anhydrous toluene (1.6 mL) under a nitrogen atmosphere. The mixture was stirred at 70° C. for 6 hours. After completion of the reaction, it was diluted with THF (5 mL) and added to ethyl acetate (70 mL). The precipitate was filtered and washed with ethyl acetate. The obtained solid was dried to give 620 mg (64% yield) of compound 1. (Mw=121423, Mn=49163)

GPC data of Comparative Compound 1 are shown in FIG. 6.

<Example>-Fabrication of an organic light emitting device

[Preparation of ITO substrate]

A glass substrate coated with a thin film of 1,500Å of ITO (indium tin oxide) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.

After washing with distilled water was finished, ultrasonic cleaning was performed with a solvent of isopropyl and acetone, followed by drying, the substrate was washed for 5 minutes, and the substrate was transported to a glove box.

[Device Example 1]

On the ITO transparent electrode, 2wt% toluene ink of the following compound A: the following p dopant (the following formula G) (8:2 by weight) was spin-coated (4000rpm) on the ITO surface and heat-treated at 200°C for 30 minutes to inject holes to a thickness of 40 nm. A layer was formed. Thereafter, Compound 1 was dissolved in toluene at 0.7 wt%, spin-coated on the hole injection layer to form a film at 20 nm, and heated at 200° C. for 30 minutes in a nitrogen atmosphere to form a hole transport layer.

Subsequently, a light emitting layer having a thickness of 20 nm was formed by spin coating 0.5 wt% cyclohexanone ink of the following Compound B: Compound C (92:8 by weight) on the hole transport layer. The following compound D was vacuum-deposited on the light emitting layer to a thickness of 35 nm to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm on the electron injection and transport layer.

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

[Compound A]

[Compound B]

[Compound C]

[Compound D]

[Formula G]

[Device Example 2]

An organic light-emitting device was manufactured in the same manner as in Device Example 1, except that 0.7wt% toluene ink of Compound 2 was used instead of 0.7wt% toluene ink of Compound 1 when forming a hole transport layer in the manufacturing process of Device Example 1. I did.

[Device Example 3]

An organic light-emitting device was manufactured in the same manner as in Device Example 1, except that 0.7wt% toluene ink of Compound 3 was used instead of 0.7wt% toluene ink of Compound 1 when forming a hole transport layer in the manufacturing process of Device Example 1. I did.

[Comparative Device Example 1]

An organic light-emitting device was manufactured in the same manner as in Device Example 1, except that 0.7wt% toluene ink of Comparative Compound 1 was used instead of 0.7wt% toluene ink of Compound 1 when forming a hole transport layer in the manufacturing process of Device Example 1. I did.

[Comparative Element Example 2]

The organic light-emitting device was prepared in the same manner as in Device Example 1, except that 0.7wt% toluene ink of Comparative Compound H was used instead of 0.7wt% toluene ink of Compound 1 when forming a hole transport layer in the manufacturing process of Device Example 1. Was prepared.

[Comparative compound H]

The organic light emitting devices manufactured in Device Example 1, Device Example 2, Device Example 3, Comparative Device Example 1, and Comparative Device Example 2 were subjected to a driving voltage, external quantum efficiency, and a current density of 10 mA/cm ² . The results of measuring luminance and life are shown in Table 1 below. The external quantum efficiency can be calculated as (number of emitted photons)/(number of injected charge carriers), and T95 is a measure of the time to be 95% of the initial luminance at a current density of 10 mA/cm ² .

Volt(V) J (mA/cm ² ) EQE (%) Cd/m ² T95@ 500 nit Device example 1 4.36 10 6.1 120 61 Element example 2 4.20 10 5.8 103 55 Element Example 3 4.25 10 5.8 103 67 Comparative Element Example 1 4.45 10 6.0 118 43 Comparative Element Example 2 7.30 10 0.87 23 One

As shown in Table 1, the organic light emitting devices of Device Examples 1, 2, and 3 using the polymer containing the first unit represented by Formula 1 of the present specification have high efficiency and long lifespan compared to Comparative Device Examples 1 and 2 It can be seen that it can be applied to an organic light-emitting device.

Specifically, it can be seen that, compared to Comparative Device Example 1, Device Examples 1 to 3 increased the life of the device due to the increased stability of the material due to the absence of benzyl hydrogen. In the case of Comparative Device Example 2, it can be seen that the efficiency and lifespan were drastically reduced due to damage to the hole transport layer when the light emitting layer was manufactured because the solvent resistance was not secured.

The present invention is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of the invention, and this also belongs to the scope of the invention.

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

Claims (12)

Polymer comprising a repeating unit represented by the following formula (1):
[Formula 1]

In Formula 1,
R ₁ to R ₃ are each independently hydrogen; Or substituted or unsubstituted C _1-10 alkyl,
R ₄ is substituted or unsubstituted C _1-10 alkyl; Or substituted or unsubstituted C _6-60 aryl,
X is substituted or unsubstituted C _1-60 alkylene; Substituted or unsubstituted C _6-60 arylene; (Substituted or unsubstituted C _1-60 alkylene)-O-; Or (substituted or unsubstituted C _1-60 alkylene)-O-(substituted or unsubstituted C _6-60 arylene),
L ₁ is a single bond; Or substituted or unsubstituted C _6-60 arylene, or combine with R ₄ to form a C _6-60 aryl ring,
L ₂ and L ₃ 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,
Ar ₂ is N(Ar ₃ )(Ar ₄ ); Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
Ar ₃ and Ar ₄ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
n is an integer from 5 to 2,000.
The method of claim 1,
R ₄ is methyl; Or a substituted or unsubstituted phenyl, a polymer.
The method of claim 1,
X is butylene; -(Butylene)-O-; Or -(butylene)-O-phenylene, a polymer.
The method of claim 1,
L ₁ is a single bond; Phenylene; Or R ₄ and bonded to each other to form a fluorenylene ring, a polymer.
The method of claim 1,
L ₂ is a single bond; Phenylene; Or biphenylylene, a polymer.
The method of claim 1,
L ₃ is a single bond; Or phenylene, a polymer.
The method of claim 1,
Ar ₁ is phenyl; Or biphenylyl, a polymer.
The method of claim 1,
Ar ₂ is biphenylyl; Dimethylfluorenyl; Or a substituted or unsubstituted carbazolyl, a polymer.
The method of claim 1,
Ar ₃ and Ar ₄ are each independently phenyl; Biphenylyl; Naphthyl; Dimethylfluorenyl; Diphenylfluorenyl; Diphenylfluorenyl substituted with methyl; Or N(Ph) ₂ is substituted phenyl.
The method of claim 1,
The repeating unit represented by Formula 1 is any one selected from the group consisting of:

The method of claim 1,
The polymer has a weight average molecular weight of 5,000 to 1,000,000 g/mol.
anode; A cathode provided to face the anode; A light-emitting layer provided between the anode and the cathode; And a hole injection layer or a hole transport layer provided between the anode and the light emitting layer, wherein the hole injection layer or the hole transport layer comprises a polymer according to any one of claims 1 to 11 Light-emitting element.

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