KR20160051654A - Multicyclic compound and organic electronic device using the same - Google Patents

Abstract

In the present specification, polycyclic compounds and organic electroluminescent devices using them are disclosed.

Description

TECHNICAL FIELD [0001] The present invention relates to a polycyclic compound and an organic electroluminescent device using the polycyclic compound.

The present invention relates to a polycyclic compound and an organic electroluminescent device including the polycyclic compound. This application claims the benefit of Korean Patent Application No. 10-2014-0149574 filed with the Korean Intellectual Property Office on October 30, 2014, the entire contents of which are incorporated herein by reference.

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 needed. 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.

Korean Patent Publication No. 2000-0051826

The present invention provides a polycyclic compound and an organic electroluminescent device including the polycyclic compound.

One embodiment of the present disclosure provides compounds represented by Formula 1:

[Chemical Formula 1]

In Formula 1,

X is O, S or NAr,

n is an integer of 0 to 6,

When n is 2 or more, a plurality of R < 5 > s are the same or different from each other,

R1 to R5 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group having two or more rings; A monocyclic to bicyclic substituted or unsubstituted heterocyclic group containing at least one N atom as a hetero atom; Or a heterocyclic group containing at least one of O and S as a heteroatom, or may form a ring by bonding to adjacent groups,

R6 to R10 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two or more adjacent groups out of R 6 to R 10 are bonded to each other to form a ring,

Ar is hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted heteroarylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1, to provide.

The compound according to the present invention can be used as an organic layer material of an organic electroluminescent 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 electroluminescent device. The compound according to one embodiment may be used as a light emitting host material of an organic electroluminescence device, such as a phosphorescent host material. The compound according to another embodiment may be used as an electron transporting layer material of an organic electroluminescence device.

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

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

The present invention provides a compound represented by the above formula (1).

In this specification,

Quot; refers to a moiety that is connected to another substituent.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; A heteroarylamine group; An arylamine group; Or a heterocyclic group, or that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent to which they are linked. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the carbon number of the carbonyl group is not particularly limited,

40 < / RTI > Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. According to another embodiment, the number of carbon atoms in the alkyl group is 3 or more. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylhexyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylhexyl, 4-methylhexyl and 5-methylhexyl.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

When the fluorenyl group is substituted,

,

,

, And

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

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N and S as a heteroatom. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl groups in the aryloxy group, arylthioxy group, arylsulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group and arylamine group are exemplified by the above- same.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group is the same as the above-mentioned alkyl group.

In the present specification, the heteroaryl group in the heteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.

In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.

In the present specification, the term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.

As used herein, the term "adjacent group" means a group in which the substituent is substituted with an atom directly bonded to the atom to which the substituted atom is substituted, a substituent having the closest stereostructure to the substituent, It can mean. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent groups ".

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include phenyl, naphthalene, anthracene, and the like, but are not limited thereto.

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more of the N, O, or S atoms as heteroatoms.

As used herein, an aromatic heterocycle refers to an aromatic ring containing one or more of N, O, or S atoms as heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

In one embodiment of the present disclosure, X is O or S;

In one embodiment of the present disclosure, X is S.

In another embodiment, X is zero.

In one embodiment of the present disclosure, X is NAr.

In one embodiment of the present disclosure, R1 is hydrogen.

In one embodiment of the present disclosure, R 2 is hydrogen.

In one embodiment of the present disclosure, R 3 is hydrogen.

In one embodiment of the present disclosure, R4 is hydrogen.

In one embodiment of the present disclosure, R 1 to R 4 are hydrogen.

In one embodiment of the present specification, two adjacent groups of R 1 to R 4 are bonded to each other to form a ring.

In one embodiment of the present disclosure, R 1 and R 2 combine to form a ring.

In one embodiment of the present disclosure, R 2 and R 3 combine to form a ring.

In one embodiment of the present disclosure, R 3 and R 4 combine to form a ring.

In one embodiment of the present specification, two adjacent groups out of R1 to R4 form a ring by bonding to each other, and the group not bonded to each other among R1 to R4 is hydrogen.

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

In one embodiment of the present specification, two adjacent R < 5 > are bonded to form a ring.

In one embodiment of the present disclosure, R 1 and R 2 combine to form a benzene ring.

In one embodiment of the present disclosure, R 2 and R 3 combine to form a benzene ring.

In one embodiment of the present disclosure, R 3 and R 4 combine to form a benzene ring.

In one embodiment of the present specification, two adjacent R < 5 > are bonded to form a benzene ring.

In one embodiment of the present disclosure, R6 is hydrogen.

In one embodiment of the present disclosure, R7 is hydrogen.

In one embodiment of the present disclosure, R8 is hydrogen.

In one embodiment of the present disclosure, R9 is hydrogen.

In one embodiment of the present disclosure, R10 is hydrogen.

In one embodiment of the present disclosure, R6 to R10 are hydrogen.

In another embodiment, Ar is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar is an aryl group which is substituted or unsubstituted with a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted chrysinyl group, a substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinolinol group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted phenanthroline group.

In one embodiment of the present specification, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted chrysinyl group, a substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinolinol group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted phenanthroline group, wherein the substituted or unsubstituted ring is at least one member selected from the group consisting of a deuterium, a nitrile group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group and a substituted or unsubstituted heteroaryl group Substituted or unsubstituted.

In one embodiment of the present specification, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted chrysinyl group, a substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinolinol group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted phenanthroline group, wherein the substituted or unsubstituted ring is selected from the group consisting of deuterium, a nitrile group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted arylamine group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted thiophene group, A substituted or unsubstituted quinoline group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted quinazoline group, A substituted or unsubstituted dibenzofuran group and a substituted or unsubstituted anthracenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted naphthyl group.

In one embodiment of the present disclosure, Ar is substituted or unsubstituted biphenyl.

In one embodiment of the present specification, Ar is a substituted or unsubstituted anthracenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted pyrenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted phenanthrenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted fluoranthenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted chrysenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted pyrimidine group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted triazine group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted quinoline group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted quinolinol group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted dimethylfluorenyl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted dibenzofurane group.

In one embodiment of the present specification, Ar is a phenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a biphenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with an arylamine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a diphenylamine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenylbiphenylamine group.

In one embodiment of the present disclosure, Ar is a phenyl group substituted with a bisbiphenylamine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenyl group and a biphenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a naphthyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a quinoline group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a quinazoline group.

In one embodiment of the present disclosure, Ar is phenyl substituted with phenyl (phenylcarbazole) amine.

In one embodiment of the present disclosure, Ar is a phenyl group substituted with phenyl (dibenzothiophene) amine.

In one embodiment of the present disclosure, Ar is a phenyl group substituted with phenyl (dibenzofuran) amine.

In one embodiment of the present specification, Ar is a phenyl group substituted with a dimethylfluorenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a nitrile group.

In one embodiment of the present disclosure, Ar is a phenyl group substituted with deuterium.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenylthiophene group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenyl furan group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a biphenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a terphenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a quaterphenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a triphenylamine group.

In one embodiment of the present specification, Ar is a biphenyl group substituted with a phenylbiphenylamine group.

In one embodiment of the present specification, Ar is a biphenyl group substituted with a bisbiphenylamine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a diphenylpyridine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenylbiphenylpyridine group.

In one embodiment of the present disclosure, Ar is a phenyl group substituted with a bisbiphenylpyridine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenylbiphenylpyrimidine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a bisbiphenylpyrimidine group.

In one embodiment of the present specification, Ar is a phenyl group substituted by a diphenyltriazine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenylbiphenyltriazine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a bisphenyltriazine group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenylquinazoline group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a naphthylquinazoline group.

In one embodiment of the present disclosure, Ar is a phenyl group substituted with a biphenylquinazoline group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a dimethylfluorenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted by a dimethylphenylfluorenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted by a dimethylnaphthylfluorenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted by a dimethylpyridine fluorenyl group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a phenylcarbazole group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a dibenzothiophene group.

In one embodiment of the present specification, Ar is a phenyl group substituted with a dibenzofurane group.

In one embodiment of the present specification, Ar is a phenyl group substituted with an anthracenyl group.

In one embodiment of the present specification, Ar is a biphenyl group substituted with a naphthyl group.

In one embodiment of the present specification, Ar is a biphenyl group substituted with quinoline.

In one embodiment of the present specification, Ar is a biphenyl group substituted with dinaphthylamine.

In one embodiment of the present specification, Ar is a naphthyl group.

In one embodiment of the present specification, Ar is a naphthyl group substituted with a dimethylfluorenyl group.

In one embodiment of the present specification, Ar is a naphthyl group substituted with a naphthyl group.

In one embodiment of the present disclosure, Ar is an anthracenyl group.

In one embodiment of the present disclosure, Ar is an anthracenyl group substituted with a phenyl group.

In one embodiment of the present specification, Ar is an anthracenyl group substituted with a naphthyl group.

In one embodiment of the present specification, Ar is an anthracenyl group substituted with a dimethylfluorenyl group.

In one embodiment of the present disclosure, Ar is an anthracenyl group substituted with a cyanodimethylfluorenyl group.

In one embodiment of the present specification, Ar is a pyridine group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a pyridine group substituted with a biphenyl group.

In one embodiment of the present specification, Ar is a pyridine group substituted with a phenyl group and a biphenyl group.

In one embodiment of the present specification, Ar is a pyrimidine group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a pyrimidine group substituted with a biphenyl group.

In one embodiment of the present specification, Ar is a pyrimidine group substituted with a phenyl group and a biphenyl group.

In one embodiment of the present specification, Ar is a triazine group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a triazine group substituted with a biphenyl group.

In one embodiment of the present disclosure, Ar is a quinoline group.

In one embodiment of the present specification, Ar is a quinazoline group.

In one embodiment of the present specification, Ar is a quinazoline group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a quinazoline group substituted with a naphthyl group.

In one embodiment of the present specification, Ar is a quinazoline group substituted with a biphenyl group.

In one embodiment of the present specification, Ar is a quinazoline group substituted with a phenylnaphthyl group.

In one embodiment of the present specification, Ar is a dimethylfluorenyl group.

In one embodiment of the present specification, Ar is a dimethylfluorenyl group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a dimethylfluorenyl group substituted with a naphthyl group.

In one embodiment of the present specification, Ar is a dimethylfluorenyl group substituted with a pyridine group.

In one embodiment of the present specification, Ar is a carbazole group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a dibenzothiophene group.

In one embodiment of the present specification, Ar is a dibenzofurane group.

In one embodiment of the present specification, Ar is a pyrenyl group.

In one embodiment of the present specification, Ar is a phenanthrenyl group.

In one embodiment of the present specification, Ar is a phenanthroline group.

In one embodiment of the present disclosure, Ar is a chrysenyl group.

In one embodiment of the present specification, Ar is a fluoranthenyl group.

In one embodiment of the present specification, Ar is a fluoranthenyl group substituted with a phenyl group.

In one embodiment of the present specification, Ar is a fluoranthenyl group substituted with two phenyl groups.

In one embodiment of the present invention, the compound represented by Formula 1 is any one selected from the following structural formulas.

The present invention also provides an organic electroluminescent device comprising the aforementioned compound.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 do.

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

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of the general formula (1).

In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1).

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound of the above formula (1).

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer that simultaneously transports electrons and electrons injects the compound of Formula 1 and further includes an n-type dopant.

In one embodiment of the present invention, the electron transporting layer, the electron injection layer, or the layer that simultaneously transports electrons and electrons injects the compound of Formula 1 and further includes a metal complex.

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer that simultaneously transports electrons and electrons injects the compound of Formula 1 and further includes LiQ (Lithium Quinolate).

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and one or more of the electron transporting layers include the compound of the above formula (1).

In another embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes the compound of the above formula (1).

In another embodiment, the compound of Formula 1 is a phosphorescent host material or a fluorescent host material.

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

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

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

1, an organic electroluminescent 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 electroluminescent 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, an electron transport layer 304, and an electron injection layer 305. 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 electroluminescent device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the compound of the above formula (1).

When the organic electroluminescent device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

 The organic electroluminescent device of 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 1, that is, the compound represented by Formula 1. [

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

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic electroluminescent device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic electroluminescent device can also be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

In another embodiment, the first electrode is a cathode and the second electrode is a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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

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

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

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

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

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

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

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

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

In one embodiment of the present invention, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic electroluminescent device.

Hereinafter, the present invention will be described in detail with reference to the following embodiments. However, the embodiments according to the present disclosure can be modified into various other forms, and the scope of the present application is not construed as being limited to the above-described embodiments. The embodiments of the present application are provided to enable those skilled in the art to more fully understand the present invention.

<Production Example>

[Preparation Example 1: Synthesis of 1-g]

Substance 1-a (Cas No. 1592-95-6, 1 eq) and Ar substituted with a halogen group (X = I or Br, 1.1 eq) were placed in a two neck flask. Then, copper iodide (CuI) (0.2 eq), 1,10-phenanthroline (0.2 eq) and xylene were added thereto, followed by reflux stirring for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure, and 1-b was obtained by column chromatography.

A nitrogen atmosphere was created in a two neck flask. 1-b (1 eq) was completely dissolved in tetrahydrofuran (THF) and the temperature was maintained at -78 ° C. N-Butyllithium (nBuLi) (1 eq) was slowly added thereto. After the addition was completed, the mixture was stirred for 30 minutes, and then B (OMe) ₃ was slowly added dropwise. The mixture was stirred for 30 minutes and then an excess of 1N aqueous hydrochloric acid solution (HCl solution) was added. Then, the temperature was gradually raised to room temperature. When the reaction was completed, trichloromethane (CHCl ₃ ) was used for extraction, and the organic layer was washed with magnesium sulfate (MgSO ₄ ) to remove water. After removal of the solvent, compound 1-c was obtained by recrystallization from ethanol.

Compound 1-c (1.1 eq), 2-iodo-bromobenzene (1.0 eq) and Pd (PPh ₃ ) ₄ (0.02 eq) were dissolved in 1,4-dioxane -dixoane) was added and stirred. A solution was prepared by adding potassium carbonate (K ₂ CO ₃ , 3 eq) and water (H ₂ O). And the mixture was refluxed for 3 hours and stirred. After the reaction was completed, the reaction mixture was cooled to room temperature and the organic layer was separated. The organic solvent was removed by distillation under reduced pressure, and Compound 1-d was obtained by column chromatography.

(1 eq), P, P-diphenyl-Phosphinic chloride (Cas No. 1499-21-4) - (1.5 eq), Ni (dppp) Cl ₂ (0.02 eq) and K ₂ CO ₃ (3 eq). Then, 1,4-dioxane (1,4-dioxane) was refluxed and stirred for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Compound 1-e was obtained by column chromatography.

The two neck flask was made to have a nitrogen atmosphere. Compound 1-e (1 eq) was dissolved in anhydrous toluene and maintained at -116 ° C. Trichlorosilane (HSiCl ₃ , 5 eq) and triethylamine (NEt ₃ , 5.5 eq) were charged at -116 ° C. After slowly raising the temperature to room temperature, the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, saturated sodium carbonate (NaHCO ₃ ) saturated solution was sufficiently added thereto, and the mixture was stirred at room temperature for 10 minutes. The solvent was removed under reduced pressure, and Compound 1-f was obtained by column chromatography.

Compound 1-f (1 eq), Pd (OAc) ₂ (0.05 eq) and anhydrous toluene were added to a sealed tube. Nitrogen was fully charged, then blocked with a stopper and heated at 160 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, a few drops of hydrogen peroxide (H ₂ O ₂ , ca. 30%) were added thereto, and the mixture was stirred at room temperature for 30 minutes. The solvent was completely removed and the compound 1-g was obtained by column chromatography.

[Production Example 1-1: Synthesis of 1-g '] [

The material 1-a '(Cas No. 1592-95-6, 20 g, 81.3 mmol, 1 eq) and Iodobenzene (18.23 g, 89.4 mmol, 1.1 eq) were placed in a two neck flask . Then, 150 ml of copper iodide (CuI) (3.1 g, 16.3 mmol, 0.2 eq), 1,10-phenanthroline (3.0 g, 16.3 mmol, 0.2 eq) and xylene And the mixture was stirred at reflux for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. 1-b '(22.4 g, yield 86%) was obtained by column chromatography.

A nitrogen atmosphere was created in a two neck flask. 1-b '(22.4 g, 69.5 mmol, 1 eq) was completely dissolved in 150 ml of anhydrous tetrahydrofuran (THF) and the temperature was maintained at -78 ° C. using a dry ice / actone bath. To the mixture was slowly added n-butyllithium (nBuLi) (27.8 ml, 69.5 mmol, 1 eq) having a concentration of 2.5 M and the mixture was stirred for 30 minutes after the addition. B (OMe) ₃ (10.8 g, 104.25 mmol, 1.5 eq) Was slowly added dropwise. The mixture was stirred for 30 minutes and then an excess of 1N aqueous hydrochloric acid solution (HCl solution) was added. Then, the temperature was gradually raised to room temperature. The organic layer was extracted with trichloromethane (CHCl ₃ ), and water was removed using magnesium sulfate (MgSO ₄ ). Compound 1-c '(18 g, yield 90.2%) was obtained by recrystallization from ethanol.

(18 g, 62.7 mmol, 1.1 eq), 2-iodo-bromobenzene (16.1 g, 57.0 mmol, 1.0 eq), Pd (PPh ₃ ) ₄ , 1.14 mmol, 0.02 eq) was added to 150 ml of 1,4-dioxane, followed by stirring. Here, a solution was prepared by adding potassium carbonate (K ₂ CO ₃ ) (23.6 g, 171 mmol, 3 eq) and 60 ml of water (H ₂ O). And the mixture was refluxed for 3 hours and stirred. After the reaction was completed, the mixture was cooled to room temperature and the organic layer was separated. The organic solvent was removed by distillation under reduced pressure, and compound 1-d '(17.7 g, yield 78%) was obtained by column chromatography.

The compound 1-d '(17.7 g, 44.4 mmol, 1 eq), P, P-diphenyl-Phosphinic chloride (Cas No. 1499-21-4) (15.8 g, 66.7 mmol, 1.5 eq), Ni (dppp) Cl ₂ (0.37 g, 88.8 mmol, 0.02 eq) and K ₂ CO ₃ (18.4 g, 133.2 mmol, 3 eq). And 1,4-dioxane (1,4-dioxane) under reflux for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Compound 1-e '(20.2 g, yield 87.6%) was obtained by column chromatography.

After the two neck flask was made to have a nitrogen atmosphere, compound 1-e '(20.2 g, 38.9 mmol, 1 eq) was dissolved in anhydrous toluene and maintained at -116 ° C. using a liquid nitrogen / ethanol bath. Trichlorosilane (HSiCl ₃ ) (26.3 g, 194.5 mmol, 5 eq) and triethylamine (NEt ₃ ) (21.6 g, 214.0 mmol, 5.5 eq). After slowly raising the temperature to room temperature, the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, saturated sodium carbonate (NaHCO ₃ ) saturated solution was sufficiently added thereto, and the mixture was stirred at room temperature for 10 minutes. The solvent was removed under reduced pressure, and the compound 1-f '(15.7 g, yield 80.1%) was obtained by column chromatography.

The compound 1-f '(15.7 g, 31.2 mmol, ₁ eq), Pd (OAc) ₂ (0.35 g, 1.6 mmol, 0.05 eq) and 50 ml of anhydrous toluene were placed in a sealed tube. Nitrogen was fully charged, then blocked with a stopper and heated at 160 ° C for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, a few drops of hydrogen peroxide (H ₂ O ₂ , ca. 30%) were added thereto, and the mixture was stirred at room temperature for 30 minutes. After the solvent was completely removed, the compound 1-g '(6.3 g, yield 45.8%) was obtained by column chromatography.

[Preparation Example 2: synthesis of 2-g]

The synthesis was conducted in the same manner as in Preparation Example 1, except that 1-g was prepared using 2-a (Cas No. 21064-34-6) instead of compound 1-a.

[Preparation Example 3: Synthesis of 3-g]

1-g was prepared by using 3-a (Cas No. 1698-16-4) instead of the compound 1-a in Preparation Example 1.

[Preparation Example 4: Synthesis of 4-e]

G was prepared in the same manner as in Production Example 1 except that 4-a (Cas No. 668983-97-9) was used instead of 1-c.

 [Preparation Example 5: Synthesis of 5-e]

1-g was prepared by using 5-a (Cas No. 402936-15-6) instead of Compound 1-c in Preparation Example 1.

The following compounds 1 to 16 were prepared using Preparation Examples 1, 1-1, and 2 to 5, and are shown in Table 1 below.

Compound No. Ar-X compound m / z Compound No. Ar-X compound m / z One

CAS #
591-50-4

441 2

CAS #
1628067-38-8

569 3

CAS #
612-55-5

491 4

CAS #
144981-85-1

557 5

CAS #
1591-31-7

517 6

CAS #
502161-03-7

606 7

CAS #
38257-52-2

608 8

CAS #
5896-29-7

531 9

CAS #
777883-39-3

672 10

CAS #
1612853-56-1

623 11

CAS #
7379-67-1

446 12

CAS #
55691-84-4

541 13

CAS #
591-50-4

491 14

CAS #
591-50-4

491 15 -

382 16 -

366

<Examples>

&Lt; Comparative Example 1 &

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

[NPB]

Subsequently, a tris (4- (9H-carbazol-9-yl) phenyl) amine (TCTA) was added to the hole transport layer in a thickness of 100 angstrom To form an electron blocking layer.

[TCTA]

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

[BH]

[BD]

[ET1]

[LiQ]

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

<Experimental Example 1-1>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 1 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-2>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 2 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-3>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 3 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 4 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-5>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 5 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 6 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 7 was used instead of Compound ET1 in Comparative Example 1.

 <Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 8 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-9>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 9 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 10 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 11 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 12 was used in place of Compound ET1 in Comparative Example 1.

<Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 13 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 14 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-15>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 15 was used instead of Compound ET1 in Comparative Example 1.

<Experimental Example 1-16>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound 16 was used instead of Compound ET1 in Comparative Example 1.

The results of Table 2 were obtained when current was applied to the organic light emitting device manufactured in Comparative Example 1 and Experimental Examples 1-1 to 1-16.

compound
(Electron transport layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Comparative Example 1 Compound ET1 4.19 5.25 (0.138, 0.127) Experimental Example 1-1 Compound 1 3.52 5.56 (0.139, 0.124) Experimental Example 1-2 Compound 2 3.53 5.52 (0.138, 0.125) Experimental Example 1-3 Compound 3 3.54 5.53 (0.138, 0.123) Experimental Examples 1-4 Compound 4 3.50 5.52 (0.134, 0.124) Experimental Examples 1-5 Compound 5 3.54 5.54 (0.136, 0.125) Experimental Example 1-6 Compound 6 3.53 5.52 (0.136, 0.124) Experimental Example 1-7 Compound 7 3.52 5.56 (0.137, 0.126) Experimental Examples 1-8 Compound 8 3.54 5.55 (0.136, 0.124) Experimental Examples 1-9 Compound 9 3.55 5.54 (0.137, 0.127) Experimental Example 1-10 Compound 10 3.56 5.52 (0.136, 0.125) Experimental Example 1-11 Compound 11 3.57 5.53 (0.137, 0.126) Experimental Example 1-12 Compound 12 3.53 5.52 (0.136, 0.126) Experimental Example 1-13 Compound 13 3.51 5.54 (0.137, 0.125) Experimental Example 1-14 Compound 14 3.52 5.52 (0.137, 0.125) Experimental Example 1-15 Compound 15 3.56 5.53 (0.138, 0.125) Experimental Example 1-16 Compound 16 3.57 5.52 (0.136, 0.125)

100: substrate
200: anode
300: organic layer
301: Hole injection layer
302: hole transport layer
303: light emitting layer
304: electron transport layer
305: electron injection layer
400: cathode

Claims (12)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X is O, S or NAr,
n is an integer of 0 to 6,
When n is 2 or more, a plurality of R &lt; 5 &gt; s are the same or different from each other,
R1 to R5 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group having two or more rings; A monocyclic to bicyclic substituted or unsubstituted heterocyclic group containing at least one N atom as a hetero atom; Or a heterocyclic group containing at least one of O and S as a heteroatom, or may form a ring by bonding to adjacent groups,
R6 to R10 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two or more adjacent groups out of R 6 to R 10 are bonded to each other to form a ring,
Ar is hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted heteroarylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The compound according to claim 1, wherein R6 to R10 are all hydrogen. The compound according to claim 1, wherein X is O or S. 2. The compound according to claim 1, wherein X is NAr. 5. The compound according to claim 4, wherein Ar is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted chrysinyl group, a substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinolinol group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted phenanthroline group. The compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following structural formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 6. 5. The organic electroluminescent device according to claim 1, An electroluminescent device. The organic electroluminescent device according to claim 7, wherein the organic compound layer containing the compound is a light emitting layer. The organic electroluminescent device according to claim 7, wherein the organic compound layer containing the compound is an electron injection layer, an electron transport layer, or an electron injection and transport layer. [Claim 7] The organic electroluminescent device according to claim 7, wherein the organic compound layer containing the compound is a hole injection layer, a hole transport layer, or a hole injection and transport layer. The organic electroluminescent device according to claim 7, wherein the compound is a phosphorescent host material or a fluorescent host material. 8. The organic electroluminescent device according to claim 7, wherein the organic material layer includes two or more electron transporting layers, and one or two or more layers of the electron transporting layer include the compound.

Images