CN113227063A - Novel compound and organic light emitting device using the same - Google Patents
Novel compound and organic light emitting device using the same Download PDFInfo
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- CN113227063A CN113227063A CN202080007245.0A CN202080007245A CN113227063A CN 113227063 A CN113227063 A CN 113227063A CN 202080007245 A CN202080007245 A CN 202080007245A CN 113227063 A CN113227063 A CN 113227063A
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D407/02—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 two hetero rings
- C07D407/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- 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
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Abstract
The invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
The present application claims priority based on korean patent application No. 10-2019-0017983, 2, 15, 2019, the entire contents of which are incorporated herein by reference.
The present invention relates to a novel compound and an organic light emitting device 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, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An 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 the 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, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exitons) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
[ Prior art documents ]
[ patent document ]
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
L1to L3Each independently is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
a is phenanthryl, triphenylene, dibenzofuranyl or dibenzothiophenyl,
wherein A is unsubstituted or independently selected from C1-20An alkyl group; c6-20An aryl group; and C comprising any one or more heteroatoms selected from N, O and S 2-201 or more substituents in the heteroaryl group,
b is a substituent represented by the following chemical formula 2,
ar is a substituent represented by the following chemical formula 2; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
[ chemical formula 2]
In the above-described chemical formula 2,
x is O or S, and X is O or S,
R1to R3Is one of L and L2Or L3In combination, the remainder are each independently hydrogen; deuterium; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
however, at L2Or L3And R1Or R2In the case of binding, unbound R1Or R2In addition to the hydrogen, the aromatic ring is,
n is an integer of 1 to 4.
In addition, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound represented by 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 life span characteristics can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole adjusting layer 8, a light-emitting layer 4, an electron adjusting layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
Definition of terms
In the context of the present specification,
and
represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a cyano 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 radicals (A), (B), (C), (D), (C), (D), (E), (D), (E) and (D)
Alkyl thio xy); arylthio radicals (A), (B), (C)
Aryl thio xy); alkylsulfonyl (
Alkyl sulfo xy); arylsulfonyl (
Aryl sulfoxy); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heteroaryl groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be substituted with a substituted aryl groupThe explanation is a substituent formed by connecting 2 phenyl groups.
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, the 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 in 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, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, 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.
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 a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the 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-mentioned fluorenyl group is substituted, it may be
And the like. But 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 heteroatom, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the aryl group described above. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and in addition thereto, the above description about the aryl group can be applied. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heteroaryl group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description on the heteroaryl group can be applied.
Compound (I)
In another aspect, the present invention provides an amine compound represented by the above chemical formula 1.
The amine compound represented by the above chemical formula 1 includes both any one of the substituents phenanthryl, triphenylene, dibenzofuranyl and dibenzothiophenyl and any one of the substituents benzofuranyl and benzothiophenyl, and thus high efficiency, low driving voltage, long life, and the like of an organic light emitting device using the same can be achieved. And the benzofuranyl or benzothienyl substituent is represented by the formula 2, wherein the phenanthryl group,Any substituent of triphenylene, dibenzofuranyl and dibenzothiophenyl with R of the above chemical formula 21Or R2In the case of binding, unbound R is used1Or R2The organic light emitting device using the hydrogen compound is excluded from the present invention because it has higher voltage, lower efficiency, and poorer life characteristics than the organic light emitting device using the compound represented by the above chemical formula 1, as can be confirmed in the comparative examples described later.
In the above chemical formula 1, preferably, L1To L3Each independently a single bond, phenylene, biphenyldiyl, or naphthylene.
More preferably, L1To L3Each independently is a single bond, or is selected from any one of the following groups:
preferably, A is phenanthryl, triphenylene, dibenzofuranyl or dibenzothiophenyl, wherein A is unsubstituted or independently selected from C1-20Alkyl and C 6-601 to 3 substituents in the aryl group.
More preferably, a is represented by any one of the following chemical formulae a1 to a 4.
In the above chemical formulas a1 to a4,
each R is independently hydrogen or C6-20And (4) an aryl group.
At this time, 2R in the chemical formulas a3 and a4 may be the same as or different from each other, for example, each R is independently hydrogen, phenyl or naphthyl.
Preferably, in the above chemical formula 2, L is not substituted2Or L3Bound R1To R3Each independently of the others is hydrogen, deuterium, C1-10Alkyl or C6-20Aryl, n is 1,2 or 3. In this case, when n is 2 or more, R3The same or different from each other.
More preferably, the substituent represented by the above chemical formula 2 is represented by any one of the following chemical formulae b1 to b 3:
in the above chemical formulas b1 to b3,
x is O or S, and X is O or S,
R1and R2Each independently is C1-10Alkyl or C6-20An aryl group, a heteroaryl group,
R3and R1' to R3' independently of one another are hydrogen, C1-10Alkyl radical, C6-20Aryl, or C containing a heteroatom O or S2-20Heteroaryl, 2R in formula b23May be the same as or different from each other.
Most preferably, in the above chemical formulas b1 and b2,
R1is methyl, ethyl, phenyl, biphenyl or naphthyl,
R2is methyl, ethyl, phenyl or biphenyl,
R3each independently of the others is hydrogen, methyl or phenyl,
in the above-described chemical formula b3,
R1' to R3' are each independently hydrogen, methyl, isopropyl, naphthyl, phenyl or dibenzothienyl.
Preferably, Ar is a substituent represented by the above chemical formula 2; any one aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spiro [ cyclopentane-1, 9 '-fluorene ] yl and spiro [ cyclohexane-1, 9' -fluorene ] yl; or any one heteroaryl group selected from the group consisting of dibenzofuranyl, dibenzothienyl and carbazolyl,
wherein the above aryl or heteroaryl groups are each independently unsubstituted or each independently selected from deuterium, C1-10Alkyl and C 6-201 to 5 of the aryl radicalsSubstituent groups.
More preferably, the above aryl or heteroaryl groups are each independently unsubstituted or substituted with 1 to 5 substituents each independently selected from deuterium, methyl and phenyl.
Most preferably, Ar is any one selected from the group consisting of:
in the above-mentioned group, the group,
y is O, S, N (phenyl) or C (methyl)2。
Preferably, the above compound is represented by any one of the following chemical formulas 1-1 to 1-6:
in the above chemical formulas 1-1 to 1-6,
for L1To L3The descriptions of B and Ar are the same as those in the above chemical formula 1,
q is O or S, and Q is O or S,
r is hydrogen, phenyl or naphthyl.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
on the other hand, as an example, the compound represented by the above chemical formula 1 may be produced by a production method as shown in the following reaction formula 1. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
[ reaction formula 1]
In the above reaction formula 1, each X' is independently a halogen, preferably bromine or chlorine, and the definitions of the remaining substituents are the same as those described above.
The step 1-1 is a step of introducing an SM2 radical into a primary amine of a starting material SM1 to produce an intermediate compound X (int.x), and the step 1-2 is a step of introducing an SM3 radical into a secondary amine of the intermediate compound X (int.x) to produce a compound represented by the above chemical formula 1 as a tertiary amine compound. The above steps 1-1 and 1-2 are both carried out by a Buchwald-Hartwig reaction, which is preferably carried out in the presence of a palladium catalyst. Such a manufacturing method can be further embodied in the manufacturing examples described later.
Organic light emitting device
In another aspect, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have 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 a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have 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, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller or greater number of organic layers may be included.
The organic light-emitting device according to the present invention may have a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on the substrate. The organic light-emitting device according to the present invention may have a reverse structure (inverted type) in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on the 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, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above hole transport layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a hole adjusting layer 8, a light-emitting layer 4, an electron adjusting layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the hole transport layer, the hole adjusting layer, or both the hole transport layer and the hole adjusting 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 the above chemical formula 1. In addition, when 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 produced as follows: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes 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); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject 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 LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. The hole-transporting substance is not limited to the compound represented by chemical formula 1, or an arylamine organic substance, a conductive polymer, a block copolymer in which a conjugated portion and a non-conjugated portion are present, or the like can be used.
The hole-regulating layer refers to a layer in which: the organic light emitting device is formed on the hole transport layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting hole mobility to prevent excessive electron transfer and increase the hole-electron bonding probability. The hole-controlling layer contains a hole-controlling substance, and examples of such a hole-controlling substance include, but are not limited to, compounds represented by the above chemical formula 1, arylamine-based organic substances, and the like.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazoleA compound of (a); poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light-emitting layer may contain a host material and a dopant material as described above. The host material may further contain an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The electron control layer is a layer including: the organic light emitting device is formed on the light emitting layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the electron mobility to prevent excessive hole migration and increase the hole-electron combination probability. The electron control layer contains an electron control substance, and the electron control substanceFor example, triazine-containing azine derivatives, triazole derivatives, triazine derivatives, and triazine derivatives,
Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.
The electron injection and transport layer is a layer which injects electrons from the electrode and transports the received electrons to the light emitting layer, and functions as both an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the electron adjusting layer. Such an electron injecting and transporting substance is a substance capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is suitable for a substance having a high electron mobility. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline, Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but are not limited thereto. Or with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material 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 the organic light emitting device.
The manufacture 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 provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
Synthesis example 1: manufacture of substituents
In order to introduce the substituent represented by the above chemical formula 2 into the compound represented by the above chemical formula 1, intermediate compounds INT. (b1), INT. (b2) and INT. (b3) were produced using the following reaction formulae 2-1, 2-2 and 2-3, respectively.
[ reaction formula 2-1]
In the above reaction formula 2-1, X' is a halogen, and the description of the remaining substituents is the same as that described above. The step 2-1a is a step of introducing a bromine group into the starting material SM1(b1), and the step 2-1b is a step of introducing a linker group by suzuki coupling reaction to produce the intermediate compound INT. (b 1). However, L2When it is a single bond, step 2-1b may be omitted. The specific production method is as follows.
1) Step 2-1 a: production of intermediate Compound SM2(b1)
After dissolving SM1(b1) (1 equivalent) in THF (excess), the temperature was lowered to-78 deg.C, 2.5M N-BuLi (1 equivalent) was added dropwise, and after stirring for 3 hours, N-bromosuccinimide (1 equivalent) was added. Then, the reaction mixture was heated to room temperature, stirred for 10 hours, and 1N HCl (excess) was added to complete the reaction. After completion of the reaction, the solvent was removed by layer separation, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15) to produce the title compound.
2) Step 2-1 b: production of intermediate Compound INT (b1)
After adding SM2(b1) (1 equivalent) and SM3(1.02 equivalent) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 vol% relative to THF) was added, tetrakis (triphenylphosphine) palladium (2 mol%) was added, and the mixture was stirred under heating for 10 hours. The temperature is reduced to normal temperature, and after the reaction is finished, the potassium carbonate aqueous solution is removed, and layer separation is carried out. After removal of the solvent, vacuum distillation and recrystallization from ethyl acetate and hexane gave the title compound.
[ reaction formula 2-2]
In the above reaction formula 2-2, X' is a halogen, and the description of the remaining substituents is the same as that described above. The step 2-2a is a step of introducing a bromine group into the starting material SM1(b2), and the step 2-2b is a step of introducing a linker group by suzuki coupling reaction to produce the intermediate compound INT. (b 2). However, L2When it is a single bond, step 2-2b may be omitted. The specific manufacturing method is as follows:
1) step 2-2 a: production of intermediate Compound SM2(b2)
After dissolving SM1(b2) (1 eq) in DMF (excess), the temperature was lowered to 0 ℃ and after stabilization of the temperature, N-bromosuccinimide (1 eq) was added. Then, the reaction mixture was heated to room temperature, stirred for 1 hour, and then 1N HCl (excess) was added to complete the reaction. After completion of the reaction, the solvent was removed by layer separation, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15) to obtain the title compound.
2) Step 2-2 b: production of intermediate Compound INT (b2)
The title compound was obtained in the same manner as in the above step 2-1b, except that SM2(b2) was used instead of SM2(b1) as the starting material in the above step 2-1 b.
[ reaction formulae 2 to 3]
In the above reaction formula 2-3, X' is a halogen, and the description of the remaining substituents is the same as that described above. The above step 2-3 is a step of introducing a linking group by suzuki coupling reaction to produce an intermediate compound INT. (b 3). In this case, the starting material SM1(b3) can be prepared by the Journal "patent and selective non-benzodioxole-associating endothiolin-A receptor antagonists (Journal of Medicinal Chemistry,1997, vol.40, #3, p.322-330)" and "Zeolite-catalyzed synthesis of 2, 3-unsubstuted benzene [ b 3]]L. Furan via the interaction of 2-aryloxoacetate acids (Tetrahedron,2015, vol.71, #29, p.4835-4841) and the like2When the bond is a single bond, step 2-3 may be omitted. The specific production method is as follows.
1) Step 2-3: production of intermediate Compound INT (b3)
The title compound was obtained in the same manner as in the above step 2-1b, except that SM1(b3) was used instead of SM2(b1) as the starting material in the above step 2-1 b.
The intermediate compounds of the following table 1 were obtained using the methods of the above reaction formulas 2-1 to 2-3, and the respective yields and MS data are shown below.
[ Table 1]
Synthesis example 2: production of compounds 1 to 21 represented by chemical formula 1 compounds represented by the above chemical formula 1 were produced by the following reaction formula 1.
[ reaction formula 1]
In the above reaction formula 1, each X' is independently a halogen, preferably bromine or chlorine, and the definitions of the remaining substituents are the same as those described above. The specific production method is as follows.
1) Step 1-1: production of intermediate compounds INT.X (X1-X21)
SM1(1 equivalent), SM2(1.02 equivalent), and sodium tert-butoxide (1.4 equivalent) were added to xylene, heated, stirred, refluxed, and [ bis (tri-tert-butylphosphino) ] palladium (1 mol%) was added. Then, the temperature was lowered to normal temperature, and after the reaction was completed, recrystallization was performed using tetrahydrofuran and ethyl acetate to obtain intermediate compounds X1 to X21 shown in table 2 below, and the respective yields and MS data were as follows.
[ Table 2]
2) Step 1-2: production of Final Compounds 1 to 21
The intermediate compounds int.x (1 equivalent), SM3(1.02 equivalent) and sodium tert-butoxide (1.4 equivalent) were added to xylene, heated and stirred, refluxed, and [ bis (tri-tert-butylphosphine) ] palladium (1 mol%) was added. Then, the temperature was lowered to room temperature, and after the reaction was completed, recrystallization was performed using tetrahydrofuran and ethyl acetate to obtain the following final compounds 1 to 21, the respective yields and MS data of which are shown in table 3.
[ Table 3]
Synthesis example 3: production of Compound 22 represented by chemical formula 1
The substituent-L is produced by the following reaction scheme 12-B and x-L3-Ar is the same as the final compound 22 represented by the above chemical formula 1.
[ reaction formula 1' ]
In the above reaction formula 1', X' is halogen, preferably bromine or chlorine, and the definitions of the remaining substituents are the same as those described above. Specifically, the final compound 22 was obtained in the same manner as in step 1-1 of synthesis example 2, and the yield and MS data were as shown in table 4.
[ Table 4]
Example 1: fabrication of OLEDs
ITO (indium tin oxide) is added
The glass substrate (corning 7059 glass) coated with a thin film was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fisher Co, and the distilled water used was distilled water obtained by twice filtering with a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.
On the ITO transparent electrode thus prepared, HI-1 (hexanitrile hexaazatriphenylene) was added as a precursor
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, compound 1 synthesized in production example 2 was used as a hole-transporting substance
After vacuum evaporation, HT2 was deposited on the hole transport layer to a film thickness
Vacuum evaporation was performed to form a hole-regulating layer.
Then, on the hole-regulating layer, as a light-emitting layer, a host BH1 and a dopant BD1 compound (25:1) were added
Vacuum evaporation is performed to a thickness of (1).
Then, the E1 compound is added
After forming an electron control layer by vapor deposition, the E2 compound and LiQ were deposited at a ratio of 1:1 (wt%)
Thereby performing thermal vacuum evaporation as an electron injection and transport layer in sequence. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the cathode is formed by vapor deposition to produce an organic light-emitting device.
In the above process, the evaporation speed of the organic material is maintained
Second, maintenance of lithium fluoride
Vapor deposition rate per second, aluminum maintenance
Vapor deposition rate per second.
Examples 2 to 7 and comparative examples 1 to 3
An organic light-emitting device was produced in the same manner as in example 1, except that the compound described in table 5 below was used instead of the compound 1 used in the hole transport layer.
The compounds used in the above examples and comparative examples are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples 1 to 7 and comparative examples 1 to 3, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in the following table 5. At this time, T95 refers to the time required for the luminance to decrease from the initial luminance to 95%.
[ Table 5]
As shown in table 5 above, it was confirmed that the organic light emitting device using the compound of the present invention as a material for a hole transport layer exhibited excellent characteristics in terms of driving voltage, efficiency, and lifetime, compared to the organic light emitting device using the compound of comparative example as a material for a hole transport layer, by smooth injection of holes into a light emitting layer and balance of holes and electrons according to the chemical structure of the organic light emitting device.
Example 8: fabrication of OLEDs
ITO (indium tin oxide) is added
The glass substrate (corning 7059 glass) coated with a thin film was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Hill corporation, and distilled water obtained by twice filtration using a filter manufactured by Millipore corporation was used as distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.
On the ITO transparent electrode thus prepared, HI-1 (hexanitrile hexaazatriphenylene) was added as a precursor
The hole injection layer is formed by thermal vacuum deposition. HT1 as a substance for transporting holes is formed on the hole injection layer
After vacuum deposition, compound 2 synthesized in production example 2 was deposited on the hole transport layer to form a film
Vacuum evaporation is performed to form a hole regulating layer.
Then, on the hole-regulating layer, as a light-emitting layer, a host BH1 and a dopant BD1 compound (25:1) were added
Vacuum evaporation is performed to a thickness of (1).
Then, the E1 compound is added
After forming an electron control layer by vapor deposition, the E2 compound and LiQ were deposited at a ratio of 1:1 (wt%)
Thereby performing thermal vacuum evaporation as an electron injection and transport layer in sequence. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the cathode is formed by vapor deposition to produce an organic light-emitting device.
In the above process, the evaporation speed of the organic material is maintained
Second, maintenance of lithium fluoride
Vapor deposition rate per second, aluminum maintenance
Vapor deposition rate per second.
Examples 9 to 29 and comparative examples 4 to 7
An organic light-emitting device was produced in the same manner as in example 8, except that compounds shown in table 6 below were used instead of compound HT1 used in the hole transport layer and compound 2 used in the hole regulating layer.
Experimental example 2
When a current was applied to the organic light emitting devices manufactured in the above examples 8 to 29 and comparative examples 4 to 7, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in the following table 6. At this time, T95 refers to the time required for the luminance to decrease from the initial luminance to 95%.
[ Table 6]
As shown in table 6 above, it was confirmed that the organic light emitting device using the compound of the present invention as a hole adjusting layer material or as both a hole adjusting layer material and a hole transporting layer material exhibited excellent characteristics in terms of driving voltage, efficiency and lifetime as compared to the organic light emitting device using the compound of comparative example by the smooth injection of holes into the light emitting layer and the balance of holes and electrons according to the chemical structure of the organic light emitting device.
[ description of symbols ]
1: substrate 2: anode
3: hole transport layer 4: luminescent layer
5: electron injection and transport layer 6: cathode electrode
7: hole injection layer 8: hole-regulating layer
9: an electron-modulating layer.
Claims (10)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
L1to L3Each independently is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
a is phenanthryl, triphenylene, dibenzofuranyl or dibenzothiophenyl,
wherein A is unsubstituted or each independently selected from C1-20An alkyl group; c6-20An aryl group; and C comprising any one or more heteroatoms selected from N, O and S2-201 or more substituents in the heteroaryl group,
b is a substituent represented by the following chemical formula 2,
ar is a substituent represented by the following chemical formula 2; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
chemical formula 2
In the chemical formula 2,
x is O or S, and X is O or S,
R1to R3Is one of L and L2Or L3In combination, the remainder are each independently hydrogen; deuterium; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
however, at L2Or L3And R1Or R2In the case of binding, unbound R1Or R2In addition to the hydrogen, the aromatic ring is,
n is an integer of 1 to 4.
2. The compound of claim 1, wherein L1To L3Each independently a single bond, phenylene, biphenyldiyl, or naphthylene.
3. The compound of claim 1, wherein a is represented by any one of the following formulae a1 to a 4:
in the chemical formulas a1 to a4,
each R is independently hydrogen or C6-20And (4) an aryl group.
4. The compound according to claim 1, wherein the substituent represented by the chemical formula 2 is represented by any one of the following chemical formulae b1 to b 3:
in the chemical formulae b1 to b3,
x is O or S, and X is O or S,
R1and R2Each independently is C1-10Alkyl or C6-20An aryl group, a heteroaryl group,
R3and R1' to R3' independently of one another are hydrogen, C1-10Alkyl radical, C6-20Aryl, or C containing a heteroatom O or S2-20A heteroaryl group.
5. The compound of claim 4, wherein, in the chemical formulas b1 and b2,
R1is methyl, ethyl, phenyl, biphenyl or naphthyl,
R2is methyl, ethyl, phenyl or biphenyl,
R3each independently of the others is hydrogen, methyl or phenyl,
in the chemical formula b3, the chemical formula b,
R1' to R3' are each independently hydrogen, methyl, isopropyl, naphthyl, phenyl or dibenzothienyl.
6. The compound according to claim 1, wherein Ar is a substituent represented by the chemical formula 2; any one aryl group selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spiro [ cyclopentane-1, 9 '-fluorene ] yl and spiro [ cyclohexane-1, 9' -fluorene ] yl; or any one heteroaryl group selected from the group consisting of dibenzofuranyl, dibenzothienyl and carbazolyl,
wherein said aryl or heteroaryl is each independently unsubstituted or each independently selected from deuterium, C1-10Alkyl and C6-201 to 5 substituents in the aryl group.
7. The compound of claim 6, wherein Ar is any one selected from the group consisting of:
in the context of the group in question,
y is O, S, N (phenyl) or C (methyl)2。
8. The compound according to claim 1, wherein the compound is represented by any one of the following chemical formulae 1-1 to 1-6:
in the chemical formulas 1-1 to 1-6,
for L1To L3B and Ar are as defined in claim 1,
q is O or S, and Q is O or S,
r is hydrogen, phenyl or naphthyl.
9. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
10. an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers disposed between the first electrode and the second electrode, 1 or more of the organic layers comprising the compound of any one of claims 1 to 9.
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Also Published As
| Publication number | Publication date |
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| CN113227063B (en) | 2024-05-14 |
| KR20230025838A (en) | 2023-02-23 |
| KR102579367B1 (en) | 2023-09-14 |
| KR102665294B1 (en) | 2024-05-10 |
| KR20200099844A (en) | 2020-08-25 |
| CN117143087A (en) | 2023-12-01 |
| WO2020166874A1 (en) | 2020-08-20 |
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