[go: up one dir, main page]

CN113439082B - Compound and organic light-emitting device containing the same - Google Patents

Compound and organic light-emitting device containing the same Download PDF

Info

Publication number
CN113439082B
CN113439082B CN202080015329.9A CN202080015329A CN113439082B CN 113439082 B CN113439082 B CN 113439082B CN 202080015329 A CN202080015329 A CN 202080015329A CN 113439082 B CN113439082 B CN 113439082B
Authority
CN
China
Prior art keywords
compound
group
deuterium
mmol
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
CN202080015329.9A
Other languages
Chinese (zh)
Other versions
CN113439082A (en
Inventor
金旼俊
李东勋
徐尚德
金曙渊
李多情
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
Priority claimed from PCT/KR2020/008986 external-priority patent/WO2021006652A1/en
Publication of CN113439082A publication Critical patent/CN113439082A/en
Application granted granted Critical
Publication of CN113439082B publication Critical patent/CN113439082B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • 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
    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides a compound and an organic light emitting device comprising the same.

Description

Compound and organic light emitting device comprising the same
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2019-0082849 at 7.9 and korean patent application No. 10-2020-0084099 at 7.8 in 2020, the entire contents of the disclosures of which are incorporated as part of the present specification.
The present invention relates to a compound and an organic light emitting device including 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. With 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, electrons are injected into the organic layer from the cathode, excitons (exciton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
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 literature
(Patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to a compound and an organic light emitting device including 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,
Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more heteroatoms selected from N, O and S,
R 1 to R 6 are each independently hydrogen; deuterium; halogen; cyano group; a nitro group; an amine group; a substituted or unsubstituted C 1-60 alkyl group; substituted or unsubstituted C 3-60 cycloalkyl; a substituted or unsubstituted C 2-60 alkenyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more of the group consisting of N, O and S, or two adjacent substituents of R 1 to R 4 may combine with each other to form a substituted or unsubstituted C 6-60 aromatic ring or a substituted or unsubstituted C 2-60 aromatic heterocyclic ring comprising one or more heteroatoms selected from the group consisting of N, O and S,
A is an integer of 0 to 3,
B is an integer of 0 to 6,
A is a substituent represented by the following chemical formula 2,
[ Chemical formula 2]
In the above-mentioned chemical formula 2,
X is O or S, and the X is O or S,
R 7 and R 8 are each independently hydrogen; deuterium; halogen; cyano group; a nitro group; an amine group; a substituted or unsubstituted C 1-60 alkyl group; substituted or unsubstituted C 3-60 cycloalkyl; a substituted or unsubstituted C 2-60 alkenyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group comprising one or more of the group consisting of N, O and S, or two adjacent substituents of R 7 and R 8 may combine with each other to form a substituted or unsubstituted C 6-60 aromatic ring or a substituted or unsubstituted C 2-60 aromatic heterocyclic ring comprising one or more heteroatoms selected from the group consisting of N, O and S,
C is an integer of 0 to 3,
D is an integer of 0 to 4,
A. b, c and d are each 2 or more, the substituents in parentheses are the same or different from each other.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode; a second electrode provided opposite to the first electrode; and a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer contains a compound represented by chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 is used as a material of an organic layer of an organic light emitting device, so that an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics of the organic light emitting device can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting 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 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
(Definition of terms)
In the present description of the invention,AndRepresents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amine group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio (Alkyl thioxy); arylthio (Aryl thioxy); alkylsulfonyl (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 containing N, O and 1 or more substituents in 1 or more heteroaryl groups in the S atom, or a substituent linked with 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 group 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 group may be a group 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 group 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 terphenyl, 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 this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present invention is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl 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 heteroaryl groups include xanthene (xanthone), thioxanthene (thioxanthen), thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl,Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isoOxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
The term "aromatic ring" used in the present specification is understood to include not only a monocyclic or condensed polycyclic ring containing only carbon atoms as ring-forming atoms and having aromaticity (aromaticity) throughout the molecule, but also a condensed polycyclic ring formed by connecting a plurality of monocyclic rings having aromaticity, such as fluorene rings, with adjacent substituents. In this case, the number of carbon atoms of the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but the present invention is not limited thereto. The aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a fluorene ring, or the like, but is not limited thereto.
The term "aromatic heterocycle (heterocyclic ring)" used in the present specification means a heteromonocyclic or heterocondensed polycyclic ring which contains 1 or more hetero atoms in O, N and S as ring-forming atoms in addition to carbon atoms and which has aromaticity in the whole molecule. The heterocyclic ring has 2 to 60 carbon atoms, or 2 to 30 carbon atoms, or 2 to 20 carbon atoms, but is not limited thereto. The heterocyclic ring may be a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, or the like, but is not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group are the same as those exemplified for the aryl groups 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 this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl 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 heteroaryl 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, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of heteroaryl groups can be applied thereto.
(Compound)
The present invention provides a compound represented by the above chemical formula 1.
The compound represented by the above chemical formula 1 has a structure in which a triazine substituent and a benzocarbazolyl substituent are linked through a dibenzofuranyl phenylene group or a dibenzothiophenyl phenylene group. In particular, the above compounds are characterized in that the benzocarbazolyl group substituent and the dibenzofuranyl/dibenzothiophenyl group substituent are bonded to the benzene ring at the ortho (ortho) position. When such a compound is used as a host material of a light-emitting layer, energy transfer to a dopant is smoothly performed as compared with a compound in which a benzocarbazolyl substituent and a dibenzofuranyl/dibenzothiophenyl substituent are bonded at the meta (meta) or para (para) position, and thus the driving voltage of an organic light-emitting device can be reduced and the efficiency and lifetime characteristics can be remarkably improved.
Preferably, R 1 to R 6 are each independently hydrogen, deuterium, or C 6-20 aryl; or alternatively
R 5 and R 6 are each independently hydrogen, deuterium, or C 6-20 aryl, adjacent two of R 1 to R 4 combine with each other to form a benzene ring unsubstituted or substituted with deuterium or C 6-20 aryl, and the remainder may each be independently hydrogen, deuterium, or C 6-20 aryl.
In this case, a and b represent the numbers of R 5 and R 6, respectively, a is 0,1, 2 or 3, and b is 0,1, 2,3 or 4.
Specifically, when two adjacent ones of R 1 to R 4 are bonded to each other without forming a benzene ring, the above compound may be represented by the following chemical formula 1A:
[ chemical formula 1A ]
In the above-mentioned chemical formula 1A,
R 1 to R 6 are each independently hydrogen, deuterium, or C 6-20 aryl,
Ar 1、Ar2、R5、R6, a, b and A are as defined in chemical formula 1 above.
In contrast, when two adjacent ones of R 1 to R 4 are combined with each other to form a benzene ring, the above compound may be represented by the following chemical formula 1B:
[ chemical formula 1B ]
In the above-mentioned chemical formula 1B,
R, R 5、R6 and R 11 to R 14 are each independently hydrogen, deuterium, or C 6-20 aryl,
Ar 1、Ar2, a, b and A are as defined in chemical formula 1 above.
Preferably, the above compound is represented by any one of the following chemical formulas 1-1 to 1-4:
[ chemical formula 1-1]
[ Chemical formulas 1-2]
[ Chemical formulas 1-3]
[ Chemical formulas 1-4]
In the above chemical formulas 1-1 to 1-4,
R 1 to R 6 and R 11 to R 14 are each independently hydrogen, deuterium, or C 6-20 aryl, ar 1、Ar2, a, b, and a are as defined in chemical formula 1 above.
In the above chemical formulas 1-1 to 1-4,
R 5 and R 6 are each independently hydrogen or deuterium,
R 1 to R 4 and R 11 to R 14 may each independently be hydrogen, deuterium or phenyl.
In addition, in the above chemical formula 1-1,
R 1 to R 4 are each independently hydrogen or deuterium; or alternatively
One of R 1 to R 4 is phenyl, and the others may each independently be hydrogen or deuterium.
More specifically, in the above chemical formula 1-1,
R 1 to R 4 are each hydrogen; or R 4 is phenyl, R 1 to R 3 may be hydrogen.
In addition, in the above chemical formula 1-2,
R 1、R2 and R 11 to R 14 are each independently hydrogen or deuterium; or alternatively
One of R 1、R2 and R 11 to R 14 is phenyl, the remainder may each independently be hydrogen or deuterium.
In addition, in the above chemical formulas 1 to 3,
R 1、R4 and R 11 to R 14 are each independently hydrogen or deuterium; or alternatively
One of R 1、R4 and R 11 to R 14 is phenyl, the remainder may each independently be hydrogen or deuterium.
In addition, in the above chemical formulas 1 to 4,
R 3、R4 and R 11 to R 14 are each independently hydrogen or deuterium; or alternatively
One of R 3、R4 and R 11 to R 14 is phenyl, the remainder may each independently be hydrogen or deuterium.
Preferably, ar 1 and Ar 2 may each independently be C 6-20 aryl which is unsubstituted or substituted with 1 or more substituents selected from deuterium and phenyl; or a C 2-20 heteroaryl group containing 1 heteroatom in N, O and S, which is unsubstituted or substituted with 1 or more substituents selected from deuterium and phenyl.
More preferably, ar 1 and Ar 2 are each independently phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl or carbazolyl,
Ar 1 and Ar 2 described above may be unsubstituted or substituted with 1 or more substituents selected from deuterium and phenyl.
For example, ar 1 and Ar 2 may each independently be any one selected from the following groups:
In addition, one of Ar 1 and Ar 2 is phenyl, and the rest is biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothienyl or 9-phenylcarbazolyl; or alternatively
Ar 1 and Ar 2 are phenyl groups; or alternatively
Ar 1 and Ar 2 are biphenyl groups; or alternatively
Ar 1 and Ar 2 are both terphenyl groups; or alternatively
Ar 1 and Ar 2 are naphthyl; or alternatively
Ar 1 and Ar 2 are both anthracenyl; or alternatively
Ar 1 and Ar 2 are phenanthryl; or alternatively
Ar 1 and Ar 2 are both triphenylene groups; or alternatively
Ar 1 and Ar 2 are dibenzofuranyl groups; or alternatively
Ar 1 and Ar 2 are dibenzothienyl; or alternatively
Ar 1 and Ar 2 may both be 9-phenylcarbazolyl.
At this time, ar 1 and Ar 2 may be the same or different from each other.
In addition, R 7 and R 8 are each independently hydrogen or deuterium; or alternatively
R 7 and R 8 are each independently hydrogen or deuterium; or alternatively
Adjacent 2 of R 7 combine with each other to form a benzene ring, and the remaining R 7 and R 8 are each independently hydrogen or deuterium; or alternatively
Adjacent 2 of R 8 combine with each other to form a benzene ring, and the remaining R 8 and R 7 are each independently hydrogen or deuterium; or alternatively
Adjacent 2 of R 7 and adjacent 2 of R 8 are each bonded to each other to form a benzene ring, and the remaining R 7 and R 8 may each be independently hydrogen or deuterium.
In this case, c and d represent the numbers of R 7 and R 8, respectively, c is 0, 1, 2 or 3, and d is 0, 1, 2, 3 or 4.
More preferably, a is dibenzofuranyl, dibenzothienyl, benzonaphthofuranyl, or benzonaphthothienyl, where a may be unsubstituted or may be substituted with one or more deuterium.
Most preferably, a is any one selected from the following groups:
In addition, the above-mentioned compounds may be represented by any one of the following chemical formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1 and 1-4-1:
In the above chemical formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1 and 1-4-1,
Ar 1、Ar2 and A are as defined in chemical formula 1 above.
For example, the above compound is any one selected from the following compounds:
On the other hand, as an example, the compound represented by the above chemical formula 1 can be produced by a production method shown in the following reaction formula 1.
[ Reaction type 1]
In the above reaction formula 1, X is each independently halogen, preferably bromine or chlorine, and the definition of the other substituents is the same as the above description.
Specifically, the compound represented by the above chemical formula 1 is produced by combining the starting materials SM1 and SM2 through an amine substitution reaction. Such amine substitution reactions are preferably carried out in the presence of a palladium catalyst and a base. The reactive group used for the amine substitution reaction may be appropriately changed, and the method for producing the compound represented by chemical formula 1 may be more specifically described in the production examples described below.
(Organic light-emitting device)
In addition, 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 provided opposite to the first electrode; and a light-emitting layer provided between the first electrode and the second electrode, wherein the light-emitting layer contains a compound represented by 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 a first electrode is an anode and a second electrode is a cathode, and 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 (INVERTED TYPE)) in which a first electrode is a cathode and a second electrode is an anode, and the cathode, 1 or more organic layers, and the 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 constituted by a substrate 1, an anode 2, a light-emitting 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 light emitting 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 3, a hole blocking layer 8, an electron injection and transport layer 9, 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 light emitting layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that the above-described light emitting layer contains the compound according to the present invention and is manufactured by the method as described above.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. This can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical Vapor Deposition: physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), 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 (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, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. 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); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive compounds such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are 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; a multilayer structure such as LiF/Al or LiO 2/Al, but 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 metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive compound, but are not limited thereto.
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 an arylamine-based organic substance, a conductive compound, and a block copolymer having both conjugated and unconjugated portions, but the present invention is not limited thereto.
The organic light emitting device according to an embodiment may further include an electron suppressing layer on the hole transporting layer. The electron suppression layer refers to the following layer: the hole transport layer is preferably formed on the light emitting layer, and is preferably provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility, thereby preventing excessive migration of electrons and improving the probability of hole-electron bonding. The electron blocking layer contains an electron blocking material, and as an example of such an electron blocking material, a compound represented by the above chemical formula 1, an organic compound of an arylamine group, or the like can be used, but the present invention is not limited thereto.
The light emitting layer may include a host material and a dopant material. As the host material, a compound represented by the above chemical formula 1 may be used. In addition, as the host material, in addition to the compound represented by the above chemical formula 1, an aromatic condensed ring derivative, a heterocyclic compound, or the like may be further used. 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, ladder-type 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. 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,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. 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.
More specifically, as the dopant material, the following compounds may be used, but are not limited thereto:
In addition, the organic light emitting device according to an embodiment may further include a hole blocking layer on the light emitting layer. The hole blocking layer refers to the following layer: the organic light-emitting device is preferably formed on the light-emitting layer, and preferably includes a layer which is in contact with the light-emitting layer, and which serves to improve the efficiency of the organic light-emitting device by adjusting electron mobility, thereby preventing excessive migration of holes and increasing the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance, and as examples of such a hole blocking substance, azine derivatives including triazines, triazole derivatives, and the like can be used, The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
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 the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having high mobility for electrons. Specific examples include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq 3, 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, and 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, liF, naF, naCl, csF, li 2 O, baO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and,Azole (S),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 according to the present invention may be contained in an organic solar cell or an organic transistor in addition to the 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 A: production of Compound a
1) Production of Compound a-1
300.0G (1.0 eq.) of naphthalene-2-amine, 592.7g (1.0 eq.) of 1-bromo-2-iodobenzene, 302.0g (1.5 eq.) of NaOtBu, 4.70g (0.01 eq.) of Pd (OAc) 2, 12.12g (0.01 eq.) of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos) were dissolved in 5L of 1, 4-diReflux and stir the alkane. After 3 hours, at the end of the reaction, the solvent was removed under reduced pressure. Then, the mixture was completely dissolved in ethyl acetate, washed with water, and depressurized again to remove about 70% of the solvent. Hexane was again added under reflux to allow crystals to fall, and the crystals were cooled and filtered. This was subjected to column chromatography, whereby 443.5g (yield 71%) of compound a-1 was obtained. M+h + =299.
2) Production of Compound a (5H-benzo [ b ] carbazole, 5H-benzol [ b ] carbazole)
443.5G (1.0 eq) of Pd (t-Bu 3P)2; 463.2g (2.00 eq)) of compound a-1; 8.56g (0.01 eq) of K 2CO3 are added to 4L of diethylacetamide (Dimethylacetamide), refluxed and stirred for 3 hours, the reaction is poured into water to allow crystals to fall, filtered, the filtered solid is completely dissolved in 1, 2-dichlorobenzene, washed with water, the solution in which the product is dissolved is concentrated under reduced pressure to allow crystals to fall, cooled and filtered, and purified by column chromatography to give 174.8g (yield 48%) of compound a (5H-benzo [ b ]).
[M+H]+＝218
Synthesis example B: production of Compound b
Compound b (7H-dibenzo [ b, g ] carbazole, 7H-dibenzo [ b, g ] carbaz ole) was obtained in the same manner as in synthesis example a above, except that 1-bromo-2-iodonaphthalene was used instead of 1-bromo-2-iodobenzene.
[M+H]+＝268
Synthesis example C: production of Compound c
Compound c (6H-dibenzo [ b, H ] carbazole, 6H-dibenzo [ b, H ] carbazole) was obtained in the same manner as in synthesis example a above, except that 2, 3-dibromonaphthalene was used instead of 1-bromo-2-iodobenzene.
[M+H]+＝268
Synthesis example D: production of Compound d
Compound d (13H-dibenzo [ a, H ] carbazole, 13H-dibenzo [ a, H ] carbazole) was obtained in the same manner as in synthesis example a above, except that 2-bromo-1-iodonaphthalene was used instead of 1-bromo-2-iodobenzene.
[M+H]+＝268
Synthesis example 1: production of Compound 1
Compound 1-1 (20 g,35.7 mmol), compound a (7.8 g,35.7 mmol), sodium tert-butoxide (6.9 g,71.4 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.7 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 16.1g of compound 1 was obtained.
(Yield 61%, MS: [ M+H ] + =742)
Synthesis example 2: production of Compound 2
Compound 2-1 (20 g,33.3 mmol), compound a (7.2 g,33.3 mmol), sodium tert-butoxide (6.4 g,66.7 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.7 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 14.1g of compound 2 was obtained.
(Yield 54%, MS: [ M+H ] + =782).
Synthesis example 3: production of Compound 3
Compound 3-1 (20 g,28.9 mmol), compound a (6.3 g,28.9 mmol), sodium tert-butoxide (5.6 g,57.9 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 16.4g of compound 3 was obtained.
(Yield 65%, MS: [ M+H ] + =873)
Synthesis example 4: production of Compound 4
Compound 4-1 (20 g,30.8 mmol), compound a (6.7 g,30.8 mmol), sodium tert-butoxide (5.9 g,61.5 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 15.1g of compound 4 was obtained.
(Yield 59%, MS: [ M+H ] + =832)
Synthesis example 5: production of Compound 5
Compound 5-1 (20 g,27.5 mmol), compound a (6 g,27.5 mmol), sodium t-butoxide (5.3 g,54.9 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.5 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 16.2g of compound 5 was obtained.
(Yield 65%, MS: [ M+H ] + =910)
Synthesis example 6: production of Compound 6
Compound 6-1 (20 g,30 mmol), compound a (6.5 g,30 mmol), sodium tert-butoxide (5.8 g,60 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 17.3g of compound 6 was obtained.
(Yield 68%, MS: [ M+H ] + =848)
Synthesis example 7: production of Compound 7
Compound 7-1 (20 g,30.7 mmol), compound a (6.7 g,30.7 mmol), sodium tert-butoxide (5.9 g,61.3 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 12.3g of compound 7 was obtained.
(Yield 48%, MS: [ M+H ] + =834)
Synthesis example 8: production of Compound 8
Compound 8-1 (20 g,30.8 mmol), compound a (6.7 g,30.8 mmol), sodium tert-butoxide (5.9 g,61.5 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 12.3g of compound 8 was obtained.
(Yield 48%, MS: [ M+H ] + =832)
Synthesis example 9: production of Compound 9
Compound 9-1 (20 g,32.8 mmol), compound a (7.1 g,32.8 mmol), sodium tert-butoxide (6.3 g,65.6 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.7 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 15.6g of compound 9 was obtained.
(Yield 60%, MS: [ M+H ] + =792)
Synthesis example 10: production of Compound 10
Compound 10-1 (20 g,29.3 mmol), compound a (6.4 g,29.3 mmol), sodium tert-butoxide (5.6 g,58.6 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 16.2g of compound 10 was obtained.
(Yield 64%, MS: [ M+H ] + =864)
Synthesis example 11: production of Compound 11
Compound 11-1 (20 g,27.1 mmol), compound a (5.9 g,27.1 mmol), sodium tert-butoxide (5.2 g,54.2 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.5 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 10g of compound 11 was obtained.
(Yield 40%, MS: [ M+H ] + =920)
Synthesis example 12: production of Compound 12
Compound 12-1 (20 g,27.5 mmol), compound a (6 g,27.5 mmol), sodium t-butoxide (5.3 g,55.1 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 17.5g of compound 12 was obtained.
(Yield 70%, MS: [ M+H ] + =908)
Synthesis example 13: production of Compound 13
Compound 13-1 (20 g,29 mmol), compound a (6.3 g,29 mmol), sodium tert-butoxide (5.6 g,58 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 15.4g of compound 13 was obtained.
(Yield 61%, MS: [ M+H ] + =872)
Synthesis example 14: production of Compound 14
Compound 14-1 (20 g,28.3 mmol), compound c (7.6 g,28.3 mmol), sodium tert-butoxide (5.4 g,56.6 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 11.7g of compound 14 was obtained.
(Yield 44%, MS: [ M+H ] + =938)
Synthesis example 15: production of Compound 15
Compound 15-1 (20 g,38 mmol), compound c (10.2 g,38 mmol), sodium t-butoxide (7.3 g,76 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 15g of compound 15 was obtained.
(Yield 52%, MS: [ M+H ] + =758)
Synthesis example 16: production of Compound 16
Compound 16-1 (20 g,29 mmol), 1-phenyl-5H-benzo [ b ] carbazole (1-phenyl-5H-benzol [ b ] carbazole) (8.5 g,29 mmol), sodium tert-butoxide (5.6 g,58 mmol) were added to 400ml of xylene under nitrogen atmosphere, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 14.5g of compound 16 was obtained.
(Yield 53%, MS: [ M+H ] + =948)
Synthesis example 17: production of Compound 17
Compound 17-1 (20 g,31.9 mmol), 1-phenyl-5H-benzo [ b ] carbazole (9.4 g,31.9 mmol), sodium tert-butoxide (6.1 g,63.9 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 17.5g of compound 17 was obtained.
(Yield 62%, MS: [ M+H ] + =884)
Synthesis example 18: production of Compound 18
Compound 18-1 (20 g,30.2 mmol), compound d (8.1 g,30.2 mmol), sodium tert-butoxide (5.8 g,60.4 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 15.6g of compound 18 was obtained.
(Yield 58%, MS: [ M+H ] + =894)
Synthesis example 19: production of Compound 19
Compound 19-1 (20 g,31.9 mmol), compound d (8.5 g,31.9 mmol), sodium tert-butoxide (6.1 g,63.9 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 18.1g of compound 19 was obtained.
(Yield 66%, MS: [ M+H ] + =858)
Synthesis example 20: production of Compound 20
Compound 20-1 (20 g,38 mmol), compound b (10.2 g,38 mmol), sodium t-butoxide (7.3 g,76 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.4 g,0.8 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 17.6g of compound 20 was obtained.
(Yield 61%, MS: [ M+H ] + =758)
Synthesis example 21: production of Compound 21
Compound 21-1 (20 g,32.8 mmol), compound b (8.8 g,32.8 mmol), sodium tert-butoxide (6.3 g,65.6 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.7 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 13.2g of compound 21 was obtained.
(Yield 48%, MS: [ M+H ] + =842)
Synthesis example 22: production of Compound 22
Compound 22-1 (20 g,29.6 mmol), compound a (6.4 g,29.6 mmol), sodium tert-butoxide (5.7 g,59.2 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 15.7g of compound 22 was obtained.
(Yield 62%, MS: [ M+H ] + =857)
Synthesis example 23: production of Compound 23
Compound 23-1 (20 g,29.6 mmol), compound a (6.4 g,29.6 mmol), sodium tert-butoxide (5.7 g,59.2 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 11.4g of compound 23 was obtained.
(Yield 45%, MS: [ M+H ] + =858)
Synthesis example 24: production of Compound 24
Compound 24-1 (20 g,28.9 mmol), compound a (6.3 g,28.9 mmol), sodium tert-butoxide (5.6 g,57.9 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed 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 11.4g of compound 24 was obtained.
(Yield 45%, MS: [ M+H ] + =873)
Synthesis example 25: production of Compound 25
Compound 25-1 (20 g,32.8 mmol), compound a (7.1 g,32.8 mmol), sodium tert-butoxide (6.3 g,65.6 mmol) were added to 400ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-t-butylphosphine) palladium (0) (0.3 g,0.7 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 10.9g of compound 25 was obtained.
(Yield 42%, MS: [ M+H ] + =792)
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. Further, 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 the following a-1 compound was p-doped (p-dopping) at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was vacuum-evaporated to form a film thicknessIs provided. Next, the hole transport layer is formed with a film thicknessAn electron-inhibiting layer was formed by vacuum evaporation of the EB-1 compound described below.
Subsequently, on the electron-inhibiting layer, the RH-1 compound described below as a host material and the Dp-7 compound described below as a dopant material were vacuum-evaporated at a weight ratio of 98:2 to formA red light emitting layer of thickness.
On the light-emitting layer, the film thickness is set toThe hole blocking layer was formed by vacuum evaporation of the HB-1 compound described below. Next, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1, thereby obtaining a composition ofForm an electron injection and transport layer.
On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added toTo aluminiumAnd vapor deposition is performed to form a cathode. /(I)
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeVapor deposition rate of aluminum maintenanceDuring vapor deposition, the vacuum degree is maintained at 2×10 -7 to 5×10 -6 torr, thereby manufacturing an organic light emitting device.
Examples 1 to 25
An organic light-emitting device was manufactured in the same manner as in comparative example 1 above, except that the compound described in table 1 below was used instead of the host substance RH-1 in the organic light-emitting devices of examples 1 to 25. At this time, the specific structures of the compounds used in the examples are shown below.
Comparative examples 2 to 13
An organic light-emitting device was manufactured in the same manner as in comparative example 1 above, except that the compound described in table 1 below was used instead of the host substance RH-1 in the organic light-emitting devices of comparative examples 2 to 13. In this case, the specific structures of the compounds used in the comparative examples are shown below.
Experimental example 1: evaluation of element characteristics
When a current was applied to the organic light emitting devices manufactured in the above examples 1 to 25 and comparative examples 1 to 13, the voltage, efficiency and lifetime were measured (10 mA/cm 2), and the results thereof are shown in table 1 below. Lifetime T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
TABLE 1
As shown in the above table, the organic light emitting device of the example using the compound represented by the above chemical formula 1 as the host material of the red light emitting layer has a lower driving voltage, high efficiency and long life compared to the organic light emitting device of the comparative example. This is determined to be due to the fact that the compound represented by the above chemical formula 1 is smoothly formed in energy transfer to the red dopant as compared with the compound having a structure different from that of the present application used in the comparative example. Therefore, when the compound represented by the above chemical formula 1 was used as a host material of the organic light emitting device, it was confirmed that the driving voltage, light emitting efficiency and/or lifetime characteristics of the organic light emitting device were improved.
[ Description of the symbols ]
1: Substrate 2: anode
3: Light emitting layer 4: cathode electrode
5: Hole injection layer 6: hole transport layer
7: Electron suppression layer 8: hole blocking layer
9: Electron injection and transport layers.

Claims (9)

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,
Ar 1 and Ar 2 are each independently C 6-20 aryl which is unsubstituted or substituted with 1 or more substituents selected from deuterium and phenyl; or a C 2-20 heteroaryl group containing any one or more hetero atoms selected from N, O and S, which is unsubstituted or substituted with 1 or more substituents selected from deuterium and phenyl,
R 1 to R 4 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-20 aryl, or two adjacent substituents in R 1 to R 4 combine with each other to form a substituted or unsubstituted benzene ring,
R 5 and R 6 are each independently hydrogen or deuterium,
A is an integer of 0 to 3,
B is an integer of 0 to 6,
A is a substituent represented by the following chemical formula 2,
Chemical formula 2
In the chemical formula 2 described above, the chemical formula,
X is O or S, and the X is O or S,
R 7 and R 8 are each independently hydrogen; deuterium; or two adjacent substituents in R 7 and R 8 combine with each other to form a substituted or unsubstituted C 6-20 aromatic ring,
C is an integer of 0 to 3,
D is an integer of 0 to 4,
A. b, c and d are each 2 or more, the substituents in parentheses are the same or different from each other,
Wherein "substituted or unsubstituted" means substituted or unsubstituted with deuterium.
2. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-4:
Chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Chemical formulas 1-4
In the chemical formulas 1-1 to 1-4,
R 1 to R 4 are each independently hydrogen, deuterium, or C 6-20 aryl,
R 5、R6 and R 11 to R 14 are each independently hydrogen or deuterium,
Ar 1、Ar2, a, b and A are as defined in claim 1.
3. The compound of claim 1, wherein Ar 1 and Ar 2 are each independently phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, dibenzofuranyl substituted with phenyl, dibenzothienyl substituted with phenyl, or carbazolyl substituted with phenyl,
The Ar 1 and Ar 2 are unsubstituted or substituted with more than 1 deuterium.
4. The compound of claim 1, wherein Ar 1 and Ar 2 are each independently any one selected from the group consisting of:
5. the compound of claim 1, wherein R 7 and R 8 are each independently hydrogen or deuterium; or alternatively
Adjacent 2 substituents in R 7 combine with each other to form a benzene ring, and the remaining R 7 and R 8 are each independently hydrogen or deuterium; or alternatively
Adjacent 2 substituents in R 8 combine with each other to form a benzene ring, and the remaining R 8 and R 7 are each independently hydrogen or deuterium; or alternatively
The adjacent 2 substituents in R 7 and the adjacent 2 substituents in R 8 are each bonded to each other to form a benzene ring, and the remaining R 7 and R 8 are each independently hydrogen or deuterium.
6. The compound of claim 1, wherein a is any one selected from the group consisting of:
7. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1 and 1-4-1:
in the chemical formulas 1-1-1, 1-1-2, 1-2-1, 1-3-1 and 1-4-1,
Ar 1、Ar2 and A are as defined in claim 1.
8. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
9. An organic light emitting device, comprising: a first electrode; a second electrode provided opposite to the first electrode; and a light-emitting layer provided between the first electrode and the second electrode, the light-emitting layer comprising the compound according to any one of claims 1 to 8.
CN202080015329.9A 2019-07-09 2020-07-09 Compound and organic light-emitting device containing the same Active CN113439082B (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
KR20190082849 2019-07-09
KR10-2019-0082849 2019-07-09
KR10-2020-0084099 2020-07-08
KR1020200084099A KR102446406B1 (en) 2019-07-09 2020-07-08 Novel compound and organic light emitting device using same
PCT/KR2020/008986 WO2021006652A1 (en) 2019-07-09 2020-07-09 Novel compound and organic light-emitting device using same

Publications (2)

Publication Number Publication Date
CN113439082A CN113439082A (en) 2021-09-24
CN113439082B true CN113439082B (en) 2024-04-23

Family

ID=74237415

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202080015329.9A Active CN113439082B (en) 2019-07-09 2020-07-09 Compound and organic light-emitting device containing the same

Country Status (2)

Country Link
KR (1) KR102446406B1 (en)
CN (1) CN113439082B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20240357925A1 (en) * 2021-10-27 2024-10-24 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107868067A (en) * 2016-09-28 2018-04-03 株式会社Lg化学 Heterocyclic compound and organic light-emitting device containing same
CN109415374A (en) * 2016-10-24 2019-03-01 株式会社Lg化学 Heterocyclic compound and organic light-emitting element comprising same
WO2019086297A1 (en) * 2017-10-30 2019-05-09 Cynora Gmbh Organic molecules for use in optoelectronic devices

Family Cites Families (5)

* 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
KR101801048B1 (en) * 2009-06-08 2017-11-28 에스에프씨 주식회사 Indolocarbazole derivatives and organoelectroluminescent device using the same
KR101982746B1 (en) * 2012-06-27 2019-05-28 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof
KR102746486B1 (en) * 2016-12-23 2024-12-26 솔루스첨단소재 주식회사 Organic compounds and organic electro luminescence device comprising the same
CN111052428B (en) * 2017-10-27 2023-09-29 株式会社Lg化学 Organic light-emitting device using heterocyclic compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107868067A (en) * 2016-09-28 2018-04-03 株式会社Lg化学 Heterocyclic compound and organic light-emitting device containing same
CN109415374A (en) * 2016-10-24 2019-03-01 株式会社Lg化学 Heterocyclic compound and organic light-emitting element comprising same
WO2019086297A1 (en) * 2017-10-30 2019-05-09 Cynora Gmbh Organic molecules for use in optoelectronic devices

Also Published As

Publication number Publication date
CN113439082A (en) 2021-09-24
KR102446406B1 (en) 2022-09-22
KR20210006867A (en) 2021-01-19

Similar Documents

Publication Publication Date Title
CN113423705B (en) Compound and organic light emitting device using the same
CN113039183B (en) Novel compounds and organic light-emitting devices containing the same
CN113795488B (en) Compound and organic light emitting device comprising the same
CN112805276B (en) Novel compounds and organic light-emitting devices containing the same
CN113195477B (en) Compound and organic light-emitting device containing the same
CN113195480B (en) Compound and organic light-emitting device containing the same
CN119343335A (en) Novel compound and organic light-emitting device containing the same
CN114144402B9 (en) Compound and organic light emitting device comprising the same
CN113195478A (en) Compound and organic light emitting diode comprising same
CN113272307B (en) Compounds and organic light-emitting devices utilizing the same
CN113166112B (en) Compound and organic light-emitting device containing the same
CN112789275B (en) Novel compound and organic light-emitting device containing the same
CN117460719A (en) Novel compounds and organic light-emitting devices containing the same
CN113166126A (en) Compound and organic light-emitting device comprising the same
CN114097103B (en) Organic light emitting device
CN112771036B (en) Compounds and organic light-emitting devices utilizing the same
CN113195481B (en) Compound and organic light-emitting device containing the same
CN113439082B (en) Compound and organic light-emitting device containing the same
CN119053584A (en) Novel compound and organic light emitting device using the same
CN113195479A (en) Compound and organic light emitting device including the same
CN115551851B (en) Novel compound and organic light-emitting device containing the same
CN116615421B (en) Novel compound and organic light-emitting device containing the same
CN113166125B (en) Compound and organic light-emitting device using the same
CN113454089B (en) Novel compounds and organic light-emitting devices utilizing the same
CN113015729B (en) Compound and organic light-emitting device using 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