KR101821521B1 - Fused cyclic compound including nitrogen and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a nitrogen-containing condensed ring compound and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrogen-containing condensed ring compound and an organic light-

The present application claims the benefit of Korean Patent Application No. 10-2016-0012936 filed on February 2, 2016, the entire contents of which are incorporated herein by reference.

The present invention relates to a nitrogen-containing condensed ring compound and an organic light emitting device using the same.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows.

When an organic layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

Therefore, there is a need in the art to develop new organic materials.

Korean Patent Publication No. 2000-0051826

The present invention provides a nitrogen-containing condensed ring compound and an organic light emitting device using the same.

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

[Chemical Formula 1]

In Formula 1,

R1 to R17 and Ar1 are hydrogen, or adjacent substituents may be bonded to each other to form a ring,

Ar2 is 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, or is bonded to adjacent substituents to form a ring,

a is 2,

L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group, and L1 may combine with R16 to form a ring.

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 compound described above.

The compound according to one embodiment of the present disclosure 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 to 5 are cross-sectional views illustrating the structure of an organic light emitting device according to an embodiment of the present invention.
6 is a graph showing an LC / MS graph of Compound 1 synthesized from Synthesis Example 1. Fig.
7 is a graph showing an LC / MS graph of Compound 3 synthesized from Synthesis Example 3. Fig.
8 is a graph showing an LC / MS graph of Compound 6 synthesized from Synthesis Example 6. Fig.

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

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

According to one embodiment of the present invention, since the compound represented by Formula 1 has a core in which indole is condensed in a spiro structure containing nitrogen, high thermal resistance of the organic light emitting device can be achieved by the structural characteristic of the spiro structure , And when applied to an organic material layer of an organic light emitting device, there is an effect of high luminous efficiency, low driving voltage, and long life.

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; 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-arylalkylamine 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- , A diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, and a triphenylamine group, but are 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-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, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to 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.

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, the heterocyclic group 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 above heteroaryl groups.

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, the ring may be a hydrocarbon ring or a heterocycle, but is not limited thereto.

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 aromatic, aliphatic or aromatic and aliphatic condensed rings, and may be selected from the examples of the heteroaryl group except that it is not monovalent.

According to one embodiment of the present invention, the compound represented by Formula 1 is represented by Formula 2 or 3 below.

(2)

(3)

In the general formula (2) or (3)

The definitions of R1 to R17, Ar1, Ar2, a and L2 are the same as those of the above formula (1)

R18 is hydrogen or combines with adjacent substituents to form a ring, b = 4, and c = 3.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

In Formulas 1-1 to 1-6,

The definitions of R1 to R17, Ar1, Ar2, a, L1 and L2 are the same as those of the above formula (1).

According to one embodiment of the present invention, the compound represented by Formula 1 is represented by any one of the following Formulas 2-1 to 2-6.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

In the general formulas (2-1) to (2-6)

The definitions of R1 to R17, Ar1, Ar2, a and L2 are the same as those of the above formula (1)

R18 is hydrogen or combines with adjacent substituents to form a ring; b is 4;

According to one embodiment of the present invention, the compound represented by the formula (1) is represented by any one of the following formulas (3-1) to (3-6).

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

[Chemical Formula 3-6]

In the above formulas (3-1) to (3-6)

The definitions of R1 to R17, Ar1, Ar2, a and L2 are the same as those of the above formula (1)

R18 is hydrogen or combines with adjacent substituents to form a ring, and c is 3;

According to one embodiment of the present invention, L 1 and L 2 in the general formula (1) are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, L 1 and L 2 in the general formula (1) are the same or different and are each independently a direct bond; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, L 1 and L 2 in the general formula (1) are the same or different and are each independently a direct bond; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, L 1 and L 2 in the general formula (1) are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

According to one embodiment of the present invention, L 1 and L 2 in the general formula (1) are the same or different and are each independently a direct bond; A phenylene group; Or a naphthylene group.

According to one embodiment of the present invention, in the general formula (1), Ar2 represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in Formula 1, Ar2 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, Ar 2 in the general formula (1) is an aryl group which is the same as or different from each other and is independently substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in the general formula (1), Ar2 is an aryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, in the general formula (1), Ar2 represents a phenyl group substituted or unsubstituted with a phenyl group; Or a biphenyl group.

According to one embodiment of the present invention, in the above formula (1), Ar2 is a group represented by the following formula (A) or (B).

(A)

In formula (A)

Y1 to Y3 are the same or different and are each independently N or CRd,

One of R201, R220 and Rd is a moiety bonded to the formula (1) through L1 or L2 in the above formula (1), and the others are the same or different, 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, or is bonded to adjacent substituents to form a ring,

[Chemical Formula B]

In formula (B)

G ₁ is O, S, NR ₄₀₁ , or CR ₄₁₀ R ₄₁₁ ,

And U ₁ is N or CR _402, U ₂ is N or CR _403, U ₃ is N or CR _404, U ₄ is N or CR _405, U ₅ is N or CR _406, U ₆ is N or CR ₄₀₇ , U ₇ is N or CR ₄₀₈ , U ₈ is N or CR ₄₀₉ ,

When G ₁ is CR ₄₁₀ R ₄₁₁ , at least one of U ₁ to U ₈ is N,

Any one of R ₄₀₁ to R ₄₁₁ is a moiety bonded to the formula (1) via L 1 or L 2 in the formula (1), and the others are the same or different, and each independently hydrogen; heavy hydrogen; 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; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in formula (A), any one of R201, R220 and Rd is a moiety bound to formula (1) through L1 or L2 of formula (1), and the remaining is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in formula (A), any one of R201, R220 and Rd is a moiety bound to formula (1) through L1 or L2 of formula (1), and the remaining is hydrogen; An aryl group; Or a heteroaryl group.

According to one embodiment of the present invention, in formula (A), any one of R201, R220 and Rd is a moiety bound to formula (1) through L1 or L2 of formula (1), and the remaining is hydrogen; A phenyl group; A biphenyl group; Or a dibenzofurane group.

According to one embodiment of the present invention, the formula (A) is represented by the following formula (A-5).

[A-5]

In formula (A-5), Y1, Y2, and R220 are the same as defined in formula (A)

Z1 to Z4 are the same or different and are each independently N or CRg,

Rg 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, A-5 is represented by one of the following formulas A-6 to A-8.

[A-6]

[A-7]

[A-8]

In Formulas A-6 to A-8,

Y1, Y2, and R220 are as defined in Formula A above,

Q is a direct bond, C (= O), or CRhRi,

R202 to R205, Rh and Ri 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, the formula (A-5) is represented by one of the following formulas (A-9) to (A-13).

[A-9]

[A-10]

[A-11]

[A-12]

[A-13]

In Formulas A-9 to A-13,

One of R206, R207 and R220 is a moiety bonded to the formula (1) through L1 or L2 of the above formula (1), a group not bonded to L1 or L2 of the above formula (1), R202 To R205 and R221 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, or is bonded to adjacent substituents to form a ring,

r221 is an integer of 1 to 4,

When r221 is 2 or more, two or more R221 are the same or different from each other.

According to one embodiment of the present invention, any one of R206, R207 and R220 in the formulas A-9 to A-13 is a moiety bonded to the formula (1) through L1 or L2 of the formula (1) R207 and R220 do not bond with L1 or L2 of the above formula (1), R202 to R205 and R221 are hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, any one of R206, R207 and R220 in the formulas A-9 to A-13 is a moiety bonded to the formula (1) through L1 or L2 of the formula (1) R207 and R220 do not bond with L1 or L2 of the above formula (1), R202 to R205 and R221 are hydrogen; An aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, any one of R206, R207 and R220 in the formulas A-9 to A-13 is a moiety bonded to the formula (1) through L1 or L2 of the formula (1) R207 and R220 do not bond with L1 or L2 of the above formula (1), R202 to R205 and R221 are hydrogen; A phenyl group; A biphenyl group; Naphthyl group; Or a carbazolyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, the formula (B) is represented by any one of the following formulas (B-1) to (B-4).

[Formula B-1]

[Formula B-2]

[Formula B-3]

[Formula B-4]

In the above Formulas B-1 to B-4,

The definitions of U ₁ to U ₄ , R ₄₀₁ and R ₄₀₆ to R ₄₁₁ are the same as those of the above formula (B).

According to one embodiment of the present invention, the formula (B) is represented by any one of the following formulas (B-5) to (B-15).

[Formula B-5]

[Formula B-6]

[Formula B-7]

[Formula B-8]

[Chemical formula B-9]

[Chemical formula B-10]

[Formula B-11]

[Formula B-12]

[Formula B-13]

[Formula B-14]

[Formula B-15]

In the formulas (B-5) to (B-15), the definitions of R ₄₀₁ to R ₄₁₁ are the same as those of the formula (B).

According to one embodiment of the present invention, any one of R ₄₀₁ to R ₄₁₁ is a moiety bonded to Formula 1 via L 1 or L 2 in Formula 1, and the remaining moieties are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, any one of R ₄₀₁ to R ₄₁₁ is a moiety bonded to Formula 1 via L 1 or L 2 in Formula 1, and the remaining moieties are the same or different from each other, and each independently hydrogen; An alkyl group; Or an aryl group.

According to one embodiment of the present invention, any one of R ₄₀₁ to R ₄₁₁ is a moiety bonded to Formula 1 via L 1 or L 2 in Formula 1, and the remaining moieties are the same or different from each other, and each independently hydrogen; Methyl group; A phenyl group; A biphenyl group; Or a naphthyl group.

According to one embodiment of the present invention, in the general formula (1), Ar2 represents an aryl group substituted or unsubstituted with an aryl group; Or a heteroaryl group substituted with a heteroaryl group substituted with an aryl group; A heteroaryl group substituted by at least one member selected from the group consisting of an aryl group and a heteroaryl group; Or a group represented by the above formula (B).

According to one embodiment of the present invention, in the general formula (1), Ar2 represents a phenyl group substituted or unsubstituted with a phenyl group; A biphenyl group; A triazinyl group substituted by at least one member selected from the group consisting of a phenyl group, a biphenyl group, and a dibenzofurane group; A pyrimidyl group substituted by at least one member selected from the group consisting of a phenyl group and a biphenyl group; A phenyl group, a biphenyl group, a naphthyl group, a carbazolyl group substituted with a phenyl group, or a quinazolinyl group substituted with an unsubstituted carbazolyl group; A benzoquinazolinyl group substituted with a phenyl group; Or a group represented by the above formula (B).

According to one embodiment of the present invention, in Formula 1, L1 is a phenylene group.

According to one embodiment of the present invention, in Formula 1, L2 is a direct bond; A phenylene group; Or a naphthylene group.

According to one embodiment of the present invention, in the general formula (1), Ar1 is hydrogen.

According to one embodiment of the present invention, the formula (2-1) may be represented by any one of the following formulas, but is not limited thereto.

According to one embodiment of the present invention, the formula (2-2) is represented by any one of the following formulas, but is not limited thereto.

According to one embodiment of the present invention, Formula 2-3 is represented by one of the following formulas, but is not limited thereto.

According to one embodiment of the present invention, the above Formula 2-4 is represented by any one of the following formulas, but it is not limited thereto.

According to one embodiment of the present disclosure, Formula 2-5 is represented by any one of the following formulas, but is not limited thereto.

According to one embodiment of the present invention, the above Formula 2-6 is represented by any one of the following formulas, but it is not limited thereto.

According to one embodiment of the present invention, the formula (3-1) is represented by any one of the following formulas, but is not limited thereto.

According to one embodiment of the present invention, Formula (3-2) is represented by any one of the following formulas, but is not limited thereto.

According to one embodiment of the present invention, Formula 3-3 is represented by any one of the following formulas, but is not limited thereto.

According to one embodiment of the present disclosure, Formula 3-4 is represented by any one of the following formulas, but is not limited thereto.

According to one embodiment of the present invention, the above Formula 3-5 is represented by any one of the following formulas, but it is not limited thereto.

According to one embodiment of the present invention, Formula 3-6 is represented by any one of the following formulas, but is not limited thereto.

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 layer of the organic compound layer includes the compound represented by the general formula (1).

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 diode according to the present invention is illustrated in FIGS. 1 to 5, but the present invention is not limited thereto.

1 shows an organic light emitting device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially stacked on a substrate 1 Structure is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, the light emitting layer 5, or the electron transporting layer 6.

2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. In this structure, the compound represented by Formula 1 may be included in the hole injection layer 3, the hole transport layer 4, or the light emitting layer 5.

3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

4 shows a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

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

According to one embodiment of the present invention, the organic material layer further includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic material layer containing the compound represented by the formula .

According to one embodiment of the present invention, the organic compound layer containing the compound represented by Formula 1 includes the compound represented by Formula 1 as a host of the light emitting layer, and includes another organic compound, metal or metal compound as a dopant of the light emitting layer do.

According to one embodiment of the present disclosure, the dopant may be selected from the following structures, but is not limited thereto.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, that is, the 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 cathode material, an organic material layer, and a first electrode material on a substrate. The compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum evaporation 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.

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

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); A combination of a metal and an oxide such as ZnO: Al or SnO2: 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, LiO2 / Al, and Mg / Ag, but the present invention is 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 (Alq3); 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 Alq3; 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 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 more detail by way of examples. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

Manufacturing example

Production Example 1. Preparation of Core Structure of Formula 2-1

1) Synthesis of Compound A-1

(1.1 eq) of 1,3-dibromo-2-iodobenzene, 1.41 g (0.05 eq) of CuI, 8.87 g (0.5 eq) of ethylenediamine, K ₂ CO ₃ 89.83 g (2.0 eq) was dissolved in 1,4-dioxane, refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting residue was subjected to column chromatography to obtain 101.23 g (yield 85%) of Compound A-1.

2) Synthesis of Compound A-2

101.23 g (1.0 eq) of Compound A-1 was dissolved in 600 mL of anhydrous tetrahydrofuran, and then cooled to -78 째 C. 124 mL (1.0 eq) of n-butyllithium (2.5 M) was slowly added to the cooled solution and stirred at the same temperature for 30 minutes. 44.70 g (1.0 eq) of 9H-fluoren-9-one were added to the cooled mixture. When the reaction was completed, the mixture was warmed to room temperature, and a saturated aqueous ammonium chloride solution was added and stirred. The mixture was extracted with ethyl acetate, which was treated with anhydrous magnesium sulfate, filtered and then concentrated. An excess amount of hexane and a small amount of ethyl acetate were added to the concentrated compound, followed by stirring and filtration to obtain 102.60 g (yield: 82%) of Compound A-2.

3) Synthesis of Compound A-3

102.60 g (1.0 eq) of Compound A-2 was diluted in 700 mL of acetic acid, and then 2 mL of concentrated sulfuric acid was added and stirred for about 3 hours under reflux. After completion of the reaction, the mixture was cooled to room temperature, the solid was filtered, washed with ethanol and water in turn. The filtered solid was dissolved in chloroform and neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with water and separated, treated with anhydrous magnesium sulfate, filtered, and purified by recrystallization with addition of ethyl acetate. The purified solid was filtered to obtain 85.56 g (yield: 87%) of white Compound A-3.

4) Synthesis of Compound A-4

50.00 g (1.0 eq) of compound A-3, 14.42 g (1.1 eq) of 2-chloroaniline, 19.75 g (2.0 eq) of sodium tert- Of _{Pd (PPh 3) 4 1.18 g} (0.01 eq) and the mixture was stirred under reflux and dissolved in 300 ml of xylene (Xylene). When the reaction was completed, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed again to remove the solvent. The resulting residue was subjected to column chromatography to obtain 47.12 g (yield 86%) of the compound C-1.

5) Synthesis of Compound A-5

Compound A-4 47.12 g (1.0 eq) K ₃ PO ₄ 37.52 (2.0 eq), Pd (dba) ₂ 0.51 (0.01 eq), PCy ₃ 0.50 g (0.02 eq) was dissolved in 400 ml of DMAC, refluxed and stirred. When the reaction was completed, it was poured into 2 L of water and dropped solid. Thereafter, the solid was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and again reduced in pressure to remove the solvent. The resulting residue was subjected to column chromatography to obtain 32.04 g (yield 73%) of Compound A-5.

6) Preparation of Core Structure of Formula 2-1

The core structure of Formula 2-1 was prepared by applying various compounds of L2-Ar2 to the compound A-5.

Production Example 2. Preparation of Core Structure of Formula 2-2

B-2 was synthesized in the same manner as in Production Example 1, except that 1,4-dibromo-2-iodobenzene was used instead of 1,3-dibromo-2-iodobenzene. 2-chloroaniline and A2-L2r-X (X = Cl or Br) were synthesized by Buchwald-Hartwig cross coupling and B-2 and Buchwald- -2 core structure.

Production Example 3. Preparation of Core Structure of Formula 2-3

Except that 1,2-dibromo-3-iodobenzene was used instead of 1,3-dibromo-2-iodobenzene in Production Example 1 (1), the core structure of Formula 2-3 was prepared Respectively.

Production Example 4. Preparation of Core Structure of Formula 2-4

1) Synthesis of Compound C-1

After the compound A-3 85.56g (1.0 eq) , (2-nitrophenyl) boronic acid 32.29g (1.1 eq) prepared in 3) of Preparation Example 1 was dissolved in 400ml THF was dissolved in water 150ml K ₂ CO ₃ 48.62g (2.0 eq) were added. 0.45 g (0.005 eq) of Pd ( t- Bu ₃ P) ₂ was added and the mixture was refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and again reduced in pressure to remove the solvent. The resulting product was subjected to column chromatography to obtain 84.61 g (yield 91%) of Compound A-4.

2) Synthesis of Compound C-2

84.61 g (1.0 eq) of the compound C-1 was added to 200 mL of triethylphosphite, and the mixture was refluxed and stirred. After termination of the reaction, the reaction was poured into 2 liters of ethanol and the solid was dropped. The solid was completely dissolved in CHCl ₃ , washed with water and treated with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure and purified by column chromatography. 62.19 g (yield: 72%) of the compound C-2 was obtained.

3) Preparation of Core Structure of Formula 2-4

The core structure of Formula 2-4 was prepared by applying a variety of L2-Ar2 to the compound C-2.

Preparation Example 5. Preparation of Core Structure of Formula 2-5

Except that 2,4-dibromo-1-iodobenzene was used in place of 1,4-dibromo-2-iodobenzene in Production Example 2 to prepare the core structure of Formula 2-5.

Preparation Example 6. Preparation of Core Structure of Formula 2-6

Except that 1,2-dibromo-3-iodobenzene was used instead of 1,3-dibromo-2-iodobenzene in Production Example 4, the core structure of Formula 2-6 was prepared.

Preparation Example 7. Preparation of Core Structure of Formula 3-1

Except that 9H-carbazole was used instead of diphenylamine in Preparation Example 1 to prepare the core structure of Formula 3-1.

Preparation Example 8. Preparation of core structure of formula (3-2)

Except that 9H-carbazole was used instead of diphenylamine in Preparation Example 2, to prepare a core structure of Formula 3-2.

Preparation Example 9. Preparation of Core Structure of Formula 3-3

Except that 9H-carbazole was used instead of diphenylamine in Preparation Example 3, to prepare a core structure of Formula 3-3.

Preparation 10. Preparation of Core Structure of Formula 3-4

Except that 9H-carbazole was used instead of diphenylamine in Preparation Example 4 to prepare a core structure of Formula 3-4.

Preparation Example 11. Preparation of Core Structure of Formula 3-5

Except that 9H-carbazole was used instead of diphenylamine in Preparation Example 5, to prepare a core structure of Formula 3-5.

Preparation 12. Preparation of core structure of formula 3-6

Except that 9H-carbazole was used instead of diphenylamine in Preparation Example 6, to prepare a core structure of Formula 3-6.

Synthetic example

Synthesis Example 1. Synthesis of Compound 1

A solution of 10.00 g (1.0 eq) of compound E, 7.64 g (1.1 eq) of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 3.88 g (2.0 eq) of NaOtBu, ₃ P) ₂ 0.05 g (0.005 eq) was dissolved in 100 mL of xylene and refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed again to remove the solvent. The resulting residue was subjected to column chromatography to obtain 12.64 g (yield 78%) of Compound 1. [M] = 801

Synthesis Example 2. Synthesis of Compound 2

6.00 g (1.1 eq) of K ₂ PO _4, 8.58 g (2.0 eq.) Of K ₃ PO ₄ , and 1.0 g (1.0 eq) of 2-chloro-4-phenylbenzo [4,5] thieno [ 0.05 g (0.005 eq) of t-Bu ₃ P) ₂ was dissolved in 100 mL of xylene, refluxed and stirred. After completion of the reaction for 2 hours, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed to remove the solvent. Column chromatography was conducted to obtain 10.98 g (yield 72%) of Compound 2. [M + H] = 755

Synthesis Example 3. Synthesis of Compound 3

Compound E 10.00 g (1.0 eq), 2-chloro-4-phenylquinazoline 5.35 g (1.1 eq), K 3 PO 4 8.58 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) of The mixture was dissolved in 100 mL of xylene, refluxed and stirred. After completion of the reaction for 2 hours, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 10.59 g (yield 75%) of Compound 3. [M] = 699

Synthesis Example 4. Synthesis of Compound 4

Compound E 10.00 g (1.0 eq), 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline 7.04 g (1.1 eq), K 3 PO 4 8.58 g (2.0 eq), Pd (t -Bu ₃ P) ₂ (0.05 g, 0.005 eq) was dissolved in 100 mL of xylene, refluxed and stirred. After completion of the reaction for 2 hours, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 11.43 g (yield 73%) of Compound 4. [M + H] = 775

Synthesis Example 5. Synthesis of Compound 5

A mixture of 10.00 g (1.0 eq) of compound A-5, 7.61 g (1.1 eq) of 2- (4-chlorophenyl) -4,6- diphenyl- 1,3,5- triazine, 3.88 g (2.0 eq) of NaOtBu, -Bu ₃ P) ₂ (0.05 g, 0.005 eq) was dissolved in 100 mL of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 11.81 g (yield 73%) of Compound 5. [M + H] < + > = 804

Synthesis Example 6. Synthesis of Compound 6

Compound A-5 10.0 g (1.0 eq ), 2-chloro-4-phenylquinazoline 6.60 g (1.1 eq), K 3 PO 4 8.58 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq ) Was dissolved in 100 mL of xylene, refluxed and stirred. After completion of the reaction for 2 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water, treated with anhydrous magnesium sulfate, and then decompressed again to remove the solvent. The resulting residue was subjected to column chromatography to obtain 10.86 g (yield 77%) of Compound 6. [M] = 700

≪ Example 1 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying. Hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 50 Å to form a hole injection layer. HT1 (700 Å) for transporting holes was vacuum deposited thereon, followed by HT2 (200 Å) deposition. Compound 1 and dopant Dp-7 compound were vacuum-deposited as a host to a thickness of 300 Å in the light emitting layer. The amount of the dopant was 3 wt% based on the total amount of the host and the dopant. Then, an E1 compound (300 ANGSTROM) was sequentially vacuum-deposited by electron injection and transport layer. Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of LiF was 0.2 Å / sec, and the deposition rate of aluminum was 3 Å / sec to 7 Å / sec.

≪ Example 2 >

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

≪ Example 3 >

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

<Example 4>

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

&Lt; Example 5 >

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

&Lt; Example 6 >

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

&Lt; Comparative Example 1 &

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

&Lt; Comparative Example 2 &

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

&Lt; Comparative Example 3 &

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

&Lt; Comparative Example 4 &

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

Table 1 shows the results of the organic luminescent device manufactured by the above Examples 1 to 6 and Comparative Examples 1 to 4. Voltage, efficiency, and emission color are data at 5000 nit brightness. The lifetime is 100% of the initial photocurrent value, and the time of 98% is indicated.

division matter The driving voltage (V) Efficiency (cd / A) Life span T98 (hr) Luminous color Example 1 Compound 1 4.2 27.7 28 Red Example 2 Compound 2 4.3 27.2 37 Red Example 3 Compound 3 4.7 24.1 45 Red Example 4 Compound 4 4.5 24.6 48 Red Example 5 Compound 5 4.2 28.2 25 Red Example 6 Compound 6 4.4 25.5 51 Red Comparative Example 1 H-1 4.5 24.6 15 Red Comparative Example 2 H-2 4.9 22.1 32 Red Comparative Example 3 H-3 4.5 24.9 13 Red Comparative Example 4 H-4 4.7 23.5 9 Red

It can be seen from Table 1 that the organic electroluminescent device using the compound represented by Formula 1 according to one embodiment of the present invention has improved luminous efficiency while exhibiting red emission while lowering the driving voltage. The improvement effect was shown by up to 80% in the efficiency in comparison with the comparative examples H-1 to H-4, and the driving voltage was excellent overall. In Comparative Examples 1 and 3, although the driving voltage seems to be advantageous, the lifetime is about 30% of that of Example 6, and the lifetime of Comparative Example 2 is better than that of Example 1 and Example 5, Respectively. Comparative Example 4 showed the worst life. Accordingly, the compound of Formula 1 according to one embodiment of the present invention has advantages of high efficiency, low driving voltage and long life in an organic light emitting device.

1: substrate
2: anode
3: Hole injection layer
4: hole transport layer
5: light emitting layer
6: electron transport layer
7: cathode

Claims (10)

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

In Formula 1,
R1 to R17 and Ar1 are hydrogen,
Ar2 represents a phenyl group; A biphenyl group; A terphenyl group; Or represented by the following formula (A) or (B)
(A)

In the above formula (A)
Y1 to Y3 are the same or different and are each independently N or CRd,
R220 is a moiety bonded to Formula 1 through L1 or L2 of Formula 1,
R201 and Rd are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; Naphthyl group; A dibenzofurane group; Or a carbazolyl group substituted or unsubstituted with a phenyl group, or is bonded to adjacent substituents to form a ring,
Provided that when Y1 is CRd, Y2 and Y3 are N, and R201 is a phenyl group, Rd is not a phenyl group,
[Chemical Formula B]

In the above formula (B)
G ₁ is O, S, NR ₄₀₁ , or CR ₄₁₀ R ₄₁₁ ,
And U ₁ is N or CR _402, U ₂ is N or CR _403, U ₃ is N or CR _404, U ₄ is N or CR _405, U ₅ is N or CR _406, U ₆ is N or CR ₄₀₇ , U ₇ is N or CR ₄₀₈ , U ₈ is N or CR ₄₀₉ ,
When G ₁ is CR ₄₁₀ R ₄₁₁ , at least one of U ₁ to U ₈ is N,
Any one of R ₄₀₁ to R ₄₁₁ is a moiety bonded to the formula (1) via L 1 or L 2 in the formula (1), and the others are the same or different, and each independently hydrogen; Methyl group; A phenyl group; A biphenyl group; Or a naphthyl group,
a is 2
L1 and L2 are the same or different from each other and are each independently a direct bond; A phenylene group; Or a naphthylene group, and L1 may combine with R16 to form a ring. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In the general formula (2) or (3)
The definitions of R1 to R17, Ar1, Ar2, a and L2 are the same as those of the above formula (1)
R18 is hydrogen, b is 4, and c is 3. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (2-1) to (2-6)
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

In the general formulas (2-1) to (2-6)
The definitions of R1 to R17, Ar1, Ar2, a and L2 are the same as those of the above formula (1)
R18 is hydrogen, and b is 4. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3-1) to (3-6)
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

[Formula 3-5]

[Chemical Formula 3-6]

In the above formulas (3-1) to (3-6)
The definitions of R1 to R17, Ar1, Ar2, a and L2 are the same as those of the above formula (1)
R18 is hydrogen, and c is 3; delete delete The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 4 and 7, device. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer.

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