KR20140093163A - Pyrazole-based compound and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a pyrazole-based compound and an organic light emitting device using the same. The compound can be a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, electron injecting material and so on for the organic light emitting device. Especially, the compound can be a material for a light emitting layer. In particular, the compound can be used alone and can be used as a material for a host or a dopant as well.

Description

TECHNICAL FIELD [0001] The present invention relates to a pyrazole-based compound and an organic light emitting device using the pyrazole-based compound.

The present invention relates to a novel pyrazole-based compound and an organic light emitting device comprising the same.

An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high response speed.

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.

The material of the organic thin film may have a light emitting function as required. For example, as the organic thin film material, a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

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.

The present invention provides a novel pyrazole-based compound and an organic light-emitting device comprising the same.

The present invention provides compounds of formula (I)

[Formula 1a]

In Formula 1a,

R ₁ and R ₂ are independently selected from the group consisting of halogen; Amine; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring or an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic ring; or

Any one of R < ₁ > and R < ₂ > is hydrogen; The other of R < ₁ > and R < ₂ > is halogen; Amine; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; Of C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₁ to C ₂₀ an alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C ₆₀ of, C ₆ to C ₆₀ monocyclic or polycyclic aryl group; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring or an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic ring; or

Any one of R < ₁ > and R < ₂ > is a linear or branched C ₁ to C ₆₀ substituted or unsubstituted alkyl; The other of R < ₁ > and R < ₂ > is halogen; Amine; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon rings or aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic rings;

R ₃ to R ₈ are the same or different from each other and independently represent hydrogen; halogen; Amine; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon rings or aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic rings.

Also, the present invention provides an organic light emitting device comprising a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes a compound represented by the following formula :

[Chemical Formula 1b]

In the above formula (1b)

R ₁ to R ₈ are the same or different from each other and independently represent hydrogen; halogen; Amine; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon rings or aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic rings.

The compound described in this specification can be used as an organic layer material of an organic light emitting device. The compound can act as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic light emitting device. In particular, the compound can be used as a light emitting layer material of an organic light emitting device. Specifically, the compound can be used singly as a light emitting material, or as a host material or a dopant material in a light emitting layer.

FIGS. 1 to 3 illustrate a stacking order of electrodes and organic layers of an organic light emitting diode according to embodiments of the present invention.

Hereinafter, the present invention will be described in detail.

The compounds described in this specification can be represented by the above general formula (1a) or (1b). The compound according to the present invention can be used as an organic material layer material of the organic light emitting device according to the structural and physical properties of the core structure.

In the present specification, the halogen includes F, Cl, Br and I.

In the present specification, alkyl includes straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkyl may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.

In the present specification, alkenyl includes straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, alkynyl includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkynyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, alkoxy includes straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkoxy may be 1 to 60, specifically 1 to 40, more particularly 1 to 20.

In the present specification, the cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which cycloalkyl is directly connected to another ring group or condensed. Here, the other ring group may be a cycloalkyl group, but may be other ring groups such as heterocycloalkyl, aryl, heteroaryl, and the like. The carbon number of the cycloalkyl may be 3 to 60, specifically 3 to 40, more particularly 5 to 20.

In the present specification, heterocycloalkyl includes S, O or N as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which heterocycloalkyl is directly connected to another ring group or condensed. Here, the other ring group may be heterocycloalkyl, but may be other ring groups such as cycloalkyl, aryl, heteroaryl, and the like. The heterocycloalkyl may have from 2 to 60 carbon atoms, specifically from 2 to 40, more specifically from 3 to 20 carbon atoms.

In the present specification, aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms and may be further substituted by other substituents. Here, the polycyclic ring means a group in which aryl is directly connected to another ring group or condensed. Here, the other ring group may be aryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, heteroaryl and the like. The carbon number of the aryl may be 6 to 60, specifically 6 to 40, more specifically 6 to 20. Specific examples of aryl include phenyl, biphenyl, triphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl , Indenyl, acenaphthylenyl, and condensed rings thereof, but the present invention is not limited thereto.

As used herein, heteroaryl includes S, O or N as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, which may be further substituted by other substituents. Herein, the term "polycyclic" means a heteroaryl group directly bonded to another ring group or condensed therewith. Here, the other ring group may be heteroaryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, aryl, and the like. The heteroaryl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more particularly 3 to 20 carbon atoms. Specific examples of heteroaryl include pyrrolyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, Thiazolyl, tetrazolyl, pyridinyl, pafiranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, iso A benzothiophene group, a benzofuran group, a diazonaphthyl group, a benzothiophene group, a benzothiophene group, a benzothiophene group, a benzothiophene group, a benzothiophene group, A benzothiophene group, a dibenzofuran group, a carbazolyl group, a phenazinyl group, or a condensed ring thereof, but is not limited thereto.

As used herein, the term " substituted or unsubstituted " refers to halogen, cyano, C ₁ to C ₆₀ linear or branched alkyl, C ₂ to C ₆₀ linear or branched alkenyl, C ₂ to C ₆₀ Straight or branched chain alkynyl, C ₁ to C ₆₀ straight or branched chain haloalkyl, C ₂ to C ₆₀ straight or branched chain haloalkenyl, C ₂ to C ₆₀ linear or branched haloalkyl C ₂ to C ₆₀ straight or branched chain alkoxy, C ₂ to C ₆₀ straight or branched chain alkenyloxy, C ₂ to C ₆₀ straight or branched chain alkynyloxy, C ₃ to C ₆₀ a monocyclic or polycyclic cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic aryl, C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl, C ₂ to the C ₆₀ monocyclic or polycyclic hetero-cycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic aryloxy , A C ₂ to monocyclic or polycyclic heteroaryloxy, C ₆ to monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C ₆₀ of the C ₆₀ of the C ₆₀ (P = O), and substituted or unsubstituted C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted Substituted heteroaryl, and substituted or unsubstituted heteroaryl substituted with one or more substituents. The additional substituents may be further substituted.

According to one embodiment of the present invention, in Formula 1a, any one of R ₁ and R ₂ is hydrogen, and the remaining one of R ₁ and R ₂ is a C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted Cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; Of C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₁ to C ₂₀ an alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C ₆₀ of, C ₆ to C ₆₀ monocyclic or polycyclic aryl group; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI > In formula (1a), when any one of R ₁ and R ₂ is hydrogen and the other one of R ₁ and R ₂ is aryl, the aryl may be substituted with a C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted Aryl; Or a C ₆ to C ₆₀ monocyclic or polycyclic substituted aryl.

The C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl is a condensed ring group or a linking group having two or more substituted or unsubstituted aromatic rings and may be substituted or unsubstituted with further other substituents.

The C ₆ to C ₆₀ monocyclic or polycyclic substituted aryl is C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic C ₆ to C ₆₀ monocyclic or polycyclic aryl which is substituted by substituted or unsubstituted heteroaryl.

According to one embodiment of the present invention, in Formula 1a, any one of R ₁ and R ₂ is a C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, and the remaining of R ₁ and R ₂ One is C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI >

According to an embodiment of the present invention, R ₁ and R ₂ are the same or different from each other and represent hydrogen; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI >

According to one embodiment of the present invention, R ₁ and R ₂ are the same or different and are C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI >

According to one embodiment of the present invention, in Formula 1a, any one of R ₁ and R ₂ is hydrogen, and the remaining one of R ₁ and R ₂ is a C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted Aryl; C ₁ to C ₂₀ an alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C ₆₀ of, C ₆ to C ₆₀ monocyclic or polycyclic aryl group; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl to be. Here, the C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or a C ₆ to C ₆₀ monocyclic or polycyclic substituted aryl is as described above.

According to one embodiment of the present invention, in Formula 1a, any one of R ₁ and R ₂ is a C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, and the remaining of R ₁ and R ₂ One is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl to be.

According to an embodiment of the present invention, R ₁ and R ₂ are the same or different from each other and represent hydrogen; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl to be.

According to one embodiment of the present invention, R ₁ and R ₂ are the same or different and are C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl to be.

According to an embodiment of the present invention, one of R ₁ and R ₂ is hydrogen, and the other of R ₁ and R ₂ is substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, Substituted or unsubstituted thienyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, Substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted benzothiophene group, A substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted amine.

According to one embodiment of the present invention, in Formula 1a, any one of R ₁ and R ₂ is a C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, and the remaining of R ₁ and R ₂ One is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted Substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, A substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, It may be a substituted carbazolyl, or a substituted or unsubstituted amine.

According to one embodiment of the present invention, R ₁ and R ₂ are the same or different and are hydrogen, C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl, substituted or unsubstituted Phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, Substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted A substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl group, It may be, or a substituted or unsubstituted amine

According to one embodiment of the present invention, R ₁ and R ₂ are the same or different and are selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, Unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorene Substituted or unsubstituted benzothiophene group, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted benzothiophene group, An unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted amine.

In the above formula (I) or (Ib), when R ₁ or R ₂ is a substituted or unsubstituted amine, the amine is a C ₁ to C ₂₀ alkyl, a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or Substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl. As one example, the amine may be substituted with straight chain or branched chain alkyl such as methyl, ethyl, propyl, butyl. As another example, the amine may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted anthra Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted thienyl, A substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzothiophene group, Substituted or unsubstituted carbazolyl, or substituted or unsubstituted triazinyl. As a specific example, R ₁ or R ₂ may be selected from the group consisting of N-phenyl-naphthyl-amine, diphenylamine, dinaphthylamine, N-phenyl-fluorenyl- N-naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorenyl-amine, N-naphthyl- Phenyl-diphenyltriazinyl-amine, N-naphthyl-diphenyltriazinyl-amine, or N-biphenyl-diphenyltriamine Lt; / RTI >

In the above embodiments, when R ₁ or R ₂ is further substituted, the substituent is selected from the group consisting of halogen, cyano, C ₁ to C ₆₀ linear or branched alkyl, C ₂ to C ₆₀ linear or branched C ₂ to C ₆₀ linear or branched alkynyl, C ₁ to C ₆₀ straight or branched chain haloalkyl, C ₂ to C ₆₀ straight or branched chain haloalkenyl, C ₂ to C ₆₀ C ₁ to C ₆₀ straight or branched chain alkoxy, C ₂ to C ₆₀ straight or branched chain alkenyloxy, C ₂ to C ₆₀ linear or branched alkoxy, straight or branched chain alkenyloxy, carbonyl-oxy, C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic aryl, a monocyclic of C ₂ to C ₆₀ or polycyclic heterocyclic monocyclic aryl, C ₂ to C ₆₀ or polycyclic heterocycloalkyl, with the proviso that the C ₆ to C ₆₀ Or polycyclic aryloxy, C ₂ to C ₆₀ monocyclic or polycyclic heteroaryloxy, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to monocyclic or polycyclic substituted or unsubstituted of C ₆₀ (P = O), and C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to C ₆₀ monocyclic or multicyclic Substituted or unsubstituted heteroaryl, or substituted or unsubstituted heteroaryl. Specific examples of the further substituent include phenyl, naphthyl, anthracenyl, carbazolyl, alkylamine, arylamine, arylphosphoryl, pyridyl, furanyl, thienyl, C ₁ to C ₂₀ alkyl, Lt; / RTI > and the like.

According to one embodiment of the present invention, in Formula 1a, any one of R ₁ and R ₂ is hydrogen, and the remaining one of R ₁ and R ₂ is biphenyl, triphenyl, naphthyl, anthracenyl, Substituted phenyl with anthracenyl, phenyl substituted with carbazolyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, phenyl and naphthyl Phenyl substituted with amine, phenyl substituted with diphenylphosphoryl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthracenyl substituted with phenyl , Fluorenyl substituted with C ₁ to C ₂₀ alkyl or C ₆ to C ₂₀ aryl, furanyl, thienyl, pyridyl, benzoxazolyl, benzofuran group, benzothiophene group, dibenzofuran group, Dibenzothiophene group, N-substituted indolyl group by phenyl group, carbazolyl, phenyl substituted car N-phenyl-fluorenyl-amine, N-phenyl-fluorenyl-amine, diphenylmethane-substituted phenylcarbamate, Naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorenyl Amine, N-naphthyl-diphenyltriazinyl-amine, or N-naphthyl-anthracenyl-amine, Biphenyl-diphenyltriazinyl-amine. ≪ / RTI >

According to one embodiment of the present invention, one of R ₁ and R ₂ is methyl, ethyl or propyl, and the remaining one of R ₁ and R ₂ is phenyl, biphenyl, triphenyl, naphthyl , Anthracenyl, acenaphthylenyl, phenanthrenyl, pyrenyl, indenyl, naphthyl substituted phenyl, anthracenyl substituted phenyl, carbazolyl substituted phenyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, phenyl And phenyl substituted with a naphthyl substituted amine, phenyl substituted with a diphenylphosphoryl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, Anthracenyl substituted with phenyl, fluorenyl substituted with C ₁ -C ₂₀ alkyl or C ₆ -C ₂₀ aryl, furanyl, thienyl, pyridyl, benzoxazolyl, benzofurane, benzothiophene , A dibenzofuran group, a dibenzothiophene group, an indolyl group which is N-substituted by a phenyl group, N-phenyl-naphthyl-amine, diphenylamine, dinaphthylamine, N-phenyl-fluorenyl-amine, N-naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-naphthyl-dibenzofuranylamine, Naphthyl-anthracenyl-amine, N-naphthyl-anthrylphenyl-amine, N-phenyl-diphenyltriazinyl-amine, N-naphthyl-diphenyltriazinyl -Amine, or N-biphenyl-diphenyltriazinyl-amine.

According to one embodiment of the present invention, R ₁ and R ₂ are the same or different from each other and represent hydrogen, methyl, ethyl, propyl, phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, acetic acid Substituted phenyl with anthracenyl, substituted phenyl with carbazolyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, substituted with phenyl and naphthyl, substituted with phenyl and naphthyl, each of which is substituted with phenyl, naphthyl, phenanthrenyl, pyrenyl, Phenyl substituted with phenyl, substituted phenyl, phenyl substituted with diphenylphosphoryl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, Cyanine, fluorenyl substituted with C ₁ to C ₂₀ alkyl or C ₆ to C ₂₀ aryl, furanyl, thienyl, pyridyl, benzoxazolyl, benzofuran, benzothiophenyl, dibenzofuran , A dibenzothiophene group, an N-substituted indolyl group with a phenyl group, a carbazolyl group, a phenyl group Phenyl-naphthyl-amine, diphenylamine, dinaphthylamine, N-phenyl-fluorenyl-amine, N-naphthyl- N-naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorene Amine, N-phenyl-diphenyltriazinyl-amine, N-naphthyl-diphenyltriazinyl-amine, or N -Biphenyl-diphenyltriazinyl-amine. ≪ / RTI >

According to one embodiment of the present invention, R ₁ and R ₂ are the same or different from each other in the above general formulas (1a) and (1b), and represent phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, acenaphthylenyl, phenanthrenyl Phenyl substituted with phenyl substituted with diphenylamine, phenyl substituted with phenyl and naphthyl, phenyl substituted with naphthyl, phenyl substituted with naphthyl, phenyl substituted with naphthyl, phenyl substituted with phenyl substituted with naphthyl, Phenyl substituted with phenyl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthracenyl substituted with phenyl, C ₁ -C ₂₀ alkyl or C ₆ ~ C a fluorenyl, furanyl, thienyl, pyridyl, benzoxazolyl, benzofuran group substituted with a ₂₀ aryl, benzothiophene group, a dibenzofuran group, a dibenzothiophene group, N-substituted indolyl by phenyl group, carbazolyl, phenyl substituted carbazolyl, triazinyl Naphthyl-fluorenyl-amine, N-phenyl-naphthyl-amine, diphenylamine, dinaphthylamine, N-phenyl- N-naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorenyl-amine, N -Naphthyl-diphenyltriazinyl-amine, or N-biphenyl-di (tert-butoxycarbonyl) amine, Phenyltriazinyl-amine. ≪ / RTI >

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₃ is C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic Unsubstituted heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl .

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₃ is a C ₃ to C ₁₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, a C ₆ to C ₁₄ monocyclic or polycyclic Unsubstituted aryl, and C ₃ to C ₆ monocyclic or polycyclic substituted or unsubstituted heteroaryl.

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₃ represents a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted thienyl , Substituted or unsubstituted furanyl, and substituted or unsubstituted cyclopropyl.

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₃ may be selected from the group consisting of phenyl, naphthyl, pyridyl, thienyl, furanyl and cyclopropyl.

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₆ And R ₇ are the same or different from each other and independently selected from the group consisting of hydrogen, halogen, C ₁ to C ₆₀ straight or branched chain substituted or unsubstituted alkoxy, C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl , A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl, a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted (P = O) substituted with a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl, And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl .

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₆ And R ₇ are the same or different and are independently selected from the group consisting of hydrogen, halogen, C ₁ to C ₆ straight or branched chain substituted or unsubstituted alkoxy, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl, and an amine substituted with C ₁ to C ₂₀ alkyl or C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl .

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₆ And R ₇ are the same or different and are independently selected from the group consisting of hydrogen, F, substituted or unsubstituted methoxy, substituted or unsubstituted phenyl, substituted or unsubstituted diphenylamine, substituted or unsubstituted dimethylamine, Lt; / RTI > unsubstituted furanyl and unsubstituted furanyl.

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₆ is hydrogen and R ₇ is selected from the group consisting of F, methoxy, phenyl, diphenylamine, dimethylamine and furanyl.

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₇ is hydrogen and R ₆ is selected from the group consisting of F, methoxy, phenyl, diphenylamine, dimethylamine and furanyl.

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₆ And R ₇ are the same or different and are independently selected from the group consisting of F, methoxy, phenyl, diphenylamine, dimethylamine, and furanyl.

According to one embodiment of the present invention, in the above general formulas (1a) and (1b), R ₆ And R < ₇ > is hydrogen.

According to one embodiment of the present invention, R ₄ , R ₅ and R ₈ in the above general formulas (1a) and (1b) are hydrogen.

Specific examples of the compound of formula (I) or (Ib) are shown by the following structural formulas, but are not limited thereto.

The above-mentioned compounds can be produced on the basis of the preparation examples described later.

For example, the compound of formula (Ia) or (Ib) may be prepared according to the following scheme 1 or 2. If necessary, substituents may be added or removed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

[Reaction Scheme 1]

[Reaction Scheme 2]

Another embodiment of the present invention provides an organic light emitting device comprising the compound of formula (Ib). Specifically, the organic light emitting device according to the present invention includes a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, and at least one of the organic layers includes a compound represented by the formula (1b).

FIGS. 1 to 3 illustrate the stacking process of the electrodes and organic layers of the organic light emitting diode according to the embodiments of the present invention. However, the scope of the present invention is not intended to be limited by these drawings, and the structure of the organic light emitting device known in the art can be applied to the present invention.

1, an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, the present invention is not limited to such a structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG.

FIG. 3 illustrates the case where the organic material layer is a multilayer. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present invention is not limited by such a laminated structure, and other layers other than the light emitting layer may be omitted as necessary, and other necessary functional layers may be added.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer contains the compound of Formula 1b.

The compound of formula (1b) may constitute at least one layer of the organic material layer of the organic light emitting device. However, if necessary, the organic material layer may be formed by mixing with other materials.

The compound of Formula 1b can be used as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material in an organic light emitting device. In particular, the compound of Formula 1b may be used as a material of a light emitting layer of an organic light emitting device. Specifically, the compound of Formula 1b can be used as a light emitting material of the light emitting layer. Further, the compound of Formula 1b may be used as a host material or a dopant material of the light emitting layer. The compounds of formula (Ib) may be used alone or in combination of two or more. The compound of formula (Ib) may also be used in combination with other kinds of compounds.

In the organic light emitting device according to the present invention, materials other than the compound of Formula 1b are illustrated below, but these are for illustrative purposes only, and are not intended to limit the scope of the present invention. Materials known in the art Can be replaced.

As the cathode material, materials having a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used.

As the cathode material, materials having relatively low work functions can be used, and metals, metal oxides, conductive polymers, and the like can be used.

As the hole injecting material, a known hole injecting material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a compound described in Advanced Material, 6, p. 677 (1994) PANDOT / PSS (Polyaniline / Dodecylbenzenesulfonic acid), which is a soluble conductive polymer such as TCA, m-MTDATA, m-MTDAPB, 4-ethylenedioxythiophene / poly (4-styrenesulfonate) / poly (4-styrene sulfonate) / Pani / CSA (polyaniline / camphor sulfonic acid) PANI / PSS (polyaniline / poly (4-styrene-sulfonate): polyaniline / poly (4-styrenesulfonate)).

As the hole transporting material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or a high molecular weight material may be used.

Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, Derivatives thereof, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used as well as low molecular weight materials and high molecular weight materials.

As the electron injecting material, for example, LiF is typically used in the art, but the present invention is not limited thereto.

As the light emitting material, red, green or blue light emitting materials may be used, and if necessary, two or more light emitting materials may be mixed and used. Further, a fluorescent material may be used as a light emitting material, but it may be used as a phosphorescent material. As the light emitting material, a material which emits light by coupling holes and electrons respectively injected from the anode and the cathode may be used. However, materials in which both the host material and the dopant material participate in light emission may also be used.

When the compound according to the present invention is used as a phosphorescent host material, phosphorescent dopant materials used together can be those known in the art.

For example, phosphorescent dopant materials represented by LL'MX, LL'L "M, LMXX ', L ₂ MX and L ₃ M can be used, but the scope of the present invention is not limited by these examples.

Here, L, L ', L ", X and X' are two different left ligands and M is a metal forming an octahedral complex.

M may be iridium, platinum, osmium, and the like.

L is sp ² An anionic bidentate ligand that is coordinated to M by carbon and hetero atoms, and X can function to trap electrons or holes. Non-limiting examples of L include 2- (1-naphthyl) benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole) -Benzoquinoline), (thienylpyridine), phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine and the like. Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the present invention is not intended to limit the scope of the present invention.

[Preparation Example 1] Preparation of Compound 1

compound 1-1 Manufacturing

Compound 2-bromo aldehyde _{10g (54㏖, Pd (PPh 3} ) 2 Cl 2 0.8g (1.1m㏖), CuI 0.4g (2.2m㏖) and triethyl amine was added at room temperature after 10 min. Stirring for 300㎖ After the completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , And the residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 9.1 g (82%) of the desired compound 1-1 .

compound One Manufacturing

9 g (44 mmol) of Compound 1-1 was dissolved in ethanol, 8.2 g (44 mmol) of TsNHNH ₂ was added, and the mixture was stirred at room temperature for 20 minutes. 1.1 g (4.4 mmol) of AgOTf was added thereto, followed by stirring at 70 DEG C for 30 minutes. After the temperature was cooled to room temperature, 17.3 g (88 mmol) of benzyl phenyl ketone and 28 g (132 mmol) of K ₃ PO ₄ were added thereto, followed by stirring at 70 ° C for 17 hours or longer. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 12.7 g (73%) of the desired compound 1 .

[Preparation Example 2] Preparation of Compound 60

2 g (9.7 mmol) of Compound 1-1 was dissolved in ethanol, 1.8 g (9.7 mmol) of TsNHNH ₂ was added, and the mixture was stirred at room temperature for 20 minutes. AgOf (0.25 g, 0.97 mmol) was added thereto, followed by stirring at 70 ° C for 30 minutes. After cooling to room temperature where the 2-phenyl-1- (thiophen-2-yl) ethanone (2-phenyl-1- (thiophen -2-yl) ethanone) 3.8g (18.8m㏖), K 3 6.2 g (29.1 mmol) of PO ₄ was added thereto, followed by stirring at 70 ° C for 17 hours or more. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 2.4 g (62%) of the target compound 60 .

[Preparation Example 3] Preparation of Compound 76

compound 1-2 Manufacturing

Compound 2-bromo aldehyde 10g (54㏖), Pd (PPh 3) 2 Cl 2 0.8g (1.1m㏖), CuI 0.4g (2.2m㏖) and triethyl amine was added at room temperature after 10 300㎖ bun dongan Lt; / RTI > 9.1 g (59.4 mmol) of 2-naphthylacetylene was added thereto, followed by stirring at 50 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 10.4 g (75%) of the target compound 1-2 .

compound 76 Manufacturing

After dissolving 5 g (19.5 mmol) of Compound 1-2 in ethanol, 3.6 g (19.5 mmol) of TsNHNH ₂ was added, followed by stirring at room temperature for 20 minutes. 0.5 g (1.95 mmol) of AgOTf was added thereto, followed by stirring at 70 DEG C for 30 minutes. After the temperature was cooled to room temperature, 7.65 g (39 mmol) of benzyl phenyl ketone and 12.4 g (58.5 mmol) of K ₃ PO ₄ were added thereto, followed by stirring at 70 ° C for 17 hours or longer. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 6.1 g (70%) of the desired compound 76 .

[Preparation Example 4] Preparation of Compound ( 93 )

compound 1-3 Manufacturing

After adding 5 g (27 mol) of _2- bromoaldehyde, 0.4 g (0.55 mmol) of Pd (PPh ₃ ) ₂ Cl ₂ , 0.2 g (1.1 mmol) of CuI and 150 ml of triethylamine, It was stirred. 3.1 g (29.7 mmol) of 2-pyridyl acetylene was added thereto, followed by stirring at 60 占 폚 for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 4.8 g (85%) of the desired compound 1-3 .

compound 93 Manufacturing

After dissolving ₄ g (19.5 mmol) of Compound 1-3 in ethanol, 3.6 g (19.5 mmol) of TsNHNH ₂ was added, followed by stirring at room temperature for 20 minutes. 0.5 g (1.95 mmol) of AgOTf was added thereto, followed by stirring at 70 DEG C for 30 minutes. After the temperature cooled down to room temperature here 1- (naphthalen-2-yl) heptanone (1- (naphthalen-2-yl ) -2-phenylethanone) 9.6g (39m㏖) -2-phenyl, K ₃ PO ₄ 12.4 g (58.5 mmol) was added thereto, followed by stirring at 70 DEG C for 17 hours or longer. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 5.2 g (60%) of the desired compound 93 .

[Preparation Example 5] Preparation of Compound 155

compound 1-4 Manufacturing

After adding 5 g (27 mol) of _2- bromoaldehyde, 0.4 g (0.55 mmol) of Pd (PPh ₃ ) ₂ Cl ₂ , 0.2 g (1.1 mmol) of CuI and 150 ml of triethylamine, Lt; / RTI > 3.2 g (29.7 mmol) of (2-thienyl) acetylene (2-thienyl) acetylene was added thereto, followed by stirring at 60 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.6 g (81%) of the desired compound 1-4 .

compound 155 Manufacturing

2 g (9.4 mmol) of Compound 1-4 was dissolved in ethanol, 1.8 g (9.4 mmol) of TsNHNH ₂ was added, and the mixture was stirred at room temperature for 20 minutes. 0.24 g (0.94 mmol) of AgOTf was added thereto, followed by stirring at 70 DEG C for 30 minutes. After the temperature was cooled to room temperature, 1 - ([1,1'-biphenyl] -3-yl) -2-phenylethanone (1 - (18.8 mmol) of K ₂ PO _{4, and} 6.0 g (28.2 mmol) of K ₃ PO ₄ were added thereto, followed by stirring at 70 ° C. for 17 hours or longer. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 2.9 g (65%) of the desired compound 155 .

[Preparation Example 6] Preparation of Compound 241

compound 1-5 Manufacturing

Compound 2-bromo-5-fluoro-benzaldehyde 10g (49.2m㏖), Pd (PPh 3) 2 Cl 2 0.69g (0.99m㏖), CuI 0.38g (1.97m㏖) and triethyl amine was added to 300㎖ The mixture was stirred at room temperature for 10 minutes. 5.1 g (49.2 mmol) of phenylacetylene was added thereto, followed by stirring at 60 占 폚 for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was purified by column chromatography using dichloromethane and hexane as eluent to obtain 8.6 g (78%) of the desired compound 1-5 .

compound 241 Manufacturing

After 10 g (44.6 mmol) of Compound 1-5 was dissolved in ethanol, 8.3 g (44.6 mmol) of TsNHNH ₂ was added, and the mixture was stirred at room temperature for 20 minutes. 1.15 g (4.46 mmol) of AgOTf was added thereto, followed by stirring at 70 DEG C for 30 minutes. After the temperature was cooled to room temperature, 17.5 g (89.2 mmol) of benzyl phenyl ketone and 28.4 g (133.8 mmol) of K ₃ PO ₄ were added thereto, followed by stirring at 70 ° C for 17 hours or longer. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 12.6 g (68%) of the desired compound 241 .

[Preparation Example 7] Preparation of Compound 244

compound 244 Manufacturing

8g (35.7 mmol) of Compound 1-5 was dissolved in ethanol, 6.65 g (35.7 mmol) of TsNHNH ₂ was added, and the mixture was stirred at room temperature for 20 minutes. 0.92 g (3.6 mmol) of AgOTf was added thereto, followed by stirring at 70 캜 for 30 minutes. After cooling to room temperature, 14 g (71.4 mmol) of benzyl phenyl ketone and 22.7 g (107.1 mmol) of K ₃ PO ₄ were added thereto, followed by stirring at 70 ° C for 17 hours or longer. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. Purification by column chromatography using dichloromethane and hexane as eluent gave 9.3 g (56%) of the desired compound 244 .

[Preparation Example 8] Preparation of Compound 301

compound 301 Manufacturing

10 g (24.1 mmol) of the compound 241 was dissolved in DMF, and 3.8 g (96.4 mmol) of NaH (60% in oil) was slowly added thereto, followed by stirring at room temperature for 30 minutes. 8.1 g (48.2 mmol) of carbazole was slowly added thereto, followed by stirring at 100 ° C for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as eluent, and then recrystallized with ethanol to obtain 9.2 g (68%) of the target compound 301 .

[Preparation Example 9] Preparation of Compound 271

compound 1-6 Manufacturing

Compound 2-bromo-4,5-dimethoxy benzaldehyde 10g (40.8m㏖), Pd (PPh 3) 2 Cl 2 0.58g (0.82m㏖), CuI 0.58g (1.63m㏖) and triethylamine 300㎖ And the mixture was stirred at room temperature for 10 minutes. 4.2 g (40.8 mmol) of phenylacetylene was added thereto, followed by stirring at 60 ° C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 8.8 g (81%) of the desired compound 1-6 .

compound 271 Manufacturing

5 g (18.8 mmol) of Compound 1-6 was dissolved in ethanol, 3.5 g (18.8 mmol) of TsNHNH ₂ was added, and the mixture was stirred at room temperature for 20 minutes. 0.5 g (1.9 mmol) of AgOTf was added thereto, followed by stirring at 70 DEG C for 30 minutes. After the temperature was cooled to room temperature, 7.4 g (37.6 mmol) of benzyl phenyl ketone and 11.9 g (56.4 mmol) of K ₃ PO ₄ were added thereto, followed by stirring at 70 ° C for 17 hours or longer. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 5.4 g (63%) of the desired compound 271 .

[Preparation Example 10] Preparation of Compound 316

compound 1-7 Manufacturing

10 g (21.9 mmol) of Compound 271 was dissolved in 200 ml of dichloromethane and then cooled to 0 占 폚. To this was added 66 mL (66 mmol) of boron tribromide slowly. The temperature was warmed to room temperature and then stirred. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.3 g (46%) of the desired compound 1-7 .

compound 1-8 Manufacturing

4 g (9.3 mmol) of the compound 1-7 was dissolved in dichloromethane, and 4 g (37.3 mmol) of 2,6-lutidine was added thereto. The mixture was cooled to -30 ° C and stirred. To this was slowly added 3.4 ml (20.5 mmol) of trifluoromethanesulfonic anhydride. The temperature was raised to 0 < 0 > C and stirred for one hour. When the reaction was complete, it was extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 4.4 g (69%) of the desired compound 1-8 .

compound 316 Manufacturing

Compound 1-8 4g (5.8m㏖), phenylboronic acid 7g (7m㏖), Pd (PPh 3) 4 4.5g (0.3m㏖), and K ₂ CO _3, to 1.6g (11.6m㏖) toluene / Dissolved in 80 ml / 16 ml / 16 ml of ethanol / distilled water, and then stirred at 100 ° C. After the reaction was completed, the reaction mixture was extracted with distilled water and EA. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using dichloromethane and hexane as eluent to obtain 2.3 g (73%) of the desired compound 316 .

Compounds were prepared in the same manner as in Production Examples 1 to 10, and the results of confirmation of the synthesis thereof are shown in Table 1.

compound _{^{1 H NMR (CDCl 3, 200Mz}} ) MS / FAB found calculated One [delta] = 7.41-7.66 (17H, m), 7.79 (2H, d), 7.92 396.48 396.16 2 (2H, m), 8.55 (1H, d), 8.04-8.08 (2H, m) 446.54 446.18 5 [delta] = 7.39-7.63 (18H, m), 7.91-7.92 (4H, m), 8.27 496.60 496.19 9 (1H, s), 7.21-7.33 (4H, m), 7.41-7.66 (13H, m), 7.92 434.53 434.18 15 (2H, d), 8.42 (1H, d), 8.55 (2H, d), 7.41-7.66 (17H, m), 7.92 3H, d) 522.64 522.21 16 (2H, d), 8.42 (1H, d), 8.55 (2H, d), 7.41-7.66 (16H, m), 7.92 1H, d) 522.64 522.21 18 (1H, d), 8.12 (1H, d), 8.89-8.93 (2H, m) 496.60 496.19 22 [delta] = 1.72 (6H, s), 7.28-7.66 (19H, m), 7.87-7.92 (2H, 512.64 512.23 23 ? = 7.32-7.72 (19H, m), 7.81 (1H, m), 7.89-7.92 (2H, m) 496.60 496.19 25 (2H, m), 8.55 (1H, d), 7.31 (1H, t), 7.41-7.87 561.67 : 561.22 26 [delta] = 1.85 (6H, s), 7.17-7.39 (9H, m), 7.71-7.75 (3H, m 7.91-7.93 561.67 561.22 30 (2H, m), 8.28 (4H, m), 8.55 (1 H, m), 7.87 1H, d) 716.83 716.27 31 ? = 7.39-7.63 (23H, m), 7.91-7.92 (5H, m) 572.70 572.23 33 (2H, d), 8.39 (2H, d), 8.93 (2H, d) 596.72 596.23 45 (1H, m), 7.87 (1H, d), 7.92-7.93 (2H, m) 512.64 512.23 50 (2H, d), 8.34 (1 H, s), 7.31-7.87 (24H, m) 686.84 686.27 53 (3H, m), 7.91-8.00 (5H, m), 7.58-7.59 (3H, m) 541.68 541.25 54 (1H, d), 8.59 (2H, d), 7.90 (1H, 398.46 398.15 58 (2H, d), 7.92 (1H, d), 7.83 (2H, 596.66 596.20 60 [delta] = 7.17 (1H, t), 7.41-7.69 (16H, m), 7.92 402.51 402.12 63 [delta] = 7.41-7.66 (24H, m), 7.79 (2H, d), 7.92 548.67 548.23 68 (2H, d), 7.41-7.66 (15H, m), 7.79-7.92 (5H, m) 528.60 528.18 69 [delta] = 7.41-7.66 (27H, m), 7.92 (1H, d) 548.67 548.23 73 (2H, d), 7.92 (2H, d), 7.92 (1H, d) 478.61 478.15 75 d), 7.99 (2H, d), 8.75 (2H, d), 7.79 (2H, 473.57 473.19 81 (1H, d), 8.85 (1H, d), 8.48 (1H, 570.68 570.21 85 (3H, m), 7.91-8.00 (5H, m), 7.58-7.59 (3H, m) 486.56 486.17 93 (1H, s), 8.62 (1H, s), 9.30 (1H, s), 7.41 (1H, m), 7.87 1H, d) 447.53 447.17 104 ? = 1.85 (6H, s), 7.17-7.39 (7H, m), 7.71-7.99 (9H, m) 473.57 473.19 107 (2H, m), 7.30 (2H, m), 7.30-7.92 (2H, m) 8.53 (1H, d), 8.62 (1H, s), 9.30 (1H, d) 573.68 573.22 111 m), 8.04-8.08 (2H, m), 8.42 (1H, d), 8.53-8.62 (3H, m), 7.41-7.70 (14H, m), 7.85-7.92 ), 9.30 (1 H, d) 523.63 523.20 115 (1H, m), 8.04-8.08 (2H, m), 8.42 (1H, d), 8.53-8.62 (3H, m) ), 9.30 (1 H, d) 562.66 562.22 126 (2H, m), 8.04-8.08 (2H, m), 8.42 (1H, m), 8.53-8.62 8.62 (1 H, s), 9.30 (1 H, d) 599.72 599.24 128 (1H, m), 8.04-8.08 (2H, m), 8.04-8.08 (2H, m) 8.42-8.62 (3H, m), 9.30 (1H, d) 562.66 562.22 135 (7H, m), 7.63-7.79 (6H, m), 7.87-7. 93 (3H, m), 7.38-7.55 8.53-8.62 (2H, m), 9.30 (1H, d) 513.63 513.22 141 s), 8.45 (1H, s), 8.45-8.53 (2H, m), 8.62 (1H, s) 9.30 (1 H, d) 553.67 553.16 145 m), 7.92 (1H, m), 8.53 (1H, d, J = 1H, d), 8.62 (1H, s), 9.30 (1H, d) 440.54 440.20 149 (1H, d), 8.62 (1H, s), 9.30 (1H, d), 7.84 1H, d) 387.43 387.14 156 (2H, m), 8.22 (1H, d), 8.42 (1H, d), 7.41-7.69 (15H, m), 7.85-7.92 ), 8.55 (1 H, d) 528.66 528.17 160 (1H, d), 8.55 (1H, d), 7.87-7.94 (3H, m) 567.70 567.18 165 m), 8.52 (1H, d), 8.47-7.52 (16H, m), 7,63-7.77 (5H, m), 7.87-7.94 722.86 722.23 171 (2H, m), 8.22 (1H, d), 8.42 (1H, d), 8.55 (1H, 1H, d) 604.76 604.20 175 (3H, m), 7.42-7.73 (12H, m), 7.92-8.08 (6H, m), 8.22-8.30 ) 578.72 578.18 186 (2H, m), 8.04 (2H, m), 8.02 (2H, m), 7.24-7.61 8.42 (1 H, d), 8.55 (1 H, d) 486.61 486.21 201 (2H, m), 2.22 (1H, m), 7.29 (1H, s), 7.38-7.60 (16H, m), 7.70-7.75 (3H, m), 7.93 1H, d), 8.04-8.08 (2H, m), 8.42 (1H, d), 8.55 562.70 562.24 216 (7H, m), 7.93 (9H, m), 8.34-8.45 (2H, m) (2H, m) 516.65 516.17 255 (2H, m), 8.42 (1H, m), 8.42 (1H, m), 8.04 8.55 (1H, m) 540.63 540.20 271 (1H, s), 7.41-7.59 (14H, m), 7.78-7.79 (2H, m) 456.53 456.18 302 d), 8.12 (1H, d), 8.55 (1H, d), 7.94 (1H, 561.67 561.22 316 (1H, s), 8.15 (1H, s), 7.79 (1H, s) 548.67 548.23

Experimental Example: OLED  Device fabrication

[Comparative Example]

The transparent electrode ITO thin film obtained from the glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol and used.

Next, an ITO substrate was placed on a substrate folder of a vacuum deposition equipment, and a cell in a vacuum deposition equipment was charged with 2-TNATA (4,4 ', 4 "-tris (N, N- (2- naphthyl) -phenylamino) amine).

Subsequently, the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate. NPB (N, N'-bis (? -Naphthyl) -N, N'-diphenyl-4,4'-diamine) was placed in another cell in a vacuum deposition apparatus, Lt; RTI ID = 0.0 > 300 A < / RTI >

After the hole injecting layer and the hole transporting layer were formed as described above, a phosphorescent green light emitting material having the following structure was deposited on the light emitting layer. (4,4'-bis (carbazol-9-yl) biphenyl) as a green luminescent host material was vacuum deposited on a cell in a vacuum deposition apparatus to a thickness of 350 Å and a green light emitting dopant Ir (ppy) ₃ (Tris (2-phenylpyridine) iridium (III)) was vacuum deposited at 10% on the host material.

Then, to the deposition of the BCP (2,9-dimethyl-4,7- diphenyl-1,10-phenanthroline) Major blocking layer material such as to the major-stop layer to 50 Å thick, and as the electron transporting layer Alq ₃ ( Tris (8-hydroxy-quinolinato) aluminum was deposited to a thickness of 200 Å.

Thereafter, lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer. Then, an Al cathode was deposited to a thickness of 1000 Å to fabricate an OLED.

On the other hand, all the organic compounds required for OLED device fabrication were vacuum sublimated and refined under 10 ^-6 ~ 10 ^-8 torr for each material, and used for OLED fabrication.

[Example]

The materials shown in Table 1 corresponding to the green light emitting layer in the above Comparative Example were used instead of CBP, and the remaining materials were used in the same manner as in Comparative Example.

Test example: OLED  Evaluation of device characteristics

The results obtained when the driving voltage, the efficiency and the lifetime of the OLED device manufactured in the above Examples and Comparative Examples are 1000 cd / m 2 and the efficiency is 50% are shown in Table 2 below.

compound Op.V Cd / A @ 1000 cd / m ² Life (T ₅₀ ) Compound 1 4.64 45.5 410 Compound 2 4.68 43.8 400 Compound 5 4.59 47.5 440 Compound 9 4.64 44.9 390 Compound 15 4.66 43.9 400 Compound 16 4.67 43.6 390 Compound 18 4.59 47.8 420 Compound 22 4.48 48.6 420 Compound 23 4.56 46.8 440 Compound 25 4.64 45.5 380 Compound 26 4.75 42.7 370 Compound 30 4.74 42.9 380 Compound 31 4.37 51.6 410 Compound 33 4.38 51.2 430 Compound 45 4.31 52.0 430 Compound 50 4.41 49.8 450 Compound 53 4.41 50.5 460 Compound 54 4.55 48.1 420 Compound 58 4.57 47.7 420 Compound 60 4.67 47.0 410 Compound 63 4.68 47.4 400 Compound 68 4.47 49.5 440 Compound 69 4.48 48.5 450 Compound 73 4.70 45.0 370 Compound 75 4.74 43.3 370 Compound 81 4.65 47.0 410 Compound 85 4.70 44.4 370 Compound 93 4.72 43.4 370 Compound 104 4.73 43.1 360 Compound 107 4.65 47.3 390 Compound 111 4.66 42.9 370 Compound 115 4.84 42.7 360 Compound 126 4.85 43.0 360 Compound 128 4.70 44.5 370 Compound 135 4.71 45.4 370 Compound 141 4.68 43.8 390 Compound 145 4.68 43.7 390 Compound 149 4.70 44.6 400 Compound 156 4.90 44.3 390 Compound 160 4.29 43.5 380 Compound 165 4.87 44.7 400 Compound 171 4.88 44.4 410 Compound 175 4.85 44.6 390 Compound 186 4.91 45.1 410 Compound 201 4.74 45.0 380 Compound 216 4.69 44.1 390 Compound 255 4.94 44.8 400 Compound 271 4.59 43.9 390 Compound 302 4.68 44.3 370 Compound 316 4.91 45.2 360 Comparative Example 6.69 35.2 230

100 substrate
200 anode
300 organic layer
301 hole injection layer
302 hole transport layer
303 luminous layer
304 hole stop layer
305 electron transport layer
306 electron injection layer
400 cathode

Claims (26)

Compounds of formula (I)
[Formula 1a]

In Formula 1a,
R ₁ and R ₂ are independently selected from the group consisting of halogen; Amine; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring or an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic ring; or
Any one of R < ₁ > and R < ₂ > is hydrogen; The other of R < ₁ > and R < ₂ > is halogen; Amine; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; Of C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₁ to C ₂₀ an alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C ₆₀ of, C ₆ to C ₆₀ monocyclic or polycyclic aryl group; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring or an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic ring; or
Any one of R < ₁ > and R < ₂ > is a linear or branched C ₁ to C ₆₀ substituted or unsubstituted alkyl; The other of R < ₁ > and R < ₂ > is halogen; Amine; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon rings or aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic rings;
R ₃ to R ₈ are the same or different and are independently selected from the group consisting of hydrogen, halogen, amine, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, C ₂ to C ₆₀ linear or branched, C ₂ to C ₆₀ linear or branched substituted or unsubstituted alkynyl, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkoxy, C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, C ₂ to the C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Substituted phospholyl (P = O), and C ₁ to C Selected from the group consisting of amine substituted by a ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C ₆₀ of, or adjacent To form an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring or an aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic ring. The compound according to claim 1, wherein any one of R ₁ and R ₂ is hydrogen, and the remaining one of R ₁ and R ₂ is a C ₁₀ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₁ to C ₂₀ an alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, or C ₂ to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C ₆₀ of, C ₆ to C ₆₀ monocyclic or polycyclic aryl group; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Lt; / RTI > The compound according to claim 1, wherein any one of R ₁ and R ₂ is a C ₁ to C ₆₀ straight or branched chain substituted or unsubstituted alkyl, and the remaining one of R ₁ and R ₂ is a C ₆ to C ₆₀ single ring or Substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Lt; / RTI > The compound according to claim 1, wherein R ₁ and R ₂ are the same or different and are C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Lt; / RTI > The compound of claim 1, wherein any one of R ₁ and R ₂ is hydrogen and the other of R ₁ and R ₂ is substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl , Substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted Or an unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted amine. Wherein one of R ₁ and R ₂ is a C ₁ to C ₆₀ straight or branched chain substituted or unsubstituted alkyl and the remaining one of R ₁ and R ₂ is substituted or unsubstituted phenyl, Substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl , Substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzo A substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl, a substituted or unsubstituted carbazolyl, or a substituted or unsubstituted benzothiophene group, Lt; / RTI > is a substituted amine. [Claim _{2] The} compound according to claim 1, wherein R < ₁ > and R < ₂ > are the same or different from each other and are selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, , Substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted phenyl Substituted or unsubstituted benzothiophene groups, substituted or unsubstituted dibenzofuran groups, substituted or unsubstituted dibenzofuran groups, substituted or unsubstituted benzoxazolyl groups, substituted or unsubstituted benzofuran groups, substituted or unsubstituted benzothiophene groups, substituted or unsubstituted dibenzofuran groups, A benzothiophene group, a substituted or unsubstituted indolyl, or a substituted or unsubstituted carbazolyl. 2. The compound of claim 1, wherein any one of R ₁ and R ₂ is hydrogen and the remaining one of R ₁ and R ₂ is selected from biphenyl, triphenyl, naphthyl, anthracenyl, acenaphthylenyl, phenanthrenyl, Naphthyl, phenyl substituted with anthracenyl, substituted phenyl with carbazolyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, phenyl substituted with phenyl and naphthyl, Aryl substituted with phenyl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthracenyl substituted with phenyl, C ₁ -C ₂₀ alkyl, or C _A benzoyl group, a benzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a phenyl group, a phenyl group substituted with an aryl group having ₆ to ₂₀ carbon atoms, a furanyl group, a thienyl group, a pyridyl group, a benzoxazolyl group, Substituted indolyl, carbazolyl, phenyl substituted carbazolyl, triazinyl substituted carbazolyl, di Phenyl-naphthyl-amine, diphenylamine, dinaphthylamine, N-phenyl-fluorenylamine, N-naphthyl-fluorenylamine, Naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorenyl-amine, N-naphthyl-anthracenyl -Amine, N-naphthyl-anthrylphenylamine, N-phenyl-diphenyltriazinylamine, N-naphthyl-diphenyltriazinylamine or N-biphenyl-diphenyltriazinylamine Lt; / RTI > 2. The compound of claim 1 wherein any one of R ₁ and R ₂ is methyl, ethyl or propyl, and the other of R ₁ and R ₂ is phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, acenaphthylenyl, Phenyl substituted with phenyl, phenyl substituted with phenyl, phenyl substituted with phenyl, phenyl substituted with phenyl, phenyl substituted with phenyl, phenyl substituted with phenyl, and phenyl substituted with naphthyl phenyl, diphenyl phosphonate reel substituted phenyl, pyridyl the anthracenyl substituted with phenyl, furanyl phenyl, thienyl, phenyl, naphthyl, phenyl substituted with a naphthyl group substituted with substituted with substituted, C ₁ ~ substituted with a C ₂₀ alkyl or C ₆ ~ C ₂₀ aryl fluorenyl, furanyl, thienyl, pyridyl, benzoxazolyl, benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene Group, N-substituted indolyl with phenyl group, carbazolyl, phenyl substituted carbazolyl, tri Phenyl-naphthyl-amine, diphenylamine, dinaphthylamine, N-phenyl-fluorenyl-amine, N-naphthyl-fluorenyl- Amine, N-naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorenyl- amine, N-naphthyl-diphenyltriazinyl-amine, or N-biphenyl-anthracenyl-amine, N-naphthyl-anthracenyl- Diphenyltriazinyl-amine. ≪ / RTI > A compound according to claim 1, wherein R ₁ and R ₂ are the same or different and are selected from the group consisting of phenyl, biphenyl, triphenyl, naphthyl, acenaphthylenyl, phenanthrenyl, pyrenyl, indenyl, Substituted phenyl with diphenylphosphoryl, phenyl substituted with phenyl, phenyl substituted with carbamoyl, substituted phenyl with carbamoyl, phenyl substituted with carbamoyl, phenyl substituted with carbamoyl, phenyl substituted with carbamoyl, , Phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthracenyl substituted with phenyl, fluoro substituted with C ₁ -C ₂₀ alkyl or C ₆ -C ₂₀ aryl Phenyl substituted carbamoyl, phenyl substituted carbamoyl, carbamoyl, phenyl substituted carbamoyl, phenyl substituted carbamoyl, phenyl substituted carbamoyl, phenyl substituted carbamoyl, phenyl substituted carbamoyl, Triazolyl substituted carbazolyl, or diphenyltriazinyl substituted carbazolyl, Phenyl-naphthyl-amine, diphenylamine, diphenylamine, dinaphthylamine, N-phenyl-fluorenyl-amine, N-naphthyl- N-naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorenyl-amine, N-naphthyl-anthra Amine, N-naphthyl-diphenyltriazinyl-amine, or N-biphenyl-diphenyltriazinyl-amine Lt; / RTI > The compound according to claim 1, wherein R ₃ is C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl, C ₆ to C ₆₀ Membered monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl. A compound according to claim 1, wherein R ₃ is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted thienyl, substituted or unsubstituted furanyl, ≪ / RTI > unsubstituted cyclopropyl, and unsubstituted cyclopropyl. The compound according to claim 1, wherein R ₆ And R ₇ are the same or different and are independently selected from the group consisting of hydrogen, halogen, C ₁ to C ₆ straight or branched chain substituted or unsubstituted alkoxy, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl, and an amine substituted with C ₁ to C ₂₀ alkyl or C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl ≪ / RTI > The compound according to claim 1, wherein R ₆ And R ₇ are the same or different and are independently selected from the group consisting of hydrogen, F, substituted or unsubstituted methoxy, substituted or unsubstituted phenyl, substituted or unsubstituted diphenylamine, substituted or unsubstituted dimethylamine, ≪ / RTI > unsubstituted furanyl, and unsubstituted furanyl. The compound according to claim 1, wherein R ₄ , R ₅ and R ₈ are hydrogen. 1. An organic electroluminescent device comprising a cathode, an anode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by the following Formula 1b:
[Chemical Formula 1b]

In the above formula (1b)
R ₁ to R ₈ are the same or different from each other and independently represent hydrogen; halogen; Amine; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkenyl; C ₂ to C ₆₀ linear or branched, substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; (P = O) substituted with C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And amines substituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Or may be connected to adjacent groups to form aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic hydrocarbon rings or aliphatic or aromatic substituted or unsubstituted monocyclic or polycyclic heterocyclic rings. 16. The compound of claim 16, wherein R ₁ and R ₂ are the same or different and are selected from the group consisting of hydrogen; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted or unsubstituted with C ₁ to C ₂₀ alkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI > 16. The compound of claim 16, wherein R ₁ and R ₂ are the same or different and are selected from the group consisting of hydrogen, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, Substituted or unsubstituted benzenesulfonyl, substituted or unsubstituted benzenesulfonyl, substituted or unsubstituted benzenesulfonyl, substituted or unsubstituted benzenesulfonyl, substituted or unsubstituted benzenesulfonyl, substituted or unsubstituted benzenesulfonyl, substituted or unsubstituted benzenesulfonyl, A substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted indolyl group, or a substituted or unsubstituted carbazolyl group. A compound according to claim 16, wherein R ₁ and R ₂ are the same or different and are selected from hydrogen, methyl, ethyl, propyl, phenyl, biphenyl, triphenyl, naphthyl, acenaphthylenyl, phenanthrenyl, pyrenyl, indenyl, Naphthyl-substituted phenyl, anthracenyl-substituted phenyl, carbazolyl-substituted phenyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, phenyl substituted with phenyl and naphthyl, diphenylphosphoryl Phenyl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthracenyl substituted with phenyl, C ₁ -C ₂₀ alkyl or C ₆ -C _A benzoyl group, a benzothiophene group, a dibenzofurane group, a dibenzothiophene group, an indole N-substituted with a phenyl group, a fluorenyl group substituted with an aryl group having 1 to 20 carbon atoms, a furanyl group, a thienyl group, a pyridyl group, a benzoxazolyl group, Lt; / RTI > substituted carbazolyl, substituted carbazolyl, phenyl substituted carbazolyl, triazinyl substituted carbazolyl, N-phenyl-naphthyl-amine, diphenylamine, dinaphthylamine, N-phenyl-fluorenyl-amine, N-naphthyl-fluorenyl Amine, N-phenyl-biphenyl-amine, N-naphthyl-dibenzofuranyl-amine, N-naphthyl-dibenzothienyl- , N-naphthyl-anthracenyl-amine, N-naphthyl-anthrylphenyl-amine, N-phenyl-diphenyltriazinyl- -Diphenyltriazinyl-amine. ≪ / RTI > A compound according to claim 16, wherein R ₃ is C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl, C ₆ to C ₆₀ A substituted or unsubstituted aryl, a monocyclic or polycyclic substituted or unsubstituted aryl, and a substituted or unsubstituted C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl. A compound according to claim 16, wherein R ₃ is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted thienyl, substituted or unsubstituted furanyl, An unsubstituted cyclopropyl group, and an unsubstituted cyclopropyl group. The method according to claim 16, R ₆ And R ₇ are the same or different and are independently selected from the group consisting of hydrogen, halogen, C ₁ to C ₆ straight or branched chain substituted or unsubstituted alkoxy, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl, and an amine substituted with C ₁ to C ₂₀ alkyl or C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl ≪ / RTI > The method according to claim 16, R ₆ And R ₇ are the same or different and are independently selected from the group consisting of hydrogen, F, substituted or unsubstituted methoxy, substituted or unsubstituted phenyl, substituted or unsubstituted diphenylamine, substituted or unsubstituted dimethylamine, Lt; / RTI > is selected from the group consisting of unsubstituted furanyl and unsubstituted furanyl. The organic electroluminescent device according to claim 16, wherein R ₄ , R ₅ and R ₈ are hydrogen. The organic electroluminescent device according to claim 16, wherein the compound of formula (Ib) is selected from the following compounds:

The organic light emitting device according to claim 16, wherein the organic material layer including the compound of Formula 1b is a light emitting layer.

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