KR101913458B1

KR101913458B1 - Compound having double spiro structure and organic light emitting device comprising the same

Info

Publication number: KR101913458B1
Application number: KR1020150057407A
Authority: KR
Inventors: 차용범; 김진주
Original assignee: 주식회사 엘지화학
Priority date: 2015-04-23
Filing date: 2015-04-23
Publication date: 2018-10-30
Also published as: KR20160126399A

Abstract

The present invention provides a double spiro compound and an organic light emitting device including the same.

Description

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

TECHNICAL FIELD The present invention relates to a double spiro 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

In this specification, a double spiro type compound and an organic light emitting device including the same are described.

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

[Chemical Formula 1]

In Formula 1,

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

a is an integer of 0 to 8,

b is an integer of 0 to 7,

c is an integer of 0 to 5,

d is an integer of 0 to 4,

When a, b, c, and d are each 2 or more, the structures in parentheses are the same or different.

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. More preferably, the compounds described in this specification exhibit low voltage, high efficiency and / or long life characteristics when used as a material for hole injection, hole transport, and electron inhibition 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; A hydroxy group; A carbonyl group; An ester group; Imide; An amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; A silyl group substituted or unsubstituted with an alkyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. 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.

In one embodiment of the present disclosure, the expression " substituted or unsubstituted " is preferably selected from the group consisting of deuterium; A halogen group; A nitrile group; An alkyl group; A trimethylsilyl group; An aryl group; And a heterocyclic group, which may be substituted or unsubstituted.

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

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

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

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

In the present specification, the silyl group may be represented by the formula of -SiRR'R ", wherein R, R 'and R " are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BRR'R ", wherein R, R 'and R " are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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

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

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, 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 containing two or more 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.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

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 heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group containing at least two heterocyclic groups may contain a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

In the present specification, the arylheteroarylamine group means an aryl group and an amine group substituted with a heterocyclic group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine 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.

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, a fluorenyl group and a triphenylene group.

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

When the fluorenyl group is substituted,

, ,

,

,

,

,

And

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

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazyl group And dibenzofuranyl groups, but are not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, the alkylaryl group, the arylamine group and the arylheteroarylamine group, The description of one aryl group may be applied.

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

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

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

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

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

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

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

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

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

(2)

In Formula 2,

The definition of R2 to R4, b, c and d is the same as in formula (1)

R11 is the same as R1 to R4,

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

Ar1 and Ar2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

p is an integer of 1 to 8,

f is an integer of 0 to 8,

1? P + f? 8,

m is an integer of 1 to 10,

When p, f, and m are each 2 or more, the structures in parentheses are the same or different.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (3) and (4).

(3)

[Chemical Formula 4]

In the above formulas (3) and (4)

The definition of R2 to R4, b, c and d is the same as in formula (1)

L1 and L2 are the same or different from each other and are each independently a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

Ar1 to Ar4, Y1 and Y2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

y1 is an integer of 0 to 7,

y2 is an integer of 0 to 6,

m1 and m2 are the same or different and each independently an integer of 1 to 10,

When y1, y2, m1, and m2 are each 2 or more, the structures in parentheses are the same or different.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (5) to (7).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In Formulas 5 to 7,

The definition of R2 to R4, b, c and d is the same as in formula (1)

L1 is a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

Ar1, Ar2 and Y1 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

y1 is an integer of 0 to 7,

When y1 and m1 are each 2 or more, the structures in parentheses are the same or different from each other.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (8) to (10).

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the general formulas (8) to (10)

The definition of R2 to R4, b, c and d is the same as in formula (1)

y1 is an integer of 0 to 7,

y2 is an integer of 0 to 6,

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (11) to (13).

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above formulas 11 to 13,

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

The definition of R11 is the same as that of R2 to R4,

L, L11 and L21 are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

Ar11, Ar12, Ar21 and Ar22 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to adjacent groups to form a substituted or unsubstituted ring,

p is an integer of 1 to 8,

f is an integer of 0 to 8,

1? P + f? 8,

m, m11 and m12 are the same or different and each independently an integer of 1 to 10,

When p, f, m, m11 and m21 are each 2 or more, the structures in parentheses are the same or different from each other.

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

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

According to one embodiment of the present invention, L, L 1 and L 2 are the same or different and are each independently a direct bond; Substituted or unsubstituted phenylene; A substituted or unsubstituted divalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent quaterphenyl group; A substituted or unsubstituted divalent naphthyl group; A substituted or unsubstituted divalent anthracenyl group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent phenanthryl group; A substituted or unsubstituted divalent pyrenyl group; A substituted or unsubstituted divalent crysinyl group.

According to one embodiment of the present invention, L, L 1 and L 2 are the same or different and are each independently a direct bond; Phenylene; A divalent biphenyl group; A divalent terphenyl group; A bivalent quaterphenyl group; A divalent naphthyl group; A divalent anthracenyl group; A divalent fluorenyl group; A divalent phenanthryl group; A divalent pyrenyl group; Divalent crycenyl group.

According to one embodiment of the present invention, L, L 1 and L 2 are the same or different and are each independently substituted or unsubstituted heteroarylene.

According to an embodiment of the present invention, L, L 1 and L 2 may be the same or different from each other, and each may independently be any one selected from the following structures.

In the above formula,

A1 and A2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to each other to form a substituted or unsubstituted ring,

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

In the above formula,

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

In the above formula,

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted 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, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted 1 to 10 ring aryl group; Or a substituted or unsubstituted 1-to 10-membered heterocyclic 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 1 to 9-membered aryl group; Or a substituted or unsubstituted 1 to 6-membered heterocyclic group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted monocyclic to bicyclic aryl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other, and each independently selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, An alkoxy group, an aryloxy group, an alkylthio group, an arylthioxy group, an alkylsulfoxy group, an arylsulfoxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, An aryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group; An aryl group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxy group, an arylthio group, an arylthio group, an arylthio group, an alkylthio group, an arylthio group, an arylthio group, An alkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylamine group, an arylamine group, an arylamine group, A heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group, an aryl group, a heterocyclic group,

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and each independently selected from the group consisting of deuterium, halogen, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, An aryl group substituted or unsubstituted with a substituent selected from the group consisting of a phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group selected from the group consisting of hydrogen, halogen, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, Or a substituted or unsubstituted heterocyclic 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 quaterphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted crecenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted phenanthryl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and each independently selected from the group consisting of deuterium, halogen, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, A phenyl group substituted or unsubstituted with a substituent selected from the group consisting of a phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted biphenyl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted naphthyl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Substituted or unsubstituted anthracenyl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted thienyl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted terphenyl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted quaterphenyl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group selected from the group consisting of hydrogen, halogen, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, Or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and are each independently a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different from each other and each independently selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a trimethylsilyl group, an aryl group and a heterocyclic group An aryl group which is substituted or unsubstituted with at least one substituent; Or a heterocyclic group substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium, halogen, nitrile, alkyl, trimethylsilyl, aryl, and heterocyclic groups.

According to one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently substituted with at least one substituent selected from the group consisting of a deuterium, a halogen group, a nitrile group, an alkyl group, and a silyl group substituted with an alkyl group Or an unsubstituted phenyl group; Naphthyl group; A biphenyl group; A terphenyl group; Tetraphenyl group; A fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group; A phenanthryl group; Triphenylene group; A dibenzofuranyl group; A dibenzothiophene group; A carbazolyl group substituted or unsubstituted with an aryl group; Or a benzocarbazole group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and are each independently a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently a substituted or unsubstituted monocyclic to tricyclic heterocyclic group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted monocyclic to fused heterocyclic group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted monocyclic to bicyclic heterocyclic group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently a substituted or unsubstituted 2-to 6-membered heterocyclic group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently is a substituted or unsubstituted heterocyclic group having 3 to 6 rings.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted pyrrol group; A substituted or unsubstituted imidazole group; A substituted or unsubstituted thiazole group; A substituted or unsubstituted oxazole group; A substituted or unsubstituted oxadiazole group; A substituted or unsubstituted triazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted bipyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted triazole group; A substituted or unsubstituted acridyl group; A substituted or unsubstituted pyridazine group; A substituted or unsubstituted pyrazinyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted quinoxalinyl group; A substituted or unsubstituted phthalazinyl group; A substituted or unsubstituted pyridopyrimidinyl group; A substituted or unsubstituted pyridopyrimidinyl group; A substituted or unsubstituted pyrazinopyrazinyl group; A substituted or unsubstituted isoquinoline group; A substituted or unsubstituted indole group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzofuranyl group; Substituted or unsubstituted phenanthroline; A substituted or unsubstituted thiazolyl group; A substituted or unsubstituted isoxazolyl group; A substituted or unsubstituted oxadiazolyl group; A substituted or unsubstituted thiadiazolyl group; A substituted or unsubstituted benzothiazolyl group; A substituted or unsubstituted phenothiazinyl group; Or a substituted or unsubstituted dibenzofuranyl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other, and each independently represents a thiophene group; Furan group; A roll roll; Imidazole group; Thiazole group; An oxazole group; An oxadiazole group; Triazole group; A pyridyl group; A bipyridyl group; Pyrimidyl; Triazine; Triazole group; Acridyl group; Pyridazine group; A pyrazinyl group; A quinolinyl group; A quinazoline group; A quinoxalinyl group; A phthalazinyl group; A pyridopyrimidinyl group; A pyridopyranyl group; A pyrazinopyrazinyl group; An isoquinoline group; Indole group; Carbazole group; Benzoxazole group; Benzimidazole group; Benzothiazole group; Benzocarbazole group; Benzothiophene group; A dibenzothiophene group; A benzofuranyl group; Phenanthroline; A thiazolyl group; An isoxazolyl group; An oxadiazolyl group; A thiadiazolyl group; Benzothiazolyl group; A phenothiazinyl group; Or a dibenzofuranyl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently a substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted triazine group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted indolocarbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinoxalinyl group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted silyl group; A bicyclic substituted or unsubstituted heterocyclic group containing at least one of N, S and O; A tricyclic substituted or unsubstituted heterocyclic group containing at least two of N, O and S; A substituted or unsubstituted heterocyclic group of four rings including at least one of S and O; Or a 5-or 6-membered substituted or unsubstituted heterocyclic group containing N or more.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other, and each independently represents a pyridyl group; Pyrimidyl; Triazine; Carbazole group; Indolocarbazole group; Benzocarbazole group; Thiophene group; A furanyl group; A dibenzothiophene group; A dibenzofuranyl group; A quinoline group; A quinoxalinyl group; A quinazoline group; Phosphine oxide groups; Silyl group; A bicyclic heterocyclic group containing at least one of N, S and O; A tricyclic heterocyclic group containing at least two of N, O and S; A 4-membered heterocyclic group containing at least one of S and O; Or a 5-or 6-membered heterocyclic group containing N or more.

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 quaterphenyl group; A substituted or unsubstituted 1-naphthyl group; A substituted or unsubstituted 2-naphthyl group; A substituted or unsubstituted 2-fluorenyl group; A substituted or unsubstituted 3-fluorenyl group; A substituted or unsubstituted 4-fluorenyl group; A substituted or unsubstituted 2-phenanthryl group; A substituted or unsubstituted 3-phenanthryl group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted 9-phenanthryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently a substituted or unsubstituted 2-dibenzothiophene group; A substituted or unsubstituted 2-dibenzofuranyl group; A substituted or unsubstituted 4-dibenzofuranyl group; A substituted or unsubstituted N-carbazole group; A substituted or unsubstituted 1-carbazole group; A substituted or unsubstituted 2-carbazole group; A substituted or unsubstituted 3-carbazole group; A substituted or unsubstituted a-benzocarbazole group; Or a substituted or unsubstituted c-benzocarbazole group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other, and are each independently a phenyl group; A biphenyl group; A terphenyl group; A quaterphenyl group; A 1-naphthyl group; A 2-naphthyl group; A 2-fluorenyl group; A 3-fluorenyl group; A 4-fluorenyl group; A 2-phenanthryl group; Triphenylene group; A 3-phenanthryl group; Or a 9-phenanthryl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and each independently represent a 2-dibenzothiophene group; A 2-dibenzofuranyl group; A 4-dibenzofuranyl group; N-carbazole group; 1-carbazole group; A 2-carbazole group; 3-carbazole group; a-benzocarbazole group; Or a c-benzocarbazole group.

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

According to one embodiment of the present invention, Ar1 to Ar4 may be the same or different from each other and each independently selected from the following structures.

According to one embodiment of the present disclosure,

May be any one selected from the following structures.

According to one embodiment of the present disclosure,

May be any one selected from the following structures.

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

The compound represented by the above formula (1) can be produced based on the following production example. According to one embodiment, it can be prepared by following the steps of Scheme 1-1 and 1-2.

[Reaction Scheme 1-1] (Compound A, Compound B, and Compound C)

[Reaction Scheme 1-2]

[Reaction 1 - 3]

In the above Schemes 1-1 to 1-3,

X is halogen, and the definitions of Ar1 and Ar2 are the same as those in formula (1).

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

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

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

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 arylamine groups, such as pyrene, anthracene, chrysene, and ferriflantene having an arylamine group. Examples of the styrylamine compound include substituted or unsubstituted Substituted arylamine in which at least one aryl vinyl group is substituted, wherein at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine 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 an 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.

< Synthetic example 1>

<Production Example 1> Synthesis of Compound 1-1

Compound A (15.0 g, 0.27 mol) and diphenylamine (4.99 g, 0.29 mol) were dissolved in 240 ml of xylene in a 500 ml round-bottomed flask under nitrogen atmosphere and sodium tert-butoxide (3.09 g, 0.32 mol) tert- butylphosphine) palladium (0) (0.07 g, 0.0013 mol) was added thereto, followed by heating with stirring for 1 hour. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to obtain the compound 1-1 (15.64 g, yield: 91%).

MS [M + H] < ⁺ > = 648

<Preparation Example 2> Synthesis of compound 1-5 to compound

Compound A (15.0 g, 0.27 mol) and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (8.42 g, 0.29 mol) were completely dissolved in 260 ml of xylene in a 500 ml round- tert-butoxide (3.09 g, 0.32 mol) was added, and bis (tri- tert- butylphosphine) palladium (0) (0.07 g, 0.0013 mol) was added and the mixture was heated with stirring for 2 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to obtain the above compound 1-5 (18.45 g, yield: 89%).

MS [M + H] < ⁺ > = 764

<Production Example 3> Synthesis of Compound 1-6

Compound A (15.0 g, 0.27 mol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- g, 0.29mol), and then completely dissolved in Xylene 260ml was added to the sodium tert-butoxide (3.09g, 0.32mol ) , insert a Bis (tri- tert -butylphosphine) palladium ( 0) (0.07g, 0.0013mol) 3 Lt; / RTI > The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to obtain the compound 1-6 (20.11 g, yield: 89%).

MS [M + H] < ⁺ > = 840

<Production Example 4> A compound of Compound 1-7 Synthesis

Compound A (15.0 g, 0.27 mol) and N-phenyl- [1,1'-biphenyl] -4-amine (7.24 g, 0.29 mol) were completely dissolved in 220 ml of xylene in a 500 ml round- -butoxide (3.09 g, 0.32 mol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.07 g, 0.0013 mol) was added and the mixture was heated with stirring for 2 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure, and recrystallized from ethyl acetate (280 ml) to obtain the compound 1-7 (20.11 g, yield: 89%).

MS [M + H] < ⁺ > = 724

<Production Example 5> A compound of the compound 1-10 Synthesis

Compound A (15.0 g, 0.27 mol) and di ([1,1'-biphenyl] -4-yl) amine (9.49 g, 0.29 mol) were completely dissolved in 220 ml of xylene in a 500 ml round- -butoxide (3.09 g, 0.32 mol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.07 g, 0.0013 mol) was added and the mixture was heated with stirring for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (350 ml) to obtain Compound 1-10 (20.11 g, yield: 89%).

MS [M + H] < ⁺ > = 800

<Production Example 6> A compound of the compound 1-13 Synthesis

Compound A (15.0 g, 0.27 mol) and di ([1,1'-biphenyl] -4-yl) amine (9.49 g, 0.29 mol) were completely dissolved in 220 ml of xylene in a 500 ml round- -butoxide (3.09 g, 0.32 mol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.07 g, 0.0013 mol) was added and the mixture was heated with stirring for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (350 ml) to obtain the compound 1-13 (19.87 g, yield: 87%).

MS [M + H] < ⁺ > = 800

<Production Example 7> A compound of the compound 1-16 Synthesis

Compound A (15.0 g, 0.27 mol) and N - ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -2-amine (0.09g, 0.0013mol) of bis (tri- tert- butylphosphine) palladium (0) was added to the reaction mixture for 3 hours Lt; / RTI > The temperature was lowered to room temperature, the base was removed by filtration, the xylene was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate (300 ml) to obtain the compound 1-16 (16.44 g, yield: 80%).

MS [M + H] < ⁺ > = 800

<Production Example 8> A compound of the compound 1-17 Synthesis

Compound A (15.0 g, 0.27 mol) and N - ([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren- g, 0.29mol), and then completely dissolved in Xylene 200ml was added to the sodium tert-butoxide (3.09g, 0.32mol ) , insert a Bis (tri- tert -butylphosphine) palladium ( 0) (0.07g, 0.0013mol) 3 Lt; / RTI > The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to obtain the compound 1-17 (18.91 g, yield: 85%).

MS [M + H] < ⁺ > = 840

<Production Example 9> A compound of the compound 1-20 Synthesis

Compound A (15.0 g, 0.27 mol), N - ([1,1'-biphenyl] -2-yl) -9,9-dimethyl-9H-fluoren- g, 0.29mol), and then completely dissolved in Xylene 200ml was added to the sodium tert-butoxide (3.09g, 0.32mol ) , insert a Bis (tri- tert -butylphosphine) palladium ( 0) (0.07g, 0.0013mol) 3 Lt; / RTI > The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (450 ml) to obtain the compound 1-20 (20.45 g, yield 92%).

MS [M + H] < ⁺ > = 874

<Production Example 10> A compound of the compound 1-21 Synthesis

Compound A (15.0 g, 0.27 mol) and N - ([1,1'-biphenyl] -4-yl) phenanthren-9-amine (11.85 g, 0.29 mol) were dissolved in 200 ml of xylene in a 500 ml round- Sodium tert-butoxide (3.09 g, 0.32 mol) was added, and bis (tri- tert- butylphosphine) palladium (0) (0.07 g, 0.0013 mol) was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (450 ml) to obtain the above compound 1-21 (18.65 g, yield: 87%).

MS [M + H] < ⁺ > = 823

<Production Example 11> A compound of the compound 1-42 Synthesis

A method of preparing the above compound 1-1 except that a substance of N - ([1,1'-biphenyl] -4-yl) dibenzo [b, d] thiophen-2-amine was used instead of diphenylene in Production Example 1 Compound 1-42 was prepared in the same manner as above.

MS [M + H] < ⁺ > = 830

<Production Example 12> A compound of the compound 1-44 Synthesis

The compound 1-44 was prepared in the same manner as in the preparation of the compound 1-1, except that a substance of N-phenyldibenzo [b, d] furan-2-amine was used instead of diphenylene in Preparation Example 1.

MS [M + H] < ⁺ > = 814

<Production Example 13> A compound of the compound 1-46 Synthesis

A method for producing the compound 1-1 except that a substance of N- (9,9-dimethyl-9H-fluoren-2-yl) dibenzo [b, d] furan-2-amine was used instead of diphenylene in Production Example 1 , The compound 1-46 was prepared.

MS [M + H] < ⁺ > = 854

<Production Example 14> A compound of the compound 1-47 Synthesis

The compound 1-47 was prepared in the same manner as in the preparation of the compound 1-1 except that the compound of Preparation Example 1 was replaced with N-phenyldibenzo [b, d] thiophen-4-amine instead of diphenylene.

MS [M + H] < ⁺ > = 754

<Production Example 15> A compound of the compound 1-50 Synthesis

The compound 1-50 was prepared in the same manner as in the preparation of the compound 1-1, except that a substance of N-phenyldibenzo [b, d] furan-4-amine was used instead of diphenylene in Preparation Example 1.

MS [M + H] < ⁺ > = 738

<Production Example 16> A compound of the compound 1-65 Synthesis

Preparation of the compound 1-1 was carried out except that in Example 1, a substance was used in place of diphenylene which was N - ([1,1'-biphenyl] -4-yl) -9,9'-spirobi [fluoren] The compound 1-65 was prepared in the same manner as the compound [I-65].

MS [M + H] < ⁺ > = 862

<Production Example 17> A compound of the compound 1-71 Synthesis

The compound 1-1 was prepared in the same manner as in Production Example 1, except that a substance of N- (4- (9H-carbazol-9-yl) phenyl) - [1,1'-biphenyl] The above compound 1-71 was prepared.

MS [M + H] < ⁺ > = 889

<Example 18> A compound of the compound 1-78 Synthesis

The compound 1-78 was prepared in the same manner as in the preparation of the compound 1-1, except that the compound of Preparation Example 1 was replaced by N, 9-diphenyl-9H-carbazol-3-amine instead of diphenylene.

MS [M + H] < ⁺ > = 813

<Production Example 19> A compound of the compound 1-83 Synthesis

The compound 1-83 was prepared by using AMINE twice in the same manner as in the preparation of the compound 1-1 except that the compound D was used instead of the compound A in Preparation Example 1.

MS [M + H] < ⁺ > = 815

<Production Example 20> A compound of compound 1-111 Synthesis

Compound 1-111 was prepared by using AMINE in duplicate in the same manner as in the preparation of Compound 1-1, except that Compound D was used instead of Compound A in Example 1 and carbazole was used instead of diphenyl.

MS [M + H] < ⁺ > = 811

<Production Example 21> A compound of compound 1-112 Synthesis

The same procedure as in the preparation of Compound 1-1 except for using 9-phenyl-9H-carbazol-3-yl) boronic acid instead of diphenyl using Compound D instead of Compound A in Preparative Example 1, -112.

MS [M + H] < ⁺ > = 963

< Manufacturing example 22>

In the same manner as in Production Examples 18 to 18, except that the starting material was Compound B instead of Compound A, the compound 2-1. 2-5. 2-6. 2-7. 2-10. 2-13. 2-16. 2-17. 2-20. 2-21. 2-42. 2-44. 2-46. 2-47. 2-50. 2-65. 2-71. 2-78.

< Manufacturing example 23>

In the same manner as in Production Examples 18 to 18, except that the starting material was Compound C instead of Compound A, the compound 3-1. 3-5. 3-6. 3-7. 3-10.3-13, 3-13. 3-16. 3-17. 3-20. 3-21. 3-42. 3-44. 3-46. 3-47. 3-50. 3-65. 3-71. 3-78.

< Experimental Example 1>

The glass substrate coated with ITO (indium tin oxide) thin film with a 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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

[NPB]

Subsequently, the following compound 1-1 was vacuum-deposited on the hole transport layer to a thickness of 100 Å to form an electron blocking layer.

[1-1]

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

[BH]

[BD]

[ET1]

[LiQ]

The compound ET1 and the 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 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

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

<Experimental Example 1-1>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-5 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-6 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-7 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-10 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-13 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-16 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-7>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-17 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-20 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-21 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-42 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-44 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-46 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-47 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-50 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-65 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-16>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-71 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-17>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-78 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-18>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-83 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-19>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-111 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-20>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-112 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-21>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-1 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-22>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-5 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-23>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-6 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-24>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-7 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-25>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-10 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-26>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound 2-13 was used instead of the compound EB1 in Experimental Example 1.

<Experimental Example 1-27>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-16 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-28>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-17 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-29>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-20 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-30>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-1 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-31>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-5 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-32>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-6 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-33>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-7 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-34>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-10 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-35>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-13 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-36>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-16 was used in place of Compound EB1 in Experimental Example 1.

<Experimental Example 1-37>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-17 was used instead of Compound EB1 in Experimental Example 1.

<Experimental Example 1-38>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 3-20 was used instead of Compound EB1 in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT1 was used in place of Compound EB1 in Experimental Example 1.

[HT1]

< Comparative Example 2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT2 was used in place of Compound EB1 in Experimental Example 1.

[HT2]

< Comparative Example 3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT3 was used in place of Compound EB1 in Experimental Example 1.

[HT3]

< Comparative Example 4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT4 was used in place of Compound EB1 in Experimental Example 1.

[HT4]

The results shown in Table 1 were obtained when current was applied to the organic light-emitting device manufactured by Experimental Example 1, Experimental Examples 1-1 to 38 and Comparative Examples 1 to 4.

compound
(Electron inhibiting layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1 Compound 1-1 3.89 6.45 (0.138, 0.127) Experimental Example 1-1 Compound 1-5 3.94 6.35 (0.139, 0.122) Experimental Example 1-2 Compound 1-6 3.85 6.36 (0.138, 0.126) Experimental Example 1-3 Compound 1-7 3.96 6.31 (0.138, 0.127) Experimental Examples 1-4 Compound 1-10 3.93 6.42 (0.137, 0.125) Experimental Examples 1-5 Compound 1-13 3.82 6.47 (0.136, 0.125) Experimental Example 1-6 Compound 1-16 3.80 6.51 (0.136, 0.127) Experimental Example 1-7 Compound 1-17 3.87 6.35 (0.136, 0.125) Experimental Examples 1-8 Compound 1-20 3.86 6.34 (0.137, 0.125) Experimental Examples 1-9 Compound 1-21 3.85 6.31 (0.138, 0.125) Experimental Example 1-10 Compound 1-42 3.85 6.33 (0.136, 0.125) Experimental Example 1-11 Compound 1-44 3.81 6.32 (0.137, 0.125) Experimental Example 1-12 Compound 1-46 3.89 6.30 (0.136, 0.125) Experimental Example 1-13 Compound 1-47 3.89 6.50 (0.138, 0.126) Experimental Example 1-14 Compound 1-50 3.84 6.52 (0.137, 0.125) Experimental Example 1-15 Compound 1-65 3.80 6.50 (0.136, 0.127) Experimental Example 1-16 Compound 1-71 3.81 6.55 (0.135, 0.127) Experimental Example 1-17 Compound 1-78 3.84 6.51 (0.138, 0.127) Experimental Example 1-18 Compound 1-83 3.78 6.59 (0.137, 0.125) Experimental Example 1-19 Compound 1-111 3.84 6.46 (0.137, 0.125) Experimental Example 1-20 Compound 1-112 3.88 6.42 (0.136, 0.125) Experimental Example 1-21 Compound 2-1 3.89 6.46 (0.138, 0.126) Experimental Example 1-22 Compound 2-5 3.81 6.44 (0.137, 0.125) Experimental Example 1-23 Compound 2-6 3.85 6.40 (0.136, 0.127) Experimental Example 1-24 Compound 2-7 3.84 6.46 (0.135, 0.127) Experimental Example 1-25 Compound 2-10 3.88 6.42 (0.137, 0.125) Experimental Example 1-26 Compound 2-13 3.89 6.46 (0.138, 0.125) Experimental Example 1-27 Compound 2-16 3.85 6.44 (0.136, 0.125) Experimental Example 1-28 Compound 2-17 3.85 6.50 (0.136, 0.127) Experimental Example 1-29 Compound 2-20 3.85 6.50 (0.136, 0.127) Experimental Example 1-30 Compound 3-1 3.88 6.42 (0.137, 0.125) Experimental Examples 1-31 Compound 3-5 3.89 6.40 (0.138, 0.125) Experimental Example 1-32 Compound 3-6 3.88 6.42 (0.137, 0.125) Experimental Example 1-33 Compound 3-7 3.89 6.40 (0.138, 0.125) Experimental Example 1-34 Compound 3-10 3.88 6.42 (0.137, 0.125) Experimental Example 1-35 Compound 3-13 3.89 6.40 (0.138, 0.125) Experimental Example 1-36 Compound 3-16 3.88 6.42 (0.137, 0.125) Experimental Example 1-37 Compound 3-17 3.89 6.40 (0.138, 0.125) Experimental Examples 1-38 Compound 3-20 3.88 6.42 (0.137, 0.125) Comparative Example 1 HT1 4.23 5.91 (0.136, 0.127) Comparative Example 2 HT2 4.27 5.95 (0.136, 0.127) Comparative Example 3 HT3 4.45 5.52 (0.135, 0.125) Comparative Example 4 HT4 4.44 5.73 (0.135, 0.130)

As shown in Table 1, in the case of the organic light emitting device prepared by using the compound of the present invention as an electron blocking layer, the compound of the present invention Exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

In Experimental Examples 1-1 to 1-35, the voltage was decreased by 10 & tilde & 20% and the efficiency was also 20% higher than those of Comparative Examples.

As shown in Table 1, it was confirmed that the compounds of the present invention are excellent in electron blocking ability and applicable to organic light emitting devices.

<Experimental Example 2>

In Experimental Example 1, the same experiment was conducted except that the compounds of Experimental Examples 1-1 to 38 were used instead of NPB as the hole transport layer.

When current was applied to the organic light-emitting device manufactured in Experimental Example 2, Experimental Examples 2-1 to 38 and Comparative Examples 1 to 4, the results shown in Table 2 were obtained.

compound
(Hole transport layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 2 Compound 1-1 4.45 5.45 (0.138, 0.127) Experimental Example 2-1 Compound 1-5 4.52 5.35 (0.139, 0.122) EXPERIMENTAL EXAMPLE 2-2 Compound 1-6 4.48 5.36 (0.138, 0.126) Experimental Example 2-3 Compound 1-7 4.59 5.39 (0.138, 0.127) Experimental Example 2-4 Compound 1-10 4.55 5.42 (0.137, 0.125) Experimental Example 2-5 Compound 1-13 4.46 5.47 (0.136, 0.125) Experimental Examples 2-6 Compound 1-16 4.48 5.51 (0.136, 0.127) Experimental Example 2-7 Compound 1-17 4.53 5.35 (0.136, 0.125) Experimental Examples 2-8 Compound 1-20 4.49 5.34 (0.137, 0.125) Experimental Examples 2-9 Compound 1-21 4.52 5.38 (0.138, 0.125) Experimental Example 2-10 Compound 1-42 4.54 5.46 (0.136, 0.125) Experimental Example 2-11 Compound 1-44 4.46 5.36 (0.137, 0.125) Experimental Examples 2-12 Compound 1-46 4.41 5.31 (0.136, 0.125) Experimental Example 2-13 Compound 1-47 4.50 5.50 (0.138, 0.126) Experimental Example 2-14 Compound 1-50 4.43 5.52 (0.137, 0.125) Experimental Example 2-15 Compound 1-65 4.57 5.58 (0.136, 0.127) Experimental Example 2-16 Compound 1-71 4.56 5.55 (0.135, 0.127) Experimental Example 2-17 Compound 1-78 4.44 5.51 (0.138, 0.127) Experimental Example 2-18 Compound 1-83 4.41 5.59 (0.137, 0.125) Experimental Example 2-19 Compound 1-111 4.58 5.46 (0.137, 0.125) Experimental Example 2-20 Compound 1-112 4.49 5.45 (0.136, 0.125) Experimental Example 2-21 Compound 2-1 4.57 5.46 (0.138, 0.126) Experimental Example 2-22 Compound 2-5 4.52 5.44 (0.137, 0.125) Experimental Example 2-23 Compound 2-6 4.43 5.40 (0.136, 0.127) Experimental Example 2-24 Compound 2-7 4.45 5.36 (0.135, 0.127) Experimental Example 2-25 Compound 2-10 4.57 5.42 (0.137, 0.125) Experimental Example 2-26 Compound 2-13 4.46 5.46 (0.138, 0.125) Experimental Example 2-27 Compound 2-16 4.54 5.44 (0.136, 0.125) EXPERIMENTAL EXAMPLE 2-28 Compound 2-17 4.53 5.53 (0.136, 0.127) Experimental Example 2-29 Compound 2-20 4.41 5.51 (0.136, 0.127) Experimental Example 2-30 Compound 3-1 4.45 5.42 (0.137, 0.125) EXPERIMENTAL EXAMPLE 2-31 Compound 3-5 4.59 5.40 (0.138, 0.125) Experimental Example 2-32 Compound 3-6 4.41 5.44 (0.136, 0.125) Experimental Example 2-33 Compound 3-7 4.58 5.43 (0.136, 0.127) Experimental Example 2-34 Compound 3-10 4.53 5.53 (0.136, 0.127) Experimental Example 2-35 Compound 3-13 4.53 5.53 (0.136, 0.127) Experimental Example 2-36 Compound 3-16 4.41 5.51 (0.136, 0.125) Experimental Example 2-37 Compound 3-17 4.45 5.42 (0.136, 0.127) Experimental Example 2-38 Compound 3-20 4.59 5.40 (0.136, 0.127) Comparative Example 1 HT1 5.06 4.91 (0.136, 0.127) Comparative Example 2 HT2 5.11 4.95 (0.136, 0.127) Comparative Example 3 HT3 5.18 4.52 (0.135, 0.125) Comparative Example 4 HT4 5.22 4.73 (0.135, 0.130) Comparative Example 5 HT5 5.39 4.65 (0.135, 0.130)

As shown in Table 2, when the compound of the present invention is used as a hole transport layer, the compound of the present invention plays a role of hole transport when compared with the case of using the materials of Comparative Examples 1 to 4 Exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

Specifically, in Experimental Examples 2-1 to 2-38, the voltage is decreased by 10% or more and the efficiency is also 20% or more higher than the comparative example.

As shown in Table 1, it was confirmed that the compounds according to the present invention are excellent in hole transporting ability and applicable to organic light emitting devices.

As shown in Tables 1 and 2, it was confirmed that the compounds according to the present invention are applicable not only to electron blocking ability but also to hole transporting ability and thus to organic light emitting devices.

While the present invention has been described with reference to the preferred embodiments (the electron suppressing layer and the hole transporting layer) of the present invention, the present invention is not limited thereto and various modifications can be made within the scope of the claims and the detailed description of the invention And this also belongs to the category of invention.

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

Claims

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

In Formula 1,
R1 is - (L) mN (Ar1) (Ar2); Or a heteroaryl group substituted or unsubstituted with an aryl group,
L is a direct bond; Or an arylene group substituted or unsubstituted with an alkyl group, m is an integer of 0 to 3,
Ar1 and Ar2 are the same or different and each independently represents an aryl group substituted or unsubstituted with R10; Or a heteroaryl group substituted or unsubstituted with R20,
R10 and R20 are the same as or different from each other, and each independently selected from the group consisting of deuterium; A halogen group; A nitrile group; -SiRR'R "'; An alkyl group; An aryl group substituted or unsubstituted with -SiRR'R "; Or a heteroaryl group substituted or unsubstituted with an aryl group or a heteroaryl group,
R, R 'and R " are the same or different and each independently hydrogen, an alkyl group or an aryl group,
R2 to R4 are each independently hydrogen,
a is 1 or 2,
b is an integer of 0 to 7,
c is an integer of 0 to 5,
d is an integer of 0 to 4,
when a is 2, R1 is the same or different from each other,
When b, c, and d are each 2 or more, the structures in parentheses are the same or different.

The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2:
(2)

In Formula 2,
The definition of R2 to R4, L, m, Ar1, Ar2, b, c and d is the same as in formula (1)
R11 is the same as R1,
p is 1 or 2,
f is 0 or 1,
1? P + f? 2,
When p is 2, - (L) mN (Ar1) (Ar2) are the same or different from each other.

The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (3) and (4)
(3)

[Chemical Formula 4]

In the above formulas (3) and (4)
The definition of R2 to R4, Ar1, Ar2, b, c and d is the same as in formula (1)
L1 and L2 are each independently a direct bond; Or an arylene group substituted or unsubstituted with an alkyl group,
Ar3 and Ar4 are the same or different and each independently represents an aryl group substituted or unsubstituted with R11; Or a heteroaryl group substituted or unsubstituted with R 21,
R11 and R21 are the same as or different from each other, and each independently selected from the group consisting of deuterium; A halogen group; A nitrile group; -Si (R12) (R13) (R14); An alkyl group; An aryl group substituted or unsubstituted with -Si (R12) (R13) (R14); Or a heteroaryl group substituted or unsubstituted with an aryl group or a heteroaryl group,
R12 to R14 are the same or different from each other and are each independently hydrogen, an alkyl group or an aryl group,
Y1 is a heteroaryl group substituted or unsubstituted with an aryl group,
Y2 is hydrogen,
y1 is 0 or 1,
y2 is an integer of 0 to 6,
m1 and m2 are the same or different from each other and each independently an integer of 1 to 3,
When y2, m1, and m2 are each 2 or more, the structures in parentheses are the same or different.

The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (5) to (7):
[Chemical Formula 5]

[Chemical Formula 6]

(7)

In Formulas 5 to 7,
The definition of R2 to R4, Ar1, Ar2, b, c and d is the same as in formula (1)
L1 is a direct bond; Or an arylene group substituted or unsubstituted with an alkyl group,
Y1 is a heteroaryl group substituted or unsubstituted with an aryl group,
y1 is 0 or 1,
m1 is an integer of 1 to 3,
When m1 is 2 or more, the structures in parentheses are the same or different.

The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (8) to (10):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the general formulas (8) to (10)
The definition of R2 to R4, Ar1, Ar2, b, c and d is the same as in formula (1)
L1 and L2 are the same or different from each other and are each independently a direct bond; Or an arylene group substituted or unsubstituted with an alkyl group,
Ar3 and Ar4 are the same or different and each independently represents an aryl group substituted or unsubstituted with R11; Or a heteroaryl group substituted or unsubstituted with R 21,
R11 and R21 are the same as or different from each other, and each independently selected from the group consisting of deuterium; A halogen group; A nitrile group; -Si (R12) (R13) (R14); An alkyl group; An aryl group substituted or unsubstituted with -Si (R12) (R13) (R14); Or a heteroaryl group substituted or unsubstituted with an aryl group or a heteroaryl group,
R12 to R14 are the same or different from each other and are each independently hydrogen, an alkyl group or an aryl group,
Y2 is hydrogen,
y2 is an integer of 0 to 6,
m1 and m2 are the same or different from each other and each independently an integer of 1 to 3,
When y2, m1, and m2 are each 2 or more, the structures in parentheses are the same or different.

delete

The compound according to claim 2, wherein L is the same or different and each independently is any one selected from the following structures:

In the above formula,
A1 and A2 are the same or different from each other, and each independently hydrogen; Or an alkyl group.

3. The compound according to claim 2, wherein L is a direct bond.

[5] The compound according to claim 2, wherein Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted C1-6 alkyl group substituted with at least one substituent selected from the group consisting of a deuterium, a halogen group, a nitrile group, an alkyl group, A phenyl group; Naphthyl group; A biphenyl group; A terphenyl group; Tetraphenyl group; A fluorenyl group substituted or unsubstituted with an alkyl group or an aryl group; A phenanthryl group; Triphenylene group; A dibenzofuranyl group; A dibenzothiophene group; A carbazolyl group substituted or unsubstituted with an aryl group; Or a benzocarbazole group substituted or unsubstituted with an aryl group.

3. The compound according to claim 2, wherein Ar1 and Ar2 are the same or different and each independently is any one selected from the following structures:

_

.

The compound according to claim 1, wherein the compound of formula (1) is any one 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 is a compound according to any one of claims 1 to 5 and 7 to 11, And the organic light emitting device.

13. The organic light emitting device according to claim 12, wherein the organic layer comprises a hole transporting layer, and the hole transporting layer comprises the compound.

14. The organic light emitting device according to claim 12, wherein the organic layer includes a hole injection layer, and the hole injection layer comprises the compound.

13. The organic light emitting device according to claim 12, wherein the organic layer includes an electron suppressing layer, and the electron suppressing layer comprises the compound.

[Claim 13] The organic light emitting device according to claim 12, wherein the organic layer includes a layer that simultaneously injects holes and transports holes, and the layer that simultaneously injects holes and transports the compound.