KR101784562B1

KR101784562B1 - Hetero-cyclic compound and organic light emitting device comprising the same

Info

Publication number: KR101784562B1
Application number: KR1020150133183A
Authority: KR
Inventors: 차용범; 김진주
Original assignee: 주식회사 엘지화학
Priority date: 2015-01-13
Filing date: 2015-09-21
Publication date: 2017-10-11
Also published as: KR20160087331A

Abstract

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

The present application claims the benefit of the filing date of Korean Patent Application No. 10-2015-0006399 filed with the Korean Intellectual Property Office on Jan. 13, 2015, the entire contents of which are incorporated herein by reference.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer has a multilayer structure composed of different materials. For example, the organic material layer includes a hole injection layer, a hole transport layer, an electron blocking layer light emitting layer, an electron transport layer, . When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

International Patent Application Publication No. 2003-012890

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

According to one embodiment of the present invention, there is provided a heterocyclic compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₃ and Y are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; 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 silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

a and c are the same or different and each independently represents an integer of 1 to 4,

b is 1 or 2,

when a is 2 or more, R < ₁ > are the same or different from each other,

when b is 2, R ₂ are the same or different from each other,

When c is 2 or more, R ₃ are the same or different from each other.

According to an embodiment of the present invention, there is also provided 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 above-described heterocyclic compound do.

The heterocyclic compound according to one embodiment of the present invention can be used as a material for an organic material layer of an organic light emitting device requiring a high current since its glass transition temperature is 100 ° C or higher and has excellent thermal stability in an organic light emitting device .

In addition, the heterocyclic compound according to one embodiment of the present invention has a large band gap, so that it is possible to control an appropriate HOMO or LUMO energy. Therefore, the organic light emitting device including the organic EL device can improve the efficiency, improve the driving voltage and / or the lifetime characteristics.

1 shows an organic light emitting device 10 according to an embodiment of the present invention.
2 shows an organic light emitting element 11 according to another embodiment 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, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

Examples of substituents in the present specification are described below, but are not limited thereto.

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

As used herein, the term " substituted or unsubstituted " A halogen group; Knit Reel; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy 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 silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. Means that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent connected thereto. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification,

Quot; refers to a moiety bonded to another substituent or bond.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. 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 an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the 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 30 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 this specification, the amine group is -NH ₂ ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, N-9- An amine group, a diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-biphenylfluorenylamine group, An N-phenylpiperazinylamine group, an N-phenyl spirobifluorenylamine group, an N-biphenyl spirobifluorenylamine group, an N-biphenyldibenzofuranylamine group, Phenylbenzopyranylamine group, an N-phenyldibenzofurylamine group, an N-phenylbiphenylamine group, an N-phenylcarbazolylamine group, an N-biphenylcarbazolylamine group, , N-phenyldibenzothiophenylamine group, N-biphenylnaphthylamine group, N-biphenylterphenylamine group, N-phenylphenylamine group, N-phenylnaphthylamine group, A perfluorenylamine group, a perfluorenylamine group, a perfluorenylamine group, a perfluorenylamine group, a perfluorenylamine group, a perfluorenylamine group, a perfluorenylamine group, a perfluorenylamine group, And the like, but the present invention is not limited thereto.

In the present specification, the N-alkylarylamine amine group means an amine group in which N in the amine group is substituted with an alkyl group and an aryl group.

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group in the alkylamine group, the N-alkylarylamine group, the N-alkylheteroarylamine group, the alkylthio group and the alkylsulfoxy group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. 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 silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ R ₁₀₂ , wherein R ₁₀₀ , R ₁₀₁ and R ₁₀₂ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, dimethylphosphine oxide, and the like, but is not limited thereto.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific 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 crycenyl group, a fluorenyl group and a fluoranthenyl group.

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

When the fluorenyl group is substituted,

,

,

,

,

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

In the present specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfoxy group, the N-alkylarylamine group, the N-arylheteroarylamine group, and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, Phenanthryloxy, 9-phenanthryloxy and the like. Examples of the arylthioxy group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenyl And the like. Examples of the arylsulfoxy group include a benzene sulfoxy group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having two or more of the aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, A thiazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidyl group, A benzoimidazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiophene group, a dibenzothiophene group, a benzoimidazolyl group, a benzoimidazolyl group, a benzimidazolyl group, A furanyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a benzoquinazolinyl group, an indolofluorenyl group , Indolocarbazolyl group, dibenzocarbazolyl group, benzoquinolinyl group, benzoin Sat furanoid group, benzo naphthyl Totti but include thiophene group, a dibenzo furanoid group and possess noksa page group, and the like.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.

According to one embodiment of the present invention, R ₁ to R ₃ are hydrogen.

According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may be represented by Formula 2 below.

(2)

In formula (2), Y has the same definition as in formula (1).

According to one embodiment of the present invention, in Formula 1, Y is a substituted or unsubstituted diarylamine group; A substituted or unsubstituted diheteroarylamine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, Y is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted crecenyl group; A substituted or unsubstituted quaterphenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted perylenyl group; A substituted or unsubstituted thiazinyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinazolinyl group; A substituted or unsubstituted benzoquinolinyl group; A substituted or unsubstituted phenanthrolinyl group; A substituted or unsubstituted quinoxalinyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzonaphthofuranyl; A substituted or unsubstituted benzonaphthothiophene group; A substituted or unsubstituted dimethylphosphine oxide group; Substituted or unsubstituted diphenylphosphine oxide; Substituted or unsubstituted dinaphthylphosphine oxide; A substituted or unsubstituted benzoxazolyl group; A substituted or unsubstituted benzothiazolyl group; A substituted or unsubstituted benzimidazolyl group; A substituted or unsubstituted triphenylsilyl group; A substituted or unsubstituted phenothiazinyl group; A substituted or unsubstituted phenoxazinyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted N-phenylnaphthylamine group; A substituted or unsubstituted N-phenylbiphenylamine group; A substituted or unsubstituted N-phenylphenanthrenylamine group; A substituted or unsubstituted N-biphenylnaphthylamine group; A substituted or unsubstituted divinylamine group; A substituted or unsubstituted N-biphenyl phenanthrenyl amine group; A substituted or unsubstituted dinaphthylamine group; A substituted or unsubstituted N-quaterphenylfluorenylamine group; A substituted or unsubstituted N-terphenylfluorenylamine group; A substituted or unsubstituted N-biphenyltriphenylamine group; A substituted or unsubstituted N-biphenylfluorenylamine group; A substituted or unsubstituted N-phenylfluorenylamine group; A substituted or unsubstituted N-naphthylfluorenylamine group; A substituted or unsubstituted N-phenanthrenyl fluorenylamine group; A substituted or unsubstituted difluorenylamine group; A substituted or unsubstituted N-phenyltriphenylamine group; A substituted or unsubstituted N-phenylcarbazolylamine group; A substituted or unsubstituted N-biphenylcarbazolylamine group; A substituted or unsubstituted N-phenylbenzocarbazolylamine group; A substituted or unsubstituted N-biphenylbenzocarbazolylamine group; A substituted or unsubstituted N-fluorenylcarbazolylamine group; A substituted or unsubstituted benzocarbazolyl group; A substituted or unsubstituted dibenzocarbazolyl group; A substituted or unsubstituted carbazolyl group; Substituted or unsubstituted

; Substituted or unsubstituted

; And a structure represented by the following formula (a)

---- means a moiety directly connected to N in the above formula (1).

(A)

In the above formula (a)

X ₁ to X ₁₂ are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; And a substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent X ₁ to X ₁₂ are connected to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring or substituted or unsubstituted C 6 -C 30 hydrocarbon ring Or an unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms,

Is linked to the formula (1) through any one of X ₁ to X ₁₂ .

According to one embodiment of the present invention, in the formula (a), X ₁ to X ₁₂ are hydrogen.

According to one embodiment of the present invention, in Formula (a), X ₁₁ and X ₁₂ are connected to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 6 to 20 carbon atoms.

According to one embodiment of the present invention, in Formula (a), X ₁₁ and X ₁₂ are connected to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 6 to 10 carbon atoms.

According to one embodiment of the present invention, in the formula (a), X ₁₁ and X ₁₂ are connected to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, in the above formula (a), X ₁₁ and X ₁₂ are connected to each other to form a benzene ring.

According to one embodiment of the present disclosure, Y is a phenyl group; A biphenyl group; A phenanthrenyl group; Naphthyl group; A terphenyl group; A fluorenyl group; Anthracenyl group; A crycenyl group; A quaterphenyl group; A spirobifluorenyl group; Pyrenyl; A triphenylrenyl group; A perylenyl group; Triazinyl groups; Pyrimidyl; A pyridyl group; A quinolinyl group; A quinazolinyl group; Benzoquinolinyl group; Phenanthrolinyl group; A quinoxalinyl group; A dibenzofuranyl group; A dibenzothiophene group; Benzonaphthofuranyl; A benzonaphthothiophene group; Dimethylphosphine oxide group; Diphenylphosphine oxide; Dinaphthylphosphine oxide; Benzoxazolyl group; Benzothiazolyl group; A benzimidazolyl group; Triphenylsilyl groups; A phenothiazinyl group; A phenoxazinyl group; Thiophene group; Diphenylamine group; N-phenylnaphthylamine group; N-phenylbiphenylamine group; N-phenylphenanthrenylamine group; An N-biphenylnaphthylamine group; A divinylamine group; An N-biphenyl phenanthrenyl amine group; A dinaphthylamine group; An N-quaterphenylfluorenylamine group; An N-terphenylfluorenylamine group; An N-biphenyltriphenylamine group; An N-biphenylfluorenylamine group; N-phenylfluorenylamine group; N-naphthylfluorenylamine group; N-phenanthrenyl fluorenylamine group; A difluorenyl amine group; An N-phenyltriphenylamine group; N-phenylcarbazolylamine group; An N-biphenylcarbazolylamine group; N-phenylbenzocarbazolylamine group; An N-biphenylbenzocarbazolylamine group; N-fluorenylcarbazolylamine group; Benzocarbazolyl group; A dibenzocarbazolyl group; A carbazolyl group;

;

;

;

;

;

;

;

;

;

;

;

;

; And

, &Lt; / RTI >

Y is deuterium; A fluorine group; A nitrile group; Methyl group; t-butyl group; A phenyl group; A biphenyl group; Naphthyl group; A fluorenyl group; A phenanthrenyl group; A carbazolyl group; Benzocarbazolyl group; A pyridyl group; Triazinyl groups; A triphenylrenyl group; Pyrimidyl; A quinolinyl group; A dibenzofuranyl group; A dibenzothiophene group; A benzimidazolyl group; Benzothiazolyl group; Benzoxazolyl group; Thiophene group; Dimethylphosphine oxide group; A diphenylphosphine oxide group; A dinaphthylphosphine oxide group; A trimethylsilyl group; Triphenylsilyl groups; Diphenylamine group; A divinylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; An N-biphenylfluorenylamine group; And

&Lt; RTI ID = 0.0 > and / or < / RTI >

According to one embodiment of the present specification, Y may be selected from any one of substituents of the following [A-1] to [A-5].

[A-1]

[A-2]

[A-3]

[A-4]

[A-5]

In the above substituent, --- denotes a site directly connected to N in the above formula (1).

According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of the following Compounds 1 to 144.

According to one embodiment of the present disclosure, there is provided a liquid crystal display 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 a heterocyclic compound represented by the general formula (1). The heterocyclic compound according to one embodiment of the present invention, that is, the heterocyclic compound represented by the general formula (1), is a core having a structure including both a quaterphenyl and an indolocarbazole. The core having a structure including both the quaterphenyl and indolocarbazole is easily reduced and has an n-type property having an electrochemically stable state at the time of reduction and a p-type having an electrochemically stable state at the time of oxidation - type properties at the same time. Accordingly, the heterocyclic compound represented by Formula 1 is suitable for use in an organic material layer of an organic light emitting device.

The organic material layer of the organic light emitting device of the present invention 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 light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.

2 shows a structure in which a first electrode 30, a hole injecting layer 60, a hole transporting layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transporting layer 90, 100 and a second electrode 50 are sequentially laminated on a transparent substrate 100. In this case, 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

According to one embodiment of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound represented by the above formula (1).

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1).

According to another embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by Formula 1 as a phosphorescent host of the light emitting layer.

According to one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transporting and electron injection, and the electron transporting layer, the electron injecting layer, And a heterocyclic compound represented by the above formula (1).

According to an embodiment of the present invention, the organic material layer may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

The organic light emitting device of the present invention is manufactured by materials and methods known in the art except that one or more of the organic layers include the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above formula (1) .

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

For example, the organic light emitting 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 metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

According to another embodiment of the present invention, 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, LiO ₂ / Al, and Mg / Ag, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from the electrode as a hole injecting material and a hole injecting effect for injecting holes in the anode as a hole injecting material and an excellent hole injecting effect for a light emitting layer or a light emitting material , The migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and also the ability to form thin films 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 electron blocking layer is a layer which can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

The light emitting material of the light emitting layer 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 high 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 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 may be 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 heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. 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 of the electron transporting layer is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the cathode to the light emitting layer. This large material 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, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

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

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

Compound A, which is a starting material used in the following Production Examples, can be produced by the following general formula (1), but is not limited thereto.

[Formula 1]

In the above general formula 1, Ullmann reaction and Suzuki coupling reaction were performed twice using 1-bromocarbazole (TCI: B4816, CAS: 16807-11-7). Finally, triethyl phosphite was dissolved in a solvent , And the compound A can be prepared by refluxing.

Manufacturing example

< Manufacturing example 1-1>

[Compound 1]

To a 500 ml round-bottomed flask under nitrogen, compound A (10 g, 17.86 mmol) and bromobenzene (3.06 g, 19.64 mmol) were completely dissolved in 120 ml of xylene and sodium tert-butoxide (2.23 g, 23.18 mmol) - after loading the tert -butylphosphine) palladium (0) ( 0.09g, 0.18mmol) was added and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to give Compound 1 (8.25 g, yield: 72%).

MS [M + H] < ⁺ > = 637

< Manufacturing example 1-2>

[Compound 2]

Compound A (10g, 17.86mmol) and 4-bromo-1,1'-biphenyl (4.56g, 19.64mmol) were completely dissolved in 120ml of xylene in a 500ml round bottom flask under nitrogen atmosphere and sodium tert-butoxide (2.23g, 23.18 mmol), and bis (tri- tert- butylphosphine) palladium (0) (0.09 g, 0.18 mmol) were added thereto, followed by heating and stirring for 4 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (230 ml) to obtain Compound (2) (10.92 g, yield: 86%).

MS [M + H] < ⁺ > = 713

< Manufacturing example 1-3>

[Compound 21]

Compound A (10 g, 17.86 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.34 g, 19.64 mmol) were dissolved in 160 ml of xylene in a 500 ml round bottom flask under nitrogen atmosphere and sodium tert-butoxide g, 23.18 mmol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added and the mixture was heated with stirring for 4 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (230 ml) to obtain Compound 21 (10.65 g, yield: 79%).

MS [M + H] < ⁺ > = 753

< Manufacturing example 1-4>

[Compound 68]

Compound A (10 g, 17.86 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (5.24 g, 19.64 mmol) were dissolved in 260 ml of xylene in a 500 ml round- -butoxide (2.23 g, 23.18 mmol) was added, and bis (tri- tert- butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added and the mixture was heated with stirring for 12 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (450 ml) to obtain Compound 68 (13.11 g, yield: 93%).

MS [M + H] < ⁺ > = 792

< Manufacturing example 1-5>

[Compound 100]

Compound A (10 g, 17.86 mmol) and 2- (4-bromophenyl) dibenzo [b, d] furan (6.32 g, 19.64 mmol) were dissolved in 180 ml of xylene in a 500 ml round- (0.09 g, 0.18 mmol) of bis (tri- tert- butylphosphine) palladium (0) were added and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (260 ml) to obtain the compound 100 (10.92 g, yield: 86%).

MS [M + H] < ⁺ > = 803

< Manufacturing example 1-6>

[Compound 121]

Compound A (10 g, 17.86 mmol) and 2-chloro-4-phenylquinazoline (4.71 g, 19.64 mmol) were dissolved in 280 ml of xylene in a 500 ml round bottom flask under nitrogen atmosphere and sodium tert-butoxide (2.23 g, 23.18 mmol) , And bis (tri- tert- butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added thereto, followed by heating and stirring for 12 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (340 ml) to obtain the compound 121 (12.55 g, yield: 91%).

MS [M + H] < ⁺ > = 765

< Manufacturing example 1-7>

[Compound 143]

(10 g, 17.86 mmol) and (4-bromophenyl) diphenylphosphine oxide (6.99 g, 19.64 mmol) were dissolved in 220 ml of xylene in a 500 ml round-bottomed flask under nitrogen atmosphere and sodium tert-butoxide (2.23 g, 23.18 mmol) , And Bis (tri- tert- butylphosphine) palladium (0) (0.09 g, 0.18 mmol) was added thereto, followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (310 ml) to obtain the compound 143 (8.25 g, yield: 72%).

MS [M + H] < ⁺ > = 837

<Experimental Example 1-1>

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, the compound 1 was vacuum deposited on the hole transport layer to a thickness of 100 Å to form an electron blocking layer.

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 a vapor deposition rate of 0.4 to 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 < ^-6 > torr, thereby fabricating an organic light emitting device.

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

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 21 was used instead of Compound 1 in Experimental Example 1-1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 100 was used instead of Compound 1 in Experimental Example 1-1.

&Lt; Comparative Example 1-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound EB1 was used instead of Compound 1 in Experimental Example 1-1.

[EB1]

&Lt; Comparative Example 1-2 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the following compound EB2 was used in place of Compound 1 in Experimental Example 1-1.

[EB2]

The results shown in Table 1 were obtained when current was applied to the organic light-emitting devices fabricated by Examples 1-1 to 1-4 and Comparative Examples 1-1 and 1-2.

compound
(Electron blocking layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1-1 Compound 1 3.54 6.53 (0.138, 0.128) Experimental Example 1-2 Compound 2 3.60 6.42 (0.137, 0.126) Experimental Example 1-3 Compound 21 3.68 6.39 (0.137, 0.126) Experimental Examples 1-4 Compound 100 3.78 6.18 (0.137, 0.126) Comparative Example 1-1 EB1 4.64 5.35 (0.136, 0.127) Comparative Example 1-2 EB2 4.88 5.21 (0.135, 0.127)

As shown in Table 1, in the case of the organic light emitting device manufactured using the heterocyclic compound according to one embodiment of the present invention as the electron blocking layer, And exhibits excellent characteristics in terms of stability.

In addition, the organic luminescent devices of Experimental Examples 1-1 to 1-4 were superior in the efficiency, driving voltage, and driving voltage of the organic light emitting device to those of Comparative Examples 1-1 and 1-2 in which the terphenyl group or biphenyl group was substituted with indolocarbazole And / or exhibits excellent properties in terms of stability.

As shown in Table 1, it was confirmed that the compounds of the present invention are excellent in electron blocking ability and applicable to organic light emitting devices.

&Lt; Comparative Example 2-1 >

The compounds prepared in Preparation Examples were subjected to high purity sublimation purification by a conventionally known method, and then a green organic light emitting device was prepared in the following manner.

The glass substrate coated with ITO (ndium tin oxide) 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.

(60 nm) / TCTA (80 nm) / CBP + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) using CBP as a host on the prepared ITO transparent electrode. ) / LiF (1 nm) / Al (200 nm) were fabricated in this order to fabricate an organic light emitting device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP are as follows.

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1 except that the compound 68 was used instead of CBP in the above Comparative Example 2-1.

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 121 was used instead of Compound CBP in Comparative Example 2-1.

&Lt; Comparative Example 2-2 &

An organic light emitting device was prepared in the same manner as in Comparative Example 2-1, except that the following compound GH1 was used in place of the compound CBP in Comparative Example 2-1.

[GH1]

&Lt; Comparative Example 2-3 >

An organic light emitting device was prepared in the same manner as in Comparative Example 2-1, except that the following compound GH2 was used instead of the compound CBP in Comparative Example 2-1.

[GH2]

When current was applied to the organic light-emitting devices fabricated in Experimental Examples 2-1 and 2-2 and Comparative Examples 2-1 to 2-3, the results shown in Table 2 were obtained.

compound
(Host) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Emission peak
(nm) Comparative Example 2-1 CBP 6.82 35.12 516 Experimental Example 2-1 Compound 68 5.51 48.93 517 EXPERIMENTAL EXAMPLE 2-2 Compound 121 5.82 42.24 516 Comparative Example 2-2 GH1 6.47 38.2 518 Comparative Example 2-3 GH2 6.72 36.75 517

As shown in Table 2, the green organic light emitting devices of Experimental Examples 2-1 and 2-2 using the compound according to one embodiment of the present invention as the host material of the light emitting layer were comparative examples 2-1 Which is superior to the green organic light emitting device of the present invention in terms of current efficiency and driving voltage.

In addition, the organic light emitting devices of Experimental Examples 2-1 and 2-2 were superior in efficiency, driving voltage and / or driving voltage of organic light emitting devices to those of Comparative Examples 2-2 and 2-3 in which a terphenyl group or a biphenyl group was substituted with indorocarbazole, Or exhibit excellent properties in terms of stability.

Although the preferred embodiments of the present invention (the electron blocking layer and the green light emitting layer) have been described above, the present invention is not limited thereto, but can be modified in various ways within the scope of the claims and the detailed description of the invention And this also belongs to the category of invention.

10, 11: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: Hole injection layer
70: hole transport layer
80: electron blocking layer
90: electron transport layer
100: electron injection layer

Claims

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

In Formula 1,
Y is a dibenzofuranyl group, or a phenyl group substituted or unsubstituted with a diphenylphosphine oxide group; A biphenyl group; A fluorenyl group substituted with an alkyl group; A triazinyl group substituted with a phenyl group; And a quinazolinyl group substituted with a phenyl group.

delete

The heterocyclic compound according to claim 1, wherein Y is selected from any one of substituents of the following [A-3] to [A-5]:
[A-3]

[A-4]

[A-5]

The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Formula 1 is represented by any one of the following compounds 1, 2, 21, 23, 24, 26 to 28, 68, 100, 101, :

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 contains the heterocyclic compound of any one of claims 1, 4 and 5 .

7. The organic light emitting device according to claim 6, wherein the organic layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.

7. The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound.

7. The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a phosphorescent host of the light emitting layer.

7. The organic electroluminescent device according to claim 6, wherein the organic material layer comprises an electron transporting layer, an electron injecting layer, or a layer simultaneously carrying out electron transporting and electron injection, wherein the electron transporting layer, And an organic light emitting layer.

[7] The organic light emitting device according to claim 6, wherein the organic material layer further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.