KR101778359B1

KR101778359B1 - Hetero-cyclic compound and organic light emitting device comprising the same

Info

Publication number: KR101778359B1
Application number: KR1020150076448A
Authority: KR
Inventors: 하재승; 곽지원
Original assignee: 주식회사 엘지화학
Priority date: 2014-05-29
Filing date: 2015-05-29
Publication date: 2017-09-14
Also published as: KR20150138105A

Abstract

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

Description

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

This application claims the benefit of the filing date of Korean Patent Application No. 10- 2014-0065397 filed on May 29, 2014 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

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

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

Korean Patent Publication No. 2000-0051826

Heterocyclic compounds and organic light emitting devices containing them are described in this specification.

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

[Chemical Formula 1]

In Formula 1,

L ₁ is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

L ₂ is a direct bond; Or substituted or unsubstituted arylene,

Y ₁ and Y ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

S ₁ and S ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group, or an adjacent two or more substituents bonded to each other to form a ring,

m1 and m2 are the same or different and each independently an integer of 0 to 10,

n1 and n2 are the same or different and each independently an integer of 1 to 10,

a is an integer of 0 to 4, b is an integer of 0 to 5,

When m1 is 2 or more, L < ₁ >

If more than n1 is 2 and Y ₁ are the same as or different from each other,

m2 or more is 2 L ₂ are the same as or different from each other, and

when n2 is 2 or more, Y < ₂ >

When a is 2 or more, S < ₁ >

when b is 2 or more, S ₂ are the same or different from each other.

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

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting materials.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

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

An embodiment of the present invention provides a compound represented by the above formula (1).

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; A heterocyclic group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; A heteroarylamine group; Or an arylamine group, or does not have any substituent (s). These substituents may further have a substituent.

In the present specification, the halogen group includes, but is not limited to, fluorine, chlorine, bromine iodine, and the like.

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

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

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

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

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

When the fluorenyl group is substituted

,

,

And

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

In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, S and Se as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzooxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

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

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

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

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, the N-arylheteroarylamine group and the N-alkylarylamine group is the same as the above-mentioned aryl group.

In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, the alkylamine group, the N-alkylarylamine group and the N-alkylheteroarylamine group is the same as the alkyl group described above.

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

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

In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group.

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.

In the present specification, the term "two or more adjacent substituents bonded to each other to form a ring" in the present specification means a substituted or unsubstituted hydrocarbon ring bonded to adjacent groups to form a ring; Or a substituted or unsubstituted heterocycle.

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

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

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

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be 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, L &_lt; ₁ > Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene, and L ₂ is substituted or unsubstituted arylene.

According to one embodiment of the present invention, L < 1 > in the general formula ( ₁₎ is substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene, and L ₂ is substituted or unsubstituted arylene.

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

According to one embodiment of the present invention, L ₁ and L ₂ in formula (1) may be selected from the following structures.

In the above structural formulas, U ₁ to U ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

p1, p2 and p3 are integers of 0 to 4, p4 and p5 are integers of 0 to 3,

When p1 is 2 or more, U < ₁ >

When p2 is 2 or more, U < ₂ >

If more than p3 is 2 U ₃ is the same as or different from each other, and

If more than p4 is 2 U ₄ is equal to or below the au each other,

When p5 is 2 or more, U < ₅ >

In the above formula, U ₁₁ to U _13, U ₂₁ to U _23, U ₃₁ to U _33, U ₄₁ to U ₄₃ and U ₅₁ to U ₅₃ is the same as or different from each other, each independently represent the above-mentioned U ₁ To U ₅ ,

p11 to p13, p21 to p23, p31 to p33 and p53 are integers of 0 to 4,

p41, p42, p51 and p52 are integers of 0 to 3,

p43 is an integer of 0 to 2,

or more p11 is 2 and U ₁₁ is the same as or different from each other,

or more p12 is 2 U ₁₂ is the same as or different from each other, and

or more p13 is 2 and U ₁₃ is the same as or different from each other,

or more p21 is 2 U ₂₁ is the same as or different from each other, and

or more p22 is 2 and U ₂₂ is the same as or different from each other,

When p23 is 2 or more, U < ₂₃ > are the same or different from each other,

When p31 is 2 or more, U ₃₁ are the same or different from each other,

or more p32 is 2 U ₃₂ is the same as or different from each other, and

or more p33 is 2 and U ₃₃ is the same as or different from each other,

When p41 is 2 or more, U ₄₁ are the same or different from each other,

If more than two p42 and U ₄₂ is the same as or different from each other,

When p43 is 2 or more, U ₄₃ are the same or different from each other,

or more p51 is 2 and U ₅₁ is the same as or different from each other,

or more p52 is 2 U ₅₂ is the same as or different from each other, and

When p53 is 2 or more, U ₅₃ is the same or different.

According to one embodiment of the present invention, Y ₁ and Y ₂ in the general formula (1) are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heteroarylamine group.

According to one embodiment of the present invention, Y ₁ and Y ₂ in the general formula (1) are substituted or unsubstituted phenyl groups; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted phenanthryl group.

According to one embodiment of the present invention, Y ₁ and Y ₂ in Formula 1 may be selected from the following structures.

In the above structural formulas, T ₁ to T ₅₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

t1, t3, t5, t7, t9, t16, t21, t43, t44, t47, t50 and t53 are the same or different and independently an integer of 0 to 5,

t2, t4, t6, t10, t12, t14, t15, t17, t18, t19, t20, t22, t23, t25, t26, t27, t29, t30, t32, t35, t38, t40, t41, t48, t49, t51 and t52 are the same or different and independently of one another an integer of 0 to 4,

t8, t11, t24, t28, t33, t36, t39 and t42 are the same or different and each independently an integer of 0 to 3,

t13 and t31 are the same or different and independently of one another an integer of 0 or 1,

t34 and t37 are the same or different and independently of one another an integer of 0 to 2,

If there is more than t1 is 2 T ₁ is the same as or different from each other, and

When t2 is 2 or more, T < ₂ >

If more than t3 is 2 T ₃ it is the same as or different from each other, and

If there is more than the t4 2 T ₄ are the same or different from each other and,

If more than t5 is 2 T ₅ it is the same as or different from each other, and

If more than t6 is 2 and T ₆ are the same or different from each other,

If more than t7 is 2 T ₇ is the same as or different from each other, and

If more than t8 the 2 and T ₈ are the same as or different from each other,

If there is more than 2 T ₉ are t9 is the same as or different from each other, and

If t10 is greater than or equal to 2 and T ₁₀ are the same or different from each other,

If more than t11 is 2 T ₁₁ is the same as or different from each other, and

When t ₁₂ is 2 or more, T ₁₂ are the same or different from each other,

If more than t13 is 2 T ₁₃ is the same as or different from each other, and

If more than t14 is 2 T ₁₄ are the same or different from each other and,

If more than t15 is 2 T ₁₅ is the same as or different from each other, and

If more than t16 is 2 T ₁₆ are the same or different from each other and,

When t ₁₇ is 2 or more, T ₁₇ are the same or different from each other,

When t ₁₈ is 2 or more, T ₁₈ are the same or different from each other,

When t ₁₉ is 2 or more, T ₁₉ are the same or different from each other,

If more than t20 is 2 and T ₂₀ are the same or different from each other,

If more than t21 is 2 T ₂₁ is the same as or different from each other, and

If more than t22 is 2 T ₂₂ are the same or different from each other and,

When t23 is 2 or more, T < ₂₃ > are the same or different from each other,

If more than t24 is 2 T ₂₄ are the same or different from each other and,

If more than t25 is 2 T ₂₅ is the same as or different from each other, and

When t 26 is 2 or more, T ₂₆ are the same or different from each other,

When t27 is 2 or more, T < ₂₇ > are the same or different from each other,

If more than t28 is 2 T ₂₈ are the same or different from each other and,

When t29 is 2 or more, T < ₂₉ >

If more than t30 is 2 T ₃₀ are the same or different from each other and,

When t ₃₁ is 2 or more, T ₃₁ are the same or different from each other,

If more than t32 is 2 and T ₃₂ are the same or different from each other,

If more than t33 is 2 T ₃₃ is the same as or different from each other, and

If more than t34 is 2 and T ₃₄ are the same or different from each other,

If more than t35 is 2 T ₃₅ is the same as or different from each other, and

If more than t36 is 2 and T ₃₆ are the same or different from each other,

When t37 is 2 or more, T < ₃₇ >

If more than t38 is 2 and T ₃₈ are the same or different from each other,

If more than t39 is 2 T ₃₉ is the same as or different from each other, and

When t ₄₀ is 2 or more, T ₄₀ are the same or different from each other,

If more than t41 is 2 T ₄₁ is the same as or different from each other, and

If more than t42 is 2 and T ₄₂ are the same or different from each other,

If more than t43 is 2 T ₄₃ is the same as or different from each other, and

If more than t44 is 2, and T ₄₄ is the same as or different from each other,

If more than t45 is 2 T ₄₅ is the same as or different from each other, and

When t46 is 2 or more, T < ₄₆ >

If more than t47 is 2 and T ₄₇ are the same as or different from each other,

When t48 is 2 or more, T < ₄₈ > are the same or different from each other,

If more than t49 is 2 T ₄₉ is the same as or different from each other, and

If more than t50 is 2 and T ₅₀ are the same or different from each other,

If more than t51 is 2 T ₅₁ is the same as or different from each other, and

If more than t52 is 2 and T ₅₂ are the same or different from each other,

If more than t53 is 2 T ₅₃ is the same as or different from each other.

According to one embodiment of the present invention, Y ₁ and Y ₂ in the general formula (1) may be represented by the following general formula (2).

(2)

In Formula 2,

X ₁ To X < ₃ > are the same or different from each other, and each independently CR or N,

At least one of X ₁ to X ₃ is N,

R are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

Ar ₁ and Ar ₂ are the same or different and are each independently substituted or unsubstituted arylene,

L ₁₁ is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

v is an integer of 0 to 5, and when v is 2 or more, L < ₁₁ >

According to one embodiment of the present invention, Ar ₁ and Ar ₂ in Formula ₂ are substituted or unsubstituted phenyl groups; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted terphenyl group or a substituted or unsubstituted triphenylene group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ in Formula 2 may be selected from the following structures.

In the above structural formulas,

H ₁ to H ₄₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

h31, h31, h40 and h41 are the same or different and each independently an integer of 0 to 5, and each of h1, h3, h5, h7, h9, h13, h19, h22, h25, h26,

h21, h21, h23, h24, h37 and h42 are the same or different from each other and each independently represents an integer of 0 to 4, and h2, h4, h6, h8, h14, h17, h18,

h10, h11 and h39 are the same or different and each independently represents an integer of 0 to 7,

h12 is an integer of 0 to 9,

h15 and h32 are the same or different and each independently an integer of 0 to 6,

h16, h27, h30, h33, h36 and h43 are the same or different and each independently represents an integer of 0 to 3,

h38 is an integer of 0 to 8,

h1 is not less than 2 H ₁ is the same as or different from each other, and

when h ₂ is 2 or more, H ₂ are the same or different from each other,

h3 is not less than 2 H ₃ is the same as or different from each other, and

h4 is not less than 2 H _4, and is the same as or different from each other,

If more than the h5 2 H ₅ is the same as or different from each other, and

If more than this h6 2 H _6, and is the same as or different from each other,

h7 is not less than H 2, and ₇ are the same as or different from each other,

If more than h8 is H 2, and ₈ is the same as or different from each other,

If more than this h9 2 H ₉ are the same as or different from each other, and

If more than h10 2 and H ₁₀ are the same as or different from each other,

h11 is not less than 2 H ₁₁ are the same as or different from each other, and

h12 is not less than 2, and H ₁₂ are the same as or different from each other,

h13 is not less than 2 H ₁₃ are the same as or different from each other, and

h14 is not less than 2, and H ₁₄ are the same as or different from each other,

h15 is not less than 2 H ₁₅ are the same as or different from each other, and

h16 is not less than 2, and H ₁₆ are the same as or different from each other,

h17 is not less than 2 H ₁₇ are the same as or different from each other, and

h18 is not less than 2, and H ₁₈ are the same as or different from each other,

h19 is not less than 2 and H ₁₉ are the same as or different from each other,

h20 is not less than 2, and H ₂₀ are the same as or different from each other,

h21 is not less than 2 H ₂₁ are the same as or different from each other, and

h22 is not less than 2, and H ₂₂ are the same as or different from each other,

h23 is not less than 2 and H ₂₃ are the same as or different from each other,

h24 is not less than 2, and H ₂₄ are the same as or different from each other,

h25 is not less than 2 and H ₂₅ are the same as or different from each other,

h26 is not less than 2, and H ₂₆ are the same as or different from each other,

When h27 is 2 or more, H < ₂₇ > are the same or different from each other,

If more than h28 2 and H ₂₈ are the same as or different from each other,

h29 is not less than 2 and H ₂₉ are the same as or different from each other,

h30 is not less than 2, and H ₃₀ are the same as or different from each other,

When h ₃₁ is 2 or more, H ₃₁ are the same or different from each other,

If more than h32 2 and H ₃₂ are the same or different from each other,

h33 is not less than 2 H ₃₃ are the same as or different from each other, and

h36 is not less than 2, and H ₃₆ are the same as or different from each other,

When h37 is 2 or more, H < ₃₇ > are the same or different from each other,

h38 is not less than 2, and H ₃₈ are the same as or different from each other,

h39 is not less than 2 and H ₃₉ are the same as or different from each other,

h40 is not less than 2, and H ₄₀ are the same as or different from each other,

h41 is not less than 2 and H ₄₁ are the same as or different from each other,

h42 is not less than 2, and H ₄₂ are the same as or different from each other,

h43 is not less than 2 H ₄₃ is the same as or different from each other.

According to one embodiment of the present disclosure, Formula 2 may be selected from the following structures.

In the above structural formulas, A ₁ to A ₅₀ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

wherein a1, a2, a3, a4, a5, a7, a10, a13, a31, a35, a39, a41, a43, a45, a47, a48 and a50 are the same or different and each independently an integer of 0 to 4,

a6, a9, a12, a46 and a49 are the same or different and each independently represents an integer of 0 to 3,

a24, a32, a34, a36, a37, a40 and a44 are the same or different from each other and each independently Lt; / RTI > is an integer from 0 to 5,

a16 and a19 are the same or different and each independently represents an integer of 0 to 2,

a22, a25, a33, a38 and a42 are the same or different and each independently represents an integer of 0 or 1,

When a1 is 2 or more, A < _{1 >} are the same or different from each other,

If there is more than a2 is 2 A ₂ are the same or different from each other and,

If more than a3 is 2 A ₃ are the same as or different from each other, and

a4 is not less than 2, and A ₄ are the same as or different from each other,

If more than 2 A ₅ a5 are the same as or different from each other, and

a6 is 2 or more and A ₆ are the same as or different from each other,

If more than a7 is 2 and A ₇ are the same as or different from each other,

a8 is not less than 2, and A ₈ is the same as or different from each other,

a9 is 2 or more A ₉ is the same as or different from each other, and

If more than a10 is 2, and A ₁₀ is the same as or different from each other,

If more than a11 is 2 A ₁₁ is the same as or different from each other, and

If more than a12 is 2, and A ₁₂ is the same as or different from each other,

When a13 is 2 or more, _A13 are the same or different from each other,

If more than a14 is 2, and A ₁₄ is the same as or different from each other,

If more than a15 is 2 A ₁₅ is the same as or different from each other, and

If more than a16 is 2, and A ₁₆ is the same as or different from each other,

When a 17 is 2 or more, A ₁₇ are the same or different from each other,

If more than a18 is 2, and A ₁₈ is the same as or different from each other,

If more than a19 is 2 A ₁₉ is the same as or different from each other, and

If more than a20 is 2, and A ₂₀ is the same as or different from each other,

If more than a21 is 2 A ₂₁ is the same as or different from each other, and

If more than a22 is 2, and A ₂₂ is the same as or different from each other,

If more than a23 is 2, and A ₂₃ is the same as or different from each other,

If more than a24 is 2, and A ₂₄ is the same as or different from each other,

If more than a25 is 2, and A ₂₅ is the same as or different from each other,

If more than a26 is 2, and A ₂₆ is the same as or different from each other,

When a27 is 2 or more, A ₂₇ are the same or different from each other,

If more than a28 is 2, and A ₂₈ is the same as or different from each other,

When a29 is 2 or more, A ₂₉ are the same or different from each other,

If more than a30 is 2, and A ₃₀ is the same as or different from each other,

When a ₃₁ is 2 or more, A ₃₁ are the same or different from each other,

When a ₃₂ is 2 or more, A ₃₂ are the same or different from each other,

When a ₃₃ is 2 or more, A ₃₃ are the same or different from each other,

When a ₃₄ is 2 or more, A ₃₄ are the same or different from each other,

If more than a35 is 2 A ₃₅ is the same as or different from each other, and

If more than a36 is 2, and A ₃₆ is the same as or different from each other,

When a ₃₇ is 2 or more, A ₃₇ are the same or different from each other,

If more than a38 is 2, and A ₃₈ is the same as or different from each other,

When a ₃₉ is 2 or more, A ₃₉ are the same or different from each other,

When a ₄₀ is 2 or more, A ₄₀ are the same or different from each other.

According to one embodiment of the present invention, Y ₁ and Y ₂ in Formula 1 may be represented by Formula 3 below.

(3)

In Formula 3,

Y ₁₁ is CR ₁₁ R ₁₂ , NR ₁₃ , S or O,

R ₁₁ and R ₁₂ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,

R ₁₃ is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring, and L ₂₁ is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

G ₁ and G ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

g1 is an integer of 0 to 3, g2 is an integer of 0 to 4, v2 is an integer of 0 to 5,

When g1 is 2 or more, G < ₁ >

If more than two g2 and G ₂ are the same or different from each other,

When v2 is 2 or more, L < ₂₁ >

According to one embodiment of the present disclosure, Formula 3 may be selected from the following structures.

In the above structural formulas, B ₁ to B ₄₄ are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

C ₁ and C ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; B3, b5, b8, b11, b14, b17, b20, b22, b26, b30, b33, b35 or b35, b38, b40 and b43 are the same or different and are each independently an integer of 0 to 3,

b3 and b4 are the same or different and independently of one another an integer of 0 to 4, and each of b1, b2, b4, b6, b21, b23, b27 to b29, b31, b32, b34, b36, b37, b39,

b7, b10, b13, b16, b19, b24 and b25 are the same or different and independently of one another an integer of 0 to 5,

b9, b12, b15 and b18 are the same or different and each independently represents an integer of 0 to 6,

If more than b1 is 2, B ₁ is the same as or different from each other, and

When b ₂ is 2 or more, B ₂ are the same or different from each other,

If more than b3 are 2, B ₃ are the same as or different from each other, and

If more than b4 is 2, B ₄ are the same as or different from each other, and

If more than b5 is 2, B ₅ are the same as or different from each other, and

b6 is not less than 2, B ₆ is the same as or different from each other, and

If b7 is less than 2, B ₇ is the same as or different from each other, and

If more than b8 is 2, B ₈ are same as or different from each other, and

If more than b9 is 2, B ₉ are the same as or different from each other, and

If more than b10 is 2, B ₁₀ is the same as or different from each other, and

If more than b11 is 2, and B ₁₁ are the same as or different from each other,

If more than b12 is 2, B ₁₂ is the same as or different from each other, and

If more than b13 is 2, and B ₁₃ are the same as or different from each other,

If more than b14 is 2, B ₁₄ is the same as or different from each other, and

b15 not less than 2, and B ₁₅ are the same as or different from each other,

If more than b16 is 2, B ₁₆ is the same as or different from each other, and

If more than b17 is 2, B ₁₇ is the same as or different from each other, and

If more than b18 is 2, B ₁₈ is the same as or different from each other, and

b19 not less than 2, and B ₁₉ are the same as or different from each other,

If more than b20 is 2, B ₂₀ is the same as or different from each other, and

If more than b21 is 2, and B ₂₁ are the same as or different from each other,

If more than b22 is 2, B ₂₂ is the same as or different from each other, and

b23 not less than 2, and B ₂₃ are the same as or different from each other,

If more than b24 is 2, B ₂₄ is the same as or different from each other, and

If more than b25 is 2, and B ₂₅ are the same as or different from each other,

If more than b26 is 2, B ₂₆ is the same as or different from each other, and

b27 not less than 2, and B ₂₇ are the same as or different from each other,

If more than b28 is 2, B ₂₈ is the same as or different from each other, and

b29 not less than 2, and B ₂₉ are the same as or different from each other,

If more than b30 is 2, B ₃₀ is the same as or different from each other, and

b31 not less than 2, and B ₃₁ are the same as or different from each other,

If more than b32 is 2, B ₃₂ is the same as or different from each other, and

If more than b33 is 2, and B ₃₃ are the same as or different from each other,

If more than b34 is 2, B ₃₄ is the same as or different from each other, and

If more than b35 is 2, B ₃₅ is the same as or different from each other, and

If more than b36 is 2, B ₃₆ is the same as or different from each other, and

b37 not less than 2, and B ₃₇ are the same as or different from each other,

If more than b38 is 2, B ₃₈ is the same as or different from each other, and

If more than b39 is 2, and B ₃₉ are the same as or different from each other,

If more than b40 is 2, B ₄₀ is the same as or different from each other, and

b41 not less than 2, and B ₄₁ are the same as or different from each other,

If more than b42 is 2, B ₄₂ is the same as or different from each other, and

If more than b43 is 2, and B ₄₃ are the same as or different from each other,

If more than b44 is 2, B ₄₄ is the same as or different from each other.

According to one embodiment of the present invention, Y ₁ and Y ₂ in Formula 1 may be represented by Formula 4 below.

[Chemical Formula 4]

In Formula 4,

Y ₁₂ is CR ₁₅ or N,

R ₁₅ is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted heteroarylamine group,

L ₃₁ is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

G ₃ and G ₄ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

g3 and g4 are the same or different and each independently represents an integer of 0 to 4,

v3 is an integer of 0 to 5,

If more than g3 is 2, G ₃ are the same as or different from each other, and

If more than g4 is 2, G ₄ are the same or different from each other and,

When v3 is 2 or more, L ₃₁ are the same or different from each other.

According to one embodiment of the present disclosure, Formula 4 may be selected from the following structures.

In the above structural formulas, D ₁ to D ₁₉ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

d1 to d10, d13 to d15 and d17 to d19 are the same or different and each independently an integer of 0 to 4,

d11, d12 and d16 are the same or different and each independently represents an integer of 0 to 3,

When d1 is 2 or more, D < ₁ >

d2 is not less than 2 D ₂ is the same as or different from each other, and

If more than d3 is 2 D ₃ is the same as or different from each other, and

It not less than d4 is 2 and D ₄ is the same as or different from each other,

If more than d5 is 2 D ₅ is the same as or different from each other, and

If more than d6 is 2 and D ₆ is the same as or different from each other,

If more than d7 is 2 D ₇ is the same as or different from each other, and

d8 is D not less than 2, and ₈ is the same as or different from each other,

If more than d9 is 2 D ₉ are the same as or different from each other, and

If d10 is less than 2, and D ₁₀ is the same as or different from each other,

If d11 is less than 2 D ₁₁ is the same as or different from each other, and

If d12 is less than 2, and D ₁₂ is the same as or different from each other,

If d13 is less than 2 D ₁₃ is the same as or different from each other, and

If d14 is less than 2, and D ₁₄ is the same as or different from each other,

If d15 is less than 2 D ₁₅ is the same as or different from each other, and

If d16 is less than 2, and D ₁₆ is the same as or different from each other,

If d17 is less than 2 D ₁₇ is the same as or different from each other, and

If d18 is less than 2, and D ₁₈ is the same as or different from each other,

If d19 is less than 2 D ₁₉ it is the same as or different from each other.

According to one embodiment of the present invention, Y ₁ and Y ₂ in Formula 1 may be represented by Formula 5 below.

[Chemical Formula 5]

In Formula 5,

Z ₁ and Z ₂ are the same or different and each independently CR or N,

R is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,

L ₄₁ is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

n is an integer of 0 or 1,

P ₁ is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

When n is 0, r1 is an integer of 0 to 4,

When n is 1, r1 is an integer of 0 to 5,

v4 is an integer of 0 to 5,

When r1 is 2 or more, P < ₁ >

When v4 is 2 or more, L ₄₁ is equal to or different from each other.

According to one embodiment of the present disclosure, Formula 5 may be selected from the following structures.

In the above structural formulas, E ₁ to E ₁₅ are the same or different from each other, and are each independently equal to or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

e1 is an integer of 0 or 1,

e2, e4 to e6, e8, e9, e11 and e15 are the same or different and each independently an integer of 0 to 4,

e3, e13 and e14 are the same or different and each independently an integer of 0 to 3,

e7 and e12 are the same or different and each independently an integer of 0 to 5,

e10 is an integer of 0 to 7,

If there is more than a 2 e2 and E ₂ are the same or different from each other,

If more than e3 is 2 and E ₃ are same as or different from each other,

e4 not less than 2, and E ₄ are the same or different from each other,

If more than 2 e5 is E ₅ is the same as or different from each other, and

If more than e6 is 2 and E ₆ are the same or different from each other,

e7 is not less than 2, and E ₇ is the same as or different from each other,

If more than e8 is 2 and E ₈ are the same as or different from each other,

If more than e9 is 2 and E ₉ are the same as or different from each other,

If more than e10 is 2 and E ₁₀ are the same or different from each other,

If more than e11 is 2 and E ₁₁ is the same as or different from each other,

If more than e12 is 2 and E ₁₂ is the same as or different from each other,

If more than the e13 2 E ₁₃ is the same as or different from each other, and

If more than e14 is 2 and E ₁₄ is the same as or different from each other,

If more than the e15 2 E ₁₅ is the same as or different from each other.

According to one embodiment of the present invention, Y ₁ and Y ₂ in the general formula (1) may be represented by the following general formula (6).

[Chemical Formula 6]

In Formula 6,

P ₁₂ And P ₁₃ are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, Formula (6) may be selected from the following structures.

In the above structural formulas, F ₁ to F ₂₃ are the same or different from each other, and are each independently equal to or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring,

f15, f46, f49 and f49 are integers of 0 to 5, and f1, f2, f3, f5, f7, f8, f11, f12, f15, f16, f19, f20, f25, f30, f35, f38, f41,

f4 is an integer of 0 to 7,

f24, f27, f32, f42, f47 and f48 are integers of 0 to 4, and f6, f9, f10, f13, f14, f18, f21, f23,

f22, f26, f31, f36, f37 and f43 are integers of 0 to 3,

When f1 is 2 or more, F ₁ are the same or different from each other,

When f2 is 2 or more, F ₂ are the same or different from each other,

not less than f3 is 2 F ₃ are the same as or different from each other, and

If more than f4 are 2 F _4, and is the same as or different from each other,

If more than this f5 2 F ₅ is the same as or different from each other, and

When f6 is 2 or more, F < ₆ >

If more than this f7 2 F ₇ are the same as or different from each other, and

If more than this f8 2 F ₈ and is the same as or different from each other,

If more than f9 is 2 F ₉ it is the same as or different from each other, and

f10 is not less than 2 F ₁₀ is the same as or different from each other, and

f11 is not less than 2 F ₁₁ is the same as or different from each other, and

f12 is not less than 2, and F ₁₂ are the same as or different from each other,

f13 is not less than 2 F ₁₃ is the same as or different from each other, and

f14 is not less than 2, and F ₁₄ are the same as or different from each other,

f15 is not less than 2 F ₁₅ is the same as or different from each other, and

f16 is not less than 2, and F ₁₆ are the same as or different from each other,

f17 is not less than 2 F ₁₇ is the same as or different from each other, and

f18 is not less than 2, and F ₁₈ are the same as or different from each other,

f19 is not less than 2 F ₁₉ is the same as or different from each other, and

f20 is not less than 2, and F ₂₀ are the same as or different from each other,

f21 is not less than 2 F ₂₁ is the same as or different from each other, and

f22 is not less than 2, and F ₂₂ are the same as or different from each other,

f23 is not less than 2 F ₂₃ is the same as or different from each other, and

f24 is not less than 2, and F ₂₄ are the same as or different from each other,

f25 is not less than 2 F ₂₅ is the same as or different from each other, and

f26 is not less than 2, and F ₂₆ are the same as or different from each other,

When f27 is 2 or more, F ₂₇ are the same or different from each other,

f28 is not less than 2 F ₂₈ is the same as or different from each other, and

f29 is not less than 2 F ₂₉ is the same as or different from each other, and

f30 is not less than 2, and F ₃₀ are the same as or different from each other,

When f ₃₁ is 2 or more, F ₃₁ are the same or different from each other,

f32 is not less than 2, and F ₃₂ are the same as or different from each other,

f33 is not less than 2 F ₃₃ is the same as or different from each other, and

f34 is not less than 2, and F ₃₄ are the same as or different from each other,

f35 is not less than 2 F ₃₅ is the same as or different from each other, and

f36 is not less than 2, and F ₃₆ are the same as or different from each other,

f37 is not less than 2 F ₃₇ is the same as or different from each other, and

f38 is not less than 2, and F ₃₈ are the same as or different from each other,

f39 is not less than 2 F ₃₉ is the same as or different from each other, and

When f ₄₀ is 2 or more, F ₄₀ are the same or different from each other,

When F ₄₁ is 2 or more, F ₄₁ are the same or different from each other,

f42 is not less than 2, and F ₄₂ are the same as or different from each other,

f43 is not less than 2 F ₄₃ is the same as or different from each other, and

f44 is not less than 2, and F ₄₄ are the same as or different from each other,

f45 is not less than 2 F ₄₅ is the same as or different from each other, and

When f ₄₆ is 2 or more, F ₄₆ are the same or different from each other,

f47 is not less than 2 F ₄₇ is the same as or different from each other, and

f48 is not less than 2, and F ₄₈ are the same as or different from each other,

f49 is not less than 2 F ₄₉ is the same as or different from each other.

According to one embodiment of the present disclosure, S ₁ and S ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent substituents are bonded to each other to form a ring.

According to one embodiment of the present disclosure, S ₁ and S ₂ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, S ₁ and S ₂ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group having 1 to 20 carbon atoms.

According to one embodiment of the present disclosure, S ₁ and S ₂ are the same or different and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 6 carbon atoms.

According to one embodiment of the present disclosure, S ₁ and S ₂ are the same or different and each independently hydrogen; Or deuterium.

According to one embodiment of the present disclosure, S ₁ and S ₂ are hydrogen.

According to one embodiment of the present disclosure, L &_lt; ₁ > is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene.

According to one embodiment of the present disclosure, L &_lt; ₁ > is a direct bond; A monocyclic or bicyclic substituted or unsubstituted arylene; Or a monocyclic or bicyclic substituted or unsubstituted heteroarylene.

According to one embodiment of the present disclosure, L &_lt; ₁ > is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted biphenylene; A substituted or unsubstituted pyridinyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted quinazoline group.

According to one embodiment of the present disclosure, L &_lt; ₁ > is a direct bond; Phenylene; Biphenyllylene; Pyridylmethyl group; Triazine; Carbazole group; Or a quinazoline group.

According to one embodiment of the present disclosure, L ₂ is a direct bond; Or substituted or unsubstituted arylene.

According to one embodiment of the present disclosure, L ₂ is a direct bond; Or substituted or unsubstituted arylene having 6 to 30 carbon atoms.

According to one embodiment of the present disclosure, L ₂ is a direct bond; Or a substituted or unsubstituted arylene having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, L ₂ is a direct bond; Or a monocyclic or bicyclic substituted or unsubstituted arylene.

According to one embodiment of the present disclosure, L ₂ is a direct bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Or substituted or unsubstituted biphenyl rylene.

According to one embodiment of the present disclosure, L < ₂ > is substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Or substituted or unsubstituted biphenyl rylene.

According to one embodiment of the present disclosure, L ₂ is phenylene; Naphthylene; Or biphenyl rylene.

According to one embodiment of the present disclosure, Y ₁ and Y ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group.

According to one embodiment of the present disclosure, Y ₁ and Y ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Y ₁ and Y ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms; Or a substituted or unsubstituted amine group.

According to one embodiment of the present invention, Y ₁ and Y ₂ are the same or different and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, A substituted or unsubstituted thienyl group, a substituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted imidazole group, a substituted or unsubstituted thiazole group , A substituted or unsubstituted oxazole group, a substituted or unsubstituted oxadiazole group, a substituted or unsubstituted triazole group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted bipyridyl group, a substituted or unsubstituted Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted pyridopyrimidinyl group, A substituted or unsubstituted pyrazinopyranyl group, a substituted or unsubstituted pyrazinopyranyl group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted indole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoxazole group , A substituted or unsubstituted benzimidazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzocarbazole group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzothiophene group , A substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted phenanthroline, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group , A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenothiazinyl group, or a substituted or unsubstituted dibenzofuranyl group.

According to one embodiment of the present invention, Y ₁ and Y ₂ are the same or different from each other and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, A thiazole group, a thiazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a pyrimidyl group, a pyridyl group, A pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a benzofuranyl group, a phenanthroline group, a thianthrene group, a thiophene group, a benzoquinoline group, an indole group, a carbazole group, a benzooxazole group, a benzoimidazole group, A benzyloxy group, a benzyloxy group, a benzyloxy group, a benzyloxy group, Group, a benzothiazolyl group, a phenothiazine group, or possess dibenzo furanoid group.

According to one embodiment of the present invention, Y ₁ and Y ₂ are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofuranyl group; A substituted or unsubstituted benzothiophene group; Or a substituted or unsubstituted amine group.

According to one embodiment of the present disclosure, Y ₁ is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group.

According to one embodiment of the present disclosure, Y ₁ is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; Substituted or unsubstituted quinazoline group.

According to one embodiment of the present disclosure, Y ₂ is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group.

According to one embodiment of the present disclosure, Y ₂ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms; Or a substituted or unsubstituted amine group.

According to one embodiment of the present invention, Y ₂ is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzoimidazole group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuranyl group; Or a substituted or unsubstituted amine group.

According to one embodiment of the present invention, the compound of Formula 1 may be selected from the following structural formulas.

The compound represented by the above formula (1) can be produced based on the following production example. According to one embodiment, it can be prepared in the following manner.

[Reaction Scheme 1]

In the above Reaction Scheme 1,

A is a direct bond; Or substituted or unsubstituted arylene,

Y is a substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted amine group,

Hal is a halogen group,

A1 is a mono- or poly-substituted or unsubstituted arylene.

Also, the present invention provides an organic light emitting device comprising the compound represented by Formula 1.

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

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, a light emitting 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.

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

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

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

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

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

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

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

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, the compound may be included in the light emitting layer.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

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 include the compound of the present invention, i.e., the compound of 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.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of Formula 1, that is, the compound represented by Formula 1.

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, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic 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.

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

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

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

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

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

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

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

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

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

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing 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 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.

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

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< Example >

< Manufacturing example 1> Preparation of compounds 1-A-1 to 1-A-3

1) Synthesis of the following compound 1-A-1

[Compound 1-A-1]

The compound 2- (2-bromophenyl) -1H-indole (37.3 g, 0.5 mmol) and 4-chloroacetophenone (23.8 g, 1.0 mmol) were completely dissolved in 150 ml of dimethylsulfoxide in a nitrogen atmosphere, (1.0 mmol) were added, and copper (0.1 mmol) of copper (0.05 mmol) and ligand L-proline (0.1 mmol) were added and the mixture was heated with stirring. After cooling to room temperature, the solvent was distilled off and the solvent was removed. The residue was purified by column chromatography with petroleum / EA (20: 1) and recrystallized from n-hexane and ethanol to obtain the compound 1-A-1 (yield: 64%).

MS [M + H] < ⁺ > = 328.1

2) Synthesis of Compound 1-A-2 shown below

[Compound 1-A-2]

Compound 1-A-2 was prepared by the same method except for using 3-chloroacetophenone instead of 4-chloroacetophenone in the synthesis of Compound 1-A-1.

MS [M + H] < ⁺ > = 328.1

3) Synthesis of the following compound 1-A-3

[Compound 1-A-3]

Compound 1-A-3 was prepared by the same method except for using 2-chloroacetophenone instead of 4-chloroacetophenone in the synthesis of Compound 1-A-1.

MS [M + H] < ⁺ > = 328.1

< Manufacturing example 2> Preparation of compounds 1-B-1 to 1-B-3

1) Synthesis of Compound 1-B-1

[Compound 1-A-1] [Compound 1-B-1]

The compound 1-A-1 (98.9 mmol), bis (pinacolato) diboron (27.6 g, 108 mmol) and potassium acetate (29.1 g, 296 mmol) were mixed in a nitrogen atmosphere and heated to 100 ml with dioxane . Bis (dibenzylidineacetone) palladium (1.7 g, 2.94 mmol) and tricyclohexylphosphine (1.6 g, 5.9 mmol) were added under reflux and heated and stirred for 10 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was recrystallized from ethanol to obtain the above compound 1-B-1 (35 g, yield: 81%).

MS [M + H] < ⁺ > = 420.2

2) Synthesis of Compound 1-B-2 shown below

[Compound 1-A-2] [Compound 1-B-2]

Compound 1-B-2 was synthesized in the same manner as Compound 1-B-1 except that Compound 1-A-2 was used instead of Compound 1-A-1.

MS [M + H] < ⁺ > = 420.2

3) Synthesis of Compound 1-B-3 shown below

[Compound 1-A-3] [Compound 1-B-3]

Compound 1-B-3 was prepared by the same method except for using Compound 1-A-3 instead of Compound 1-A-1 in the synthesis of Compound 1-B-1.

MS [M + H] < ⁺ > = 420.2

< Manufacturing example 3> Preparation of Compound 2-1

1) Synthesis of the following compound 2-A

[Compound 1-B-1] [Compound 2-A]

The compound 1-B-1 and 2-chloro-4,6-diphenyl-1,3,5-triazine were added to dioxane, followed by the addition of a 2M aqueous potassium phosphate solution and tetrakistriphenylphosphinopalladium Followed by heating and stirring for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium phosphate solution was removed and the above white solid was filtered. The filtered white solid was recrystallized from tetrahydrofuran and ethanol to give the above compound 2-A (yield 90%).

MS [M + H] < ⁺ > = 525.1

2) Synthesis of the following compound 2-1

[Compound 2-A] [Compound 2-1]

After adding the compound 2-A and 4-bromobiphenyl to xylene, potassium-tertiary-butoxide was added, and the mixture was heated with stirring and bis [(tri-tertiary-butyl) phosphine] palladium (Pd [P t-Bu) ₃ ] ₂ ) And the mixture was heated with stirring for 4 hours. After lowering the temperature to room temperature and terminating the reaction, the white solid was filtered. The filtered white solid was recrystallized from chloroform, ethanol and ethyl acetate to give the above compound 2-1 (yield: 60%).

MS [M + H] < ⁺ > = 677.8

< Manufacturing example 4> Preparation of Compound 2-2

1) Synthesis of the following compound 2-B

[Compound 1-B-1] [Compound 2-B]

Except that 4- (biphenyl-4-yl) -2-chloroquinazoline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the synthesis of the compound 2-A Synthesis was conducted in the same manner to prepare Compound 2-B.

MS [M + H] < ⁺ > = 574.2

2) Synthesis of the following compound 2-2

[Compound 2-B] [Compound 2-2]

Compound 2-2 was synthesized by the same method except for using 4-iodobenzene instead of 4-bromobiphenyl in the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 650.3

< Manufacturing example 5> Preparation of Compound 2-3

1) Synthesis of the following compound 2-C

[Compound 1-B-1] [Compound 2-C]

Synthesis was carried out in the same manner except that 4-chloro-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the synthesis of the compound 2-A To give Compound 2-C.

2) Synthesis of Compound 2-3 below

[Compound 2-C] [Compound 2-3]

Compound 2-3 was synthesized in the same manner as Compound 2-1 except that 3-bromobiphenyl was used instead of 4-bromobiphenyl.

MS [M + H] < ⁺ > = 676.3

< Manufacturing example 6> Preparation of compound 2-4

1) Synthesis of the following compound 2-D

[Compound 1-B-1] [Compound 2-D]

Synthesis was carried out in the same manner except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-bromo-4,6-diphenylpyridine in the synthesis of the compound 2-A. To give compound 2-D.

MS [M + H] < ⁺ > = 523.2

2) Synthesis of the following compound 2-4

[Compound 2-D] [Compound 2-4]

Compound 2-4 was synthesized by the same method except for using 2- (4-bromophenyl) pyridine instead of 4-bromobiphenyl in the synthesis of Compound 2-1.

MS [M + H] < ⁺ > = 676.3

< Manufacturing example 7> Preparation of Compound 2-5

1) Synthesis of the following compound 2-E

[Compound 1-A-1] [Compound 2-E]

After adding the compound 1-A-1 and 8- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) quinoline to dioxane 2M aqueous potassium phosphate solution was added, tetrakistriphenylphosphinopalladium was added, and the mixture was heated and stirred for 10 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium phosphate solution was removed and the above white solid was filtered. The filtered white solid was recrystallized from tetrahydrofuran and ethanol to give the above compound 2-E (yield: 85%).

MS [M + H] < ⁺ > = 497.2

2) Synthesis of the following compound 2-5

[Compound 2-E] [Compound 2-5]

The compound 2-5 was synthesized by the same method as the compound 2-1.

MS [M + H] < ⁺ > = 649.3

< Manufacturing example 8> Preparation of Compound 2-6

1) Synthesis of the following compound 2-F

[Compound 1-A-1] [Compound 2-F]

In the synthesis of the above compound 2-E, 2-naphthaleneboronic acid (2-naphthalenesulfonic acid) was used in place of 8- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Was used to synthesize Compound 2-F.

MS [M + H] < ⁺ > = 420.2

2) Synthesis of the following compound 2-6

[Compound 2-F] [Compound 2-6]

Synthesis was conducted in the same manner as in the synthesis of the compound 2-5 except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 4- bromobiphenyl Compound 2-6 was prepared.

MS [M + H] < ⁺ > = 727.3

< Manufacturing example 9> Preparation of Compound 2-7

1) Synthesis of the following compound 2-G

[Compound 1-B-2] [Compound 2-G]

2-chloro-4-naphthyl-6-phenyl-1,3,5-triazine and dioxane were added to the above compound 1-B-2 and then a 2M potassium phosphate aqueous solution was added thereto to obtain tetrakistriphenylphosphine Pyridin-2-ylamine, and the mixture was heated and stirred for 12 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium phosphate solution was removed and the above white solid was filtered. The filtered white solid was recrystallized from tetrahydrofuran and ethanol to give the above compound 2-G (yield 85%).

MS [M + H] < ⁺ > = 575.2

2) Synthesis of the following compound 2-7

[Compound 2-G] [Compound 2-7]

The compound 2-7 was synthesized by the same method as the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 727.3

< Manufacturing example 10> Preparation of Compound 2-8

1) Synthesis of the following compound 2-H

[Compound 1-B-2] [Compound 2-H]

4-naphthyl-6-phenyl-1,3,5-triazine was used in the synthesis of the compound 2-G instead of 4 - ([ -2-phenylpyrimidine, the compound 2-H was prepared.

MS [M + H] < ⁺ > = 600.2

2) Synthesis of the following compound 2-8

[Compound 2-H] [Compound 2-8]

Compound 2-8 was synthesized by the same method except for using 4-iodobenzene instead of 4-bromobiphenyl in the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 675.3

< Manufacturing example 11> Preparation of Compound 2-9

1) Synthesis of the following compound 2-I

[Compound 1-B-2] [Compound 2-I]

In the synthesis of the compound 2-G, 4 '- (4-bromophenyl) -2,2': 6 ', 2' '- terpyridine was used to synthesize Compound 2-I.

MS [M + H] < ⁺ > = 601.2

2) Synthesis of the following compound 2-9

[Compound 2-I] [Compound 2-9]

Compound 2-9 was synthesized by the same method except for using 4-iodobenzene instead of 4-bromobiphenyl in the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 677.3

< Manufacturing example 12> Preparation of Compound 2-10

1) Synthesis of the following compound 2-J

[Compound 1-B-2] [Compound 2-J]

Chloro-4,6-di (biphenyl-4-yl) pyrimidine instead of 2-chloro-4-naphthyl- The compound 2-J was synthesized by the same method except that the compound 2-J was used.

MS [M + H] < ⁺ > = 676.3

2) Synthesis of the following compound 2-10

[Compound 2-J] [Compound 2-10]

Compound 2-10 was synthesized by the same method as Synthesis of Compound 2-1.

MS [M + H] < ⁺ > = 828.3

< Manufacturing example 13> Preparation of Compound 2-11

1) Synthesis of the following compound 2-K

[Compound 1-B-3] [Compound 2-K]

Was added to the above compound 1-B-3 and 2-chloro-4- [4- (1-naphthalenyl) phenyl] -quinazoline and dioxane, followed by the addition of a 2M aqueous potassium phosphate solution and tetrakis triphenylphosphine And the mixture was heated and stirred for 7 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium phosphate solution was removed and the above white solid was filtered. The filtered white solid was recrystallized from tetrahydrofuran and ethanol to give the above compound 2-K (yield 90%).

MS [M + H] < ⁺ > = 624.2

2) Synthesis of the following compound 2-11

[Compound 2-K] [Compound 2-11]

Compound 2-11 was synthesized in the same manner as Compound 2-1 except that 4-iodobenzene was used instead of 4-bromobiphenyl.

MS [M + H] < ⁺ > = 700.3

< Manufacturing example 14> Preparation of Compound 3-1

1) Synthesis of the following compound 3-A

[Compound 1-A-1] [Compound 3-A]

Was added to the above compound 1-A-1 and 9- (phenyl-9H-carbazol-3-yl) -boronic acid and dioxane, followed by the addition of a 2M aqueous potassium phosphate solution and adding tetrakistriphenylphosphinopalladium The mixture was heated and stirred for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium phosphate solution was removed and the above white solid was filtered. The filtered white solid was recrystallized from tetrahydrofuran and ethanol to give the above compound 3-A (yield 90%).

MS [M + H] < ⁺ > = 535.7

2) Synthesis of the following compound 3-1

[Compound 3-A] [Compound 3-1]

The compound 3-1 was synthesized by the same method as the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 687.3

< Manufacturing example 15> Preparation of Compound 3-2

1) Synthesis of the following compound 3-B

[Compound 1-A-1] [Compound 3-B]

Except that 9-phenyl-benzocarbazole-3-boronic acid was used instead of 9- (phenyl-9H-carbazol-3-yl) -boronic acid in the preparation of the above compound 3-A, 3-B.

MS [M + H] < ⁺ > = 585.2

2) Synthesis of the following compound 3-2

[Compound 3-B] [Compound 3-2]

Compound 3-2 was synthesized by the same method except for using 4-iodobenzene instead of 4-bromobiphenyl in the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 661.3

< Manufacturing example 16> Preparation of compound 3-3

1) Synthesis of the following compound 3-C

[Compound 1-A-1] [Compound 3-C]

Spiro [fluorene-9,8'-indolo [3, 2, 1, -de (3-fluoro-9H- ] Acridine-2-boronic acid, the compound 3-C was prepared.

MS [M + H] < ⁺ > = 560.2

2) Synthesis of the following compound 3-3

[Compound 3-C] [Compound 3-3]

Compound 3-3 was prepared by the same method except for using 4-iodobenzene instead of 4-bromobiphenyl in the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 636.2

< Manufacturing example 17> Preparation of Compound 3-4

1) Synthesis of the following compound 3-D

[Compound 1-A-1] [Compound 3-D]

Synthesis was conducted in the same manner as in the synthesis of the compound 3-A except that 9-phenanthrene-boronic acid was used instead of 9- (phenyl-9H-carbazol-3-yl) Respectively.

MS [M + H] < ⁺ > = 470.2

2) Synthesis of the following compound 3-4

[Compound 3-D] [Compound 3-4]

The compound 3-4 was synthesized by the same method as the compound 2-1.

MS [M + H] < ⁺ > = 622.2

< Manufacturing example 18> Preparation of Compound 3-5

1) Synthesis of the following compound 3-E

[Compound 1-A-2] [Compound 3-E]

Compound 3-A was synthesized in the same manner as Compound 3-A except that Compound 1-A-2 was used instead of Compound 1-A-1.

MS [M + H] < ⁺ > = 535.2

2) Synthesis of the following compound 3-5

[Compound 3-E] [Compound 3-5]

Compound 3-5 was synthesized in the same manner as Compound 2-1 except that 9- (phenyl-9H-carbazol-3-yl) -boronic acid was used instead of 4-bromobiphenyl.

MS [M + H] < ⁺ > = 776.3

< Manufacturing example 19> Preparation of Compound 3-6

1) Synthesis of the following compound 3-F

[Compound 1-A-1] [Compound 3-F]

Except that 9,9'-spiro [9H-fluorene] -2-boronic acid was used in place of 9- (phenyl-9H-carbazol-3-yl) -boronic acid in the synthesis of the above compound 3-E Were synthesized in the same way to give compound 3-F.

MS [M + H] < ⁺ > = 608.2

2) Synthesis of the following compound 3-6

[Compound 3-F] [Compound 3-6]

The compound 3-6 was synthesized by the same method as the compound 2-1.

MS [M + H] < ⁺ > = 760.3

< Manufacturing example 20> Preparation of compound 3-7

1) Synthesis of the following compound 3-G

[Compound 1-B-1] [Compound 3-G]

In the synthesis of the above compound 3-A, Compound 1-B-1 was used instead of Compound 1-A-1 and 2- (4-bromophenyl) ) Pyridine, the compound 3-G was prepared.

MS [M + H] < ⁺ > = 447.2

2) Synthesis of the following compound 3-7

[Compound 3-F] [Compound 3-7]

The compound 3-7 was synthesized by the same method as the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 599.2

< Manufacturing example 21> Preparation of Compound 3-8

1) Synthesis of the following compound 3-H

[Compound 1-B-1] [Compound 3-H]

Except that 2-bromo-9,10-dihydro-9,9-dimethyl-10-phenylacridine was used instead of 2- (4-bromophenyl) pyridine in the synthesis of the above compound 3-G The compound 3-H was synthesized by the same method.

MS [M + H] < ⁺ > = 577.3

2) Synthesis of the following compound 3-8

[Compound 3-H] [Compound 3-8]

Compound 3-8 was synthesized by the same method except for using 4-iodobenzene instead of 4-bromobiphenyl in the synthesis of the compound 2-1.

MS [M + H] < ⁺ > = 653.3

< Manufacturing example 22> Preparation of Compound 3-9

1) Synthesis of the following compound 3-I

[Compound 1-A-2] [Compound 3-I]

The compound 3-I was synthesized by the same method as the compound 3-E.

MS [M + H] < ⁺ > = 535.2

2) Synthesis of the following compound 3-9

[Compound 3-I] [Compound 3-9]

Compound 3-9 was synthesized in the same manner as Compound 2-1 except that 1-bromo-3,5-diphenylphenylboronic acid was used instead of 4-bromobiphenyl.

MS [M + H] < ⁺ > = 763.3

< Manufacturing example 23> Preparation of Compound 3-10

1) Synthesis of the following compound 3-J

[Compound 1-B-3] [Compound 3-J]

Except that 2- (3-bromophenyl) -5-phenylthiophene was used in the place of 2-chloro-4- [4- (1-naphthalenyl) phenyl] Were synthesized in the same manner to give Compound 3-J.

MS [M + H] < ⁺ > = 528.2

2) Synthesis of Compound 3-10 below

[Compound 3-J] [Compound 3-10]

Compound 3-10 was synthesized by the same method as Synthesis of Compound 2-1.

MS [M + H] < ⁺ > = 680.2

< Manufacturing example 24> Preparation of Compound 3-11

1) Synthesis of the following compound 3-K

[Compound 1-A-1] [Compound 3-K]

Compound 1-A-1, 4-bromobenzene and copper were added, followed by 2M potassium phosphate, and the mixture was heated and stirred for 12 hours. After the temperature was lowered to room temperature and the reaction was terminated, the mixture was filtered through silica, and the filtrate was collected by filtration with ethyl acetate and hexane (40: 1). The filtered white solid was recrystallized from ethyl acetate and hexane to give the above compound 3-K (yield 75%).

MS [M + H] < ⁺ > = 404.1

2) Synthesis of the following compound 3-11

[Compound 3-K] [Compound 3-11]

Compound 3-11 was synthesized by the same method except for using phenyltriphenylamine instead of 4-bromobiphenyl in the synthesis of Compound 2-1.

MS [M + H] < ⁺ > = 689.3

< Manufacturing example 25> Preparation of Compound 3-12

1) Synthesis of the following compound 3-12

[Compound 3-K] [Compound 3-12]

Compound 3-12 was synthesized in the same manner as in the synthesis of the compound 3-11 except that 4- (diben-4-ylimino-phenyl) boronic acid was used instead of phenyl terphenylamine.

MS [M + H] < ⁺ > = 765.3

< Example 1>

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 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.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

[LINE]

N, N-bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1- biphenyl) -4,4- diamine compound of the following structure was deposited on the hole injection layer to a thickness of 400 Å The hole transport layer was formed by thermal vacuum deposition.

Subsequently, a compound of the compound 2-1 prepared in Preparation Example 3 was vacuum deposited on the hole transport layer to a film thickness of 300 ANGSTROM with a dopant of Ir (ppy) _{3 at a} concentration of 10% by weight (dopant / compound) to form a light emitting layer.

The following electron transport material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer.

[Electron transport material]

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 Å on the electron injection and transport layer sequentially 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 < ^-8 > torr.

< Example 2>

The same experiment was conducted as in Example 1 except that the compound of Compound 2-2 was used instead of the compound of Compound 2-1.

< Example 3>

In the same manner as in Example 1 except that the compound of Compound 2-3 was used instead of the compound of Compound 2-1.

< Example 4>

In the same manner as in Example 1 except that the compound of Compound 2-4 was used in place of the compound of Compound 2-1.

< Example 5>

In the same manner as in Example 1 except that the compound of Compound 2-5 was used in place of the compound of Compound 2-1.

< Example 6>

In the same manner as in Example 1 except that the compound of Compound 2-6 was used in place of the compound of Compound 2-1.

< Example 7>

In the same manner as in Example 1 except that the compound of Compound 2-7 was used in place of the compound of Compound 2-1.

< Example 8>

In the same manner as in Example 1 except that the compound of Compound 2-8 was used in place of the compound of Compound 2-1.

< Example 9>

In the same manner as in Example 1 except that the compound of Compound 2-9 was used in place of the compound of Compound 2-1.

< Example 10>

In the same manner as in Example 1 except that the compound of Compound 2-10 was used in place of the compound of Compound 2-1.

< Experimental Example 11>

The same experiment was conducted as in Example 1 except that the compound of Compound 2-1 was used instead of the compound of Compound 2-1.

< Comparative Example 1>

The same experiment was conducted as in Example 1 except that the following H1 was used in place of the compound of Compound 2-1.

Table 1 shows the device results obtained by using the respective compounds as the light emitting layers in the above Examples 1 to 11 and Comparative Example 1.

number Host Dopant Doping concentration
(%) The driving voltage (V)
5000 cd / m ² Luminous efficiency
(Cd / A) Comparative Example 1 H1 Ir (ppy) ₃ 10 5.2 36 Example 1 Compound 2-1 Ir (ppy) ₃ 10 4.7 40 Example 2 Compound 2-2 Ir (ppy) ₃ 10 4.9 45 Example 3 Compound 2-3 Ir (ppy) ₃ 10 4.5 44 Example 4 Compound 2-4 Ir (ppy) ₃ 10 4.4 43 Example 5 Compound 2-5 Ir (ppy) ₃ 10 4.7 42 Example 6 Compound 2-6 Ir (ppy) ₃ 10 4.2 48 Example 7 Compound 2-7 Ir (ppy) ₃ 10 4.3 44 Example 8 Compound 2-8 Ir (ppy) ₃ 10 4.6 47 Example 9 Compound 2-9 Ir (ppy) ₃ 10 4.8 46 Example 10 Compound 2-10 Ir (ppy) ₃ 10 4.7 47 Example 11 Compound 2-11 Ir (ppy) ₃ 10 4.7 41

As can be seen from the above Table 1, Examples 1 to 11 show that the compound of the present invention can be used as a host of a green light emitting layer and can exhibit lower voltage characteristics and improved efficiency than Comparative Example 1. [

< Example 12>

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 was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. A compound 3-1 (400 Å) synthesized in the above Production Example 14, which is a hole transporting material, was vacuum-deposited thereon, and a host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. 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 lithium fluoride was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

&Lt; Example 13 >

The same experiment was conducted as in Example 12 except that Compound 3-2 was used instead of Compound 3-1 synthesized in Preparation Example 14 as a hole transport layer.

&Lt; Example 14 >

The same experiment was conducted as in Example 12 except that Compound 3-3 was used instead of Compound 3-1 synthesized in Preparation Example 14 as a hole transport layer.

&Lt; Example 15 >

The same experiment was conducted as in Example 12 except that Compound 3-4 was used instead of Compound 3-1 synthesized in Production Example 14 as the hole transport layer.

&Lt; Example 16 >

The same experiment was carried out as in Example 12 except that Compound 3-5 was used instead of Compound 3-1 synthesized in Production Example 14 as a hole transport layer.

&Lt; Example 17 >

In the same manner as in Example 12, except that Compound 3-6 was used instead of Compound 3-1 synthesized in Production Example 14 as the hole transport layer.

&Lt; Example 18 >

The same experiment was carried out as in Example 12 except that Compound 3-7 was used instead of Compound 3-1 synthesized in Production Example 14 as a hole transport layer.

&Lt; Example 19 >

The same experiment was conducted as in Example 12 except that Compound 3-8 was used instead of Compound 3-1 synthesized in Production Example 14 as a hole transport layer.

&Lt; Example 20 >

The same experiment was carried out as in Example 12 except that Compound 3-9 was used instead of Compound 3-1 synthesized in Production Example 14 as a hole transport layer.

&Lt; Example 21 >

The same experiment was conducted as in Example 12 except that Compound 3-10 was used instead of Compound 3-1 synthesized in Preparation Example 14 as a hole transport layer.

&Lt; Example 22 >

The same experiment was conducted as in Example 12 except that Compound 3-11 was used instead of Compound 3-1 synthesized in Preparation Example 14 as a hole transport layer.

&Lt; Example 23 >

The same experiment was conducted as in Example 12 except that Compound 3-12 was used instead of Compound 3-1 synthesized in Preparation Example 14 as a hole transport layer.

&Lt; Comparative Example 2 &

The same experiment was conducted as in Example 12 except that HT1 was used instead of Compound 3-1 synthesized in Preparation Example 14 as a hole transport layer.

Table 2 shows the results of the organic light emitting device manufactured using each compound as a hole transporting layer material as in Examples 12 to 23 and Comparative Example 2. [

Experimental Example
50 mA / cm 2 HTL material Voltage (V) Current efficiency (cd / A) Comparative Example 2 HT1 6.14 5.87 Example 12 Compound 3-1 6.25 6.46 Example 13 Compound 3-2 6.14 6.75 Example 14 Compound 3-3 6.28 6.62 Example 15 Compound 3-4 6.16 6.91 Example 16 Compound 3-5 6.23 7.12 Example 17 Compound 3-6 6.23 7.20 Example 18 Compound 3-7 6.15 7.02 Example 19 Compound 3-8 6.18 6.23 Example 20 Compound 3-9 6.20 6.77 Example 21 Compound 3-10 6.13 5.98 Example 22 Compound 3-11 6.22 7.11 Example 23 Compounds 3-12 6.19 6.50

The compound represented by Chemical Formula (1) according to the present invention can perform hole injection and hole transport in an organic electronic device including an organic light emitting device, and the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.

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

Claims

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

In Formula 1,
L ₁ is a direct bond; Phenylene; Biphenyllylene; A pyridinylene group; A pyrimidinyl group; Triazinylene group; A carbazolylene group; Or a quinazolylene group,
L ₂ is a direct bond; Phenylene; Naphthylene; Or biphenyl rylene,
Y ₁ is a phenyl group substituted or unsubstituted with a phenyl group or a naphthyl group; Naphthyl group; A dimethylfluorene group; An amine group substituted with a biphenyl group; A pyridine group substituted or unsubstituted with a phenyl group; A pyrimidine group substituted or unsubstituted with a phenyl group; A phenyl group, or a triazine group substituted or unsubstituted with a biphenyl group; Carbazole group; A quinoline group; Or a quinazoline group substituted or unsubstituted with a phenyl group,
Y ₂ is a phenyl group, a naphthyl group, or a phenyl group substituted or unsubstituted with a pyridine group; Naphthyl group; Anthracene group substituted or unsubstituted with a naphthyl group; Phenanthrene; A fluorene group substituted or unsubstituted with a methyl group or a phenyl group; A biphenyl group, or an amine group substituted or unsubstituted with a dimethylfluorene group; A carbazole group substituted or unsubstituted with a phenyl group; A quinazoline group substituted or unsubstituted with a phenyl group; A benzocarbazolyl group substituted or unsubstituted with a phenyl group; A benzimidazole group substituted or unsubstituted with a phenyl group; A pyrimidine group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group, a naphthyl group, or a phenanthrene group; A dibenzothiophene group; A dibenzofurane group;

; or

ego,
S ₁ and S ₂ are the same or different and are each independently hydrogen, or two or more adjacent substituents are bonded to each other to form a ring,
m1 and m2 are the same or different and each independently an integer of 0 to 10,
n1 and n2 are the same or different and each independently an integer of 1 to 10,
a is an integer of 0 to 4, b is an integer of 0 to 5,
When m1 is 2 or more, L < ₁ >
If more than n1 is 2 and Y ₁ are the same as or different from each other,
m2 or more is 2 L ₂ are the same as or different from each other, and
when n2 is 2 or more, Y < ₂ >
When a is 2 or more, S < ₁ >
when b is 2 or more, S ₂ are the same or different from each other.

delete

The compound according to claim 1, wherein the compound of formula (1) is selected from 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 and 10 Organic light emitting device.

[Claim 12] The organic light emitting device according to claim 11, wherein the organic compound layer containing the compound is a hole injection layer, a hole transport layer, or a hole injection and transport layer.

12. The organic light emitting device according to claim 11, wherein the organic compound layer containing the compound is an electron injection layer, an electron transport layer, or an electron injection and transport layer.

12. The organic light emitting device according to claim 11, wherein the organic compound layer including the compound is a light emitting layer.