KR20160126792A - Multicyclic compound including nitrogen and organic light emitting device using the same - Google Patents

Multicyclic compound including nitrogen and organic light emitting device using the same Download PDF

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KR20160126792A
KR20160126792A KR1020150058320A KR20150058320A KR20160126792A KR 20160126792 A KR20160126792 A KR 20160126792A KR 1020150058320 A KR1020150058320 A KR 1020150058320A KR 20150058320 A KR20150058320 A KR 20150058320A KR 20160126792 A KR20160126792 A KR 20160126792A
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KR101953175B1 (en
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홍완표
이호용
권혁준
김민준
김공겸
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주식회사 엘지화학
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds

Abstract

Provided are a polycyclic compound including nitrogen, represented by chemical formula 1 and an organic light emitting device using the same. According to an embodiment of the present invention, the compound can improve efficiency of an organic light emitting device, low driving voltage and/or lifespan properties.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrogen-containing polycyclic compound and an organic light-emitting device using the same. BACKGROUND ART [0002]

The present specification relates to nitrogen-containing polycyclic compounds and organic light-emitting devices using 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

In the present specification, nitrogen-containing polycyclic compounds and organic light-emitting devices using the same are described.

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

[Chemical Formula 1]

Figure pat00001

In Formula 1,

Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

X1 to X3 are the same or different and are each independently C-CN, N or C (R4)

At least one of X1 to X3 is C-CN,

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

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

Y is N (R5), O, C (R6) (R7), S or Si (R8) (R9)

R5 to R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

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

b is an integer of 0 to 2,

p is an integer of 1 to 5,

When a, b, and p are each 2 or more, the structures in parentheses 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. The compounds described herein can be used as hole injecting, hole transporting, hole injecting and transporting, luminescence, electron transporting, or electron injecting materials. In particular, the compound of the present invention can be used as a light emitting layer of an organic light emitting device by using it as a host material together with a phosphorescent dopant. In addition, the compound of the present invention can be used as an electron injecting layer and / or an electron transporting layer between a cathode and a light emitting layer. Further, the compound of the present invention can be used as a hole blocking layer between the light emitting layer, the electron injecting layer and the electron transporting layer.

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.
Fig. 3 is a diagram showing LC-Mass data as confirmation data of the synthesis of the compound P used in Example 6. Fig.
4 is a graph showing LC-Mass data as synthesis confirmation data as synthesis confirmation data of compound W used in Example 8. Fig.
FIG. 5 is a graph showing LC-Mass data as a confirmation data of the synthesis of the compound C according to Production Example 1. FIG.

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).

In the present specification,

Figure pat00002
Quot; means a bond connected to another substituent.

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; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

Figure pat00003

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

Figure pat00004

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

Figure pat00005

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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,

Figure pat00006
,
Figure pat00007
,
Figure pat00008
And
Figure pat00009
And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, S, Se 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 aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, the alkylaryl group and the arylamine group, Can be applied.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group can be applied to the alkyl group described above.

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

In the present specification, the alkenyl group in the aralkenyl group can be applied to the description of the alkenyl group described above.

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

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

In the present specification, the term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; Or a condensed ring thereof.

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom.

As used herein, an aromatic heterocyclic ring means an aromatic ring containing at least one heteroatom.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

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

(2)

Figure pat00010

In Formula 2,

The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, R5, a, b, c and p are as shown in Formula (1).

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

(3)

Figure pat00011

[Chemical Formula 4]

Figure pat00012

[Chemical Formula 5]

Figure pat00013

[Chemical Formula 6]

Figure pat00014

In the above formulas 3 to 6,

The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, R6 to R9, a, b, c and p are as shown in formula (1).

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)

Figure pat00015

[Chemical Formula 8]

Figure pat00016

[Chemical Formula 9]

Figure pat00017

In the above formulas (7) to (9)

The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, Y, a, b, c and p are as shown in formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (10) to (12).

[Chemical formula 10]

Figure pat00018

(11)

Figure pat00019

[Chemical Formula 12]

Figure pat00020

In Formulas 10 to 12,

The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, Y, a, b, c and p are as shown in formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (13) or (14).

[Chemical Formula 13]

Figure pat00021

[Chemical Formula 14]

Figure pat00022

In the above formulas (13) and (14)

The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, Y, a, b, c and p are as shown in formula (1).

According to one embodiment of the present disclosure,

Figure pat00023
Moiety can be selected from the following structural formulas.

Figure pat00024
Figure pat00025
Figure pat00026

Figure pat00027
Figure pat00028
Figure pat00029

Figure pat00030

In the above formula,

The definitions of X1 to X3 are the same as those in formula (1).

According to one embodiment of the present disclosure, Ar1 and Ar2 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 hydrocarbon ring or a heterocyclic ring by bonding with adjacent substituents.

According to one embodiment of the present disclosure, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and are each independently a monocyclic or bicyclic substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

According to one embodiment of the present disclosure, Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; Or a biphenyl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenyl group, Ar2 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

According to one embodiment of the present disclosure, Ar1 is a phenyl group, Ar2 is a phenyl group; Or a biphenyl group.

According to one embodiment of the present disclosure, X1 to X3 are the same or different from each other, and each independently is C-CN, N or CR4, and at least one of X1 to X3 is C-CN.

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

According to one embodiment of the present disclosure, L is a direct bond; Or may be any one selected from the following structures.

Figure pat00031

The structures include deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group, which may be substituted or unsubstituted.

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 a direct bond.

According to one embodiment of the present disclosure, R1 to R3 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 may be bonded to adjacent substituents to form a substituted or unsubstituted hydrocarbon ring or a heterocycle.

According to one embodiment of the present disclosure, R1 to R3 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 aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, R1 to R3 are the same or different from each other and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

According to one embodiment of the present disclosure, R1 to R3 are the same or different and each independently hydrogen.

According to one embodiment of the present disclosure, Y is N (R5).

According to one embodiment of the present disclosure, R5 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, R5 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing N.

According to one embodiment of the present disclosure, R5 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted monocyclic heterocyclic group containing N.

According to one embodiment of the present invention, R5 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 pyridyl group; A substituted or unsubstituted pyrimidyl; Or a substituted or unsubstituted triazine group.

According to one embodiment of the present invention, R5 is an unsubstituted phenyl group; a phenyl group substituted with a tert-butyl group; A phenyl group substituted with an alkoxy group; A phenyl group substituted with a carbazole group; A biphenyl group; A terphenyl group; Naphthyl group; A pyridyl group; Pyrimidyl; Unsubstituted triazine; Or a triazine group substituted with a phenyl group.

According to one embodiment of the present disclosure, Y is C (R6) (R7).

According to one embodiment of the present invention, R6 and R7 are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, R6 and R7 are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present disclosure, R6 and R7 are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, R6 and R7 are the same or different and are each independently a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, R6 and R7 are the same or different and are each independently a substituted or unsubstituted alkyl group.

According to one embodiment of the present invention, R6 and R7 are the same or different from each other and are each independently a methyl group; Or a substituted or unsubstituted phenyl group, or combine with each other to form a hydrocarbon ring.

According to one embodiment of the present disclosure, R6 and R7 are alkyl groups.

According to one embodiment of the present invention, R6 and R7 are methyl groups.

According to one embodiment of the present disclosure, R6 and R7 are phenyl groups.

According to one embodiment of the present disclosure, Y is O.

According to one embodiment of the present disclosure, Y is S.

According to one embodiment of the present disclosure, Y is Si (R8) (R9).

According to one embodiment of the present invention, R8 and R9 are the same or different from each other and are each independently a methyl group; Or a phenyl group.

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

Figure pat00032

Figure pat00033

Figure pat00034

Figure pat00035

Figure pat00036

Figure pat00037

Figure pat00038

Figure pat00039

Figure pat00040

Figure pat00041

Figure pat00042

Figure pat00043

Figure pat00044

Figure pat00045

Figure pat00046

Figure pat00047

Figure pat00048

Figure pat00049

Figure pat00050

Figure pat00051

Figure pat00052

Figure pat00053

Figure pat00054

Figure pat00055

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Figure pat00060

Figure pat00061

Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

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 same manner as the following Reaction Schemes 1 to 7. For example, the structure of the compound comprising an aromatic hydrocarbon group substituted with a cyano group in the above formula (1) Commun. 2001, 31, 3497 and Tetrahedron 2010, 66, 7418, the following reaction formula can be used.

Figure pat00067

The structure of the compound consisting of the aromatic heterocyclic group substituted with the cyano group in the above formula (1) is described in J. Heterocycl. Chem. 1987, 24, 709 and Syn. Commun. 2009, 39, 1055, it can be synthesized by the following reaction formula.

Figure pat00068

The compound represented by the formula (1) can be synthesized by introducing various carbazole corresponding to the aromatic hydrocarbon group or the heterocyclic group substituted with the cyano group obtained by the above-mentioned Reaction formula 1-5 by the method shown below.

For example, when L1 in the general formula (1) is substituted or unsubstituted arylene or substituted or unsubstituted heteroarylene, Rev. 1995, 95, 2457], the following reaction scheme 6 can be used.

Figure pat00069

When L1 in the general formula (1) is a direct bond, an indolecarbazole (Y═N) or benzofuranylcarbazole (Y═O) or benzothiophenecarbazole (Y═S) or indenylcarbazole Y = CR6R7) or hydrogen bonded to the nitrogen of benzo-silocarbazole (Y = CR8R9) is replaced with a corresponding substituent by a coupling reaction such as, for example, the Ullmann reaction. Can be manufactured.

Figure pat00070

In the above reaction schemes,

The substituents are as defined in the above formula (1).

Also, the present invention provides an organic light emitting device comprising the compound represented by Formula 1. The present inventors have found that the use of a compound containing a substituted or unsubstituted hydrocarbon ring having -CN group or a substituted or unsubstituted aromatic heterocyclic group in organic light emitting devices remarkably improves characteristics particularly relating to operating voltage, lifetime and efficiency I found out. On the other hand, the triazine derivatives disclosed in Korean Patent Registration No. 10-0955993 still need improvement in terms of the efficiency and lifetime of the device as well as the operating voltage when the phosphorescent dopant is used as a host material.

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 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.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; Wherein at least one of the two or more organic layers includes the heterocyclic compound. 2. The organic electroluminescent device according to claim 1, wherein the organic compound layer comprises at least one organic compound. In one embodiment, the two or more organic layers may be selected from the group consisting of an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and an electron injecting layer, and a hole blocking layer.

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the heterocyclic compound. Specifically, in one embodiment of the present specification, the heterocyclic compound may be contained in one of the two or more electron transporting layers, or may be included in each of two or more electron transporting layers.

In one embodiment of the present invention, when the heterocyclic compound is contained in each of the two or more electron transporting layers, the materials other than the heterocyclic compound may be the same or different from each other.

 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 (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 Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has 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.

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.

< Manufacturing example >

< Manufacturing example  1>

Figure pat00071

4,6-diphenyl-2-pyrimidinamine (9.89 g, 40 mmol) was dissolved in acetonitrile (CH3CN) (100 mL) and N-bromosuccinimide (N-bromosuccinimide) (7.1 g, 40 mmol). After 8 hours, distilled water was added to terminate the reaction and extracted twice with 400 mL of ethyl acetate. The organic layer was washed with water and aqueous sodium hydrogen carbonate, dried and then the obtained organic layer over anhydrous sodium sulfate (MgSO 4). After filtration, the solvent was distilled off under reduced pressure to obtain 10.1 g (31 mmol, 78%) of white solid A.

Next, 5.37 g (60 mmol) of copper cyanide (CuCN) was added to 9.79 g (30 mmol) of the white powder obtained above under argon, and Nmethyl-2-pyrrolidinone mL) was added and stirred. Thereafter, the mixture was heated to 180 ° C and stirred for 24 hours. After cooling to room temperature, ammonia water (200 mL) was added and stirred, and crystals formed were collected by filtration. The filtrate was reslurried twice with 100 mL of water, and then reslurried with 100 mL of ethanol. The obtained crystals were dried under reduced pressure using a vacuum drier to obtain 6.0 g (22 mmol, 73%) of white crystals.

Next, 80 ml of glacial acetic acid, 20 ml of sulfuric acid and 20 ml of distilled water were added to 6.0 g (22 mmol) of the white powder obtained above, and the mixture was heated. After that, the solution was cooled to 3-4 ° C, 20 ml of a 1.64 M sodium nitrite solution was added, and the mixture was stirred for 30 minutes. The solution of hydrochloric acid (HCl) 16 m L with a copper chloride (CuCl 2) 3.28 g (24.4 mmol) dissolved was slowly added dropwise at 3-4 ° C. The mixture was heated to 45 ° C, stirred for 30 minutes, heated to 80 ° C and stirred for 30 minutes. After cooling to room temperature, the organic layer was extracted three times with 75 mL of chloroform. The organic layer was washed with water and aqueous solution of sodium hydrogencarbonate, followed by drying the obtained organic layer over anhydrous sodium sulfate (MgSO 4). After filtration, the solvent was distilled off under reduced pressure to obtain a white solid compound C. Silica gel column chromatography yielded 2.91 g (10 mmol, 45%) of Compound C.

Next, 60% sodium hydride (0.80 g, 20 mmol) and 30 mL of dehydrated dimethylformamide were added to a flask purged with nitrogen and stirred. To the compound D (5.65 g, 17 mmol) was added 80 mL of dimethylformamide to dissolve it, and then dropped into the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 60 mL of dimethylformamide was added to and dissolved in the compound represented by the formula (C) (5.25 g, 18 mmol), and the mixture was then added dropwise to the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration.

The filtered crystals were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 6.79 g (11.6 mmol, 68% yield) of the compound (1). MS: [M + H] &lt; + &gt; = 588.

< Manufacturing example  2>

Figure pat00072

160 mL of glacial acetic acid, 40 mL of sulfuric acid and 40 mL of distilled water were added to 12.0 g (44 mmol) of Compound B and heated. After that, the solution was cooled to 3-4 ° C, and 40 mL of a 1.64 M sodium nitrite solution was added, followed by stirring for 30 minutes. The solution was slowly added dropwise to 32 mL of bromic acid (HBr) in which 6.56 g (48.8 mmol) of copper chloride (CuCl 2 ) was dissolved at 3-4 ° C. The mixture was heated to 45 ° C, stirred for 30 minutes, heated to 80 ° C and stirred for 30 minutes. After cooling to room temperature, the organic layer was extracted three times with 150 mL of chloroform. The organic layer was washed with water and aqueous solution of sodium hydrogencarbonate, followed by drying the obtained organic layer over anhydrous sodium sulfate (MgSO 4). After filtration, the solvent was distilled off under reduced pressure to obtain a white solid compound E. Silica gel column chromatography gave 7.06 g (21 mmol, 48%) of compound E.

19.9 g (60 mmol) of the compound represented by the formula (D), 22.1 g (78 mmol) of 1-bromo-3-iodobenzene and 11.4 g (180 mmol) of copper powder, 18- 6 3.24 g (12 mmol) of potassium carbonate and 41.4 g (300 mmol) of potassium carbonate were added in this order, 200 mL of ortho-dichlorobenzene was added, and the mixture was stirred under reflux for 64 hours. After cooling to room temperature, 200 mL of distilled water was added and extracted twice with 200 mL of methylene chloride. Sodium sulfate, the resulting organic layer was dried (MgSO 4). Thereafter, after filtration, the solvent was distilled off under reduced pressure, and 17.0 g (34.8 mmol, 58%) of Compound F was obtained by silica gel column chromatography.

To a 500 mL round bottom flask was added 14.6 g (30 mmol) of the compound of formula F, 8.38 g (33 mmol) of bis (pinacolato) diboron, 2.45 g (3 mol) of PdCl2 (90 mol) and 1,4-dioxane (200 mL), and the mixture was stirred under reflux for 24 hours. After cooling to room temperature, 200 mL of distilled water was added and extracted twice with 200 mL of methylene chloride. Sodium sulfate, the resulting organic layer was dried (MgSO 4). Thereafter, after filtration, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 15.0 g of compound G (22.8 mmol, 76%).

15.0 g (22.8 mmol) of the compound represented by the formula G, 6.0 g (18 mmol) of the compound represented by the formula E, tetrakis triphenylphosphinopalladium (2.31 g, 2 mmol) and potassium carbonate 5.30 g (54 mmol), 40 mL of tetrahydrofuran, 20 mL of 1,4-dioxane and 15 mL of water were added thereto, followed by stirring under reflux for 12 hours. After cooling to room temperature, 20 mL of distilled water was added and extracted twice with 60 mL of methylene chloride. Sodium sulfate, the resulting organic layer was dried (MgSO 4). Thereafter, after filtration, the solvent was distilled off under reduced pressure, and 2.87 g (4.3 mmol, 24%) of Compound (10) was obtained by silica gel column chromatography. MS: [M + H] &lt; + &gt; = 664.

< Manufacturing example  3>

Figure pat00073

26.5 g (401 mmol) of malononitrile, a pyrrolidine catalyst amount and ethanol (600 mL) were added to 41.6 g (200 mmol) of Compound H, and the mixture was stirred at reflux for 9 hours. Thereafter, the solvent was distilled off under reduced pressure, and a yellow compound I was obtained by silica gel column chromatography. Thereafter, the yellow compound I was reslurried with petroleum ether, filtered, and dried under reduced pressure to obtain 24.8 g (84 mmol, 42%).

Next, the same method as the preparation of Compound E of Example 2 was conducted to synthesize the compound represented by Compound J at a yield of 44%.

Next, the same synthesis method as that of the compound (10) of Example 2 was conducted to synthesize the compound represented by the Compound 15 at a yield of 20%. MS: [M + H] &lt; + &gt; = 687.

< Example  4>

Figure pat00074

The same method as the preparation of Compound F of Example 2 was conducted to synthesize the compound represented by Compound L in a yield of 60%.

Next, the same method as the preparation of Compound G of Example 2 was conducted to synthesize the compound represented by Compound M at a yield of 78%.

Next, the same synthesis method as that of the compound (10) of Example 2 was conducted to synthesize the compound represented by the Compound 84 in a yield of 26%. MS: [M + H] &lt; + &gt; = 664.

< Example  5>

Figure pat00075

60% sodium hydride (0.88 g, 22 mmol) and 30 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. 80 mL of dimethylformamide was added to and dissolved in the compound N (5.66 g, 20 mmol), and the mixture was then added dropwise to the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 60 mL of dimethylformamide was added to and dissolved in 6.12 g (21 mmol) of the compound represented by the formula (C), and the solution was then added dropwise to the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration. The filtered crystals were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 7.54 g (14.0 mmol, 70% yield) of the compound (167). MS: [M + H] &lt; + &gt; = 539.

< Example  6>

Figure pat00076

Figure pat00077

150 ml of ethanol was added to the flask which had been substituted with nitrogen, and 0.2 g of sodium (1.73 g, 75 mmol) was subdivided and added dropwise at intervals of 10 minutes. After completion of the dropwise addition, stirring was continued for 1 hour. Then, benzamidine hydrochloride (7.82 g, 50 mmol) and (E) -2-cyano-3-phenylpropenoate (10.06 g, 50 mmol) were added dropwise and stirred for 4 hours. Thereafter, the sodium chloride produced by filtration was removed, and the filtrate was distilled off under reduced pressure. The acetone slurry was purified to obtain 7.1 g (26 mmol) of the compound represented by O.

50 mL of 1,4-dioxane and 50 mL of POCl 3 were added to 7.1 g (26 mmol) of the compound represented by the formula O in a 250 mL round bottom flask, and the mixture was stirred under reflux for 12 hours. The 1,4-dioxane and POCl 3 were removed by distillation, cooled to room temperature, and 100 mL of methylene chloride and 100 mL of distilled water were added. Extracted twice with 100 mL methylene chloride, and dried over sodium sulfate and the obtained organic layer (MgSO 4).

Thereafter, after filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 5.5 g of compound P (18.6 mmol, 72%).

Next, 60% sodium hydride (0.80 g, 20 mmol) and 30 mL of dehydrated dimethylformamide were added to a flask purged with nitrogen and stirred. To the above compound P (5.50 g, 17 mmol) was added 80 mL of dimethylformamide to dissolve, and then dropped into the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 60 mL of dimethylformamide was added to and dissolved in the compound represented by the formula (Q) (5.25 g, 18 mmol), followed by dropwise addition in the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration. The filtered crystals were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 6.00 g (10.2 mmol, 60% yield) of the compound (104). MS: [M + H] &lt; + &gt; = 588.

< Example  7>

Figure pat00078

17.0 g (60 mmol) of the compound represented by the formula R, 22.1 g (78 mmol) of 1-bromo-3-iodobenzene, 11.4 g (180 mmol) of copper powder, 18- 6 3.24 g (12 mmol) of potassium carbonate and 41.4 g (300 mmol) of potassium carbonate were added in this order, 200 mL of ortho-dichlorobenzene was added, and the mixture was stirred under reflux for 64 hours. After cooling to room temperature, 200 mL of distilled water was added and extracted twice with 200 mL of methylene chloride. Sodium sulfate, the resulting organic layer was dried (MgSO 4). After filtration, the solvent was distilled off under reduced pressure, and 15.8 g (36.0 mmol, 60%) of Compound S was obtained by silica gel column chromatography.

To a 500 mL round bottom flask was added 13.2 g (30 mmol) of the compound represented by the formula S, 8.38 g (33 mmol) of bis (pinacolato) diboron, 2.45 g (3 mol) of PdCl 2 (dppf) g (90 mol) and 1,4-dioxane (200 mL), and the mixture was stirred under reflux for 24 hours. After cooling to room temperature, 200 mL of distilled water was added and extracted twice with 200 mL of methylene chloride. Sodium sulfate, the resulting organic layer was dried (MgSO 4). After filtration, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 10.0 g of Compound T (20.7 mmol, 69%).

To a 500 mL round bottom flask was added 11.2 g (23.0 mmol) of the compound represented by the formula T, 6.0 g (18 mmol) of the compound represented by the formula E, tetrakis triphenylphosphinopalladium (2.31 g, 2 mmol) 5.30 g (54 mmol), 40 mL of tetrahydrofuran, 20 mL of 1,4-dioxane and 15 mL of water were added thereto, followed by stirring under reflux for 12 hours. After cooling to room temperature, 20 mL of distilled water was added and extracted twice with 60 mL of methylene chloride. Sodium sulfate, the resulting organic layer was dried (MgSO 4). Thereafter, after filtration, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 3.68 g (6.0 mmol, 26%) of the compound (160). MS: [M + H] &lt; + &gt; = 615.

< Example  8>

Figure pat00079

The same synthesis procedure as in the preparation of the compound A of Example 1 was carried out to synthesize the compound represented by the compound U at a yield of 88%.

Next, the same method as the preparation of Compound B of Example 1 was conducted to synthesize the compound represented by Compound V at a yield of 86%.

Next, the same synthesis method as that of the compound E of Example 2 was conducted to synthesize the compound represented by the compound W in a yield of 56%.

Next, the same synthesis method as that of the compound 10 of Example 2 was conducted to synthesize the compound represented by the Compound 164 at a yield of 26%. MS: [M + H] &lt; + &gt; = 663.

<Examples>

&Lt; Example 1 >

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

Hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. HT1 (400 Å) for transporting holes was vacuum deposited thereon, and a host (1) and a dopant Ir (ppy) 3 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 LiF was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

Figure pat00080

< Example  2>

An organic EL device was fabricated in the same manner as in Example 1 except that Compound 10 was used as the host material of the light emitting layer.

< Example  3>

An organic EL device was fabricated in the same manner as in Example 1 except that Compound 160 was used as the host material of the light emitting layer.

< Example  4>

An organic EL device was fabricated in the same manner as in Example 1 except that Compound 164 was used as the host material of the light emitting layer.

< Comparative Example  1>

An organic EL device was produced in the same manner as in Example 1 except that the following compound H-1 was used as the host material of the light emitting layer.

[H-1]

Figure pat00081

< Comparative Example  2>

An organic EL device was produced in the same manner as in Example 1 except that the following compound H-2 was used as the host material of the light emitting layer.

[H-2]

Figure pat00082

The evaluation of the organic EL device manufactured through the above-mentioned Examples and Comparative Examples is shown in Table 1 below.

[Table 1]

Figure pat00083

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

Claims (12)

A compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00084

In Formula 1,
Ar1 and Ar2 are the same or different and are each independently selected from the group consisting of deuterium; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
X1 to X3 are the same or different and are each independently C-CN, N or C (R4)
At least one of X1 to X3 is C-CN,
L is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,
R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
Y is N (R5), O, C (R6) (R7), S or Si (R8) (R9)
R5 to R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,
a and c are the same or different and each independently represents an integer of 0 to 4,
b is an integer of 0 to 2,
p is an integer of 1 to 5,
When a, b, and p are each 2 or more, the structures in parentheses 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 (2) to (6)
(2)
Figure pat00085

(3)
Figure pat00086

[Chemical Formula 4]
Figure pat00087

[Chemical Formula 5]
Figure pat00088

[Chemical Formula 6]
Figure pat00089

In the above Formulas 2 to 6,
The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, R5 to R9, a, b, c and p are as shown in Formula (1). The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (7) to (12):
(7)
Figure pat00090

[Chemical Formula 8]
Figure pat00091

[Chemical Formula 9]
Figure pat00092

[Chemical formula 10]
Figure pat00093

(11)
Figure pat00094

[Chemical Formula 12]
Figure pat00095

In the above formulas (7) to (12)
The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, Y, a, b, c and p are as shown in formula (1). The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 13 or 14:
[Chemical Formula 13]
Figure pat00096

[Chemical Formula 14]
Figure pat00097

In the above formulas (13) and (14)
The definitions of Ar1, Ar2, X1 to X3, L, R1 to R3, Y, a, b, c and p are as shown in formula (1). [2] The method according to claim 1,
Figure pat00098
Wherein the moiety is any one selected from the following structural formulas:
Figure pat00099
Figure pat00100
Figure pat00101

Figure pat00102
Figure pat00103
Figure pat00104

Figure pat00105

In the above formula,
The definitions of X1 to X3 are the same as those in formula (1). 2. The compound of claim 1, wherein L is a direct bond; Or substituted or unsubstituted phenylene. [2] The compound according to claim 1, wherein Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:
Figure pat00106

Figure pat00107

Figure pat00108

Figure pat00109

Figure pat00110

Figure pat00111

Figure pat00112

Figure pat00113

Figure pat00114

Figure pat00115

Figure pat00116

Figure pat00117

Figure pat00118

Figure pat00119

Figure pat00120

Figure pat00121

Figure pat00122

Figure pat00123

Figure pat00124

Figure pat00125

Figure pat00126

Figure pat00127

Figure pat00128

Figure pat00129

Figure pat00130

Figure pat00131

Figure pat00132

Figure pat00133

Figure pat00134

Figure pat00135

Figure pat00136

Figure pat00137

Figure pat00138

Figure pat00139

Figure pat00140
 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 a compound according to any one of claims 1 to 8 Organic light emitting device. [Claim 11] The organic light emitting device according to claim 9, wherein the organic compound layer containing the compound is a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting holes and transporting holes. [Claim 11] 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 a layer simultaneously performing electron injection and electron transport. The organic light emitting device according to claim 9, wherein the organic compound layer containing the compound is a light emitting layer.
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