KR20090053488A - Oxadiazole-based compound and organic light emitting device comprising an organic layer comprising the same - Google Patents

Abstract

The present invention relates to an oxadiazole compound represented by Formula 1:

<Formula 1>

In Formula 1, description of Ar ₁ , R ₁ , R _2, and n refers to the detailed description of the invention.

Organic light emitting device

Description

Oxadiazole-based compound and organic light emitting device comprising an organic film comprising the same {Oxadiazole-based compound and organic light emitting device comprising an organic layer comprising the same}

The present invention relates to an organic light emitting device having an oxadiazole compound and an organic film including the same, and more particularly, to an oxadiazole compound including a plate-shaped heterocyclic ring system and an organic film including the same. It relates to an organic light emitting device. The oxadiazole-based compound has excellent electrical characteristics, light emission characteristics, and thermal stability, and when applied to an organic light emitting device, may exhibit low driving voltage, high color purity, and long life characteristics.

Organic light emitting devices (OLEDs) are self-luminous devices that have a wide viewing angle, excellent contrast and fast response time. In addition, the organic light emitting device has a lightweight structure, a simple component, a simple manufacturing process, and a wide viewing angle at high image quality. In addition, high color purity and video can be realized perfectly, and low power consumption and low voltage driving make it suitable for portable electronic devices.

A general organic light emitting device has an anode formed on the substrate, and a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially formed on the anode. Here, the hole transport layer, the light emitting layer and the electron transport layer are organic films made of an organic compound. The driving principle of the organic light emitting device having the structure as described above is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode are moved to the light emitting layer via the hole transport layer. On the other hand, electrons are injected from the cathode into the light emitting layer via the electron transport layer, and carriers are recombined in the light emitting layer to generate excitons. As the excitons are radiated decay, light of a wavelength corresponding to the band gap of the material is emitted.

The light emitting layer forming material of the organic light emitting device may be classified into a fluorescent material using an exciton in a singlet state and a phosphorescent material using a triplet state according to its light emitting mechanism. The fluorescent or phosphorescent material is doped on its own or in a suitable host material to form a light emitting layer, and as a result of electron excitation, singlet excitons and triplet excitons are formed in the host. At this time, the statistical ratio of singlet excitons and triplet excitons is 1: 3.

As a compound constituting the organic film of the organic light emitting device, it is possible to produce an excellent organic film with excellent thermal stability and the like, and to develop a compound capable of improving excellent driving voltage, brightness, efficiency and color purity characteristics when the device is applied.

The present invention provides an oxadiazole compound represented by the following general formula (1):

<Formula 1>

In Chemical Formula 1,

Ar ₁ is a C ₄ -C ₇ alicyclic ring, C ₃ -C ₆ heteroalicyclic ring, C ₅ -C ₈ aromatic ring and C ₃ -C ₇ heteroaromatic ring two or more rings selected from the group consisting of heteroaromatic rings are condensed discotic multi-cyclic ring systems, wherein the heteroaliphatic ring and heteroaromatic ring are N, O, S and P One or more heteroatoms selected from the group consisting of one or more hydrogen of the plate-shaped heterocyclic ring system, independently of one another, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C _1- C ₂₀ alkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, a substituted or unsubstituted C ₇ -C ₂₀ ring Reel alkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkyl alkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, -Si (A ₁ ) (A ₂ ) (A ₃ ), -N (A ₄ ) (A ₅ ), -P (A ₆ ) (A ₇ ), or -SO ₂ (A ₈ ), and A ₁ to A ₈ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group;

R ₁ is a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkenylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkynylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₂₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₂₀ arylene group, substituted or unsubstituted C ₂ -C ₂₀ heteroarylene group , -Si (Z ₁ ) (Z ₂ )-, -N (Z ₃ )-, -P (Z ₄ )-, -O- or -SOO-, wherein Z ₁ , Z ₂ , Z ₃ and Z ₄ Are independently of each other hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group;

R ₂ is a hydrogen atom, a substituted or unsubstituted C ₃ -C ₂₀ aryl group, a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, or a substituted or unsubstituted C ₃ -C ₂₀ oxyaryl group;

n is an integer of 1-4.

In addition, the present invention is a first electrode; Second electrode; And an organic light emitting device comprising an organic film between the first electrode and the second electrode, wherein the organic film includes an oxadiazole compound as described above.

The oxadiazole-based compound has excellent electrical characteristics and thermal stability, and when applied to the organic light emitting device, it may exhibit low driving voltage, high color purity and long life characteristics.

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

An oxadiazole derivative compound according to the present invention is represented by the following general formula (1):

<Formula 1>

In Formula 1, Ar ₁ is a C ₄ -C ₇ alicyclic ring, C ₃ -C ₆ heteroalicyclic ring, C ₅ -C ₈ aromatic ring and C ₃ -C ₇ is a discotic multi-cyclic ring system in which two or more rings selected from the group consisting of heteroaromatic rings are condensed.

In this case, the heteroaliphatic ring and heteroaromatic ring include one or more heteroatoms selected from the group consisting of N, O, S and P.

On the other hand, at least one hydrogen of the plate-shaped heterocyclic ring system, independently of each other, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, substituted or unsubstituted A C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, Optionally substituted with -Si (A ₁ ) (A ₂ ) (A ₃ ), -N (A ₄ ) (A ₅ ), -P (A ₆ ) (A ₇ ), or -SO ₂ (A ₈ ) Can be. In this case, A ₁ to A ₈ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group.

In the present specification, the term "system" in the term "plate-shaped heterocyclic ring system in which two or more rings are condensed" in relation to Ar ₁ is introduced to indicate that two or more rings are in a fused state. Term.

Since Ar ₁ has a plate-like structure, it may provide an excellent pi-electron stacking effect. Therefore, the compound having Formula 1 may have excellent electron transport ability.

Preferably, Ar ₁ may be represented by one of Formulas 2a to 2k, but is not limited thereto.

<Formula 2a> <Formula 2b>

<Formula 2c> <Formula 2d>

<Formula 2e> <Formula 2f>

<Formula 2g> <Formula 2h>

<Formula 2i> <Formula 2j>

<Formula 2k>

In Formulas 1, 2, 3 or 4 of Q ₁ to Q ₁₈ are single bonds, and in Formula 1, are binding sites to R ₁ .

On the other hand, the rest other than a single bond of Q ₁ to Q ₁₈ are independently of each other, a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or Unsubstituted C ₂ -C ₂₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, Substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, -Si (A ₁ ) (A ₂ ) (A ₃ ), -N (A ₄ ) (A ₅ ), -P (A ₆ ) (A ₇ ), or -SO ₂ (A ₈ ) to be. In this case, A ₁ to A ₈ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group.

More preferably, Ar1 is one of the following Chemical Formulas 3a to 3i, but is not limited thereto.

<Formula 3a> <Formula 3b>

<Formula 3c> <Formula 3d>

<Formula 3e> <Formula 3f>

<Formula 3g> <Formula 3h>

<Formula 3i>

In the above formulas, Q ₁ to Q ₆ independently of each other, a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group , -Si (A ₁ ) (A ₂ ) (A ₃ ), —N (A ₄ ) (A ₅ ), —P (A ₆ ) (A ₇ ), or —SO ₂ (A ₈ ). In this case, A ₁ to A ₈ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group.

On the other hand, in the above formula, * indicates a binding site with R ₁ .

In Formula 1, R ₁ may serve as a spacer to modify thermal, electrical properties, and energy levels of an oxadiazole compound having Formula 1.

R ₁ is a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkenylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkynylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₂₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₂₀ arylene group, substituted or unsubstituted C ₂ -C ₂₀ heteroaryl Or a -Si (Z ₁ ) (Z ₂ )-, -N (Z ₃ )-, -P (Z ₄ )-, -O-, or -SOO-. In this case, Z ₁ , Z ₂ , Z ₃ and Z ₄ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group.

Preferably, R ₁ is a C ₁ -C ₁₀ alkylene group, C ₂ -C ₁₀ alkenylene group, C ₂ -C ₁₀ alkynylene group, phenylene group, C ₁ -C ₁₀ alkyl group or C ₆ -C ₁₄ aryl A phenylene group substituted with a group, a naphthylene group, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group substituted a naphthylene group, a pyridinylene group, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ Pyridinylene group substituted with aryl group, pyrimidinylene group, pyrimidinylene group substituted with C ₁ -C ₁₀ alkyl group or C ₆ -C ₁₄ aryl group, imidazolylene group, C _1- C ₁₀ alkyl or C ₆ -C ₁₄ group of imidazolyl substituted with aryl, pyrazolyl group _{(pyrazolylene group), C 1 -C} 10 alkyl or C ₆ -C ₁₄ aryl group a pyrazolyl group, a thiophenyl group substituted with a ( thiophenylene group), C ₁ -C ₁₀ alkyl or C ₆ -C ₁₄ aryl group a substituted thiophenyl group, a fluorenyl group _{(fluorenylene group), C 1 -C} 10 alkyl or C ₆ -C ₁₄ aryl group A substituted fluorenyl _{group, -Si (Z 1) (Z} 2) -, -N (Z 3) -, -P (Z 4) -, a -O- or -SOO-. In this case, Z ₁ , Z ₂ , Z ₃ and Z ₄ are each independently hydrogen, a C ₁ -C ₁₀ alkyl group, or a C ₆ -C ₁₄ aryl group.

,

,

,

,

,

,

,

,

,

,

,

,

,

, -O- 또는

일 수 있으나, 이에 한정되는 것은 아니다.More specifically, R ₁ is -CH _2- , -CH = CH-, -C≡C-,

,

,

,

,

,

,

,

,

,

,

,

,

,

, -O- or

It may be, but is not limited thereto.

In the oxadiazole-based compound represented by Formula 1, the oxadiazole ring is an electron transporting moiety, and the organic layer including the oxadiazole-based compound represented by Formula 1 has a deeper HOMO level. .

In Formula 1, R ₂ may be a substituted or unsubstituted C ₃ -C ₂₀ aryl group, a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group or a substituted or unsubstituted C ₃ -C ₂₀ oxyaryl group.

Preferably, R ₂ is a quinolinylene group, a quinolinylene group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a quinoxalinylene group, a C _1- A quinoxalinylene group substituted with a C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a thiophenyl group, a thiophenyl group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a pyridinyl group ), A pyridinyl group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a pyrimidinylene group, a pyrimidinyl group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, imidazole group _{(imidazolyl group), C 1 -C} 10 alkyl or C ₆ -C ₁₄ aryl group substituted imidazole group, a pyrimidin group sol _{(pyrazolyl group), C 1 -C} 10 alkyl or C ₆ -C ₁₄ aryl group A substituted phenyl group substituted with a pyrazolyl group, an oxyphenyl group, a phenyl group, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a phenyl group substituted with -P (Y ₁ ) (Y ₂ ), -Si ( Or a phenyl group substituted with Y ₃ ) (Y ₄ ) (Y ₅ ) or a phenyl group substituted with —N (Y ₆ ) (Y ₇ ). At this time, the Y ₁ to Y ₇ may be independently of each other, hydrogen, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group.

,

,

,

,

,

,

,

,

,

,

,

,

,

또는

일 수 있으나, 이에 한정되는 것은 아니다.More specifically, R ₂ is

,

,

,

,

,

,

,

,

,

,

,

,

,

or

It may be, but is not limited thereto.

In said Formula (1), n is an integer of 1-4. Preferably, n is one.

According to an embodiment of the present invention, the oxadiazole-based compound may be represented by one of the following Chemical Formulas 1a to 1i, but is not limited thereto.

<Formula 1a> <Formula 1b>

<Formula 1c> <Formula 1d>

<Formula 1e>

<Formula 1f>

<Formula 1g>

<Formula 1h>

<Formula 1i>

Of the above formulas, the description of Q ₁ to Q ₆ and R ₁ refer to the foregoing. On the other hand, X ₁ to X ₆ may be, independently from each other, hydrogen, cyano group, hydroxyl group, nitro group, halogen atom, C ₁ -C ₁₀ alkyl group or C ₆ -C ₁₄ aryl group, but is not limited thereto.

Specific examples of the unsubstituted C ₁ -C ₂₀ alkylene group used in the chemical formula of the present invention include methylene, ethylene, propylene, isobutylene, sec-butylene, pentylene, iso-amylene, hexylene and the like. Wherein at least one hydrogen atom of the alkylene group is a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, C ₁ Optionally substituted with a -C ₂₀ alkyl group, a C ₂ -C ₁₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₆ -C ₂₀ aryl group or a C ₂ -C ₂₀ heteroaryl group. Meanwhile, the substituted or unsubstituted C ₁ -C ₂₀ alkyl group used in the chemical formula of the present invention refers to a monovalent end group having a structure similar to the alkylene group as described above.

The unsubstituted C ₂ -C ₂₀ alkylene group used in the chemical formula of the present invention refers to a group containing one or more carbon-carbon double bonds among the alkylene groups as described above, and specific examples thereof include ethylene, propylene, and the like. have. At least one hydrogen of the alkylene group may be optionally substituted with the same substituent as in the alkylene group. Meanwhile, the substituted or unsubstituted C ₂ -C ₂₀ alkenyl group used in the chemical formula of the present invention refers to a monovalent end group having a structure similar to the alkenyl group described above.

The unsubstituted C2-C20 alkynylene group used in the chemical formula of the present invention refers to a group including one or more carbon-carbon triple bonds among the alkylene groups as described above, and specific examples thereof include acetylene and the like. At least one hydrogen of the alkynylene group may be optionally substituted with the same substituent as in the alkylene group. Meanwhile, the substituted or unsubstituted C ₂ -C ₂₀ alkynylene group used in the chemical formula of the present invention refers to a monovalent end group having a structure similar to the alkynylene group described above.

The unsubstituted C ₁ -C ₂₀ alkoxy group used in the chemical formula of the present invention is a group having a -OB ₁ structure, wherein B ₁ is an alkyl group as described above. Examples thereof include methoxy, ethoxy, phenyloxy, cyclohexyloxy, naphthyloxy, isopropyloxy and the like. At least one hydrogen in the alkoxy group may be optionally substituted with the same substituent as in the alkylene group.

Examples of the unsubstituted C ₃ -C ₂₀ cycloalkylene group used in the chemical formula of the present invention include a cyclohexylene group, a cyclopentylene group, and the like, and at least one hydrogen atom of the cycloalkylene group is the same as the alkylene group described above. It can be substituted with a substituent of. Meanwhile, the substituted or unsubstituted C ₂ -C ₂₀ cycloalkyl group used in the chemical formula of the present invention refers to a monovalent end group having a structure similar to the cycloalkylene group described above.

The unsubstituted C ₁ -C ₂₀ heterocycloalkylene group used in the formula of the present invention has 3 carbon atoms in which one or more carbons constituting the cycloalkylene group exemplified above is replaced with one or more heteroatoms selected from N, O, P or S. It means the divalent organic compound of the 20. At least one hydrogen atom of the heterocycloalkylene group may be substituted with the same substituent as in the alkylene group described above. Meanwhile, the substituted or unsubstituted C ₂ -C ₂₀ heterocycloalkylene group used in the chemical formula of the present invention refers to a monovalent end group having a structure similar to the heterocycloalkylene group described above.

Examples of the unsubstituted C ₆ -C ₂₀ arylene group used in the chemical formula of the present invention include phenylene, naphthylene and the like, wherein one or more hydrogen atoms can be substituted with the same substituents as in the alkylene group described above. Do. On the other hand, C ₆ -C ₂₀ aryl group refers to a monovalent end group having a structure similar to the C ₆ -C ₂₀ arylene group as described above. Meanwhile, the substituted or unsubstituted C ₂ -C ₂₀ aryl group used in the chemical formula of the present invention refers to a monovalent end group having a structure similar to the arylene group as described above.

The unsubstituted C ₂ -C ₂₀ heteroarylene group used in the present invention contains 1, 2 or 3 heteroatoms selected from N, O, P or S, and has 6 to 20 ring atoms having the remaining ring atoms to C. By divalent monocyclic or acyclic aromatic organic compound is meant. At least one hydrogen atom of the heteroarylene group may be substituted with the same substituent as in the alkylene group described above. Meanwhile, the substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group used in the chemical formula of the present invention refers to a monovalent end group having a structure similar to the heteroarylene group described above.

Non-limiting examples of the aryl group include phenyl group, ethylphenyl group, ethylbiphenyl group, o-, m- and p-fluorophenyl group, dichlorophenyl group, dicyanophenyl group, trifluoromethoxyphenyl group, o-, m-, And p-tolyl group, o-, m- and p-cumenyl group, mesityl group, phenoxyphenyl group, (α, α-dimethylbenzene) phenyl group, (N, N'-dimethyl) aminophenyl group, (N, N ' -Diphenyl) aminophenyl group, pentarenyl group, indenyl group, naphthyl group, methylnaphthyl group, anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, fluorenyl group, anthraquinolyl group, Methyl anthryl group, phenanthryl group, triphenylene group, pyrenyl group, chrysenyl group, ethyl- chrysenyl group, pisenyl group, peryllenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group , Hexaphenyl group, hexasenyl group, rubisenyl group, coroneyl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, pyrantrenyl group, obare Group, and the like, but a carbazolyl group, and the like.

Examples of the heteroaryl group include pyrazolyl group, imidazolyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, pyridinyl group, pyridazinyl group, pyrimidinyl group, Triazinyl group, carbazolyl group, indolyl group, etc. are mentioned, but it is not limited to this.

According to an embodiment of the present invention, the oxadiazole-based compound according to the present invention may be Compound 1 below:

<Compound 1>

As described above, the oxadiazole-based compound represented by the general formula (1) has excellent thermal stability and has excellent absorption spectrum, excitation spectrum, and emission spectrum. In addition, it has excellent electrical properties such as LUMO level, HOHO level, energy gap. Therefore, the oxadiazole-based compound having Formula 1 may be usefully used as a material for forming an organic film of an organic light emitting device. In particular, the compound having Formula 1 may be usefully used as a material forming the light emitting layer, the hole blocking layer, the electron transport layer or the electron injection layer of the organic light emitting device.

The oxadiazole-based compound of Formula 1 according to the present invention may be formed in accordance with a generally known method and included in the organic layer of the organic light emitting device. For example, it can form into a film by vapor deposition and a solution process. More specifically, it is possible to form a film by a solution process such as spin coating, dip coating, inkjet printing, etc., in addition to the usual deposition process. In addition, a film containing the oxadiazole compound is formed on the transfer substrate using the deposition process or a solution process, and then a thermal conversion layer is formed to manufacture a transfer film, and then a laser is transferred to the transfer film. By transferring the film containing the oxadiazole-based compound to a region where the organic film including the oxadiazole-based compound is to be formed, various film forming processes may be used, such as performing a film forming process.

The oxadiazole-based compound of Formula 1 as described above may be synthesized by Suzuki coupling such as Scheme 1:

<Scheme 1>

In Scheme 1, Ar ₁ , R ₁ , R _2, and n may be described in detail above.

Ha in the compound B represents a halogen atom.

In order to achieve the second technical problem of the present invention,

A first electrode; Second electrode; And an organic light emitting device including at least an organic film between the first electrode and the second electrode, wherein the organic film may include an oxadiazole compound as described above.

The organic light emitting device according to the present invention can be used for a full color display, lighting, backlight, billboard, optical communication, interior decoration and the like.

The organic layer including the oxadiazole derivative compound of Formula 1 may be a light emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer.

In particular, when the organic layer including the oxadiazole compound of Formula 1 is a light emitting layer, the light emitting layer may include a host and a dopant. In this case, the host or dopant may be the oxadiazole compound of Formula 1.

More specifically, when the organic layer including the oxadiazole compound of Formula 1 is a light emitting layer including a host and a dopant, the oxadiazole compound may serve as a dopant. In this case, the content of the oxadiazole-based compound as a dopant in the light emitting layer may be 3 to 15 parts by weight based on 100 parts by weight of the total weight of the host and the dopant. When the content of the oxadiazole-based compound is less than 3 parts by weight, proper energy transfer may not be performed from the host, and concentration quenching may occur when the content of the oxadiazole-based compound is 15 parts by weight or more. Alternatively, the oxadiazole-based compound may serve as a host. In particular, the oxadiazole-based compound may be used as a host of a light emitting layer including a red phosphorescent dopant or a red fluorescent dopant.

On the other hand, when the organic film containing the oxadiazole-based compound is a hole blocking layer, an electron transporting layer or an electron injection layer, these layers may be composed of only the oxadiazole-based compound, or other well-known hole blocking materials, electron transporting materials or electron injecting materials. It may further include. When the hole base layer, the electron transport layer, or the electron injection layer further includes other well-known hole blocking materials, electron transport materials, or electron injection materials in addition to the oxadiazole-based compound, the oxadiazole-based compound may be a doping agent. Can serve as).

When the oxadiazole compound is used as a dopant of the hole blocking layer, the electron transport layer or the electron injection layer, the content of the oxadiazole compound is 3 to 100 parts by weight based on the total weight of the hole blocking layer, the electron transport layer or the electron injection layer. It may be from 15 parts by weight, but may be differently selected depending on the structure of the organic light emitting device to be manufactured, the thickness of the organic film to be formed, and the like.

In the organic light emitting device according to the present invention, the organic layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer. have.

The structure of the organic light emitting device according to the present invention can be modified in various ways, the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer between the first electrode and the second electrode. It may further comprise one or more layers selected from.

More specifically, an embodiment of the organic light emitting device according to the present invention refers to Figures 1a, 1b and 1c. The organic light emitting device of Figure 1a has a structure consisting of a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / second electrode, the organic light emitting device of Figure 1b is a first electrode / hole injection layer / hole transport layer / It has a structure consisting of a light emitting layer / an electron transport layer / an electron injection layer / a second electrode. In addition, the organic light emitting device of FIG. 1C has a structure of a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode. In this case, at least one of the light emitting layer, the hole blocking layer, the hole injection layer, and the hole transport layer may include an oxadiazole compound according to the present invention.

The light emitting layer of the organic light emitting device according to the present invention may further include a phosphorescent or fluorescent dopant including red, green, blue or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.

Hereinafter, a method of manufacturing an organic light emitting diode according to the present invention will be described with reference to the organic light emitting diode illustrated in FIG. 1C.

First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Herein, a substrate used in a conventional organic light emitting device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, cast, and LB.

When the hole injection layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 mW / sec, and a film thickness are usually appropriately selected in the range of 10 mV to 5 m.

In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. , The heat treatment temperature for removing the solvent after coating is preferably selected in the temperature range of about 80 ℃ to 200 ℃.

As the hole injection layer material, for example, phthalocyanine compounds such as copper phthalocyanine or starburst type amine derivatives TCTA, m-MTDATA, m-MTDAPB, and soluble conductive polymer Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid : Polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3, 4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3, 4- ethylenedioxythiophene) / poly (4-styrene sulfonate)) Known hole injection materials such as Pani / CSA (Polyaniline / Camphor sulfonicacid) or PANI / PSS (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate) Can be used.

Pani / DBSA PEDOT / PSS

The hole injection layer may have a thickness of about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. When the thickness of the hole injection layer is less than 100 kW, the hole injection characteristic may be degraded. When the thickness of the hole injection layer is more than 10000 kW, the driving voltage may increase.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, casting, and LB. In the case of forming the hole transport layer by vacuum deposition and spin coating, the deposition conditions and coating conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

Examples of the material forming the hole transport layer include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [ Aromatic condensed rings such as 1,1-biphenyl] -4,4'-diamine (TPD) and N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD) Known hole transport materials such as conventional amine derivatives having

The hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be degraded, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.

Next, an emission layer (EML) may be formed on the hole transport layer by using a method such as vacuum deposition, spin coating, casting, and LB. When the light emitting layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

As described above, the emission layer may include the oxadiazole derivative compound of Chemical Formula 1 according to the present invention. In this case, the light emitting layer may include a host and a dopant. The oxadiazole compound of Formula 1 according to the present invention may be used as both a host or a dopant. That is, the oxadiazole-based compound of formula 1 may be used with a known fluorescent or phosphorescent dopant material as a host, or the oxadiazole-based compound of formula 1 may be used with a known host as a dopant. At this time, of course, a known host or dopant may be further used.

When the oxadiazole derivative compound according to the present invention is used as a dopant, for example, Alq3 or CBP (4,4'-N, N'-dicarbazole-biphenyl), or PVK (poly ( n-vinylcarbazole)) and the like.

PVK ADN

In case of using the oxadiazole derivative compound according to the present invention as a dopant, other dopant materials which can be mixed and used, or other dopant materials in the case of using the oxadiazole derivative compound according to the present invention as a host, are known As the red dopant, PtOEP, Ir (piq) ₃ , Btp ₂ Ir (acac), DCJTB, or the like may be used, but is not limited thereto.

In addition, as the known green dopant, Ir (ppy) ₃ (ppy = phenylpyridine), Ir (ppy) ₂ (acac), Ir (mpyp) ₃ , C545T, or the like may be used, but is not limited thereto.

On the other hand, as the known blue dopant, F ₂ Irpic, (F ₂ ppy) ₂ Ir (tmd), Ir (dfppz) ₃ , ter-fluorene (fluorene) and the like can be used, but is not limited thereto.

The thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa. This is because, when the thickness of the light emitting layer is less than 100 kW, the light emission characteristics may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.

When used with a phosphorescent dopant in the light emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, holes such as vacuum deposition, spin coating, cast, LB, etc. are formed on the hole transport layer. A blocking layer (HBL) can be formed.

In the case of forming the hole blocking layer by vacuum deposition or spin coating, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer. The hole blocking layer material may be an oxadiazole compound of Chemical Formula 1 according to the present invention as described above. Alternatively, for example, known triazole derivatives or phenanthroline derivatives can be used.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase.

Next, the electron transport layer (ETL) is formed using various methods such as vacuum deposition, spin coating, and casting. When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer.

The electron transport layer material may be an oxadiazole compound of Chemical Formula 1 according to the present invention as described above. Or a known material that functions to stably transport electrons injected from an electron injection electrode (Cathode), and a known material such as quinoline derivatives, especially tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, etc. Can also be used.

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from a cathode, may be stacked on the electron transport layer. The electron injection layer material may be formed of Chemical Formula 1 according to the present invention. Oxadiazole derivative compounds can be used. Alternatively, apart from this, known hole injection materials LiF, NaCl, CsF, Li2O, BaO and the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from the range of conditions almost the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 50 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method. The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned. In addition, a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.

Hereinafter, the synthesis examples and examples of the present invention will be specifically illustrated, but the present invention is not limited to the following synthesis examples and examples.

Synthesis Example  One

Synthesis of Intermediate (a)

Intermediate (a) was synthesized according to the reaction route of Scheme 2:

<Scheme 2>

8.1 mmol (2.14 g) of ester methyl phenylquinolinate and 20 mL of hydrazine monohydrate were reacted in 50 mL of methanol at 50 ° C. for 12 h. The reaction mixture was cooled to room temperature and then treated with 50 mL of water, filtered and washed with water and ether. The product obtained therefrom was recrystallized from water and methanol mixture.

Synthesis of Intermediate (b)

Intermediate (b) was synthesized according to Scheme 3:

<Scheme 3>

4.16 mmol (1.18 g) of 4-bromobenzoic acid, 5 mL of SOCl ₂ and 2 drops of dimethylformamide were heated at 50 ° C. for 2 hours. The reaction mixture was cooled down and SOCl ₂ was evaporated under reduced pressure. The solid obtained from this was treated with hexane and filtered to give a white residue.

Synthesis of Intermediate (c)

Intermediate (c) was synthesized according to Scheme 4 below:

<Scheme 4>

1 mmol (0.249 g) of intermediate (a), 1 mmol (0.219 g) of intermediate (b) and 5 mmol of sodium carbonate (0.53 g) were stirred in 5 mL of dioxane at room temperature for 24 hours. Dioxane was evaporated by treatment with water. The residue was filtered and washed with ether to give intermediate (c).

Synthesis of Intermediate (d)

Intermediate (d) was synthesized according to Scheme 5 below:

Scheme 5

2 mmol (0.892 g) of intermediate (c) was refluxed in 10 mL of phosphorus oxychloride for 12 h. After evaporation of phosphorus oxychloride, a yellow solid was obtained. The yellow solid was purified using chloroform and methanol as silica column and eluent to obtain intermediate (d).

Synthesis of Compound 1

Compound 1 was synthesized according to Scheme 6 below:

<Scheme 6>

A Suzuki coupling reaction between the intermediate (d) and pyrene boronic acid was carried out to obtain Compound 1 as a final product. The structure of Compound 1 was confirmed by mass spectrometry and ¹ H-NMR. FIG. 2 is the ¹ H-NMR spectrum of Compound 1, and FIG. 3 is the Mass spectrum of Compound 1:

¹ H, NMR ( CDCl ₃ ) ppm : 9.27 (d, 1H), 8.91 (s, 1H), 8.57 (d, 2H), 8.48-8.43 (dd, 3H), 8.33 (t, 2H), 8.30-8.26 (m, 3H), 8.24 (s, 1 H), 8.21-8.11 (m, 3H), 8.01-7.95 (m, 3H), 7.88 (t, 1H), 7.68-7.59 (m, 3H).

ESI mass spectra: Exact mass, 550.19, m / z 551.19 (m + H ⁺ )

Evaluation example  1: Characterization of Compound 1

FIG. 4 is a thermogravimetric analysis (TGA) graph of Compound 1 (as measured by heating at 10 ° C. per minute in a nitrogen atmosphere using company TA Instruments, model No. TGA 2050). From Figure 4 it can be seen that the Td value of the compound 1 is about 428 ℃.

FIG. 5 is a differential scanning calorimeter (DSC) graph of Compound 1 (as measured by heating at 10 ° C. per minute in a nitrogen atmosphere using company TA Instruments, model No. DSC 2010). From Figure 5 it can be seen that the Tg value of the compound 1 is about 115 ℃.

FIG. 6 is a graph showing square wave voltametry analysis results of Compound 1. FIG. The square wave voltammetry analysis was performed using Princeton potentiostat (manufactured by AMTEK company, model No. PRSTAT 2273). At this time, a working electrode having platinum (Pt) as a counter electrode and a reference electrode, and having ferrocene and ferrocinium as an internal standard in THF solution Pseudo platinum was used as the working electrode. It can be seen from FIG. 6 that the HOMO level of Compound 1 is 5.70 eV, the LUMO level is 2.82 eV, and the energy gap is 2.88 eV.

Table 1 summarizes simulation values and measured values of the LUMO level and HOMO level values of Compound 1.

H eV L eV gap HOMO LUMO Simulation value 5.451 2.256 3.195

Measures 5.70 2.82 2.88

It can be seen from Table 1 that the LUMO level and HOMO level of Compound 1 are almost similar to the experimental values obtained from FIG. 6.

7 shows an absorption spectrum, an excitation spectrum and an emission spectrum in the solution of Compound 1 above. The absorption spectrum is measured by dissolving Compound 1 in dichloromethane and then using a Shimadzu UV-350 spectrometer. Meanwhile, the excitation spectrum and the emission spectrum were measured using an ISC PC1 spectrofluorometer equipped with a xenon lamp.

According to FIG. 7, the absorption spectrum had peaks at 246 nm, 282 nm, 329 nm and 350 nm, respectively, and the emission spectrum had a maximum emission wavelength of 350 nm.

On the other hand, the color coordinates of Compound 1 in the solution was measured using the same apparatus as described above, it was confirmed that (0.15, 0.05). In addition, the quantum efficiency (QE) of the compound 1 was measured using the same device as described above, and as a result, the quantum efficiency of 50% was confirmed.

1A to 1C are cross-sectional views schematically illustrating structures of one embodiment of an organic light emitting diode according to the present invention, respectively.

2 is an NMR spectrum of a compound according to an embodiment of the present invention,

3 is a mass spectrum of a compound according to an embodiment of the present invention,

4 shows TGA data of a compound according to an embodiment of the present invention,

5 shows DSC data of a compound according to an embodiment of the present invention,

FIG. 6 illustrates square wave volatametry evaluation results of a compound according to an embodiment of the present invention.

7 shows an absorption spectrum, an excitation spectrum and an emission spectrum in a solution of a compound according to an embodiment of the present invention.

Claims (13)

An oxadiazole compound represented by Formula 1 below: <Formula 1>

In Chemical Formula 1, Ar ₁ is a C ₄ -C ₇ alicyclic ring, C ₃ -C ₆ heteroalicyclic ring, C ₅ -C ₈ aromatic ring and C ₃ -C ₇ heteroaromatic ring two or more rings selected from the group consisting of heteroaromatic rings are condensed discotic multi-cyclic ring systems, wherein the heteroaliphatic ring and heteroaromatic ring are N, O, S and P One or more heteroatoms selected from the group consisting of one or more hydrogen of the plate-shaped heterocyclic ring system, independently of one another, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C _1- C ₂₀ alkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, a substituted or unsubstituted C ₇ -C ₂₀ ring Reel alkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alkyl alkoxy group, a substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, -Si (A ₁ ) (A ₂ ) (A ₃ ), -N (A ₄ ) (A ₅ ), -P (A ₆ ) (A ₇ ), or -SO ₂ (A ₈ ), and A ₁ to A ₈ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group; R ₁ is a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkenylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkynylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₂₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₂₀ arylene group, substituted or unsubstituted C ₂ -C ₂₀ heteroarylene group , -Si (Z ₁ ) (Z ₂ )-, -N (Z ₃ )-, -P (Z ₄ )-, -O- or -SOO-, wherein Z ₁ , Z ₂ , Z ₃ and Z ₄ Are independently of each other hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group; R ₂ is a hydrogen atom, a substituted or unsubstituted C ₃ -C ₂₀ aryl group, a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, or a substituted or unsubstituted C ₃ -C ₂₀ oxyaryl group; n is an integer of 1-4. The method of claim 1, An oxadiazole compound, wherein Ar ₁ is represented by one of the following Chemical Formulas 2a to 2k: <Formula 2a> <Formula 2b>

<Formula 2c> <Formula 2d>

<Formula 2e> <Formula 2f>

<Formula 2g> <Formula 2h>

<Formula 2i> <Formula 2j>

<Formula 2k>

Of the above formula, One of Q ₁ to Q _18, 2, 3 or 4 is combined with R ₁ as a single binding site, and the other, rather than a single bond Q ₁ to Q ₁₈ are, independently of one another, a hydrogen atom, a cyano No group, hydroxyl group, nitro group, halogen atom, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkenyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, Substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkyl Alkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, -Si (A ₁ ) (A ₂ ) (A ₃ ), -N (A ₄ ) (A ₅ ), -P (A ₆ ) (A ₇ ), or -SO ₂ (A ₈ ), wherein A ₁ to A ₈ are independently of each other hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group or a substituted or unsubstituted C ₃ -C ₂₀ aryl group. The method of claim 1, An oxadiazole compound, wherein Ar ₁ is one of Formulas 3a to 3i: <Formula 3a> <Formula 3b>

<Formula 3c> <Formula 3d>

<Formula 3e> <Formula 3f>

<Formula 3g> <Formula 3h>

<Formula 3i>

Of the above formula, Q ₁ to Q ₆ independently of each other, a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alke Nyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, -Si (A ₁ ) (A ₂ ) (A ₃ ), -N (A ₄ ) (A ₅ ), -P (A ₆ ) (A ₇ ), or -SO ₂ (A ₈ ), wherein A ₁ to A ₈ are Independently of one another, hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group; * Indicates a binding site with R ₁ . The method of claim 1, R ₁ is a phenyl substituted with a C ₁ -C ₁₀ alkylene group, a C ₂ -C ₁₀ alkenylene group, a C ₂ -C ₁₀ alkynylene group, a phenylene group, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group group, a naphthyl group, a C ₁ -C ₁₀ alkyl or C ₆ -C ₁₄ aryl group substituted with a naphthyl group, a pyridinyl group _{(pyridinylene group), C 1 -C} 10 alkyl or C ₆ -C ₁₄ aryl substituted with A pyrimidinylene group, a pyrimidinylene group, a pyrimidinylene group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, an imidazolylene group, a C ₁ -C ₁₀ alkyl group, or Imidazolylene group substituted with C ₆ -C ₁₄ aryl group, pyrazolylene group, pyrazolylene group substituted with C ₁ -C ₁₀ alkyl group or C ₆ -C ₁₄ aryl group, thiophenylene group, Fluosubstituted with a thiophenylene group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a fluorenylene group, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group Orenylene group, -Si (Z ₁ ) (Z ₂ )-, -N (Z ₃ )-, -P (Z ₄ )-, -O- or -SOO-, and Z ₁ , Z ₂ , Z ₃ And Z ₄ is, independently of each other, hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₁₄ aryl group. The method of claim 1, R ₁ is -CH _2- , -CH = CH-, -C≡C-,

,

,

,

,

,

,

,

,

,

,

,

,

,

, -O- or

An oxadiazole compound, which is characterized by the above-mentioned. The method of claim 1, Wherein R ₂ is a quinolinylene group, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a quinolinyl group, a quinoxalinylene group, a C ₁ -C ₁₀ alkyl group or A quinoxalinylene group substituted with a C ₆ -C ₁₄ aryl group, a thiophenyl group, a thiophenyl group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a pyridinyl group, C ₁ A pyridinyl group substituted with a -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, a pyrimidinylene group, a pyrimidinyl group substituted with a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₁₄ aryl group, an imidazolyl group ( imidazolyl group), C ₁ -C ₁₀ alkyl or C ₆ -C ₁₄ aryl group substituted imidazole group, a pyrimidin group sol _{(pyrazolyl group), C 1 -C} 10 alkyl or C ₆ -C ₁₄ aryl substituted pyrazole Di, oxyphenyl, phenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group or C ₆ -C ₁₄ aryl group, phenyl group substituted with -P (Y ₁ ) (Y ₂ ), -Si (Y ₃ ) (Y ₄ ) (Y ₅₎ Substituted with a substituted phenyl group or a _{-N (Y 6) (Y 7} ) group, Y ₁ to Y ₇ are, independently of each other, hydrogen, C ₁ -C ₁₀ alkyl or C ₆ -C ₁₄ aryl group, characterized in that Oxadiazole type compound. The method of claim 1, R ₂

,

,

,

,

,

,

,

,

,

,

,

,

,

or

An oxadiazole compound, which is characterized by the above-mentioned. The method of claim 1, n is 1, an oxadiazole compound. The method of claim 1, An oxadiazole-based compound represented by any one of the following Chemical Formulas 1a to 1i: <Formula 1a> <Formula 1b>

<Formula 1c> <Formula 1d>

<Formula 1e>

<Formula 1f>

<Formula 1g>

<Formula 1h>

<Formula 1i>

Of the above formula, Q ₁ to Q ₆ independently of each other, a hydrogen atom, a cyano group, a hydroxyl group, a nitro group, a halogen atom, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₂ -C ₂₀ alke Nyl group, substituted or unsubstituted C ₂ -C ₂₀ alkynyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₂₀ aryl group, substituted or unsubstituted C ₇ -C ₂₀ arylalkyl group, substituted or unsubstituted C ₂ -C ₂₀ alkylalkoxy group, substituted or unsubstituted C ₇ -C ₂₀ arylalkoxy group, substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, -Si (A ₁ ) (A ₂ ) (A ₃ ), -N (A ₄ ) (A ₅ ), -P (A ₆ ) (A ₇ ), or -SO ₂ (A ₈ ), wherein A ₁ to A ₈ are Independently of one another, hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group; R ₁ is a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkenylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkynylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₂₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₂₀ arylene group, substituted or unsubstituted C ₂ -C ₂₀ heteroarylene group , -Si (Z ₁ ) (Z ₂ )-, -N (Z ₃ )-, -P (Z ₄ )-, -O- or -SOO-, wherein Z ₁ , Z ₂ , Z ₃ and Z ₄ Are independently of each other hydrogen, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₂₀ aryl group; X ₁ to X ₆ are each independently hydrogen, cyano group, hydroxyl group, nitro group, halogen atom, C ₁ -C ₁₀ alkyl group or C ₆ -C ₁₄ aryl group. The method of claim 1, An oxadiazole compound, which is Compound 1 as follows: <Compound 1>

A first electrode; Second electrode; And an organic film between the first electrode and the second electrode, wherein the organic film comprises an oxadiazole compound according to any one of claims 1 to 10. The method of claim 11, And the organic layer is a light emitting layer, a hole blocking layer, an electron transporting layer, or an electron injection layer. The device of claim 11, wherein the device comprises a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / second electrode, first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / agent. An organic light-emitting device having a structure of two electrodes or a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode.

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