KR20160064029A - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents
Hetero-cyclic compound and organic light emitting device comprising the same Download PDFInfo
- Publication number
- KR20160064029A KR20160064029A KR1020150167403A KR20150167403A KR20160064029A KR 20160064029 A KR20160064029 A KR 20160064029A KR 1020150167403 A KR1020150167403 A KR 1020150167403A KR 20150167403 A KR20150167403 A KR 20150167403A KR 20160064029 A KR20160064029 A KR 20160064029A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- substituted
- unsubstituted
- layer
- heterocyclic
- Prior art date
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H01L51/0071—
-
- H01L51/5012—
-
- H01L51/5048—
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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 heterocyclic compounds and organic light emitting devices containing them.
Description
This specification claims the benefit of priority based on Korean Patent Application No. 10-2014-0167847 filed with the Korean Intellectual Property Office on Nov. 27, 2014, and all contents disclosed in the relevant Korean patent application are incorporated herein by reference .
The present invention relates to heterocyclic compounds and organic light emitting devices containing them.
In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.
Development of new materials for such organic light emitting devices has been continuously required.
Therefore, the present inventors aim to provide a heterocyclic compound having a chemical structure capable of performing various functions required in an organic light emitting device according to a substituent, and an organic light emitting device including the heterocyclic compound.
The present invention provides a heterocyclic compound represented by the following formula (1).
[Chemical Formula 1]
In formula (1)
Cy1 is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle,
X is CRR ';NR;O;S;SO; SO 2 ; Or SiRR '
R, R 'and R1 to R7 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; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two adjacent substituents are bonded to each other to form a hydrocarbon ring or a heterocyclic ring.
Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound described above.
The heterocyclic compound according to one embodiment of the present invention can be used as a material of an organic light emitting device, and an organic light emitting device including the same can improve a high efficiency, a low driving voltage, and / or a long life characteristic.
In addition, the heterocyclic compound according to one embodiment of the present invention has a high glass transition temperature (Tg), which is excellent in chemical stability. Particularly, in the case of NPB (N, N-diphenyl-1,1-biphenyl-4,4-diamine) used as a hole injecting and / or transporting layer in a conventional organic light emitting device, A problem that is difficult to apply in an organic light-emitting device of the present invention occurs. The heterocyclic compound according to one embodiment of the present invention can be expected to have improved lifetime characteristics due to its high glass transition temperature.
1 shows an example of an organic light emitting device in which a
2 shows an organic light emitting device in which a
Hereinafter, the present invention will be described in more detail.
The present invention provides a heterocyclic compound represented by the above formula (1).
According to one embodiment of the present invention, the heterocyclic compound includes a structure in which a ring structure including X is condensed at positions 10 and 11 of benzoacridine. In this case, the efficiency of the device is superior to the case where the ring structure including X is condensed at another position. This is because the ring structure containing X is condensed in a bent form in the basic core, and high efficiency can be expected when it is used as an organic material layer in a device such as a light emitting layer, an electron transporting layer, and a hole transporting layer. In addition, the characteristics such as the driving voltage and lifetime of the device can be controlled by suitably controlling the substituents of R1 to R7 and Cy1.
Examples of substituents herein are described below, but are not limited thereto.
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, , Two or more substituents may be the same as or different from each other.
As used herein, the term "substituted or unsubstituted" 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 alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two 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. Means that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent connected thereto. 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,
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
In the present specification, the amide group may be mono- or di-substituted with nitrogen of the amide group with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the general formula of the ester group can be represented by a general formula of -CffOORa, and specifically, it is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 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 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 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 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 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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
In the present specification, when the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.
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,
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.
In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. The amine group may be substituted on the N atom with an aryl group, an alkyl group, an arylalkyl group, and a heterocyclic group. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, A phenol group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, And the like, but the present invention is not limited thereto.
In the present specification, the aryl group in the arylphosphine group, arylamine group, aryloxy group, arylthioxy group, arylsulfoxy group and 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. However, the present invention is 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.
In the present specification, the alkyl group in the alkylamine group, the alkylthio group, and the alkylsulfoxy group is the same as the alkyl group 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.
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 in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, the ring formed by bonding adjacent groups to each other may be monocyclic or polycyclic, and may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and may form a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be selected from the examples of the cycloalkyl group or the aryl group except that the hydrocarbon ring is not the 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 hydrocarbon ring of Cy1 is condensed with the structure of formula (1) and may be monocyclic or polycyclic, and may be aliphatic or aromatic. Also, examples of the above-mentioned aryl group or cycloalkyl group can be selected except for the non-monocyclic group.
In the present specification, the heterocycle of Cy1 means that at least one carbon atom in the hydrocarbon ring is substituted with an atom such as N, O, S or the like which is a hetero atom, which may be monocyclic or polycyclic, and may be aliphatic or aromatic Lt; / RTI > may be selected from the examples of the above-mentioned heterocyclic rings, except that the heterocyclic ring is not a 1-position.
In one embodiment of the present disclosure, Cy1 is a substituted or unsubstituted hydrocarbon ring.
In one embodiment of the present specification, Cy1 is a substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Or a substituted or unsubstituted phenanthrene ring.
In one embodiment of the present invention, the heterocyclic compound represented by the formula (1) may be represented by any one of the following formulas (2) to (6).
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
In formulas (2) to (6)
X,
R8 to R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two adjacent substituents are bonded to each other to form a hydrocarbon ring or a heterocyclic ring.
In one embodiment of the present disclosure, R, R 'and R1 to R7 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
In another embodiment of the disclosure, R, R 'and
The aralamine group, the aryl group, the heterocyclic group may be deuterium; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted heterocyclic group.
In another embodiment, R, R 'and
In one embodiment of the present disclosure, R, R 'and R1 to R7 are the same or different from each other, and each independently hydrogen; Or a substituent group of the following [A-1] group.
[A-1]
In one embodiment of the present disclosure, R, R 'and R1 to R7 are the same or different from each other, and each independently hydrogen; Or a substituent group of the following [A-2] group.
[A-2]
In one embodiment of the present disclosure, R, R 'and R1 to R7 are the same or different from each other, and each independently hydrogen; Or a substituent group of the following [A-3] group.
[A-3]
In one embodiment of the present disclosure, R, R 'and R1 to R7 are the same or different from each other, and each independently hydrogen; Or a substituent group of the following [A-4] group.
[A-4]
In one embodiment of the present disclosure, R, R 'and R1 to R7 are the same or different from each other, and each independently hydrogen; Or a substituent group of the following [A-5] group.
[A-5]
In one embodiment of the present specification,
In another embodiment, R is any one of the substituents of the groups [A-1] to [A-5].
In another embodiment, at least one of R, R 'and
In one embodiment of the present specification,
In one embodiment of the present specification,
In another embodiment, R < 1 > is a substituted or unsubstituted phenyl group.
In one embodiment, R < 1 > is a phenyl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a phenyl group substituted with a phenyl group.
In another embodiment, R < 1 > is a phenyl group substituted with a phenyl group substituted with deuterium.
In another embodiment, R < 1 > is a phenyl group substituted with a biphenyl group.
In another embodiment, R < 1 > is a phenyl group substituted with a naphthyl group.
In another embodiment, R < 1 > is a phenyl group substituted with a terphenyl group.
In another embodiment, R < 1 > is a phenyl group substituted with a phenanthrenyl group.
In another embodiment, R < 1 > is a phenyl group substituted with a triphenylene group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a phenyl group substituted with a nitrogen-containing heterocyclic group.
In another embodiment, R < 1 > is a phenyl group substituted with a nitrogen-containing heterocyclic group substituted or unsubstituted with an aryl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a phenyl group substituted with a carbazole group substituted with a phenyl group.
In another embodiment, R < 1 > is a phenyl group substituted with a benzocarbazole group.
In another embodiment, R < 1 > is a phenyl group substituted with a carbazole group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a phenyl group substituted with a quinoline group.
In one embodiment of the present specification,
In one embodiment of the present invention,
In another embodiment of the present specification,
In one embodiment of the present specification,
In another embodiment, R < 1 > is a phenyl group substituted with an amine group substituted with a phenyl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a phenyl group substituted with an amine group substituted with a phenyl group and a biphenyl group.
In one embodiment of the present invention,
In one embodiment, R < 1 > is a biphenyl group.
In another embodiment, R < 1 > is a biphenyl group substituted with an arylamine group.
In another embodiment, R < 1 > is a biphenyl group substituted with an amine group substituted with a phenyl group.
In one embodiment of the present invention,
In another embodiment, R < 1 > is a biphenyl group substituted with an amine group substituted with a phenyl group and a biphenyl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a biphenyl group substituted with a nitrogen-containing heterocyclic group.
In another embodiment, R < 1 > is a biphenyl group substituted with a carbazole group.
In one embodiment of the present specification, R < 1 > is a biphenyl group substituted with deuterium.
In one embodiment of the present invention,
In one embodiment, R1 is a terphenyl group.
In one embodiment of the present invention,
In another embodiment, R < 1 > is a quarter-phenyl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a naphthyl group substituted with an aryl group.
In one embodiment of the present invention,
In another embodiment, R < 1 > is a naphthyl group substituted with a naphthyl group.
In one embodiment of the present specification,
In another embodiment, R1 is a triphenylene group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is an anthracenyl group substituted with an aryl group.
In one embodiment of the present disclosure,
In another embodiment, R < 1 > is an anthracenyl group substituted with a biphenyl group.
In one embodiment of the present specification,
In one embodiment, R < 1 > is a fluorenyl group substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification,
In one embodiment of the present invention,
In another embodiment, R < 1 > is a phenanthrenyl group.
In one embodiment of the present invention,
In one embodiment, R < 1 > is a substituted or unsubstituted nitrogen-containing heterocyclic group.
In another embodiment, R < 1 > is a substituted or unsubstituted pyridine group.
In another embodiment, R < 1 > is a pyridine group.
In one embodiment, R < 1 > is a pyridine group substituted or unsubstituted with an aryl group.
In one embodiment of the present specification,
In one embodiment of the present specification,
In one embodiment, R < 1 > is a pyrimidine group substituted with an aryl group.
In one embodiment, R < 1 > is a pyrimidine group substituted with a phenyl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a triazine group substituted with an aryl group.
In one embodiment of the present specification,
In one embodiment of the present specification,
In one embodiment, R < 1 > is a carbazol group substituted with an aryl group.
In yet another embodiment, R < 1 > is a carbazole group substituted with a phenyl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a benzoimidazoquinazoline group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a benzoimidazobenzophenanthridine group.
In another embodiment, R < 1 > is a substituted or unsubstituted benzoimidazophenanthridine group.
In another embodiment, R < 1 > is a benzoimidazophenanthridine group.
In another embodiment, R < 1 > is a substituted or unsubstituted quinoline group.
In another embodiment, R < 1 > is a quinolinyl group substituted with an aryl group.
In one embodiment of the present specification,
In another embodiment, R < 1 > is a quinolinyl group substituted with a biphenyl group.
In another embodiment of the present specification, R < 1 > is a substituted or unsubstituted fused heterocyclic ring.
In another embodiment, R < 1 > is a substituted or unsubstituted quinazoline group.
In another embodiment, R < 1 > is a quinazoline group substituted with an aryl group.
In one embodiment of the present specification,
In another embodiment of the present specification,
In another embodiment, R < 1 > is a substituted or unsubstituted dibenzothiophene group.
In another embodiment, R < 1 > is a dibenzothiophene group.
In one embodiment of the present specification, R < 1 > is a substituted or unsubstituted oxygen-containing heterocyclic ring.
In another embodiment, R < 1 > is substituted or unsubstituted dibenzofuran.
In another embodiment, R < 1 > is dibenzofuran.
In one embodiment of the present disclosure, X is S.
In another embodiment, X is O.
In another embodiment of the present disclosure, X is SO 2.
In another embodiment, X is NR.
In one embodiment of the present disclosure, R is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R is a substituted or unsubstituted aryl group.
In another embodiment, R is a substituted or unsubstituted phenyl group.
In one embodiment, R is a phenyl group.
In one embodiment of the present specification, R is a phenyl group substituted with an aryl group.
In another embodiment, R is a phenyl group substituted with a phenyl group.
In another embodiment, R is a phenyl group substituted with a phenyl group substituted with deuterium.
In another embodiment, R is a phenyl group substituted with a biphenyl group.
In another embodiment, R is a phenyl group substituted with a naphthyl group.
In another embodiment, R is a phenyl group substituted with a terphenyl group.
In another embodiment, R is a phenyl group substituted with a phenanthrenyl group.
In another embodiment, R is a phenyl group substituted with a triphenylene group.
In one embodiment of the present specification, R is a phenyl group substituted by a substituted or unsubstituted heterocyclic group.
In another embodiment, R is a phenyl group substituted with a nitrogen-containing heterocyclic group.
In another embodiment, R is a phenyl group substituted with a nitrogen-containing heterocyclic group substituted or unsubstituted with an aryl group.
In one embodiment of the present invention, R is a phenyl group substituted with a carbazole group substituted or unsubstituted with an aryl group.
In another embodiment, R is a phenyl group substituted with a carbazole group substituted with a phenyl group.
In another embodiment, R is a phenyl group substituted with a benzocarbazole group.
In another embodiment, R is a phenyl group substituted with a carbazole group.
In one embodiment of the present specification, R is a phenyl group substituted with a benzoimidazoquinazoline group.
In another embodiment, R is a phenyl group substituted with a quinoline group.
In one embodiment of the present specification, R is a phenyl group substituted with a triazine group substituted or unsubstituted with an aryl group.
In one embodiment of the present invention, R is a phenyl group substituted with a triazine group substituted or unsubstituted with a phenyl group.
In another embodiment of the present specification, R is a phenyl group substituted with a nitrile group.
In one embodiment of the present specification, R is a phenyl group substituted with an arylamine group.
In another embodiment, R is a phenyl group substituted with an amine group substituted with a phenyl group.
In one embodiment of the present specification, R is a phenyl group substituted with an amine group substituted with a biphenyl group.
In another embodiment, R is a phenyl group substituted with an amine group substituted with a phenyl group and a biphenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted biphenyl group.
In one embodiment, R is a biphenyl group.
In another embodiment, R is a biphenyl group substituted with an arylamine group.
In another embodiment, R is a biphenyl group substituted with an amine group substituted with a phenyl group.
In one embodiment of the present specification, R is a biphenyl group substituted with an amine group substituted with a biphenyl group.
In another embodiment, R is a biphenyl group substituted with an amine group substituted with a phenyl group and a biphenyl group.
In one embodiment of the present specification, R is a biphenyl group substituted with a substituted or unsubstituted heterocyclic group.
In another embodiment, R is a biphenyl group substituted with a nitrogen-containing heterocyclic group.
In another embodiment, R is a biphenyl group substituted with a carbazole group.
In one embodiment of the present specification, R is a biphenyl group substituted with deuterium.
In one embodiment of the present specification, R is a substituted or unsubstituted terphenyl group.
In one embodiment, R is a terphenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted quaterphenyl group.
In another embodiment, R is a quaterphenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted naphthyl group.
In another embodiment, R is a naphthyl group substituted with an aryl group.
In one embodiment of the present invention, R is a naphthyl group substituted with a phenyl group.
In another embodiment, R is a naphthyl group substituted with a naphthyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted triphenylene group.
In another embodiment, R is a triphenylene group.
In one embodiment of the present disclosure, R is a substituted or unsubstituted anthracenyl group.
In another embodiment, R is an anthracenyl group substituted with an aryl group.
In one embodiment of the present specification, R is an anthracenyl group substituted with a phenyl group.
In another embodiment, R is an anthracenyl group substituted with a biphenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted fluorenyl group.
In one embodiment, R is a fluorenyl group substituted or unsubstituted with an alkyl group.
In one embodiment of the present specification, R is a fluorenyl group substituted or unsubstituted with a methyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted phenanthrenyl group.
In another embodiment, R is a phenanthrenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted heterocyclic group.
In one embodiment, R is a substituted or unsubstituted nitrogen-containing heterocyclic group.
In another embodiment, R is a substituted or unsubstituted pyridine group.
In another embodiment, R is a pyridine group.
In one embodiment, R is a pyridine group substituted or unsubstituted with an aryl group.
In one embodiment of the present specification, R is a pyridine group substituted with a phenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted pyrimidine group.
In one embodiment, R is a pyrimidine group substituted with an aryl group.
In one embodiment, R is a pyrimidine group substituted with a phenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted triazine group.
In another embodiment, R is a triazine group substituted with an aryl group.
In one embodiment of the present specification, R is a triazine group substituted with a phenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted carbazole group.
In one embodiment, R is a carbazole group substituted with an aryl group.
In another embodiment, R is a carbazolyl group substituted with a phenyl group.
In one embodiment of the present specification, R is a substituted or unsubstituted benzoimidazoquinazoline group.
In another embodiment, R is a benzoimidazoquinazoline group.
In one embodiment of the present specification, R is a substituted or unsubstituted benzoimidazobenzophenanthridine group.
In another embodiment, R is a benzoimidazobenzophenanthridine group.
In another embodiment, R is a substituted or unsubstituted benzoimidazophenanthridine group.
In another embodiment, R is a benzoimidazophenanthridine group.
In another embodiment, R is a substituted or unsubstituted quinoline group.
In another embodiment, R is a quinolinyl group substituted with an aryl group.
In one embodiment of the present disclosure, R is a quinolinyl group substituted with a phenyl group.
In another embodiment, R is a quinolinyl group substituted with a biphenyl group.
In another embodiment of the present specification, R is a substituted or unsubstituted heteroaromatic ring.
In another embodiment, R is a substituted or unsubstituted quinazoline group.
In another embodiment, R is a quinazoline group substituted with an aryl group.
In one embodiment of the present specification, R is a quinazoline group substituted with a phenyl group.
In another embodiment of the present disclosure, R is a quinazoline group substituted with a biphenyl group.
In another embodiment, R is a substituted or unsubstituted dibenzothiophene group.
In another embodiment, R is a dibenzothiophene group.
In one embodiment of the present specification, R is a substituted or unsubstituted oxygen-containing heterocycle.
In another embodiment, R is substituted or unsubstituted dibenzofuran.
In another embodiment, R is dibenzofuran.
In one embodiment of the present disclosure,
In another embodiment, R3 is hydrogen.
In one embodiment of the present disclosure, R4 is hydrogen.
In one embodiment of the present disclosure, R5 is hydrogen.
In one embodiment of the present disclosure, R6 is hydrogen.
In one embodiment of the present specification, R7 is hydrogen.
In one embodiment of the present disclosure, Cy1 is an unsubstituted hydrocarbon ring.
In one embodiment of the present disclosure, Cy1 is a benzene ring; Naphthalene ring; Or a phenanthrene ring.
In one embodiment of the present specification, R8 to R37 are hydrogen.
In one embodiment of the present invention, the heterocyclic compound represented by
'
In one embodiment of the present invention, the heterocyclic compound represented by
In one embodiment of the present invention, the heterocyclic compound represented by
In another embodiment of the present disclosure, the heterocyclic compound represented by
In one embodiment of the present invention, the heterocyclic compound represented by
The heterocyclic compound represented by
Bromine is substituted with a dioxaborolane group in the formula (A) containing brominated Cy1 and X, and then 1-chloro-8-nitronaphthalene substituted with R2 to R7 is reacted to prepare the formula (C).
The compound of formula (1) can be prepared by reacting the compound of formula (C) through a ring-closing reaction to form a compound of formula (D) and then reacting with a halogen-substituted R1.
In the above process, X, Cy1 and R1 to R7 may be adjusted to produce the heterocyclic compound represented by the general formulas (2) to (6) as well as the heterocyclic compound represented by the general formula (1) The substituent may be introduced or the ring-closing reaction may be carried out under any reaction condition known in the art.
Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound described above.
Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.
When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.
The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
In another embodiment, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host of the light emitting layer.
In one embodiment of the present invention, the organic material layer includes an electron transport layer, an electron injection layer or an electron blocking layer, and the electron transport layer, electron injection layer or electron blocking layer includes the heterocyclic compound.
In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.
In one embodiment of the present invention, the organic material layer further includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic compound layer including the heterocyclic compound.
In one embodiment of the present invention, the organic compound layer containing the heterocyclic compound includes the heterocyclic compound as a host and includes another organic compound, metal or metal compound as a dopant.
In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic compound layers, and a cathode are sequentially stacked on a substrate.
In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.
For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.
1 illustrates a structure of an organic electronic device in which a
2 shows an organic electronic device in which a
In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.
The organic light-emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the heterocyclic compound.
When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the heterocyclic compound, i.e., the compound represented by
For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode 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 then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, the compound of
In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.
In one embodiment of the present disclosure, the first electrode is an anode and the second electrode is a cathode.
In another embodiment, the first electrode is a cathode and the second electrode is an anode.
As the anode material, a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth. Specific examples of the anode 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 cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
The hole injecting material is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, a hole injecting effect for the anode, an excellent hole injecting effect for a light emitting layer or a light emitting material, A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer as the hole transport material. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.
The electron transporting material is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the electron injecting layer to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer for injecting electrons from the electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on 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, perylene tetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
The electron blocking layer is made of a material having a function of transporting holes and capable of transporting electrons with a remarkably small capacity to transport electrons. By blocking electrons while transporting holes, the probability of recombination of electrons and holes can be improved. A known electron blocking material can be used for the electron blocking layer.
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 hole blocking layer is a layer which prevents the cathode from reaching the hole, and can be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
In one embodiment of the present invention, the heterocyclic compound may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.
< Synthetic example 1>
< Manufacturing example 1>
Synthesis of Compound 2-2-49
[Compound 2-2-49]
To a 500 ml round bottom flask in a nitrogen atmosphere was added compound 2-1 (10.00, 32.57 mmol), N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) biphenyl] -4-amine (16.25 g, 34.20 mmol) was completely dissolved in 180 ml of xylene, sodium tert-butoxide (4.07 g, 42.35 mol) was added, and bis (tri- tert- butylphosphine) palladium , 0.31 mmol), and the mixture was heated with stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (180 ml) to obtain the above compound 2-2-49 (16.64 g, yield: 73%).
MS [M + H] < + > = 703
< Manufacturing example 2>
Synthesis of the following compound 2-1-50
[Compound 2-1-50]
N- (4-bromophenyl) -N-phenyl- [1,1'-biphenyl] -4-amine (13.00 g, 32.51 mmol) was added to a 500 ml round bottom flask in a nitrogen atmosphere. was stirred and then completely dissolved in Xylene 160ml was added sodium tert-butoxide (3.87g, 40.25mol ) , and heated and then put Bis (tri- tert -butylphosphine) palladium ( 0) (0.16g, 0.31mmol) for 4 hours . The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (150 ml) to obtain the compound 2-1-50 (15.43 g, yield: 78%).
MS [M + H] < + > = 643
< Manufacturing example 3>
Synthesis of the following compounds 2-3-36
[Compound 2-3-36]
To a 500 ml round-bottomed flask under nitrogen, compound 2-3 (16.71, 43.75 mmol) and 2-chloro-4-phenylquinazoline (10.00 g, 41.67 mmol) were completely dissolved in 160 ml of xylene and sodium tert-butoxide (5.21 g, 54.17 mol ) Was added, and bis (tri- tert- butylphosphine) palladium (0) (0.21 g, 0.42 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (150 ml) to obtain the compound 2-3-36 (21.11 g, yield: 86%).
MS [M + H] < + > = 587
< Manufacturing example 4>
Synthesis of Compound 3-1-39
[Compound 3-1-39]
(8.46, 22.68 mmol), 2 - ([1,1'-biphenyl] -4-yl) -4- (4-bromophenyl) -6- 3,5-triazine (10.00g, 21.60mmol), and then completely dissolved in Xylene 230ml was added sodium tert-butoxide (2.70g, 28.08mol ) and, Bis (tri- tert -butylphosphine) palladium (0) (0.11g, 0.22 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (210 ml) to obtain the above compound 3-1-39 (21.11 g, yield: 86%).
MS [M + H] < + > = 757
< Manufacturing example 5>
Synthesis of Compound 3-2-8
[Compound 3-2-8]
(11.86, 33.23 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (10.00 g, 31.65 mmol) were dissolved in 210 ml of xylene in a 500 ml round- After complete dissolution, sodium tert-butoxide (3.95 g, 41.14 mol) was added and bis (tri- tert- butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added and the mixture was heated with stirring for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to obtain the above compound 3-2-8 (14.42 g, yield: 71%).
MS [M + H] < + > = 638
< Manufacturing example 6>
Synthesis of the following compound 5-1-45
[Compound 5-1-45]
(9.42, 26.38 mmol), 9- (4'-bromo- [1,1'-biphenyl] -4-yl) -9H-carbazole (10.00 g, 25.13 mmol) in a 500 ml round- ) Xylene after the completely dissolved in 180ml sodium tert-butoxide (3.14g, 32.66mol) was added and, Bis (tri- tert -butylphosphine) palladium (0) (0.13g, 0.25mmol) with heating and stirring for 5 hours was placed Respectively. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (220 ml) to obtain the above compound 5-1-45 (15.09 g, yield: 87%).
MS [M + H] < + > = 691
< Manufacturing example 7>
Synthesis of Compound 5-2-32
[Compound 5-2-32]
(9.37, 26.25 mmol) and 4'-bromo-N, N-diphenyl- [1,1'-biphenyl] -4-amine (10.00 g, 25.00 mmol) in a 500 ml round- after completely dissolved in Xylene 160ml was added to the sodium tert-butoxide (3.12g, 32.50mol ) , insert a Bis (tri- tert -butylphosphine) palladium ( 0) (0.13g, 0.25mmol) was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (260 ml) to obtain the above compound 5-2-34 (11.54 g, yield: 68%).
MS [M + H] < + > = 677
≪ Production Example 8 &
Synthesis of the following compound 5-2-39
[Compound 5-2-39]
(8.08, 22.63 mmol), 2 - ([1,1'-biphenyl] -4-yl) -4- (4-bromophenyl) -6- 3,5-triazine (10.00g, 21.55mmol), and then completely dissolved in Xylene 250ml was added sodium tert-butoxide (3.12g, 32.50mol ) and, Bis (tri- tert -butylphosphine) palladium (0) (0.11g, 0.22 mmol) were added thereto, and the mixture was heated and stirred for 7 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 220 ml of tetrahydrofuran to obtain the above compound 5-2-39 (12.26 g, yield: 77%).
MS [M + H] < + > = 741
<Experimental Example 1-1>
The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.
[LINE]
N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.
[NPB]
Subsequently, the following compound 2-2-49 was vacuum deposited on the hole transport layer to a thickness of 100 Å to form an electron blocking layer.
[Compound 2-2-49]
Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.
[BH] [BD]
[ET1] [LiQ]
The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.
Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon
<Experimental Example 1-2>
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 2-1-50 was used in place of Compound 2-2-49 in Experimental Example 1-1.
<Experimental Example 1-3>
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 5-1-45 was used in place of Compound 2-2-49 in Experimental Example 1-1.
<Experimental Example 1-4>
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 5-2-34 was used in place of Compound 2-2-49 in Experimental Example 1-1.
≪ Comparative Example 1 &
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that
[EB 1]
≪ Comparative Example 2 &
An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1 except that
[EB 2]
When currents were applied to the organic light-emitting devices fabricated by Experimental Examples 1-1 to 1-4 and Comparative Examples 1 and 2, the results shown in Table 1 were obtained.
(Electronic blocking layer)
(V @ 10 mA / cm 2 )
(cd / A @ 10mA / cm 2)
(x, y)
As shown in Table 1, the organic EL devices of Experimental Examples 1-1 to 4 using the compound represented by
The compound represented by the formula according to the present invention has excellent electron suppression ability and exhibits characteristics of low voltage and high efficiency and can be applied to organic light emitting devices.
<Experimental Example 2-1>
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 (ndium tin oxide) 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.
(60 nm) / TCTA (80 nm) / Compound 3-1-39 + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).
The structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP are as follows.
[m-MTDATA] [TCTA]
[Ir (ppy) 3] [BCP]
[Compound 3-1-39]
<Experimental Example 2-2>
An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 5-2-39 was used instead of Compound 3-1-39 in Experimental Example 2-1.
≪ Comparative Example 3 &
An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that GH 1 (CBP) was used instead of Compound 3-1-39 in Experimental Example 2-1.
[GH 1]
≪ Comparative Example 4 &
An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that
[GH 2]
The results shown in Table 2 were obtained when current was applied to the organic light-emitting devices manufactured by Experimental Examples 2-1 and 2-2 and Comparative Examples 3 and 4.
(Host)
(V @ 10 mA / cm 2 )
(cd / A @ 10mA / cm 2)
(nm)
As a result of the experiment, the green organic EL devices of Experimental Examples 2 to 1 and 4 using the compound represented by
<Experimental Example 3-1>
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 × 10 -6 torr, and an organic material was formed on the ITO in this order by DNTPD (700 Å), α-NPB (300 Å) The compound 2-3-36 was used as a host (90 wt%). Alq3 (350 Å), LiF (5 Å), and Al (1,000 Å) were deposited in the order of doping, as follows: 0.4 mPa .
The structures of DNTPD, alpha -NPB, (piq) 2Ir (acac) and Alq3 are as follows.
[DNTPD] [[alpha] -NPB]
[(Piq) 2Ir (acac)] [Alq3]
<Experimental Example 3-2>
An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that Compound 3-2-8 was used instead of Compound 2-3-36 in Experimental Example 3-1.
≪ Comparative Example 5 &
An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1 except that Compound RH 1 (CBP) shown below was used instead of Compound 2-3-36 in Experimental Example 3-1.
[RH 1]
≪ Comparative Example 6 >
An organic light emitting device was fabricated in the same manner as in Experimental Example 3-1, except that the following
[RH 2]
The voltage, the current density, the luminance, the color coordinate, and the life span of the organic electroluminescent device manufactured according to the following Experimental Examples 3-1 and 3-2 and Comparative Examples 5 and 6 were measured and the results are shown in Table 3 below . T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.
(V)
(cd / m < 2 &
(x, y)
(hr)
As a result of the experiment, the red organic EL devices of Experimental Examples 3-1 and 3-2 using the compound according to the present invention as a host material of the light emitting layer had a core structure similar to that of Comparative Example 5 using conventional CBP and
Although the preferred embodiments of the present invention (electron blocking layer, green luminescent layer, and red luminescent layer) have been described above, the present invention is not limited thereto and various modifications and variations may be made within the scope of the claims and the detailed description of the invention. It is also within the scope of the invention.
1: substrate
2: anode
3: light emitting layer
4: Cathode
5: Hole injection layer
6: hole transport layer
7: Electron transport layer
Claims (15)
[Chemical Formula 1]
In formula (1)
Cy1 is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle,
X is CRR ';NR;O;S;SO; SO 2 ; Or SiRR '
R, R 'and R1 to R7 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; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two adjacent substituents are bonded to each other to form a hydrocarbon ring or a heterocyclic ring.
Cy1 is a substituted or unsubstituted benzene ring; A substituted or unsubstituted naphthalene ring; Or a substituted or unsubstituted phenanthrene ring.
The heterocyclic compound represented by the formula (1) is represented by any one of the following formulas (2) to (6):
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
In formulas (2) to (6)
X, R 1 to R 7 are the same as defined in formula (1)
R8 to R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or two adjacent substituents are bonded to each other to form a hydrocarbon ring or a heterocyclic ring.
R, R 'and R1 to R7 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
At least one of R, R 'and R 1 to R 7 is selected from the group consisting of deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group An arylamine group substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, Substituted or unsubstituted alkyl group, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, which is substituted or unsubstituted or substituted with one or two or more substituents selected from the group consisting of hydrogen, An unsubstituted aryl group; Or substituted with one or two or more substituents selected from the group consisting of a hydrogen atom, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Or an unsubstituted heterocyclic group.
The heterocyclic compound represented by Formula 2 is represented by the following Formulas 2-1-1 to 2-1-60, 2-2-1 to 2-2-60, 2-3-1 to 2-3-64, and 2- 4-1 to 2-4-3.
'
.
The heterocyclic compound represented by Formula 3 may be represented by the following Formulas 3-1-1 to 3-1-45, 3-2-1 to 3-2-45, 3-3-1 to 3-3-77, 3- 4-1 and 3-5-1 to 3-5-3.
.
The heterocyclic compound represented by the general formula (4) is represented by the following general formulas (4-1-1, 4-2-1, 4-3-1 to 4-3-14, 4-4-1 and 4-5-1 to 4- A heterocyclic compound represented by any one of < RTI ID = 0.0 > 5-3 < / RTI &
The heterocyclic compound represented by Formula 5 is represented by the following Formulas 5-1-1 to 5-1-45, 5-2-1 to 5-2-45, 5-3-1 to 5-3-78, 5- 4-1 and 5-5-1 to 5-5-3.
The heterocyclic compound represented by Formula 6 may be any one of the following Formulas 6-1-1 to 6-1-44, 6-2-1 to 6-2-44, and 6-3-1 to 6-3-64 Heterocyclic compounds that are displayed:
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the heterocyclic compound.
Wherein the organic material layer includes an electron transport layer, an electron injection layer or an electron blocking layer,
Wherein the electron transport layer, the electron injection layer, or the electron blocking layer comprises the heterocyclic compound.
Wherein the organic material layer includes a hole transporting layer or a hole injecting layer,
Wherein the hole transport layer or the hole injection layer comprises the heterocyclic compound.
The organic light emitting device includes a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140167847 | 2014-11-27 | ||
| KR20140167847 | 2014-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160064029A true KR20160064029A (en) | 2016-06-07 |
| KR101844639B1 KR101844639B1 (en) | 2018-04-03 |
Family
ID=56193036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020150167403A KR101844639B1 (en) | 2014-11-27 | 2015-11-27 | Hetero-cyclic compound and organic light emitting device comprising the same |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR101844639B1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180133702A (en) * | 2017-06-07 | 2018-12-17 | 주식회사 엘지화학 | Polymer and organic electronic device comprising the same |
| WO2019203613A1 (en) * | 2018-04-19 | 2019-10-24 | 주식회사 엘지화학 | Compound and organic light emitting diode comprising same |
| US10964894B2 (en) | 2017-01-25 | 2021-03-30 | Merck Patent Gmbh | Carbazole derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100023783A (en) | 2008-08-22 | 2010-03-04 | 주식회사 엘지화학 | Organic electronic device material and organic electronic device using the same |
-
2015
- 2015-11-27 KR KR1020150167403A patent/KR101844639B1/en active IP Right Grant
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100023783A (en) | 2008-08-22 | 2010-03-04 | 주식회사 엘지화학 | Organic electronic device material and organic electronic device using the same |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10964894B2 (en) | 2017-01-25 | 2021-03-30 | Merck Patent Gmbh | Carbazole derivatives |
| KR20180133702A (en) * | 2017-06-07 | 2018-12-17 | 주식회사 엘지화학 | Polymer and organic electronic device comprising the same |
| WO2019203613A1 (en) * | 2018-04-19 | 2019-10-24 | 주식회사 엘지화학 | Compound and organic light emitting diode comprising same |
| KR20190122172A (en) * | 2018-04-19 | 2019-10-29 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| CN111868048A (en) * | 2018-04-19 | 2020-10-30 | 株式会社Lg化学 | Compound and organic light emitting device including the same |
| CN111868048B (en) * | 2018-04-19 | 2023-05-19 | 株式会社Lg化学 | Compound and organic light emitting device comprising the same |
| US11812658B2 (en) | 2018-04-19 | 2023-11-07 | Lg Chem, Ltd. | Compound and organic light emitting diode comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101844639B1 (en) | 2018-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101913926B1 (en) | Heterocyclic compound and organic light emitting device using the same | |
| KR102116161B1 (en) | Nitrogen-containing compound and organic electronic device using the same | |
| KR101784562B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR101888252B1 (en) | Compound having spiro structure and organic light emitting device comprising the same | |
| KR101773670B1 (en) | Fused cyclic compound including nitrogen and organic light emitting device using the same | |
| KR102003375B1 (en) | Fused cyclic compound and organic light emitting device using the same | |
| KR101644700B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR101793784B1 (en) | Heterocyclic compound including nitrogen and organic light emitting device using the same | |
| KR101849872B1 (en) | Spiro compound and organic electronic device comprising the same | |
| KR101905970B1 (en) | Compound and organic electronic device comprising the same | |
| KR101928935B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR101916572B1 (en) | Compound and organic light electronic device comprising the same | |
| KR101844672B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR20170100452A (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR20170049398A (en) | Cyclic compound and organic light emitting device comprising the same | |
| KR20160051584A (en) | Cyclic compound and organic light emitting device comprising the same | |
| KR101928934B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR101844639B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR20160111345A (en) | Fused cyclic compound including nitrogen and organic light emitting device using the same | |
| KR101726953B1 (en) | Compound and organic light emitting device comprising the same | |
| KR101964607B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR101835210B1 (en) | Compound and organic electronic device using the same | |
| KR101941148B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same | |
| KR101755839B1 (en) | Spiro structure compound and organic light emitting device comprising the same | |
| KR101945347B1 (en) | Hetero-cyclic compound and organic light emitting device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E90F | Notification of reason for final refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant |