KR101753485B1 - Compounds and organic electronic device using the same - Google Patents

Compounds and organic electronic device using the same Download PDF

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KR101753485B1
KR101753485B1 KR1020150149691A KR20150149691A KR101753485B1 KR 101753485 B1 KR101753485 B1 KR 101753485B1 KR 1020150149691 A KR1020150149691 A KR 1020150149691A KR 20150149691 A KR20150149691 A KR 20150149691A KR 101753485 B1 KR101753485 B1 KR 101753485B1
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장분재
이동훈
이형진
하재승
정원익
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주식회사 엘지화학
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    • 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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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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Abstract

The present invention provides a compound and an organic light emitting device comprising the same.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic light-

The present invention claims the benefit of Korean Patent Application No. 10-2014-0146216 filed on October 27, 2014, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

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

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

Korean Patent Publication No. 2000-0051826

The present specification aims to provide a compound and an organic light emitting device including the same.

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

[Chemical Formula 1]

Figure 112015104466078-pat00001

In Formula 1,

Ar 1 to Ar 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino 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 heteroaryl 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 heteroarylamine group; Or a substituted or unsubstituted arylamine group,

R 1 to R 4 are the same or different and are each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino 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 heteroaryl 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 heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

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

a, b, c and d are the same or different and each independently represents an integer of 0 to 3,

q are the same or different and are each independently an integer of 0 to 3,

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

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

when c is 2 or more, R 3 are the same or different from each other,

when d is 2 or more, R 4 are the same or different from each other,

When q is 2 or more, L is 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 hole transporting, light emitting, electron transporting, or electron injecting materials. In addition, the compounds described in the present specification can be preferably used as a light emitting layer, an electron transporting or electron injecting material.

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

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

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; An amino group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; A heteroaryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; A heteroarylamine group; And an arylamine group, or a substituted or unsubstituted aryl group to which at least two of the above-exemplified substituents are connected. 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 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, 4-methylhexyl, 5-methylhexyl and the like.

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.

When the fluorenyl group is substituted,

Figure 112015104466078-pat00002
,
Figure 112015104466078-pat00003
,
Figure 112015104466078-pat00004
And
Figure 112015104466078-pat00005
And the like. However, the present invention is not limited thereto.

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

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted 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 adjacent groups bonded to each other to form a ring means that adjacent groups are bonded to each other to form a 5-membered to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring as described above , Monocyclic or polycyclic, and may be aliphatic, aromatic, or condensed forms thereof, but is not limited thereto.

As used herein, the hydrocarbon ring or heterocycle may be selected from the examples of cycloalkyl, aryl or heteroaryl groups described above, except monovalent, and may be monocyclic or polycyclic, aliphatic or aromatic, or a condensed form thereof Yes. But is not limited thereto.

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.

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH 2 ) is substituted with another substituent, represented by -NR 100 R 101 , and R 100 and R 101 are the same as or different from each other Each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group (provided that at least one of R 100 and R 101 is not hydrogen). For example, -NH 2 ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group can be applied to the description of the aryl group described above.

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

In this specification, the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heteroaryl 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 the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (11).

(2)

Figure 112015104466078-pat00006

(3)

Figure 112015104466078-pat00007

[Chemical Formula 4]

Figure 112015104466078-pat00008

[Chemical Formula 5]

Figure 112015104466078-pat00009

[Chemical Formula 6]

Figure 112015104466078-pat00010

(7)

Figure 112015104466078-pat00011

[Chemical Formula 8]

Figure 112015104466078-pat00012

[Chemical Formula 9]

Figure 112015104466078-pat00013

[Chemical formula 10]

Figure 112015104466078-pat00014

(11)

Figure 112015104466078-pat00015

In the above Chemical Formulas 2 to 11, the definitions of Ar 1 to Ar 4 , R 1 to R 4 , L, a, b, c, d and q are as shown in Chemical Formula 1.

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

[Chemical Formula 12]

Figure 112015104466078-pat00016

In the above formula (12), Ar 1 to Ar 4 , R 1 to R 4 , a, b, c and d are as defined in formula (1).

According to one embodiment of the present disclosure, L is a direct bond; A substituted or unsubstituted arylene group having 1 to 4 rings; Or a substituted or unsubstituted heteroarylene group.

According to one embodiment of the present disclosure, L is a direct bond; A substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrylene group; A substituted or unsubstituted pyrenylene group; A substituted or unsubstituted chryshenylene group; A substituted or unsubstituted fluorenylene group; Or a substituted or unsubstituted heteroarylene group.

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

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

According to one embodiment of the present invention, L is a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, L is an arylene group.

According to one embodiment of the present disclosure, L is a direct bond; Or a substituted or unsubstituted arylene group having 1 to 4 rings.

According to one embodiment of the present disclosure, L is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrylene group; A substituted or unsubstituted pyrenylene group; A substituted or unsubstituted chryshenylene group; Or a substituted or unsubstituted fluorenylene group.

According to one embodiment of the present invention, L is a direct bond or a straight-chain or branched alkylene group having from 1 to 20 carbon atoms, such as a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrylene group, a pyrenylene group, It is a stove.

According to one embodiment of the present invention, L is a direct bond or a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, a phenanthrylene group, a pyrenylene group, or a substituted or unsubstituted fluorenylene group .

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

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (13) to (22).

[Chemical Formula 13]

Figure 112015104466078-pat00017

[Chemical Formula 14]

Figure 112015104466078-pat00018

[Chemical Formula 15]

Figure 112015104466078-pat00019

[Chemical Formula 16]

Figure 112015104466078-pat00020

[Chemical Formula 17]

Figure 112015104466078-pat00021

[Chemical Formula 18]

Figure 112015104466078-pat00022

[Chemical Formula 19]

Figure 112015104466078-pat00023

[Chemical Formula 20]

Figure 112015104466078-pat00024

[Chemical Formula 21]

Figure 112015104466078-pat00025

[Chemical Formula 22]

Figure 112015104466078-pat00026

In the formulas (13) to (22), Ar 1 to Ar 4 , R 1 to R 4 , L, a, b, c, d and q are as defined in the above formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (23) to (26).

(23)

Figure 112015104466078-pat00027

≪ EMI ID =

Figure 112015104466078-pat00028

(25)

Figure 112015104466078-pat00029

(26)

Figure 112015104466078-pat00030

In Chemical Formulas 23 to 26, Ar 1 to Ar 4 , R 2 to R 4 , L, b, c, d and q are as defined in Chemical Formula 1,

R 11 to R 13 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino 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 heteroaryl 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 heteroarylamine group; Or a substituted or unsubstituted arylamine group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

a11 is an integer of 0 to 6,

a12 and a13 are the same or different and are each independently an integer of 0 to 4,

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

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

If more than a13 is 2, R 13 is the same as or different from each other.

According to one embodiment of the present disclosure, Ar 1 to Ar 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino 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 heteroaryl 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 heteroarylamine group; Or a substituted or unsubstituted arylamine group.

According to one embodiment of the present disclosure, Ar 1 to Ar 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, Ar 1 to Ar 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; An aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently is a mono- to tetra-ring substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a mono- to tricyclic substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently is a monocyclic or bicyclic substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently an aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a mono- to tricyclic aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a monocyclic or bicyclic aryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 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 crecenyl group; Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different from each other and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, , Or a fluorenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different from each other and are each independently a phenyl group; Or a naphthyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a naphthyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, Ar 1 to Ar 4 are the same or different and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, Ar 1 to Ar 4 are the same or different and each independently hydrogen; heavy hydrogen; Or a phenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are phenyl groups.

According to one embodiment of the present disclosure, Ar 1 to Ar 4 are independently selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, Ar 1 to Ar 4 are hydrogen.

According to one embodiment of the present disclosure, q is 1 or 2.

According to one embodiment of the present disclosure, R 1 to R 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino 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 heteroaryl 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 heteroarylamine group; Or a substituted or unsubstituted arylamine group, or combine with each other to form a substituted or unsubstituted hydrocarbon ring or a heterocycle.

According to one embodiment of the present disclosure, R 1 to R 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present disclosure, R 1 to R 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group; An aryl group; Or a substituted or unsubstituted heteroaryl group, or are bonded to each other to form a ring.

According to one embodiment of the present disclosure, R 1 to R 4 combine with each other to form a hydrocarbon ring or a heterocyclic ring.

According to one embodiment of the present disclosure, R 1 to R 4 are independently selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R 1 to R 4 are hydrogen.

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

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

According to one embodiment of the present disclosure, L represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, Substituted or unsubstituted pyrenylene groups, substituted or unsubstituted pyrenylene groups, substituted or unsubstituted pyrenylene groups, substituted or unsubstituted pyrenylene groups, substituted or unsubstituted pyrenylene groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted pyrene groups, Or a substituted or unsubstituted fluorenylene group.

According to one embodiment of the present disclosure, L is a group selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracenylene group, a phenanthrylene group, a pyrenylene group, a perylenylene group, Or a fluorenylene group.

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

Figure 112015104466078-pat00031

Figure 112015104466078-pat00032

Figure 112015104466078-pat00033

Figure 112015104466078-pat00034

Figure 112015104466078-pat00035

Figure 112015104466078-pat00036

Figure 112015104466078-pat00037

Figure 112015104466078-pat00038

Figure 112015104466078-pat00039

Figure 112015104466078-pat00040

Figure 112015104466078-pat00041

Figure 112015104466078-pat00042

Figure 112015104466078-pat00043

Figure 112015104466078-pat00044

Figure 112015104466078-pat00045

Figure 112015104466078-pat00046

Figure 112015104466078-pat00047

Figure 112015104466078-pat00048

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

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

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

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

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

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

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

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

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

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

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

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

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1).

When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

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

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

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

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

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

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

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

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

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

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

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

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

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing 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, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

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

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

< Manufacturing example >

<Preparation Example 1> Preparation of [Compound 1]

Figure 112015104466078-pat00049

3-Chloro-9H-carbazole (20.1 g, 100 mmol) was dissolved in 300 mL anhydrous tetrahydrofuran (THF) in a nitrogen atmosphere and then cooled to -78 deg. n-Butyl lithium (75 mL, 120 mmol, 1.6 M in hexane) was slowly dropped. After 1 hour, chlorodiphenylphosphane (22 g, 100 mmol) was slowly added thereto, stirred for 1 hour, and then warmed to room temperature. After 300 mL of water was added, the organic layer was extracted, treated with magnesium magnesium and filtered. The filtrate was distilled under reduced pressure to prepare [Compound A-1]. (27.4 g, yield 71%, MS: [M + H] &lt; + &gt; = 386)

[Compound A-1] (27.4 g, 71 mmol) was dissolved in 300 mL of chloroform, and hydrogen peroxide (30 wt%, 200 mL) was slowly added dropwise at 0 ° C. After 12 hours, the reaction solution was washed with 200 mL of a saturated aqueous sodium hydrogen sulfite solution. The organic layer was treated with magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and then purified by column chromatography to obtain [Compound A]. (21.4 g, yield 75%, MS: [M + H] &lt; + &gt; = 402)

Figure 112015104466078-pat00050

The compound [A] (15 g, 37.3 mmol), bis (pinacolato) diboron (9.5 g, 37.3 mmol) and potassium acetate (33 g, 111 mmol) were added to 200 ml of dioxane in a nitrogen atmosphere and heated with stirring . Bis (dibenzylidineacetone) palladium (638 mg, 1.11 mmol) and tricyclohexylphosphine (639 mg, 2.22 mmol) were added under reflux and the mixture was heated and stirred for 12 hours. After the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the product was washed with ethanol to prepare [Compound AB]. (13.8 g, yield 75%, MS: [M + H] &lt; + &gt; = 494)

Figure 112015104466078-pat00051

[Compound A] (15.0 g, 37.3 mmol) and [Compound AB] (18.4 g, 37.3 mmol) were added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate aqueous solution and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added thereto, and the mixture was refluxed with stirring for 7 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [compound 1]. (19.1 g, yield 70%, MS: [M + H] &lt; + &gt; = 733)

Preparation of <Production Example 2> [compound 2]

Figure 112015104466078-pat00052

[Compound B] was prepared in the same manner as in the preparation of [Compound A], except that 2-chloro-9H-carbazole was used instead of 3-chloro-9H-carbazole in Production Example 1. (Yield: 44%, MS: [M + H] < + > = 402)

[Compound B] (15.0 g, 37.3 mmol) and [Compound AB] (18.4 g, 37.3 mmol) were added to 200 mL of dioxane. 100 ml of 2.0 MK 3 CO 4 and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added thereto, and the mixture was refluxed with stirring for 7 hours. The solution was cooled to room temperature, filtered and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2]. (18.0 g, yield 66%, MS: [M + H] &lt; + &gt; = 733)

Preparation of <Production Example 3> [compound 3]

Figure 112015104466078-pat00053

[Compound C] was prepared in the same manner as in the preparation of [Compound A], except that 4-chloro-9H-carbazole was used instead of 3-chloro-9H-carbazole in Production Example 1. (Yield: 40%, MS: [M + H] < + > = 402)

[Compound C] (15.0 g, 37.3 mmol) and [Compound AB] (18.4 g, 37.3 mmol) were added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added thereto, and the mixture was refluxed with stirring for 8 hours. The solution was cooled to room temperature, filtered and the resulting solid was recrystallized from chloroform and ethanol to give [compound 3]. (20.6 g, yield 75%, MS: [M + H] &lt; + &gt; = 733)

Preparation of <Production Example 4> [compound 5]

Figure 112015104466078-pat00054

(15 g, 37.3 mmol), bis (pinacolato) diboron (9.5 g, 37.3 mmol) and potassium acetate (33 g, 111 mmol) were added to 200 ml of dioxane and heated with stirring in a nitrogen atmosphere . Bis (dibenzylidineacetone) palladium (638 mg, 1.11 mmol) and tricyclohexylphosphine (639 mg, 2.22 mmol) were added under reflux and the mixture was heated and stirred for 12 hours. After the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the product was washed with ethanol to prepare [compound BB]. (Yield: 79%, MS: [M + H] &lt; + &gt; = 494)

[Compound B] (15.0 g, 37.3 mmol) and [Compound BB] (18.4 g, 37.3 mmol) were added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added, and the mixture was refluxed with stirring for 7 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 5]. (19.5 g, yield 71%, MS: [M + H] &lt; + &gt; = 733)

Preparation of <Production Example 5> [Compound 6]

Figure 112015104466078-pat00055

[Compound C] (15.0 g, 37.3 mmol) and [Compound BB] (18.4 g, 37.3 mmol) were added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added, and the mixture was refluxed with stirring for 7 hours. The mixture was cooled to room temperature, filtered and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 6]. (17.0 g, yield 62%, MS: [M + H] &lt; + &gt; = 733)

Preparation of <Production Example 6> [compound 11]

Figure 112015104466078-pat00056

[Compound A] (15.0 g, 37.3 mmol) and diphenyl (3- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -9H-carbazol-9-yl) phosphine oxide (21.2 g, 37.3 mmol) was added to 300 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added thereto, and the mixture was refluxed with stirring for 8 hours. The solution was cooled to room temperature, filtered and the resulting solid was recrystallized from chloroform and ethanol to give [compound 11]. (15.4 g, yield 51%, MS: [M + H] &lt; + &gt; = 809)

Preparation of <Production Example 7> [compound 16]

Figure 112015104466078-pat00057

[Compound B] (15.0 g, 37.3 mmol) and diphenyl (2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -9H-carbazol-9-yl) phosphine oxide (21.2 g, 37.3 mmol) was added to 300 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added thereto, and the mixture was refluxed for 6 hours. The reaction mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 16]. (18.4 g, yield 61%, MS: [M + H] &lt; + &gt; = 809)

Preparation of <Production Example 8> [compound 21]

Figure 112015104466078-pat00058

The compound [B] (15.0 g, 37.3 mmol) and the diphenyl (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -9H-carbazol-9-yl) phosphine oxide (21.2 g, 37.3 mmol) was added to 300 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added, and the mixture was refluxed with stirring for 9 hours. The mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 21]. (19.0 g, yield 63%, MS: [M + H] &lt; + &gt; = 809)

Preparation of <Production Example 9> [compound 44]

Figure 112015104466078-pat00059

The compound [B] (15.0 g, 37.3 mmol) and 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) naphthalene , 18.6 mmol) were added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added thereto, and the mixture was refluxed for 6 hours. The solution was cooled to room temperature, filtered and the resulting solid was recrystallized from chloroform and ethanol to give [compound 44]. (8.5 g, yield 53%, MS: [M + H] &lt; + &gt; = 859)

Preparation of <Production Example 10> [compound 57]

Figure 112015104466078-pat00060

[Compound D] was prepared in the same manner as in the preparation of [Compound A], except that 8-chloro-11H-benzo [a] carbazole was used instead of 3-chloro-9H- . (Yield: 36%, MS: [M + H] < + > = 452)

[Compound D] (15.0 g, 33.2 mmol) and [Compound AB] (13.3 g, 33.2 mmol) were added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added, and the mixture was refluxed with stirring for 7 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 57]. (17.4 g, yield 67%, MS: [M + H] &lt; + &gt; = 783)

Preparation of <Production Example 11> [compound 73]

Figure 112015104466078-pat00061

Compound [E] was synthesized in the same manner as in [Manufacturing Method 1] except that 3-chloro-5H-benzo [ ]. (Yield 39%, MS: [M + H] < + > = 452)

[Compound E] (15.0 g, 33.2 mmol) and [Compound BB] (13.3 g, 33.2 mmol) were added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added, and the mixture was refluxed with stirring for 9 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [compound 73]. (16.1 g, yield 62%, MS: [M + H] &lt; + &gt; = 783)

Preparation of <Production Example 12> [compound 90]

Figure 112015104466078-pat00062

Compound [F] was prepared in the same manner as in the preparation of [Compound A], except that 10-chloro-7H-benzo [c] carbazole was used instead of 3-chloro-9H- . (Yield 39%, MS: [M + H] < + > = 452)

[Compound F] (15.0 g, 33.2 mmol) and diphenyl (3- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) -9H-carbazol-9-yl) phosphine oxide (18.9 g, 33.2 mmol) was added to 200 mL of dioxane. 100 mL of 2.0 M potassium carbonate and 0.2 g of bis (tri-tert-butylphosphine) palladium (0) were added thereto, and the mixture was refluxed for 6 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 90]. (16.5 g, yield 58%, MS: [M + H] &lt; + &gt; = 859)

< Example >

< Comparative Example  1-1>

The compounds prepared in the above Preparation Examples were subjected to high purity sublimation purification by a known method, and then a green organic light emitting device was prepared in the following manner.

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

(60 nm) / TCTA (80 nm) / CBP + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / CBP using a [Compound A- The organic EL device was fabricated by constructing a light emitting device in the order of ET-A (30 nm) / LiF (1 nm) / Al (200 nm).

The structures of m-MTDATA, TCTA, Ir (ppy) 3 , [Compound A-1] and BCP, [ET-A] are as follows.

        [m-MTDATA] [TCTA] [ET-A]

Figure 112015104466078-pat00063

[Ir (ppy) 3 ] [BCP] [Compound A-1]

Figure 112015104466078-pat00064

< Experimental Example  1-1>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 1] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-2>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1> except that [Compound 2] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-3>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1> except that [Compound 3] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-4>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 5] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-5>

An organic light emitting device was prepared in the same manner as in <Comparative Example 1-1>, except that [Compound 6] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-6>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1> except that [Compound 11] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-7>

An organic light emitting device was prepared in the same manner as in <Comparative Example 1-1>, except that [Compound 16] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-8>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 21] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-9>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 44] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-10>

An organic light emitting device was prepared in the same manner as in <Comparative Example 1-1>, except that [Compound 57] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-11>

An organic light emitting device was prepared in the same manner as in <Comparative Example 1-1> except that [Compound 73] was used in place of [Compound A-1] in <Comparative Example 1-1>.

< Experimental Example  1-12>

An organic light emitting device was prepared in the same manner as in <Comparative Example 1-1>, except that [Compound 90] was used in place of [Compound A-1] in <Comparative Example 1-1>.

When current was applied to the organic light-emitting device fabricated according to Example 1-1 to Example 1-12 and Comparative Example 1-1, the results shown in Table 1 were obtained

division Voltage
(V @ 10 mA / cm 2 ) efficiency
(Cd / A @ 10mA / cm 2) Emission peak
(nm) Experimental Example 1-1 5.32 44.2 516 Experimental Example 1-2 5.32 44.9 517 Experimental Example 1-3 5.43 42.9 518 Experimental Examples 1-4 5.59 43.3 517 Experimental Examples 1-5 5.29 43.8 518 Experimental Example 1-6 5.45 42.5 517 Experimental Example 1-7 5.44 43.4 516 Experimental Examples 1-8 5.35 44.5 518 Experimental Examples 1-9 5.48 45.6 517 Experimental Example 1-10 5.49 42.7 518 Experimental Example 1-11 5.33 44.7 516 Experimental Example 1-12 5.28 43.5 517 Comparative Example 1-1 7.12 31.7 516

As shown in Table 1, the green organic luminescent devices of Experimental Examples 1-1 to 1-12 using the compound according to one embodiment of the present invention as the host material of the light emitting layer, 1] was superior to the green organic light emitting device of Comparative Example 1-1 in terms of current efficiency and driving voltage.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

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 112017016102271-pat00065

In Formula 1,
Ar 1 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; Or a substituted or unsubstituted arylamine group,
R 1 to R 4 are the same or different and are each independently hydrogen; Or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
L are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
a, b, c and d are the same or different and each independently represents an integer of 0 to 3,
q are the same or different from each other and are each independently an integer of 0 to 3,
when a is 2 or more, R 1 are the same or different from each other,
when b is 2 or more, R 2 are the same or different from each other,
when c is 2 or more, R 3 are the same or different from each other,
when d is 2 or more, R 4 are the same or different from each other,
When q is 2 or more, L is 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 (11):
(2)
Figure 112015104466078-pat00066

(3)
Figure 112015104466078-pat00067

[Chemical Formula 4]
Figure 112015104466078-pat00068

[Chemical Formula 5]
Figure 112015104466078-pat00069

[Chemical Formula 6]
Figure 112015104466078-pat00070

(7)
Figure 112015104466078-pat00071

[Chemical Formula 8]
Figure 112015104466078-pat00072

[Chemical Formula 9]
Figure 112015104466078-pat00073

[Chemical formula 10]
Figure 112015104466078-pat00074

(11)
Figure 112015104466078-pat00075

In the above Chemical Formulas 2 to 11, the definitions of Ar 1 to Ar 4 , R 1 to R 4 , L, a, b, c, d and q are as shown in Chemical Formula 1. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 12:
[Chemical Formula 12]
Figure 112015104466078-pat00076

In the above formula (12), Ar 1 to Ar 4 , R 1 to R 4 , a, b, c and d are as defined in the above formula (1). The compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas (13) to (22):
[Chemical Formula 13]
Figure 112017016102271-pat00077

[Chemical Formula 14]
Figure 112017016102271-pat00078

[Chemical Formula 15]
Figure 112017016102271-pat00079

[Chemical Formula 16]
Figure 112017016102271-pat00080

[Chemical Formula 17]
Figure 112017016102271-pat00081

[Chemical Formula 18]
Figure 112017016102271-pat00082

[Chemical Formula 19]
Figure 112017016102271-pat00083

[Chemical Formula 20]
Figure 112017016102271-pat00084

[Chemical Formula 21]
Figure 112017016102271-pat00085

[Chemical Formula 22]
Figure 112017016102271-pat00086

In formulas (13) to (22), Ar 1 to Ar 4 , R 1 to R 4 , a, b, c and d have the same meanings as in formula (1). The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (23) to
(23)
Figure 112017016102271-pat00087

&Lt; EMI ID =
Figure 112017016102271-pat00088

(25)
Figure 112017016102271-pat00089

(26)
Figure 112017016102271-pat00090

In Chemical Formulas 23 to 26, Ar 1 to Ar 4 , R 2 to R 4 , L, b, c, d and q are as defined in Chemical Formula 1,
R 11 to R 13 are the same or different and each independently hydrogen; Or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
a11 is an integer of 0 to 6,
a12 and a13 are the same or different and are each independently an integer of 0 to 4,
If more than a11 is 2, R 11 is the same as or different from each other, and
If more than a12 is 2, R 12 is the same as or different from each other,
If more than a13 is 2, R 13 is the same as or different from each other. The compound according to claim 1, wherein Ar 1 to Ar 4 are the same or different and are each independently a substituted or unsubstituted aryl group. 2. The compound of claim 1, wherein L is a direct bond; Or a substituted or unsubstituted arylene group having 1 to 4 rings. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following formulas:
Figure 112015104466078-pat00091

Figure 112015104466078-pat00092

Figure 112015104466078-pat00093

Figure 112015104466078-pat00094


Figure 112015104466078-pat00096

Figure 112015104466078-pat00097

Figure 112015104466078-pat00098

Figure 112015104466078-pat00099

Figure 112015104466078-pat00100

Figure 112015104466078-pat00101

Figure 112015104466078-pat00102

Figure 112015104466078-pat00103

Figure 112015104466078-pat00104

Figure 112015104466078-pat00105

Figure 112015104466078-pat00106

Figure 112015104466078-pat00107

Figure 112015104466078-pat00108
 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. The method of 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. The method of claim 9,
Wherein the organic compound layer containing the compound is an electron injecting layer, an electron transporting layer, or a layer simultaneously performing electron injection and electron transport. The method of claim 9,
Wherein the organic compound layer containing the compound is a light emitting layer.
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WO2009136586A1 (en) 2008-05-08 2009-11-12 新日鐵化学株式会社 Compound for organic electroluminescent elements and organic electroluminescent element
WO2013172835A1 (en) * 2012-05-17 2013-11-21 Universal Display Corporation Biscarbazole derivative host materials for oled emissive region
WO2014024856A1 (en) * 2012-08-07 2014-02-13 国立大学法人九州大学 Organic electroluminescent element, and compound, carrier transport material and host material for use in same

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WO2009136586A1 (en) 2008-05-08 2009-11-12 新日鐵化学株式会社 Compound for organic electroluminescent elements and organic electroluminescent element
WO2013172835A1 (en) * 2012-05-17 2013-11-21 Universal Display Corporation Biscarbazole derivative host materials for oled emissive region
WO2014024856A1 (en) * 2012-08-07 2014-02-13 国立大学法人九州大学 Organic electroluminescent element, and compound, carrier transport material and host material for use in same

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