KR101944005B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

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]

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

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 may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection 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.

U.S. Patent Application Publication No. 2004-0251816

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 and R 2 are the same or different and are each independently a substituted or unsubstituted alkyl group,

R3 to R5 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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; Or a substituted or unsubstituted heteroaryl group,

L1 is a direct bond; A substituted or unsubstituted monocyclic or bicyclic arylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted phenylenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted arylene group having four or more rings; Or a substituted or unsubstituted heteroarylene group,

Ar1 is a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r3 is an integer of 1 to 4,

r4 is 1 or 2,

r5 is an integer of 1 to 3,

When there are a plurality of r3 to r5, respectively, the structures in the plurality of parentheses are equal to 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 comprises a heterocyclic compound represented by Formula 1, to provide.

The heterocyclic compound according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device and by using it, it is possible to improve the efficiency, the driving voltage and / or the lifetime characteristics of the organic light emitting device.

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 heterocyclic 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.

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; A nitrile group; 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.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.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, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is 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 methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine 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; And an N-biphenylfluorenylamine group, but are not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of 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-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine 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 , wherein R ₁₀₀ and R ₁₀₁ 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, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

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 a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, no.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

,

,

및

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

,

,

,

,

And

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

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.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide 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 at least two aryl groups may contain 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 heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofuranyl groups.

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 having 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 may be selected from the examples of the above-mentioned heteroaryl 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.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

In the present specification, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.

In this specification, the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. 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 heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the heteroaryl group or the heterocyclic group except that the monocyclic group is not monovalent.

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (2) to (5).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

The definitions of R1 to R5, r3 to r5, L1 and Ar1 are the same as those in the above formula (1).

According to one embodiment of the present invention, in the general formula (1), R 1 and R 2 are the same or different and each independently an alkyl group.

According to one embodiment of the present invention, in the general formula (1), R 1 and R 2 are the same or different and are each independently a methyl group.

According to one embodiment of the present invention, the formula (1) is represented by the following formula (6).

[Chemical Formula 6]

In Formula 6,

The definition of L1 and Ar1 is the same as that of the above formula (1).

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (7) to (10).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the above formulas (7) to (10)

The definition of L1 and Ar1 is the same as that of the above formula (1).

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A monocyclic or bicyclic arylene group; Phenanthrenylene group; A phenylenylene group; A fluorenylene group; An arylene group having four or more rings; Or a heteroarylene group.

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted quaterphenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted pyrenylene group; A substituted or unsubstituted triphenylene group; Substituted or unsubstituted carbazolylene group.

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A phenylene group; Biphenyllylene groups; Naphthylene group; A terphenylene group; A quaterphenylene group; A fluorenylene group; Phenanthrenylene group; Pyrenylene group; Triphenylenylene group; Or a carbazolylene group.

According to one embodiment of the present invention, L1 in the formula (1) may be any one of the following structures, but is not limited thereto.

According to one embodiment of the present invention, in Formula 1, L1 is a direct bond; A phenylene group; Or a carbazolylene group.

According to one embodiment of the present invention, in the general formula (1), Ar1 represents a substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl group.

; 치환 또는 비치환된

; 및 하기 화학식 a로 표시되는 구조로 이루어진 군으로부터 선택되며, According to one embodiment of the present invention, Ar 1 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 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 bonded to the formula (1) through the above-mentioned L1.

(A)

In the above formula (a)

Any one of X1 to X12 is a moiety bonded to the formula (1) via the above-mentioned L1, and the remaining ones are the same or different, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are connected to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, in the formula (a), any one of X1 to X12 is a site bonded to the formula (1) through the L1, and the rest is hydrogen.

According to one embodiment of the present invention, in the formula (a), X11 and X12 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 the formula (a), X11 and X12 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 specification, in the above formula (a), X11 and X12 are connected to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present specification, in the above formula (a), X11 and X12 are connected to each other to form a benzene ring.

;

;

;

;

;

;

;

;

;

;

;

;

; 및

로 이루어진 군으로부터 선택되며,According to one embodiment of the present invention, Ar 1 represents 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; Benzocarbazolyl group; A dibenzocarbazolyl group; A carbazolyl group;

;

;

;

;

;

;

;

;

;

;

;

;

; And

, ≪ / RTI >

로 이루어진 군으로부터 선택되는 1 이상으로 치환 또는 비치환될 수 있다.Ar1 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; And

≪ RTI ID = 0.0 > and / or < / RTI >

The above-mentioned moiety means a moiety bonded to the formula (1) through the above-mentioned L1.

According to one embodiment of the present invention, Ar 1 in the formula (1) is represented by any one of the following structural formulas [A-1] to [A-4].

[A-1]

[A-2]

[A-3]

[A-4]

In the above formula, --- denotes a moiety bonded to the formula (1) through the L1.

According to one embodiment of the present invention, in Formula 1, Ar1 represents a phosphine oxide group substituted with an aryl group; An aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group or a heteroaryl group which is substituted or unsubstituted with an alkyl group.

According to one embodiment of the present invention, in Formula 1, Ar1 represents a phosphine oxide group substituted with an aryl group; A phenyl group; Naphthyl group; A fluorenyl group substituted with an alkyl group; A pyridyl group substituted or unsubstituted with an aryl group; A pyrimidyl group substituted or unsubstituted with an aryl group; A triazinyl group substituted or unsubstituted with an alkyl group or an aryl group or a heteroaryl group; A dibenzofuranyl group; A dibenzothiophene group; A quinazolyl group substituted or unsubstituted with an aryl group; Benzocarbazolyl group; A carbazolyl group substituted or unsubstituted with an aryl group; A triphenylrenyl group; A phenanthrenyl group; Or a benzimidazolyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar 1 represents a phosphine oxide group substituted with a phenyl group; A phenyl group; Naphthyl group; A fluorenyl group substituted with a methyl group; A pyridyl group substituted or unsubstituted with a phenyl group; A pyrimidyl group substituted or unsubstituted with at least one element selected from the group consisting of a phenyl group and a biphenyl group; A substituted or unsubstituted triazinyl group selected from the group consisting of a phenyl group, a biphenyl group, a fluorenyl group substituted with a methyl group, a dibenzofuranyl group, and a dibenzothiophene group; A dibenzofuranyl group; A dibenzothiophene group; A quinazolyl group substituted or unsubstituted with a biphenyl group or a naphthyl group; Benzocarbazolyl group; A carbazolyl group substituted or unsubstituted with a phenyl group, a biphenyl group or a naphthyl group; A triphenylrenyl group; A phenanthrenyl group; Or a benzimidazolyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, the formula (1) is any one selected from the following compounds.

According to one embodiment of the present invention, the core structure of the heterocyclic compound represented by Formula 1 may be prepared by the following Formula 1, but is not limited thereto.

[Formula 1]

In the general formula (1), L1 and Ar1 have the same definitions as in the general formula (1).

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 the above-described heterocyclic compound.

According to one embodiment of the present disclosure, the organic material layer of the organic light emitting 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 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 organic layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more 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 injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90 and a second electrode 50) are successively laminated on a substrate. 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 material layer includes a hole transporting layer, and the hole transporting layer includes the heterocyclic compound represented by the general formula (1).

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 material layer includes an electron transporting layer, and the electron transporting layer includes a heterocyclic compound represented by the general 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 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) as a host of the light emitting layer.

In one embodiment of the present invention, the organic material layer includes the heterocyclic compound represented by Formula 1 as a host, and may include other organic compound, metal or metal compound as a dopant.

The dopant may be at least one selected from the following compounds, but is not limited thereto.

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 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; Benzoxazole, benzothiazole and benzimidazole compounds; 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 an 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 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 an 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.

Compounds A to H were prepared according to Reaction Scheme 1 below.

[Reaction Scheme 1]

PREPARATION EXAMPLE 1 Preparation of Compound 1

Compound E (12.13 g, 29.60 mmol) and 3-bromo-9-phenyl-9H-carbazole (10.0 g, 31.15 mmol) were dissolved in 240 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, 120 mg) was added, tetrakis- (triphenylphosphine) palladium (0.65 g, 0.59 mmol) was added, and the mixture was heated with stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (170 ml) to give Compound 1 (16.66 g, 82%).

MS [M + H] < ⁺ > = 526

PREPARATION EXAMPLE 2 Preparation of Compound 2

Compound E (15.90 g, 38.78 mmol) and 2-bromodibenzo [b, d] furan (10.0 g, 40.80 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask under a nitrogen atmosphere, and 2M potassium carbonate aqueous solution (100 ml) And tetrakis- (triphenylphosphine) palladium (0.75 g, 0.67 mmol) was added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (150 ml) to give Compound 2 (19.45 g, 83%).

MS [M + H] < ⁺ > = 451

PREPARATION EXAMPLE 3 Preparation of Compound 3

Compound E (14.59 g, 35.58 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 37.45 mmol) were completely dissolved in 300 ml of tetrahydrofuran in a 500 ml round- Then, 2M aqueous potassium carbonate solution (150 ml) was added, tetrakis- (triphenylphosphine) palladium (0.87 g, 0.75 mmol) was added, and the mixture was heated with stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (340 ml) to obtain Compound 3 (19.45 g, 83%).

MS [M + H] < ⁺ > = 516

Preparation Example 4 Preparation of Compound 4

Compound E (11.36 g, 27.70 mmol), 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (10.0 g, 29.15 mmol) was dissolved in 360 ml of tetrahydrofuran. To the mixture was added 2M potassium carbonate aqueous solution (180 ml), tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) Followed by heating and stirring. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (340 ml) to obtain Compound 4 (14.58 g, 84%).

MS [M + H] < ⁺ > = 592

PREPARATION EXAMPLE 5 Preparation of Compound 5

(10.06 g, 24.55 mmol) and 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.0 g, 25.84 mmol) were added to a 500 ml round-bottomed flask under nitrogen atmosphere in tetrahydrofuran And then 2M potassium carbonate aqueous solution (200 ml) was added thereto. Tetrakis- (triphenylphosphine) palladium (0.91 g, 0.79 mmol) was added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 190 ml of tetrahydrofuran to obtain Compound 5 (13.47 g, 87%).

MS [M + H] < ⁺ > = 592

PREPARATION EXAMPLE 6 Preparation of Compound 6

(10.06 g, 24.55 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.0 g, 25.84 mmol) were added to a 500 ml round-bottomed flask under nitrogen atmosphere in tetrahydrofuran And then 2M potassium carbonate aqueous solution (200 ml) was added thereto. Tetrakis- (triphenylphosphine) palladium (0.91 g, 0.79 mmol) was added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 190 ml of tetrahydrofuran to obtain Compound 6 (11.08 g, 72%).

MS [M + H] < ⁺ > = 592

PREPARATION EXAMPLE 7 Preparation of Compound 7

Compound E (16.23 g, 39.58 mmol) and 2-chloro-4-phenylquinazoline (10.0 g, 41.67 mmol) were completely dissolved in 220 ml of tetrahydrofuran in a 500 ml round bottom flask under a nitrogen atmosphere and 2M potassium carbonate aqueous solution (110 ml) And tetrakis- (triphenylphosphine) palladium (0.96 g, 0.83 mmol) was added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 230 ml of tetrahydrofuran to obtain Compound 7 (21.45 g, 67%).

MS [M + H] < ⁺ > = 489

PREPARATION EXAMPLE 8 Preparation of Compound 8

Compound (10.06 g, 24.55 mmol) and 4- (3-bromophenyl) -2,6-diphenylpyrimidine (10.0 g, 25.84 mmol) were completely dissolved in 400 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, Aqueous solution (200 ml) was added, tetrakis- (triphenylphosphine) palladium (0.91 g, 0.79 mmol) was added, and the mixture was heated with stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 120 ml of tetrahydrofuran to obtain Compound 8 (9.75 g, 65%).

MS [M + H] < ⁺ > = 591

PREPARATION EXAMPLE 9 Preparation of Compound 9

Compound E (12.13 g, 29.60 mmol) and 9- (4-bromophenyl) -9H-carbazole (10.0 g, 31.15 mmol) were completely dissolved in 300 ml of tetrahydrofuran in a 500 ml round bottom flask under nitrogen atmosphere, 150 ml) was added, and tetrakis- (triphenylphosphine) palladium (0.72 g, 0.62 mmol) was added thereto, followed by heating and stirring for 2 hours. The mixture was cooled to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (220 ml) to obtain Compound 9 (12.11 g, 74%).

MS [M + H] < ⁺ > = 526

PREPARATION EXAMPLE 10 Preparation of Compound 10

Compound E (8.18 g, 19.96 mmol), 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole , 21.01 mmol) was completely dissolved in 480 ml of tetrahydrofuran, and 2M potassium carbonate aqueous solution (240 ml) was added. Tetrakis- (triphenylphosphine) palladium (0.49 g, 0.42 mmol) was added and the mixture was heated with stirring for 9 hours . The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 310 ml of tetrahydrofuran to obtain 10 (10.39 g, 73%).

MS [M + H] < ⁺ > = 681

PREPARATION EXAMPLE 11 Preparation of Compound 11

Compound E (10.94 g, 26.69 mmol) and (4-bromophenyl) diphenylphosphine oxide (10.0 g, 28.09 mmol) were completely dissolved in 300 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere and 2M potassium carbonate aqueous solution (150 ml) And tetrakis- (triphenylphosphine) palladium (0.72 g, 0.62 mmol) were added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 ml of ethyl acetate to obtain Compound 11 (12.11 g, 74%).

MS [M + H] < ⁺ > = 561

PREPARATION EXAMPLE 12 Preparation of Compound 12

(10.0 g, 28.74 mmol) was dissolved in 260 ml of tetrahydrofuran in a 500 ml round-bottomed flask under a nitrogen atmosphere, to a solution of compound E (11.19 g, 27.30 mmol) and 2- (4-bromophenyl) After completely dissolved, 2M aqueous potassium carbonate solution (130 ml) was added, tetrakis- (triphenylphosphine) palladium (0.66 g, 0.57 mmol) was added, and the mixture was heated with stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (260 ml) to prepare Compound 12 (8.95 g, 56%).

MS [M + H] < ⁺ > = 553

≪ Preparation Examples 13 to 18 > Preparation of compounds 13 to 18

The following compounds 13 to 18 were prepared in the same manner as in Preparation Examples 3 to 8, except that Compound F was used instead of Compound E as a starting material.

≪ Preparation Examples 19 to 24 > Preparation of compounds 19 to 24

The following compounds 19 to 24 were prepared in the same manner as in Preparation Examples 3 to 8, except that Compound G was used instead of Compound E as a starting material.

≪ Preparation Examples 25 to 30 > Preparation of compounds 25 to 30

The following compounds 25 to 30 were prepared in the same manner as in Preparation Examples 3 to 8, except that Compound H was used instead of Compound E as a starting material.

<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.

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.

Subsequently, the following compound 1 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM 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.

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 1-2>

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.

&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.

&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.

The results shown in Table 1 were obtained when a current was applied to the organic light-emitting devices fabricated in Experimental Examples 1-1, 1-2 and 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 3.75 6.47 (0.137, 0.126) Experimental Example 1-2 Compound 2 3.86 6.35 (0.137, 0.127) Comparative Example 1-1 EB1 4.15 5.86 (0.136, 0.127) Comparative Example 1-2 EB2 4.37 5.62 (0.136, 0.127)

As shown in Table 1, the organic light emitting device manufactured using the compound of the present invention as an electron blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

The compound of Comparative Example 1-1 and Comparative Example 1-2 in which a ring was formed in a structure similar to the core of the heterocyclic compound of Formula 1 according to an embodiment of the present invention was used as an electron blocking layer, Lower voltage, and higher efficiency.

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) / Alq3 (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 produce an organic light emitting device.

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

<Experimental Example 2-1>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 3 was used instead of CBP in Comparative Example 2-1.

 <Experimental Example 2-2>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 4 was used instead of Compound CBP in Experimental Example 2.

<Experimental Example 2-3>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 5 was used instead of Compound CBP in Comparative Example 2-1.

<Experimental Example 2-4>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 6 was used instead of Compound CBP in Comparative Example 2-1.

<Experimental Example 2-5>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 7 was used instead of Compound CBP in Comparative Example 2-1.

<Experimental Example 2-6>

An organic light emitting device was prepared in the same manner as in Comparative Example 2-1, except that Compound 8 was used instead of Compound CBP in Comparative Example 2-1.

<Experimental Example 2-7>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 14 was used instead of Compound CBP in Comparative Example 2-1.

<Experimental Example 2-8>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1 except that Compound 16 was used instead of Compound CBP in Comparative Example 2-1.

&Lt; Experimental Example 2-9 >

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 20 was used instead of Compound CBP in Comparative Example 2-1.

<Experimental Example 2-10>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1 except that the compound 22 was used instead of the compound CBP in the above Comparative Example 2-1.

<Experimental Example 2-11>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 26 was used instead of Compound CBP in Comparative Example 2-1.

<Experimental Example 2-12>

An organic light emitting device was fabricated in the same manner as in Comparative Example 2-1, except that Compound 28 was used instead of Compound CBP in Comparative Example 2-1.

&Lt; Comparative Example 2-2 &

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

&Lt; Comparative Example 2-3 >

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

When current was applied to the organic light-emitting devices manufactured in Experimental Examples 2-1 to 2-12 and Comparative Examples 2-1 to 2-3, the results shown in Table 2 below were obtained.

compound
(Host) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) EL peak
(nm) Comparative Example 2-1 CBP 7.62 35.32 516 Experimental Example 2-1 Compound 3 6.70 44.73 517 EXPERIMENTAL EXAMPLE 2-2 Compound 4 6.66 44.85 516 Experimental Example 2-3 Compound 5 6.71 44.72 517 Experimental Example 2-4 Compound 6 6.69 44.75 518 Experimental Example 2-5 Compound 7 6.85 44.31 517 Experimental Examples 2-6 Compound 8 6.63 44.63 517 Experimental Example 2-7 Compound 14 6.64 44.60 516 Experimental Examples 2-8 Compound 16 6.62 44.66 517 Experimental Examples 2-9 Compound 20 6.68 44.558 517 Experimental Example 2-10 Compound 22 6.67 44.59 517 Experimental Example 2-11 Compound 26 6.66 44.60 517 Experimental Examples 2-12 Compound 28 6.69 44.62 517 Comparative Example 2-2 GH 1 7.25 39.52 517 Comparative Example 2-3 GH 2 7.56 37.41 516

As shown in Table 2, the green organic light emitting devices of Experimental Examples 2-1 to 2-12 using the heterocyclic compound represented by Chemical Formula 1 according to an embodiment of the present invention as a host material of the light emitting layer, It was confirmed that the organic EL device of Comparative Example 2-2 and Comparative Example 2-2 having a structure similar to that of the comparative example 2-1 and the core of the present invention had excellent performance in terms of current efficiency and driving voltage I could. Particularly, it can be seen that the above compounds having triazines and pyrimidines as substituents as substituents are suitable as green light emitting organic devices

<Experimental Examples 3-1 to 3-4>

The compounds prepared in Preparation Examples were subjected to high purity sublimation purification by a conventionally known method, and red organic light emitting devices were prepared as follows.

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the base pressure was adjusted to 1 x 10 &lt; ^-6 &gt; torr. Then, an organic material was injected onto the ITO using DNTPD (700 ANGSTROM), alpha -NPB (300 ANGSTROM) , as a 23 or 29, the host (90 wt%) used, and to (piq) ₂ Ir (acac) co-deposited (300 Å) to (10 wt%) as a _{dopant, Alq 3 (350 Å),} LiF ( 5 Å), and Al (1,000 Å) in this order and measured at 0.4 mA.

The DNTPD, α-NPB, (piq ) 2 Ir (acac) , and structure of Alq ₃ is as follows.

&Lt; Comparative Example 3-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound CBP was used instead of Compound 7 in Experimental Example 3-1.

The voltage, the current density, the luminance, the color coordinates, and the lifetime were measured for the organic light-emitting devices manufactured in Experimental Examples 3-1 to 3-4 and Comparative Example 3-1, and the results are shown in Table 3 below. T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

division Host Dopant Voltage
(V) Luminance
(cd / m &lt; 2 & CIEx, CIEy T95 (hr) Experimental Example 3-1 Compound 7 [(piq) 2Ir (acac)] 4.4 1860 0.673, 0.366 395 Experimental Example 3-2 Compound 17 [(piq) 2Ir (acac)] 4.7 1780 0.674, 0.325 390 Experimental Example 3-3 Compound 23 [(piq) 2Ir (acac)] 4.3 1910 0.673, 0.366 425 Experimental Example 3-4 Compound 29 [(piq) 2Ir (acac)] 4.5 1840 0.674, 0.325 385 Comparative Example 3-1 CBP [(piq) 2Ir (acac)] 5.7 1420 0.670, 0.331 350

Experimental results show that the red organic light emitting devices of Experimental Examples 3-1 to 3-4 according to one embodiment of the present invention are superior to the red organic light emitting devices of Comparative Example 3-1 using the conventional compound CBP in current efficiency, And it is confirmed that it shows excellent performance in terms of surface area. Particularly, it can be seen that the above compounds having triazines and quinazolines as substituents as substituents are suitable as red light emitting organic devices.

<Experimental Example 4-1>

In Experimental Example 1-1, the same experiment was conducted except that Compound 3 was used instead of ET1 as the electron transporting layer.

<Experimental Example 4-2>

In Experimental Example 1-1, the same experiment was conducted except that Compound 4 was used instead of ET1 as the electron transport layer.

<Experimental Example 4-3>

The same experiment was conducted except that Compound 5 was used instead of ET1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 4-4>

In Experimental Example 1-1, the same experiment was conducted except that Compound 6 was used instead of ET1 as the electron transporting layer.

<Experimental Example 4-5>

The same experiment was conducted except that Compound 8 was used instead of ET1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 4-6>

The same experiment was conducted except that Compound 13 was used instead of ET1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 4-7>

The same experiment was conducted except that Compound 14 was used instead of ET1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 4-8>

In Experimental Example 1-1, the same experiment was conducted except that Compound 15 was used instead of ET1 as the electron transporting layer.

<Experimental Example 4-9>

In Experimental Example 1-1, the same experiment was conducted except that Compound 16 was used instead of ET1 as the electron transporting layer.

<Experimental Example 4-10>

In Experimental Example 1-1, the same experiment was conducted except that Compound 18 was used instead of ET1 as the electron transporting layer.

<Experimental Example 4-11>

In Experimental Example 1-1, the same experiment was conducted except that Compound 19 was used instead of ET1 as the electron transport layer.

<Experimental Example 4-12>

In Experimental Example 1-1, the same experiment was conducted except that Compound 20 was used instead of ET1 as the electron transport layer.

<Experimental Example 4-13>

In Experimental Example 1-1, the same experiment was conducted except that Compound 21 was used instead of ET1 as the electron transport layer.

<Experimental Example 4-14>

In Experimental Example 1-1, the same experiment was conducted except that Compound 22 was used instead of ET1 as the electron transporting layer.

<Experimental Example 4-15>

The same experiment was conducted except that Compound 25 was used instead of ET1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 4-16>

In Experimental Example 1-1, the same experiment was conducted except that Compound 26 was used instead of ET1 as the electron transporting layer.

<Experimental Example 4-17>

The same experiment was conducted except that Compound 27 was used instead of ET1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 4-18>

In Experimental Example 1-1, the same experiment was conducted except that Compound 28 was used instead of ET1 as the electron transporting layer.

&Lt; Comparative Example 4-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that the following compound ET2 was used instead of Compound 3 as the electron transporting layer.

&Lt; Comparative Example 4-2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 4-1, except that the following compound ET3 was used instead of Compound 3 as the electron transporting layer.

When the current was applied to the organic light-emitting devices manufactured in Experimental Examples 4-1 to 2-18 and Comparative Examples 4-1 and 4-2, the results shown in Table 4 were obtained.

compound Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 4-1 Compound 3 3.78 4.91 (0.138, 0.126) Experimental Example 4-2 Compound 4 3.55 4.95 (0.139, 0.127) Experimental Example 4-3 Compound 5 3.66 4.85 (0.138, 0.126) Experimental Example 4-4 Compound 6 3.65 4.82 (0.138, 0.127) Experimental Example 4-5 Compound 8 3.69 4.65 (0.137, 0.129) Experimental Examples 4-6 Compound 13 3.75 4.64 (0.138, 0.128) Experimental Examples 4-7 Compound 14 3.70 4.72 (0.138, 0.129) Experimental Examples 4-8 Compound 15 3.76 4.65 (0.136, 0.128) Experimental Examples 4-9 Compound 16 3.78 4.69 (0.137, 0.127) Experimental Examples 4-10 Compound 18 3.75 4.65 (0.137, 0.127) Experimental Example 4-11 Compound 19 3.79 4.66 (0.138, 0.127) Experimental Examples 4-12 Compound 20 3.77 4.67 (0.137, 0.126) Experimental Example 4-13 Compound 21 3.73 4.52 (0.137, 0.128) Experimental Example 4-14 Compound 22 3.78 4.71 (0.137, 0.127) Experimental Example 4-15 Compound 25 3.77 4.73 (0.137, 0.128) Experimental Examples 4-16 Compound 26 3.76 4.72 (0.138, 0.127) Experimental Example 4-17 Compound 27 3.75 4.70 (0.137, 0.127) Experimental Example 4-18 Compound 28 3.79 4.72 (0.137, 0.127) Comparative Example 4-1 ET2 4.15 4.25 (0.136, 0.130) Comparative Example 4-2 ET3 4.37 4.07 (0.136, 0.129)

As a result of the experiment, the organic light emitting devices of Experimental Examples 4-1 to 4-18 according to one embodiment of the present invention had the same structure as the core of the present invention, It was confirmed that the current efficiency and the driving voltage were superior to those of the device.

Although the preferred embodiments of the present invention (electron blocking layer, green light emitting layer, red light emitting layer, electron transporting layer) have been described above, the present invention is not limited thereto. It is possible to carry out the modification, and this is also within the scope of the 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 transport layer
90: electron injection layer

Claims (3)

A first electrode;
A second electrode facing the first electrode; And
And at least one organic compound layer disposed between the first electrode and the second electrode,
Wherein the organic material layer comprises a light emitting layer and the light emitting layer contains a heterocyclic compound represented by the following formula (1) as another organic compound, metal or metal compound as a dopant and a host:
[Chemical Formula 1]

In Formula 1,
R1 and R2 are methyl groups,
R3 to R5 are hydrogen,
L1 is a direct bond, a phenylene group, or a carbazolylene group,
Ar1 represents a substituted or unsubstituted carbazole group substituted with a phenyl group, a triazine group substituted or unsubstituted with a phenyl group or a biphenyl group, a quinazoline group substituted or unsubstituted with a phenyl group, a pyrimidine group substituted or unsubstituted with a phenyl group, Or a benzimidazole group unsubstituted or substituted with a pyridine group, a diphenylphosphine oxide group, or a phenyl group,
r3 is an integer of 1 to 4,
r4 is 1 or 2,
r5 is an integer of 1 to 3; The organic electroluminescent device according to claim 1, wherein the formula (1) is represented by any one of the following formulas (2) to (5)
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
The definitions of R1 to R5, r3 to r5, L1 and Ar1 are the same as those in the above formula (1). The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

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