KR101813761B1

KR101813761B1 - New compounds and organic electronic device including the same

Info

Publication number: KR101813761B1
Application number: KR1020150144881A
Authority: KR
Inventors: 장분재; 이동훈; 이형진; 하재승; 정원익
Original assignee: 주식회사 엘지화학
Priority date: 2014-10-17
Filing date: 2015-10-16
Publication date: 2018-01-30
Also published as: KR20160045612A

Abstract

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

Description

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

TECHNICAL FIELD The present invention relates to a novel organic compound and an organic light emitting device including the organic compound. The present application claims the benefit of Korean Patent Application No. 10-2014-0140920 filed on October 17, 2014, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

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

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

[Chemical Formula 1]

In Formula 1,

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 heterocyclic 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 adjacent two or more substituents may be bonded to each other to form a substituted or unsubstituted ring,

X is a substituted phenyl group; A substituted or unsubstituted aryl group having two or more rings; Or a substituted or unsubstituted heterocyclic group,

a, b, c and d are the same or different and each is an integer of 0 to 4,

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.

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 in this specification can be used as hole injecting, hole transporting, hole injecting and transporting, luminescence, electron transporting, or electron injecting materials, and preferably as materials for the light emitting layer, electron transporting layer, or electron injecting 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.

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 heterocyclic 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, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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 other 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, 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,

,

,

And

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

In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, S, Si and Se as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, 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, 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.

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

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

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

In the present specification, the description of the above-mentioned heterocyclic group can be applied, except that the heteroarylene is an aromatic 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; Or a substituted or unsubstituted aromatic heterocycle.

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 benzene, naphthalene, anthracene, and the like, but are not limited thereto.

As used herein, an aliphatic heterocycle means an aliphatic ring containing at least one of the heteroatoms.

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 "substituted phenyl group" 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 heterocyclic group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; A heteroarylamine group; And an arylamine group. The term " aryl group " means a phenyl group substituted with at least one substituent selected from the group consisting of an aryl group and an arylamine group.

According to one embodiment of the present disclosure, X is a substituted phenyl group; A substituted or unsubstituted aryl group having two or more rings; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, X is a phenyl group substituted with a substituted or unsubstituted aryl group; A phenyl group substituted with a substituted or unsubstituted heterocyclic group; A substituted or unsubstituted aryl group having two or more rings; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, X is a phenyl group substituted with a substituted or unsubstituted aryl group; A phenyl group substituted with a substituted or unsubstituted heterocyclic group; A substituted or unsubstituted 2 to 4-membered aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, X is a phenyl group substituted with a substituted or unsubstituted aryl group; A phenyl group substituted with a substituted or unsubstituted heterocyclic group; A substituted or unsubstituted 2 to 4-membered aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

According to one embodiment of the present invention, X is a phenyl group substituted with a substituted or unsubstituted aryl group; A phenyl group substituted with a substituted or unsubstituted heterocyclic group containing at least one of N, O and S; A substituted or unsubstituted 2 to 4-membered aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

According to one embodiment of the present invention, X is a phenyl group substituted with a substituted or unsubstituted aryl group; A phenyl group substituted with a mono- to tricyclic substituted or unsubstituted heterocyclic group containing at least one of N, O and S; A substituted or unsubstituted 2 to 4-membered aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

According to one embodiment of the present disclosure, X is a substituted phenyl group.

According to one embodiment of the present disclosure, X is a substituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

According to one embodiment of the present invention, X is a phenyl group substituted with a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, X is a phenyl group substituted with an aryl group or a heterocyclic group.

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

(2)

In the above formula (2), R ₁ to R ₄ , a, b, c and d are as defined in formula (1)

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

Ar is the same or different and is independently selected from the group consisting of deuterium; 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 heterocyclic 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; A substituted or unsubstituted arylamine group or an adjacent two or more substituents bonded to each other to form a substituted or unsubstituted ring,

r is an integer of 0 to 3, and when r is 2 or more, L is the same or different from each other.

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

According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted aryl group of 1 to 4 rings; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted aryl group of 1 to 4 rings; Or a substituted or unsubstituted heterocyclic group of 1 to 3 rings.

According to one embodiment of the present disclosure, Ar is a substituted or unsubstituted aryl group of 1 to 4 rings; Or a mono- to tricyclic substituted or unsubstituted heterocyclic group containing at least one of N, O and S. [

According to one embodiment of the present invention, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A monocyclic to tricyclic substituted or unsubstituted heterocyclic group containing at least one N; Or a substituted or unsubstituted heterocyclic group containing at least one of O and S.

According to one embodiment of the present invention, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A monocyclic to tricyclic substituted or unsubstituted heterocyclic group containing at least one N; Or a monocyclic to tricyclic substituted or unsubstituted heterocyclic group containing at least one of O and S.

According to one embodiment of the present invention, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A monocyclic to tricyclic substituted or unsubstituted heterocyclic group containing at least one N; Or a tricyclic substituted or unsubstituted heterocyclic group containing at least one of O and S.

According to one embodiment of the present invention, Ar represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A monocyclic to tricyclic substituted or unsubstituted heterocyclic group containing at least one N; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofuranyl group.

According to one embodiment of the present invention, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group A substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted furan group, a substituted or unsubstituted furan group, a substituted or unsubstituted furan group, a substituted or unsubstituted furan group, Substituted or unsubstituted imidazole groups, substituted or unsubstituted thiazole groups, substituted or unsubstituted oxazole groups, substituted or unsubstituted oxadiazole groups, substituted or unsubstituted triazole groups, substituted or unsubstituted aryl groups, Substituted or unsubstituted pyridyl groups, substituted or unsubstituted bipyridyl groups, substituted or unsubstituted pyrimidyl groups, substituted or unsubstituted triazine groups, substituted or unsubstituted triazole groups, substituted or unsubstituted acridyl groups, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a phthalazinyl group, A substituted or unsubstituted pyridopyrimidinyl group, a substituted or unsubstituted pyridopyrimidinyl group, a substituted or unsubstituted pyrazinopyranyl group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted indole group, A substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzocarbazole group, a substituted or unsubstituted benzoxazole group, A substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted phenanthroline, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted phenothiazinyl group, or a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiazolyl group, Dibenzofuranyl group.

According to one embodiment of the present invention, Ar is a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a fluorenyl group, a thiophene group, A thiazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazinyl group, A carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, A benzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazole group, a benzothiazole group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group,

According to one embodiment of the present invention, the formula (1) may be represented by the following formulas (3) to (11).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas 3 to 11,

R ₁ , R _2, R ₄ , X, a, b and d are as defined in the formula (1)

R ₁₂ and 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 heterocyclic 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; A substituted or unsubstituted arylamine group or an adjacent two or more substituents bonded to each other to form a substituted or unsubstituted ring,

b ₁ and c ₁ are the same or different and each independently represents an integer of 0 to 6,

When b ₁ is 2 or more, R ₁₂ are the same or different from each other,

When c ₁ is 2 or more, R ₁₃ are the same or different from each other.

According to one embodiment of the present invention, the formula (1) may be represented by the following formulas (12) to (16).

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

In Formulas 12 to 16,

R ₁ , R ₂ and R ₄ , X, a, b and d are as defined in the formula (1)

R ₂₁ to R ₂₅ 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 heterocyclic 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; A substituted or unsubstituted arylamine group or a substituted or unsubstituted arylamine group,

r1, r2, r4 and r5 are the same or different and each independently represents an integer of 0 to 4,

r3 is an integer of 0 to 6,

When r1 to r5 are each 2 or more, the structures in parentheses are the same or different from each other.

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 heterocyclic 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; A substituted or unsubstituted arylamine group, or a bond 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; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group, or a bond 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; A heterocyclic group, or bonded to 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 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 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; Substituted or unsubstituted arylene having 1 to 4 rings; Or a substituted or unsubstituted heteroarylene of 1 to 3 rings.

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

According to one embodiment of the present disclosure, L are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene; Or a mono- to tricyclic substituted or unsubstituted heteroarylene containing at least one of N, O and S. [

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 arylene.

According to one embodiment of the present disclosure, L is a direct bond; Substituted or unsubstituted phenylene; A substituted or unsubstituted anthracenylene group; Or a substituted or unsubstituted heteroarylene group containing at least one N atom.

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

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

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

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

According to one embodiment of the present disclosure, r is an integer of 0 or 1.

According to one embodiment of the present disclosure, r is one.

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

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

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

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

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

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

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

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

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

In one embodiment of the present invention, the light emitting layer comprises a compound of the general formula (1), and further comprises a luminescent dopant.

In another embodiment, the luminescent dopant comprises a phosphorescent dopant.

In another embodiment, the phosphorescent dopant comprises an iridium phosphorescent dopant.

In another embodiment, the phosphorescent dopant material is Ir (ppy) ₃ .

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.

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, 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 with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

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

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

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

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

< Manufacturing example >

PREPARATION EXAMPLE 1 Preparation of [Compound 1-5]

[Compound A-1] [Compound A]

The carbazole (16.7 g, 100 mmol) was dissolved in 200 mL dry THF under nitrogen and cooled to -78 < 0 > C. n-BuLi (75 mL, 120 mmol, 1.6 M in hexane) was slowly dropped. After 1 hour, dichloro (4-chlorophenyl) phosphane (10.8 g, 50 mmol) was slowly added thereto, stirred for 1 hour, and then cooled to room temperature. After 300 mL of water was added, the organic layer was extracted, treated with MgSO ₄ , and filtered. The filtrate was distilled under reduced pressure to prepare [Compound A-1]. (15.1 g, yield 63%, MS: [M + H] < ⁺ > = 475)

[Compound A-1] (15.1 g, 32 mmol) was dissolved in 200 mL of CHCl ₃ , and H ₂ O ₂ (30 wt%, 100 mL) was slowly added dropwise at 0 ° C. After 12 hours, the reaction solution was diluted with 200 mL of a saturated aqueous NaHSO ₃ solution. The organic layer was filtered through MgSO ₄ treatment. The filtrate was distilled under reduced pressure and then purified by column chromatography to obtain [Compound A]. (13.3 g, 27 mmol, yield 84%, MS: [M + H] < ⁺ > = 491)

Compound A (10.0 g, 20 mmol) and triphenylene-2-ylboronic acid (5.7 g, 21 mmol) were added to 150 mL of dioxane. 75 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, 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 1-5]. (10.8 g, yield 79%, MS: [M + H] < ⁺ > = 683)

PREPARATION EXAMPLE 2 Preparation of [Compound 1-9]

Compound A (10.0 g, 20 mmol) and (9,9-diphenyl-9H-fluoren-2-yl) boronic acid (7.4 g, 20 mmol) were added to 150 mL of dioxane. 75 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, 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 1-9]. (19.9 g, yield 75%, MS: [M + H] < ⁺ > = 773)

PREPARATION EXAMPLE 3 Preparation of [Compound 1-15]

[Compound B]

11H-benzo [a] carbazole was prepared in the same manner as in [Preparation Example 1] using [Compound B]. (Yield: 45%, MS: [M + H] < ⁺ > = 592)

Compound B (10 g, 17 mmol) and phenylboronic acid (2.0 g, 17 mmol) were added to 100 mL of dioxane. 50 mL of 2.0 MK ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 7 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 1-15]. (7.5 g, yield 70%, MS: [M + H] < ⁺ > = 633)

PREPARATION EXAMPLE 4 Preparation of [Compound 1-32]

[Compound C]

11H-benzo [b] carbazole was prepared in the same manner as in <Preparation Example 1> to prepare [Compound C]. (Yield: 43%, MS: [M + H] < ⁺ > = 592)

Compound C (10 g, 17 mmol) and pyrene-1-ylboronic acid (4.2 g, 17 mmol) were added to 100 mL of dioxane. 50 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 8 hours. The mixture was cooled to room temperature, filtered and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 1-32]. (8.8 g, yield 68%, MS: [M + H] < ⁺ > = 757)

PREPARATION EXAMPLE 5 Preparation of [Compound 1-41]

[Compound D]

11H-benzo [b] < / RTI > carbazole was prepared using the method of Preparation Example 1 above to give [Compound D]. (Yield: 43%, MS: [M + H] < ⁺ > = 592)

Compound D (10 g, 17 mmol) and phenanthrene-9-yl boronic acid (3.8 g, 17 mmol) were added to 100 mL of dioxane. 50 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 8 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 1-41]. (7.9 g, yield 63%, MS: [M + H] < ⁺ > = 733)

PREPARATION EXAMPLE 6 Preparation of [Compound 1-68]

Compound A (10.0 g, 20 mmol) and (10-phenylanthracen-9-yl) boronic acid (6.0 g, 20 mmol) were added to 150 mL of dioxane. 75 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, 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 1-68]. (10.1 g, yield 71%, MS: [M + H] < ⁺ > = 709)

PREPARATION EXAMPLE 7 Preparation of [Compound 2-5]

Compound A (10.0 g, 20 mmol) and 2-phenyl-9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 10-phenanthroline (9.2 g, 20 mmol) was added to 150 mL of dioxane. 75 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 8 hours. The mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-5]. (9.6 g, yield 65%, MS: [M + H] < ⁺ > = 787)

PREPARATION EXAMPLE 8 Preparation of [Compound 2-9]

Compound A (10.0 g, 20 mmol) and (4- (pyridin-3-yl) phenyl) boronic acid (4.0 g, 20 mmol) were added to 150 mL of dioxane. 75 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 8 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-9]. (9.6 g, yield 79%, MS: [M + H] < ⁺ > = 610)

PREPARATION EXAMPLE 9 Preparation of [Compound 2-17]

Benzo [d] imidazol-2-yl) phenyl) boronic acid (5.3 g, 17 mmol) was added to 100 mL of dioxane. 50 mL of 2.0 MK ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 7 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-17]. (8.4 g, yield 60%, MS: [M + H] < ⁺ > = 825)

PREPARATION EXAMPLE 10 Preparation of [Compound 2-39]

Compound C (10 g, 17 mmol) and 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (7.4 g, 17 mmol) was added to 100 mL of dioxane. 50 mL of 2.0 MK ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 7 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-39]. (8.7 g, yield 59%, MS: [M + H] < ⁺ > = 863)

PREPARATION EXAMPLE 11 Preparation of [Compound 2-60]

Compound D (10 g, 17 mmol) and (4- (quinolin-8-yl) phenyl) boronic acid (4.2 g, 17 mmol) were added to 100 mL of dioxane. 50 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, 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 2-60]. (10.8 g, yield 71%, MS: [M + H] < ⁺ > = 760)

PREPARATION EXAMPLE 12 Preparation of [Compound 2-74]

[Compound E]

9H-dibenzo [a, c] carbazole was prepared using the method of Preparation Example 1 above. (Yield: 45%, MS: [M + H] < ⁺ > = 691)

Yl) phenyl) pyridine (4.2 g, 15 mmol) was added to a solution of the compound E (10 g, 15 mmol) and 2- (4- (4,5-tetramethyl- Was added to 100 mL of dioxane. After charging 50 mL of 2.0 MK ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ , the mixture was refluxed with stirring for 8 hours. The mixture was cooled to room temperature, filtered and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-74]. (8.0 g, yield 66%, MS: [M + H] < ⁺ > = 810)

PREPARATION EXAMPLE 13 Preparation of [Compound 2-89]

Compound A (10.0 g, 20 mmol) and (4- (dibenzo [b, d] furan-4-yl) phenyl) boronic acid (5.8 g, 20 mmol) were added to 150 mL of dioxane. 75 ml of 2.0 M K ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 8 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-89]. (10.1 g, yield 72%, MS: [M + H] < ⁺ > = 699)

PREPARATION EXAMPLE 14 Preparation of [Compound 2-97]

Compound B (10 g, 17 mmol) and (4- (benzo [d] oxazol-2-yl) phenyl) boronic acid (4.1 g, 17 mmol) were added to 100 mL of dioxane. 50 mL of 2.0 MK ₃ CO ₄ and 0.1 g of Pd (PtBu ₃ ) ₂ were added, and the mixture was refluxed for 7 hours. The solution was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 2-97]. (8.5 g, yield 67%, MS: [M + H] < ⁺ > = 750)

< 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) / Alq ₃ (30 nm) using CBP as a host on the prepared ITO transparent electrode. / LiF (1 nm) / Al (200 nm) were fabricated in this order to produce an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) 3, CBP and BCP are as follows.

< Example 1-1>

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

< Example 1-2>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 1-9] was used in place of CBP in <Comparative Example 1-1>.

< Example 1-3>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 1-15] was used in place of CBP in <Comparative Example 1-1>.

< Example 1-4>

An organic light emitting device was prepared in the same manner as in <Comparative Example 1-1>, except that [Compound 1-32] was used in place of CBP in <Comparative Example 1-1>.

< Example 1-5>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 1-41] was used in place of CBP in <Comparative Example 1-1>.

< Example 1-6>

An organic light emitting device was fabricated in the same manner as in <Comparative Example 1-1>, except that [Compound 2-89] was used instead of CBP in the above <Comparative Example 1-1>.

When an electric current was applied to the organic light-emitting device fabricated by the example 1-1 to the example 1-6 and the comparative example 1-1, the results shown in the following Table 1 were obtained

Voltage
(V) efficiency
(V @ 10 mA / cm ² ) Emission peak
(nm) Example 1-1 5.92 45.2 516 Examples 1-2 5.62 45.9 517 Example 1-3 5.73 47.9 518 Examples 1-4 5.59 48.3 517 Examples 1-5 5.69 44.9 516 Examples 1-6 5.59 46.8 517 Comparative Example 1-1 7.32 33.8 516

As shown in Table 1, the green organic light emitting devices of Examples 1-1 to 1-6 using the compound according to one embodiment of the present invention as a host material of the light emitting layer were composed of CBP Was superior to the green organic light emitting device of < Comparative Example 1-1 > using current efficiency and driving voltage.

< Example 2-1>

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

A glass substrate coated with ITO (indium tin oxide) having a thickness of 500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product 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.

The following compound [HI-A] was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 600 Å to form a hole injection layer. The following compound [HAT] (50 Å) and the following compound [HT-A] (600 Å) were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vapor-deposited at a weight ratio of 25: 1 on the hole transport layer to a thickness of 200 ANGSTROM to form a light emitting layer.

[Compound 2-5] and the following compound [LiQ] (Lithium quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum having a thickness of 1,000 Å were sequentially deposited on the electron injecting and transporting layer to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 < ^-8 > torr to produce an organic light emitting device.

[LINE]

[HI-A] [BD]

[HT-A] [BH]

[LiQ] [ET-A]

[ Example 2-2]

An organic luminescent device was fabricated in the same manner as in [Example 2-1] except that [Compound 2-9] was used in place of [Compound 2-5] in [Example 2-1].

[ Example 2-3]

An organic luminescent device was fabricated in the same manner as in [Example 2-1] except that [Compound 2-17] was used in place of [Compound 2-5] in [Example 2-1].

[ Example 2-4]

An organic luminescent device was fabricated in the same manner as in [Example 2-1] except that [Compound 2-39] was used in place of [Compound 2-5] in [Example 2-1].

[ Example 2-5]

An organic luminescent device was fabricated in the same manner as in [Example 2-1] except that [Compound 2-60] was used in place of [Compound 2-5] in [Example 2-1].

[ Example 2-6]

An organic luminescent device was fabricated in the same manner as in [Example 2-1] except that [Compound 2-74] was used in place of [Compound 2-5] in [Example 2-1].

[ Example 2-7]

An organic luminescent device was fabricated in the same manner as in [Example 2-1] except that [Compound 2-97] was used in place of [Compound 2-5] in [Example 2-1].

[ Comparative Example 2-1]

An organic luminescent device was fabricated in the same manner as in [Example 2-1] except that [ET-A] was used instead of [Compound 2-5] in [Example 2-1].

The driving voltage and the luminous efficiency of the organic light emitting device manufactured by the above-described method were measured at a current density of 10 mA / cm ² .

Voltage (V) Efficiency (Cd / A) The color coordinates (x, y) Example 2-1 5.21 5.68 (0.143, 0.105) Example 2-2 5.32 5.56 (0.143, 0.106) Example 2-3 5.25 5.49 (0.143, 0.107) Examples 2-4 5.18 5.38 (0.143, 0.105) Example 2-5 5.22 5.48 (0.143, 0.107) Examples 2-6 5.35 5.88 (0.143, 0.106) Examples 2-7 5.42 5.77 (0.143, 0.106) Comparative Example 2-1 6.20 4.81 (0.143, 0.107)

From the results of the above table, the compound represented by the formula (1) according to the present invention can be used for an organic layer capable of simultaneously injecting electrons and transporting electrons of an organic light emitting device. In the case of an organic light emitting device using the same, the device has a low driving voltage and a high efficiency, and stability of the device can be improved by hole stability of the compound.

Particularly, the compound represented by the formula (1) according to the present invention is excellent in thermal stability and can be mixed with an n-type dopant when used in an organic layer capable of electron injection and electron transport at the same time.

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

A compound represented by the following formula (2):
(2)

In Formula 2,
Provided that at least one of R ₁ to R ₄ is adjacent to two or more substituents bonded to each other to form a ring,
L are the same or different and are each independently a direct bond; Or a phenylene group,
Ar represents a phenyl group; Phenanthrene; Triphenylene group; Pyrenyl; A diphenylfluorene group; Anthracene group substituted with phenyl group; A benzoimidazole group substituted with a phenyl group; A phenanthroline group substituted with a phenyl group; A pyrimidine group substituted with a phenyl group; A pyridine group; A quinoline group; Benzoxazole group; Or a dibenzofurane group,
a, b, c and d are the same or different and each is an integer of 2 to 4,
r is an integer of 0 to 3, and when r is 2 or more, L is the same or different from each other.

delete

The compound according to claim 1, wherein the formula (2) is represented by any one of the following formulas (3) to (11):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas 3 to 11, the definitions of R ₁ , R _2, R ₄ , a, b and d are the same as those in formula (2)
X is

, The definition of L, r, and Ar is the same as in formula (2)
R < ₁₂ > and R < ₁₃ &
b ₁ and c ₁ are the same as or different from each other and each independently an integer of 0 to 6;

The compound according to claim 1, wherein the compound of formula (2) is represented by any one of the following formulas (12) to (16):
[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

In Formulas 12 to 16,
The definition of R ₁ , R _2, R ₄ , a, b and d is the same as in formula (2)
X is

, The definition of L, r, and Ar is the same as in formula (2)
R ₂₁ to R ₂₅ are hydrogen,
r1, r2, r4 and r5 are the same or different and each independently represents an integer of 0 to 4,
r3 is an integer of 0 to 6;

2. The compound according to claim 1, wherein the compound of formula 2 is selected from the following formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1 to 6 to 8 Lt; / RTI >

[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.