KR20170134264A - Organic light emitting device - Google Patents

Abstract

The present invention relates to an organic light emitting device having high light emitting efficiency and/or low driving voltage and long lifespan. The organic light emitting device comprises: an anode; a cathode facing the anode; and a light emitting layer provided between the cathode and the anode.

Description

ORGANIC LIGHT EMITTING DEVICE

The present disclosure relates to an organic light emitting device. This specification claims the benefit of Korean Patent Application No. 10-2016-0065774, filed on May 27, 2016, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

International Patent Application Publication No. 2003-012890 Korean Patent Publication No. 2000-0051826

An object of the present invention is to provide an organic light emitting device having a high luminous efficiency and / or a low driving voltage and a long life.

According to one embodiment of the present disclosure, an anode; A cathode opposite to the anode; And an emission layer disposed between the anode and the cathode,

An organic material layer disposed between the cathode and the light emitting layer and including a compound represented by the following Formula 1,

Wherein the light emitting layer comprises a compound represented by the following formula (2).

[Chemical Formula 1]

In Formula 1,

Ar1 to Ar3 are different from each other,

Ar 1 to Ar 3 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heterocyclic group,

(2)

In Formula 2,

Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heteroaryl group,

At least one of Ar4 and Ar5 is an aryl group having 10 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms,

R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 hetero aryl group,

n is an integer of 0 to 8, and R5 when n is 2 or more are the same or different from each other.

The organic light emitting device according to one embodiment of the present application has a low driving voltage and can improve the lifetime characteristics of the device by the thermal stability of the compound. When used in the organic light emitting device described in this specification, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

Since the organic luminescent device of the present invention uses a triazine compound in which three nitrogen (3.0) electronegativity of which is greater than carbon (2.5) in the electron transport layer is substituted in the benzene ring, pyridine, pyrimidine substituted with one or two nitrogen It has higher stability to electrons when it is reduced than compound. Comparing the electron affinity with the DFT, the triazine (-0.16 eV) compound has a molecular neutral (-0.51 eV) and pyridine (-1.00 eV) The difference in energy between anion and anion is small, which is advantageous for injecting electrons into a light emitting layer.

When the anthracene compound is used in the light emitting layer, the organic light emitting device has an excellent effect. When the number of carbon atoms of the substituent bonded to the anthracene is more than 30, the molecular weight increases and the deposition temperature rises. A substituent having a carbon number of 30 or less is preferable, and at least one of the substituents is an aryl group or a heteroaryl group having 10 to 30 carbon atoms, which is excellent in terms of voltage, efficiency, and lifetime.

1 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated FIG.

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

Examples of substituents herein are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; An alkyl group; A cycloalkyl group; Silyl group; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- Pentyl, neopentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2- But are not limited to, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

 In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, naphthyl, anthracene, phenanthrene, pyrenyl, perylenyl,

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

And the like, but the present invention is not limited thereto.

), 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 디벤조카바졸기, 벤조티오펜기, 디벤조티오펜닐기, 벤조퓨란기, 디벤조퓨란기, 벤조나프토퓨란기, 벤조실롤기, 디벤조실롤기, 페난트롤리닐기(phenanthrolinyl group), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기, 페노옥사지닐기, 및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. 이외에도 헤테로고리기의 예로서, 술포닐기를 포함하는 헤테로고리 구조, 예컨대,

,

등이 있다.In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, An acyl group, a hydrocycloalkyl group (e.g.,

), A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyrazinyl group, an isoquinolinyl group , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a dibenzocarbazole group, a benzothiophene group, a dibenzothiophenyl group, a benzofurane group, a dibenzofurane group, A phenothiazolyl group, a thiadiazolyl group, a phenothiazinyl group, a phenoxazinyl group, and condensation structures thereof, and the like, , But are not limited thereto. In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group,

,

.

가 될 수 있다.As used herein, the carbazole fused ring

.

In one embodiment of the present invention, Ar1 to Ar3 each independently represent a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted carbazole fused ring group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinoline group.

In one embodiment of the present specification, the "substituted or unsubstituted" means substituted or unsubstituted with at least one substituent selected from the group consisting of cyano, methyl, phenyl and naphthyl groups.

In one embodiment of the present invention, Ar3 is represented by the following formula (1-1).

[Formula 1-1]

In Formula 1-1,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkylsulfoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted arylsulfoxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C20 alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms or may be bonded to adjacent groups to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, Or an unsubstituted spiro bond.

L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms,

1 is an integer of 1 to 5,

m is an integer of 1 to 3,

n is an integer of 1 to 4,

When l, m and n are each an integer of 2 or more, the structures in parentheses of 2 or more are the same or different from each other.

In one embodiment of the present disclosure, R1 and R2 are hydrogen.

In one embodiment of the present invention, R 3 and R 4 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present invention, R 3 and R 4 are the same or different from each other and are each independently a methyl group or a phenyl group.

In one embodiment of the present invention, R 3 and R 4 are phenyl groups.

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L1 is an arylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L1 is a phenylene group.

In one embodiment of the present invention, Ar5 is an aryl group having 10 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, the Ar 4 substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted carbazole fused ring group; A substituted or unsubstituted benzofluorene group; Or a substituted or unsubstituted benzonaphthofuran group,

Ar5 is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted carbazole fused ring group; A substituted or unsubstituted benzofluorene group; Or a substituted or unsubstituted benzonaphthofuran group.

In one embodiment of the present specification, Ar4 represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted dibenzofurane group, Ar5 is a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted dibenzofurane group.

 In one embodiment of the present specification, Ar4 represents a phenyl group substituted or unsubstituted with a naphthyl group; Naphthyl group; Or a dibenzofurane group, Ar5 is a naphthyl group substituted or unsubstituted with a phenyl group; Or a dibenzofurane group.

In one embodiment of the present specification, the "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of cyano, methyl, phenyl and naphthyl groups

In one embodiment of the present disclosure, R5 is hydrogen.

In one embodiment of the present invention, the substituents of the compound represented by Formula 1 are selected from the following Tables.

In the above table, the dotted line indicates the position of bonding with formula (1).

In one embodiment of the present invention, the substituents of the compound represented by Formula 2 are selected from the following Tables.

In the above table, the dotted line indicates the position of bonding with formula (2).

In one embodiment of the present specification, Ar4 and Ar5 of the compound represented by Formula 2 are selected from the above-mentioned table, and R5 is hydrogen.

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

The organic material layer of the organic light emitting device of the present application may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic light emitting device of the present invention, the organic light emitting device may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In one embodiment of the present invention, the organic material layer containing the compound represented by Formula 1 is an electron transporting layer.

In one embodiment of the present invention, the organic material layer including the compound represented by Formula 1 includes an electron transport layer and an electron injection layer, and the electron transport layer includes a compound represented by Formula 1. [

In one embodiment of the present invention, the light emitting layer further comprises a dopant, and the content ratio of the compound represented by Formula 2 and the dopant is 99: 1 to 90:10.

In one embodiment of the present application, the organic material layer containing the compound represented by Formula 1 is a single layer or an organic material layer of two or more layers.

In one embodiment of the present application, the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and electrons, and a hole blocking layer.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic compound layers, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to one embodiment of the present application is illustrated in Fig.

1 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked Structure is illustrated. In this structure, the compound represented by Formula 1 may include an electron transport layer 7, and the compound represented by Formula 2 may be included in the light emitting layer 3.

The organic luminescent device of the present application can be produced by materials and methods known in the art, except that two or more of the organic layers include the compounds of the formulas (1) and (2) of the present application, respectively.

When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

For example, the organic light emitting element of the present application can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The compounds of Formulas 1 and 2 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

As the anode material, a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth. Specific examples of the anode material that can be used in the present invention 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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

The hole injecting layer is a layer for injecting holes from the electrode. The hole injecting layer has a hole injecting effect for hole injecting effect on the anode, a hole injecting effect for the light emitting layer or the light emitting material due to its ability to transport holes to the hole injecting material, A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

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

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And derivatives thereof, but are not limited thereto.

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

The electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer is a layer which prevents the cathode from reaching the hole, and can be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

The preparation of the organic light emitting device comprising the compounds represented by the above formulas (1) and (2) will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

<Production Example>

[Synthesis of BH-1]

                                                         [BH-1]

Pd (t-Bu ₃ P) ₂ (0.13 g, 62.6 mmol), Naphthalene-2-ylboronic acid (10.8 g, 62.6 mmol) 0.02 mmol) were added to a 2M aqueous K ₂ CO ₃ solution (50 mL) and THF (200 mL), and the mixture was refluxed and stirred for about 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture. The organic layer was dried over magnesium sulfate, distilled under reduced pressure and recrystallized from toluene / EA to obtain BH-1 (12.0 g, 53% 430

[Synthesis of BH-2]

                                                         [BH-2]

BH-2 was synthesized according to the synthesis method of BH-1. (Yield: 55%, MS [M] = 506)

[Synthesis of BH-3]

                                                         [BH-3]

BH-3 was synthesized according to the synthesis method of BH-1. (Yield: 64%, MS [M] = 456)

[Synthesis of BH-4]

                                                         [BH-4]

BH-4 was synthesized according to the synthesis method of BH-1. (Yield: 51%, MS [M] = 546)

[Synthesis of BH-5]

                                                         [BH-5]

BH-5 was synthesized according to the synthesis method of BH-1. (Yield: 60%, MS [M] = 471)

[Synthesis of ET-B]

                                                         [ET-B]

ET-B was synthesized according to the synthesis method of BH-1. (Yield: 51%, MS [M] = 702)

 [Synthesis of ET-C]

                                                         [ET-C]

 ET-C was synthesized according to the synthesis method of BH-1. (Yield: 48%, MS [M] = 599)

[Synthesis of ET-D]

                                                         [ET-D]

 ET-D was synthesized according to the synthesis method of BH-1. (Yield: 50%, MS [M] = 625)

&Lt; Example 1 >

A thin glass substrate coated with ITO (Indium Tin Oxide) at a thickness of 1,400 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following compound HI-A and hexanitrile hexaazatriphenylene (HAT) were sequentially vacuum deposited on the prepared ITO transparent electrode to a thickness of 650 ANGSTROM and 50 ANGSTROM, respectively, to form a hole injection layer.

 Compound HT-A shown below was vacuum-deposited as a hole transporting layer to a thickness of 600 Å, and then HT-B was thermally vacuum-deposited to a thickness of 50 Å as an electron blocking layer. Subsequently, the following host compound BH-1 and 4 wt% of a dopant compound BD as a light emitting layer were vacuum deposited to a thickness of 200 Å. Subsequently, the following compounds ET-B and Liq were thermally vacuum deposited at a ratio of 1: 1 to a thickness of 360 ANGSTROM as an electron transporting layer and an electron injecting layer, followed by vacuum evaporation of Liq to a thickness of 5 ANGSTROM. Magnesium and silver were sequentially deposited on the electron injection layer at a ratio of 10: 1 to a thickness of 220 ANGSTROM and aluminum to a thickness of 1000 ANGSTROM to form a cathode, thereby preparing an organic light emitting device.

&Lt; Example 2 >

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that ET-C was used instead of ET-B.

&Lt; Example 3 >

An organic light emitting device was prepared in the same manner as in Example 1, except that ET-D was used instead of ET-B.

<Example 4>

An organic light emitting device was prepared in the same manner as in Example 1, except that BH-2 was used instead of BH-1.

&Lt; Example 5 >

An organic light emitting device was prepared in the same manner as in Example 4, except that ET-C was used instead of ET-B.

&Lt; Example 6 >

An organic electroluminescent device was prepared in the same manner as in Example 4 except that ET-D was used instead of ET-B.

&Lt; Example 7 >

An organic light emitting device was prepared in the same manner as in Example 1, except that BH-3 was used instead of BH-1.

&Lt; Example 8 >

An organic light emitting device was prepared in the same manner as in Example 7, except that ET-C was used instead of ET-B.

&Lt; Example 9 >

An organic light emitting device was prepared in the same manner as in Example 7, except that ET-D was used instead of ET-B.

&Lt; Example 10 >

An organic light emitting device was prepared in the same manner as in Example 1, except that BH-4 was used instead of BH-1.

&Lt; Example 11 >

Except that ET-C was used in place of ET-B in Example 10, an organic light emitting device was fabricated in the same manner.

&Lt; Example 12 >

An organic light emitting device was fabricated in the same manner as in Example 10 except that ET-D was used instead of ET-B.

&Lt; Example 13 >

An organic light emitting device was prepared in the same manner as in Example 1, except that BH-5 was used instead of BH-1.

&Lt; Example 14 >

An organic light emitting device was prepared in the same manner as in Example 13, except that ET-C was used instead of ET-B.

&Lt; Example 15 >

An organic light emitting device was prepared in the same manner as in Example 13, except that ET-D was used instead of ET-B.

&Lt; Comparative Example 1 &

An organic light emitting device was prepared in the same manner as in Example 1 except that ET-A was used instead of ET-B.

&Lt; Comparative Example 2 &

An organic light emitting device was prepared in the same manner as in Example 4, except that ET-A was used in place of ET-B.

&Lt; Comparative Example 3 &

Except that ET-A was used in place of ET-B in Example 7 above.

&Lt; Comparative Example 4 &

An organic light emitting device was prepared in the same manner as in Example 10 except that ET-A was used instead of ET-B.

&Lt; Comparative Example 5 &

Except that ET-A was used in place of ET-B in Example 13, an organic light emitting device was fabricated in the same manner.

&Lt; Comparative Example 6 >

Except that ET-E was used in place of ET-B in Example 4, an organic light emitting device was fabricated in the same manner.

&Lt; Comparative Example 7 &

An organic light emitting device was prepared in the same manner as in Example 4 except that ET-F was used instead of ET-B.

&Lt; Comparative Example 8 >

An organic electroluminescent device was prepared in the same manner as in Example 4, except that ET-G was used instead of ET-B.

&Lt; Comparative Example 9 &

An organic light emitting device was prepared in the same manner as in Example 1, except that BH-6 was used instead of BH-1.

&Lt; Comparative Example 10 &

An organic light emitting device was prepared in the same manner as in Example 2 except that BH-6 was used instead of BH-1.

&Lt; Comparative Example 11 &

An organic light emitting device was prepared in the same manner as in Example 3, except that BH-6 was used instead of BH-1.

Example Host Electron transport layer @ 10mA / cm ² @ 20mA / cm ² Voltage (V) Efficiency (cd / A) color Life (hr) Example 1 BH-1 ET-B 3.65 6.87 blue 140 Example 2 BH-1 ET-C 3.67 6.89 blue 150 Example 3 BH-1 ET-D 3.63 6.81 blue 160 Example 4 BH-2 ET-B 3.60 6.37 blue 150 Example 5 BH-2 ET-C 3.58 6.49 blue 150 Example 6 BH-2 ET-D 3.50 6.67 blue 155 Example 7 BH-3 ET-B 3.74 6.34 blue 160 Example 8 BH-3 ET-C 3.72 6.45 blue 155 Example 9 BH-3 ET-D 3.69 6.56 blue 150 Example 10 BH-4 ET-B 3.48 6.76 blue 130 Example 11 BH-4 ET-C 3.44 6.83 blue 130 Example 12 BH-4 ET-D 3.42 6.88 blue 135 Example 13 BH-5 ET-B 3.46 6.84 blue 145 Example 14 BH-5 ET-C 3.45 6.85 blue 145 Example 15 BH-5 ET-D 3.42 6.85 blue 150 Comparative Example 1 BH-1 ET-A 4.15 5.89 blue 115 Comparative Example 2 BH-2 ET-A 4.23 5.54 blue 90 Comparative Example 3 BH-3 ET-A 4.30 5.36 blue 85 Comparative Example 4 BH-4 ET-A 3.93 4.88 blue 102 Comparative Example 5 BH-5 ET-A 3.91 4.71 blue 105 Comparative Example 6 BH-2 ET-E 4.10 4.12 blue 70 Comparative Example 7 BH-2 ET-F 3.81 5.94 blue 120 Comparative Example 8 BH-2 ET-G 4.36 3.66 blue 80 Comparative Example 9 BH-6 ET-B 4.40 4.22 blue 80 Comparative Example 10 BH-6 ET-C 4.38 5.52 blue 70 Comparative Example 11 BH-6 ET-D 4.38 5.64 blue 75

As can be seen from the above Table 1, when the compound represented by Formula 1 of the present invention is used as an electron transport layer and the compound represented by Formula 2 is used as a host material in the light emitting layer, excellent effects in terms of voltage, Respectively.

Comparing Examples 4 to 6 and Comparative Examples 6 to 8, when triazine compounds of Formula 1 were used as the electron transporting layer, excellent effects were observed in terms of voltage, efficiency, and lifetime. In Examples 1 to 3 and Comparative Examples 9 to 11, the use of a compound in which at least one of Ar4 and Ar5 of the anthracene compound represented by the formula (2) has 10 or more carbon atoms as a light emitting layer has confirmed excellent effects in terms of voltage, efficiency and life span.

1: substrate
2: anode
3: light emitting layer
4: Cathode
5: Hole injection layer
6: hole transport layer
7: Electron transport layer

Claims (8)

Anode; A cathode opposite to the anode; And an emission layer disposed between the anode and the cathode,
An organic material layer disposed between the cathode and the light emitting layer and including a compound represented by the following Formula 1,
Wherein the light emitting layer comprises a compound represented by the following Formula 2:
[Chemical Formula 1]

In Formula 1,
Ar1 to Ar3 are different from each other,
Ar 1 to Ar 3 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heterocyclic group,
(2)

In Formula 2,
Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heteroaryl group,
At least one of Ar4 and Ar5 is an aryl group having 10 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms,
R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 hetero aryl group,
n is an integer of 0 to 8, and R5 when n is 2 or more are the same or different from each other. The compound according to claim 1, wherein each of Ar1 to Ar3 independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted carbazole fused ring group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted quinoline group. The organic electroluminescent device according to claim 1, wherein Ar 3 is represented by the following formula (1-1):
[Formula 1-1]

In Formula 1-1,
R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkylsulfoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted arylsulfoxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C20 alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms or may be bonded to adjacent groups to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, Or an unsubstituted spiro bond.
L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms,
1 is an integer of 1 to 5,
m is an integer of 1 to 3,
n is an integer of 1 to 4,
When l, m and n are each an integer of 2 or more, the structures in parentheses of 2 or more are the same or different from each other. The compound according to claim 1, wherein the Ar 4 substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted carbazole fused ring group; A substituted or unsubstituted benzofluorene group; Or a substituted or unsubstituted benzonaphthofuran group,
Ar5 is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted carbazole fused ring group; A substituted or unsubstituted benzofluorene group; Or a substituted or unsubstituted benzonaphthofuran group. The organic light-emitting device according to claim 1, wherein R5 is hydrogen. The organic electroluminescent device according to claim 1, wherein the substituent of the compound represented by the formula (1) is selected from the following table:

The organic electroluminescent device according to claim 1, wherein the substituent of the compound represented by the formula (2) is selected from the following table:

The organic light emitting device according to claim 1, wherein the organic material layer is an electron transporting layer.

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