KR101891917B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound represented by Chemical Formula 1 and an organic light emitting device including the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and an organic light emitting device including the compound. [0002]

This application claims the benefit of Korean Patent Application No. 10-2016-0037161, filed on March 28, 2016, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

TECHNICAL FIELD The present invention relates to a novel compound and an organic light emitting device including 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.

International Patent Application Publication No. 2003-012890

The present invention provides a novel compound and an organic light emitting device including 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,

L1 and L2 are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

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

Ar2 is a structure represented by the following formula (2)

Ar 3 is a structure represented by the following formula (3)

(2)

In Formula 2,

Two of R2 to R9 are each a site to which L1 and L2 of the above formula 1 are bonded and the rest 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,

(3)

In Formula 3,

Any one of G1 to G11 is a moiety bonded to Ar2 through L2 in the above formula (1), and the others are the same or different, and are 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.

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 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.
Fig. 3 shows LC / MS data of formula A2. Fig.
4 shows LC / MS data of formula C2.
5 shows LC / MS data of formula F2.
6 shows LC / MS data of the formula G2.

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

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

In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

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 heteroaryl 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, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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, Phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, phthalidyl group, benzoquinazolyl group, benzoquinoxalyl group, indenopyrimidine benzopurepiri And benzothienopyrimidyl groups, but are not limited thereto.

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.

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

[Formula 1-1]

In Formula 1-1,

L1, L2 and Ar1 are the same as in the above formula (1)

R101, R102 and G101 to G103 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,

r101, r102, g101 and g102 are each an integer of 1 to 4,

g103 is an integer of 1 to 3,

r101 + r102? 6,

g101 + g103? 6,

When r101, r102 and g101 to g103 are two or more, the structures in parentheses of two or more are the same or different.

According to one embodiment of the present invention, any one of G1 to G11 is a site to be bonded to Ar2 through L2 in Formula 1, and the remainder is hydrogen.

According to one embodiment of the present disclosure, G101 to G103 are hydrogen.

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; An arylene group; Or a heteroarylene group.

According to one embodiment of the present invention, L1 to L3 are the same or different from each other, and each independently is a direct bond; A phenylene group; Biphenyllylene groups; Naphthylene group; According to one embodiment of the present invention, Ar 1 is an aryl group substituted or unsubstituted with an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, in the general formula (1), Ar1 represents an aryl group substituted or unsubstituted with an aryl group; A monocyclic heteroaryl group substituted or unsubstituted with at least one member selected from the group consisting of an aryl group, a heteroaryl group and an alkyl group; Or any one of groups represented by the following formulas (A) to (D).

(A)

In the above formula (A)

Wherein Y1 is N or R201, Y2 is N or R202, Y3 is N or R203, Y4 is N or R204, Y5 is N or R205, Y6 is N or R206, Y7 is N or R207,

Any one of R201 to R207 is a moiety bonded to Ar1 through L1 of Formula 1, and the remaining moieties are the same or different from each other and each independently represents hydrogen; An aryl group; Or a phosphine oxide group substituted with an aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

[Chemical Formula B]

In the above formula (B)

Y11 is N or R211, Y12 is N or R212, Y13 is N or R213, Y14 is N or R214, Y11 is N or R210, Y11 is N or R209,

Any one of R208 to R214 is a moiety bonded to Ar1 through L1 of Formula 1, and the remaining moieties are the same or different from each other and each independently represents hydrogen; An aryl group; Or a phosphine oxide group substituted with an aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

≪ RTI ID = 0.0 &

In the above formula (C)

T1 is N or R309, T2 is N or R310,

At least one of T1 and T2 is N,

Any one of R301 to R308 is a moiety bonded to Ar1 through L1 in the formula (1), and the remaining R309 and R310 are the same or different from each other, and each independently hydrogen; An aryl group; Or a phosphine oxide group substituted with an aryl group, or R301 and R302 are bonded to each other to form a ring substituted with Rc,

When R301 and R302 are bonded to each other to form a ring substituted with Rc, any one of R303 to R308 and Rc may be a site to be bonded to Ar1 through L1 of Formula 1,

Rc is hydrogen; An aryl group; Or a phosphine oxide group substituted with an aryl group.

[Chemical Formula D]

In the above formula (D)

G1 is O, S, NR401, or CR410R411,

U1 is N or R402, U2 is N or R403, U3 is N or R404, U4 is N or R405, U5 is N or R406, U6 is N or R407, U7 is N or R408, Lt; / RTI > is N or R409,

When G1 is CR410R411, at least one of U1 to U8 is N,

Any one of R401 to R411 is a moiety bonded to the formula (1) through L1 in the formula (1), and the remaining moieties are the same or different and each independently represents 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, the formula (A) is represented by any one of the following formulas (A-1) to (A-4).

[A-1]

[A-2]

[A-3]

[A-4]

In the above Formulas A-1 to A-4, the definitions of Y ₂ , Y ₃ , R ₂₀₁ and R ₂₀₄ to R ₂₀₇ are the same as in Formula A above.

According to one embodiment of the present invention, the formula (A) is represented by any one of the following formulas (A-5) to (A-12).

[A-5]

[A-6]

[A-7]

[A-8]

[A-9]

[A-10]

[A-11]

[A-12]

In the above formulas A-5 to A-12, the definitions of R201 to R207 are the same as those of the above formula (A).

According to one embodiment of the present invention, in formula (A), any one of R201 to R207 is a moiety bonded to Ar1 through L1 in the formula (1), and the remaining moieties are the same or different and independently hydrogen; A phenyl group; A biphenyl group; Or a naphthyl 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 formulas (B-1) to (B-4), Y8 and R209 to R214 have the same definitions as in 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-7).

[Formula B-5]

[Formula B-6]

[Formula B-7]

In the formulas (B-5) to (B-7), the definitions of R209 to R214 are the same as those of the formula (B).

According to one embodiment of the present invention, in formula (B), any one of R208 to R214 is a moiety bonded to Ar1 through L1 in the formula (1), and the remaining moieties are the same or different and independently hydrogen; A phenyl group; A biphenyl group; Or a naphthyl group.

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

[Chemical formula C-1]

In the above formula (C-1)

Any one of R301 to R308 is a moiety bonded to Ar1 through L1 in the formula (1), and the others are the same or different from each other, and each independently hydrogen; An aryl group; Or a phosphine oxide group substituted with an aryl group.

According to one embodiment of the present invention, the formula (C) is represented by the following formula (C-2).

[Chemical formula C-2]

In the above formula (C-2)

Any one of R301 to R308 and R311 to R314 is a moiety bonded to Ar1 through L1 in the formula (1), and the others are the same or different from each other and each independently hydrogen; An aryl group; Or a phosphine oxide group substituted with an aryl group.

According to one embodiment of the present invention, in the above formulas C-1 and C-2, any one of R301 to R314 is a site bonded to Ar1 through L1 in the above formula (1), and the remainder is hydrogen.

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

[Formula D-1]

[Formula D-2]

[Formula D-3]

[Formula D-4]

In the above formulas (D-1) to (D-4)

The definitions of U1 to U4, R401 and R406 to R411 are the same as those of the above formula (D).

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

[Formula D-5]

[Formula D-6]

[Formula D-7]

[Formula D-8]

[Chemical formula D-9]

[Formula D-10]

[Formula D-11]

[Formula D-12]

[Formula D-13]

[Chemical Formula D-14]

[Formula D-15]

In the above formulas D-5 to D-15, the definitions of R401 to R411 are the same as those of the above formula (D).

According to one embodiment of the present invention, any one of R401 to R411 is a moiety bonded to Formula (1) via L1 in Formula (1), and the remaining moieties may be the same or different 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 R401 to R411 is a moiety bonded to Formula (1) via L1 in Formula (1), and the remaining moieties may be the same or different and each independently hydrogen; An alkyl group; Or an aryl group.

According to one embodiment of the present invention, any one of R401 to R411 is a moiety bonded to Formula (1) via L1 in Formula (1), and the remaining moieties may be the same or different and each independently hydrogen; Methyl group; A phenyl group; A biphenyl group; Or a naphthyl group.

According to one embodiment of the present invention, Ar1 is an aryl group substituted or unsubstituted with an aryl group; Or a heteroaryl group substituted or unsubstituted with at least one member selected from the group consisting of an aryl group, a heteroaryl group and an alkyl group.

According to one embodiment of the present invention, Ar1 represents a phenyl group substituted or unsubstituted with an aryl group; A biphenyl group; Naphthyl group; A terphenyl group; A pyrimidyl group substituted or unsubstituted with at least one member selected from the group consisting of an aryl group and a heteroaryl group; A substituted or unsubstituted triazinyl group selected from the group consisting of an aryl group and a heteroaryl group; A quinazolyl group substituted or unsubstituted with an aryl group; A carbazolyl group substituted or unsubstituted with an aryl group; A benzoquinazolyl group substituted or unsubstituted with an aryl group; A benzofuranopyrimidyl group substituted or unsubstituted with an aryl group; Benzothienopyrimidyl substituted or unsubstituted with an aryl group; An indenopyrimidyl group substituted or unsubstituted with at least one member selected from the group consisting of an aryl group, a heteroaryl group and an alkyl group; A quinoxalyl group substituted or unsubstituted with an aryl group; A pyridopyrimidyl group substituted or unsubstituted with an aryl group; A phthalidyl group substituted or unsubstituted with an aryl group; A pyridopyrimidinyl group substituted or unsubstituted with an aryl group; Or a pyrazinopyranyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar1 represents a phenyl group substituted or unsubstituted with a phenyl group; A biphenyl group; Naphthyl group; A terphenyl group; A pyrimidyl group substituted or unsubstituted with at least one member selected from the group consisting of a phenyl group and a biphenyl group; A triazinyl group substituted or unsubstituted with at least one member selected from the group consisting of a phenyl group, a biphenyl group and a dibenzofuranyl group; A quinazolyl group substituted or unsubstituted with a phenyl group, a biphenyl group or a naphthyl group; A carbazolyl group substituted or unsubstituted with a phenyl group; A benzoquinazolyl group substituted or unsubstituted with a phenyl group; A benzofuranopyrimidyl group substituted or unsubstituted with a phenyl group, a biphenyl group or a naphthyl group; A benzothienopyrimidyl group substituted or unsubstituted with a phenyl group, a biphenyl group or a naphthyl group; An indenopyrimidyl group which is substituted or unsubstituted with at least one member selected from the group consisting of a methyl group, a phenyl group, a biphenyl group and a naphthyl group; A quinoxalyl group substituted or unsubstituted with a phenyl group or a naphthyl group; A pyridopyrimidyl group substituted or unsubstituted with a phenyl group; A phthalidyl group substituted or unsubstituted with a phenyl group; A pyridopyrimidinyl group substituted or unsubstituted with a phenyl group; Or a pyrazinopyranyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, Formula 1 is selected from the following compounds.

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 compound described above.

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 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 an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes at least one host and at least one dopant, and the at least one host includes the compound represented by the formula (1).

According to another embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes two hosts, and at least one of the hosts includes a compound represented by the formula (1).

According to another embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes two hosts, and each host is contained in a weight ratio of 1:99 to 99: 1. Preferably, each host is contained at a weight ratio of 50:50, and at least one of the hosts includes the compound represented by the above formula (1).

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

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 second electrode 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.

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 with a low work function followed by an aluminum layer or 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 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 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.

The compound according to one embodiment of the present invention is prepared by using Buchwald-Hartwig coupling reaction, Heck coupling reaction, Suzuki coupling reaction, or the like as a typical reaction.

≪ Preparation of Derivative of Formula 3 (Ar3)

PREPARATION EXAMPLE 1. Preparation of Formulas 1-c

1) Preparation of formula (I-a)

, 100.00 g (1.0 eq) of 9H-carbazole and 100.74 g (1.5 eq) of KOtBu were placed in 1 L of DMF (Dimethylmethanamide) and heated and stirred. At the beginning of the reflux, 150.43 g (1.2 eq) of 1-bromo-3-chloro-2-fluorobenzene was added. After the reaction was completed after 5 hours, the reaction product was poured into water and the crystals were dropped and filtered. The filtered solid was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent, which was purified by column chromatography. 187.85 g (yield: 88%) of the compound of the formula 1-a was obtained.

2) Preparation of compound of formula 1-b

To 187.85 g (1.0 eq) of the formula 1-a was added Pd (t-Bu ₃ P) ₂ 1.19 g (0.005 eq) of K ₂ CO _{3 and} 129.74 g (2.00 eq) of K ₂ CO _{3 were} placed in 1 L of dimethylacetamide, refluxed and stirred. After 3 hours, the reaction mixture was poured into water, and crystals were dropped and filtered. The filtered solid was completely dissolved in ethyl acetate and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. 97.89 g (yield 76%) of the compound of the formula 1-b was obtained.

3) Preparation of formula (1-c)

135.23 g (1.5 eq) of bis (pinacolato) diboron, 4.08 g (0.02 eq) of Pd (dba) ₂ , 97.29 g (0.02 eq) of PCi ₃ 3.98 g (0.04 eq) of KOAc and 98.13 g (2.00 eq) of KOAc were placed in 70 mL of dioxane, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 105.61 g (yield 81%) of the compound of the formula 1-c was obtained

PREPARATION EXAMPLE 2 Preparation of Formula 2-c

Except that 1-bromo-4-chloro-2-fluorobenzene was used instead of 1-bromo-3-chloro-2-fluorobenzene in Production Example 1 to synthesize Formula 2-c.

PREPARATION EXAMPLE 3 Preparation of Formula 3-c

Except that 2-bromo-4-chloro-1-fluorobenzene was used instead of 1-bromo-3-chloro-2-fluorobenzene in Production Example 1 to synthesize Formula 3-c.

Production Example 4. Preparation of the compound of the formula 4-c

4-c was synthesized in the same manner as in Production Example 1 except that 2-bromo-1-chloro-3-fluorobenzene was used instead of 1-bromo-3-chloro-2-fluorobenzene.

Production Example 5. Preparation of Formula 5-c

Except that 4-chloro-9H-carbazole was used instead of 9H-carbazole in Production Example 1 and 1-bromo-2-fluorobenzene was used in place of 1-bromo-3-chloro-2-fluorobenzene. -c was synthesized.

Production Example 6. Preparation of the compound of the formula 6-c

Except that 1-bromo-2-fluorobenzene was used instead of 3-chloro-9H-carbazole and 1-bromo-3-chloro-2-fluorobenzene in place of 9H-carbazole in Preparation Example 1, Synthesized.

≪ Preparation of Derivative of Formula 2 (Ar2) >

Preparation 7. Preparation of the compound of the formula 7-d

1) Preparation of formula 7-a

3-bromo-2-mercaptophenol (50 g, 0.26 mol) and (3-chloro-2-fluorophenyl) boronic acid (46.1 g, 0.21 mol) were dissolved in 500 ml of tetrahydrofuran in a 2000 ml round- After adding 1.5 M aqueous potassium carbonate solution (400 ml), bis (tri- tert- butylphosphine) palladium (0) (1.35 g, 2.36 mmol) was added and the mixture was heated with stirring for 1 hour. (49.8 g, yield 79%, MS: [M (M)]. The title compound was obtained as a white amorphous solid in a yield of 79%, and the solvent was distilled off under reduced pressure. The residue was recrystallized from hexane + H] < ⁺ > = 239).

2) Preparation of compound of formula 7-b

In a 500 ml round bottom flask The compound of formula 7-a (49.8 g, 0.21 mol) and calcium carbonate (57.7 g, 0.42 mol) were dissolved in 200 ml of N-methyl-2-pyrrolidone and the mixture was heated with stirring for 2 hours. The temperature is lowered to room temperature and the solution is reprecipitated in water. (31.8 g, yield 70%, MS: [M + H] < + >) was prepared in the same manner as in Example 1, ⁺ = 219).

3) Preparation of compound of formula 7-c

In a 500 ml round bottom flask The nonafluorobutanesulfonyl fluoride (28.7 ml, 0.16 mol) was added to the reaction mixture at 0 ° C for 30 minutes, and the reaction mixture was stirred at room temperature for 3 hours. Let it fall slowly. Thereafter, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was filtered and completely dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, and dried to produce the compound of Formula 7-c (53.3 g, yield 73% : [M + H] < ⁺ > = 501).

4) Preparation of the compound of formula 7-d

7-c Dioxaborane (28.4 g, 17.85 mol), Pd (dppf) Cl ₂ (0.78 g, 1.06 mmol), KOAc (31.3 g, 0.32 mol) were placed in 650 mL of dioxane and stirred at reflux for 8 hours. The temperature was lowered to room temperature and the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl3, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. (30.1 g, yield 86%, MS: [M + H] < ⁺ > = 329).

5) The compound of the present invention was synthesized by Suzuki coupling or Buchwald-Hartwig coupling reaction using the compound of the formula 7-d as a starting material.

Preparation 8. Preparation of the compound of the formula 8-d

8-d was synthesized in the same manner as in Production Example 7 except that (4-chloro-2-fluorophenyl) boronic acid was used instead of (3-chloro-2-fluorophenyl) boronic acid.

Production Example 9. Preparation of the compound of the formula 9-d

9-d was synthesized in the same manner as in Production Example 7 except that (5-chloro-2-fluorophenyl) boronic acid was used instead of (3-chloro-2-fluorophenyl) boronic acid.

Preparation 10. Preparation of Formula 10-d

10-d was synthesized in the same manner as in Production Example 7 except that (2-chloro-6-fluorophenyl) boronic acid was used instead of (3-chloro-2-fluorophenyl) boronic acid.

Preparation Example 11. Preparation of the compound of the formula 11-d

11-d was synthesized except that 4-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol in Production Example 7.

Preparation 12. Preparation of Formula 12-d

Except that 4-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol and 4-chloro-2-fluorophenyl boronic acid was used in place of (3-chloro-2- Were prepared in the same manner to synthesize the compound of the formula (12-d).

Preparation 13. Preparation of the compound of the formula 13-d

Except that 4-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol in Production Example 7 and 5-chloro-2-fluorophenyl boronic acid was used instead of (3-chloro-2- Were prepared in the same manner to synthesize the compound of the formula (13-d).

Preparation 14. Preparation of the compound of formula 14-d

Except that 4-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol and 2-chloro-6-fluorophenyl boronic acid was used in place of (3-chloro-2-fluorophenyl) Were prepared in the same manner to synthesize the compound of formula (14-d).

Preparation 15. Preparation of the compound of formula 15-d

Except that 3-bromo-4-mercaptophenol was used instead of 3-bromo-2-mercaptophenol in Production Example 7 to synthesize the compound of Formula 15-d.

Preparation 16. Preparation of Formula 16-d

Except that 3-bromo-4-mercaptophenol was used instead of 3-bromo-2-mercaptophenol and 4-chloro-2-fluorophenyl boronic acid was used in place of (3-chloro-2- Were prepared in the same manner to synthesize the compound of formula (16-d).

Preparation 17. Preparation of the compound of formula 17-d

Except that 3-bromo-4-mercaptophenol was used instead of 3-bromo-2-mercaptophenol in Production Example 7 and 5-chloro-2-fluorophenyl boronic acid was used instead of (3-chloro-2- Were prepared in the same manner to synthesize the compound of formula (17-d).

Preparation 18. Preparation of the compound of formula 18-d

Except that 3-bromo-4-mercaptophenol was used instead of 3-bromo-2-mercaptophenol and 2-chloro-6-fluorophenyl boronic acid was used in place of (3-chloro-2-fluorophenyl) Was prepared in the same manner to synthesize the compound of formula 18-d.

Preparation 19. Preparation of the compound of formula 19-d

In the same manner as in Production Example 7 except that 2-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol, 19-d was synthesized.

Preparation 20. Preparation of 20-d

Except that 2-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol and 4-chloro-2-fluorophenyl boronic acid was used in place of (3-chloro-2- Were prepared in the same manner to synthesize the compound of formula (20-d).

Preparation 21. Preparation of (21-d)

Except that 2-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol in Production Example 7 and 5-chloro-2-fluorophenyl boronic acid was used instead of (3-chloro-2- Were prepared in the same manner to synthesize the compound of the formula (21-d).

Preparation 22. Preparation of Formula 22-d

Except that 2-bromo-3-mercaptophenol was used instead of 3-bromo-2-mercaptophenol in Production Example 7 and (2-chloro-6-fluorophenyl) boronic acid was used instead of (3-chloro-2- Was prepared in the same manner to synthesize the compound of formula 22-d.

<Synthesis Example>

Synthesis Example 1. Synthesis of Compound (A2)

Formula 18-d 10.00 g (1.0 eq ), 2-chloro-4,6-diphenyl-1,3,5-triazine 8.96 g (1.1 eq) 8.41 g (1.1 eq), Pd (t-Bu 3 P) 2 8.41 g (2.00 eq) of 0.07 g (0.005 eq) of K ₂ CO ₃ dissolved in water was added to 70 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 9.77 g (yield 74%) of the formula A1 was obtained.

(0.005 eq) of Pd (t-Bu ₃ P) ₂ , 9.55 g (2.0 eq) of K ₃ PO ₄ dissolved in water, 9.09 g (1.1 eq) Dissolved in 90 ml of dioxane, refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 10.49 g (yield: 73%) of the compound represented by the formula A2.

Fig. 3 shows LC / MS data of formula A2. Fig.

Synthesis Example 2. Synthesis of Compound (B2)

11.07 g (1.0 eq) of Pd (t-Bu ₃ P) ₂ (10 eq), 1.0 g (1.0 eq) of 2-chloro-4- (naphthalen- 8.41 g (2.00 eq) of 0.07 g (0.005 eq) of K ₂ CO ₃ dissolved in water was added to 70 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 10.73 g (71% yield) of the compound of formula B1 was obtained.

Formula B1 10.73 g (1.0 eq), the general formula 2-c 8.72 g (1.1 eq ), K 3 PO 4 9.16 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) dissolved in water Dissolved in 90 ml of dioxane, refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 10.60 g (yield: 70%) of compound (B2).

Synthesis Example 3. Synthesis of Compound (C2)

13.43 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (0.1 eq), 2- (4-bromophenyl) -4-phenylbenzofuro [ 8.41 g (2.00 eq) of 0.07 g (0.005 eq) of K ₂ CO ₃ dissolved in water was added to 70 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 11.14 g (yield 70%) of the formula C1 was obtained.

Formula C1 11.14 g (1.0 eq), the compound of Formula 3-c 5.60 g (1.1 eq ), K 3 PO 4 9.04 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) dissolved in water Dissolved in 90 ml of dioxane, refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 11.31 g (yield 73%) of the formula C2.

4 shows LC / MS data of formula C2.

Synthesis Example 4. Synthesis of Compound D2

(1.0 eq), 15.54 g (1.1 &lt; RTI ID = 0.0 &gt; eq), Pd (t-Bu ₃ P) ₂ 8.41 g (2.00 eq) of 0.07 g (0.005 eq) of K ₂ CO ₃ dissolved in water was added to 70 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 12.66 g (71% yield) of the formula D1 was obtained.

Formula D1 12.66 g (1.0 eq), the compound of Formula 5-c 8.72 g (1.1 eq ), K 3 PO 4 9.17 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) dissolved in water Dissolved in 90 ml of dioxane, refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 12.81 g (yield 75%) of the formula D2.

Synthesis Example 5. Synthesis of Compound E2

8.00 g (1.1 eq) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 10 g of Pd (t-Bu ₃ P) ₂ 8.41 g (2.00 eq) of 0.07 g (0.005 eq) of K ₂ CO ₃ dissolved in water was added to 70 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 9.77 g (yield 74%) of the compound E1 was obtained.

Formula E1 9.77 g (1.0 eq), the compound of Formula 6-c 9.09 g (1.1 eq ), K 3 PO 4 9.55 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) dissolved in water Dissolved in 90 ml of dioxane, refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 10.35 g (yield 72%) of a compound represented by the formula E2.

Synthesis Example 6. Synthesis of Formula F2

12.99 g (1.1 eq) of Pd (t-Bu ₃ P) ₂ (0.1 eq), 2- (3-bromophenyl) -4,6-diphenyl- 8.41 g (2.00 eq) of 0.07 g (0.005 eq) of K ₂ CO ₃ dissolved in water was added to 70 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 11.32 g (yield 73%) of Formula F1 was obtained.

Formula F1 11.32 g (1.0 eq), the compound of Formula 6-c 8.96 g (1.1 eq ), K 3 PO 4 9.42 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) dissolved in water Dissolved in 90 ml of dioxane, refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 10.20 g (yield: 72%) of the formula F2.

5 shows LC / MS data of formula F2.

Synthesis Example 7. Synthesis of Compound G2

A mixture of 10.00 g (1.0 eq) of the compound of the formula 21-d, 15.54 g of (2- (3'-bromo- [1,1'- biphenyl] eq), Pd (t-Bu ₃ P) ₂ 8.41 g (2.00 eq) of 0.07 g (0.005 eq) of K ₂ CO ₃ dissolved in water was added to 70 ml of THF, and the mixture was refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 13.55 g (yield 76%) of the formula G1 was obtained.

Formula G1 13.55 g (1.0 eq), the compound of Formula 3-c 9.39 g (1.1 eq ), K 3 PO 4 9.81 g (2.0 eq), Pd (t-Bu 3 P) 2 0.05 g (0.005 eq) dissolved in water Dissolved in 90 ml of dioxane, refluxed and stirred. After 3 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 10.48 g (yield 71%) of a compound G2.

6 shows LC / MS data of the formula G2.

&Lt; Comparative Example 1 &

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with 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 the ITO transparent electrode thus prepared, a hole injection layer was formed by thermal vacuum deposition of HAT-CN of the following formula to a thickness of 500 Å.

On the hole injection layer, the HTL of the following formula was thermally vacuum deposited to a thickness of 800 ANGSTROM, and a hole transport layer was formed by sequentially vacuum-depositing HTG to a thickness of 500 ANGSTROM.

Then, the hole transport layer was co-deposited with the phosphorescent dopant DP-33 at a weight ratio of 5 to 10% of Formula H-1 to form a 400Å thick light emitting layer.

On the light emitting layer, a hole blocking layer was formed by vacuum evaporation of the following formula (ET-1) to a thickness of 50 ANGSTROM, and an electron transport layer of 250 ANGSTROM was vacuum deposited on the hole blocking layer at a weight ratio of 1: . Lithium fulleride (LiF) was sequentially deposited on the electron transporting layer to a thickness of 10 Å, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr.

<Experimental Example 1>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound of Formula A2 was used instead of the compound of Formula H-1.

<Experimental Example 2>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that Compound B2 was used instead of Compound H-1 in Comparative Example 1.

<Experimental Example 3>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound C2 was used instead of the compound H-1 in Comparative Example 1.

<Experimental Example 4>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound of Formula D2 was used instead of the compound of Formula H-1 in Comparative Example 1.

<Experimental Example 5>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound of Formula E2 was used instead of the compound of Formula H-1.

<Experimental Example 6>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound of Formula F2 was used instead of the compound of Formula H-1 in Comparative Example 1.

<Experimental Example 7>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound G2 was used instead of the compound H-1 in the above Comparative Example 1.

&Lt; Comparative Example 2 &

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

&Lt; Comparative Example 3 &

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

&Lt; Comparative Example 4 &

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

The Voltage V
(@ 10 mA / cm ² ) Efficiency cd / A
(@ 10 mA / cm ² ) Luminous color T95
(@ 20 mA / cm ² ) Comparative Example 1 H-1 4.03 50.0 green 47 Experimental Example 1 Formula A2 3.67 57.9 green 80 Experimental Example 2 Formula B2 3.69 57.3 green 77 Experimental Example 3 C2 3.72 57.0 green 70 Experimental Example 4 Formula D2 3.80 56.0 green 67 Experimental Example 5 E2 3.68 57.5 green 78 Experimental Example 6 Formula F2 3.84 55.8 green 65 Experimental Example 7 G2 3.87 55.0 green 65 Comparative Example 2 H-3 3.93 50.7 green 49 Comparative Example 3 H-4 3.90 51.1 green 50 Comparative Example 4 H-5 3.91 52.5 green 51

&Lt; Comparative Example 5 &

H-1 and H-2 were used instead of the formula H-1 in Comparative Example 1 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

<Experimental Example 8>

(A2) and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

<Experimental Example 9>

In Comparative Example 1, instead of the formula (H-1), the formula B2 and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

<Experimental Example 10>

In Comparative Example 1, instead of the formula (H-1), the formula C2 and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

&Lt; Experimental Example 11 &

In the above Comparative Example 1, instead of the formula H-1, the formula D2 and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

<Experimental Example 12>

In the above Comparative Example 1, instead of the formula H-1, the compounds of the formulas E2 and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

<Experimental Example 13>

In the above Comparative Example 1, instead of the formula H-1, the formula F2 and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

<Experimental Example 14>

In the above Comparative Example 1, instead of the formula (H-1), G2 and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

&Lt; Comparative Example 6 >

H-3 and H-2 were used instead of the formula H-1 in Comparative Example 1 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

&Lt; Comparative Example 7 &

H-4 and H-2 were used instead of the formula H-1 in Comparative Example 1 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

&Lt; Comparative Example 8 >

In Comparative Example 1, instead of the formula H-1, the formulas H-5 and H-2 Was used in a weight ratio of 50:50, an organic light emitting device was fabricated in the same manner as in Comparative Example 1.

The Voltage V
(@ 10 mA / cm ² ) Efficiency cd / A
(@ 10 mA / cm ² ) Luminous color T95
(@ 20 mA / cm ² ) Comparative Example 5 H-1, H-2 4.33 55.0 green 121 Experimental Example 8 The formula A2, H-2 3.91 63.1 green 147 Experimental Example 9 B2, H-2 3.97 60.5 green 140 Experimental Example 10 The formula C2, H-2 4.02 61.5 green 138 Experimental Example 11 The formula D2, H-2 4.00 62.1 green 133 Experimental Example 12 The compounds of formula E2, H-2 3.93 62.5 green 144 Experimental Example 13 Formula F2, H-2 4.10 61.4 green 128 Experimental Example 14 G2, H-2 4.13 61.0 green 130 Comparative Example 6 H-3, H-2 4.28 58.1 green 95 Comparative Example 7 H-4, H-2 4.23 59.0 green 101 Comparative Example 8 H-5, H-2 4.15 58.5 green 103

The results shown in Table 1 and Table 2 show that the compound represented by Formula 1 of the present invention has the advantages of low driving voltage, high efficiency, and long life, compared to Formula H-1, which is a green light emitting host material conventionally used conventionally. Compared with Formulas H-3 to H-5, which are comparative examples in which dibenzo [b, d] thiophen has a heteroaryl group and indolo [3,2,1-jk] carbazole bonded at the same time, The organic light emitting device including the compound represented by Formula 1 has advantages of low driving voltage, high efficiency, and long life.

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 (8)

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

In Formula 1,
L1 is a direct bond; A phenylene group; Biphenyllylene groups; Naphthylene group; Or a quinazolylene group,
L2 is a direct bond,
Ar1 is a pyrimidyl group substituted by at least one member selected from the group consisting of a phenyl group and 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 dibenzofuranyl group; A quinazolyl group substituted with a phenyl group, a biphenyl group or a naphthyl group; A carbazolyl group substituted or unsubstituted with a phenyl group; A benzoquinazolyl group substituted with a phenyl group; A benzofuranopyrimidyl group substituted with a phenyl group or a naphthyl group; A benzothienopyrimidyl group substituted with a phenyl group, a biphenyl group or a naphthyl group; An indenopyrimidyl group substituted by at least one member selected from the group consisting of a methyl group and a phenyl group; A quinoxalyl group substituted with a phenyl group or a naphthyl group; A pyridopyrimidyl group substituted with a phenyl group; A phthalidyl group substituted with a phenyl group; A pyridopyranyl group substituted with a phenyl group; Or a pyrazinopyranyl group substituted with a phenyl group,
Provided that when Ar1 is a carbazolyl group substituted or unsubstituted with a phenyl group, L1 is a quinazolylene group,
R101, R102 and G101 to G103 are hydrogen,
r101, r102, g101 and g102 are each an integer of 1 to 4,
g103 is an integer of 1 to 3,
r101 + r102? 6,
g101 + g103 &lt; / = 6. delete delete delete The compound according to claim 1, wherein the compound of formula (1) is selected from the following compounds:

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 includes a compound according to any one of claims 1 and 5. Light emitting element. 7. The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. 7. The organic light emitting device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host of the light emitting layer.

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