CN113015728B - Compound and organic light emitting device using the same - Google Patents

Compound and organic light emitting device using the same Download PDF

Info

Publication number
CN113015728B
CN113015728B CN202080006146.0A CN202080006146A CN113015728B CN 113015728 B CN113015728 B CN 113015728B CN 202080006146 A CN202080006146 A CN 202080006146A CN 113015728 B CN113015728 B CN 113015728B
Authority
CN
China
Prior art keywords
compound
mmol
group
layer
substituted
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CN202080006146.0A
Other languages
Chinese (zh)
Other versions
CN113015728A (en
Inventor
金永锡
金旼俊
李东勋
吴重锡
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
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 LG Chem Ltd filed Critical LG Chem Ltd
Publication of CN113015728A publication Critical patent/CN113015728A/en
Application granted granted Critical
Publication of CN113015728B publication Critical patent/CN113015728B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention provides a novel compound and an organic light emitting device using the same.

Description

Compound and organic light emitting device using the same
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2019-0066108, 6.4.2019, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
[ Prior Art literature ]
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
x are each independently N or CH, but more than 2 of X are N,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 1 to R 4 Are hydrogen or deuterium; or R is 1 To R 4 Two adjacent ones of the two groups are combined to form a benzene ring, and the rest is hydrogen or deuterium,
R 5 is hydrogen or deuterium, and is preferably selected from the group consisting of,
R 6 each independently of the other is hydrogen or deuterium,
n is an integer from 1 to 3.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, low driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, electron suppression, luminescence, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole suppression layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the present description of the invention,represents a bond to other substituents.
In the present specification, "substituted or unsubstitutedThe term substituted "means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group [ ] an alkyl thio xy group); arylthio (/ -> aryl thio xy); alkylsulfonyl (+)>an alkyl sulfoxy); arylsulfonyl (+)>aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in a heterocyclic group comprising 1 or more of S atoms, or a substituent which is bonded to 2 or more substituents in the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and the like,Terphenyl, and the like, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, fluorenyl groups may be substituted, and 2 substituents may be
Etc. However, the present invention is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as exemplified for the aryl group described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above alkyl group. In the present specification, the heteroaryl group in the heteroarylamine group may be applied to the above description about the heterocyclic group. In this specification, alkenyl groups in aralkenyl groups are the same as those exemplified for the alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied thereto. In this specification, the heterocyclic ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the heterocyclic group can be applied thereto.
In the above chemical formula 1, preferably, X is N.
Preferably Ar 1 And Ar is a group 2 Each independently is a substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-20 Heteroaryl groups.
More preferably Ar 1 And Ar is a group 2 Each independently is unsubstituted phenyl, phenyl substituted with 5 deuterium, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothienyl, carbazolyl, or 9-phenylcarbazolyl.
Preferably, R 5 Is hydrogen.
Preferably, R 6 Is hydrogen.
On the other hand, R 1 To R 4 Wherein adjacent two of them combine to form a benzene ring, and the remainder being hydrogen or deuterium is specifically R 1 And R is 2 Binding to, or R 2 And R is 3 Binding to, or R 3 And R is 4 And combine to form a benzene ring. As an example, R 1 And R is 2 When bonded to form a benzene ring, the chemical formula 1 is represented by the following chemical formula 1-1.
[ chemical formula 1-1]
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
the present invention also provides a method for producing a compound represented by the above chemical formula 1, as shown in the following reaction formula 1.
[ reaction type 1]
In the above reaction scheme, X, ar 1 、Ar 2 、R 1 To R 6 And n is as defined in chemical formula 1, X 'is halogen, preferably X' is chlorine or bromine.
The amine substitution reaction of the above reaction formula 1 is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction can be modified according to a technique known in the art. The above-described production method may be more specifically described in the synthesis examples described below.
In another aspect, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic 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 layer may include a light-emitting layer including the compound represented by chemical formula 1. In particular, the compounds according to the invention can be used as hosts for light-emitting layers.
The organic layer may include a hole injection layer, a hole transport layer, or an electron suppression layer, and the hole injection layer, the hole transport layer, or the electron suppression layer may include a compound represented by chemical formula 1.
The electron transport layer, the electron injection layer, or the layer in which both electron transport and electron injection are performed contains the compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above organic layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole suppression layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole suppression layer, electron transport layer, and electron injection layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, in the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, it is usual to make the air be leftThe holes can be smoothly implanted into the organic layer, and preferably, the holes are large in work function. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic 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, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene; rubrene, etc., but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds Pyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Diindenopyrene and the like, and styrylamine compounds are compounds in which at least 1 aryl vinyl group is substituted on a substituted or unsubstituted aryl amine, and are selected from aryl groups, silyl groups1 or more substituents in the alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and as an electron transporting substance, a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer is suitable for a substance having a large mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to an organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Synthesis example
Synthesis example 1
Substance (sub) 1 (10 g,20.7 mmol), compound B (6.1 g,22.7 mmol), sodium tert-butoxide (4 g,41.3 mmol) were added to 200ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-tert-butylphosphine) palladium (0) (bis (tris-tert-butylphosphine) palladium (0)) (0.2 g,0.4 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.7g of compound 1 was obtained. (yield 52%, MS: [ M+H) ] + ＝715)。
Synthesis example 2
Substance 2 (10 g,17.9 mmol), compound B (5.3 g,19.6 mmol), sodium tert-butoxide (3.4 g,35.7 mmol) were added to 200ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.4 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.6g of compound 2 was obtained. (yield 61%, MS: [ M+H)] + ＝791)。
Synthesis example 3
Material 3 (10 g,16.9 mmol), compound A (4.1 g,18.6 mmol), sodium t-butoxide (3.3 g,33.9 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.7g of compound 3 was obtained. (yield 67%, MS: [ M+H) ] + ＝771)。
Synthesis example 4
Substance 4 (10 g,15.8 mmol), compound C (4.6 g,17.3 mmol), sodium tert-butoxide (3 g,31.5 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tertiary)Butylphosphine) palladium (0) (0.2 g,0.3 mmol). After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8g of compound 4 was obtained. (yield 59%, MS: [ M+H)] + ＝865)。
Synthesis example 5
Substance 5 (10 g,15.6 mmol), compound B (4.6 g,17.2 mmol), sodium tert-butoxide (3 g,31.2 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.7g of compound 5 was obtained. (yield 64%, MS: [ M+H) ] + ＝871)。
Synthesis example 6
Substance 6 (10 g,14.3 mmol), compound A (3.4 g,15.7 mmol), sodium tert-butoxide (2.7 g,28.6 mmol) were added to 200ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.1 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.7g of compound 6 was obtained. (yield)69％，MS：[M+H] + ＝880)。
Synthesis example 7
Substance 7 (10 g,15.1 mmol), compound B (4.5 g,16.7 mmol), sodium tert-butoxide (2.9 g,30.3 mmol) were added to 200ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.5g of compound 7 was obtained. (yield 63%, MS: [ M+H) ] + ＝891)。
Synthesis example 8
Material 8 (10 g,15 mmol), compound B (4.4 g,16.5 mmol), sodium tert-butoxide (2.9 g,30 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.3g of compound 8 was obtained. (yield 62%, MS: [ M+H)] + ＝897)。
Synthesis example 9
Substance 9 (10 g,15.4 mm)ol), compound B (4.5 g,16.9 mmol), sodium tert-butoxide (3 g,30.8 mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.3g of compound 9 was obtained. (yield 54%, MS: [ M+H) ] + ＝881)。
Synthesis example 10
Substance 10 (10 g,15 mmol), compound C (4.4 g,16.5 mmol), sodium tert-butoxide (2.9 g,30 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7g of compound 10 was obtained. (yield 52%, MS: [ M+H)] + ＝897)。
Synthesis example 11
Substance 11 (10 g,16.4 mmol), compound D (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, and after washing with water 2 times, the organic layer was separated, and dried over anhydrous magnesium sulfateAfter the treatment, filtration was carried out, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 6.5g of compound 11 was obtained. (yield 55%, MS: [ M+H) ] + ＝725)。
Synthesis example 12
/>
Substance 12 (10 g,16.4 mmol), compound C (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.3g of compound 12 was obtained. (yield 55%, MS: [ M+H)] + ＝815)。
Synthesis example 13
Substance 13 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 6.8g of compound 13 was obtained. (yield 54%, MS: [ M+H) ] + ＝771)。
Synthesis example 14
Substance 14 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.8g of compound 14 was obtained. (yield 60%, MS: [ M+H)] + ＝791)。
Synthesis example 15
Substance 15 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.4g of compound 15 was obtained. (yield 57%, MS: [ M+H) ] + ＝791)。
Synthesis example 16
Substance 16 (10 g,16.4 mmol), compound D (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed and cooledCooling to normal temperature, and removing the solvent under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.5g of compound 16 was obtained. (yield 53%, MS: [ M+H)] + ＝867)。
Synthesis example 17
Substance 17 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.7g of compound 17 was obtained. (yield 52%, MS: [ M+H) ] + ＝906)。
Synthesis example 18
Substance 18 (10 g,16.4 mmol), compound C (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9.1g of compound 18 was obtained. (yield 58%, MS: [ M+H)] + ＝956)。
Synthesis example 19
Substance 19 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.9g of compound 19 was obtained. (yield 61%, MS: [ M+H) ] + ＝891)。
Synthesis example 20
Substance 20 (10 g,16.4 mmol), compound C (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9.1g of compound 20 was obtained. (yield 58%, MS: [ M+H)] + ＝956)。
Synthesis example 21
Under nitrogen atmosphere, substance 21 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2g,32.8 mmol) was added to 200ml of xylene, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 5.9g of compound 21 was obtained. (yield 54%, MS: [ M+H) ] + ＝665)。
Synthesis example 22
Substance 22 (10 g,16.4 mmol), compound C (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.1g of compound 22 was obtained. (yield 57%, MS: [ M+H)] + ＝765)。
Synthesis example 23
Substance 23 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. Will beThe concentrated compound was purified by silica gel column chromatography, whereby 8g of compound 23 was obtained. (yield 60%, MS: [ M+H) ] + ＝815)。
Synthesis example 24
Substance 24 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.5g of compound 24 was obtained. (yield 52%, MS: [ M+H)] + ＝880)。
Synthesis example 25
Substance 25 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9.3g of compound 25 was obtained. (yield 70%, MS: [ M+H) ] + ＝815)。
Synthesis example 26
Substance 26 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.4g of compound 26 was obtained. (yield 52%, MS: [ M+H)] + ＝871)。
Synthesis example 27
Substance 27 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.9g of compound 27 was obtained. (yield 60%, MS: [ M+H) ] + ＝805)。
Synthesis example 28
Substance 28 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression.Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9.9g of compound 28 was obtained. (yield 68%, MS: [ M+H)] + ＝891)。
Synthesis example 29
Substance 29 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8g of compound 29 was obtained. (yield 58%, MS: [ M+H) ] + ＝841)。
Synthesis example 30
Substance 30 (10 g,16.4 mmol), compound D (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 11g of compound 30 was obtained. (yield 70%, MS: [ M+H)] + ＝956)。
Synthesis example 31
Material 31 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.8g of compound 31 was obtained. (yield 67%, MS: [ M+H) ] + ＝715)。
Synthesis example 32
/>
Substance 32 (10 g,16.4 mmol), compound D (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.5g of compound 32 was obtained. (yield 64%, MS: [ M+H)] + ＝815)。
Synthesis example 33
Substance 33 (10 g,16.4 mmol), compound D (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under a nitrogen atmosphereStirring and refluxing. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.2g of compound 33 was obtained. (yield 54%, MS: [ M+H) ] + ＝815)。
Synthesis example 34
Substance 34 (10 g,16.4 mmol), compound D (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9g of compound 34 was obtained. (yield 64%, MS: [ M+H)] + ＝855)。
Synthesis example 35
Substance 35 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. Subjecting the concentrated compound to silica gel column chromatography Purification gave 9g of compound 35. (yield 64%, MS: [ M+H)] + ＝855)。
Synthesis example 36
Substance 36 (10 g,16.4 mmol), compound C (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.1g of compound 36 was obtained. (yield 53%, MS: [ M+H)] + ＝815)。
Synthesis example 37
Material 37 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 7.8g of compound 37 was obtained. (yield 54%, MS: [ M+H) ] + ＝880)。
Synthesis example 38
Material 38 (10 g,16.4 mmol), compound B (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9.4g of compound 38 was obtained. (yield 65%, MS: [ M+H ]] + ＝881)。
Synthesis example 39
Material 39 (10 g,16.4 mmol), compound A (3.9 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and then the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 9g of compound 39 was obtained. (yield 65%, MS: [ M+H ] ] + ＝841)。
Synthesis example 40
/>
Substance 40 (10 g,16.4 mmol), compound D (4.8 g,18 mmol), sodium tert-butoxide (3.2 g,32.8 mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.2 g,0.3 mmol) was charged. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed by decompression. Then, the compound was completely dissolved again in chloroform,after washing with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 8.3g of compound 40 was obtained. (yield 53%, MS: [ M+H)] + ＝956)
Examples (example)
Comparative example 1
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, as a hole injection layer, the following HI-1 compound was usedAnd p-doping of the following a-1 compound was performed at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was subjected to vacuum evaporation to form a film thickness +.>Is provided. Next, on the hole transport layer, the film thickness is +.>An electron-inhibiting layer was formed by vacuum evaporation of the EB-1 compound described below. Next, on the EB-1 vapor deposited film, the following RH-1 compound was appliedAnd the following Dp-39 compound was formed by vacuum evaporation at a weight ratio of 98:2A red light emitting layer of thickness. On the above-mentioned light-emitting layer, the film thickness is +.>The hole-suppressing layer was formed by vacuum evaporation of the HB-1 compound described below. Next, on the hole-suppressing layer, the following ET-1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1, thereby giving ∈1>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintained Lithium fluoride maintenance of cathode/sec->Vapor deposition rate per second, aluminum maintenance->Vapor deposition rate per second, vacuum degree was maintained at 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device. />
Comparative examples 2 to 10
An organic light-emitting device was fabricated in the same manner as in comparative example 1, except that the following compounds RH-2 to RH-10 were used as the main material of the red light-emitting layer, respectively, instead of RH-1.
Examples 1 to 40
An organic light-emitting device was fabricated in the same manner as in comparative example 1, except that the compounds 1 to 40 of the above synthesis examples were used as the main material of the red light-emitting layer instead of RH-1 of comparative example 1.
Experimental example
The organic light emitting devices of the above comparative examples 1 to 10 and examples 1 to 40 were heat-treated by being stored in an oven at 110 ℃ for 30 minutes, and then a driving voltage, current efficiency and lifetime (T95) were measured by applying a current thereto, and the results are shown in table 1 below. At this time, the voltage and the efficiency were such that 10mA/cm was applied 2 Is measured by the current density of the sample. T95 in Table 1 below means that the current density was 10mA/cm 2 Time measured when the initial brightness was reduced to 95%.
TABLE 1
/>
Referring to table 1 above, it was confirmed that the organic light emitting device using the compound of chemical formula 1 of the present invention as a host material of the red light emitting layer exhibited low driving voltage, and excellent current efficiency and lifetime characteristics.
Symbol description
1: substrate 2: anode
3: organic layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: light-emitting layer
9: hole-inhibiting layer 10: electron transport layer
11: an electron injection layer.

Claims (8)

1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
x are each independently N or CH, but more than 2 of X are N,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 1 to R 4 Are hydrogen or deuterium; or R is 1 To R 4 Two adjacent ones of the two groups are combined to form a benzene ring, and the rest is hydrogen or deuterium,
R 5 is hydrogen or deuterium, and is preferably selected from the group consisting of,
R 6 each independently of the other is hydrogen or deuterium,
n is an integer of 1 to 3,
wherein the "substituted or unsubstituted" means substituted with a substituent selected from deuterium or C 6-60 More than 1 substituent in the aryl group is substituted or unsubstituted.
2. The compound of claim 1, wherein X is N.
3. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is a substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted containing any one or more selected from N, Q and S A plurality of C 2-20 A heteroaryl group, which is a group,
wherein the "substituted or unsubstituted" means substituted with a substituent selected from deuterium or C 6-60 More than 1 substituent in the aryl group is substituted or unsubstituted.
4. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is unsubstituted phenyl, phenyl substituted with 5 deuterium, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothienyl, carbazolyl, or 9-phenylcarbazolyl.
5. The compound of claim 1, wherein R 5 Is hydrogen.
6. The compound of claim 1, wherein R 6 Is hydrogen.
7. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
8. an organic light emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 7.
CN202080006146.0A 2019-06-04 2020-06-04 Compound and organic light emitting device using the same Active CN113015728B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR20190066108 2019-06-04
KR10-2019-0066108 2019-06-04
PCT/KR2020/007307 WO2020246837A1 (en) 2019-06-04 2020-06-04 Novel compound and organic light emitting device comprising same

Publications (2)

Publication Number Publication Date
CN113015728A CN113015728A (en) 2021-06-22
CN113015728B true CN113015728B (en) 2024-02-20

Family

ID=73652157

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202080006146.0A Active CN113015728B (en) 2019-06-04 2020-06-04 Compound and organic light emitting device using the same

Country Status (3)

Country Link
KR (1) KR102413613B1 (en)
CN (1) CN113015728B (en)
WO (1) WO2020246837A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113549059B (en) * 2021-06-18 2023-04-28 陕西莱特光电材料股份有限公司 Organic compound, and electronic device and electronic apparatus including the same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5831654B1 (en) * 2015-02-13 2015-12-09 コニカミノルタ株式会社 Aromatic heterocycle derivative, organic electroluminescence device using the same, illumination device and display device

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (en) 1999-01-27 2004-05-10 주식회사 엘지화학 New organomattalic complex molecule for the fabrication of organic light emitting diodes
TWI504722B (en) 2010-12-03 2015-10-21 Jnc Corp Benzo[c]carbazole compound having pyridine substituent and organic electroluminescent device
KR102120890B1 (en) * 2012-11-01 2020-06-10 삼성디스플레이 주식회사 Heterocyclic compound and organic light emitting diode comprising the same
KR102287345B1 (en) * 2014-05-21 2021-08-06 삼성전자주식회사 Carbazole-based compound and organic light emitting device including the same
CN107591496A (en) 2015-01-05 2018-01-16 北京鼎材科技有限公司 Organic electroluminescence device and its compound
KR102111828B1 (en) * 2016-02-17 2020-05-15 주식회사 엘지화학 Hetero-cyclic compound and organic light emitting device comprising the same
KR101961334B1 (en) * 2016-10-25 2019-03-22 주식회사 엘지화학 Novel hetero-cyclic compound and organic light emitting device comprising the same
KR101978454B1 (en) * 2016-11-29 2019-05-14 주식회사 엘지화학 Novel hetero-cyclic compound and organic light emitting device comprising the same
KR101943428B1 (en) * 2017-03-24 2019-01-30 엘티소재주식회사 Organic light emitting device and composition for organic layer of organic light emitting device

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5831654B1 (en) * 2015-02-13 2015-12-09 コニカミノルタ株式会社 Aromatic heterocycle derivative, organic electroluminescence device using the same, illumination device and display device

Also Published As

Publication number Publication date
WO2020246837A9 (en) 2021-06-03
CN113015728A (en) 2021-06-22
WO2020246837A1 (en) 2020-12-10
KR102413613B1 (en) 2022-06-27
KR20200139645A (en) 2020-12-14

Similar Documents

Publication Publication Date Title
CN113423705B (en) Compound and organic light emitting device using the same
CN110024155B (en) Organic light emitting device
CN113166112B (en) Compound and organic light emitting device comprising the same
CN113423706B (en) Novel compound and organic light emitting device comprising the same
CN111051292B (en) Heterocyclic compound and organic light-emitting device using same
CN113227081B (en) Compound and organic light emitting device using the same
CN113272307B (en) Compound and organic light emitting device using the same
CN113039183B (en) Novel compound and organic light emitting device comprising the same
CN112789272B (en) Compound and organic light emitting device comprising the same
CN112739704B (en) Novel compound and organic light emitting device comprising the same
CN111328329B (en) Novel heterocyclic compound and organic light-emitting device using same
CN111344285B (en) Heterocyclic compound and organic light-emitting device using same
CN113015728B (en) Compound and organic light emitting device using the same
CN113015729B (en) Compound and organic light emitting device using the same
CN117580834A (en) Novel compound and organic light emitting device using the same
CN114945553B (en) Compound and organic light emitting device comprising the same
CN112771036B (en) Compound and organic light emitting device using the same
CN113260608B (en) Novel compound and organic light emitting device comprising the same
CN116745298A (en) Novel compound and organic light emitting device comprising the same
CN113439082B (en) Compound and organic light emitting device comprising the same
CN116438154A (en) Novel compound and organic light emitting device comprising the same
CN114097103A (en) Organic light emitting device
CN113260620B (en) Compound and organic light emitting device comprising the same
CN113454089B (en) Novel compound and organic light emitting device using the same
CN112805276B (en) Novel compound and organic light emitting device comprising the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant