KR102107199B1 - Organic light emitting device - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light emitting device using the same.

Description

Organic light emitting device {Organic light emitting device}

The present invention relates to an organic light emitting device capable of lowering a driving voltage and improving efficiency, thermal stability, and life.

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 provided 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-layered 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 the 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. 10-2000-0051826

The present invention relates to an organic light emitting device capable of lowering a driving voltage and improving efficiency, thermal stability, and life.

The present invention is a cathode; anode; And at least one organic layer provided between the cathode and the anode,

The one or more organic material layers provide an organic light emitting device including at least one compound selected from the group consisting of compounds represented by the following Chemical Formulas 1 and 2.

[Formula 1]

[Formula 2]

In Chemical Formulas 1 and 2,

X ₁ and X ₂ are each independently N or CR ', provided that at least one of them is N,

R 'is hydrogen; Or substituted or unsubstituted C _1-60 alkyl,

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

The organic light-emitting device including the compound represented by Chemical Formulas 1 and / or 2 in the organic material layer may lower a driving voltage and improve efficiency, thermal stability, and life.

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.
Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (3), electron transport layer (8), electron injection layer (9) And an example of an organic light-emitting device comprising the cathode 4.
3 is a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 10, an electron blocking layer 7, a first light emitting layer 11, a first electron transport layer 12, An organic light-emitting device comprising an N-type charge generation layer 13, a P-type charge generation layer 14, a second hole transport layer 15, a second emission layer 16, a second electron transport layer 17, and a cathode 4 It is an example of.

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

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a linkage to another substituent.

The term "substituted or unsubstituted" as used herein refers to 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.

* The carbon number of the carbonyl group in the present specification 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 linear or branched, 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, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl 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, isooxazolyl group, tiadiia A sleepy group, a phenothiazinyl group and a dibenzofuranyl group, and the like, 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 exemplified aryl group. 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, the description of the heteroaryl group among heteroarylamines may be applied. In the present specification, the alkenyl group in the alkenyl group 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.

Hereinafter, various embodiments of the present invention will be described in detail with reference to the accompanying drawings.

1 to 3 show an example of the organic light emitting device of the present invention.

Referring to FIG. 1, the organic light emitting device of the present invention may include a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

Referring to FIG. 2, the organic light emitting device of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, and an electron transport layer (8), an electron injection layer 9 and a cathode 4 may be included.

Referring to FIG. 3, the organic light emitting device of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 10, an electron blocking layer 7, and a first light emitting layer 11 ), The first electron transport layer 12, the N-type charge generation layer 13, the P-type charge generation layer 14, the second hole transport layer 15, the second light emitting layer 16, the second electron transport layer 17 And a cathode 4.

The anode 2 is an electrode for injecting holes and may be any one of indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (ZnO). In addition, when the anode is a reflective electrode, the anode may further include a reflective layer made of any one of aluminum (Al), silver (Ag), or nickel (Ni) under a layer made of any one of ITO, IZO, or ZnO.

One or more organic material layers may be formed on the anode 2.

The organic material layer of the present invention may include one or more compounds selected from the group consisting of compounds represented by the following Chemical Formulas 1 and 2.

[Formula 1]

[Formula 2]

In Chemical Formulas 1 and 2,

X ₁ and X ₂ are each independently N or CR ', provided that at least one of them is N,

R 'is hydrogen; Or substituted or unsubstituted C _1-60 alkyl,

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

The organic material layer may be formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, an electron injection layer 9, an electron transport layer 8, an electron injection and electron transport layer, It may be made of a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, and the like.

In addition, the organic material layer may include two or more light-emitting layers 3, and a charge generation layer including an N-type electron generation layer 13 and a P-type hole generation layer 14 may be provided between the two or more light-emitting layers. Can be.

Preferably, at least one compound selected from the group consisting of compounds represented by Formulas 1 and 2 may be included in the hole injection layer 5, for example, the compound may be included as a dopant in the hole injection layer.

In addition, at least one compound selected from the group consisting of the compounds represented by Formulas 1 and 2 may be included in the P-type hole generating layer 14, for example, the compound may be included as a dopant in the P-type hole generating layer. have.

The compound contained in the hole injection layer 5 should include a strong electron withdrawing substituent, but such a compound is difficult to develop due to the material synthesis is difficult due to the electron withdrawing substituent and the heat and deposition stability are weak. However, the compound of the present invention can facilitate synthesis and deposition of the compound by including cyclopentapyridine as a core capable of securing process stability such as heat or vapor deposition. In addition, the compound of the present invention includes an electron withdrawing substituent attached to the core, thereby increasing electron affinity, thereby increasing the amount and concentration of holes generated in the adjacent hole injection layer and hole transport layer 6 to provide a low-voltage and high-efficiency glass electronic device. Can provide.

Meanwhile, the hole transport layer 6 is a layer that receives holes from the hole injection layer 5 and transports holes to the light emitting layer 3. Therefore, since a material capable of transporting holes from the anode 2 or the hole injection layer to the light emitting layer is used as the hole transporting material included in the hole transporting layer, a material having high mobility for holes is required.

The Chemical Formula 1 may be any one selected from compounds represented by the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1 to 1-3,

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

The Chemical Formula 2 may be a compound represented by the following Chemical Formula 2-1 or 2-2.

[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

Preferably, A and B can be cyano.

Preferably, R ₂ and R ₃ may be cyano.

Preferably, R ₁ and R ₄ may each independently be any one selected from the group consisting of:

R ' ₁ to R' ₅ are each independently hydrogen, cyano, fluorine, trifluoromethyl, or trifluoromethoxy,

Y ₁ to Y ₃ are each independently N or CH, provided that at least one of them may be N.

The compound represented by Formula 1 may be any one selected from the group consisting of the following compounds.

The compound represented by Chemical Formula 1 may be prepared by the following Reaction Scheme 1.

[Scheme 1]

In Reaction Scheme 1, description of X ₁ , X ₂ , R ₁ to R ₄ , A and B is as defined in Chemical Formula 1.

The compound represented by Formula 2 may be any one selected from the group consisting of the following compounds.

The compound represented by Chemical Formula 2 may be prepared by the same method as in Scheme 2 below.

[Scheme 2]

In Reaction Scheme 2, description of X ₁ , X ₂ , R ₁ to R ₄ , A and B is as defined in Chemical Formula 1.

The organic layer may further include a compound represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

X, Y and Z are each independently substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing one or more of O, N, Si and S.

The compound represented by Chemical Formula 3 may be any one selected from the group consisting of the following compounds.

In the organic light emitting device of the present invention, a hole injection layer 5 may be formed on the anode 2. The hole injection layer is made of a hole injection material, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode 2, an excellent hole injection effect for the light emitting layer 3 or the light emitting material, A compound that prevents movement of the excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also 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.

In addition, a hole transport layer 6 may be formed on the hole injection layer 5, and a light emitting layer 3 may be formed on the hole transport layer 6. The emission layer may emit red (R), green (G), or blue (B), and may be made of a fluorescent material or a phosphorescent material.

The organic light emitting device according to the present invention, materials and methods known in the art, except that at least one layer of the organic material layer includes at least one compound selected from the group consisting of compounds represented by Formulas 1 and 2 Can be manufactured. 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 can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate 1. At this time, an anode (2) is deposited 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. ), And an organic material layer including a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, and an electron transport layer 8 is formed thereon, which can be used as a cathode 4 thereon. It can be prepared by depositing a material. 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 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the 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 this 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 the substrate 1 (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode 2, the second electrode is a cathode 4, 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 negative electrode 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 material is a layer for injecting holes from an electrode, and the hole injection material has the ability to transport holes, so a hole injection effect in the anode 2, an excellent hole injection effect for the light emitting layer 3 or the light emitting material It is preferable to have a compound having an exciton generated in the light emitting layer and preventing migration to the electron injection layer or electron injection material, and also having excellent thin film formation ability. 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 matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer 6 is a layer that receives holes from the hole injection layer 5 and transports holes to the light emitting layer 3, and the hole transport material receives holes from the anode 2 or the hole injection layer and moves them to the light emitting layer. It is preferred to include compounds that can be given.

The light-emitting material is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer 6 and the electron transport layer 8, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Do. 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) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer 3 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 arylamino groups such as pyrene, anthracene, chrysene, periplanten, and the substituted or unsubstituted 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, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer 3. As the electron transporting material, electrons are well injected from the cathode 4 and transferred to the light emitting layer. Materials with large mobility for are suitable. 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 to these. The electron transport layer 8 can be used with any desired cathode material, as used according to the prior art. In particular, examples of suitable cathode materials are those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.

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 4, an excellent electron injection effect on the light emitting layer 3 or the light emitting material, A compound that prevents movement of the generated excitons into the hole injection layer 5 and has excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, 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.

Hereinafter, preferred embodiments are presented to help understanding of the invention. However, the following examples are only for illustrating the present invention, and the present invention is not limited thereto.

Manufacturing example  1: Synthesis of Compound 1

Step 1) Synthesis of Compound 1-1

2,2 '-(3,5-dibromopyridine-2,6-diyl) diacetonitrile (50g, 15.87mmol) in cupper iodide (2.4g, 1.269mmol), isopropyl in a 1000ml round bottom flask Amine (54.5ml, 63.49mmol), tetrakis (triphenylphosphine) palladium (0) (7.3g, 0.634mmol) was added, dissolved in toluene (500ml), and heated and stirred. After heating and stirring for 10 minutes, 1-ethynyl-3,5-bis (trifluoromethyl) benzene (84.2ml, 47.61mmol) was dissolved in toluene (100ml) and slowly added dropwise.

After completion of the reaction, 80% of toluene was distilled and solidified by adding anhydrous ethanol. This was filtered, dissolved in chloroform, stirred with water for 10 minutes, and the organic layers were collected, dried over anhydrous magnesium, and filtered. The organic layer was distilled under reduced pressure, then solidified with anhydrous ethanol and filtered to obtain compound 1-1 (60 g, yield 60%). MS [M + H] ⁺ = 629

Step 2) Synthesis of Compound 1-2

Compound 1-1 (30 g, 4.766 mmol), palladium chloride (PdCl ₂ ) (1.7 g, 0.953 mmol), silver hexafluoroantimonate (AgSbF ₆ ) (3.27 g, 0.953 mmol), D in a 500 ml round bottom flask After dissolving phenyl sulfoxide (Ph ₂ SO) (57.8 g, 28.59 mmol) in dichloroethylene (DCE), stir at 60 ° C. for 12 hours, add cesium carbonate (Cs ₂ CO ₃ ) (9.532 mmol) for 12 hours. It was stirred. After extracting with dichloromethane (CH ₂ Cl ₂₎ After completion of the reaction dichloromethane (CH ₂ Cl ₂₎ to all into a 35% hydrochloric acid (HCl) and stirred for 2 hours after the shot. After extraction with dichloromethane / ammonium chloride aqueous solution (CH ₂ Cl ₂ /aq.NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate (MgSO ₄ ), and the organic layers were collected and concentrated under reduced pressure. Thereafter, column 1-2 was used to obtain compound 1-2 (13 g, yield 41.5%). MS [M + H] ⁺ = 657

Step 3) Synthesis of Compound 1

In a 500 ml round bottom flask, compound 1-2 (10 g, 1.521 mmol), malononitrile (3.041 mmol) and dichloromethane solvent and stirred for 30 minutes under argon conditions. After cooling to 0 ° C and stirring for 10 minutes, titanium tetrachloride (TiCl ₄ ) (8.45ml, 6.084mol) was slowly added, then pyridine (7.35ml, 9.126mmol) was added, and the temperature was slowly increased at room temperature at 0 ° C. The mixture was stirred at room temperature for 2 hours. After extraction with an aqueous dichloromethane / ammonium chloride solution (CH ₂ Cl ₂ /aq.NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate, and the organic layers were collected and distilled under reduced pressure to yield Compound 1 (6 g, yield). 52.35%). MS [M + H] ⁺ = 753

Manufacturing example  2: Synthesis of Compound 2

Step 1) Synthesis of Compound 2-1

2,2 '-(2,6-dibromopyridine-3,5-diyl) diacetonitrile (50g, 15.87mmol) in a 1000ml round-bottomed flask with copper isideide (2.4g, 1.269mmol), isopropylamine (54.5ml, 63.49mmol), tetrakis (triphenylphosphine) palladium (0) (7.3g, 0.634mmol) was added, dissolved in toluene (500ml), and heated and stirred. After heating and stirring for 10 minutes, 4-ethynyl-2- (trifluoromethyl) benzonitrile (92.9g, 47.61mmol) was dissolved in toluene (100ml) and slowly added dropwise. After completion of the reaction, 80% of toluene was distilled and solidified by adding anhydrous ethanol. After filtering and dissolving in chloroform, the mixture was stirred with water for 10 minutes. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the organic layer was distilled under reduced pressure and then solidified with anhydrous ethanol to obtain compound 2-1 (53 g, yield 61.6%). MS [M + H] ⁺ = 543

Step 2) Synthesis of Compound 2

Compound 2 (4 g, yield: 69%) was obtained in the same manner as in Steps 2 and 3 of Preparation Example 1, except that Compound 2-1 prepared above was used instead of Compound 1-1. MS [M + H] ⁺ = 667

Manufacturing example  3: Synthesis of Compound 3

Step 1) Synthesis of Compound 3-1

2,2 '-(3,5-dibromopyrazine-2,6-diyl) diacetonitrile (50g, 15.82mmol) in a 1000ml round-bottomed flask, copper iodide (2.4g, 1.269mmol), isopropyl Amine (54.5ml, 63.49mmol), tetrakis (triphenylphosphine) palladium (0) (7.3g, 0.634mmol) was added thereto, dissolved in toluene (500ml), and heated and stirred. After stirring for 10 minutes, 4-ethynyl-2,6-difluorobenzonitrile (77.4g, 47.46mmol) was dissolved in toluene (100ml) and slowly added dropwise. After completion of the reaction, 80% of toluene was distilled and solidified by adding anhydrous ethanol. After filtering and dissolving in chloroform, the mixture was stirred with water for 10 minutes. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the organic layer was distilled under reduced pressure and then solidified with anhydrous ethanol to filter to obtain compound 3-1 (48 g, yield 63%). MS [M + H] ⁺ = 480

Step 2) Synthesis of Compound 3

Compound 3 (3.2 g, yield 71%) was obtained in the same manner as in Steps 2 and 3 of Preparation Example 1, except that Compound 3-1 was used instead of Compound 1-1. MS [M + H] ⁺ = 604

Manufacturing example  4: Synthesis of Compound 4

Step 1) Synthesis of Compound 4-1

2,2 '-(3,6-dibromopyridine-2,5-diyl) diacetonitrile (50g, 15.87mmol) in cupper iodide (2.4g, 1.269mmol), isopropyl in a 1000ml round bottom flask Amine (54.5ml, 63.49mmol), tetrakis (triphenylphosphine) palladium (0) (7.3g, 0.634mmol) was added, dissolved in toluene (500ml), and heated and stirred. After heating and stirring for 10 minutes, 4-ethynyl-2- (trifluoromethoxy) benzonitrile (100.5g, 47.62mmol) was dissolved in toluene (100ml) and slowly added dropwise. After completion of the reaction, 80% of toluene was distilled and solidified by adding anhydrous ethanol. Filtration, dissolved in chloroform, stirred with water for 10 minutes, the organic layers were collected, dried over anhydrous magnesium, filtered, and the organic layer was distilled under reduced pressure, and then solidified with anhydrous ethanol to filter. Compound 4-1 (52 g, yield 57) %). MS [M + H] ⁺ = 575

Step 2) Synthesis of Compound 4-2

Compound 4-1 (30 g, 5.213 mmol), palladium chloride (PdCl ₂ ) (1.84 g, 1.042 mmol), silver hexafluoroantimonate (AgSbF ₆ ) (3.58 g, 1.042 mmol), D in a 500 ml round bottom flask After dissolving phenyl sulfoxide (Ph ₂ SO) (12.6g, 6.252mmol) in dichloroethylene (DCE), stir for 12 hours at 60 ℃ and add cesium carbonate (Cs ₂ CO ₃ ) (6.79g, 2.084mmol) Stir for 12 hours. After extracting with dichloromethane (CH ₂ Cl ₂₎ After completion of the reaction dichloromethane (CH ₂ Cl ₂₎ to all into a 35% hydrochloric acid (HCl) and stirred for 2 hours after the shot. After extraction with dichloromethane / ammonium chloride aqueous solution (CH2Cl2 / aq.NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate (MgSO ₄ ), and the organic layers were collected and concentrated under reduced pressure. Thereafter, column 4 was used to obtain compound 4-2 (13 g, yield 43.6%). MS [M + H] ⁺ = 603

Step 3) Synthesis of Compound 4

In a 500 ml round bottom flask, compound 4-2 (10 g, 1.658 mmol), malononitrile (2.19 g, 3.316 mmol) and dichloromethane solvent and stirred for 30 minutes under argon conditions. After cooling to 0 ° C and stirring for 10 minutes, titanium tetrachloride (TiCl ₄ ) (7.27ml, 6.632mol) was slowly added, pyridine (10.68ml, 13.264mmol) was added, and the temperature was slowly increased at room temperature at 0 ° C. The mixture was stirred at room temperature for 2 hours. After extraction with an aqueous dichloromethane / ammonium chloride solution (CH ₂ Cl ₂ /aq.NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate, and the organic layers were collected and distilled under reduced pressure to obtain compound 4 (7 g, yield) 60.39%). MS [M + H] ⁺ = 699

Manufacturing example  5: Synthesis of Compound 5

Step 1) Synthesis of Compound 5-1

2,2 '-(2,6-dibromopyridine-3,5-diyl) diacetonitrile (50g, 15.87mmol) in cupper iodide (2.4g, 1.269mmol), isopropyl in a 1000ml round bottom flask Amine (54.5ml, 63.49mmol), tetrakis (triphenylphosphine) palladium (0) (7.3g, 0.634mmol) was added, dissolved in toluene (500ml), and heated and stirred. After stirring for 10 minutes, 3-ethynyl-5- (trifluoromethyl) benzonitrile (92.9g, 47.61mmol) was dissolved in toluene (100ml) and slowly added dropwise. After completion of the reaction, 80% of toluene was distilled and solidified by adding anhydrous ethanol. Filtration, dissolved in chloroform, stirred with water for 10 minutes, the organic layers were collected, dried over anhydrous magnesium, filtered, and the organic layer was distilled under reduced pressure, then solidified with anhydrous ethanol, filtered to obtain compound 5-1 (50 g, yield) 58.0%). MS [M + H] ⁺ = 543

Step 2) Synthesis of Compound 5

Compound 5 (4 g, yield: 69%) was obtained in the same manner as in Steps 2 and 3 of Preparation Example 4, except that Compound 5-1 prepared above was used instead of Compound 4-1. MS [M + H] ⁺ = 667

Manufacturing example  6: Compound 6 of  synthesis

Step 1) Synthesis of Compound 6-1

2,2 '-(3,6-dibromopyrazine-2,5-diyl) diacetonitrile (50g, 15.82mmol) in a 1000ml round-bottom flask, copper iodide (2.4g, 1.269mmol), isopropyl Amine (54.5ml, 63.49mmol), tetrakis (triphenylphosphine) palladium (0) (7.3g, 0.634mmol) was added, dissolved in toluene (500ml), and heated and stirred. After heating and stirring for 10 minutes, 4-ethynyl-2,6-difluorobonzonitrile (77.4g, 47.46mmol) was dissolved in toluene (100ml) and slowly added dropwise. After completion of the reaction, 80% of toluene was distilled and solidified by adding anhydrous ethanol. Filtration, dissolved in chloroform, stirred with water for 10 minutes, the organic layers were collected, dried over anhydrous magnesium, filtered, and the organic layer was distilled under reduced pressure, then solidified with anhydrous ethanol, filtered to obtain compound 6-1 (50 g, yield) 65.78%). MS [M + H] ⁺ = 480

Step 2) Synthesis of Compound 6-2

Compound 6 (3.5 g, yield 72%) was obtained by the same method as steps 2 and 3 of Preparation Example 4, except that Compound 6-1 prepared above was used instead of Compound 4-1. MS [M + H] ⁺ = 604

Example  1-1

의 두께로 박막 코팅된 유리기판을 세제에 녹인 증류수에 넣고 초음파로 세척하였다. 이때 세제로는 피셔사(Fischer Co.)의 Decon™ CON705 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 0.22㎛ sterilizing filter로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필 알코올, 아세톤 및 메탄올의 용제로 각각 10분간 초음파 세척하고, 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후, 진공 증착기로 기판을 수송시켰다.ITO (Indium Tin Oxide) is 1,400

The glass substrate coated with a thin film was put in distilled water dissolved in detergent and washed with ultrasonic waves. At this time, Decon ™ CON705 manufactured by Fisher Co. was used as a detergent, and distilled water filtered second by a 0.22 μm sterilizing filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes with distilled water. After washing with distilled water, ultrasonic cleaning was performed for 10 minutes each with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, the following HT-A and compound 1 (dopant) were thermally vacuum-deposited to a thickness of 100: at a weight ratio of 95: 5 to form a hole injection layer. Then, only the HT-A material was deposited at a thickness of 1100 정 to form a hole. A transport layer was formed. A compound represented by the following EB-A as an electron blocking layer was thermally vacuum-deposited to a thickness of 50 Pa. Subsequently, a compound represented by the following BH-A and BD-A as a light emitting layer was vacuum deposited to a thickness of 200 Pa in a weight ratio of 96: 4. Subsequently, the compound represented by ET-A and Liq as the electron transport layer was thermally vacuum-deposited to a thickness of 360 Å at a weight ratio of 1: 1, and then the compound represented by Liq was vacuum-deposited to a thickness of 5 형성 to form an electron injection layer. Did. On the electron injection layer, magnesium and silver were sequentially deposited at a weight ratio of 10: 1 to a thickness of 220 Å and aluminum to a thickness of 1000 형성 to form a cathode, thereby producing an organic light emitting device.

Example  1-2 to 1-6 and Comparative example  1-1 to 1-4

An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compounds described in Table 1 below instead of HT-A and compound 1 in Example 1-1. In Table 1 below, the parentheses correspond to the weight ratio of each compound, and the lesser compound corresponds to the dopant.

Table 2 shows the results obtained by measuring the voltage and efficiency when a current density of 10 mA / cm ² was applied to the organic light emitting device manufactured in the above Examples and Comparative Examples.

Hole injection layer Voltage (V) Efficiency (cd / A) Example 1-1 HT-A: Compound 1 (95: 5) 4.83 6.21 Example 1-2 HT-A: Compound 2 (95: 5) 4.80 6.32 Example 1-3 HT-A: Compound 3 (95: 5) 4.55 6.57 Example 1-4 HT-A: Compound 4 (95: 5) 4.21 6.80 Example 1-5 HT-A: Compound 5 (95: 5) 4.20 6.82 Example 1-6 HT-A: Compound 6 (95: 5) 3.92 7.23 Comparative Example 1-1 HT-A: HAT-CN (95: 5) 6.23 4.88 Comparative Example 1-2 HT-A 8.52 2.13 Comparative Example 1-3 HT-A: Compound A (95: 5) 5.12 5.85 Comparative Example 1-4 HT-A: Compound B (95: 5) 5.13 5.90

Each compound in Table 1 is as follows.

As shown in Table 1, it was confirmed that the compounds represented by Chemical Formulas 1 and 2 of the present invention have a significantly lower voltage and significantly better efficiency when used as a dopant in a hole injection layer.

Example  2-1

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 에 was placed 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 cleaning was repeated twice for 10 minutes 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, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

The HAT-CN was thermally vacuum-deposited to a thickness of 50 MPa on the prepared ITO transparent electrode to form a hole injection layer, and then the following NPB was vacuum-deposited to a thickness of 100 MPa to form a first hole transport layer. Subsequently, the following EB-B was vacuum-deposited to a thickness of 100 mm 2 on the first hole transport layer to form an electron blocking layer. Subsequently, the first luminescent layer was formed by vacuum-depositing the following YGH-A, YGH-B and YGD at a weight ratio of 2: 2: 1 on the electron blocking layer with a thickness of 400 mm 2. Subsequently, the first ET-B was vacuum-deposited to a thickness of 250 MPa on the first light emitting layer to form a first electron transport layer. Subsequently, the following NCG and Li (Lithium) were vacuum-deposited at a weight ratio of 50: 1 on the first electron transport layer to form an N-type charge generation layer with a thickness of 100 Pa.

Subsequently, HT-A and Compound 1 (dopant) were vacuum-deposited at a weight ratio of 70:30 to form a P-type charge generating layer with a thickness of 100 Å, and only HT-A was further vacuum-deposited to a thickness of 800 을 to form a second hole transport layer. Formed. Subsequently, a compound represented by the following BH-B and BD-B as a second light emitting layer was vacuum-deposited to a thickness of 250 MPa at a weight ratio of 96: 4.

On the second light-emitting layer, a compound represented by ET-A and Liq was thermally vacuum-deposited to a thickness of 300 Å at a weight ratio of 1: 1 as a second electron transporting layer, and then LiF (Lithium Floride) was thickened to 10 Å and vacuum aluminum was 800Å thick To form a cathode by vapor deposition, an organic light emitting device was manufactured.

Example  2-2 to 2-18

An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using the compounds described in Table 2 instead of the compounds 1 and HT-A in Example 2-1.

Comparative example  2-1 to 2-9

An organic light emitting device was manufactured in the same manner as in Example 2-1, except for using the compounds shown in Table 2 below instead of HT-A and Compound 1 in Example 2-1. In Table 1 below, the parentheses correspond to the weight ratio of each compound, and the lesser compound corresponds to the dopant.

Table 2 shows the results obtained by measuring the voltage and efficiency when a current density of 10 mA / cm ² was applied to the organic light emitting device manufactured in the above Examples and Comparative Examples.

P-type charge generation layer Voltage (V) Efficiency (cd / A) Example 2-1 HT-A: Compound 1 (70:30) 7.88 67.42 Example 2-2 HT-A: Compound 2 (70:30) 7.85 67.53 Example 2-3 HT-A: Compound 3 (70:30) 7.50 69.02 Example 2-4 HT-A: Compound 4 (70:30) 7.62 68.02 Example 2-5 HT-A: Compound 5 (70:30) 7.63 68.16 Example 2-6 HT-A: Compound 6 (70:30) 7.47 69.47 Example 2-7 HT-B: Compound 1 (70:30) 8.02 67.42 Example 2-8 HT-B: Compound 2 (70:30) 8.05 66.01 Example 2-9 HT-B: Compound 3 (70:30) 8.02 65.38 Example 2-10 HT-B: Compound 4 (70:30) 7.99 65.98 Example 2-11 HT-B: Compound 5 (70:30) 8.05 65.23 Example 2-12 HT-B: Compound 6 (70:30) 8.01 65.77 Example 2-13 HT-C: Compound 1 (70:30) 7.78 68.32 Example 2-14 HT-C: Compound 2 (70:30) 7.76 68.63 Example 2-15 HT-C: Compound 3 (70:30) 7.73 69.02 Example 2-16 HT-C: Compound 4 (70:30) 7.73 69.05 Example 2-17 HT-C: Compound 5 (70:30) 7.72 69.09 Example 2-18 HT-C: Compound 6 (70:30) 7.65 70.47 Comparative Example 2-1 HT-A: HAT-CN (70:30) 10.32 52.32 Comparative Example 2-2 HT-B: HAT-CN (70:30) 10.85 51.64 Comparative Example 2-5 HT-B: Compound A (70:30) 9.37 58.57 Comparative Example 2-6 HT-C: Compound A (70:30) 9.19 57.05 Comparative Example 2-7 HT-A: Compound B (70:30) 9.97 56.04 Comparative Example 2-6 HT-C: Compound A (70:30) 9.19 53.05 Comparative Example 2-9 HT-C: Compound B (70:30) 9.01 56.55

Each compound in Table 1 is as follows.

As shown in Table 2, it was confirmed that the compounds represented by Chemical Formulas 1 and 2 of the present invention have a significantly lower voltage and significantly higher efficiency when used as a dopant in the P-type charge generating layer.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: electron transport layer
9: electron injection layer 10: first hole transport layer
11: first light emitting layer 12: first electron transport layer
13: N-type charge generation layer 14: P-type charge generation layer
15: second hole transport layer 16: second light emitting layer
17: second electron transport layer

Claims (14)

cathode; anode; And at least one organic layer provided between the cathode and the anode,
The organic layer includes at least one selected from the group consisting of a hole injection layer and a P-type charge generation layer,
The hole injection layer and the P-type charge generation layer comprises at least one compound selected from the group consisting of compounds represented by the following Chemical Formulas 1 and 2, as an organic light emitting device:
[Formula 1]

[Formula 2]

In Chemical Formulas 1 and 2,
X ₁ and X ₂ are each independently N or CR ', provided that at least one of them is N,
R 'is hydrogen; Or substituted or unsubstituted C _1-60 alkyl,
R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,
A and B are each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl including one or more of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.
According to claim 1,
Formula 1 is any one selected from compounds represented by the following Formulas 1-1 to 1-3, an organic light emitting device:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1 to 1-3,
The description of R ₁ to R ₄ , A and B is as defined in claim 1.
According to claim 1,
The formula 2 is a compound represented by the following formula 2-1 or 2-2, an organic light emitting device:
[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2,
The description of R ₁ to R ₄ , A and B is as defined in claim 1.
According to claim 1,
A and B are cyanoin, an organic light emitting device.
According to claim 1,
R ₂ and R ₃ are cyanoin, an organic light emitting device.
According to claim 1,
R ₁ and R ₄ are each independently any one selected from the group consisting of, an organic light-emitting device.

R ' ₁ to R' ₅ are each independently hydrogen, cyano, fluorine, trifluoromethyl, or trifluoromethoxy,
Y ₁ to Y ₃ are each independently N or CH, provided that at least one of them is N.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following compounds, an organic light emitting device:

According to claim 1,
The compound represented by Formula 2 is any one selected from the group consisting of the following compounds, an organic light emitting device:

According to claim 1,
The organic layer is a light emitting layer; And an electron injection layer, an electron transport layer, an electron injection and electron transport layer, and at least one selected from the group consisting of a hole transport layer, and an organic light emitting device.
delete According to claim 1,
The organic material layer includes two or more light emitting layers,
And an N-type charge generation layer and the P-type charge generation layer between the two or more light-emitting layers.
delete The method of claim 11,
The organic layer further comprises a compound represented by the formula (3), an organic light emitting device:
[Formula 3]

In Chemical Formula 3,
X, Y and Z are each independently substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing one or more of O, N, Si and S.
The method of claim 13,
The compound represented by Formula 3 is any one selected from the group consisting of the following compounds, an organic light emitting device:

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