KR20170101577A - Nitrogen-containing compound and organic electronic device using the same - Google Patents

Abstract

The present invention provides a nitrogen-containing compound and an organic light emitting device comprising the same. The nitrogen-containing compound is represented by chemical formula 1. The compound according to at least one embodiment may improve the efficiency, low driving voltage and/or lifetime characteristics in the organic light emitting device.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrogen-containing compound and an organic light-

TECHNICAL FIELD The present invention relates to a nitrogen-containing 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.

International Patent Application Publication No. 2003-012890

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

An embodiment of the present disclosure provides a nitrogen-containing compound represented by the following Formula 1:

[Chemical Formula 1]

In Formula 1,

R1, R2 and R7 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Halogen crabs; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S,

R3 and R4 are combined to form a ring, or R5 and R6 are combined to form a ring, and the group not forming a ring is the same as that of R1, R2 and R7,

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

Ar ₁ to Ar ₃ are the same or different from each other and each independently represents a nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S.

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 a nitrogen-containing compound of Formula 1 do.

The nitrogen-containing 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.

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 nitrogen-containing compound represented by the above-mentioned formula (1).

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

As used herein, the term " substituted or unsubstituted " Cyano; A nitro group; An amine group; Silyl group; Phosphine oxide groups; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; A heterocyclic group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; A heteroarylamine group; And an arylamine group, or a substituted or unsubstituted aryl group to which at least two of the above-exemplified substituents are connected. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In this specification, the amine group is -NH ₂ ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

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

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

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

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

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

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

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

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

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

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

In the present specification, the term " forming a ring by bonding together " means that an adjacent group is bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.

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

In the present specification, examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, and the like, but are not limited thereto.

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

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

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

In one embodiment of the present invention, the formula (1) is represented by the following formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3)

Wherein R1 to R7, L1, and Ar ₁ to Ar ₃ are as defined as in formula I,

R11 to R18 have the same definitions as R1, R2 and R7.

In one embodiment of the present specification, Ar ₁ to Ar ₃ are the same or different from each other, and each independently represents a nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2-C60 heterocyclic group containing at least one of N, O and S.

In one embodiment of the present invention, L1 in Formula 1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted phenothiazine; Substituted or unsubstituted phenoxazine; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted triazine group; Substituted or unsubstituted pyridine; Substituted or unsubstituted pyrimidines; A substituted or unsubstituted quinoline group; Or a substituted or unsubstituted quinazoline group.

In one embodiment of the present invention, L1 in Formula 1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted phenothiazine; Substituted or unsubstituted phenoxazine; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted triazine group, or a substituted or unsubstituted quinazoline group.

In one embodiment of the present invention, L1 in Formula 1 is a direct bond; A phenylene group; Naphthylene group; Phenothiazine; Phenoxazine; Carbazole group; Benzocarbazole group; Benzimidazole group; Thiophene group; Furan group; A dibenzofurane group; A dibenzothiophene group; Triazine; Pyridine; Pyrimidine; A quinoline group; Or a quinazoline group.

In one embodiment of the present invention, L1 in Formula 1 is a direct bond; A phenylene group; Phenothiazine; Phenoxazine; Carbazole group; Benzocarbazole group; Benzimidazole group; A dibenzofurane group; A dibenzothiophene group; A triazine group, or a quinazoline group.

In one embodiment of the present invention, L1 in Formula 1 is a direct bond; A phenylene group; Carbazole group; A dibenzofurane group; A dibenzothiophene group; A triazine group, or a quinazoline group.

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present specification, it is a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted heteroarylene group.

In one embodiment of the present disclosure, L1 is a phenylene group; Biphenyl group; A terphenyl group; A quaterphenyl group; A naphthalene group; Anthracene group; A fluorene group; Phenanthrene; Pyrene; Or a triphenylene group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quaterphenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted pyrene group; Or a substituted or unsubstituted triphenylene group.

In one embodiment of the present disclosure, L1 is a substituted or unsubstituted phenothiazine; Substituted or unsubstituted phenoxazine; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted triazine group; Substituted or unsubstituted pyridine; Substituted or unsubstituted pyrimidines; A substituted or unsubstituted quinoline group; Or a substituted or unsubstituted quinazoline group.

In one embodiment of the present invention, L 1 is a phenothiazine group (phenoxazine, a carbazole group, a benzocarbazole group, a benzimidazole group, a thiophene group, a furan group, a dibenzofurane group, a dibenzothiophene group, A triazine group, a pyridine group, a pyrimidine group, a quinoline group, or a quinazoline group.

In one embodiment of the present invention, Ar ₁ in Formula ₁ is a substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzonaphthofuran group; A substituted or unsubstituted benzonaphthothiophene group; A substituted or unsubstituted phenothiazine; Substituted or unsubstituted phenoxazine; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; Substituted or unsubstituted phenanthrolines; A substituted or unsubstituted benzoimidazole group; A substituted or unsubstituted benzothiazole group; Or a substituted or unsubstituted benzoxazole group.

In one embodiment of the present invention, Ar ₁ in the general formula ( ₁₎ is a phosphine oxide group; A phenyl group; Biphenyl group; A terphenyl group; Naphthyl group; Phenanthrene; Triphenylene group; A fluorene group; Carbazole group; A dibenzofurane group; A dibenzothiophene group; Benzonaphthofuran group; A benzonaphthothiophene group; Phenothiazine; Phenoxazine; A quinazoline group; A pyridine group; A pyrimidine group; Triazine; Phenanthroline; A benzimidazole group; Benzothiazole group; Or a benzoxazole group.

In one embodiment of the present invention, Ar ₁ in the general formula ( ₁₎ is a phenyl group; A phenyl group substituted or unsubstituted with a substituent selected from the group consisting of a cyano group, a silyl group and an alkyl group; A terphenyl group; Naphthyl group; A fluorene group; A carbazolyl group substituted or unsubstituted with an aryl group; A dibenzofurane group; A dibenzothiophene group; A quinazoline group substituted or unsubstituted with an aryl group; Or a triazine group substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, in the formula ₁ -L1-Ar 1 is selected from the following structural formulas.

In one embodiment of the present invention, Ar < _{2 >} And Ar ₃ are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2-C60 heterocyclic group containing at least one of N, O and S.

In one embodiment of the present invention, Ar < _{2 >} And Ar ₃ is the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present invention, Ar < _{2 >} And Ar ₃ is a phenyl group which is the same as or different from each other and is independently substituted or unsubstituted; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted fluorene group.

In one embodiment of the present invention, Ar < _{2 >} And Ar ₃ is a phenyl group which is the same as or different from each other and is each independently substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A phenanthrene group substituted or unsubstituted with an aryl group; A triphenylene group substituted or unsubstituted with an aryl group; Or a fluorene group substituted or unsubstituted with an aryl group.

In one embodiment of the present invention, Ar < _{2 >} And Ar ₃ are the same or different from each other and are each independently a phenyl group; Biphenyl group; A terphenyl group; Naphthyl group; Phenanthrene; Triphenylene group; Or a fluorene group.

In one embodiment of the present disclosure, -N (Ar ₂ Ar ₃ ) in the above formula (1) is selected from the following structural formulas.

In one embodiment of the present disclosure, R 1, R 2 and R 7 are hydrogen, and the group not forming a ring among R 3 and R 4 or R 5 and R 6 is hydrogen.

In one embodiment of the present invention, R11 to R18 are hydrogen.

In one embodiment of the present disclosure, Formula 1 may be selected from the following formulas.

The heterocyclic compound according to one embodiment of the present specification can be produced by a production method described below.

[Reaction Scheme]

The reaction conditions and materials described in the above reaction schemes can be used as those known in the art, and the types or the numbers of the substituents not described in the above reaction formulas can be changed depending on reaction conditions and materials known in the art.

In the above reaction formula, Ar1 may mean a substituent other than the halogen atom of the compound selected from the following compounds.

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 a nitrogen-containing compound of Formula 1 do.

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, And a nitrogen-containing compound of the formula (1).

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

In one embodiment of the present invention, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the nitrogen-containing compound of the above formula (1).

In one embodiment of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes a nitrogen containing 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 electron injects includes the nitrogen-containing compound of the above formula (1).

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

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

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

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

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

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

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

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

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

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

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

In 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 LiO2 / Al, but are not limited thereto.

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

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

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

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

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

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

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

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

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

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

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments. Embodiments of the spring specification are provided to more fully describe the disclosure to those of ordinary skill in the art.

<Production Example 1> Synthesis of compound 1 to compound

                                                   [Compound 1]

If A 1 is used as a starting material and Ar 1 = phenyl is used in the above reaction scheme 1 step 3, the above-mentioned chemical A-1 can be obtained. (10.0 g, 30.58 mmol) and di ([1,1'-biphenyl] -4-yl) amine (10.80 g, 33.64 mmol) were dissolved in 180 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (3.82 g, 39.76 mmol) was added and bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.31 mmol) were added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to give Compound 1 (13.38 g, yield: 71%).

MS [M + H] &lt; ⁺ &gt; = 613

<Preparation Example 2> Synthesis of compound 2 to compound

                                                   [Compound 2]

If A 1 is used as a starting material and Ar 1 = phenyl is used in the above reaction scheme 1 step 3, the above-mentioned chemical A-1 can be obtained. (10.0 g, 30.58 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluorene- -amine (12.14g, 38.53mmol) was completely dissolved in 160ml of xylene, sodium tert- butoxide was added (3.82g, 39.76mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.16g , 0.31 mmol) were added thereto, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to give Compound 2 (12.27 g, yield: 61%).

MS [M + H] &lt; ⁺ &gt; = 653

<Production Example 3> A compound of Compound 3 Synthesis

                                                  [Compound 3]

The above-mentioned chemical A-2 can be obtained by using A as a starting material and Ar1 = biphenyl as a starting material in the above reaction scheme 1 step 3. Compound A-2 (10.0 g, 24.81 mmol) and di ([1,1'-biphenyl] -4-yl) amine (8.76 g, 27.30 mmol) were completely dissolved in 240 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (3.10 g, 32.26 mmol) was added and bis (tri- tert -butylphosphine) palladium (0) (0.13 g, 0.25 mmol) was added and the mixture was heated with stirring for 6 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 220 ml of tetrahydrofuran to obtain Compound 3 (15.92 g, yield: 93%).

MS [M + H] &lt; ⁺ &gt; = 689

<Production Example 4> A compound of the compound 4 synthesized

                                                    [Compound 4]

The above-mentioned chemical A-2 can be obtained by using A as a starting material and Ar1 = biphenyl as a starting material in the above reaction scheme 1 step 3. (10.0 g, 24.81 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene- -amine (8.76g, 27.30mmol) was completely dissolved in 220ml of xylene, sodium tert- butoxide was added (3.10g, 32.26mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.13g , 0.25 mmol), and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (350 ml) to obtain Compound 4 (14.64 g, yield: 81%).

MS [M + H] &lt; ⁺ &gt; = 729

<Production Example 5> A compound of Compound 5 Synthesis

                                                        [Compound 5]

The above-mentioned chemical A-5 can be obtained by using A as a starting material and Ar1 = 2-naphthylphenyl as a starting material in the above reaction scheme 1 step 3. Compound A-5 (10.0 g, 26.53 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene- -amine (10.53g, 34.48mmol) was completely dissolved in 180ml of xylene, sodium tert- butoxide was added (3.31g, 47.71mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.14g , 0.27 mmol), and the mixture was heated with stirring for 2 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to give Compound 5 (12.35 g, yield: 66%).

MS [M + H] &lt; ⁺ &gt; = 703

< Manufacturing Example 6> Synthesis of the following compound 6

                                                        [Compound 6]

The above-mentioned chemical A-5 can be obtained by using A as a starting material and Ar1 = 2-naphthylphenyl as a starting material in the above reaction scheme 1 step 3. Compound A-5 (10.0 g, 26.53 mmol), N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 4', 1 " - terphenyl] -4-amine (11.58g, 29.18mmol) was completely dissolved in the xylene alkylene 260ml was added sodium tert- butoxide (3.31g, 47.71mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 9 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 300 ml of tetrahydrofuran to obtain Compound 6 (17.71 g, yield: 91%).

MS [M + H] &lt; ⁺ &gt; = 703

< Manufacturing Example 7> Synthesis of the following compound 7

                                                    [Compound 7]

The above-mentioned chemical A-7 can be obtained by using A as a starting material and Ar1 = biphenyl as a starting material in the above reaction scheme 1 step 3. Compound A-7 (10.0 g, 24.81 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl- -amine (8.76g, 27.30mmol) was completely dissolved in 220ml of xylene, sodium tert- butoxide was added (2.62g, 27.31mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.11g , 0.21 mmol) were added and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (350 ml) to obtain Compound 7 (14.26 g, yield: 84%).

MS [M + H] &lt; ⁺ &gt; = 805

< Manufacturing Example 8> A compound of the compound 8 synthesized

                                                     [Compound 8]

The above-mentioned chemical A-7 can be obtained by using A as a starting material and Ar1 = biphenyl as a starting material in the above reaction scheme 1 step 3. Compound A-7 (10.0 g, 24.81 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.66 g, 23.11 mmol) were dissolved in 280 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (2.62 g, 27.31 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.11 g, 0.21 mmol) was added and the mixture was stirred for 6 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (350 ml) to obtain Compound 8 (10.08 g, yield: 70%).

MS [M + H] &lt; ⁺ &gt; = 689

< Manufacturing Example 9> A compound of the compound 9 synthesized

                                                        [Compound 9]

The above-mentioned chemical A-9 can be obtained by using A as a starting material and Ar1 = biphenyl as a starting material in the above reaction scheme 1 step 3. Compound A-9 (10.0 g, 22.08 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.95 g, 24.28 mmol) were dissolved in 230 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (2.62 g, 27.31 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.11 g, 0.21 mmol) was added and the mixture was heated with stirring for 8 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (350 ml) to obtain Compound 9 (9.47 g, yield 65%).

MS [M + H] &lt; ⁺ &gt; = 663

<Production Example 10> A compound of the Compound 10 synthesis

                                                  [Compound 10]

If B is used as the starting material and Ar1 = phenyl is used in the above reaction scheme 1 step 3, the above-mentioned compound B-1 can be obtained. Compound (10.0 g, 30.58 mmol) and di ([1,1'-biphenyl] -4-yl) amine (10.80 g, 33.64 mmol) were completely dissolved in 220 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (3.82 g, 39.76 mmol) was added and bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.31 mmol) was added and the mixture was heated with stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (260 ml) to obtain Compound 10 (12.05 g, yield: 63%).

MS [M + H] &lt; ⁺ &gt; = 613

<Production Example 11> A compound of the Compound 11 synthesis

                                                   [Compound 11]

If B is used as the starting material and Ar1 = phenyl is used in the above reaction scheme 1 step 3, the above-mentioned compound B-1 can be obtained. (10.0 g, 30.58 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluorene- -amine (12.14g, 38.53mmol) was completely dissolved in the xylene alkylene 200ml sodium tert- butoxide was added (3.82g, 39.76mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.16g , 0.31 mmol) were added and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (210 ml) to obtain the compound 11 (11.05 g, yield: 55%).

MS [M + H] &lt; ⁺ &gt; = 653

<Production Example 12> A compound of the Compound 12 synthesis

                                                  [Compound 12]

The above-mentioned chemical B-2 can be obtained by using B as a starting material and Ar1 = 4-biphenyl as a starting material in the above reaction scheme 1 step 3. Compound (10.0 g, 24.81 mmol) and di ([1,1'-biphenyl] -4-yl) amine (8.76 g, 27.30 mmol) were dissolved in 280 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (3.10 g, 32.26 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.13 g, 0.25 mmol) was added and the mixture was heated with stirring for 8 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 230 ml of tetrahydrofuran to obtain the compound 12 (14.33 g, yield: 84%).

MS [M + H] &lt; ⁺ &gt; = 689

<Production Example 13> A compound of the Compound 13 synthesis

                                                  [Compound 13]

The above-mentioned chemical B-2 can be obtained by using B as a starting material and Ar1 = 4-biphenyl as a starting material in the above reaction scheme 1 step 3. (10.0 g, 24.81 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene- -amine (8.76g, 27.30mmol) was completely dissolved in 260ml of xylene, sodium tert- butoxide was added (3.10g, 32.26mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.13g , 0.25 mmol), and the mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 360 ml of ethyl acetate to obtain Compound 13 (13.18 g, yield: 72%).

MS [M + H] &lt; ⁺ &gt; = 729

<Production Example 14> A compound of the Compound 14 synthesis

                                                  [Compound 14]

The above compound B-5 can be obtained by using B as a starting material and Ar1 = 2-naphthyl in the above reaction scheme 1 step 3. (10.0 g, 26.53 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluorene- -amine (10.53g, 34.48mmol) was completely dissolved in 220ml of xylene, sodium tert- butoxide was added (3.31g, 47.71mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.14g , 0.27 mmol), and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure, and recrystallized from 210 ml of ethyl acetate to obtain Compound 14 (12.35 g, yield: 66%).

MS [M + H] &lt; ⁺ &gt; = 703

< Manufacturing Example 15> Synthesis of Compound (15)

                                                      [Compound 15]

The above compound B-5 can be obtained by using B as a starting material and Ar1 = 2-naphthyl in the above reaction scheme 1 step 3. (10.0 g, 26.53 mmol) and N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 4', 1 " - terphenyl] -4-amine (11.58g, 29.18mmol) was completely dissolved in the xylene alkylene 300ml was added sodium tert- butoxide (3.31g, 47.71mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.14 g, 0.27 mmol) was added thereto, followed by heating and stirring for 11 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 310 ml of tetrahydrofuran to obtain the compound 15 (15.94 g, yield: 82%).

MS [M + H] &lt; ⁺ &gt; = 703

<Production Example 16> A compound of the Compound 16 synthesis

                                                   [Compound 16]

If B is used as a starting material and Ar1 = terphenyl is used in the above reaction scheme 1 step 3, the above-mentioned compound B-7 can be obtained. (10.0 g, 24.81 mmol) and N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluorene- -amine (8.76g, 27.30mmol) was completely dissolved in 260ml of xylene, sodium tert- butoxide was added (2.62g, 27.31mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.11g , 0.21 mmol), and the mixture was heated with stirring for 6 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 360 ml of ethyl acetate to obtain Compound 16 (12.82 g, yield: 76%).

MS [M + H] &lt; ⁺ &gt; = 805

<Production Example 17> A compound of the Compound 17 synthesis

                                                       [Compound 17]

If B is used as a starting material and Ar1 = terphenyl is used in the above reaction scheme 1 step 3, the above-mentioned compound B-7 can be obtained. (10.0 g, 24.81 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.66 g, 23.11 mmol) were dissolved in 320 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (2.62 g, 27.31 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.11 g, 0.21 mmol) was added and the mixture was heated with stirring for 8 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 360 ml of ethyl acetate to obtain 9.97 g (yield: 62%) of the compound 17.

MS [M + H] &lt; ⁺ &gt; = 689

<Example 18> A compound of the Compound 18 synthesis

                                                       [Compound 18]

The above-mentioned chemical B-9 can be obtained by using B as a starting material and Ar1 = 2-phenyl naphthalene in the above reaction scheme 1 step 3. To a 500 ml round-bottomed flask under a nitrogen atmosphere, compound B-9 (10.0 g, 22.08 mmol) and N-phenyl- [1,1'-biphenyl] -4- amine (5.95 g, 24.28 mmol) After dissolving, sodium tert-butoxide (2.62 g, 27.31 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.11 g, 0.21 mmol) was added and the mixture was heated with stirring for 10 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (370 ml) to give Compound 1 (10.42 g, yield: 72%).

MS [M + H] &lt; ⁺ &gt; = 663

<Production Example 19> A compound of the Compound 19 synthesis

                                                   [Compound 19]

If A 1 is used as a starting material and Ar 1 = phenyl is used in the above reaction scheme 1 step 3, the above-mentioned chemical A-1 can be obtained. (10.0 g, 30.58 mmol) and N - ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -2- ( Tert -butylphosphine) palladium (0) (0.16 g, 33.64 mmol) was dissolved in 180 ml of xylene, followed by the addition of sodium tert-butoxide (3.82 g, 39.76 mmol) 0.31 mmol), and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to obtain Compound 19 (14.72 g, yield: 78%).

MS [M + H] &lt; ⁺ &gt; = 613

<Production Example 20> A compound of the Compound 20 synthesis

                                                [Compound 20]

If B is used as the starting material and Ar1 = phenyl is used in the above reaction scheme 1, step 3, the above-mentioned compound B-1 can be obtained. (10.0 g, 30.58 mmol) and N - ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -2- ( Tert -butylphosphine) palladium (0) (0.16 g, 33.64 mmol) was dissolved in 220 ml of xylene, followed by the addition of sodium tert-butoxide (3.82 g, 39.76 mmol) 0.31 mmol) were added thereto, followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (270 ml) to obtain Compound 20 (14.72 g, yield: 78%).

MS [M + H] &lt; ⁺ &gt; = 613

<Production Example 21> A compound of the Compound 21 synthesis

                                                [Compound 21]

The above-mentioned chemical A-2 can be obtained by using A as a starting material and Ar1 = 4-biphenyl as a starting material in the above reaction scheme 1 step 3. (10.0 g, 24.81 mmol) and N - ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -2- ( Tert -butylphosphine) palladium (0) (0.13 g, 32.26 mmol) was added to the reaction mixture after thoroughly dissolving the amine (8.76 g, 27.30 mmol) in 270 ml of xylene, followed by the addition of sodium tert- 0.25 mmol) was added thereto, followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 230 ml of tetrahydrofuran to obtain the compound 21 (14.33 g, yield: 83%).

MS [M + H] &lt; ⁺ &gt; = 689

<Production Example 22> A compound of the Compound 22 synthesis

                                               [Compound 22]

The above-mentioned chemical B-2 can be obtained by using B as a starting material and Ar1 = 4-biphenyl as a starting material in the above reaction scheme 1 step 3. (10.0 g, 24.81 mmol), N - ([1,1'-biphenyl] -4-yl) - [1,1'- biphenyl] -2- ( Tert -butylphosphine) palladium (0) (0.13 g, 32.26 mmol) was added to the reaction mixture after thoroughly dissolving the amine (8.76 g, 27.30 mmol) in 270 ml of xylene, followed by the addition of sodium tert- 0.25 mmol) were added thereto, followed by heating and stirring for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 230 ml of tetrahydrofuran to obtain the compound 22 (11.51 g, yield: 67%).

MS [M + H] &lt; ⁺ &gt; = 689

<Production Example 23> A compound of the Compound 23 synthesis

                                                [Compound 23]

The above-mentioned chemical A-15 can be obtained by using A as a starting material and Ar1 = 2-fluorene in the above reaction scheme 1 step 3. Compound A-15 (10.0 g, 22.57 mmol) and di ([1,1'-biphenyl] -4-yl) amine (7.97 g, 24.83 mmol) were completely dissolved in 200 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (2.82 g, 29.35 mmol) was added and bis (tri- tert -butylphosphine) palladium (0) (0.12 g, 0.23 mmol) was added and the mixture was heated with stirring for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 220 ml of tetrahydrofuran to obtain Compound 23 (10.78 g, yield: 66%).

MS [M + H] &lt; ⁺ &gt; = 729

<Production Example 24> A compound of the Compound 24 synthesis

                                             [Compound 24]

The above-mentioned chemical A-21 can be obtained by using A as the starting material and Ar1 = 2-9-phenyl-9H-carbazole in the above reaction scheme 1 step 3. Compound A-21 (10.0 g, 20.33 mmol) and 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (6.37 g, 22.36 mmol) were dissolved in 220 ml of xylene in a 500 ml round- To the solution was added sodium tert-butoxide (2.54 g, 26.42 mmol), followed by addition of bis (tri- tert -butylphosphine) palladium (0) (0.10 g, 0.20 mmol) and heating with stirring for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 260 ml of tetrahydrofuran to obtain the above compound 24 (11.59 g, yield: 77%).

MS [M + H] &lt; ⁺ &gt; = 742

<Production Example 25> A compound of the Compound 25 synthesis

                                                [Compound 25]

The above compound B-15 can be obtained by using B as a starting material and Ar 1 = 2-fluorene in the above reaction scheme 1, Step 3. (10.0 g, 22.57 mmol) and di ([1,1'-biphenyl] -4-yl) amine (7.97 g, 24.83 mmol) were dissolved in 220 ml of xylene in a 500 ml round- After dissolving, sodium tert-butoxide (2.82 g, 29.35 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.12 g, 0.23 mmol) was added and the mixture was heated with stirring for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 200 ml of tetrahydrofuran to obtain the compound 25 (8.66 g, yield: 55%).

MS [M + H] &lt; ⁺ &gt; = 729

<Production Example 26> A compound of the Compound 26 synthesis

                                            [Compound 26]

The above compound B-21 can be obtained by using A as the starting material and Ar1 = 2-9-phenyl-9H-carbazole in the above reaction scheme 1 step 3. Compound (B-21) (10.0 g, 20.33 mmol) and 9,9-dimethyl-N-phenyl-9H- fluoren- 2 -amine (6.37 g, 22.36 mmol) were dissolved in 220 ml of xylene in a 500 ml round- After dissolving completely, sodium tert-butoxide (2.54 g, 26.42 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.10 g, 0.20 mmol) was added and the mixture was heated with stirring for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 235 ml of tetrahydrofuran to obtain Compound 26 (10.44 g, yield 69%).

MS [M + H] &lt; ⁺ &gt; = 742

< Experimental Example  1-1>

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. At this time, a Fischer Co. product was used as a detergent, and distilled water filtered by a filter (filtration) manufactured by 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 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM to form an electron blocking layer.

[Compound 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 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

<Experimental Example 1-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2 was used instead of Compound 1 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 3 was used instead of Compound 1 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 4 was used instead of Compound 1 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 6 was used instead of Compound 1 in Experimental Example 1.

<Experimental Example 1-6>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 8 was used instead of Compound 1 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 9 was used instead of Compound 1 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 10 was used instead of Compound 1 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 12 was used instead of Compound 1 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 15 was used instead of Compound 1 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 17 was used instead of Compound 1 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 22 was used instead of Compound 1 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 23 was used instead of Compound 1 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 24 was used instead of Compound 1 in Experimental Example 1.

&Lt; Comparative Example 1 &

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

[EB1]

&Lt; Comparative Example 2 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following compound EB2 was used in place of Compound 1 in Experimental Example 1.

[EB2]

&Lt; Comparative Example 3 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following compound EB3 was used in place of Compound 1 in Experimental Example 1.

[EB3]

&Lt; Comparative Example 4 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the following compound (EB4) was used in place of Compound (1).

[EB4]

When an electric current was applied to the organic light-emitting devices fabricated by Examples 1-1 to 14 and Comparative Examples 1 to 4, the results shown in Table 1 were obtained.

compound
(Electronic blocking layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1-1 Compound 1 3.68 6.64 (0.138, 0.127) Experimental Example 1-2 Compound 2 3.73 6.56 (0.139, 0.125) Experimental Example 1-3 Compound 3 3.64 6.65 (0.138, 0.126) Experimental Examples 1-4 Compound 4 3.75 6.52 (0.138, 0.127) Experimental Examples 1-5 Compound 6 3.72 6.51 (0.137, 0.125) Experimental Example 1-6 Compound 8 3.61 6.68 (0.136, 0.125) Experimental Example 1-7 Compound 9 3.59 6.90 (0.136, 0.127) Experimental Examples 1-8 Compound 10 3.66 6.66 (0.136, 0.125) Experimental Examples 1-9 Compound 12 3.65 6.63 (0.137, 0.125) Experimental Example 1-10 Compound 15 3.64 6.62 (0.138, 0.125) Experimental Example 1-11 Compound 17 3.65 6.64 (0.136, 0.125) Experimental Example 1-12 Compound 22 3.50 6.71 (0.137, 0.125) Experimental Example 1-13 Compound 23 3.68 6.68 (0.136, 0.125) Experimental Example 1-14 Compound 24 3.69 6.65 (0.138, 0.126) Comparative Example 1 EB1 4.08 5.91 (0.136, 0.127) Comparative Example 2 EB2 4.12 6.07 (0.136, 0.127) Comparative Example 3 EB3 4.04 5.94 (0.135, 0.125) Comparative Example 4 EB4 4.36 5.59 (0.136, 0.126)

As shown in Table 1, the organic luminescent device manufactured using the compound of the present invention as an electron blocking layer has a comparative example 1 in which substituents are connected to other positions of the core of the present invention and a comparative example in which a phenyl group and a biphenyl group are substituted with a linker Compared with the case of using the materials of Examples 2 and 3, the compound of the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of an organic light emitting device because it has an electron blocking function.

In Experimental Examples 1-1 to 1-14, the voltage was reduced by 10% to 12% and the efficiency was more than 10% 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  2-1 to 2-14>

The same experiment was conducted except that the EB5 material was used as the electron blocking layer in Experimental Example 1 and the compounds of Experimental Examples 1-1 to 1-14 were used instead of NPB as the hole transporting layer.

[EB5]

&Lt; Comparative Example 5 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 2, except that Compound HT1 was used instead of Compound 1 in Experimental Example 2-1.

[HT1]

&Lt; Comparative Example 6 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 2, except that Compound HT2 was used instead of Compound 1 in Experimental Example 2-1.

[HT2]

When current was applied to the organic light-emitting device manufactured in Experimental Example 2, Experimental Examples 2-1 to 14 and Comparative Examples 5 and 6, 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 2-1 Compound 1 4.45 5.45 (0.138, 0.127) EXPERIMENTAL EXAMPLE 2-2 Compound 2 4.52 5.35 (0.139, 0.122) Experimental Example 2-3 Compound 3 4.48 5.36 (0.138, 0.126) Experimental Example 2-4 Compound 4 4.43 5.52 (0.138, 0.127) Experimental Example 2-5 Compound 6 4.57 5.58 (0.137, 0.125) Experimental Examples 2-6 Compound 8 4.56 5.55 (0.136, 0.125) Experimental Example 2-7 Compound 9 4.44 5.51 (0.136, 0.127) Experimental Examples 2-8 Compound 10 4.41 5.59 (0.136, 0.125) Experimental Examples 2-9 Compound 12 4.58 5.46 (0.137, 0.125) Experimental Example 2-10 Compound 15 4.49 5.45 (0.138, 0.125) Experimental Example 2-11 Compound 17 4.57 5.46 (0.136, 0.125) Experimental Examples 2-12 Compound 22 4.52 5.44 (0.137, 0.125) Experimental Example 2-13 Compound 23 4.43 5.40 (0.136, 0.125) Experimental Example 2-14 Compound 24 4.50 5.50 (0.138, 0.126) Comparative Example 5 HT1 5.06 4.91 (0.136, 0.127) Comparative Example 6 HT2 5.18 4.52 (0.135, 0.125)

As shown in Table 2, Comparative Example 4 in which a phenyl group and a biphenyl group were substituted with a comparative linker in which a substituent was connected to another position of the core of the present invention of an organic light emitting device manufactured using the compound of the present invention as a hole transport layer, 5, the compound of the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of an organic light emitting device because it plays a role of transporting holes.

Specifically, in Experimental Examples 2-1 to 2-14, the voltage is reduced by 10% or more and the efficiency is also 7 to 10% or more higher than that of the comparative example.

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.

Although the preferred embodiments (electron blocking layer, hole transporting layer) of the present invention have been described above, the present invention is not limited thereto and can be variously modified 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:
8: Electron transport layer

Claims (15)

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

In Formula 1,
R1, R2 and R7 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Halogen crabs; A nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R3 and R4 are combined to form a ring, or R5 and R6 are combined to form a ring, and the group not forming a ring is the same as that of R1, R2 and R7,
L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar ₁ to Ar ₃ are the same or different from each other and each independently represents a nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The nitrogen-containing compound according to claim 1, wherein the formula (1) is represented by the following formula (2) or (3):
(2)

(3)

In the general formulas (2) and (3)
Wherein R1 to R7, L1, and Ar ₁ to Ar ₃ are as defined as in formula I,
R11 to R18 have the same definitions as R1, R2 and R7. A nitrogen-containing compound according to claim _1, -L1-Ar 1 in formula (I) is selected from the group consisting of the following structural formula:

The nitrogen-containing compound according to claim 1, wherein -N (Ar ₂ Ar ₃ ) in the general formula (1) is selected from the following structural formulas:

2. The nitrogen-containing compound according to claim 1, wherein L1 is a direct bond. 2. The nitrogen-containing compound according to claim 1, wherein L1 is a substituted or unsubstituted arylene group. [3] The compound according to claim 1, wherein L1 is a phenylene group; Biphenyl group; A terphenyl group; A quaterphenyl group; A naphthalene group; Anthracene group; A fluorene group; Phenanthrene; Pyrene; Or a triphenylene group. 2. The nitrogen-containing compound according to claim 1, wherein L1 is a heteroarylene group. [3] The compound according to claim 1, wherein L1 is phenothiazine; Phenoxazine; Carbazole group; Benzocarbazole group; Benzimidazole group; Thiophene group; Furan group; A dibenzofurane group; A dibenzothiophene group; Triazine; A pyridine group; A pyrimidine group; A quinoline group; Or a quinazoline group. 2. The compound according to claim 1, wherein R1, R2 and R7 are hydrogen,
And R &lt; 3 &gt; and R &lt; 4 &gt; or R &lt; 5 &gt; and R &lt; 6 &gt; are hydrogen. The nitrogen-containing compound according to claim 1, wherein the formula (1) is selected from the following formulas:

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 nitrogen-containing compound according to any one of claims 1 to 11. [Claim 12] The organic light emitting device according to claim 12, wherein the organic material layer including the nitrogen-containing compound is a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting holes and transporting holes. 14. The organic light emitting device according to claim 12, wherein the organic compound layer containing the nitrogen-containing compound is a light emitting layer. 14. The organic light emitting device according to claim 12, wherein the organic material layer containing the nitrogen-containing compound is an electron blocking layer.

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