[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

KR20150136033A - Nitrogen-containing heterocyclic compounds and organic electronic device using the same - Google Patents

Nitrogen-containing heterocyclic compounds and organic electronic device using the same Download PDF

Info

Publication number
KR20150136033A
KR20150136033A KR1020150073254A KR20150073254A KR20150136033A KR 20150136033 A KR20150136033 A KR 20150136033A KR 1020150073254 A KR1020150073254 A KR 1020150073254A KR 20150073254 A KR20150073254 A KR 20150073254A KR 20150136033 A KR20150136033 A KR 20150136033A
Authority
KR
South Korea
Prior art keywords
group
substituted
unsubstituted
organic
layer
Prior art date
Application number
KR1020150073254A
Other languages
Korean (ko)
Other versions
KR101777454B1 (en
Inventor
이동훈
홍성길
차용범
강민영
천민승
김동식
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Publication of KR20150136033A publication Critical patent/KR20150136033A/en
Application granted granted Critical
Publication of KR101777454B1 publication Critical patent/KR101777454B1/en

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • C07D263/64Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/60Naphthoxazoles; Hydrogenated naphthoxazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L51/50
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1018Heterocyclic compounds
    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention relates to a nitrogen-containing heterocyclic compound which can highly improve efficiency, driving voltage and lifespan of an organic electronic device and an organic electronic device using the same and, more specifically, to a nitrogen-containing heterocyclic compound represented by chemical formula 1. In addition, the present invention provides an organic electronic device, comprising: a first electrode; a second electrode; and one or more organic layers arranged between the first electrode and the second electrode, wherein the one or more layers in the organic layers comprise the nitrogen-containing heterocyclic compound represented by the chemical formula 1.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrogen-containing heterocyclic compound and an organic electronic device using the same. BACKGROUND ART < RTI ID = 0.0 >

This specification claims the benefit of Korean Patent Application No. 10- 2014-0063299 filed on May 26, 2014, the entire contents of which are incorporated herein by reference.

The present specification relates to nitrogen-containing heterocyclic compounds and organic electronic devices using the same.

An organic electronic device means an element requiring charge exchange between an electrode and an organic material using holes and / or electrons. The organic electronic device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electric device. The second type is an electronic device that injects holes and / or electrons into an organic semiconductor that interfaces with an electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like. These devices may be used as a hole injecting or transporting material, an electron injecting or transporting material, need. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials act on a similar principle.

Generally, an organic light emitting phenomenon is 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. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

International Patent Application Publication No. 2003-012890

It is an object of the present invention to provide a nitrogen-containing heterocyclic compound having an effect of increasing the efficiency of a device, lowering a driving voltage and increasing stability, and an organic electronic device using the same.

The present invention provides a nitrogen-containing heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

Figure pat00001

In formula (1)

X is O or S,

R 1 is - (L 1) p 1 - (Y 1) , and q 1, R 2 is - (L 2) p 2 - (Y 2) and q 2, R 3 is - (L 3) p 3 - ( Y 3 ) q 3 , R 4 is - (L 4 ) p 4 - (Y 4 ) q 4 and R 5 is - (L 5 ) p 5 - (Y 5 ) q 5 ,

p 1 to p 5 each represent an integer of 0 to 10,

q 1 to q 5 each represent an integer of 1 to 10,

If more than p x is 2, L x is the same or different from each other,

When q x is 2 or more, Y x are the same or different from each other,

x is an integer of 1 to 5,

At least two adjacent substituents out of R 2 to R 5 form a monocyclic or polycyclic aliphatic, aromatic, aliphatic hetero or aromatic hetero condensation ring,

Said fused ring being selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group,

L 1 to L 5 are the same or different and are each independently a direct bond; Oxygen; sulfur; Substituted or unsubstituted nitrogen; Substituted or unsubstituted phosphorus; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; Or a substituted or unsubstituted heterocyclic group,

Y 1 to Y 5 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A 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 alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or forms a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group or forms a spiro bond.

The present invention also relates to an organic electronic 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 has a structure represented by the formula And a nitrogen heterocyclic compound.

The novel compound according to the present invention can be used as a material for an organic material layer of an organic electronic device including an organic light emitting device, and an organic electronic device including the organic light emitting device exhibits excellent characteristics in terms of efficiency, driving voltage, and lifetime. In particular, the novel compounds according to the present invention have excellent thermal stability, have a deep HOMO level, a high triplet state and a hole stability, thus exhibiting excellent properties. It can be used purely in an organic electronic device including an organic light emitting device, mixed with an impurity, improved in light efficiency, and improved in device lifetime characteristics by thermal stability of the compound.

1 to 5 are cross-sectional views illustrating the structure of an organic electronic device according to one embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

The present invention provides a nitrogen-containing heterocyclic compound represented by the above formula (1).

In the above formula (1), adjacent substituents of R 2 to R 5 form a monocyclic or polycyclic aliphatic, aromatic, aliphatic hetero or aromatic hetero condensation ring.

In one embodiment of the present specification, R 2 and R 3 form a condensed ring of mono- or polycyclic aliphatic, aromatic, aliphatic hetero or aromatic hetero, with each other.

In another embodiment, R 2 and R 3 form an aromatic condensed ring with each other.

In another embodiment, R 2 and R 3 together form a benzene ring.

In one embodiment of the present disclosure, R 3 and R 4 form a condensed ring of a mono- or polycyclic aliphatic, aromatic, aliphatic hetero or aromatic hetero with each other.

In another embodiment, R < 3 > and R < 4 > form an aromatic condensed ring with each other.

In another embodiment, R 3 and R 4 together form a benzene ring.

In one embodiment of the present disclosure, R 4 and R 5 form a condensed ring of mono- or polycyclic aliphatic, aromatic, aliphatic, or aromatic heteroatoms with each other.

In another embodiment, R 4 and R 5 form an aromatic condensed ring with each other.

In another embodiment, R < 4 > and R < 5 > form a benzene ring with each other.

In one embodiment of the present invention, the compound represented by the formula (1) is any one of the following formulas (2) to (4).

(2)

Figure pat00002

(3)

Figure pat00003

[Chemical Formula 4]

Figure pat00004

In formulas (2) to (4)

X, R 1 to R 5 are the same as defined in formula (1)

m, n and o are each an integer of 0 to 4,

R 6 to R 8 are the same as or different from each other and are the same as defined for R 1 to R 5 , respectively.

In an embodiment of the present specification, when p x is 2 or more, L x are the same as or different from each other, and when q x is 2 or more, Y x are the same as or different from each other, and x is an integer of 1 to 5 .

In one embodiment of the present disclosure, when the p x is 0, wherein Y x is deuterium; A nitrile group; A halogen group; A substituted or unsubstituted boron group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, when p x is 1 or more, L x is a substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heterocyclic group, and Y x is a substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, L x is a substituted or unsubstituted arylene group or a substituted or unsubstituted divalent heterocyclic group, Y x is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic ring P x + q x is 2 or more.

In one embodiment of the present disclosure, at least one of Y 1 to Y 5 is deuterium; A nitrile group; A halogen group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

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

In the present specification, the term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, When substituted, two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; Carbazole group; An arylamine group; An aryl group; A fluorenyl group; A nitrile group; A nitro group; A hydroxy group; A cyano group and a heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 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. 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 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 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the aryl group may be monocyclic to an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60 carbon atoms. Specific examples of the aryl group include monocyclic aromatic and naphthyl groups such as phenyl, biphenyl and terphenyl groups, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, tetracenyl, Acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group, acenaphthacenyl group,

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

When the fluorenyl group is substituted,

Figure pat00005
,
Figure pat00006
,
Figure pat00007
And
Figure pat00008
And the like. However, the present invention is 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, But are not limited thereto.

In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms of the heterocyclic group 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.

The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring.

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

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 50. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monocyclic arylamine group, a substituted or unsubstituted monocyclic arylamine group substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted monocyclic arylamine group, Substituted or unsubstituted monocyclic triarylamine groups, unsubstituted monocyclic triarylamine groups, substituted or unsubstituted polycyclic diarylamine groups, substituted or unsubstituted polycyclic triarylamine groups, substituted or unsubstituted monocyclic and polycyclic diarylamines Or a substituted or unsubstituted mono- and polycyclic triarylamine group. Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group and the aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, Naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Phenanthryloxy, 9-phenanthryloxy and the like. Examples of the arylthioxy group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenyl And the like. Examples of the aryl sulfoxy group include a benzene sulfoxy group and a p-toluenesulfoxy group, but the present invention is not limited thereto.

In the present specification, the alkylthio group and the alkyl group in the alkylsulfoxy group are the same as the alkyl groups described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In the present specification, the aralkylamine group of the aralkylamine group specifically includes an aryl moiety having 6 to 49 carbon atoms and an alkyl moiety having 1 to 44 carbon atoms. Specific examples thereof include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, Group, an?,? -Methylphenylbenzyl group, a 1-naphthylbenzyl group, a 2-naphthylbenzyl group, a p-fluorobenzyl group, a 3,5-difluorobenzyl group, , p-methoxybenzyl group, m-methoxybenzyl group,? -phenoxybenzyl group,?,? -benzyloxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, A nitrobenzyl group, a cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group and the like, but are not limited thereto.

In the present specification, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

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

In the present specification, the adjacent groups are bonded to form a ring, meaning that an alkylene or hydrocarbon unsubstituted or substituted with a hydrocarbon or a heterocyclic ring, or an alkenylene substituted or not substituted with a heterocyclic ring is bonded to each other to form a ring can do.

In the present specification, the hydrocarbon ring may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and examples of the cycloalkyl group or the aryl group may be selected, except that the hydrocarbon ring is not a monovalent group. The heterocyclic ring may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and examples thereof may be selected from the heterocyclic groups except that the heterocyclic group is not a monovalent group.

In the present specification, the unsubstituted nitrogen means that it has no substituent other than hydrogen bonded to nitrogen.

In the present specification, unsubstituted phosphorus means that it has no substituent other than hydrogen bonded to phosphorus.

In one embodiment of the present disclosure, X is O.

In another embodiment of the present disclosure, X is S.

In one embodiment of the present disclosure, p x is zero.

In one embodiment of the present disclosure, p x is one.

In one embodiment of the present disclosure, p x is 2.

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

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

In one embodiment of the present specification, L x is a phenylene group. The phenylene group

Figure pat00009
or
Figure pat00010
to be.

In one embodiment of the present specification, L x is a phenylene group substituted with a carbazole group.

In one embodiment of the present invention, L x is a biphenylene group.

In one embodiment of the present specification, L x is a biphenylene group substituted with a carbazole group.

In one embodiment of the present invention, L x is a biphenylene group. The biphenylene group

Figure pat00011
or
Figure pat00012
to be.

In one embodiment of the present specification, L x is a naphthylene group.

In one embodiment of the present specification, L x is a naphthylene group. The naphthylene group

Figure pat00013
or
Figure pat00014
to be.

In one embodiment of the present specification, L x is an anthracenylene group.

In one embodiment of the present specification, L x is a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present specification, L x is a pyridylene group.

In one embodiment of the present specification, L is substituted or unsubstituted nitrogen.

In one embodiment of the present specification, L x is substituted or unsubstituted nitrogen.

In one embodiment of the present specification, L x is nitrogen substituted with an aryl group.

In one embodiment of the present specification, L x is nitrogen substituted with a phenyl group.

In one embodiment of the present disclosure, q x is 1.

In one embodiment of the present disclosure, q x is 2.

In one embodiment of the present specification, Y x is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Y x is an aryl group substituted or unsubstituted with a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Y x is an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a substituted or unsubstituted heterocyclic group containing at least one N atom having 2 to 30 carbon atoms.

In one embodiment of the present specification, Y x is an aryl group or a substituted or unsubstituted aryl group selected from the group consisting of an aryl group and a heterocyclic group.

As used herein, the aryl group is phenyl; Biphenyl; Terphenyl; Naphthyl; anthracene; Fluorene; Phenanthrene; Benzophenanthrene; Fluoranthene; Pyrene; And triphenylene are selected.

As used herein, the heterocyclic group includes dihydroindenocarbazole; Dihydroindolocarbazole; Carbazole; Pyridine; Pyrimidine; Triazine; Benzisoquinoline; Dibenzothiophene; Dibenzofuran; Benzocarbazole; ≪ / RTI > and benzimidazole.

In one embodiment of the present specification, Y x is a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Y x is a naphthyl group substituted with a naphthyl group.

In one embodiment of the present specification, Y x is a naphthyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Y x is a fluorenyl group substituted with an alkyl group.

In one embodiment of the present disclosure, Y x is a substituted or unsubstituted phenanthrenyl moiety.

In one embodiment of the present disclosure, Y x is phenanthrene.

In one embodiment of the present specification, Y x is a substituted or unsubstituted benzophenanthrenyl moiety.

In one embodiment of the present disclosure, Y x is benzophenanthrenyl moiety.

In one embodiment of the present specification, Y x is a substituted or unsubstituted fluoranthene group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted anthracenyl group.

In one embodiment of the present specification, Y x is an anthracenyl group substituted with a phenyl group.

In one embodiment of the present specification, Y x is an anthracenyl group substituted with two phenyl groups.

In one embodiment of the present specification, Y x is an anthracenyl group substituted with a biphenyl group.

In one embodiment of the present specification, Y x is an anthracenyl group substituted with a naphthyl group.

In one embodiment of the present specification, Y x is an anthracenyl group substituted with two naphthyl groups.

In one embodiment of the present specification, Y x is an anthracene group having one substituent. in this case,

Figure pat00015
to be. * Is a moiety connected to L x, and R y is a substituent of an anthracene group.

In one embodiment of the present specification, Y x is an anthracene group having one substituent. in this case,

Figure pat00016
to be. * Is a moiety connected to L x, and R y and R y 'are the same or different and are each independently a substituent of an anthracene group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, Y x is a biphenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Y x is a phenyl group substituted with a phenyl group.

In one embodiment of the present specification, Y x is a phenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted triphenylene group.

In one embodiment of the present specification, Y x is a triphenylene group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted pyrenyl group.

In one embodiment of the present specification, Y x is a pyrenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted dihydroindenocarbazole group.

In one embodiment of the present specification, Y x is a dihydroindenocarbazole group substituted with an alkyl group.

In one embodiment of the present specification, Y x is a group in which two substituted or unsubstituted carbazole groups share a benzene ring and are condensed.

In one embodiment of the present specification, Y x is a substituted or unsubstituted dihydroindolocarbazole group.

In one embodiment of the present specification, Y x is a group in which two carbazole groups substituted with a phenyl group share a benzene ring and are condensed.

In one embodiment of the present specification, Y x is a dihydroindolocarbazole group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Y x is a phenyl group substituted with a carbazole group.

In one embodiment of the present specification, Y x is a phenyl group substituted with two carbazole groups.

In one embodiment of the present specification, Y x is a terphenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, Y x is a pyridine group substituted with a pyridine group.

In one embodiment of the present specification, Y x is a pyridine group substituted with two pyridine groups.

In one embodiment of the present specification, Y x is a substituted or unsubstituted benzisoquinoline group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted dibenzofurane group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted benzocarbazole group.

In one embodiment of the present specification, Y x is a benzocarbazole group substituted or unsubstituted with a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y x is a benzocarbazole group substituted or unsubstituted with a heterocyclic group containing at least one substituted or unsubstituted N atom.

In one embodiment of the present specification, Y x is a benzocarbazole group substituted or unsubstituted with a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Y x is a benzocarbazole group substituted or unsubstituted with a carbazole group substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, Y x is a benzocarbazole group substituted or unsubstituted with a carbazole group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted pyrimidine group.

In one embodiment of the present specification, Y x is a pyrimidine group substituted with a phenyl group.

In one embodiment of the present specification, Y x is a carbazol group substituted or unsubstituted with a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y x is a carbazol group substituted or unsubstituted with a heterocyclic group containing at least one substituted or unsubstituted N atom.

In one embodiment of the present specification, Y x is a carbazol group substituted or unsubstituted with a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Y x is a carbazol group substituted or unsubstituted with a carbazol group substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, Y x is a carbazol group substituted or unsubstituted with a carbazole group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted triazine group.

In one embodiment of the present specification, Y x is a triazine group substituted with a phenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted benzimidazole group.

In one embodiment of the present specification, Y x is a benzimidazole group substituted with a phenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted phosphine oxide group.

In one embodiment of the present specification, Y x is a phosphine oxide group substituted with a phenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted arylamine group.

In one embodiment of the present specification, Y x is an arylamine group substituted with a biphenyl group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted phenanthroline group.

In one embodiment of the present specification, Y x is a substituted or unsubstituted fluorenyl group, and the fluorenyl group is a structure in which two cyclic organic compounds are connected through one atom.

In one embodiment of the present specification, Y x is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, Y x is a methyl group.

In one embodiment of the present specification, Y x is an ethyl group.

In one embodiment of the present specification, Y x is a branched chain isopropyl group.

In the present specification, x is an integer of 1 to 5.

In one embodiment of the present specification, - (L x ) p x - (Y x ) q x is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment, - (L x ) p x - (Y x ) q x is -phenyl-naphthyl-naphthyl; A fluorine substituted with a phenyl-alkyl group; -Phenyl-phenanthrene; -Phenyl-fluoranthene; -Phenyl-benzophenanthrene; -Phenyl-anthracene-phenyl; -Phenyl-anthracene-biphenyl; -Phenyl-anthracene-naphthyl; -Pyridine-anthracene-phenyl; -Phenyl-anthracene-naphthyl; -Phenyl-anthracene-naphthyl; -Phenyl-anthracene-phenyl; -Phenyl-triphenylene; -Phenyl-pyrene; Dihydroindenocarbazole substituted with a phenyl-alkyl group; A dihydroindolocarbazole substituted with a phenyl-aryl group; Phenylcarbazole substituted with a carbazole group; - biphenyl-carbazole; -Phenyl-dibenzothiophene; - phenyl-dibenzofuran; - biphenyl-benzocarbazole; - triazine-phenyl substituted by a biphenyl-phenyl group; Phosphine oxides substituted with biphenyl-aryl groups; An amine group substituted with a phenyl-aryl group; A fluorene substituted with a naphthyl-alkyl group; Naphthyl-phenanthrene; - phenyl-spirobifluorene; -Phenyl-phenanthroline; - anthracene-phenyl; -Anthracene-naphthyl; - anthracene-biphenyl; Anthracene-naphthyl substituted with a naphthyl group; Anthracene-phenyl substituted with a phenyl group; - anthracene-phenyl; - phenyl; - alkyl of 1 to 10 carbon atoms; -Naphthyl-naphthyl; -Phenyl-benzocarbazole; Phenylcarbazole substituted with a carbazole group; Dihydroindeno nocabazole substituted with an alkyl group; Dihydroindolocarbazole substituted with an aryl group; -Naphthyl-dibenzothiophene; Triazine substituted with a biphenyl-phenyl group; - spirobifluorene; - terphenyl; Benzimidazole substituted with a phenyl-aryl group; Triazine substituted with a phenyl-phenyl group; Triazine-phenyl substituted by phenyl-phenyl groups; Pyridine-pyridine substituted with a phenyl-pyridine group; Pyridine substituted with a phenyl-pyridine group; -Phenyl-benzoquinoline; -Pyrimidine-phenyl substituted with a phenyl-phenyl group; A pyrimidine substituted with a phenyl-phenyl group; -Pyrimidine-phenyl substituted with a biphenyl-phenyl group; A pyrimidine substituted with a biphenyl-phenyl group; -Naphthyl-phenyl-phenyl group; -Naphthyl-phenyl-phenyl group; Triazin-phenyl substituted with a naphthyl-phenyl group; Triazine substituted with a naphthyl-phenyl group; -Phenyl-carbazole-carbazol-phenyl; A carbazole substituted with a phenyl-carbazole-aryl group; -Phenyl-benzocarbazole-carbazole-phenyl; Or-phenyl-benzocarbazole-aryl group.

In the present specification, the alkyl group may have 1 to 10 carbon atoms. In another embodiment, the aryl group may have from 6 to 30 carbon atoms. In still another embodiment, the heterocyclic group may have 2 to 30 carbon atoms.

In the present specification, the compound represented by the formula (1) is represented by any one of the following 2-1 to 2-68.

Figure pat00017

Figure pat00018

Figure pat00019

Figure pat00020

Figure pat00021

Figure pat00022

Figure pat00023

Figure pat00024

Figure pat00025

Figure pat00026

Figure pat00027

Figure pat00028

Figure pat00029

Figure pat00030

Figure pat00031

Figure pat00032

Figure pat00033

In one embodiment of the present invention, the compound represented by Formula 1 is represented by any one of the following Formulas 3-1 to 3-28.

Figure pat00034

Figure pat00035

Figure pat00036

Figure pat00037

Figure pat00038

Figure pat00039

Figure pat00040
.

In one embodiment of the present invention, the compound represented by Formula 1 is represented by any one of the following Formulas 4-1 to 4-68.

Figure pat00041

Figure pat00042

Figure pat00043

Figure pat00044

Figure pat00045

Figure pat00046

Figure pat00047

Figure pat00048

Figure pat00049

Figure pat00050

Figure pat00051

Figure pat00052

Figure pat00053

Figure pat00054

Figure pat00055

Figure pat00056

Figure pat00057

In one embodiment of the present invention, the compound represented by Formula 1 is represented by any one of the following Formulas 5-1 to 5-28.

Figure pat00058

Figure pat00059

Figure pat00060

Figure pat00061

Figure pat00062

Figure pat00063

Figure pat00064

The present specification has a characteristic suitable for being used as an organic material layer used in an organic electronic device by introducing various substituents with the nitrogen hetero heterocyclic structure represented by the above formula (1) as a core structure.

The compound represented by Formula 1 according to an embodiment of the present invention has a high glass transition temperature (Tg) and thus is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

The compound of formula (1) may be prepared based on the preparation examples described below.

Specifically, a core structure of a nitrogen-containing heterocyclic compound represented by the formula (1) is synthesized through a ring-closing reaction of a nitro group, a thiol group or a naphthalene substituted by a hydroxy group, and - (L x ) p x - (Y x ) q x (wherein x is an integer of 1 to 5) to produce a nitrogen-containing heterocyclic compound represented by the formula (1).

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 used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in the production of an organic electronic device including the organic light emitting device into the structure, Materials can be prepared. The compound of the present invention can be applied to an organic electronic device according to a conventional manufacturing method of an organic electronic device.

The present invention relates to an organic electronic 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 has a structure represented by Formula 1 And a nitrogen heterocyclic compound.

The organic electronic device may be selected from the group consisting of an organic solar cell, an organic light emitting device, an organic photoconductor (OPC) drum, and an organic transistor.

In one embodiment of the present invention, the organic electronic device is a single organic light emitting device.

In one embodiment of the present specification, at least one layer of the organic material layer includes at least a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, And a nitrogen-containing heterocyclic compound.

In one embodiment of the present disclosure, the hole injecting layer or the hole transporting layer includes the nitrogen-containing heterocyclic compound.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the nitrogen-containing heterocyclic compound.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and includes the nitrogen-containing heterocyclic compound as a host of the light emitting layer.

In one embodiment of the present invention, the nitrogen-containing heterocyclic compound is included as a host of the light-emitting layer and includes a phosphorescent dopant compound as a dopant.

In another embodiment, the nitrogen-containing heterocyclic compound is included as a host of the light-emitting layer, and includes a phosphorescent dopant compound represented by the following general formula (5) as a dopant.

[Chemical Formula 5]

Figure pat00065

In Formula 5,

M 1 is Ir or Os,

L 10 , L 11 and L 12 are the same or different and independently of each other are any one of the following structures,

Figure pat00066
,
Figure pat00067
,
Figure pat00068
,
Figure pat00069
,
Figure pat00070
,

Figure pat00071
,
Figure pat00072
,
Figure pat00073
,
Figure pat00074
,

Figure pat00075
,
Figure pat00076
,
Figure pat00077
And
Figure pat00078

p, r, s, t, v, y, b, d, f, h and l are each an integer of 0 to 4,

each of u, w, z, a, c, e, g, i and j is an integer of 0 to 6,

k is an integer of 0 to 8,

R 10 to R 41 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C 2 ~ 10; A substituted or unsubstituted C 6 ~ 30 arylsilyl group; A substituted or unsubstituted alkyl group of C 1-10; A substituted or unsubstituted C 2 ~ C 10 alkenyl; Alkoxy group, a substituted or unsubstituted C 1 ~ 10 ring; A substituted or unsubstituted C 6 -C 20 aryl group; And a substituted or unsubstituted C 5 to C 20 heterocyclic group, or adjacent groups form a condensed ring of monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic rings.

In one embodiment of the present invention, the phosphorescent dopant compound represented by Formula 5 is any one of the following compounds.

Figure pat00079
,
Figure pat00080
,
Figure pat00081
,
Figure pat00082
,

Figure pat00083
,
Figure pat00084
,
Figure pat00085
,
Figure pat00086
,

Figure pat00087
,
Figure pat00088
,
Figure pat00089
,
Figure pat00090
,

Figure pat00091
,
Figure pat00092
,
Figure pat00093
,
Figure pat00094
,

Figure pat00095
,
Figure pat00096
,
Figure pat00097

In one embodiment of the present invention, the phosphorescent dopant compound represented by Formula 5 is a phosphorescent dopant, and the phosphorescent dopant compound is a phosphorescent dopant. By weight based on the total weight of the material.

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, The nitrogen-containing heterocyclic compound is contained as a p-type host, and the n-type organic layer is doped.

In one embodiment of the present disclosure, the n-type dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound, or a combination thereof.

In another embodiment, the n-type dopant is selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Nd, Sm, Eu, Tb, Yb, LiF, Li2O, And one or two or more thereof are selected from the group consisting of the following compounds.

Figure pat00098
,
Figure pat00099
,
Figure pat00100
,
Figure pat00101
,

Figure pat00102
,
Figure pat00103
,
Figure pat00104
,
Figure pat00105
,

Figure pat00106
,
Figure pat00107
,
Figure pat00108

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer that simultaneously transports electrons and injects electrons into the electron transporting layer, the electron injecting layer, or the electron transporting and electron injecting Type dopant is present in an amount of 1 to 30% by weight, based on the total weight of the material constituting the layer, and the n-type dopant is present in an amount of 1 to 30% by weight based on the total weight of the electron transporting layer, 1 to 70% by weight.

The electron injection characteristics are improved in the above-mentioned range, and there is an advantage of increasing the efficiency of the device, lowering the driving voltage, and / or increasing the stability.

In one embodiment of the present invention, 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 in this specification 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.

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.

In one embodiment of the present invention, the organic electronic device is an organic solar cell.

In one embodiment of the present invention, the organic electronic device is an organic solar cell including a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers Provides an organic electronic device comprising the nitrogen-containing heterocyclic compound.

In one embodiment of the present disclosure, the organic layer includes a photoactive layer, and the photoactive layer includes the nitrogen-containing heterocyclic compound.

The present invention provides an organic solar cell, that is, a bulk heterojunction (BHJ) junction type organic solar cell including a photoactive layer in which an n-type semiconductor and a p-type semiconductor are blended.

Bulk heterojunction means that the electron donor material and the electron acceptor material are mixed in the photoactive layer.

In one embodiment of the present disclosure, the photoactive layer of the organic solar cell is an electron donor material or a mixture layer (bulk heterojunction) of an electron donor material and an electron acceptor material.

In the embodiment of the present invention, when the organic solar cell receives photons from an external light source, electrons and holes are generated between the electron beams and the electron acceptors. The generated holes are transported to the anode through the electron donor layer.

In an embodiment of the present disclosure, the organic solar cell may further include an additional organic layer. The organic solar cell can reduce the number of organic layers by using organic materials having various functions at the same time.

In one embodiment of the present disclosure, the organic electronic device is an organic transistor.

In one embodiment of the present disclosure, an organic transistor is provided that includes a source, a drain, a gate, and one or more organic layers.

In one embodiment of the present disclosure, the organic transistor comprises a charge generating layer, and the charge generating layer may comprise the nitrogen containing heterocyclic compound.

In another embodiment, the organic transistor may comprise an insulating layer, and the insulating layer may be located on the substrate and the gate.

In one embodiment of the present invention, the organic electronic device is an organophotoreceptor.

In one embodiment of the present specification, the organic electroluminescent device includes a first electrode, a second electrode, and at least one organic layer provided on the first electrode and the second electrode, the organic layer including an organic photosensitive layer, Layer or more comprises the nitrogen-containing heterocyclic compound.

In one embodiment of the present invention, the organic layer includes a charge generation layer, and the charge generation layer includes the nitrogen-containing heterocyclic compound.

In one embodiment of the present disclosure, the organic layer includes an ultraviolet light stabilizer, and the ultraviolet light stabilizer includes the nitrogen-containing heterocyclic compound.

In one embodiment of the invention, the organophotoreceptor may be in the form of, for example, a plate, a flexible belt, a disk, a rigid drum, a sheet around a rigid or compliant drum, and a rigid drum generally used for commercial purposes will be.

When the organic electronic device includes a plurality of organic layers, the organic layers may be formed of the same material or another material.

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

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

For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.

1 shows an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, the light emitting layer 5, or the electron transporting layer 6.

2 shows the structure of an organic electronic device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5 and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, or the electron transporting layer 6.

3 illustrates the structure of an organic electronic device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

4 illustrates the structure of an organic electronic device in which an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates the structure of an organic electronic device in which an anode 2, a light-emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1. As shown in Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

The organic electronic 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 includes the compound of the present invention, i.e., the nitrogen-containing heterocyclic compound.

For example, the organic electronic device of the present specification 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 electronic device can be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate. (International Patent Application Publication No. 2003/012890)

In addition, the nitrogen-containing heterocyclic compound can be formed into an organic material layer by a solvent process using a polymer material as well as a vacuum deposition method in the production of an organic electronic 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 this specification, the substrate can be selected in consideration of optical properties and physical properties as required. For example, the substrate is preferably transparent. The substrate may be of a rigid material, but may also be of a flexible material such as plastic.

As the material of the substrate, besides glass and quartz plate, a material such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene (PS), polyoxymethylene (acrylonitrile butadiene styrene copolymer), TAC (triacetyl cellulose), and PAR (polyarylate), but the present invention is not limited thereto.

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

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

The hole 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 hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. The hole injecting material preferably has a highest occupied molecular orbital (HOMO) between the work function of the cathode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic material, phthalocyanine derivative, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, Perylene-based organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, 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 electron transporting layer 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. Do. 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 method for preparing the compound of Formula 1 and the production of the organic electronic device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< Example >

< Example  1> Preparation of the compound of formula 2-6

[A-1] [A-2] [A-3]

Figure pat00109

[A-3] [A-4]

Figure pat00110

[A-4] [A-5] [Formula 2-6]

Figure pat00111

(1) Preparation of Compound A-3: Compound A-1 (25.0 g, 144.37 mmol) and Compound A-2 (39.69 g, 158.81 mmol) were dissolved in 300 mL of Acetone. Potassium carbonate (39.91 g, 288.74 mmol) was added and the mixture was heated to 120 ° C and refluxed for 6 hours. After completion of the reaction, the solid obtained by filtration was dissolved in 200 ml of CHCl 3 . The water was removed with anhydrous MgSO 4 , filtered and concentrated under reduced pressure. The obtained mixture was recrystallized from THF / EtOH to obtain Compound A-3 (33.70 g, 103.95 mmol, 72%).

MS: [M + H] &lt; + &gt; = 325

(2) Preparation of compound A-4: Compound A-3 (14.52 g, 44.79 mmol) was dissolved in 250 mL of anhydrous THF under nitrogen. The temperature was cooled to -78 ° C and then 2.5M n-butyllithium (21.50 mL, 53.75 mmol) was slowly added. After one hour, triisopropyl borate (20.67 mL, 89.58 mmol) was added. And the mixture was stirred for 3 hours while maintaining the temperature. After warming to room temperature, 250 mL of NH 4 Cl saturated in water was added and stirred for 1 hour. After completion of the reaction, the water layer was separated and extracted with ethyl acetate (EA). Remove moisture with anhydrous MgSO 4 , filter and concentrate under reduced pressure. The resulting mixture was recrystallized from CHCl 3 / Hexane to obtain Compound A-4 (11.78 g, 40.76 mmol, 91%).

MS: [M + H] &lt; + &gt; = 290

(10.38 g, 35.90 mmol) and Compound A-5 (10.88 g, 32.64 mmol) were dissolved in 200 ml of tetrahydrofuran (THF) under nitrogen. Potassium carbonate (14.89 g, 107.7 mmol) and tetrakis (triphenyl-phosphine) palladium (1.25 g, 1.08 mmol) dissolved in 100 mL of water were charged and heated to 120 ° C. for 8 hours Lt; / RTI &gt; After completion of the reaction, the water layer was separated and the organic layer was extracted with dichloromethane (DCM). The water was removed with anhydrous MgSO 4 , filtered and concentrated under reduced pressure. The concentrate was recrystallized from CHCl 3 / EtOH to obtain the compound of Formula 2-6 (15.36 g, 30.87 mmol, 91%).

MS: [M + H] &lt; + &gt; = 498

< Example  2> Preparation of compound of formula 2-7

[A-4] [A-6] [Chemical Formula 2-7]

Figure pat00112

Compound A-4 (14.19 g, 49.08 mmol) and Compound A-6 (18.26 g, 44.62 mmol) were dissolved in 200 ml of tetrahydrofuran (THF) under nitrogen. Potassium carbonate (20.35 g, 147.24 mmol) and tetrakis (triphenyl-phosphine) palladium (1.25 g, 1.08 mmol) dissolved in 100 mL of water were added and heated to 120 ° C. The mixture was heated and refluxed for 13 hours. After completion of the reaction, the water layer was separated and extracted with dichloromethane (DCM). The water was removed with anhydrous MgSO 4 , filtered and concentrated under reduced pressure. The concentrate was recrystallized from CHCl 3 / EtOH to obtain the compound of Formula 2-7 (23.37 g, 40.74 mmol, 83%).

MS: [M + H] &lt; + &gt; = 574

< Example  3> Preparation of the compound of the formula 2-29

[A-7] [A-8] [A-9]

Figure pat00113

[A-10]

Figure pat00114

                        [A-11] [Chemical Formula 2-29]

Figure pat00115

(1) Preparation of compound A-9: Compound A-7 (25.0 g, 144.37 mmol) and compound A-8 (27.16 g, 158.81 mmol) were dissolved in 300 mL of acetone. Potassium carbonate (39.91 g, 288.74 mmol) was added and the mixture was heated to 120 ° C and refluxed for 12 hours. After completion of the reaction, the residue obtained by filtration is dissolved in 200 ml of CHCl 3 . The water was removed with anhydrous MgSO 4 , filtered and concentrated under reduced pressure. The resulting mixture was recrystallized from THF / EtOH to obtain Compound A-9 (21.95 g, 89.51 mmol, 62%).

MS: [M + H] &lt; + &gt; = 246

(2) Preparation of Compound A-10: Compound A-9 (13.27 g, 54.10 mmol) was dissolved in 200 mL of CHCl 3 . N-bromosuccinimide (10.58 g, 59.51 mmol) was added slowly after the temperature was lowered to 0 ° C, the temperature was gradually raised to room temperature, and the mixture was stirred for 4 hours. After completion of the reaction, 200 mL of H 2 O was added to the reaction solution, and the reaction was terminated and extracted with dichloromethane (DCM). After the water layer was removed, the organic layer was dried over MgSO 4 , filtered and concentrated under reduced pressure. The resulting mixture was recrystallized from THF / EtOH to obtain Compound A-10 (16.66 g, 51.40 mmol, 95%).

MS: [M + H] &lt; + &gt; = 325

(3) Preparation of Compound (2-29) Compound A-10 (9.74 g, 30.05 mmol) and Compound A-11 (9.92 g, 33.06 mmol) were dissolved in 160 ml of tetrahydrofuran (THF) under nitrogen. To the 80 mL of water was added potassium carbonate (12.46 g, 90.15 mmol) and tetrakis (triphenyl-phosphine) palladium (1.04 g, 0.90 mmol) And refluxed for 18 hours. After completion of the reaction, the water layer was separated and extracted with dichloromethane (DCM). The organic layer was dried over anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The concentrated reaction mixture was recrystallized from CHCl 3 / EtOH to obtain the compound of Formula 2-29 (10.92 g, 21.94 mmol, 73%).

MS: [M + H] &lt; + &gt; = 498

< Example  4> 34 of  Preparation of compounds

[A-12] [A-13]

Figure pat00116

                     [A-11]         [Chemical Formula 2-34]

Figure pat00117

(1) Preparation of Compound A-13: Compound A-12 (16.54 g, 90.28 mmol) was dissolved in 200 mL of CHCl 3 . N-bromosuccinimide (17.68 g, 99.31 mmol) was added slowly after the temperature was lowered to 0 占 폚, and then the temperature was slowly raised to room temperature and stirred for 2 hours. After completion of the reaction, 200 mL of H 2 O was added to the reaction solution, and the reaction was terminated and extracted with dichloromethane (DCM). The organic layer is dried over MgSO 4, filtered, and concentrated under reduced pressure. The resulting reaction mixture was recrystallized from THF / EtOH to obtain Compound 2 (22.24 g, 84.86 mmol, 94%).

MS: [M + H] &lt; + &gt; = 263

(11.23 g, 42.84 mmol) and Compound A-11 (9.92 g, 99.31 mmol) were dissolved in 180 ml of tetrahydrofuran (THF) under nitrogen. Potassium carbonate (17.76 g, 128.52 mmol) and tetrakis (triphenyl-phosphine) palladium (1.49 g, 1.29 mmol) dissolved in 90 mL of water were added and heated to 120 ° C. The mixture was heated and refluxed for 5 hours. After completion of the reaction, the water layer was separated and extracted with dichloromethane (DCM). The organic layer was dried over anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The concentrate was recrystallized from CHCl 3 / EtOH to obtain the compound of Formula 2-34 (14.25 g, 32.56 mmol, 76%).

MS: [M + H] &lt; + &gt; = 436

< Example  5> 67 of  Preparation of compounds

Figure pat00118

(10.0 g, 30.96 mmol), 9-phenyl-9H, 9H'-3,3'-bicarbazole (9-phenyl-9H, 9'H-3,3 -bicarbazole (12.69g, 30.96mmol) was completely dissolved in 300ml of xylene, sodium tert-butoxide (3.87g, 40.25mmol) was added, and bis (tri- after loading the butylphosphine) palladium (0) (Bis (tri- tert -butylphosphine) palladium (0)) (0.16g, 0.31mmol) was added and the mixture was heated and stirred for 6 hours. After lowering the temperature to room temperature, the base was removed by filtration, the xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to obtain 2-67 (15.61 g, yield: 85 %).

MS [M + H] &lt; + &gt; = 652

< Example  6> Preparation of the compound of formula 4-6

[B-1] [B-2] [B-3]

Figure pat00119

[B-3] [B-4]

Figure pat00120

[B-4] [B-5] [Formula 4-6]

Figure pat00121

(1) Preparation of compound B-3: Compound B-1 (12.5 g, 72.19 mmol) and compound A-2 (19.91 g, 79.41 mmol) were dissolved in 300 mL of acetone. Potassium carbonate (19.82 g, 144.37 mmol) was added and the mixture was heated to 120 ° C and refluxed for 5 hours. After completion of the reaction, the solid obtained by filtration was dissolved in 400 ml of chloroform (CHCl 3 ). Water was removed with anhydrous magnesium sulfate (MgSO 4 ), filtered and concentrated under reduced pressure. The resulting mixture was recrystallized from THF / EtOH to obtain Compound B-3 (30.40 g, 91.88 mmol, 64%).

MS: [M + H] &lt; + &gt; = 339

(2) Preparation of compound B-4: Compound B-3 (14.52 g, 44.79 mmol) was dissolved in 250 mL of anhydrous THF under nitrogen. The temperature was cooled to -78 ° C and then 2.5M n-butyllithium (21.50 mL, 53.75 mmol) was slowly added. After one hour, triisopropyl borate (20.67 mL, 89.58 mmol) was added. And the mixture was stirred for 3 hours while maintaining the temperature. After warming to room temperature, 250 mL of saturated ammonium chloride (NH 4 Cl) was added and stirred for 1 hour. After completion of the reaction, the water layer was separated and extracted with ethyl acetate (EA). Remove water with anhydrous magnesium sulfate (MgSO 4 ), filter and concentrate under reduced pressure. The resulting mixture was recrystallized from CHCl 3 / Hexane to obtain Compound B-4 (11.78 g, 40.76 mmol, 91%).

MS: [M + H] &lt; + &gt; = 305

(10.38 g, 35.90 mmol) and Compound A-5 (10.88 g, 32.64 mmol) were dissolved in 200 ml of tetrahydrofuran (THF) under nitrogen. Potassium carbonate (14.89 g, 107.7 mmol) and tetrakis (triphenyl-phosphine) palladium (1.25 g, 1.08 mmol) dissolved in 100 mL of water were charged and heated to 120 ° C. The mixture was heated and refluxed for 8 hours. After completion of the reaction, the water layer was separated and the organic layer was extracted with dichloromethane (DCM). The water was removed with anhydrous magnesium sulfate (MgSO 4 ), filtered and concentrated under reduced pressure. The concentrate was recrystallized from CHCl 3 / EtOH to obtain the compound of formula 4-6 (13.86 g, 26.69 mmol, 83%).

MS: [M + H] &lt; + &gt; = 514

< Example  7> Preparation of compound of formula 4-7

In the same manner as in Example 2 except that B-4 was used instead of A-4 in Example 2, the following Formula 4-7 was synthesized.

Figure pat00122

MS: [M + H] &lt; + &gt; = 590

< Example  8> Preparation of the compound of formula 4-67

In the same manner as in Example 5 except that B-4 was used instead of A-4 in Example 5, the following Formula 4-67 was synthesized.

Figure pat00123

MS: [M + H] &lt; + &gt; = 668

< Comparative Example  1>

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

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

(60 nm) / TCTA (80 nm) / CBP + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) using CBP as a host on the prepared ITO transparent electrode. ) / LiF (1 nm) / Al (200 nm) were fabricated in this order to produce an organic EL device. The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.

Figure pat00124

< Experimental Example  1-1>

An organic light emitting device was prepared in the same manner as in Comparative Example 1, except that the compound of Formula 2-67 was used in place of CBP in Comparative Example 1.

< Experimental Example  1-2>

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound of Formula 4-67 was used instead of CBP in Comparative Example 1.

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

compound Voltage
(V @ 10 mA / cm 2 )
efficiency
(cd / A @ 10mA / cm 2)
EL peak
(nm)
Comparative Example 1 CBP 8.32 34.12 516 Experimental Example 1-1 Formula 2-67 6.60 42.31 517 Experimental Example 1-2 Formula 4-67 6.62 42.64 517

As a result of the experiment, the green organic EL devices of Experimental Examples 1-1 and 1-2 using the compound represented by the present invention as the host material of the light emitting layer showed higher current efficiency than the green organic EL device of Comparative Example 1 using CBP And the driving voltage.

< Experimental Example  2>

The compounds synthesized in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, and red organic light emitting devices were prepared as follows.

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the base pressure was adjusted to 1 x 10 &lt; -6 &gt; torr. Then, organic substances were injected onto the ITO using DNTPD (700 ANGSTROM), alpha -NPB (300 ANGSTROM) and a 4-67 as a host (90 wt%) used, and to (piq) 2 Ir (acac) co-deposited (300 Å) to (10 wt%) as a dopant, Alq 3 (350 Å), LiF ( 5 Å), and Al (1,000 Å) in this order and measured at 0.4 mA.

The DNTPD, alpha-NPB, (piq) 2 Ir (acac), Alq 3 The structure of

Figure pat00125

< Comparative Example  2>

The organic light emitting device for Comparative Example 2 was fabricated in the same manner except that CBP, which is commonly used as a general phosphorescent host material, was used instead of the organic light emitting compound prepared by the present invention as a host of a light emitting layer in the device structure of the above embodiment.

The voltage, the current density, the luminance, the color coordinate, and the lifetime of the organic light emitting device manufactured according to the following Experimental Examples 2-1 and 2-2 and Comparative Example 2 were measured, and the results are shown in Table 2 below. T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

Host Dopant Voltage (V) Luminance
(cd / m 2 )
CIEx
CIEy T95 (hr)
Experimental Example 2-1 2-67 [(piq) 2 Ir (acac)] 4.0 1790 0.675 0.333 405 EXPERIMENTAL EXAMPLE 2-2 4-67 [(piq) 2 Ir (acac)] 4.3 1860 0.668 0.329 465 Comparative Example 2 CBP [(piq) 2 Ir (acac)] 6.5 960 0.679 0.339 230

As a result of the experiment, the red organic light emitting devices of Experimental Examples 2-1 and 2-2 of Experimental Example 2 using the compounds represented by 2-67 and 4-67 according to the present invention as the host material of the light emitting layer, It was confirmed that the red organic EL device of Comparative Example 2 used exhibited excellent performance in current efficiency, driving voltage and life span.

< Experimental Example  3-1>

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

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

[LINE]

Figure pat00126

(4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 angstroms) as a hole transporting material was vacuum deposited on the hole injection layer to form a hole transport layer Respectively.

[NPB]

Figure pat00127

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

[BH]

Figure pat00128

[BD]

Figure pat00129

[LiQ]

Figure pat00130

The compound of Formula 2-6 prepared in Preparation Example 1 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  3-2>

In the same manner as in Experimental Example 3-1, except that the compound of Formula 2-7 was used in place of the compound of Formula 2-6 as the electron transport layer.

< Experimental Example  3-3>

The same experiment was conducted except that the compound of Chemical Formula 2-29 was used as an electron transporting layer in Experimental Example 3-1 instead of the compound of Chemical Formula 2-6.

< Experimental Example  3-4>

In the same manner as in Experimental Example 3-1 except that the compound of Formula 2-34 was used in place of the compound of Formula 2-6 as the electron transport layer.

< Experimental Example  3-5>

In the same manner as in Experimental Example 3-1, except that the compound of Formula 4-6 was used in place of the compound of Formula 2-6 as the electron transport layer.

< Experimental Example  3-6>

In the same manner as in Experimental Example 3-1 except that the compound of Formula 4-7 was used in place of the compound of Formula 2-6 as the electron transport layer.

< Comparative Example  3>

In the same manner as in Experimental Example 3-1, except that the following compound ET 1 was used instead of the compound of Formula 2-6 as an electron transporting layer.

[ET 1]

Figure pat00131

The results shown in Table 3 were obtained when current was applied to the organic light-emitting devices manufactured by Experimental Examples 3-1 to 3-6 and Comparative Example 3.

compound Voltage
(V @ 10 mA / cm 2 )
efficiency
(cd / A @ 10mA / cm 2)
EL peak
(nm)
Experimental Example 3-1 2-6 6.88 41.93 517 Experimental Example 3-2 2-7 6.96 42.24 516 Experimental Example 3-3 (2-29) 6.85 41.79 518 Experimental Example 3-4 2-34 6.19 46.15 517 Experimental Example 3-5 4-6 6.23 45.63 516 Experimental Example 3-6 4-7 6.29 45.62 516 Comparative Example 3 ET 1 7.27 32.52 517

As shown in Table 1, it was confirmed that the organic light emitting device using Experimental Examples 3-1 to 3-6 as the electron transporting layer exhibited superior performance in terms of current efficiency, driving voltage and lifetime than the organic light emitting device of Comparative Example 3 there was.

While the present invention has been described with reference to the preferred embodiments (the green luminescent layer, the red luminescent layer, and the electron transport layer) through the above description, the present invention is not limited thereto and various modifications may be made within the scope of the claims and the detailed description of the invention And it is also within the scope of the invention.

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

Claims (21)

A nitrogen-containing heterocyclic compound represented by the following formula (1)
[Chemical Formula 1]
Figure pat00132

In formula (1)
X is O or S,
R 1 is - (L 1) p 1 - (Y 1) , and q 1, R 2 is - (L 2) p 2 - (Y 2) and q 2, R 3 is - (L 3) p 3 - ( Y 3 ) q 3 , R 4 is - (L 4 ) p 4 - (Y 4 ) q 4 and R 5 is - (L 5 ) p 5 - (Y 5 ) q 5 ,
p 1 to p 5 each represent an integer of 0 to 10,
q 1 to q 5 each represent an integer of 1 to 10,
If more than p x is 2, L x is the same or different from each other,
When q x is 2 or more, Y x are the same or different from each other,
x is an integer of 1 to 5,
At least two adjacent substituents out of R 2 to R 5 form a monocyclic or polycyclic aliphatic, aromatic, aliphatic hetero or aromatic hetero condensation ring,
Said fused ring being selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy 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 alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group,
L 1 to L 5 are the same or different and are each independently a direct bond; Oxygen; sulfur; Substituted or unsubstituted nitrogen; Substituted or unsubstituted phosphorus; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; Or a substituted or unsubstituted heterocyclic group,
Y 1 to Y 5 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A 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 alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or forms a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group or forms a spiro bond.
The method according to claim 1,
Wherein the compound represented by the formula (1) is any one of the following formulas (2) to (4):
(2)
Figure pat00133

(3)
Figure pat00134

[Chemical Formula 4]
Figure pat00135

In formulas (2) to (4)
X, R 1 to R 5 are the same as defined in formula (1)
m, n and o are each an integer of 0 to 4,
R 6 to R 8 are the same as or different from each other and are the same as defined for R 1 to R 5 , respectively.
The method according to claim 1,
When p x is 0,
Y x is deuterium; A nitrile group; A halogen group; A substituted or unsubstituted boron group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
The method according to claim 1,
When p x is 1 or more,
L x is a substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heterocyclic group,
Y x is a substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (2-1) to (2-68):
Figure pat00136

Figure pat00137

Figure pat00138

Figure pat00139

Figure pat00140

Figure pat00141

Figure pat00142

Figure pat00143

Figure pat00144

Figure pat00145

Figure pat00146

Figure pat00147

Figure pat00148

Figure pat00149

Figure pat00150

Figure pat00151

Figure pat00152
.
The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (3-1) to (3-28)

Figure pat00153

Figure pat00154

Figure pat00155

Figure pat00156

Figure pat00157

Figure pat00158

Figure pat00159
.
The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (4-1) to (4-68):
Figure pat00160

Figure pat00161

Figure pat00162

Figure pat00163

Figure pat00164

Figure pat00165

Figure pat00166

Figure pat00167

Figure pat00168

Figure pat00169

Figure pat00170

Figure pat00171

Figure pat00172

Figure pat00173

Figure pat00174

Figure pat00175

Figure pat00176
.
The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (5-1) to (5-28):
Figure pat00177

Figure pat00178

Figure pat00179

Figure pat00180

Figure pat00181

Figure pat00182

Figure pat00183
.
1. An organic electronic device comprising a first electrode, a second 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 is provided in any one of claims 1 to 8 And a nitrogen-containing heterocyclic compound. The method of claim 9,
Wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic solar cell, and an organic transistor.
The method of claim 9,
Wherein the organic electronic device includes at least one organic layer disposed between a first electrode, a second electrode, and the first electrode and the second electrode, wherein at least one of the organic layers includes the nitrogen hetero-ring Organic compound layer.
The method of claim 11,
Wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the forward transport layer comprises the nitrogen-containing heterocyclic compound.
The method of claim 11,
Wherein the organic material layer includes a light emitting layer, the light emitting layer contains the nitrogen-containing heterocyclic compound as a host, and the phosphorescent dopant compound is contained as a dopant.
14. The method of claim 13,
Wherein the phosphorescent dopant compound is represented by the following Chemical Formula 5:
[Chemical Formula 5]
Figure pat00184

In Formula 5,
M 1 is Ir or Os,
L 10 , L 11 and L 12 are the same or different and independently of each other are any one of the following structures,
Figure pat00185
,
Figure pat00186
,
Figure pat00187
,
Figure pat00188
,
Figure pat00189
,
Figure pat00190
,
Figure pat00191
,
Figure pat00192
,
Figure pat00193
,
Figure pat00194
,
Figure pat00195
,
Figure pat00196
And
Figure pat00197

p, r, s, t, v, y, b, d, f, h and l are each an integer of 0 to 4,
each of u, w, z, a, c, e, g, i and j is an integer of 0 to 6,
k is an integer of 0 to 8,
R 10 to R 41 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C 2 ~ 10; A substituted or unsubstituted C 6 ~ 30 arylsilyl group; A substituted or unsubstituted alkyl group of C 1-10; A substituted or unsubstituted C 2 ~ C 10 alkenyl; Alkoxy group, a substituted or unsubstituted C 1 ~ 10 ring; A substituted or unsubstituted C 6 -C 20 aryl group; And a substituted or unsubstituted C 5 to C 20 heterocyclic group, or adjacent groups form a condensed ring of monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic rings.
15. The method of claim 14,
Wherein the phosphorescent dopant compound represented by Formula 5 is any one of the following compounds:
Figure pat00198
,
Figure pat00199
,
Figure pat00200
,
Figure pat00201
,
Figure pat00202
,
Figure pat00203
,
Figure pat00204
,
Figure pat00205
,
Figure pat00206
,
Figure pat00207
,
Figure pat00208
,
Figure pat00209
,
Figure pat00210
,
Figure pat00211
,
Figure pat00212
,
Figure pat00213
,
Figure pat00214
,
Figure pat00215
,
Figure pat00216
.
14. The method of claim 13,
The light emitting layer contains 1 to 50% by weight of the nitrogen-containing heterocyclic compound based on the total weight of the materials constituting the light emitting layer,
Wherein the phosphorescent dopant compound is 1 to 50% by weight based on the total weight of the materials constituting the light emitting layer.
The method of claim 11,
Wherein the organic material layer includes an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, or the layer that simultaneously transports electrons and electron injects the p- Type host, and an n-type dopant as a dopant.
18. The method of claim 17,
Wherein the n-type dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound, or a combination thereof.
18. The method of claim 17,
The n-type dopant may be selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Nd, Sm, Eu, Tb, Yb, LiF, Li2O, CsF, Or two or more organic electroluminescent elements.
Figure pat00217
,
Figure pat00218
,
Figure pat00219
,
Figure pat00220
,
Figure pat00221
,
Figure pat00222
,
Figure pat00223
,
Figure pat00224
,
Figure pat00225
,
Figure pat00226
,
Figure pat00227
.
The method of claim 9,
Wherein the organic electronic device includes an organic material layer disposed between the first electrode and the second electrode, the organic material layer including a first electrode, a second electrode, and at least one layer of the organic material layer including the nitrogen-containing heterocyclic compound Organic electronic device.
The method of claim 9,
Wherein the organic electronic device includes an organic transistor including a source, a drain, a gate, and one or more organic layers, and at least one of the organic layers includes the nitrogen-containing heterocyclic compound.
KR1020150073254A 2014-05-26 2015-05-26 Nitrogen-containing heterocyclic compounds and organic electronic device using the same KR101777454B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020140063299 2014-05-26
KR20140063299 2014-05-26

Publications (2)

Publication Number Publication Date
KR20150136033A true KR20150136033A (en) 2015-12-04
KR101777454B1 KR101777454B1 (en) 2017-09-12

Family

ID=54867613

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020150073254A KR101777454B1 (en) 2014-05-26 2015-05-26 Nitrogen-containing heterocyclic compounds and organic electronic device using the same

Country Status (1)

Country Link
KR (1) KR101777454B1 (en)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170037788A (en) * 2015-09-25 2017-04-05 엘지디스플레이 주식회사 Organic Light Emitting Diode Device
WO2017078403A1 (en) * 2015-11-03 2017-05-11 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
WO2017175986A1 (en) 2016-04-08 2017-10-12 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
WO2018155942A1 (en) * 2017-02-27 2018-08-30 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
KR20180099487A (en) * 2017-02-27 2018-09-05 롬엔드하스전자재료코리아유한회사 A plurality of host materials and organic electroluminescent device comprising the same
CN108779393A (en) * 2016-04-08 2018-11-09 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and Organnic electroluminescent device comprising it
CN109651291A (en) * 2019-01-22 2019-04-19 湘潭大学 A kind of polysubstituted naphtho- [1,2-d] thiazole and derivative and its synthetic method
KR102046983B1 (en) * 2018-08-03 2019-11-20 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
CN113024566A (en) * 2021-01-28 2021-06-25 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, electronic element comprising same and electronic device
KR20210104602A (en) * 2020-02-17 2021-08-25 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
KR20210104601A (en) * 2020-02-17 2021-08-25 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
CN114315871A (en) * 2022-03-10 2022-04-12 浙江华显光电科技有限公司 Phenanthroline compound, organic electroluminescent device and display or lighting device
WO2022080696A1 (en) * 2020-10-15 2022-04-21 주식회사 랩토 High-refractive-index benzazole derivative, and organic electroluminescent device comprising same
CN114853749A (en) * 2022-05-10 2022-08-05 长春海谱润斯科技股份有限公司 Heterocyclic compound and organic electroluminescent device comprising same
WO2022182153A1 (en) * 2021-02-24 2022-09-01 주식회사 엘지화학 Novel compound and organic light emitting device using same
CN115521301A (en) * 2022-02-23 2022-12-27 陕西莱特迈思光电材料有限公司 Nitrogen-containing compound, organic electroluminescent device comprising same and electronic device
CN115745906A (en) * 2022-09-07 2023-03-07 长春海谱润斯科技股份有限公司 Compound containing heterocycle and organic electroluminescent device thereof
WO2024039056A1 (en) * 2022-08-16 2024-02-22 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device thereof
CN118005621A (en) * 2023-03-07 2024-05-10 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device and electronic device

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220121215A (en) * 2021-02-24 2022-08-31 주식회사 엘지화학 Organic light emitting device
KR20240150626A (en) 2023-04-06 2024-10-16 듀폰스페셜티머터리얼스코리아 유한회사 A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH567054A5 (en) 1972-03-08 1975-09-30 Ciba Geigy Ag
JP2001013617A (en) 1999-06-29 2001-01-19 Konica Corp Silver halide emulsion, silver halide photosensitive material and heat developable photosensitive material
JP4552417B2 (en) * 2003-10-20 2010-09-29 東レ株式会社 Light emitting device material and light emitting device using the same
JP5611538B2 (en) 2008-05-16 2014-10-22 株式会社半導体エネルギー研究所 Benzoxazole derivative, and light-emitting element, light-emitting device, lighting device, and electronic device using benzoxazole derivative

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230022921A (en) * 2015-09-25 2023-02-16 엘지디스플레이 주식회사 Organic Light Emitting Diode Device
KR20230166062A (en) * 2015-09-25 2023-12-06 엘지디스플레이 주식회사 Organic Light Emitting Diode Device
KR20170037788A (en) * 2015-09-25 2017-04-05 엘지디스플레이 주식회사 Organic Light Emitting Diode Device
WO2017078403A1 (en) * 2015-11-03 2017-05-11 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
US10727416B2 (en) 2016-04-08 2020-07-28 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN108779393A (en) * 2016-04-08 2018-11-09 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and Organnic electroluminescent device comprising it
CN114591314A (en) * 2016-04-08 2022-06-07 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and organic electroluminescent device comprising the same
JP2019518324A (en) * 2016-04-08 2019-06-27 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド Organic electroluminescent compound and organic electroluminescent device comprising the same
US10927103B1 (en) 2016-04-08 2021-02-23 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
WO2017175986A1 (en) 2016-04-08 2017-10-12 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN108779393B (en) * 2016-04-08 2022-05-13 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and organic electroluminescent device comprising the same
KR20180099487A (en) * 2017-02-27 2018-09-05 롬엔드하스전자재료코리아유한회사 A plurality of host materials and organic electroluminescent device comprising the same
WO2018155942A1 (en) * 2017-02-27 2018-08-30 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
KR102046983B1 (en) * 2018-08-03 2019-11-20 (주)피엔에이치테크 An electroluminescent compound and an electroluminescent device comprising the same
CN109651291B (en) * 2019-01-22 2023-07-07 广东蓝天优创美化妆品有限公司 Polysubstituted naphtho [1,2-d ] thiazole and derivative and synthesis method thereof
CN109651291A (en) * 2019-01-22 2019-04-19 湘潭大学 A kind of polysubstituted naphtho- [1,2-d] thiazole and derivative and its synthetic method
KR20210104601A (en) * 2020-02-17 2021-08-25 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
KR20210104602A (en) * 2020-02-17 2021-08-25 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
WO2022080696A1 (en) * 2020-10-15 2022-04-21 주식회사 랩토 High-refractive-index benzazole derivative, and organic electroluminescent device comprising same
CN113024566B (en) * 2021-01-28 2021-11-30 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, electronic element comprising same and electronic device
WO2022160661A1 (en) * 2021-01-28 2022-08-04 陕西莱特光电材料股份有限公司 Nitrogen-containing compound and electronic element comprising same, and electronic apparatus
US11618754B2 (en) 2021-01-28 2023-04-04 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic component and electronic device including same
CN113024566A (en) * 2021-01-28 2021-06-25 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, electronic element comprising same and electronic device
WO2022182153A1 (en) * 2021-02-24 2022-09-01 주식회사 엘지화학 Novel compound and organic light emitting device using same
CN115521301A (en) * 2022-02-23 2022-12-27 陕西莱特迈思光电材料有限公司 Nitrogen-containing compound, organic electroluminescent device comprising same and electronic device
CN114315871A (en) * 2022-03-10 2022-04-12 浙江华显光电科技有限公司 Phenanthroline compound, organic electroluminescent device and display or lighting device
CN114853749A (en) * 2022-05-10 2022-08-05 长春海谱润斯科技股份有限公司 Heterocyclic compound and organic electroluminescent device comprising same
WO2024039056A1 (en) * 2022-08-16 2024-02-22 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device thereof
CN115745906A (en) * 2022-09-07 2023-03-07 长春海谱润斯科技股份有限公司 Compound containing heterocycle and organic electroluminescent device thereof
CN118005621A (en) * 2023-03-07 2024-05-10 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device and electronic device
WO2024183260A1 (en) * 2023-03-07 2024-09-12 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic apparatus

Also Published As

Publication number Publication date
KR101777454B1 (en) 2017-09-12

Similar Documents

Publication Publication Date Title
KR101777454B1 (en) Nitrogen-containing heterocyclic compounds and organic electronic device using the same
KR101917953B1 (en) Compound and organic electronic device comprising the same
KR101907292B1 (en) Amine-based compound and organic light emitting device comprising the same
KR101676102B1 (en) Heterocyclic compound and organic light emitting device using the same
KR101780595B1 (en) Heterocyclic compound and organic light emitting device comprising the same
KR101991050B1 (en) Spiro structure compound and organic light emitting device comprising the same
KR102202886B1 (en) Heterocyclic compound and organic light emitting device comprising the same
KR101607749B1 (en) Nitrogen-containing heterocyclic compounds and organic electronic device comprising the same
EP3327024B1 (en) Heterocyclic compound and organic light emitting diode comprising same
KR101916572B1 (en) Compound and organic light electronic device comprising the same
KR20170092097A (en) Amine-based compound and organic light emitting device comprising the same
KR102032023B1 (en) Compound and organic electronic device comprising the same
JP6638925B2 (en) Heterocyclic compound and organic light emitting device containing the same
KR101984081B1 (en) Hetero-cyclic compound and organic light emitting device comprising the same
KR102120917B1 (en) An electroluminescent compound and an electroluminescent device comprising the same
KR102235477B1 (en) Novel hetero-cyclic compound and organic light emitting device comprising the same
KR101899716B1 (en) Electroluminescence material and organic light emitting device using the same
KR101753465B1 (en) Carbazole derivatives and organic light emitting device comprising the same
KR102474920B1 (en) Novel compound and organic light emitting device comprising the same
KR101936216B1 (en) Compound and organic electronic device comprising the same
KR101913504B1 (en) Compound and organic electronic device comprising the same
KR101914380B1 (en) Compound and organic electronic device comprising the same
KR102028242B1 (en) Compound and organic electronic device comprising the same
KR20210010407A (en) Compound and organic light emitting device comprising the same
KR101850242B1 (en) Compound and organic electronic device using the same

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
AMND Amendment
E601 Decision to refuse application
AMND Amendment
X701 Decision to grant (after re-examination)
GRNT Written decision to grant