KR20200088172A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same, wherein the compound is represented by chemical formula 1. The compound may improve life 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 that converts electrical energy 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, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been 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. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layer structure composed of different materials, for example, 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. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

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

Korean Patent Publication No. 10-2013-073537

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 Formula 1:

[Formula 1]

In Chemical Formula 1,

X is O or S,

Y ₁ , Y ₂ and Y ₃ are each independently CH; Or N, provided that at least two of Y ₁ , Y ₂ and Y ₃ are N,

Ar ₁ , Ar ₂ and Ar ₃ are each independently substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl including at least one hetero atom selected from the group consisting of N, O and S, provided that at least one of Ar ₁ , Ar ₂ and Ar ₃ is further substituted with deuterium,

R ₁ , R ₂ and R ₃ are each independently hydrogen; Or substituted or unsubstituted C _1-60 alkyl,

n is an integer from 0 to 5,

m and o are each independently an integer from 0 to 3.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer provides an organic light emitting device comprising the compound of the present invention described above.

The compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device. In particular, the compound represented by Chemical Formula 1 may be used as a light emitting layer material.

FIG. 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.
FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 It is done.

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

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a linkage to another substituent.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" 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 this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the oxygen of the ester group may be substituted 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 this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a 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 is specifically a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, 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 straight chain or branched chain, and carbon number 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 are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. 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, steelbenyl 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 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 is 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 one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, 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 combine with each other to form a spiro structure. When the fluorenyl group is substituted,

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil 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, thiazolyl group, isooxazolyl Groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups, and dibenzofuranyl groups, but are not limited thereto.

In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an 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, alkylaryl group, and alkylamine group is the same as the above-described alkyl group. In the present specification, heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group among the alkenyl groups is the same as the exemplified alkenyl group. 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 heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.

Preferably, in Formula 1, when one or more of Ar ₁ , Ar ₂ or Ar ₃ is further substituted with deuterium, each of three or more deuterium per ring may be independently substituted.

Preferably, the compound represented by Formula 1 may be any one selected from compounds represented by Formulas 2 to 5 below:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5,

X, Y ₁ , Y ₂ , Y ₃ , Ar ₁ , Ar ₂ , Ar _{3 ,} R ₁ , R ₂ , R ₃ , n, m and o are as defined above.

Preferably, Ar ₁ , Ar ₂ and Ar ₃ are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; It may be dibenzofuranyl or dibenzothiophenyl.

Preferably, R ₁ , R ₂ and R ₃ may be hydrogen or substituted or unsubstituted C _1-10 alkyl.

Preferably, the compound represented by Formula 1 may be any one selected from the group consisting of:

.

.

The compound represented by the formula (1) according to the present invention is a dibenzofuran or dibenzothiophene structure, a monocyclic nitrogen-containing heterocyclic ring as an electron acceptor unit at position 3, and a carbazole group as an electron donor unit at position 2 opposite the other. It has a substituted structure. Each position is the most optimized position to serve as an electron donor and electron acceptor for dibenzofuran or dibenzothiophene, which is advantageous for both electron transport and hole transport, and is driven low through proper charge transport when used as a light emitting layer host. It has the characteristics of voltage and high efficiency. In addition, the structure of Chemical Formula 1 includes a structure in which deuterium is substituted, and since deuterium has a higher atomic weight than hydrogen, the material containing it has a smaller vibration mode than a material containing only hydrogen, which is a non-radioactive decay time in an excited state. To increase the stability of the triplet exciton. Therefore, when a compound represented by Chemical Formula 1 is applied as a phosphorescent host material of a light emitting layer mainly involving triplet excitons, long-term device characteristics can be realized.

The compound represented by Chemical Formula 1 may be prepared through the following Reaction Scheme 1, and may be more specific in the preparation examples described below.

[Scheme 1]

In the above formula, the remaining variables other than Y ₄ and Y ₅ are as defined above, and Y ₄ and Y ₅ are each independently halogen, preferably bromo or chloro.

The preparation of the compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1). In one example, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and an organic light emitting device is provided. do.

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

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport may be represented by Formula 1 It includes the compound displayed.

In addition, the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

Further, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes a compound represented by Chemical Formula 1.

In addition, the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron injection and electron transport includes the compound represented by Chemical Formula 1. In particular, the compound represented by Formula 1 according to the present invention has excellent thermal stability, has a deep HOMO level of 6.0 eV or higher, high triplet energy (ET), and hole stability. In addition, when the compound represented by Chemical Formula 1 is used in an organic material layer capable of electron injection and electron transport at the same time, an n-type dopant used in the art may be mixed and used.

In addition, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.

Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type 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 device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

FIG. 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 Chemical Formula 1 may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

In the organic light emitting device according to the present invention, the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer, and preferably, the light emitting layer may further include a compound represented by Chemical Formula 6:

[Formula 6]

In Chemical Formula 6,

Ar ₄ and Ar ₅ are each independently, substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,

R ₄ and R ₅ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,

a and b are each independently an integer from 0 to 7.

Preferably, Ar ₄ and Ar ₅ are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Dibenzofuranyl; Dibenzothiophenyl; Or dimethylfluorenyl.

Preferably R ₄ and R ₅ may be hydrogen.

Preferably, the compound represented by Formula 6 may be any one selected from the group consisting of:

.

.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. Further, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

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

In addition, the compound represented by Chemical Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode 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.

The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode 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 metal and oxide such as ZnO:Al or SNO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into an 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 is a multilayer structure 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 an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability 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 substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

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

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material 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, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including 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 or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an 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 forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds and nitrogen-containing 5-membered ring derivatives, but are 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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

In addition, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

[ Synthetic example ]

Synthetic example 1: Synthesis of Intermediate Compound 1-1

Dissolve 2-bromo-7-chlorodibenzo[b,d]furan (20.0g, 71.0mmol) and intermediate a-1 (21.8g, 74.6mmol) in THF 300ml in a 3-neck flask and potassium carbonate (39.3g, 284.2mmol) Is dissolved in 100 ml of H2O. Tetrakis(triphenylphosphine)palladium(0) (4.1g, 3.6mmol) was added thereto, and the mixture was stirred under an argon atmosphere under reflux for 8 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with ethyl acetate. After drying the extract with MgSO 4, filtering and concentration, the sample was purified by silica gel column chromatography to obtain 25.2 g of Compound 1-1. (Yield 79%, MS[M+H]+= 448)

Synthetic example 2: Synthesis of Intermediate Compound 1-2

Compound 1-1 (25.0 g, 55.7 mmol), Bis (pinacolato)diboron (17.0 g, 66.8 mmol), Bis(dibenzylideneacetone) palladium(0) (0.6 g, 1.1 mmol), Tricyclohexylphosphine (0.6 g, 2.2 mmol), Potassium acetate (10.9 g, 111.4 mmol), 1,4-dioxane 375 ml was added, and the mixture was stirred for 12 hours under argon atmosphere reflux conditions. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, water was added, and the mixture was extracted with ethyl acetate. After the extract was dried over MgSO 4, filtered and concentrated, the sample was purified by silica gel column chromatography to obtain compound 1-2. (20.5 g, yield 68%, MS: [M+H] + = 540)

Example 1: Synthesis of Compound 1

Compound 1-2 (20.0g, 37.0mmol) and intermediate b-1 (11.4g, 38.9mmol) were dissolved in 300 ml of THF and potassium carbonate (20.5g, 148.0mmol) was dissolved in 100ml of H2O in a three-necked flask. (triphenylphosphine)palladium(0) (2.1g, 1.9mmol) was added, and the mixture was stirred for 8 hours under argon atmosphere reflux.After the reaction was cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with ethyl acetate. After drying the extract with MgSO 4, filtering and concentrating, the sample was purified by silica gel column chromatography, and then 7.6 g of Compound 1 was obtained through a sublimation tablet (yield 32%, MS[M+H]+). = 645)

Example 2: Synthesis of Compound 2

In Synthesis Example 1, Compound 2 was prepared by the same method as the method for preparing Compound 1, except that Intermediate a-1 was changed to Intermediate a-2 and Intermediate b-1 was changed to Intermediate b-2. (MS[M+H] ⁺ = 650)

Example 3: Synthesis of Compound 3

In Synthesis Example 1, compound 3 was prepared by the same method as the method for preparing compound 1, except that intermediate a-1 was changed to intermediate a-3 and intermediate b-1 was changed to intermediate b-2. (MS[M+H] ⁺ = 740)

Example 4: Synthesis of Compound 4

In Synthesis Example 1, compound 4 was prepared by the same method as the method for preparing compound 1, except that intermediate a-1 was changed to intermediate a-4 and intermediate b-1 was changed to intermediate b-3. (MS[M+H] ⁺ = 751)

Example 5: Synthesis of Compound 5

In Synthesis Example 1, 2-bromo-7-chlorodibenzo[b,d]furan is 2-bromo-7-chlorodibenzo[b,d]thiophene, intermediate a-1 is intermediate a-5, and intermediate b-1 is Compound 5 was prepared by the same method as the method of preparing compound 1, except that it was changed to intermediate b-4 and used. (MS[M+H] ⁺ = 751)

[ Experimental Example ]

Experimental Example One

ITO (Indium Tin Oxide) was coated with a thin film coated with a thickness of 1,400 Å in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

The following HT and 5 wt% PD were thermally vacuum-deposited to a thickness of 100 로 on the prepared ITO transparent electrode, and then, only the HT material was deposited to a thickness of 1150 Å to form a hole transport layer. The following EB as an electron blocking layer was thermally vacuum-deposited to a thickness of 450 MPa. Subsequently, compound 1 and 15% by weight of GD were used as a dopant and vacuum-deposited to a thickness of 400 MPa. Subsequently, the following ET-A was vacuum-deposited to a thickness of 50 MPa as a hole blocking layer. Subsequently, ET-B and Liq as the electron transporting and injection layers were thermally vacuum-deposited at a thickness of 250 MPa at a ratio of 2:1, and then LiF and magnesium were vacuum-deposited at a thickness of 30 MPa at a ratio of 1:1. Magnesium and silver were deposited on the electron injection layer at a thickness of 160 로 at a ratio of 1:4 to form a cathode to prepare an organic light emitting device.

By applying a current to the produced organic light emitting device, voltage, efficiency, life (T95) was measured and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10mA/cm ² , and T95 is the time until the initial luminance decreases to 95% at the current density of 20mA/cm ² .

Experimental Example 2-10 and comparison Experimental Example 1 to 6

The organic light emitting devices of Experimental Examples 2 to 10 and Comparative Experimental Examples 1 to 6 were manufactured using the same method as in Experimental Example 1, except that the host material was changed as shown in Table 1 below. In this case, when a mixture of two types of compounds is used as the host, the parentheses indicate the weight ratio between the host compounds.

division Host
matter @ 10mA/cm ² @ 20mA/cm ² Voltage
(V) efficiency
(cd/A) life span
(T95, hr) Experimental Example 1 Compound 1 4.68 47.5 120 Experimental Example 2 Compound 2 4.65 47.2 125 Experimental Example 3 Compound 3 4.63 47.0 115 Experimental Example 4 Compound 4 4.62 48.3 130 Experimental Example 5 Compound 5 4.70 49.2 120 Experimental Example 6 PGH: Compound 1 (60:40) 4.45 53.5 175 Experimental Example 7 PGH:Compound 2 (60:40) 4.49 54.1 180 Experimental Example 8 PGH:Compound 3 (60:40) 4.43 54.3 180 Experimental Example 9 PGH:Compound 4 (60:40) 4.38 55.5 170 Experimental Example 10 PGH:Compound 5 (60:40) 4.47 56.1 175 Comparative Experimental Example 1 GH-A 4.70 47.5 95 Comparative Experimental Example 2 GH-B 6.31 28.1 20 Comparative Experimental Example 3 GH-C 5.38 35.0 90 Comparative Experimental Example 4 GH-D 5.39 41.1 95 Comparative Experimental Example 5 PGH:GH-A (60:40) 4.43 53.2 150 Comparative Experimental Example 6 PGH:GH-C(60:40) 5.27 40.5 110

As shown in Table 1, when using the compound of Formula 1 as a host for an organic electroluminescent device, it can be seen that it exhibits characteristics of low voltage, high efficiency, and long life compared to GH-B to GH-D having different connection positions. In particular, it can be seen that the lifespan is increased by deuterium substitution when compared with Compound 1 and GH-A. In addition, when used in combination with a compound of Formula 6, such as PGH, the effect becomes more remarkable, and exhibits a better effect than when a compound of a different structure is used by mixing with a compound of Formula 6.

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

Claims (12)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
X is O or S,
Y ₁ , Y ₂ and Y ₃ are each independently CH; Or N, provided that at least two of Y ₁ , Y ₂ and Y- ₃ are N,
Ar ₁ , Ar ₂ and Ar ₃ are each independently, substituted or unsubstituted C _6-60 aryl; Or C _5-60 heteroaryl including at least one hetero atom selected from the group consisting of N, O and S, provided that at least one of Ar ₁ , Ar ₂ and Ar ₃ is further substituted with deuterium,
R ₁ , R ₂ and R ₃ are each independently hydrogen; Or substituted or unsubstituted C _1-60 alkyl,
n is an integer from 0 to 5,
m and o are each independently an integer from 0 to 3.

According to claim 1,
When at least one of Ar ₁ , Ar ₂ and Ar ₃ is further substituted with deuterium, each independently 3 or more deuterium per ring is substituted.
According to claim 1,
The compound represented by Formula 1 is any one selected from compounds represented by Formulas 2 to 5 below:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5,
X, Y ₁ , Y ₂ , Y ₃ , Ar ₁ , Ar ₂ , Ar _{3 ,} R ₁ , R ₂ , R ₃ , n, m and o are as defined in claim 1.
According to claim 1,
Ar ₁ , Ar ₂ and Ar ₃ are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Anthracenyl; Phenanthrenyl; Triphenylenyl; Dimethylfluorenyl; Dibenzofuranyl; Or dibenzothiophenyl.
According to claim 1,
R ₁ , R ₂ and R ₃ are each independently hydrogen; Or substituted or unsubstituted C _1-10 alkyl.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:

.
A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 6. That is, an organic light emitting device.
The method of claim 7,
The organic material layer including the compound is an organic light emitting device.
The method of claim 8,
The light emitting layer further comprises a compound represented by the formula (6), an organic light emitting device:
[Formula 6]

In Chemical Formula 6,
Ar ₄ and Ar ₅ are each independently, substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
R ₄ and R ₅ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
a and b are each independently an integer from 0 to 7.
The method of claim 9,
Ar ₄ and Ar ₅ are each independently phenyl; Biphenylyl; Terphenylyl; Naphthyl; Dibenzofuranyl; Dibenzothiophenyl; Or dimethyl fluorenyl, an organic light emitting device.
The method of claim 9,
R ₄ and R ₅ are hydrogen, the organic light emitting device.
The method of claim 9,
The compound represented by Chemical Formula 6 is any one selected from the group consisting of:

.

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