KR101666751B1

KR101666751B1 - Hetero-cyclic compound and organic light emitting device comprising the same

Info

Publication number: KR101666751B1
Application number: KR1020150079955A
Authority: KR
Inventors: 허정오; 이동훈; 장분재; 강민영; 정원익; 허동욱; 한미연; 정민우
Original assignee: 주식회사 엘지화학
Priority date: 2014-06-05
Filing date: 2015-06-05
Publication date: 2016-10-14
Also published as: KR20150140241A

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 priority based on Korean Patent Application No. 10-2014-0068510, filed on Jun. 05, 2014, 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

Disclosed herein are novel heterocyclic compounds and organic light emitting devices comprising them.

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

[Chemical Formula 1]

In Formula 1,

A ₁ to A ₃ are the same or different and are 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 two adjacent or more substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

At least two of A ₁ to A ₃ are N,

When two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are substituted or unsubstituted aryl groups,

When A ₁ to A ₃ are both N, Ar ₁ is a substituted or unsubstituted aryl group, Ar ₂ is a phenyl group substituted or unsubstituted with an alkyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted 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 crecenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted heterocyclic group containing at least one of O and S atoms,

R ₁ and R 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 adjacent or more substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

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

Ar ₃ is a substituted or unsubstituted pyridyl group,

a is an integer of 0 to 4,

b is an integer of 0 to 3,

n is 2,

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

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

A plurality of L's are the same or different and a plurality of Ar ₃ 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 the compound of Chemical Formula 1 represented by Formula 1 above.

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 Si 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, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole 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 the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.

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

In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned 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.

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

(2)

In Formula 2,

The definitions of A ₁ to A ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₂ , a and b are the same as those of formula (1)

L ₁ and L ₂ are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

Ar ₁₁ and Ar ₁₂ are the same or different and are each independently a substituted or unsubstituted pyridyl group.

According to one embodiment of the present invention, Ar ₃ , Ar ₁₁ and Ar ₁₂ in the general formula (1) or (2) are the same or different and independently selected from the following structures.

U ₁ to U ₃ 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 two or more substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

u1 to u3 are the same or different and each independently an integer of 0 to 4,

When u1 is 2 or more, the plurality of U < _{1 > s} are the same or different from each other,

When u2 is 2 or more, plural U < ₂ > s are the same or different from each other,

When u < ₃ > is 2 or more, the plurality of U < ₃ >

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (3).

(3)

In Formula 3,

The definitions of L ₁ and L ₂ are as shown in formula (2)

T ₁ and T 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 adjacent two or more substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

t1 and t2 are the same or different and independently of one another an integer of 0 to 4,

When t1 is 2 or more, a plurality of T < _{1 > s} are the same or different from each other,

When t2 is 2 or more, a plurality of T < ₂ > s are equal to or different from each other.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (4) to (6).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 4 to 6,

The definitions of L ₁ and L ₂ are as shown in general formula (2).

According to one embodiment of the present invention, at least one of Ar ₁ and Ar ₂ in Formulas 1 to 6 may be selected from the following structures.

S ₁ to S ₃₆ 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 adjacent two or more substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

s1, s3, s17, s18, s20, s22, s24, s29, s30 and s36 are the same or different and are each independently an integer of 0 to 5,

wherein s2, s4, s7, s9, s10, s13, s15, s16, s21, s25, s26, s28, s32, s34 and s35 are the same or different and each independently an integer of 0 to 4,

s5, s11, s14, s19, s23, s27, s31 and s33 are the same or different and each independently an integer of 0 to 3,

s6 and s8 are the same or different and are each independently an integer of 0 to 6,

s12 is an integer of 0 to 2,

When s1 is 2 or more, S < ₁ > s are the same or different from each other,

when s2 is 2 or more, S ₂ are the same or different from each other,

When s3 is 2 or more, S < ₃ > are the same or different from each other,

when s4 is 2 or more, S ₄ are the same or different from each other,

If more than s5 2 and S ₅ are the same or different from each other,

If more than s6 is 2 S ₆ are the same as or different from each other, and

If more than s7 is 2 S, and ₇ are the same as or different from each other,

If s8 is greater than 2 S ₈ is the same as or different from each other, and

If more than s9 is 2 and S ₉ are the same as or different from each other,

If more than s10 the 2 S ₁₀ is the same as or different from each other, and

If more than s11 is 2 and S ₁₁ are the same as or different from each other,

If more than s12 the 2 S ₁₂ is the same as or different from each other, and

When s13 is 2 or more, _S13 are the same or different from each other,

S ₁₄ or more s14 is 2, and the same as or different from each other,

S ₁₅ or more s15 is 2 are the same as or different from each other,

If more than s16 the 2 S ₁₆ is the same as or different from each other, and

When s17 is 2 or more, _S17 are the same or different from each other,

If more than s18 is 2 and S ₁₈ are the same as or different from each other,

If more than s19 is 2 and S ₁₉ are the same as or different from each other,

If more than s20 is 2 and S ₂₀ are the same as or different from each other,

If more than s21 is 2 and S ₂₁ are the same as or different from each other,

If more than s22 the 2 S ₂₂ is the same as or different from each other, and

When s23 is 2 or more, S ₂₃ are the same or different from each other,

If more than s24 is 2 and S ₂₄ are the same as or different from each other,

If more than s25 is 2 and S ₂₅ are the same as or different from each other,

when s26 is 2 or more, S < ₂₆ > are the same or different from each other,

When s ₂₇ is 2 or more, S ₂₇ are the same or different from each other,

If more than s28 the 2 S ₂₈ is the same as or different from each other, and

When s29 is 2 or more, _S29 are the same or different from each other,

If more than s30 is 2 and S ₃₀ are the same as or different from each other,

When s ₃₁ is 2 or more, S ₃₁ are the same or different from each other,

If more than s32 the 2 S ₃₂ is the same as or different from each other, and

If more than s33 is 2 and S ₃₃ are the same as or different from each other,

If more than s34 the 2 S ₃₄ is the same as or different from each other, and

If more than s35 is 2 and S ₃₅ are the same as or different from each other,

If more than s36 the 2 S ₃₆ is the same as or different from each other.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (7) to (9).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas (7) to (9)

P ₁ to P ₃ 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 adjacent or more substituents may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

p1, p2 and p3 are the same or different and each independently represents an integer of 0 to 4,

When p1 is 2 or more, plural P < ₁ > s are the same or different from each other,

When p2 is 2 or more, plural P < ₂ &_gt; s are the same or different from each other,

When p3 is 2 or more, plural P < ₃ > s are the same or different from each other.

According to one embodiment of the present disclosure, A ₁ to A ₃ are the same or different from each other, and are each independently CR or N, and at least two of A ₁ to A ₃ are N.

According to one embodiment of the present disclosure, A ₁ through A ₃ are all N.

According to one embodiment of the present disclosure, R ₁ and R 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 adjacent two or more substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocycle.

According to one embodiment of the present disclosure, R ₁ and R ₂ are the same or different and each independently hydrogen; halogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, R ₁ and R ₂ are the same or different and each independently hydrogen; halogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 1 to 20 carbon atoms.

According to one embodiment of the present disclosure, R ₁ and R ₂ are the same or different and each independently hydrogen; halogen; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

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

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

According to one embodiment of the present disclosure, L is a direct bond; Substituted or unsubstituted arylene having 6 to 30 carbon atoms; Or substituted or unsubstituted heteroarylene containing at least one of N, O and S atoms.

According to one embodiment of the present disclosure, L is a direct bond; Substituted or unsubstituted arylene having 1 to 3 rings; Or substituted or unsubstituted heteroarylene of 1 to 3 rings.

According to one embodiment of the present disclosure, L 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 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 is monocyclic or bicyclic substituted or unsubstituted arylene.

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

According to one embodiment of the present disclosure, L is a direct bond; Or phenylene.

According to one embodiment of the present disclosure, L is phenylene.

According to one embodiment of the present disclosure, L is a direct bond.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene having 6 to 30 carbon atoms; Or substituted or unsubstituted heteroarylene containing at least one of N, O and S atoms.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene having 1 to 3 rings; Or substituted or unsubstituted heteroarylene of 1 to 3 rings.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently 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 ₁ and L ₂ are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently a monocyclic or bicyclic substituted or unsubstituted arylene.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently a direct bond; Or substituted or unsubstituted phenylene.

According to one embodiment of the present disclosure, L ₁ and L ₂ are the same or different and are each independently a direct bond; Or phenylene.

According to one embodiment of the present disclosure, L ₁ and L ₂ are phenylene.

According to one embodiment of the present disclosure, L ₁ and L ₂ are direct bonds.

According to one embodiment of the present invention, when all of A ₁ to A ₃ are N, Ar ₁ is a substituted or unsubstituted aryl group, Ar ₂ is a phenyl group substituted or unsubstituted with an alkyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted 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 crecenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted heterocyclic group containing at least one of O and S atoms.

According to one embodiment of the present invention, when A ₁ to A ₃ are both N, Ar ₁ is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted 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 crecenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted triphenylene group; Ar ₂ is a phenyl group substituted or unsubstituted with an alkyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted 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 crecenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted heterocyclic group containing at least one of O and S atoms.

According to one embodiment of the present invention, when A ₁ to A ₃ are both N, Ar ₁ is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted 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 crecenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted triphenylene group; Ar ₂ is a phenyl group substituted or unsubstituted with an alkyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted 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 crecenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted triphenylene group.

According to one embodiment of the present invention, when A ₁ to A ₃ are both N, Ar ₁ is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenanthryl group, Ar ₂ is an unsubstituted phenyl group; A phenyl group substituted with an alkyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenanthryl group.

According to one embodiment of the present invention, when all of A ₁ to A ₃ are N, Ar ₁ is a phenyl group substituted or unsubstituted with a methyl group or a t-butyl group; A biphenyl group; A terphenyl group; Naphthyl group; Anthracenyl group; A phenanthryl group; Pyrenyl; A perylenyl group; A crycenyl group; A fluorenyl group; Or a triphenylene group, Ar ₂ is a phenyl group substituted or unsubstituted with a methyl group or a t-butyl group; A terphenyl group; Naphthyl group; Anthracenyl group; A phenanthryl group; Pyrenyl; A perylenyl group; A crycenyl group; A fluorenyl group; Or a triphenylene group.

According to one embodiment of the present disclosure, when A ₁ to A ₃ are both N, Ar ₁ is a phenyl group; A phenyl group substituted with an alkyl group; A biphenyl group; Naphthyl group; Or a phenanthryl group, Ar ₂ is an unsubstituted phenyl group; A phenyl group substituted with an alkyl group; Naphthyl group; Or a phenanthryl group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are each a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are each a substituted or unsubstituted aryl group having 1 to 30 carbon atoms.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are each a substituted or unsubstituted aryl group having 1 to 20 carbon atoms.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are each a substituted or unsubstituted monocyclic or bicyclic aryl group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are each a substituted or unsubstituted monocyclic aryl group.

According to one embodiment of the present disclosure, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are each an aryl group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted 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 crecenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted triphenylene group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are the same or different and are each independently a phenyl group substituted or unsubstituted with an alkyl group; A biphenyl group; A terphenyl group; Naphthyl group; Anthracenyl group; A phenanthryl group; Pyrenyl; A perylenyl group; A crycenyl group; A fluorenyl group; Or a triphenylene group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenanthryl group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are the same or different and are each independently an unsubstituted phenyl group; A phenyl group substituted with an alkyl group; A biphenyl group; Naphthyl group; Or a phenanthryl group.

According to one embodiment of the present invention, when two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are the same or different and are each independently a phenyl group substituted or unsubstituted with a methyl group or a t-butyl group; A biphenyl group; Naphthyl group; Or a phenanthryl group.

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

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 compound 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 produced by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, that is, 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 LiO2 / 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 (Alq3); 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, perylene tetracarboxylic 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.

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

&Lt; Example 1 >

Synthesis Example 1 Synthesis of Compound Represented by Formula (1)

&Lt; EMI ID =

[Chemical Formula 1B]

[Chemical Formula 1B] < EMI ID =

(1) Preparation of the compound of formula (1A)

4-bromo-triazine (20g, 51.5mmol) and 3,5-phenylboronic acid (9.8g, 51.5mmol) and potassium carbonate _{(K 2 CO 3) (21.3g} , 155mmol) of tetrahydrofuran (THF) (300 mL), H ₂ O (100 mL) and heated to 90 ° C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (1.2g, 1.03mmol) was refluxed for 1 hour. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated and purified by column chromatography to obtain the compound of formula 1A (21 g, yield 90%).

MS: [M + H] < ⁺ > = 453

(2) Preparation of compound of formula 1B

Formula 1A (21g, 46.4mmol) and Bis (pinacolato) diboron (23.6g, 102mmol), PCy 3 (1.6g, 2.78mmol) and _{Pd (dba) 2 (1.6g,} 2.78mmol), KOAC (27.4g, 298mmol ) Was dissolved in dioxane (300 mL) and heated to 130 占 폚. Refluxed for 12 hours, cooled to room temperature and filtered. 1B (25 g, yield 85%) was obtained.

MS: [M + H] < ⁺ > = 637

(3) Preparation of formula (1)

(32.5 g, 235 mmol) and potassium carbonate (K ₂ CO ₃ ) (32.5 g, 235 mmol) were dissolved in tetrahydrofuran (THF) (300 mL), H ₂ O (100 ml) and heated to 90 < 0 > C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (1.8g, 1.56mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated and purified by column chromatography to obtain the compound of Formula 1 (19 g, yield 70%).

MS: [M + H] < ⁺ > = 691

Synthesis Example 2 Preparation of a compound represented by the formula (5)

[Chemical Formula 1C] [Chemical Formula 5]

(1) Preparation of formula 5

Except that Compound 1C (25 g, 35 mmol) was used instead of Compound 1B in the preparation of the compound of Formula 1 of Synthesis Example 1 to obtain Compound 5 (20 g, yield 75%).

MS: [M + H] < ⁺ > = 767

&Lt; Synthesis Example 3 > Preparation of a compound represented by the formula (12)

[Chemical Formula 1D] [Chemical Formula 12]

(1) Preparation of compound (12)

Except that Compound 1D (25 g, 34 mmol) was used instead of Compound 1B in the preparation of the compound of Formula 1 of Synthesis Example 1 to obtain Compound (12) (18 g, yield 67%).

MS: [M + H] < ⁺ > = 791

&Lt; Synthesis Example 4 > Preparation of a compound represented by the formula (16)

[Chemical Formula 1B] < EMI ID =

(1) Preparation of the compound of formula (16)

(17 g, yield: 81%) was obtained by the same method as in the preparation of Synthesis Example 1, except that the compound 4-bromopyridine was used instead of the compound 4-bromo-phenylpyridine .

MS: [M + H] < ⁺ > = 539

&Lt; Synthesis Example 5 > Preparation of the compound represented by the formula (19)

[Chemical Formula 1C] [Chemical Formula 19]

(1) Preparation of compound (19)

(16 g, yield: 74%) was prepared in the same manner as in the preparation of the compound of the formula 2, except that the compound 4-bromo-phenylpyridine was used instead of the compound 4-bromopyridine .

MS: [M + H] < ⁺ > = 615

&Lt; Synthesis Example 6 > Preparation of the compound represented by the formula (31)

[Chemical Formula 1B] < EMI ID =

(1) Preparation of compound (31)

Except that the compound 4-bromopyridine and 4-bromo-phenylpyridine were used in an amount of 1 equivalent each instead of 2 equivalents of 4-bromo-phenylpyridine in the preparation of the compound of Formula 1 of Synthesis Example 1 To obtain the compound of Formula 31 (21 g, yield 87%).

MS: [M + H] < ⁺ > = 615

Synthesis Example 7 Synthesis of Compound Represented by Formula 88

[Chemical Formula 2B]

(1) Preparation of compound of formula 88

Except that Compound 2B (25 g, 39.3 mmol) was used instead of Compound 1B in the preparation of the compound of Formula 1 of Synthesis Example 1 to obtain Compound 88 (21 g, yield 77%).

MS: [M + H] < ⁺ > = 690

&Lt; Synthetic Example 8 > - Preparation of the compound represented by the formula (175)

[Formula 3B]

(1) Preparation of compound (175)

175 g (19 g, yield 70%) was obtained by the same method except that Compound 3B (25 g, 39.3 mmol) was used instead of Compound 1B in Synthesis Example 1.

MS: [M + H] < ⁺ > = 690

&Lt; Example 1 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1000 Å was immersed in distilled water containing a dispersant 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. HT1 (400 Å), 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. (1) and LiQ (Lithium Quinolate) prepared in Preparation Example 1 were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode. Thereby preparing an organic light emitting device.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10- 2 ⁷ To 5 x 10 < ^-6 > torr, thereby fabricating an organic light emitting device.

[Hexanitrile hexaazatriphenylgylene] [LiQ]

[HT1]

[H1]

[D1]

&Lt; Example 2 >

The same experiment was carried out except that the electron transport layer in Example 1 was replaced with the electron transport layer 5 in place of the electron transport layer.

&Lt; Example 3 >

The same experiment was carried out except that the electron transport layer in Example 1 was replaced with the electron transport layer represented by Chemical Formula 12 instead of Chemical Formula 1.

The same experiment was carried out except that the electron transport layer in Example 1 was replaced with the electron transport layer in accordance with Formula 16 instead of Formula 1.

&Lt; Example 5 >

The same experiment was carried out except that the electron transport layer in Example 1 was replaced with the electron transport layer (19) instead of the electron transport layer (1).

&Lt; Example 6 >

The same experiment was carried out except that the electron transport layer in Example 1 was replaced with the electron transport layer 31 in place of the electron transport layer.

&Lt; Example 7 >

The same experiment was conducted except that the electron transport layer in Example 1 was replaced with the electron transport layer represented by Formula 88 instead of Formula 1.

&Lt; Example 8 >

The same experiment was conducted except that the electron transport layer in Example 1 was replaced with the electron transport layer represented by Chemical Formula 175 instead of Chemical Formula 1.

&Lt; Comparative Example 1 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of ET1 was used in place of the compound of Formula 1 in Experimental Example 1.

[ET1]

&Lt; Comparative Example 2 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of ET2 was used in place of the compound of Formula 1 in Experimental Example 1.

[ET2]

&Lt; Comparative Example 3 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound of ET3 was used in place of the compound of Formula 1 in Experimental Example 1.

[ET3]

&Lt; Comparative Example 4 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound of ET4 was used instead of the compound of Formula 1 in Experimental Example 1.

[ET4]

Table 1 shows the results of experiments of the organic light emitting devices manufactured using the respective compounds as electron transport layer materials as in Examples 1 to 8 and Comparative Examples 1 to 4.

Experimental Example
10 mA / cm 2 compound Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) Example 1 Formula 1 3.92 5.37 (0.137, 0.124) Example 2 Formula 5 3.99 5.42 (0.139, 0.124) Example 3 Formula 12 4.01 5.47 (0.138, 0.127) Example 4 Formula 16 3.90 5.34 (0.138, 0.129) Example 5 Formula 19 3.75 5.24 (0.137, 0.162) Example 6 31 3.88 5.30 (0.137, 0.124) Example 7 88 3.98 5.33 (0.137, 0.162) Example 8 Formula 175 4.10 5.55 (0.137, 0.162) Comparative Example 1 ET1 4.01 5.15 (0.140, 0.129) Comparative Example 2 ET2 4.01 5.13 (0.140, 0.129) Comparative Example 3 ET3 4.21 5.02 (0.139, 0.129) Comparative Example 4 ET4 3.95 4.7 (0.137, 0.162)

As shown in Table 1, when comparing the organic light emitting device manufactured using the compound according to one embodiment of the present application as the electron transport layer material and the conventional material, it was found that the excellent characteristics in terms of efficiency, driving voltage and stability . &Lt; / RTI >

For example, a comparison of Experimental Examples 1 to 3 and Comparative Example 3 in Table 1 reveals that Comparative Example 3 using a compound in which a ring is a triazine group containing A ₁ to A ₃ and Ar ₁ and Ar ₂ are biphenyl groups at the same time 3 < tb >< tb >< SEP > This is because, when Ar ₁ and Ar ₂ are both biphenyl groups, the LUMO orbit is widely distributed and the LUMO energy level is excessively low, so that a barrier against the LUMO energy level of the light emitting layer is formed, thereby deteriorating the electron transporting and injecting ability.

Therefore, the organic light emitting device using the compound according to one embodiment of the present application can exhibit excellent characteristics in terms of efficiency, driving voltage, and stability.

While the present invention has been described with reference to the preferred embodiments (the electron transport layer) of the present application, the present application is not limited thereto and can be variously modified within the scope of the claims and the detailed description of the invention, .

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,
A ₁ to A ₃ are the same or different and are each independently CR or N,
R is hydrogen or deuterium,
At least two of A ₁ to A ₃ are N,
When two of A ₁ to A ₃ are N, Ar ₁ and Ar ₂ are aryl groups having 6 to 60 carbon atoms,
When all of A ₁ to A ₃ are N, Ar ₁ is an aryl group having 6 to 60 carbon atoms, Ar ₂ is a phenyl group or a naphthyl group,
R ₁ and R ₂ are the same or different and each independently hydrogen or deuterium,
L is a direct bond or arylene having 6 to 60 carbon atoms,
Ar ₃ is a pyridyl group,
a is an integer of 0 to 4,
b is an integer of 0 to 3,
n is 2,
when a is 2 or more, plural R < ₁ > s are the same or different from each other,
when b is 2 or more, plural R ₂ are the same or different from each other,
A plurality of L's are the same or different and a plurality of Ar ₃ are the same or different from each other.

delete

3. The compound according to claim 1, wherein Ar < ₃ > are the same or different from each other and each independently selected from the following structures:

U ₁ to U ₃ are hydrogen,
u1 to u3 are the same or different from each other and each independently an integer of 0 to 4;

The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 3:
(3)

In Formula 3,
The definitions of A ₁ to A ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₂ , a and b are the same as those of formula (1)
L ₁ and L ₂ are the same or different and each independently is a direct bond or arylene having 6 to 60 carbon atoms,
T ₁ and T ₂ are the same or different and each independently hydrogen or deuterium,
t1 and t2 are the same or different and independently of one another an integer of 0 to 4,
When t1 is 2 or more, a plurality of T < _{1 > s} are the same or different from each other,
When t2 is 2 or more, a plurality of T < ₂ > s are equal to or different from each other.

The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (4) to (6):
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 4 to 6,
The definitions of A ₁ to A ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₂ , a and b are the same as those of formula (1)
L ₁ and L ₂ are the same or different from each other, and each independently is a direct bond or arylene having 6 to 60 carbon atoms.

The compound according to claim 1, wherein at least one of Ar ₁ and Ar ₂ is selected from the following structures:

S ₁ to S ₈ are the same or different and each independently hydrogen or deuterium,
s1 and s3 are the same or different and each independently an integer of 0 to 5,
s2, s4 and s7 are the same or different and each independently an integer of 0 to 4,
s5 is an integer of 0 to 3,
s6 and s8 are the same or different and are each independently an integer of 0 to 6,
When s1 is 2 or more, plural S < ₁ > s are the same or different from each other,
when s2 is 2 or more, plural S < ₂ > s are the same or different from each other,
When s3 is 2 or more, plural S < ₃ > s are the same or different from each other,
When s4 is 2 or more, the plural S < ₄ > s are the same or different from each other,
When s5 is 2 or more, the plural S < ₅ > s are the same or different from each other,
When s6 is 2 or more, the plural S < ₆ > s are the same or different from each other,
When s7 is 2 or more, plural S < ₇ > s are the same or different from each other,
When s8 is 2 or more, the plural S < ₈ > s are the same or different from each other.

The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (7) to (9)
(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas (7) to (9)
The definitions of A ₁ to A ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₂ , a and b are the same as those of formula (1)
P ₁ to P ₃ are the same or different and are each independently hydrogen or deuterium,
p1, p2 and p3 are the same or different and each independently represents an integer of 0 to 4,
When p1 is 2 or more, plural P < ₁ > s are the same or different from each other,
When p2 is 2 or more, plural P < ₂ &_gt; s are the same or different from each other,
When p3 is 2 or more, plural P < ₃ > are the same or different from each other,
T ₁ and T ₂ are hydrogen,
t1 and t2 are the same or different from each other, and each independently an integer of 0 to 4;

The compound of 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 3 to 8 Lt; / RTI >

[Claim 9] The organic light emitting device according to claim 9, wherein the organic compound layer containing the compound is a hole injection layer, a hole transport layer, or a hole injection and transport layer.

The organic light emitting device according to claim 9, wherein the organic compound layer containing the compound is an electron injection layer, an electron transport layer, or an electron injection and transport layer.

The organic light emitting device according to claim 9, wherein the organic compound layer containing the compound is a light emitting layer.