KR20190005804A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound capable of improving efficiency, and low driving voltage and/or lifespan characteristics in an organic light emitting device, and to an organic light emitting device including the same. The compound is represented by chemical formula 1. In the chemical formula 1, L is a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and a to e are each independently an integer of 0 to 3.

Description

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

This specification claims the benefit of priority based on Korean Patent Application No. 10-2017-0086611 filed with the Korean Intellectual Property Office on July 7, 2017, and all contents disclosed in the Korean patent application are incorporated herein by reference .

TECHNICAL FIELD The present invention relates to a novel 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.

In the present specification, a compound represented by the general formula (1) and an organic light emitting device containing the same are described.

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

 [Chemical Formula 1]

In Formula 1,

L is a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

R 1 to R 5 are each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; A carboxy group; Ether group; An ester group; Imide; Amide 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 silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or NRR '

Except that R1 to R5 are all hydrogen,

R and R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; A carboxy group; Ether group; An ester group; Imide; Amide 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 silyl group; A substituted or unsubstituted boron 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 heteroaryl group;

a to e each independently represents an integer of 0 to 3,

when b to e are 1 or more, adjacent R2 and R3; R3 and R4; And R4 and R5 may be bonded to each other to form a ring,

When b to e are 2 or more, each of R2 to R5 independently represents an adjacent group bonded to each other to form a ring.

One embodiment of the present disclosure is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, And a compound represented by the general 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 materials for the light emitting layer.

More specifically, the compound according to one embodiment of the present invention has a structure having a high electron accepting ability and is excellent in heat resistance, so that an appropriate deposition temperature can be maintained in the production of an organic light emitting device. In addition, since the sublimation temperature is high, it is possible to achieve high purity by the sublimation purification method, and does not cause contamination of the vapor deposition film forming apparatus or the organic light emitting device in manufacturing the organic light emitting device.

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 3, an electron transporting layer 7 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 amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; 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 this specification, " adjacent " The group may mean 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 of the substituent. 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. Alternatively, the substituent of the carbazole substituted at N and the carbazole at the 1-carbon or 8-carbon may be interpreted as " adjacent groups ".

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

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 an ester group oxygen by a straight-chain, branched or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 30 carbon atoms. 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 -SiR _a R _b R _c , wherein R _a , R _b and R _c 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 -BR _a R _b , wherein R _a and R _b 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 dimethyl boron group, a diethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group.

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, N-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2- ethylbutyl, Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1-methylpropyl, 1-methylpropyl, , 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, i-propyloxy, n-butoxy, isobutoxy, tert- n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, But is not limited thereto.

Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.

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 the present 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 40 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 number of carbon atoms of the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine 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, Group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine 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 or a substituted or unsubstituted diarylamine 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 a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, Group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, and the like.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group or a substituted or unsubstituted diheteroarylamine 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 and a fluorenyl group.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), 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, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 1 to 30. [ Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thiazolidinyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thiomorpholinyl group, an isothiazolyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl , A carbazole group, a benzocarbazole group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenazinyl group, an imidazopyridine group, a phenoxazinyl group, a phenanthroline group, a phenanthroline group, Phenothiazine group, imidazopyridine group, imidazophenanthridine group, and the like, but are not limited thereto.

In the present specification, the number of atoms constituting the ring of the heterocyclic group is 3 to 25. [ In another embodiment, the number of atoms constituting the ring of the heterocyclic group is from 5 to 17. [

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 the arylene group is a divalent group.

In the present specification, the explanation on the above-mentioned heterocyclic group can be applied except that the heteroarylene group is divalent.

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. Specific examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. But are not limited to these.

In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. Specific examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, klysene, pentacene, fluorene, indene, Thienyl, benzofluorene, spirofluorene, etc., but are not limited thereto.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing at least one hetero atom. Specific examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, Azocane, thiocaine, and the like, but are not limited thereto. In this specification, aromatic heterocyclic ring means an aromatic ring containing at least one hetero atom. Specifically, examples of the aromatic heterocycle include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole , Thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinoline, quinazoline, quinoxaline, naphthyridine Examples of the organic peroxide include at least one selected from the group consisting of at least one selected from the group consisting of pyridine, pyridine, pyridine, pyridine, pyridine, pyridine, pyrazine, pyridine, , Benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

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 compound represented by Formula 1 may be represented by Formula 2 or Formula 3 below.

(2)

(3)

In the general formulas (2) and (3)

R1a and R1b are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; Or NRR '

f is 0 to 6,

g is 0 to 3,

R2 to R5 and b to e are as defined in formula (1).

In one embodiment of the present invention, L is a direct bond; An alkylene group having 1 to 60 carbon atoms; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present invention, L is a direct bond; An alkylene group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L is a direct bond; Or a monocyclic or polycyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present invention, L is a direct bond; A substituted or unsubstituted substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted quaterphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted pyrenylene group; Or a substituted or unsubstituted fluorenylene group.

In the present specification, L is the same as or different from each other, and each independently is a direct bond or any substituent selected from the following group, but is not limited thereto and the following structures may be further substituted.

In another embodiment, R 1 to R 5 are each independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; A carboxy group; Ether group; An ester group; Imide; Amide 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 silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or NRR '.

In another embodiment, R < 1 > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or NRR '.

In another embodiment, R < 1 > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted C2-C60 heteroaryl group; Or NRR '.

In another embodiment, R < 1 > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted C2-C30 heteroaryl group; Or NRR '.

In another embodiment, R < 1 > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; A substituted or unsubstituted C2 to C20 heteroaryl group; Or NRR '.

Also according to one embodiment of the present disclosure, R 2 to R 5 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or NRR '.

In another embodiment, R 2 to R 5 are independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted C2-C60 heteroaryl group; Or NRR '.

In another embodiment, R 2 to R 5 are independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted C2-C30 heteroaryl group; Or NRR '.

In another embodiment, R 2 to R 5 are independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; A substituted or unsubstituted C2 to C20 heteroaryl group; Or NRR '.

Further, in an embodiment of the present specification, when b to e are 1 or more, adjacent R2 and R3; R3 and R4 and R4 and R5 may combine with each other to form a ring, and when b to e are 2 or more, R2 to R5 may bond to each other to form a ring.

Further, in an embodiment of the present specification, when b to e are 1 or more, adjacent R2 and R3; R3 and R4 and R4 and R5 may be bonded to each other to form a substituted or unsubstituted C3 to C60 ring; when b to e are 2 or more, R2 to R5 may be bonded to each other to form a substituted or unsubstituted A ring having 3 to 60 carbon atoms can be formed.

Further, in an embodiment of the present specification, when b to e are 1 or more, adjacent R2 and R3; R3 and R4 and R4 and R5 may bond to each other to form a substituted or unsubstituted C3-C30 ring, and when b to e are 2 or more, R2 to R5 may be bonded to each other to form a substituted or unsubstituted A ring having 3 to 30 carbon atoms may be formed.

Also, according to one embodiment of the present disclosure, it is excluded that R1 to R5 are all hydrogen. At least one of R 1 to R 5 necessarily includes a substituent other than hydrogen in the substituent described above.

Also according to one embodiment of the present disclosure, R and R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

Also according to one embodiment of the present disclosure, R and R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

Also according to one embodiment of the present disclosure, R and R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.

Also according to one embodiment of the present disclosure, R and R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; Or a substituted or unsubstituted C2-C20 heteroaryl group.

Also according to one embodiment of the present disclosure, R and R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

According to an embodiment of the present invention, R and R 'are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

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

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents into the core structure as described above. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent. Further, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Therefore, the inventors of the present invention have found that the compound of Chemical Formula 1 having such characteristics can realize lowering of the driving voltage and longevity when applied to a material for an organic light emitting diode, particularly, a light emitting layer. In addition, deposition is easy compared to a material having a low molecular weight and a high sublimation property such as F4TCNQ, and a stable interface can be formed with an electrode or an adjacent organic material layer.

The compounds of formula (I) described above can be prepared using materials and reaction conditions known in the art.

Also, the organic light emitting device according to the present invention is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers Which comprises the above compound.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

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 luminescent device of the present invention may have a structure including at least one of a hole injection layer, a hole buffer layer, a hole transport layer, an electron restraining layer, a hole blocking layer, an electron transporting layer, have. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

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.

The organic light emitting device may have a lamination structure as described below, but the present invention is not limited thereto.

(1) anode / hole transporting layer / light emitting layer / cathode

(2) anode / hole injecting layer / hole transporting layer / light emitting layer / cathode

(3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

(4) anode / hole transporting layer / light emitting layer / electron transporting layer / cathode

(5) anode / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode

(6) anode / hole injecting layer / hole transporting layer / light emitting layer / electron transporting layer / cathode

(7) anode / hole injecting layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode

(8) anode / hole injecting layer / hole buffer layer / hole transporting layer / light emitting layer / electron transporting layer / cathode

(9) anode / hole injecting layer / hole buffer layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode

(10) anode / hole transporting layer / electron blocking layer / light emitting layer / electron transporting layer / cathode

(11) anode / hole transporting layer / electron blocking layer / light emitting layer / electron transporting layer / electron injecting layer / cathode

(12) anode / hole injecting layer / hole transporting layer / electron blocking layer / light emitting layer / electron transporting layer / cathode

(13) anode / hole injecting layer / hole transporting layer / electron blocking layer / light emitting layer / electron transporting layer / electron injecting layer / cathode

(14) anode / hole transporting layer / light emitting layer / hole blocking layer / electron transporting layer / cathode

(15) anode / hole transporting layer / light emitting layer / hole blocking layer / electron transporting layer / electron injecting layer / cathode

(16) anode / hole injecting layer / hole transporting layer / light emitting layer / hole blocking layer / electron transporting layer / cathode

(17) anode / hole injecting layer / hole transporting layer / light emitting layer / hole blocking layer / electron transporting layer / electron injecting layer / cathode

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

1 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole transport layer 6, a light emitting layer 3 and a cathode 4. 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 3, an electron transporting layer 7 and a cathode 4 It is. In such a structure, the compound may be included in the light emitting layer.

The anode 2 may be any one of ITO (Indium Tin Oxide), IZO (Indium Zinc Oxide), and ZnO (Zinc Oxide) having high work function as an electrode for injecting holes. When the anode 2 is a reflective electrode, the anode 2 is formed of a reflective layer made of any one of aluminum (Al), silver (Ag), and nickel (Ni) under the layer made of any one of ITO, IZO, As shown in FIG.

The hole injection layer 5 can serve to smoothly inject holes from the anode 2 into the light emitting layer 3. [ The hole injecting layer 5 may include the compound of the above formula (1). In this case, the hole injecting layer 5 may be composed only of the compound of Formula 1, but the compound of Formula 1 may be mixed or doped with other hole injecting layer materials known in the art. The compound of Formula 1 may account for 100% of the hole injection layer, but it may be doped at 0.1 to 50% by weight. The compound of formula (1) is excellent in electron acceptance, so that power consumption can be improved and driving voltage can be lowered. The thickness of the hole injection layer 5 may be 1 nm to 150 nm. Here, when the thickness of the hole injection layer 5 is 1 nm or more, there is an advantage that the hole injection property can be prevented from being lowered. When the thickness is 150 nm or less, the hole injection layer 5 is too thick, There is an advantage that it is possible to prevent the drive voltage from rising. As the hole injection layer material, a hole injection material known in the art can be used. For example, in the group consisting of CuPc (cupper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD (N, N-dinaphthyl- Any one or more selected may be used, but the present invention is not limited thereto.

The hole transport layer 6 can play a role of facilitating the transport of holes. The hole transport layer 6 may be present in a state where other hole transport layer materials known in the art are singly, mixed, or doped. The compound of Formula 1 may account for 100% of the hole transporting layer, but it may be doped at 0.1 to 50% by weight. As the hole transport layer material, a hole transport material known in the art can be used. For example, the hole transport layer 6 may be formed by using NPD (N-dinaphthyl-N, N'-diphenylbenzidine), TPD (N, N'- benzidine, s-TAD, and MTDATA (4,4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) -triphenylamine). For example, as the hole transporting layer material, a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative and a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, A silane coupling agent, a polysilane-based compound, an aniline-based copolymer, and a conductive polymer oligomer (particularly, a thiophenol oligomer).

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer. The hole buffer layer may include the compound of Formula 1, and may include a hole injecting or transporting material known in the art. In the case where the hole buffer layer includes the compound of Formula 1, the hole blocking layer may be composed of only the compound of Formula 1, but the compound of Formula 1 may be mixed or doped with other host materials.

An electron blocking layer may be provided between the hole transporting layer and the light emitting layer, and the compound of Formula 1 or a material known in the art may be used.

The light emitting layer 3 may emit red, green, and / or blue light, and may include a compound represented by Formula 1 according to one embodiment of the present invention. Further, a material having a triplet value of 2.5 eV or more may be used together. In particular, _(difference in the singlet energy and triplet energy) ΔE _ST with a compound according to an exemplary embodiment of the present disclosure are materials having less than 0.2eV TADF (delayed fluorescence) Sensitizer having a characteristic (a triplet energy at least 2.6 eV ). Examples of materials having retardation fluorescence properties include, but are not limited to, the following.

A hole blocking layer may be provided between the electron transporting layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer 7 can play a role of facilitating transport of electrons. Materials known in the art such as Alq ₃ (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq can be used. The thickness of the electron transport layer 7 may be 1 nm to 50 nm. Here, when the thickness of the electron transport layer 7 is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered. When the thickness is 50 nm or less, the thickness of the electron transport layer 7 is too thick, There is an advantage that the driving voltage can be prevented from rising.

The electron injection layer may serve to smoothly inject electrons. May be made of _{Alq 3 (tris (8-hydroxyquinolino} ) aluminum), organic materials or complexes or metal compound known in the art, such as PBD, TAZ, spiro-PBD, BAlq or SAlq. Metal compounds include metal halides, and storage can be used, for example, can be used LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF _2, MgF _2, CaF _2, SrF _2, BaF ₂ and RaF ₂ and the like. The thickness of the electron injection layer may be 1 nm to 50 nm. If the thickness of the electron injection layer is 1 nm or more, there is an advantage that the electron injection characteristics can be prevented from being degraded. If the thickness is 50 nm or less, the thickness of the electron injection layer is too thick, There is an advantage that it can be prevented from being raised.

The cathode 4 is an electron injection electrode and may be made of magnesium (Mg), calcium (Ca), aluminum (Al), silver (Ag), or an alloy thereof having a low work function. Here, the cathode 4 may be formed to have a thickness thin enough to transmit light when the organic electroluminescent device is a front or both-side light emitting structure, and when the organic electroluminescent device is a back light emitting structure, It can be formed thick enough.

According to another embodiment of the present invention, the hole injection layer, the hole buffer layer, the hole transport layer, the electron inhibition layer, the hole blocking layer, the electron transport layer, the electron injection layer, and the hole injection layer may be interposed between the light emitting layer and the anode or the cathode, And one or more organic layers such as the same layer may be further included.

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

The compound according to the present invention may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

The method for preparing the compound of Formula 1 and the preparation of the organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention and the scope of the present invention is not limited thereto.

<Production Example>

The method for producing the substance of the present invention starts with the synthesis of an intermediate by introducing halide using substituted or unsubstituted aniline as described below. The aryl group is introduced into the halide through the Suzuki reaction and the amino group (-NH ₂ ) is replaced with the bromide (-Br) through the Sandmeyer reaction. Boron can then be introduced eventually using butyllithium and tribromoboranes. Compounds of the specific examples were synthesized through the following reaction using aniline having various substituents in addition to the aniline species shown in Production Example 1-1.

Production Example 1-1: Synthesis of Compound 1-A

[Reaction Scheme 1-1]

The compound 3,5-dimethylaniline (30 g, 0.25 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, bromine (79.2 g, 0.50 mol) was added at 0 ° C, and the mixture was stirred for 2 hours. After the organic layer was extracted with 300 mL of 1 molar solution of sodium cyan sulfate, the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to obtain 65.6 g of the compound 1-A (yield: 95%).

MS [M + H] &lt; ⁺ &gt; = 277

Production Example 1-2: Synthesis of Compound 1-B

[Reaction Scheme 1-2]

The compound 4-tert-butyl-aniline (37.3 g, 0.25 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, and bromine (79.2 g, 0.50 mol) was added at 0 ° C. and stirred for 2 hours. After the organic layer was extracted with 300 mL of 1 molar solution of sodium cyan sulfate, the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to prepare Compound 1-B (70.6 g, yield: 92%).

MS [M + H] &lt; ⁺ &gt; = 305

Production Example 1-3: Synthesis of Compound 1-C

[Reaction 1 - 3]

The compound aniline (23.3 g, 0.25 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, bromine (79.2 g, 0.50 mol) was added at 0 ° C. and the mixture was stirred for 2 hours. After the organic layer was extracted with 300 mL of 1 molar solution of sodium cyan sulfate, the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to prepare the compound 1-C (59.6 g, yield: 95%).

MS [M + H] &lt; ⁺ &gt; = 249

Production Example 1-4: Synthesis of Compound 1-D

[Reaction Scheme 1-4]

The compound 4-chloroaniline (31.9 g, 0.25 mol) was completely dissolved in 300 mL of chloroform in a nitrogen atmosphere, bromine (79.2 g, 0.50 mol) was added at 0 deg. C, and the mixture was stirred for 2 hours. After the organic layer was extracted with 300 mL of 1 molar solution of sodium cyan sulfate, the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to obtain 67 g (yield: 94%) of the compound 1-D.

MS [M + H] &lt; ⁺ &gt; = 283

Production Example 2-1: Synthesis of Compound 2-A

[Reaction Scheme 2-1]

The compound 1-A (61.4 g, 0.22 mol) was completely dissolved in 440 mL of THF (THF) in a nitrogen atmosphere, and 130 mL of an aqueous potassium carbonate solution (10 M) was added. 75.7 g (0.44 mol) of 1-naphthylboronic acid ) Is added. Tetrakis triphenylphosphine palladium (2.5 g, 2.2 mmol) was added and refluxed and stirred for 3 h. After the reaction was completed, the water layer was removed, and the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to obtain Compound 2-A (74 g, yield: 90%).

MS [M + H] &lt; ⁺ &gt; = 374

Production Example 2-2: Synthesis of Compound 2-B

[Reaction Scheme 2-2]

The compound 1-B (67.5 g, 0.22 mol) was completely dissolved in 440 mL of thiethiophene in a nitrogen atmosphere, 130 mL of an aqueous potassium carbonate solution (10 M) was added, and 1-naphthylboronic acid seed (75.7 g, 0.44 mol) do. Tetrakis triphenylphosphine palladium (2.5 g, 2.2 mmol) was added and refluxed and stirred for 3 h. After the completion of the reaction, the water layer was removed, and the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to obtain Compound 2-B (77.7 g, yield: 88%).

MS [M + H] &lt; ⁺ &gt; = 402

Production Example 2-3: Synthesis of Compound 2-C

[Reaction Scheme 2-3]

The compound 1-C (55.2 g, 0.22 mol) was completely dissolved in 440 mL of thiethiophene in a nitrogen atmosphere, 130 mL of an aqueous potassium carbonate solution (10M) was added, 108.3 g of a fluoranthene-3-ylboronic acid solution ) Is added. Tetrakis triphenylphosphine palladium (2.5 g, 2.2 mmol) was added and refluxed and stirred for 3 h. After the reaction was completed, the water layer was removed, and the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to obtain the compound 2-C (92.3 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 494

Production Example 2-4: Synthesis of Compound 2-D

[Reaction Scheme 2-4]

The compound 1-D (62.7 g, 0.22 mol) was completely dissolved in 440 mL of thiethiophene in a nitrogen atmosphere, 130 mL of an aqueous potassium carbonate solution (10 M) was added, and 1-naphthylboronic acid seed (75.7 g, 0.44 mol) do. Tetrakis triphenylphosphine palladium (2.5 g, 2.2 mmol) was added and refluxed and stirred for 3 h. After the reaction was completed, the water layer was removed, and the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to obtain the compound 2-D (72.7 g, yield: 87%).

MS [M + H] &lt; ⁺ &gt; = 380

Production Example 3-1: Synthesis of Compound 3-A

[Reaction Scheme 3-1]

1.8 L of acetonitrile is added to the above compound 2-A (67.2 g, 0.18 mol) in a nitrogen atmosphere, and 45 mL of 12M hydrochloric acid is added at 0 deg. Sodium nitrite (18.6 g, 0.27 mol) is added at 0, stirred for 10 minutes, and cupperbromide (II) (60.3 g, 0.27 mol) is added and heated to 50 ° C. After heating for 1 hour, the precipitate is precipitated in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to obtain Compound 3-A (59 g, yield: 75%).

MS [M + H] &lt; ⁺ &gt; = 437

Production example 3-2: Synthesis of compound 3-B

[Reaction Scheme 3-2]

1.8 L of acetonitrile is added to the above compound 2-B (72.3 g, 0.18 mol) in a nitrogen atmosphere, and 45 mL of 12M hydrochloric acid is added at 0 deg. Sodium nitrite (18.6 g, 0.27 mol) is added at 0, stirred for 10 minutes, and cupperbromide (II) (60.3 g, 0.27 mol) is added and heated to 50 ° C. After heating for 1 hour, the precipitate is precipitated in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to obtain the above compound 3-B (64.5 g, yield: 77%).

MS [M + H] &lt; ⁺ &gt; = 465

Production Example 3-3: Synthesis of Compound 3-C

[Reaction Scheme 3-3]

To a solution of the compound 2-C (88.8 g, 0.18 mol) in a nitrogen atmosphere, 1.8 L of acetonitrile was added and 45 mL of 12 M hydrochloric acid was added at 0 deg. Sodium nitrite (18.6 g, 0.27 mol) is added at 0, stirred for 10 minutes, and cupperbromide (II) (60.3 g, 0.27 mol) is added and heated to 50 ° C. After heating for 1 hour, the precipitate is precipitated in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to obtain the above compound 3-C (76.3 g, yield: 76%).

MS [M + H] &lt; ⁺ &gt; = 557

Production Example 3-4: Synthesis of Compound 3-D

[Reaction Scheme 3-4]

1.8 L of acetonitrile is added to the above compound 2-D (68.4 g, 0.18 mol) in a nitrogen atmosphere, and 45 mL of 12M hydrochloric acid is added at 0 deg. Sodium nitrite (18.6 g, 0.27 mol) is added at 0, stirred for 10 minutes, and cupperbromide (II) (60.3 g, 0.27 mol) is added and heated to 50 ° C. After heating for 1 hour, the precipitate is precipitated in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to give the above compound 3-D (59.9 g, yield: 75%).

MS [M + H] &lt; ⁺ &gt; = 443

Production Example 4-1: Synthesis of Compound 3

[Reaction Scheme 4-1]

200 ml of toluene was added to the compound 3-A (21.8 g, 0.05 mol) in a nitrogen atmosphere, and 20 ml of 2.5 M n-butyllithium was added at -78 deg. After stirring at -78 ° C for 2 hours, tribromoborane (25g, 0.1mol) was added at -78 ° C and stirred for 30 minutes. The temperature is raised to room temperature and stirred for 30 minutes and then stirred at 50 ° C for one hour. After cooling to 0 ° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed (refluxed) for 20 hours. Diisopropylethylamine (6.5 g, 0.05 ml) was further added at room temperature, and then the solvent was completely distilled and purified by column chromatography (chloroform / hexane) to obtain Compound 3 (11.5 g, yield: 63%) .

MS [M + H] &lt; ⁺ &gt; = 367

Production Example 4-2: Synthesis of Compound 2

[Reaction Scheme 4-2]

200 ml of toluene was added to the above compound 3-B (23.3 g, 0.05 mol) in a nitrogen atmosphere, and 20 ml of 2.5 M n-butyllithium was added at -78 deg. After stirring at -78 ° C for 2 hours, tribromoborane (25g, 0.1mol) was added at -78 ° C and stirred for 30 minutes. The temperature is raised to room temperature and stirred for 30 minutes and then stirred at 50 ° C for one hour. After cooling to 0 ° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. Diisopropylethylamine (6.5 g, 0.05 ml) was further added at room temperature, and then the solvent was completely distilled and purified by column chromatography (chloroform / hexane) to obtain Compound 2 (12.8 g, yield 65%) .

MS [M + H] &lt; ⁺ &gt; = 395

Production example 4-3: Synthesis of compound 214

[Reaction Scheme 4-3]

To a solution of the above compound 3-C (27.8 g, 0.05 mol) in a nitrogen atmosphere, 200 ml of toluene was added, and 20 ml of 2.5 M n-butyllithium was added at -78 deg. After stirring at -78 ° C for 2 hours, tribromoborane (25g, 0.1mol) was added at -78 ° C and stirred for 30 minutes. The temperature is raised to room temperature and stirred for 30 minutes and then stirred at 50 ° C for one hour. After cooling to 0 ° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After further addition of diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform / hexane) to obtain the compound 214 (15.1 g, yield: 62%) .

MS [M + H] &lt; ⁺ &gt; = 487

Production Example 4-4: Synthesis of Compound 4-D

[Reaction Scheme 4-4]

200 ml of toluene was added to the compound 3-D (22.2 g, 0.05 mol) in a nitrogen atmosphere, and 20 ml of 2.5 M n-butyllithium was added at -78 deg. After stirring at -78 ° C for 2 hours, tribromoborane (25g, 0.1mol) was added at -78 ° C and stirred for 30 minutes. The temperature is raised to room temperature and stirred for 30 minutes and then stirred at 50 ° C for one hour. After cooling to 0 ° C., diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. Diisopropylethylamine (6.5 g, 0.05 ml) was further added at room temperature, and the solvent was completely distilled and purified by column chromatography (chloroform / hexane) to obtain 18.6 g (yield: 66% ).

MS [M + H] &lt; ⁺ &gt; = 373

Production Example 5-1: Synthesis of Compound 191

[Reaction Scheme 5-1]

30 ml of toluene was added to the compound 4-D (3.7 g, 0.01 mol) in a nitrogen atmosphere, and diphenylamine (1.7 g, 0.01 mol) and sodium tertbutoxide (1.9 g, 0.02 mol) were added. Tetrakis triphenylphosphine palladium (58 mg, 0.05 mmol) was added and the mixture was refluxed for 2 hours and stirred. The organic layer was extracted with water, and the solvent was completely distilled and purified by column chromatography (chloroform / hexane) to obtain the above compound 191 (4.7 g, yield: 93%).

MS [M + H] &lt; ⁺ &gt; = 506

Production Example 5-2: Synthesis of Compound 5-D

[Reaction Scheme 5-2]

140 ml of 1,4-dioxane was added to the compound 4-D (14.9 g, 0.04 mol) in a nitrogen atmosphere, and potassium acetate (7.9 g, 0.08 mol) and bis-pinacolactodiboron (10.2 g, 0.04 mol) . Additional palladium acetate (90 mg, 0.4 mmol) is added and refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with water, and the solvent was completely distilled and purified by column chromatography (chloroform / hexane) to prepare the compound 5-D (17.3 g, yield: 93%).

MS [M + H] &lt; ⁺ &gt; = 465

Production Example 5-3: Synthesis of Compound 31

[Reaction Scheme 5-3]

The compound 5-D (13.9 g, 0.03 mol) was completely dissolved in 30 mL of thiethiophene in a nitrogen atmosphere, 10 mL of an aqueous potassium carbonate solution (10 M) was added, and bromobenzene (4.8 g, 0.03 mol) was added. Tetrakis triphenylphosphine palladium (0.35 g, 0.3 mmol) was added and refluxed and stirred for 3 hours. After the reaction was completed, the water layer was removed, and the organic layer was completely distilled and purified by column chromatography (chloroform / hexane) to obtain the compound 31 (11.8 g, yield: 95%).

MS [M + H] &lt; ⁺ &gt; = 415

<Examples>

In this embodiment, a host material (m-CBP) having a triplet value of 2.5 eV or more, ΔE _ST (difference between singlet energy and triplet energy) of less than 0.2 eV An organic photoluminescence device was fabricated by incorporating a sensitizer (4CzIPN) with TADF (Delayed Fluorescence) characteristics into the luminescent layer, and the characteristics were evaluated.

(Experimental Example 1)

In this example, an organic electroluminescence device having a light emitting layer composed of GD1, m-CBP, and 4CzIPN was prepared and evaluated for its characteristics. 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. Each thin film was laminated on the prepared ITO transparent electrode by a vacuum deposition method with a degree of vacuum of 5.0 Х 10 ^{- 4} ㎫. First, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on ITO to a thickness of 500 Å to form a hole injection layer.

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.

([1,1'-biphenyl] -4-yl) -N- (4- (11 - ([1,1'-biphenyl] -4-yl ) -11H-benzo [a] carbazole-5-yl) phenyl) - [1,1'-biphenyl] -4-amine (EB1) (100 Å) was vacuum deposited to form an electron inhibition layer.

Subsequently, m-CBP, 4CzIPN and GD1 shown below were vapor-deposited at a weight ratio of 68: 30: 2 at a thickness of 300 Å on the electron suppressing layer to form a light emitting layer.

Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting 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 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

Experimental Examples 1-1 to 1-48

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of the compound GD1 in Experimental Example 1.

Comparative Experimental Example 1-1

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following GD2 compound was used instead of the compound GD1 in Experimental Example 1. [

Table 1 shows the results of measurement of voltage, efficiency, and emission wavelength when current was applied to the organic light emitting device fabricated according to Experimental Examples 1-1 to 1-48 and Comparative Example 1-1.

division compound
(Electron inhibiting layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Emission wavelength
(nm) Experimental Example 1 Compound GD1 4.86 4.73 524 Experimental Example 1-1 Compound 2 3.90 17.5 517 Experimental Example 1-2 Compound 3 3.91 17.7 514 Experimental Example 1-3 Compound 4 3.95 17.3 517 Experimental Examples 1-4 Compound 5 3.90 17.7 515 Experimental Examples 1-5 Compound 7 3.90 17.3 516 Experimental Example 1-6 Compound 12 3.94 16.9 514 Experimental Example 1-7 Compound 15 3.97 17.2 511 Experimental Examples 1-8 Compound 22 3.98 17.5 514 Experimental Examples 1-9 Compound 31 3.97 17.6 513 Experimental Example 1-10 Compound 32 3.90 16.9 517 Experimental Example 1-11 Compound 34 3.91 17.8 516 Experimental Example 1-12 Compound 43 3.91 17.7 515 Experimental Example 1-13 Compound 44 3.92 17.3 515 Experimental Example 1-14 Compound 45 3.90 17.7 514 Experimental Example 1-15 Compound 55 3.94 16.8 512 Experimental Example 1-16 Compound 57 3.98 17.3 517 Experimental Example 1-17 Compound 69 3.96 17.1 515 Experimental Example 1-18 Compound 73 3.95 17.5 517 Experimental Example 1-19 Compound 87 3.94 17.7 517 Experimental Example 1-20 Compound 139 3.96 17.3 516 Experimental Example 1-21 Compound 156 3.97 17.7 515 Experimental Example 1-22 Compound 191 3.97 17.2 539 Experimental Example 1-23 Compound 192 3.98 17.1 538 Experimental Example 1-24 Compound 193 3.94 17.0 538 Experimental Example 1-25 Compound 194 3.97 17.4 538 Experimental Example 1-26 Compound 195 3.94 17.1 537 Experimental Example 1-27 Compound 197 3.98 17.4 539 Experimental Example 1-28 Compound 201 3.99 17.3 531 Experimental Example 1-29 Compound 202 3.99 17.1 532 Experimental Example 1-30 Compound 204 3.97 17.4 531 Experimental Examples 1-31 Compound 212 3.98 17.3 532 Experimental Example 1-32 Compound 213 3.95 17.5 531 Experimental Example 1-33 Compound 214 3.94 17.4 518 Experimental Example 1-34 Compound 220 3.95 17.5 532 Experimental Example 1-35 Compound 234 3.97 17.3 510 Experimental Example 1-36 Compound 235 3.95 17.1 517 Experimental Example 1-37 Compound 236 3.94 17.1 531 Experimental Examples 1-38 Compound 237 3.94 17.2 532 Experimental Example 1-39 Compound 238 3.91 17.8 543 Experimental Example 1-40 Compound 239 3.91 17.7 541 Experimental Example 1-41 Compound 240 3.94 17.9 533 Experimental Examples 1-42 Compound 241 3.92 17.8 545 Experimental Example 1-43 Compound 242 3.90 17.6 536 Experimental Examples 1-44 Compound 243 3.92 17.9 544 Experimental Example 1-45 Compound 244 3.94 17.3 541 Experimental Example 1-46 Compound 245 3.91 17.2 544 Experimental Examples 1-47 Compound 246 3.93 17.4 539 Experimental Examples 1-48 Compound 247 3.90 17.7 541 Comparative Experimental Example 1-1 Compound GD2 4.41 13.5 501

As shown in Table 1, in all of the devices of Experimental Examples 1-1 to 1-48 using the compound having the structure of Formula 1 as a core, the voltage was lower than that of the device using the compound GD1 in Experimental Example 1, Results were obtained. Comparing with the comparative example 1-1, it was found that the structure of the formula 1 having a substituent group was improved in terms of voltage, efficiency, and emission wavelength.

As shown in Table 1, it was confirmed that the compound of the present invention has excellent light emitting ability and high color purity, so that it is applicable to organic light emitting devices.

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

Claims (4)

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

In Formula 1,
L is a direct bond; A substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group,
R 1 to R 5 are each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; A carboxy group; Ether group; An ester group; Imide; Amide 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 silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or NRR '
Except that R1 to R5 are all hydrogen,
R and R 'are each independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; A nitrile group; A nitro group; A hydroxy group; A carboxy group; Ether group; An ester group; Imide; Amide 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 silyl group; A substituted or unsubstituted boron 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 heteroaryl group,
a to e each independently represents an integer of 0 to 3,
when b to e are 1 or more, adjacent R2 and R3; R3 and R4; And R4 and R5 may be bonded to each other to form a ring,
When b to e are 2 or more, each of R2 to R5 independently represents an adjacent group bonded to each other to form a ring. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In the general formulas (2) and (3)
R1a and R1b are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; Or NRR '
f is from 0 to 5,
g is 0 to 3,
R2 to R5, R, R 'and b to e are the same as defined in formula (1). The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structures:

. 1. An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is provided in any one of claims 1 to 3 &Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;

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